JP7716191B2 - Liquid crystal composition containing polymerizable compound and liquid crystal display element - Google Patents

Description

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

For example, PSA (Polymer Sustained Alignment) mode liquid crystal display elements have a structure in which polymer structures are formed within the cell to control the pretilt angle of the liquid crystal molecules, and have been put to practical use as liquid crystal display elements due to their high-speed response and high contrast.

PSA mode liquid crystal display elements are manufactured by injecting a liquid crystal composition containing a polymerizable compound between substrates, applying a voltage to align the liquid crystal molecules, and then irradiating them with UV light to polymerize the polymerizable compound and fix the alignment of the liquid crystal molecules.

In recent years, PSA mode LCD display elements, such as 4K and 8K, have come to require high-resolution pixels. As a result, the increased area of wiring and light-shielding sections blocks a significant amount of UV light, and conventional UV irradiation processes can result in problems such as insufficient tilt formation, insufficient polymerization of the polymerizable compound, and a large amount of polymerizable compound remaining. This has also led to confirmed display defects such as image retention (IS), which occurs when the remaining polymerizable compound gradually polymerizes during operation, causing a change in tilt.

For these reasons, there is a demand for liquid crystal compositions that can be stably produced with weaker or less UV light than conventional ones for high-resolution PSA mode liquid crystal display elements.

As an approach to polymerizing liquid crystal compositions containing polymerizable compounds with weaker or less UV light than conventional methods, Patent Documents 1 and 2 introduce technologies for shortening the polymerization reaction rate by including liquid crystal compounds with a terphenyl skeleton or a naphthalene skeleton.

Special Publication No. 2013-503952 International Publication No. 2014/148197

As mentioned above, in recent years, high-resolution PSA-mode liquid crystal display elements have required polymerizable compound-containing liquid crystal compositions that can be stably produced with weaker or less UV light than conventional methods. However, the polymerizable compound-containing liquid crystal compositions containing liquid crystal compounds having a terphenyl skeleton or a naphthalene skeleton described in the examples of Patent Documents 1 and 2 have sufficient polymerization rates, but they exhibit insufficient tilt formation and insufficient tilt stability. For this reason, there is a need for improved properties of polymerizable compound-containing liquid crystal compositions. Such improved properties of polymerizable compound-containing liquid crystal compositions are not limited to applications in PSA-mode liquid crystal display elements, but are also required for polymerizable compound-containing liquid crystal compositions used in liquid crystal display elements of other driving modes.

The problem to be solved by the present invention is to provide a liquid crystal composition containing a polymerizable compound that can be polymerized sufficiently at a high speed, can form a tilt with weak or little UV light, and is useful for producing liquid crystal display elements that have excellent reliability after the UV irradiation process, and to provide a liquid crystal display element using the same.

As a result of extensive research into the above-mentioned problems, the inventors discovered that the above-mentioned problems could be solved by a polymerizable compound-containing liquid crystal composition that contains a compound having a specific structure and a polymerizable compound, with the content of the compound having the specific structure being within a specified range, and thus completed the present invention.

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

(In the formula, R ⁱ¹ and R ⁱ² each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms, in which one or more hydrogen atoms may be substituted by a fluorine atom, and ring A and ring B each independently represent
(a) a 1,4-cyclohexylene group (in which one —CH ₂ — or two or more non-adjacent —CH ₂ — groups may be replaced by —O—).
(b) a 1,4-phenylene group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=).
(c) a group selected from the group consisting of a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one —CH= or two or more non-adjacent —CH= groups present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by —N=), and (d) a 1,4-cyclohexenylene group, wherein the groups (a), (b), (c), and (d) each independently may be substituted with an alkyl group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, a cyano group, or a fluorine atom,
C represents a divalent fused ring group having one or more benzene rings, one or more hydrogen atoms of the fused ring group being optionally substituted by an alkyl group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted by a fluorine atom, or a fluorine atom;
Z ⁱ¹ and Z ⁱ² each independently represent —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 each independently represent 0, 1, or 2;
When a plurality of rings A, B, ^Zi1 and ^Zi2 are present, they may be the same or different.

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

The polymerizable compound-containing liquid crystal composition of the present invention can be sufficiently polymerized at a high speed, and tilt can be formed with weak or little UV light, achieving high tilt stability. Furthermore, the polymerizable compound-containing liquid crystal composition of the present invention can be sufficiently polymerized at a high speed and the UV irradiation time can be shortened, thereby suppressing deterioration of the liquid crystal composition and a decrease in voltage holding ratio (VHR) due to UV irradiation.

Liquid crystal display elements using the polymerizable compound-containing liquid crystal composition of the present invention have a small amount of unreacted polymerizable compound remaining, can form a tilt with weak or little UV light, and exhibit high-speed response, a high VHR, and high tilt stability. They also exhibit excellent display quality, with no or reduced display defects such as alignment defects and burn-in caused by changes in the pretilt angle.

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 below. The compound represented by general formula (i) may also be referred to as the compound of general formula (i) or compound (i). The same applies to other compounds.

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

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

In the polymerizable compound-containing liquid crystal composition of the present invention, by setting the content of the compound represented by general formula (i), i.e., the compound containing a fused ring within its structure, within a predetermined range, the sensitizing effect exerted by the compound represented by general formula (i) enables the polymerizable compound to be sufficiently polymerized at a high rate, making it possible to form a large tilt with weak or little UV light and achieving high tilt stability. Furthermore, because the polymerizable compound-containing liquid crystal composition of the present invention can be sufficiently polymerized at a high rate, it is possible to shorten the UV irradiation time, thereby suppressing deterioration of the liquid crystal composition due to UV irradiation and suppressing a decrease in the voltage holding ratio (VHR).

In addition, liquid crystal display elements using the polymerizable compound-containing liquid crystal composition of the present invention have a small amount of unreacted polymerizable compound remaining, can form a large tilt with weak or little UV light, and exhibit high-speed response, high VHR, and high tilt stability. They also exhibit excellent display quality, with no or reduced display defects such as alignment defects and burn-in caused by changes in the pretilt angle.

In particular, in the manufacture of high-resolution PSA mode liquid crystal display elements such as 4K and 8K, prolonged UV irradiation times significantly reduce production efficiency. In contrast, the polymerizable compound-containing liquid crystal composition of the present invention enables the manufacture of high-resolution PSA mode liquid crystal display elements such as 4K and 8K with short UV irradiation times, making it extremely valuable for industrial use.

Any polymerizable compound-containing liquid crystal composition of the present invention that does not contain the polymerizable compound and the compound represented by general formula (i) may be referred to as the liquid crystal composition of the present invention. Below, 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 a compound represented by general formula (i) in a predetermined content.

In general formula (i), R ⁱ¹ and R ⁱ² each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms. One or more hydrogen atoms present in these groups may be substituted with a fluorine atom.

Because of their high effect of lowering _γ1 , R ⁱ¹ and R ⁱ² are each 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 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms. Furthermore, the alkyl group and alkenyl group are preferably linear.

Furthermore, it is preferable that R ⁱ¹ and R ⁱ² are each independently an alkoxy group having 1 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, since this can increase |Δε| of the polymerizable compound-containing liquid crystal composition.

Furthermore, because of the high effect of improving the reliability of VHR and the like, R ⁱ¹ and R ⁱ² are preferably each independently an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and 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 present in the groups R ⁱ¹ and R ⁱ² may or may not be substituted with a fluorine atom, but it is preferable that R ⁱ¹ and R ⁱ² are not substituted with a fluorine atom.

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

The above groups (a), (b), (c), and (d) may each independently be substituted with an alkyl group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, a cyano group, or a fluorine atom.

Among these, ring A and ring B each independently have the following structure:

Preferably, it represents a group selected from the group consisting of a 1,4-cyclohexylene group, an unsubstituted 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, and a 2,3-difluoro-1,4-phenylene group.

More specifically, because this allows for a faster polymerization rate of the polymerizable compound, ring A and ring B are preferably each independently an unsubstituted 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, or 2,3-difluoro-1,4-phenylene group, and particularly preferably an unsubstituted 1,4-phenylene group. An unsubstituted phenylene group has a UV absorption wavelength band that is longer than that of a phenylene group substituted with another atom, such as a fluorine atom. As a result, a polymerizable compound-containing liquid crystal composition of the present invention, which contains a compound represented by general formula (i) having an unsubstituted phenylene group, can achieve a faster reaction rate of the polymerizable compound and can sufficiently suppress a decrease in VHR, compared to when the composition contains a compound represented by general formula (i) having a substituent.

On the other hand, because this further improves miscibility with other liquid crystal components, it is preferable that ring A and ring B are each independently a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, or a 2,3-difluoro-1,4-phenylene group.

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

In general formula (i), C represents a divalent fused ring group having one or more benzene rings. Here, a fused ring group having one or more benzene rings refers to a group in which multiple rings, including at least one benzene ring, form a fused ring. In addition, a fused ring refers to a ring structure in which two or more rings are bonded together by sharing two or more atoms.

The fused ring group represented by C above is preferably a fused ring group formed by the fusion of two, three, or four rings. In other words, the fused ring group represented by C above is preferably a two-ring fused ring group, a three-ring fused ring group, or a four-ring fused ring group. Of these, a two-ring fused ring group or a three-ring fused ring group is more preferable from the viewpoint of compatibility with other liquid crystal molecules.

Furthermore, among the rings constituting the fused 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 fused ring group within the above range, it becomes easier to achieve both a moderate polymerization rate and high reliability by including the compound represented by general formula (i).

The fused ring group represented by C above may be composed only of benzene rings. Examples of fused ring groups composed only of benzene rings include naphthyl, anthracenyl, and phenanthrenyl groups.

Furthermore, the fused ring group represented by C above may be composed of one or more benzene rings and one or more rings selected from the group consisting of aliphatic monocyclic rings, aromatic heterocyclic rings, and aliphatic heterocyclic rings.

Aliphatic monocycles have a structure in which cyclic bonds are formed only by carbon atoms. The aliphatic monocycle preferably has 4 to 8 carbon atoms, more preferably 4 to 6 carbon atoms, and even more preferably 5 or 6 carbon atoms. Examples of the aliphatic monocycle include a cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclobutene ring, cyclopentene ring, and cyclohexene ring. Among these, the aliphatic monocycle contained in the fused ring represented by C above is preferably a cyclopentane ring or a cyclohexane ring.

The aliphatic heterocycle has a structure in which one, two, or three —CH ₂ — groups in the aliphatic ring are replaced with —O—, —S—, or —NH—. The number of ring members in the aliphatic heterocycle is preferably 4 to 8, more preferably 4 to 6, and even more preferably 5 or 6. Examples of such aliphatic heterocycle include a pyrrolidine ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, a piperidine ring, a tetrahydropyran ring, and a tetrahydrothiopyran ring.

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

Of these, the fused ring group represented by C above is preferably a fused ring group composed of two or three benzene rings, or a fused ring composed of one or two benzene rings and one or two rings selected from the group consisting of a tetrahydrofuran ring, a tetrahydropyran ring, a pyridine ring, a pyrrolidine ring, and a tetrahydrothiophene ring.

One or more hydrogen atoms in the fused ring group represented by C may be substituted with an alkyl group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, or a fluorine atom; however, for ease of compound synthesis, it is preferable that one or more hydrogen atoms in the fused ring group represented by C are unsubstituted.

In the fused ring group represented by C, the bonding position A to Z ⁱ¹ (R ⁱ¹ when n ⁱ¹ is 0) and the bonding position B to Z ⁱ² (R ⁱ² when n ⁱ² is 0) are not particularly limited, but it is preferable that the bonding position A and the bonding position B are located in a straight line.

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

(wherein * represents the point of attachment to Z ⁱ¹ or R ⁱ¹ , and a black dot (●) represents the point of attachment to Z ⁱ² or R ⁱ² .)

In general formula (i), C more preferably represents a fused ring group selected from the following structures among the structures described above.

(wherein * represents the point of attachment to Z ⁱ¹ or R ⁱ¹ , and a black dot (●) represents the point of attachment to Z ⁱ² or R ⁱ² .)

Of the structures described above, it is particularly preferred that C in general formula (i) represent a 2,6-naphthalenediyl group, as this further improves the compatibility between a high polymerization rate and high reliability.

In general formula (i), Z ⁱ¹ and Z ⁱ² each independently represent -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. Among these, Z ⁱ¹ and Z ⁱ² each independently represent preferably -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ - or a single bond, and particularly preferably a single bond in order to increase the polymerization rate of the polymerizable compound.

In general formula (i), when a plurality of Z ^i1s and a plurality of Z ^i2s are present, the plurality of Z ^i1s and the plurality of Z ^i2s may be the same or different.

For example, the compound represented by general formula (i) can have further improved reliability and solubility when Z ⁱ¹ or Z ⁱ² bonded to the fused ring represented by C via one ring A or B represents any of the above-mentioned groups other than a single bond.

In general formula (i), n ⁱ¹ and n ⁱ² each independently represent 0, 1, or 2, but since miscibility with other liquid crystal molecules is good, it is preferable that n ⁱ¹ +n ⁱ² represent 1 or 2, and since miscibility with other liquid crystal molecules and tilt stability are further improved, it is more preferable that n ⁱ¹ +n ⁱ² represent 1. When ^{n i1} +n ⁱ² represents 2, n ⁱ¹ may represent 1 and n ⁱ² may represent 1, or one of n ⁱ¹ or n ⁱ² may represent 2 and the other may represent 0. Among these, since miscibility with other liquid crystal molecules is further improved, it is preferable that one of n ⁱ¹ or n ⁱ² represents 2 and the other represents 0.

In general formula (i), when there are a plurality of rings A, B, ^Zi1 and ^Zi2 , they may be the same or different.

The compound represented by 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 ⁱ¹ and n ⁱ¹² have the same definitions as R ⁱ¹ , R ⁱ² , ring A, ring B, Z ⁱ¹ , Z ⁱ² , n ⁱ¹ and n ⁱ² in the general formula (i), respectively;
n ⁱ¹¹ + n ⁱ¹² represent 1, 2, 3 or 4;
X ⁱ¹¹ to X ⁱ¹⁶ each independently represent an alkyl group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, a fluorine atom, or a hydrogen atom.

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

In general formula (i-1), X ⁱ¹¹ to X ⁱ¹⁶ each independently represent 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 a fluorine atom or a hydrogen atom, and particularly preferably a hydrogen atom.

The number of groups that are hydrogen atoms among X ⁱ¹¹ to X ⁱ¹⁶ is preferably at least 3. Specifically, the number of groups that are hydrogen atoms among X ⁱ¹¹ to X ⁱ¹⁶ is preferably 3, 4, 5, or 6, more preferably 4, 5, or 6, and still more preferably 5 or 6.

In general formula (i-1), preferred aspects of R ⁱ¹¹ , R ⁱ¹² , ring A ⁱ¹ , ring B ⁱ¹ , Z ⁱ¹ and Z ⁱ¹² can be the same as preferred aspects of R ⁱ¹ , R ⁱ² , ring A, ring B, Z ⁱ¹ and Z ⁱ² in general formula (i), respectively.

In general formula (i-1), when n ⁱ¹¹ represents 0, n ⁱ¹² represents 1 or 2, and ring B ⁱ¹ directly bonded to R ⁱ¹² is a 2,3-difluoro-1,4-phenylene group, 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, compared to when R ⁱ¹² is a group other than an alkoxy group, the effect of improving the reactivity of the polymerizable compound when used in combination with the compound represented by general formula (i-1) is higher. 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 preferably an alkyl group having 1 to 3 carbon atoms.

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

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

(wherein R ⁱ¹¹¹ , R ⁱ¹¹² , ring A ⁱ¹¹ , ring B ⁱ¹¹ , Z ⁱ¹¹ and Z ⁱ¹² have the same definitions as R ⁱ¹ , R ⁱ² , ring A, ring B, Z ⁱ¹ and Z ⁱ² in general formula (i), respectively;
Y ⁱ¹¹¹ and Y ⁱ¹¹² each independently represent an alkyl group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, a fluorine atom, or a hydrogen atom;
n ⁱ¹¹¹ and n ⁱ¹¹² each independently represent 0 or 1.

In general formula (i-1-1), Y ⁱ¹¹¹ and Y ⁱ¹¹² are each preferably independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine atom, or a hydrogen atom, more preferably an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a hydrogen atom, and particularly preferably a fluorine atom or a hydrogen atom. One of Y ⁱ¹¹¹ and Y ⁱ¹¹² may be a fluorine atom and the other a hydrogen atom, or both may represent fluorine atoms, or both may represent hydrogen atoms. When Y ⁱ¹¹¹ and Y ⁱ¹¹² are each independently a fluorine atom or a hydrogen atom, the compound represented by general formula (i-1-1) can increase the polymerization rate of the polymerizable compound, further improve miscibility with other liquid crystal components, and obtain high tilt stability.

In general formula (i-1-1), n ⁱ¹¹¹ and n ⁱ¹¹² each independently represent 0 or 1, but from the viewpoint of miscibility with other liquid crystal molecules, n ⁱ¹¹¹ +n ⁱ¹¹² is preferably 0 or 1, and is more preferably 0 because this further improves miscibility with other liquid crystal molecules and tilt stability. When n ⁱ¹¹¹ +n ⁱ¹¹² is 1, n i111 may represent 1 and n ⁱ¹¹² may represent 0, or n ⁱ¹¹¹ may represent 0 and n ⁱ¹¹² may represent 1. Of these, it is preferable that n ⁱ¹¹¹ represent 0 and n ⁱ¹¹² represent 1. This is because the compound represented by general formula (i- ^1-1 ) has a molecular structure in which the ring structure is unevenly distributed on one side of the fused ring at the center, thereby improving miscibility with other liquid crystal molecules.

In the general formula (i-1-1), preferred aspects of R ⁱ¹¹¹ , R ⁱ¹¹² , ring A ⁱ¹¹ , ring B ⁱ¹¹ , Z ⁱ¹¹ and Z ⁱ¹² can be the same as the preferred aspects of R ⁱ¹ , R ⁱ² , ring A, ring B, Z ⁱ¹ and Z ⁱ² in the general formula (i), respectively.

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

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

The compound represented by general formula (i) is preferably each of the compounds represented by the following general formulas (i-1-1-1) to (i-1-1-55). Among these, more preferred compounds are those represented by general formulas (i-1-1-1) to (i-1-1-6), (i-1-1-12) to (i-1-1-17), (i-1-1-23) to (i-1-1-28), (i-1-1-34) to (i-1-1-39), and (i-1-1-45) to (i-1-1-50), more preferred are those represented by general formulas (i-1-1-1) to (i-1-1-4), (i-1-1-34) to (i-1-1-37), or (i-1-1-45) to (i-1-1-48), and particularly preferred are those represented by general formulas (i-1-1-1) to (i-1-1-4).

(In the formula, R ⁱ¹¹¹ and R ⁱ¹¹² have the same definitions as R ⁱ¹ and R ⁱ² in the general formula (i), respectively.)

The compound of general formula (i) can promote the polymerization reaction of the polymerizable compound through its sensitizing effect. However, if the content of the compound of general formula (i) is too high, it may be difficult to form a tilt of sufficient magnitude in a short reaction time, or the VHR may decrease. In contrast, by adjusting the content of the compound of general formula (i) within a specified range, the polymerizable compound-containing liquid crystal composition of the present invention can sufficiently polymerize the polymerizable compound at a high rate, form a tilt of sufficient magnitude in a short time, suppress a decrease in VHR due to UV irradiation, and achieve a good balance of various properties.

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

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

[2] Polymerizable 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 its molecular structure, and by forming a polymer in the manufacturing process of a liquid crystal display device, it is possible to impart a tilt angle to liquid crystal molecules and improve physical properties such as response speed, _Tni , and Δε.

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

[2-1] Polymerizable compound A
The polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more polymerizable compounds A represented by 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 having 1 to 15 carbon atoms, or -Sp ^p2 -P ^p2 , one or two or more non-adjacent -CH ₂ - groups in the alkyl group may each independently be substituted with -CH═CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO-, and one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a cyano group, a fluorine atom, or a chlorine atom;
P ^p1 and P ^p2 each independently represent a group represented by the general formula (P ^p1 -1) to the formula (P ^p1 -9):

(wherein R ^p11 and R ^p12 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms; W ^p11 represents a single bond, —O—, —COO—, or an alkylene group having 1 to 5 carbon atoms; and t ^p11 represents 0, 1, or 2, but when a plurality of R ^p11 , R ^p12 , W ^p11 , and/or t ^p11 are present in a molecule, they may be the same or different.)
Sp ^p1 and Sp ^p2 each independently represent a single bond or a spacer group;
Z ^p1 and Z ^p2 each independently represent 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} —COO—, —COO-CR ^ZP1 ═CH—OCO—, —OCO-CR ^ZP1 ═CH—COO—, —OCO-CR ^ZP1 ═CH—OCO—, —(CH ₂ ) _z -COO—, —(CH 2 ) z -OCO—, —OCO-(CH ₂ ) _z -, —(C═O)—O—(CH ₂ ) _{z -} , —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF ₂ —, —CF ₂ O—, —OCF ₂ —, —CF ₂ CH ₂ —, —CH ₂ CF ₂ —, —CF ₂ CF ₂ —, or —C≡C— (wherein z's each independently represent an integer of 1 to ₄ , and R Each ^{R ZP1} independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and when a plurality of R ^ZP1s are present in a molecule, they may be the same or different. In addition, * in the formula represents the point of attachment to Sp ^p1 or Sp ^p2 .
A ^p1 and A ^p2 each independently represent
(a ^p ) a 1,4-cyclohexylene group (in which one —CH ₂ — or two or more non-adjacent —CH ₂ — groups may be replaced by —O—).
(b ^p ) a 1,4-phenylene group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=), and (c ^p ) a naphthalenediyl group, a 1,2,3,4-tetrahydronaphthalenediyl group, a decahydronaphthalenediyl group, a phenanthrene-2,7-diyl group, or an anthracene-2,6-diyl group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=).
represents a group selected from the group consisting of
A ^p3 represents a group selected from the group consisting of the above groups (a ^p ), (b ^p ), and (c ^p ), and a single bond;
The above groups (a ^p ), (b ^p ) and (c ^p ) each independently represent that a hydrogen atom present in this group may be substituted with a cyano group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms or -Sp ^p2 -P ^p2 ;
m ^p1 represents 0, 1, 2 or 3, and when a plurality of Z ^p1 , A ^p2 , Sp ^p2 and/or P ^p2 are present in a molecule, they may be the same or different,
When m ^p1 is 0 and A ^p1 is a group other than a naphthalenediyl group, a phenanthrene-2,7-diyl group, and an anthracene-2,6-diyl group, A ^p3 represents a group other than a single bond.
In formula (P), R ^p1 is preferably -Sp ^p2 -P ^p2 .

In general formula (P), P ^p1 and P ^p2 each represent a polymerizable group. Here, the polymerizable group in general formula (P) is excluded from the polar group described in the polymerizable compound B described below. ^{P p1} and P ^p2 are each preferably independently any of the groups represented by the above general formulae (P ^p1 -1) to (P ^p1 -3), and are preferably a group represented by the above general formula (P ^p1 -1).

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

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

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

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

In general formula (P), Z ^p1 and Z ^p2 each independently represent 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- is preferred, and 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- is preferred, and only one of -OCH ₂ -, -CH ₂ O-, -C ₂ H ₄ -, -COO-, -OCO-, -COOC ₂ H ₄ -, -OCOC ₂ H _{4 -, -C 2 H 4 OCO-} , -C _{2 H 4 COO-} , -CH=CH-, -(CH ₂ ) ₂ -COO-, -(CH ₂ ) ₂ -OCO-, -OCO-(CH ₂ ) ₂ -, -CH=CH-COO-, -COO-CH=CH-, -OCOCH=CH-, -COO-(CH ₂ ) ₂ - or -C≡C-, and all the others are single bonds; it is preferred that only one present in the molecule is -OCH ₂ -, -CH ₂ O-, -C ₂ H ₄ -, -COO- or -OCO-, and all the others are single bonds, and it is more preferred that all are single bonds.

It is also preferred that only one of Z ^p1 and Z ^p2 present in the molecule is a linking group selected from the group consisting of -CH=CH-COO-, -COO-CH=CH-, -(CH ₂ ) ₂ -COO-, -(CH ₂ ) ₂ -OCO-, -O-CO-(CH ₂ ) ₂ - and -COO-(CH ₂ ) ₂ -, and the other is a single bond.

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

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

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

Here, the naphthalenediyl group and 1,2,3,4-tetrahydronaphthalenediyl group which can be represented by A ^p1 , A ^p2 , and A ^p3 are groups which bond 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 groups which bond to S ^p1 at one of two positions selected from positions 1 to 8 and bond to Z ^p1 or Z ^p2 at the other; in the case of A ^p2 , they are groups which bond to Z ^p1 at one of two positions selected from positions 1 to 8 and bond to Z ^p1 or Z ^p2 at the other; and in the case of A ^p3 , they are groups which bond to Z ^p2 at one of two positions selected from positions 1 to 8 and bond to R ^p1 at the other.

Furthermore, the decahydronaphthalenediyl group which can be represented by A ^p1 , A ^p2 , and A ^p3 is a group which is bonded at two positions selected from positions 1 to 10. Specifically, in the case of A ^p1 , the decahydronaphthalenediyl group is a group which is bonded to S p ^p1 at one of two positions selected from positions 1 to 10 and to Z ^p1 or Z ^p2 at the other; in the case of A ^p2 , it is a group which is bonded to Z ^p1 at one of two positions selected from positions 1 to 10 and to Z ^p1 or Z ^p2 at the other; and in the case of A ^p3 , it is a group which is bonded to Z ^p2 at one of two positions selected from positions 1 to 10 and to R ^p1 at the other.

Examples of naphthalenediyl groups include naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, and naphthalene-2,7-diyl groups. Of these, naphthalene-1,4-diyl and naphthalene-2,6-diyl groups are preferred.

Examples of 1,2,3,4-tetrahydronaphthalenediyl groups include the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, the 1,2,3,4-tetrahydronaphthalene-1,4-diyl group, and the 1,2,3,4-tetrahydronaphthalene-1,5-diyl group. Of these, the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group is preferred.

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

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

Since this reduces the amount of polymerizable compound A remaining after UV light irradiation, it is preferable that at least one hydrogen atom present in the 1,4-phenylene group be substituted with 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 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms. A more preferred example of the alkyl group is a methyl group, and a more preferred example of the alkoxy group is a methoxy group.

Furthermore, since tilt stability can be improved, it is preferable that the 1,4-phenylene group is unsubstituted or that at least one hydrogen atom present in the 1,4-phenylene group is substituted with a fluorine atom.

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

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

Preferable lower limits for the content of polymerizable compound A represented by general formula (P) are 0.01 mass%, 0.03 mass%, 0.05 mass%, 0.08 mass%, 0.1 mass%, 0.15 mass%, 0.2 mass%, 0.25 mass%, and 0.3 mass% relative to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention. Preferable upper limits for the content of polymerizable compound A represented by general formula (P) are 10 mass%, 8 mass%, 5 mass%, 3 mass%, 1.5 mass%, 1.2 mass%, 1 mass%, 0.8 mass%, and 0.5 mass% relative to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention.

If the content of polymerizable compound A represented by general formula (P) in the polymerizable compound-containing liquid crystal composition of the present invention is low, the effects of adding polymerizable compound A represented by general formula (P) are less apparent, and problems such as insufficient tilt formation and poor tilt stability are more likely to occur. Furthermore, problems such as the alignment control force of the liquid crystal composition being weak or weakening over time are more likely to occur. On the other hand, if the content is too high, problems such as a large amount remaining after curing, long curing times, and reduced reliability of the liquid crystal arise. Therefore, by setting the content by combining the above-mentioned upper and lower limits while taking these factors into consideration, the polymerizable compound-containing liquid crystal composition of the present invention can impart a tilt to the liquid crystal molecules at a sufficiently large angle, can maintain high tilt stability and high alignment control force of the liquid crystal composition for a long period of time, and exhibits high reliability.

Specific ranges for the content of polymerizable compound A represented by general formula (P) are, for example, preferably within the range of 0.05% by mass to 10% by mass, preferably within the range of 0.1% by mass to 8% by mass, preferably within the range of 0.1% by mass to 5% by mass, preferably within the range of 0.1% by mass to 3% by mass, preferably within the range of 0.2% by mass to 2% by mass, preferably within the range of 0.2% by mass to 1.3% by mass, preferably within the range of 0.2% by mass to 1% by mass, and preferably within the range of 0.2% by mass to 0.56% by mass, relative to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention.

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

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

Preferred examples of the polymerizable compound A represented by general formula (P) include compounds represented by the following formulas (P-2-1) to (P-2-16).

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

Preferred examples of the polymerizable compound A represented by general formula (P) include compounds represented by the following formulas (P-3-1) to (P-3-15).

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

Preferred examples of polymerizable compound A represented by general formula (P) include polymerizable compounds represented by the following formulas (P-4-1) to (P-4-21).

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

Preferred examples of polymerizable compounds represented by general formula (P) include compounds represented by the following formulas (P-5-1) to (P-5-37).

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

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

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

Polymerizable compound B is a compound having a different structure from polymerizable compound A, and differs from polymerizable compound A in that it has a polar group.

Although polymerizable compound B has the same functions as polymerizable compound A, the inclusion of a polar group in its molecular structure allows it to further exhibit the following function. Specifically, in liquid crystal display elements without an alignment film, the polar groups of the polymer of polymerizable compound B interact with the substrate, thereby imparting vertical alignment to liquid crystal molecules even without an alignment film. Therefore, the polymerizable compound-containing liquid crystal composition of the present invention can be used to manufacture liquid crystal display elements without an alignment film on at least one side of the liquid crystal layer. Furthermore, in liquid crystal display elements with an alignment film, the polar groups of the polymer of polymerizable compound B interact with impurities, such as polar compounds, ionic compounds, and radical compounds, present in the liquid crystal layer or alignment film, thereby adsorbing and capturing the impurities. Therefore, the polymerizable compound-containing liquid crystal composition of the present invention can suppress decreases in resistivity and VHR due to impurities, allowing the manufacture of highly reliable liquid crystal display elements. It is believed that the impurity adsorption and capture function of the polar groups can also be exerted in liquid crystal display elements without an alignment film.

The polymerizable compound B may have a structure having at least one polymerizable group and one or more polar groups, and preferably has a structure having a mesogenic group, one or more polymerizable groups, and one or more polar groups. Details regarding mesogenic groups will be explained later.

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

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

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

The polymerizable group P ^AP1 is preferably bonded to the mesogenic group via a spacer group Sp ^AP1 . Mesogenic groups will be described in detail later. The spacer group Sp ^AP1 preferably represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably a single bond or a linear alkylene group having 1 to 20 carbon atoms, and even more preferably a single bond or a linear alkylene group having 2 to 10 carbon atoms. In addition, in the spacer group Sp ^AP1 , one or two or more non-adjacent -CH ₂ - groups in the alkylene group may be substituted with -CH═CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO- so that oxygen atoms are not directly adjacent. Note that "substituted with a polymerizable group P ^AP1 " may refer to substitution with only the polymerizable group P ^AP1 , or to substitution with the group P ^AP1 -Sp ^AP1- including the spacer group Sp ^AP1 . The same applies to other polymerizable groups.

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

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

P ^AP1 -Sp ^AP1 - may be bonded to a polymerizable group, a mesogenic group or a polar group, and it is particularly preferred that P ^AP1 -Sp ^AP1 - be bonded to a mesogenic group or a polar group.

When a plurality of P ^AP1s and/or Sp ^AP1s are present in a 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 may play the role of either a donor or an acceptor of protons that mediate hydrogen bonds, or may play both roles.
Preferably, the group contains a polar element having an atomic group in which a carbon atom and a heteroatom are linked. In this specification, the polar element refers to an atomic group in which a carbon atom and a heteroatom are directly linked. 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, even more preferably at least one selected from the group consisting of N and O, and particularly preferably O.

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

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

Although polymerizable groups are excluded from polar groups, the structure in which a hydrogen atom in a polar group is substituted with P ^AP1 -Sp ^AP1 - and the structure in which a hydrogen atom in P ^AP1 -Sp ^AP1 - is substituted with -OH are included in the polar group. P ^AP1 and Sp ^AP1 are as explained above in the section "Polymerizable group".

Polar groups contain one or more polar elements and are broadly classified into cyclic group types and chain group types. Cyclic group types include a cyclic group with a ring structure that contains a polar element within its structure. Chain group types do not include a cyclic group with a ring structure that contains a polar element within its structure, but rather have a polar element within a linear or branched chain group, and may have a ring structure that does not contain a polar element as part of its structure.

A cyclic group-type polar group refers to a structure containing at least one polar element within a cyclic atomic arrangement. Note that, in this specification, the term "cyclic group" is as defined above. Therefore, a cyclic group-type polar group only needs to contain a cyclic group containing a polar element, and the polar group as a whole may be branched or linear.

On the other hand, a chain-type polar group refers to a structure that does not contain a cyclic atomic arrangement containing a polar element within the molecule, but contains at least one polar element within a linear atomic arrangement (which may be branched).

In this specification, a chain group refers to an atomic group in which the constituent atoms are linearly bonded (or may be branched) without containing a cyclic atomic arrangement in the structural formula, and is an acyclic group. In other words, a chain group refers to a linear or branched aliphatic group, and may contain either saturated or unsaturated bonds.

Accordingly, chain-type polar groups include, for example, alkyl groups, alkenyl groups, alkoxy groups, ester groups, ether groups, and ketone groups. The hydrogen atoms in these groups may be substituted with at least one substituent (a reactive functional group (e.g., vinyl group, acrylic group, methacrylic group), or a chain organic group (e.g., alkyl group, cyano group)). Chain-type polar groups may be either linear or branched.

The cyclic polar group is preferably a heteroaromatic group (including fused rings) having 3 to 20 carbon atoms or a heteroalicyclic group (including fused rings) having 3 to 20 carbon atoms, more preferably a heteroaromatic group (including fused rings) having 3 to 12 carbon atoms or a heteroalicyclic group (including fused rings) having 3 to 12 carbon atoms, and even more preferably a 5-membered heteroaromatic group, a 5-membered heteroalicyclic group, a 6-membered heteroaromatic group, or a 6-membered heteroalicyclic group. The hydrogen atoms in these ring structures may be substituted with a halogeno group, a linear or branched alkyl group, or an alkyloxy group having 1 to 5 carbon atoms. The halogeno group is preferably a fluoro group or a chloro group, and more preferably a fluoro group.

The chain-type polar group is preferably a straight-chain or branched alkyl group having 1 to 20 carbon atoms in which hydrogen atoms and -CH _{2 - within the structure are substituted with polar elements. One or two or more non-adjacent -CH 2 -} groups in the alkyl group may be substituted with -CH═CH-, -C≡C-, -O-, -CO-, -COO-, -OCO- or -OCO-COO- so that oxygen atoms are not directly adjacent. Furthermore, the chain-type polar group preferably contains one or two or more polar elements at its end.

One or more hydrogen atoms in the polar group may be substituted with a polymerizable group. Polymerizable groups are as described above in the "Polymerizable Group" section.

Specific examples of polar elements include polar elements containing oxygen atoms (hereinafter referred to as oxygen-containing polar elements), polar elements containing nitrogen atoms (hereinafter referred to as nitrogen-containing polar elements), polar elements containing phosphorus atoms (hereinafter referred to as phosphorus-containing polar elements), polar elements containing boron atoms (hereinafter referred to as boron-containing polar elements), polar elements containing silicon atoms (hereinafter referred to as silicon-containing polar elements), and polar elements containing sulfur atoms (hereinafter referred to as sulfur-containing polar elements). Of these, the polar elements are preferably sulfur-containing polar elements, nitrogen-containing polar elements, or oxygen-containing polar elements, with oxygen-containing polar elements being more preferred. This is because these polar elements have a stronger interaction with the substrate and impurities than other polar elements.

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

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

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

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

The oxygen-containing cyclic group preferably includes any of the following groups that have an oxygen atom as an ether group within the ring structure. In the formulas below, * represents a bond.

Furthermore, the oxygen-containing cyclic group preferably contains any of the following groups that have an oxygen atom in the ring structure as a carbonyl group, carbonate group, or ester group. In the following formulas, * represents a bond.

The nitrogen-containing cyclic group preferably contains one of the following groups. In the formulas below, * represents a bond.

The oxygen-containing chain group preferably contains one of the following groups:

(In the formula, R ^at1 represents an alkyl group having 1 to 5 carbon atoms.
Z ^at1 represents a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms, or a linear or branched alkenylene group having 2 to 18 carbon atoms, provided that one or more —CH ₂ — groups in the alkylene group or alkenylene group may be replaced with —O—, —COO—, —C(═O)—, or —OCO— so that oxygen atoms are not directly adjacent to each other.
X ^at1 represents a hydrogen atom or an alkyl group having 1 to 15 carbon atoms, provided that one or more —CH ₂ — groups in the alkyl group may be substituted with —O—, —COO—, —C(═O)—, or —OCO— so that the oxygen atom is not directly adjacent to the alkyl group.
* in the formula represents a bond.)

The nitrogen-containing chain group preferably contains one of the following groups:

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

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

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

(wherein Sp ^AT1 represents a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, one or more hydrogen atoms in the alkylene group may be substituted with —OH, —CN, —W ^AT1 -Z ^AT1 or P ^AP1 -Sp ^AP1 —, and one or two or more non-adjacent —CH ₂ — groups in the alkylene group may be substituted with a cyclic group, —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO— so that the oxygen atoms are not directly bonded,
^WAT1 is a single bond or the following general formula (WAT1) or (WAT2):

(In the formula, Sp ^WAT1 and Sp ^WAT2 each independently represent a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, one or more hydrogen atoms in the alkylene group may be substituted with —OH, —CN, or P ^AP1 -Sp ^AP1 —, and one or two or more non-adjacent —CH ₂ — groups in the alkylene group may be substituted with a cyclic group, —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—, so that the oxygen atoms are not directly adjacent to each other. * in the formula represents a bond.)
Z ^AT1 represents a monovalent polar group containing a polar element, and one or more hydrogen atoms in Z ^AT1 may be substituted with —OH, —CN, or —P ^AP1 —Sp ^AP1 —.
^PAP1 represents a polymerizable group;
Sp ^AP1 represents a spacer group.
* in the formula represents a bond.)

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

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

In addition, in Sp ^AT1 , Sp ^WAT1 and Sp ^WAT2 , one or two or more non-adjacent —CH ₂ — groups in the alkylene group may each independently be substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO— so that oxygen atoms are not directly bonded.

The hydrogen atoms in Sp ^AT1 and Sp ^WAT1 may each independently be substituted with -W ^AT1 -Z ^AT1 or P ^AP1 -Sp ^AP1 -.

In particular, Sp ^AT1 is preferably a linear or branched alkylene group having 1 to 25 carbon atoms in which at least one hydrogen atom has been substituted with P ^AP1 -Sp ^AP1 -. The polar group Z ^AT1 and the polymerizable group P ^AP1 in the substituent P ^AP1 -Sp ^AP1 - of Sp ^AT1 can be located in close proximity. By having such a structure, the polymerizable compound B can strengthen the interaction with the substrate of the polymer of polymerizable compound B formed at the interface between the liquid crystal layer and the substrate in a liquid crystal display element that does not have an alignment film, thereby increasing the ability of the polymer of polymerizable compound B to control the vertical alignment of liquid crystal molecules. Furthermore, in a liquid crystal display element that has an alignment film, impurities adsorbed and collected by the polar group can be easily incorporated into the polymer, preventing deterioration of the physical properties of the liquid crystal layer due to leakage and diffusion of impurities into the liquid crystal layer.

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

(In the formula, Sp ^ZAT11 represents a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, one or more hydrogen atoms in the alkylene group may be substituted with —OH, —CN, —Z ^ZAT11 -R ^ZAT11 or P ^AP1 -Sp ^AP1 —, and one or two or more non-adjacent —CH ₂ — groups in the alkylene group may be substituted with a cyclic group, —O—, —COO—, —C(═O)—, —OCO— or —CH═CH— so that the oxygen atoms are not directly adjacent to each other.)
Sp ^ZAT12 represents a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, in which one or more hydrogen atoms may be substituted with —OH, —CN or P ^AP1 -Sp ^AP1 —, and one or two or more non-adjacent —CH ₂ — groups in the alkylene group may be substituted with a cyclic group, —O—, —COO—, —C(═O)—, —OCO—, —CH═CH— or —Z ^ZAT11 — so that the oxygen atoms are not directly adjacent to each other.
Z ^ZAT11 represents a polar group containing a polar element.
The ring structure containing Z ^ZAT12 represents a 5- to 7-membered ring.
One or more hydrogen atoms in Z ^ZAT11 and Z ^ZAT12 may be substituted with —OH, —CN or —P ^AP1 —Sp ^AP1 —.
R ^ZAT11 and R ^ZAT12 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, in which one or more hydrogen atoms in the alkyl group may be substituted with —OH, —CN, or P ^AP1 -Sp ^AP1 —, and one or two or more non-adjacent —CH ₂ — groups in the alkyl group may be substituted with a cyclic group, —O—, —COO—, —C(═O)—, —OCO—, —CH═CH—, or —Z ^ZAT11 — so as not to directly bond to the oxygen atom.
^PAP1 represents a polymerizable group;
Sp ^AP1 represents a spacer group.
* in the formula represents a bond.)

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

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

Furthermore, preferred examples of the group represented by general formula (ZAT1-1) include the following groups:

(In the formula, R ^tc represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or P ^AP1 -Sp ^AP1 -, one or more hydrogen atoms in the alkyl group may be substituted with -OH, -CN, or P ^AP1 -Sp ^AP1 -, and one or two or more non-adjacent -CH ₂ - groups in the alkyl group may be substituted with a cyclic group, -O-, -COO-, -C(=O)-, -OCO-, -CH=CH-, or -Z ^ZAT11 - so that the oxygen atoms are not directly adjacent to each other.)
A hydrogen atom in the molecule may be substituted with P ^AP1 -Sp ^AP1 -.
* in the formula represents a bond.

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

(wherein Sp ^ZAT12 has the same meaning as above, and one or more hydrogen atoms bonded to the carbon atom may be substituted with a halogen atom, —OH, —CN, or P ^AP1 —Sp ^AP1 —.)
* in the formula represents a bond.)

[Mesogenic group]
The polymerizable compound B preferably has a mesogenic group. The mesogenic group refers to a group having one or more groups with rigid portions, such as cyclic groups. Here, the term "cyclic group" refers to an atomic group in which constituent atoms are bonded in a ring, and includes carbon rings, hetero rings, saturated or unsaturated cyclic structures, monocyclic structures, bicyclic structures, polycyclic structures, aromatic structures, non-aromatic structures, etc.

It is preferable that the mesogenic group have a skeleton similar to that of a liquid crystal molecule (liquid crystal compound).

The mesogenic group is preferably a group having 2 to 4 cyclic groups, more preferably a group having 3 to 4 cyclic groups. The cyclic groups may be linked by a single bond or by a linking group.

When the cyclic group is a monocyclic group, it is preferable that the mesogenic group contains two or more monocyclic rings.

The cyclic group may contain at least one heteroatom. The cyclic group may also be substituted with at least one substituent. Examples of such substituents include halogen groups, polymerizable groups, and organic groups such as alkyl, alkoxy, and aryl.

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

(wherein ^ZAL1 represents a single bond, —CH═CH—, —CF═CF—, —C≡C—, —COO— _, —OCO—, —OCOO—, —CF 2 O—, —OCF ₂ —, —CH═CHCOO—, —OCOCH═CH—, —CH 2 —CH 2 COO—, —OCOCH ₂ —CH ₂ —, —CH═C(CH ₃ )COO—, —OCOC(CH ₃ )═CH—, —CH ₂ —CH(CH ₃ )COO—, —OCOCH(CH ₃ )—CH ₂ —, —OCH ₂ CH _{2 O—} , or _an alkylene group having 1 to 20 carbon atoms _, The - may be substituted with a cyclic group, -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- so that the oxygen atom is not directly bonded.
A ^AL1 and A ^AL2 each independently represent a divalent cyclic group.
One or more hydrogen atoms in Z ^AL1 , A ^AL1 and A ^AL2 may each independently be substituted with a halogeno group, a polar group, -Sp ^AT1 -W ^AT1 -Z ^AT1 , P ^AP1 -Sp ^AP1 - or a monovalent organic group.
Sp ^AP1 , Sp ^AT1 , P ^AP1 , W ^AT1 and Z ^AT1 have the same meanings as above.
m ^AL1 represents an integer of 1 to 5.
When m ^AL1 represents an integer of 2 to 5, multiple Z ^AL1 's may be the same or different, and multiple A ^AL1 's may be the same or different.
* in the formula represents a bond.)

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

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

In general formula (AL), A ^AL1 and A ^AL2 each independently represent a divalent cyclic group. Examples of the divalent cyclic group include a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a thiophene-2,5-diyl group, a 1,4-bicyclo(2.2.2)octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a fluorocarbon ... It is preferably one selected from the group consisting of a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b']dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b']diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b]selenophene-2,7-diyl group, and a fluorene-2,7-diyl group. Among these, A ^{1 AL1} and A 1 ^AL2 are each independently more preferably a 1,4-phenylene group, a 1,4-cyclohexylene group, a 2,6-naphthylene group or a phenanthrene-2,7-diyl group, and even more preferably a 1,4-phenylene group or a 1,4-cyclohexylene group.

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 halogeno 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 halogeno group include a fluoro group and a chloro group, with a fluoro group being preferred.

In general formula (AL), the monovalent organic group refers to a group whose chemical structure is constituted by an organic compound being in the form of a monovalent group, and refers to an atomic group formed by removing one hydrogen atom from an organic compound. Examples of such monovalent organic groups include alkyl groups having 1 to 15 carbon atoms, alkenyl groups having 2 to 15 carbon atoms, alkoxy groups having 1 to 14 carbon atoms, and alkenyloxy groups having 2 to 15 carbon atoms. One or more -CH ₂ - in the alkyl groups, alkenyl groups, alkoxy groups, and alkenyloxy groups may be substituted with -O-, -COO-, or -OCO-, respectively, so that the oxygen atoms are not directly adjacent to each other.

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

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

Preferred forms of the mesogenic group include structures represented by the following formulas (me-1) to (me-44):

(In formulas (me-1) to (me-44), each of the terminal rings has a bond at the position where one of the hydrogen atoms bonded to the carbon atoms constituting the ring has been removed.)

In the above formulas (me-1) to (me-44), one or more hydrogen atoms in the cyclohexane ring, benzene ring or naphthalene ring may each independently be substituted with a halogeno group, P ^AP1 -Sp ^AP1 -, a monovalent organic group (for example, an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms), or a polar group.

More preferred forms of the mesogenic group are structures represented by formulas (me-8) to (me-44), more preferred forms are structures represented by formulas (me-8) to (me-10), (me-12) to (me-18), (me-22) to (me-24), (me-26) to (me-27), and (me-29) to (me-44), and even more preferred forms are structures represented by formulas (me-12), (me-14), (me-16), (me-22) to (me-24), (me-29), (me-34), (me-36) to (me-37), and (me-42) to (me-44).

Among the above mesogenic groups, particularly preferred are structures represented by the following general formula (AL-1) or (AL-2), and the most preferred 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 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a halogeno group, P ^AP1 -Sp ^AP1 -, or a polar group; provided that one of X ^AL101 , X ^AL102 , X ^AL103 , X ^AL117 , and X ^AL118 represents a bond; one of X ^AL108 , X ^AL109 , X ^AL110 , X ^AL111 , and X ^AL112 represents a bond; one of X ^AL201 , X ^AL202 , X ^AL203 , X ^AL212 , and X ^AL213 represents a bond; and X ^AL206 , X ^AL207 , X ^AL208 , X ^AL209 and X ^AL210 represent a bond.
In addition, one or more of X ^AL101 to X ^AL118 and X ^AL201 to X ^AL214 are substituted with a polar group.
The polar group 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.
General formula (AL-1) or general formula (AL-2) has one or more types of P ^AP1 -Sp ^AP1 - in its molecule.

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

In general formula (AL-1), at least one of X ^AL109 , X ^AL110 and X ^AL111 is preferably a polar group such as P ^AP1 -Sp ^AP1 - or a polar group having a polymerizable moiety within its structure, and it is more preferable that both or one of X ^AL109 and X ^AL111 is P ^AP1 -Sp ^AP1 -.

In general formula (AL-1), it is preferable that one or two of X ^AL104 to X ^AL108 and X ^AL112 to X ^AL116 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogeno group, and more preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom. It is particularly preferable that X ^AL105 , X ^AL106 or X ^AL107 each independently represent an alkyl group having 1 to 3 carbon atoms or a fluorine atom.

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

In general formula (AL-2), at least one of X ^AL207 , X ^AL208 and X ^AL209 is preferably a polar group having P ^AP1 -Sp ^AP1 - among polar groups or a polar group having a polymerizable moiety within the structure, and it is more preferable that both or one of X ^AL207 and X ^AL209 is P ^AP1 -Sp ^AP1 -.

In general formula (AL-2), it is preferable that one or two of X ^AL202 to X ^AL206 and X ^AL210 to X ^AL214 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogeno group, more preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom. It is particularly preferable that X ^AL204 , X ^AL205 or X ^AL206 each independently represent an alkyl group having 1 to 3 carbon atoms or a fluorine atom.

[Specific embodiment of polymerizable compound B]
The polymerizable compound B has one or more polar groups, one or more polymerizable groups, and a mesogenic group, and it is preferable that the polymerizable group is substituted on the mesogenic group or the polar group directly or via a spacer group. In particular, it is preferable that the polymerizable group is incorporated into the polar group and is substituted on the mesogenic group.

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

Polymerizable compound B preferably has a form in which the polar element contained in the polar group or the polar element contained in the polymerizable group is localized. The proximity of the polar group and the polymerizable group enhances interaction with the substrate and impurities, and also allows for good solubility in the liquid crystal composition. Specifically, polymerizable compound B preferably has a form in which a polymerizable group and a polar group are on the same ring. Such forms include a form in which one or more polymerizable groups and one or more polar groups are bonded to the same ring, and a form in which one of at least one of one or more polymerizable groups or at least one of one or more polar groups is bonded to the other, resulting in a polymerizable group and a polar group on the same ring.

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

(In the formula, R ^AK1 represents a linear or branched alkyl group having 1 to 20 carbon atoms, one or two or more non-adjacent —CH ₂ — groups in the alkyl group may be substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO— so that oxygen atoms are not directly bonded, and one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.)
A ^AL1 and A ^AL2 each independently represent the same meaning as A ^AL1 and A ^AL2 in formula (AL).
Z ^AL1 has the same meaning as Z ^AL1 in formula (AL).
m ^AL1 has the same meaning as m ^AL1 in formula (AL).
Sp ^AT1 has the same meaning as Sp ^AT1 in formula (AT).
W ^AT1 has the same meaning as W ^AT1 in formula (AT).
Z ^AT1 has the same meaning as Z ^AT1 in formula (AT).
^PAP1 represents a polymerizable group.
Sp ^AP1 represents a spacer group.
When a plurality of R ^AK1 , A ^AL1 , A ^AL2 , Z ^AL1 , Z ^AT1 , Sp ^AT1 , W ^AT1 , P ^AP1 , and Sp ^AP1 are present in the formula, they may be the same or different.

R ^AK1 preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms, more preferably a linear alkyl group having 1 to 20 carbon atoms, and even more preferably a linear alkyl group having 1 to 8 carbon atoms. One or two or more non-adjacent -CH ₂ - groups in the alkyl group may each independently be substituted with -CH═CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO- so as not to be directly adjacent to an oxygen atom. Furthermore, one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom. As the halogen atom, a fluorine atom or a chlorine atom is preferred, and a fluorine atom is more preferred.

Details of A ^AL1 , A ^AL2 , Z ^AL1 , Z ^AT1 , Sp ^AT1 , W ^AT1 , P ^AP1 and Sp ^AP1 are as described above.

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

Preferable lower limits for the content of polymerizable compound B are 0.01 mass%, 0.03 mass%, 0.05 mass%, 0.08 mass%, 0.1 mass%, 0.15 mass%, 0.2 mass%, 0.25 mass%, and 0.3 mass% relative to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention. Preferable upper limits for the content of polymerizable compound B are 10 mass%, 8 mass%, 5 mass%, 3 mass%, 1.5 mass%, 1.2 mass%, 1 mass%, 0.8 mass%, and 0.5 mass% relative to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention.

If the content of polymerizable compound B in the polymerizable compound-containing liquid crystal composition of the present invention is low, the effects of adding polymerizable compound B will be less apparent. On the other hand, if the content is too high, problems will arise, such as a large amount remaining after curing, long curing times, and reduced reliability of the liquid crystal. For this reason, it is preferable to set the content by combining the above-mentioned upper and lower limits while taking these factors into consideration.

Specific ranges for the content of polymerizable compound B are, for example, preferably within the range of 0.05% by mass to 10% by mass, preferably within the range of 0.1% by mass to 8% by mass, preferably within the range of 0.1% by mass to 5% by mass, preferably within the range of 0.1% by mass to 3% by mass, preferably within the range of 0.2% by mass to 2% by mass, preferably within the range of 0.2% by mass to 1.3% by mass, preferably within the range of 0.2% by mass to 1% by mass, and preferably within the range of 0.2% by mass to 0.56% by mass, relative to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention.

[2-3] Other Details Regarding Polymerizable Compound 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 A and one or more polymerizable compounds B.

In particular, 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. This is because the inclusion of both polymerizable compounds A and B provides a higher suppression effect on the decrease in VHR due to UV irradiation than when each polymerizable compound is contained alone, and enables the achievement of higher tilt stability.

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

Preferable lower limits for the content of the polymerizable compound are 0.01% by mass, 0.02% by mass, 0.03% by mass, 0.05% by mass, 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, based on the total amount of the polymerizable compound-containing liquid crystal composition of the present invention.

Furthermore, preferred upper limits of the content of the polymerizable compound are 10% by mass, 8% by mass, 5% by mass, 3% by mass, 1.5% by mass, 1.2% by mass, 1% by mass, 0.8% by mass, 0.6% by mass, and 0.5% by mass, based on the total amount of the polymerizable compound-containing liquid crystal composition of the present invention.

[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 General Formula (L).

(wherein R ^L1 and R ^L2 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — groups in the alkyl group may each independently be replaced by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—;
n ^L1 represents 0, 1, 2 or 3;
A ^L1 , A ^L2 and A ^L3 each independently represent (a) a 1,4-cyclohexylene group (in which one —CH ₂ — or two or more non-adjacent —CH ₂ — groups may be replaced by —O—).
(b) a 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= groups in this group may be replaced by -N=), and (c) a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= groups in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N=).
wherein the groups (a), (b) and (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom;
Z ^L1 and Z ^L2 each independently 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 a plurality of A ^L2s are present, they may be the same or different; when n ^L1 is 2 or 3 and a plurality of Z ^L2s are present, they may be the same or different.
However, compounds represented by general formula (i) are excluded.

Compounds represented by general formula (L) are nearly dielectrically neutral compounds (Δε value of -2 to 2). For this reason, the number of polar groups such as halogens present in the molecule is preferably 2 or less, more preferably 1 or less, and preferably none. Furthermore, the number of halogen atoms present in the molecule is preferably 0, 1, 2, or 3, with 0 or 1 being preferred, and 1 being preferred when compatibility with other liquid crystal molecules is important.

Compounds represented by general formula (L) may be used alone or in combination. There are no particular restrictions on the types of compounds that can be combined, and appropriate combinations are used depending on the desired performance, such as solubility at low temperatures, transition temperature, electrical reliability, and birefringence. In one embodiment of the present invention, for example, one type of compound is used. Alternatively, in another embodiment of the present invention, two, three, four, five, six, seven, eight, nine, or ten or more types of compounds are used.

The content of the compound represented by general formula (L) can be adjusted appropriately depending on the desired performance, such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, process compatibility, drop marks, image sticking, and dielectric anisotropy.

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

In the case where the liquid crystal composition of the present invention is required to maintain a low viscosity and have a fast response speed, it is preferable that the content of the compound represented by general formula (L) has a high lower limit and a high upper limit. In the case where the liquid crystal composition of the present invention is required to maintain a high _Tni and have good temperature stability, it is preferable that the content of the compound represented by general formula (L) has a high lower limit and a high upper limit. In the case where it is desired to increase the dielectric anisotropy in order to maintain a low driving voltage, it is preferable that the content of the compound represented by general formula (L) has a low lower limit and a low upper limit.

In the above general formula (L), R ^L1 and R ^L2 each independently represent an alkyl group having 1 to 8 carbon atoms. One or two or more non-adjacent -CH ₂ - groups in the alkyl group may each independently be substituted by -CH═CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO-. Of these, it is preferable that R ^L1 and R ^L2 each independently 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.

More specifically, when reliability is emphasized, it is preferable that both R ^L1 and R ^L2 are alkyl groups having 1 to 8 carbon atoms. Furthermore, when reducing the volatility of the compound is emphasized, it is preferable that both R ^L1 and R ^L2 are alkoxy groups having 1 to 8 carbon atoms. Furthermore, when reducing viscosity is emphasized, 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 each a phenylene group (aromatic), R ^L1 and R ^L2 each preferably represent a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms. On the other hand, when the ring structures (A ^L1 and A ^L3 ) to which R ^L1 and R ^L2 are bonded are each saturated ring structures such as cyclohexylene, pyran, and dioxane, R ^L1 and R ^L2 each preferably represent a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, it is preferable that the total number of carbon atoms and oxygen atoms in R ^L1 and R ^L2 is 5 or less, and they are preferably linear.

In the above general formula (L), n ^L1 is preferably 0 when emphasis is placed on response speed, preferably 2 or 3 in order to improve the maximum temperature of the nematic phase, and preferably 1 in order to strike a balance between these. In addition, in order to satisfy the properties required of the composition, it is preferable to combine compounds having different values of n ^L1 .

In the general formula (L), A ^L1 , A ^L2 and A ^L3 are preferably aromatic when it is required to increase Δn, and are preferably aliphatic to improve the response speed. ^{A L1} , A ^L2 and A ^L3 each independently preferably represent a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably represent the following structure:

It is particularly preferred that the group represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.

In the above general formula (L), when emphasis is placed on response speed, it is preferable that Z ^{1 L1} and Z ^{1 L2} each be a single bond.

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

In formula (La), R ^L1a and R ^L2a each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — groups in the alkyl group may each independently be replaced by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
at least one of R ^L1a and R ^L2a is an alkenyl group having 2 to 8 carbon atoms;
A ^L1a , A ^L2a , A ^L3a , Z ^L1a , Z ^L2a and n ^L1a have the same definitions as A ^L1 , A ^L2 , A ^L3 , Z ^L1 , Z ^L2 and n ^L1 in formula (L), respectively.

While compounds represented by general formula (L-a) can increase the response speed of liquid crystal display elements, they are susceptible to degradation by UV irradiation during polymerization of the polymerizable compound, and the voltage holding ratio (VHR) of the liquid crystal display element is likely to decrease. In contrast, the polymerizable compound-containing liquid crystal composition of the present invention, which contains a compound represented by general formula (i) in addition to the polymerizable compound, can shorten the UV irradiation time required for the polymerization reaction of the polymerizable compound, thereby improving the effect of suppressing degradation of the compound represented by general formula (L-a) and the decrease in voltage holding ratio (VHR).

Therefore, by including a compound represented by general formula (La) in addition to the compound represented by general formula (i) and the polymerizable compound, the polymerizable compound-containing liquid crystal composition of the present invention makes it possible to produce a liquid crystal display device that achieves an even higher compatibility between high-speed response and high VHR.

In the compound represented by general formula (La), either R or ^R may represent an alkenyl group, or both R and ^R may represent alkenyl groups. The alkenyl group may have 2 to 8 carbon atoms, preferably 2, ³ , 4, or 5, and more preferably 2 or ³ .

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

The compound represented by general formula (L) is preferably a compound selected from the group of compounds represented by general formulas (NU-01) to (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 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms.)

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

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

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

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

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

(In the above formulas, R ^NU12a , R ^NU22a , R ^NU32a , R ^NU42a , and R ^NU52a each independently represent an alkyl group having 1 to 8 carbon atoms;
one or two or more non-adjacent —CH ₂ — groups in the alkyl group may be substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—, as long as oxygen atoms are not adjacent to each other;
One or more hydrogen atoms in the alkyl group may be substituted with a halogen atom;
n1 to n5 each independently represent an integer of 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 a compound represented by general formula (NU-01), a compound represented by general formula (NU-02), a compound represented by general formula (NU-03), and a compound represented by general formula (NU-05).

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

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

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

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

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

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

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

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

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

(In the formula, R ^N11 and R ^N12 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — groups in the alkyl group may each independently be replaced by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—;
A ^N11 and A ^N12 each independently represent (a) a 1,4-cyclohexylene group (in which one —CH ₂ — or two or more non-adjacent —CH ₂ — groups may be replaced by —O—).
(b) a 1,4-phenylene group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=).
(c) a group selected from the group consisting of a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one —CH= or two or more non-adjacent —CH= groups present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by —N=), and (d) a 1,4-cyclohexenylene group, wherein the groups (a), (b), (c), and (d) each independently may be substituted by a cyano group, a fluorine atom, or a chlorine atom,
Z ^N11 and Z ^N12 each independently 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—;
n ^N11 and n ^N12 each independently represent an integer of 0 to 3, provided that n ^N11 +n ^N12 is 1, 2 or 3, and when a plurality of A ^N11 to A ^N12 and Z ^N11 to Z ^N12 are present, they may be the same or different.
However, compounds represented by general formula (i) and general formula (L) are excluded.

The compound represented by general formula (N-1) is a dielectrically negative compound (the sign of Δε is negative and its absolute value is greater than 2). Of these, the compound represented by general formula (N-1) is preferably a compound with a negative Δε and an absolute value of greater than 3.

In general formula (N-1), R ^N11 and R ^N12 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent -CH ₂ - groups in the alkyl group may each independently be replaced by -CH═CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO-. Among these, R ^N11 and R ^N12 each independently represent preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and particularly preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms.

Furthermore, when the ring structure to which R ^N11 and R ^N12 are bonded is a phenyl group (aromatic), they are preferably a linear alkyl group of 1 to 5 carbon atoms, a linear alkoxy group of 1 to 4 carbon atoms, or an alkenyl group of 4 to 5 carbon atoms. When the ring structure to which R ^N11 and R ^N12 are bonded is a saturated ring structure such as cyclohexane, pyran, or dioxane, they are preferably a linear alkyl group of 1 to 5 carbon atoms, a linear alkoxy group of 1 to 4 carbon atoms, or a linear alkenyl group of 2 to 5 carbon atoms. In order to stabilize the nematic phase, it is preferable that the total number of carbon atoms and, if present, oxygen atoms in R ^N11 and R ^N12 be 5 or less, and they are preferably linear.

The alkenyl group is preferably selected from groups represented by formulas (R1) to (R5).

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

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

The above groups (a), (b), (c), and (d) may each independently be substituted with a cyano group, a fluorine atom, or a chlorine atom.

A ^N11 and A ^N12 are each independently preferably aromatic when it is required to increase Δn, and are preferably aliphatic in order to improve the response speed. The above groups (a), (b), (c) and (d) preferably represent a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, a 2,3-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably represent the following structure:

It is particularly preferred that the group represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group, or a 1,4-phenylene group.

In general formula (N-1), Z ^N11 and Z ^N12 each independently 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—, preferably —CH ₂ O—, —CF ₂ O—, —CH ₂ CH ₂ —, —CF ₂ CF ₂ — or a single bond, more preferably —CH ₂ O—, —CH ₂ CH ₂ — or a single bond, and particularly preferably —CH ₂ O— or a single bond.

In general formula (N-1), n ^N11 and n ^N12 each independently represent an integer of 0 to 3. Furthermore, n ^N11 +n ^N12 each independently represent 1, 2, or 3. Among these, n ^N11 +n ^N12 is preferably 1 or 2, and in this case, combinations in which n ^N11 is 1 and n ^N12 is 0, combinations in which n ^N11 is 2 and n ^N12 is 0, combinations in which n ^N11 is 1 and n ^N12 is 1, and combinations in which n ^N11 is 2 and n ^N12 is 1 are preferred.

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

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

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

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

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

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

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

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

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

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, as the compound represented by general formula (N-01), one or more compounds selected from the group of compounds represented by general formulas (N-01-1) to (N-01-4).

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

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

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

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

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

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

In the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by general formula (N-01) in the total amount is 0% by mass, 1% by mass, 5% 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, or 80% by mass, and the preferred upper limit of the 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, or 10% by mass.

In the total amount of the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by general formula (N-02) is 0% by mass, 1% by mass, 5% 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, or 80% by mass, and the preferred upper limit of the 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, or 10% by mass.

In the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by general formula (N-03) in the total amount is 0% by mass, 1% by mass, 5% 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, or 80% by mass, and the preferred upper limit of the 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, or 10% by mass.

In the total amount of the liquid crystal composition of the present invention, the preferred lower limit of the content of the compound represented by general formula (N-04) is 0% by mass, 1% by mass, 5% 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, or 80% by mass, and the preferred upper limit of the 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, or 10% by mass.

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

[5] Other Compounds The polymerizable compound-containing liquid crystal composition of the present invention may contain one or more compounds having positive dielectric anisotropy described in paragraphs 0236 to 0509 of Japanese 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 are bonded together, such as a peroxy acid (-CO-OO-) structure, within the molecule. When the reliability and long-term stability of the liquid crystal composition are important, the content of compounds having carbonyl groups is preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 1% by mass or less, relative to the total mass of the composition, and most preferably substantially none.

When stability against UV irradiation is important, the content of chlorine-substituted compounds in the polymerizable compound-containing liquid crystal composition of the present invention is preferably 15% by mass or less, more 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 even more preferably substantially none, relative to the total mass of the composition.

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains a large amount of compounds whose intramolecular ring structures are all six-membered rings, and the content of compounds whose intramolecular ring structures are all six-membered rings is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, relative to the total mass of the composition. It is most preferable that the composition be composed essentially of compounds whose intramolecular ring structures are all six-membered rings.

In order to suppress deterioration of the liquid crystal composition due to oxidation, it is preferable that the polymerizable compound-containing liquid crystal composition of the present invention has a low content of compounds having a cyclohexenylene group as a ring structure, and the content of compounds having a cyclohexenylene group 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 even more preferably substantially none, relative to the total mass of the composition.

When importance is attached to improving the viscosity and improving _Tni , the polymerizable compound-containing liquid crystal composition of the present invention preferably has a small content of a compound having a 2-methylbenzene-1,4-diyl group in the molecule in which a hydrogen atom may be substituted with a halogen, and the content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is preferably 10% by mass or less, more preferably 8% by mass or less, more preferably 5% by mass or less, and more preferably 3% by mass or less, of the total amount of the liquid crystal composition of the present invention, and further preferably is substantially free of the compound.

In this specification, "substantially not contained" means not contained except for those that are unintentionally contained.

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

[6] Additives The polymerizable compound-containing liquid crystal composition of the present invention may contain an antioxidant, an ultraviolet absorber, a light stabilizer, an infrared absorber, etc. In particular, the polymerizable compound-containing liquid crystal composition of the present invention preferably contains an antioxidant so as to prevent polymerization during heat treatment, which is one of the processes for producing a liquid crystal display element.

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

In general formulas (H-1) to (H-3), R ^H1 each independently represents an alkyl group having 3 to 7 carbon atoms. More specifically, R ^H1 in general formula (H-1) represents an alkyl group having 7 carbon atoms. R ^H1 in general formula (H-2) represents an alkyl group having 3 carbon atoms. R ^H1 in general formula (H-3) represents an alkyl group having 3 carbon atoms.

In general formula (H-4), M ^H1 represents an alkylene group having 4 to 10 carbon atoms (one or more —CH ₂ — in the alkylene group may be replaced by —COO— or —OCO— so that the oxygen atom is not directly adjacent), a single bond, a 1,4-phenylene group (any hydrogen atom in the 1,4-phenylene group may be replaced by a fluorine atom), or a trans-1,4-cyclohexylene group, and M ^H1 is preferably an alkylene group having 4 to 8 carbon atoms.

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

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

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

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

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

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

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

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

The polymerizable compound-containing liquid crystal composition of the present invention comprises a compound represented by general formula (i-1-1), a polymerizable compound A represented by general formula (P), a polymerizable compound B represented by general formula (SAL), a compound selected from the group of compounds represented by general formulas (N-01-1), (N-01-3), (N-01-4), (N-02-1), (N-03-1), and (N-04-1), and a compound selected from the group of compounds represented by general formulas (NU-01), (NU-02), (NU-03), and The upper limit of the proportion of the component consisting only of a compound selected from the group of compounds represented by (NU-05) and (NU-06) is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, or 84 mass% of the total amount of the polymerizable compound-containing liquid crystal composition of the present invention. The lower limit of the proportion is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, or 99 mass% of the total amount of the polymerizable compound-containing liquid crystal composition of the present invention.

The polymerizable compound-containing liquid crystal composition of the present invention and the liquid crystal composition of the present invention have a nematic phase-isotropic liquid phase transition temperature (T _ni ) of 60° C. to 120° C., more preferably 70° C. to 100° C., and particularly preferably 70° C. to 85° C. In the present invention, a T _ni of 60° C. or higher is expressed as being high.

For liquid crystal television applications, T _ni is preferably 70 to 80°C, for mobile applications, T _ni is preferably 80 to 90°C, and for outdoor display applications such as PID (Public Information Display), T _ni is preferably 90 to 110°C.

The polymerizable compound-containing liquid crystal composition of the present invention and the liquid crystal composition of the present invention have a refractive index anisotropy (Δn) at 20°C of 0.08 to 0.14, more preferably 0.09 to 0.13, and particularly preferably 0.09 to 0.12. More specifically, when used in conjunction with a narrow cell gap, the refractive index anisotropy is preferably 0.10 to 0.13, and when used in conjunction with a wide cell gap, the refractive index anisotropy is preferably 0.08 to 0.10. It is particularly preferred that the liquid crystal composition of the present invention have a refractive index anisotropy (Δn) at 20°C of 0.098 to 0.118.

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

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

B. Liquid Crystal Display Element Next, the liquid crystal display element of the present invention 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 above in the section "A. Polymerizable Compound-Containing Liquid Crystal Composition." That is, the liquid crystal display element of the present invention is a liquid crystal display element using a polymerizable compound-containing liquid crystal composition containing one or more compounds represented by general formula (i) and one or more polymerizable compounds, wherein the total content of the compounds represented by general formula (i) is within a predetermined range.

By using the polymerizable compound-containing liquid crystal composition described above, the liquid crystal display element of the present invention can achieve a sufficiently large tilt angle, with a small amount of polymerizable compound remaining in the liquid crystal display element after polymerization. This eliminates or significantly reduces display defects such as image retention (IS) in high-resolution PSA mode liquid crystal display elements such as 4K and 8K resolutions. Furthermore, in the manufacture of high-resolution PSA mode liquid crystal display elements such as 4K and 8K resolutions, prolonged UV exposure can result in a decrease in VHR due to degradation of the liquid crystal composition and a significant decrease in production efficiency. However, because the liquid crystal display element of the present invention uses the polymerizable compound-containing liquid crystal composition described above, it can be produced as a high-resolution PSA mode liquid crystal display element with a short UV exposure time, making it highly useful industrially.

The liquid crystal display element of the present invention is particularly useful as an active matrix drive liquid crystal display element. Furthermore, the liquid crystal display element of the present invention can be suitably used as a liquid crystal display element driven in PSA mode, PSVA mode, VA mode, PS-IPS mode, or PS-FFS mode, and is particularly suitable for use as a PSA mode or PSVA mode liquid crystal display element.

The liquid crystal display element of the present invention can have a general-purpose structure, for example, including a first substrate and a second substrate arranged opposite each other, a common electrode provided on the first substrate or the second substrate, pixel electrodes having thin-film transistors provided on the first substrate or the second substrate, 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 a compound represented by general formula (i), a liquid crystal composition contained in a polymerizable compound-containing liquid crystal composition, and a polymer of the polymerizable compound.

The liquid crystal display element of the present invention can have an alignment film on the surface of the first substrate facing the liquid crystal layer and on the surface of the second substrate facing the liquid crystal layer.

The liquid crystal display element of the present invention may have an alignment film on each of the liquid crystal layer-side surface of the first substrate and the liquid crystal layer-side surface of the second substrate. The alignment film is a component that contacts the liquid crystal layer and functions to align the liquid crystal molecules contained in the liquid crystal layer. In this case, the polymerizable compound-containing liquid crystal composition used in manufacturing 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, the polymer of polymerizable compound A and/or polymerizable compound B is unevenly distributed at the interface of the liquid crystal layer facing the first substrate and the interface of the liquid crystal layer facing the second substrate, respectively, thereby imparting a pretilt angle to the liquid crystal molecules through the polymer of polymerizable compound A and/or the polymer of polymerizable compound B. Furthermore, when the liquid crystal display element contains a polymer of polymerizable compound B, impurities present in the liquid crystal layer or the alignment film are adsorbed and captured by the polar groups of the polymerizable compound B and incorporated into the polymer of polymerizable compound B. This suppresses a decrease in VHR due to the presence of impurities, thereby achieving high reliability.

The alignment film can be a known alignment film such as a rubbed alignment film or a photo-aligned film. Furthermore, the alignment film can be selected appropriately, such as a vertical alignment film or a horizontal alignment film, depending on the drive mode of the liquid crystal display element. The material constituting the alignment film can be the same as the materials for known alignment films, such as polyimide, polyamide, polysiloxane, and mixtures thereof. Of these, polyimide is preferred. The polyimide may be a photo-crosslinked polyimide or a decomposable polyimide. The thickness of the alignment film can be a thickness commonly used in liquid crystal display elements.

The liquid crystal display element of the present invention may not have an alignment film on at least one of the first and second substrates. That is, the liquid crystal display element of the present invention may be an element of a mode commonly known as PI-less. In this case, the polymerizable compound-containing liquid crystal composition used in the manufacture of the liquid crystal display element of the present invention preferably contains at least polymerizable compound B. Polymerizable compound B becomes a polymer and is unevenly distributed at the interface of the liquid crystal layer facing the first substrate and the interface of the liquid crystal layer facing the second substrate. The polar groups of the polymer of polymerizable compound B interact with the substrate surfaces, enabling the liquid crystal display element of the present invention to vertically align liquid crystal molecules in the liquid crystal layer even without an alignment film.

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

The liquid crystal display element of the present invention has a common electrode on one of the first substrate and the second substrate, and pixel electrodes on the other. The common electrode and pixel electrodes are disposed on the liquid crystal layer side of each substrate. Preferably, the common electrode is disposed on the substrate that includes a color filter, and the pixel electrodes are disposed on the substrate that does not include a color filter. The pixel electrodes include active elements such as TFTs, thin-film diodes, and metal-insulator-metal resistive elements. The common electrode and pixel electrodes can be formed from materials commonly used for electrodes in liquid crystal display elements. Among these, it is preferable that at least the common electrode be formed from a transparent conductor, and it is more preferable that both the common electrode and the pixel electrodes be formed from transparent conductors. Examples of transparent conductors include oxide semiconductors such as indium-doped tin oxide (ITO), zinc oxide (ZnO), tin oxide (SnO ₂ ), InGaZnO, SiGe, GaAs, IZO (indium zinc oxide), TiO, and AZTO (AlZnSnO).

The shapes of the common electrode and pixel electrodes can be selected according to the drive method of the liquid crystal display element. In particular, when the liquid crystal display element of the present invention is active matrix driven, it is preferable that one of the first and second substrates is provided with a full-surface common electrode made of a transparent conductor, and the other substrate has gate electrodes and source electrodes arranged in a matrix, with TFT elements and pixel electrodes provided in the areas surrounded by the gate electrodes and source electrodes.

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

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

The liquid crystal display element of the present invention may have spacers between the first and second substrates to adjust the distance between the first and second substrates, i.e., the thickness of the liquid crystal layer. Examples of spacers include glass particles, plastic particles, alumina particles, and photoresist materials.

The liquid crystal display element of the present invention may have a polarizing plate. If a polarizing plate is used, it is preferable to adjust the product of the refractive index anisotropy Δn of the liquid crystal composition and the cell thickness d so as to maximize the contrast. Furthermore, if two polarizing plates are used, the polarization axes of each polarizing plate can be adjusted to improve the viewing angle and contrast. Furthermore, a retardation film can also be used to widen the viewing angle.

In the liquid crystal display element of the present invention, the first substrate and the second substrate may be fixed with a sealant. Examples of sealants include epoxy-based thermosetting compositions.

The liquid crystal display element of the present invention can be manufactured by known methods. The following example shows a method for manufacturing the liquid crystal display element of the present invention. First, the surface of the first substrate on which the alignment film is arranged and the surface of the second substrate on which the alignment film is arranged are placed opposite each other, and the two substrates are bonded together via a spacer and a sealant to achieve the desired cell gap, to prepare an empty cell. Next, the polymerizable compound-containing liquid crystal composition of the present invention is sandwiched between the first and second substrates of the empty cell using a vacuum injection method, an optical dispersion method (ODF) method, or the like, and the sealant is cured to seal the liquid crystal composition 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.) used to polymerize the polymerizable compound can be set as appropriate.

The present invention is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any configuration that is substantially identical to the technical concept described in the claims of the present invention and that provides similar effects is within the technical scope of the present invention.

The present invention will be described in further detail below with reference to examples, but the present invention is not limited to these examples.

The following abbreviations are used to describe compounds in the following examples and comparative examples.

(Side chain)
-n -C _n H _2n+1 Straight-chain alkyl group with n carbon atoms n- C _n H _2n+1 - Straight-chain alkyl group with n carbon atoms -On -OC _n H _2n+1 Straight-chain alkoxy group with n carbon atoms V- CH ₂ ═CH-
1V- CH ₃ -CH=CH-
-V-CH= _CH2
-V1 -CH=CH-CH ₃
(linking group)
-1O- -CH ₂ -O-
-2- -CH ₂ -CH ₂ -
(ring structure)

The properties 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: Dielectric anisotropy at 20° C. The manufacturing methods and evaluation methods for the liquid crystal display elements in the following examples and comparative examples are as follows.

(Method for manufacturing liquid crystal display element)
First, a liquid crystal composition containing a polymerizable compound (described below) was injected by vacuum injection into a liquid crystal cell with a cell gap of 3.5 μm, which included an ITO substrate coated with a polyimide alignment film that induces vertical alignment and then rubbed. The liquid crystal cell containing the polymerizable compound was then irradiated with ultraviolet light using a fluorescent UV lamp for a desired period of time to obtain a liquid crystal display device. The fluorescent UV lamp was adjusted so that the illuminance measured at a center wavelength of 313 nm was 3 mW/ ^cm² .

(Method for evaluating the amount of residual polymerizable compound)
The residual amount of polymerizable compound (ppm) in the liquid crystal display element after 15, 30, 45, 60, 75, 90, and 115 minutes of UV irradiation under the above-described irradiation conditions was measured using the following method. First, the disassembled liquid crystal display element and acetonitrile were placed in a test tube, shaken, and filtered to obtain an acetonitrile solution containing the eluted components, including the liquid crystal composition, polymer, and unreacted polymerizable compound. This was analyzed using a high-performance liquid chromatograph (column: reversed-phase nonpolar column, eluent: a mixed solvent of 70% acetonitrile by volume and 30% water by volume), and the peak area of each component was calculated. The amount of remaining polymerizable compound was determined from the ratio of the peak area of the liquid crystal compound used as an index to the peak area of the unreacted polymerizable compound. The residual amount of polymerizable compound was determined from this value and the amount of polymerizable compound initially added. The detection limit for the residual amount of polymerizable compound was 200 ppm. The UV irradiation time at which the residual amount of polymerizable compound fell below the lower detection limit was defined as T _ND (minutes).

(Method for evaluating pretilt angle change (tilt imparting ability))
The pretilt angle change [°] of the liquid crystal display element before and after 200 seconds of UV irradiation under the above-mentioned irradiation conditions was measured by the following method. First, the pretilt angle of the liquid crystal display element was measured and defined as the pretilt angle (initial). This liquid crystal display element was irradiated with UV light for 200 seconds while applying a voltage of 10 V at a frequency of 100 Hz. The pretilt angle was then measured and defined as the pretilt angle (post-UV). The pretilt angle change [°] was determined by subtracting the pretilt angle (post-UV) from the measured pretilt angle (initial). The pretilt angle was measured using an OPTIPRO manufactured by Shintech. A larger value of the pretilt angle change [°] indicates higher tilt-imparting ability.

(VHR evaluation method)
A liquid crystal cell filled with a polymerizable compound-containing liquid crystal composition was irradiated with UV for T _ND [minutes] under the above-mentioned irradiation conditions, and VHR was measured under the conditions of 1 V, 0.6 Hz, and 60°C.

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

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

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

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

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

Example 2 was a polymerizable compound-containing liquid crystal composition prepared by adding 99 parts by mass of liquid crystal composition LC-001, 1 part by mass of a compound represented by formula (i-1-1-1A) as the formula (i) compound, and 0.3 parts by mass of polymerizable compound A represented by formula (RM-A1) as the polymerizable compound.

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

For 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] at which the residual amount of the polymerizable compound becomes below the lower detection limit, the VHR [%] after T _ND UV irradiation, and the pretilt angle change [°] after 200 seconds of UV irradiation are each as shown in Table 2 below. The content (% by mass) of the compound of formula (i) in the total amount of the polymerizable compound-containing liquid crystal composition is a value calculated by {parts by mass of the compound of formula (i)/(parts by mass of the liquid crystal composition+parts by mass of the compound of formula (i)+parts by mass of the polymerizable compounds (A and B))}×100, the same applies hereinafter.

As can be seen from Table 2, the VHR [%] after UV _TND irradiation was all sufficiently high, but the UV irradiation time _TND [min] at which the residual amount of polymerizable compound became below the lower detection limit was shorter in Comparative Examples 2-3 and Examples 1-2 than in Comparative Example 1. Furthermore, the pretilt angle change [°] after 200 seconds of UV irradiation was greater in Comparative Examples 2-3 than in Comparative Example 1, but even greater in Examples 1-3 than in Comparative Examples 1-3, demonstrating that Examples 1-3 can form a larger pretilt angle with shorter UV irradiation times than Comparative Examples 1-3. Furthermore, for the liquid crystal display elements after UV _TND irradiation, evaluation of display defects (burn-in) was performed using an OPTIPRO manufactured by Shintech, based on the change in pretilt angle before and after 3 hours of backlight irradiation while applying a voltage of 30 V at a frequency of 100 Hz. Examples 1-3 exhibited high tilt stability.

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

Comparative Example 5 was a polymerizable compound-containing liquid crystal composition prepared by adding 97 parts by mass of liquid crystal composition LC-002, 3 parts by mass of a compound represented by formula (i-1-1-1A) as the formula (i) compound, and 0.3 parts by mass of polymerizable compound A represented by formula (RM-A1) as the polymerizable compound.

Example 4 was a polymerizable compound-containing liquid crystal composition prepared by adding 99 parts by mass of liquid crystal composition LC-002, 1 part by mass of a compound represented by formula (i-1-1-1A) as the formula (i) compound, and 0.3 parts by mass of polymerizable compound A represented by formula (RM-A1) as the polymerizable compound.

A polymerizable compound-containing liquid crystal composition was prepared by adding 0.5 parts by mass of a compound represented by formula (i-1-1-1A) as the formula (i) compound and 0.3 parts by mass of polymerizable compound A represented by formula (RM-A1) as the polymerizable compound to 99.5 parts by mass of liquid crystal composition LC-002, and the resulting composition was designated Example 4-2.

For the polymerizable compound-containing liquid crystal compositions of Comparative Examples 4 and 5 and Examples 4 and 4-2, the UV irradiation time _TND [min] at which the residual amount of the polymerizable compound became less than the lower detection limit, the VHR [%] after _TND UV irradiation, and the pretilt angle change [°] after 200 seconds of UV irradiation were as shown in Table 3 below.

As shown in Table 3, the UV irradiation time _TND [minutes] at which the residual amount of polymerizable compound became below the lower detection limit was shorter in Comparative Example 5 and Example 4 than in Comparative Example 4. The VHR [%] after UV _TND irradiation was significantly higher in Comparative Example 5 and Example 4 than in Comparative Example 4. Furthermore, the pretilt angle change [°] after 200 seconds of UV irradiation was greater in Comparative Example 5 than in Comparative Example 4, but Example 4 showed an even greater value, demonstrating that a pretilt angle could be formed with shorter UV irradiation times than in Comparative Examples 4 and 5. Furthermore, for the liquid crystal display element after UV _TND irradiation, a display defect (burn-in) was evaluated based on the change in pretilt angle before and after 3 hours of backlight irradiation while applying a voltage of 30 V at a frequency of 100 Hz using an OPTIPRO manufactured by Shintech. Example 4 showed high tilt stability.

Moreover, Example 4-2 had a shorter _TND and a higher VHR than Comparative Example 4, and a larger change in pretilt angle than Comparative Example 5.

Furthermore, liquid crystal composition LC-002 contains an alkenyl compound represented by "3-Cy-Cy-V." As shown in Table 1, the γ1 value of liquid crystal composition LC-002 was smaller than the γ1 values of other liquid crystal compositions that did not contain "3-Cy-Cy-V." The smaller the γ1 value, the faster the response speed, indicating that the inclusion of an alkenyl compound in a liquid crystal composition increases the response speed. Meanwhile, the results of Comparative Examples 1 and 4 indicate that liquid crystal composition LC-002 has a longer _TND than liquid crystal composition LC-001, which does not contain "3-Cy-Cy-V," and furthermore, its VHR after UV _TND exposure was significantly lower than that of liquid crystal composition LC-001. This indicates that liquid crystal compositions containing an alkenyl compound have a longer _TND and experience a decrease in VHR upon UV exposure.

It was shown that by adding the compound of formula (i) to such liquid crystal composition LC-002, the _TND is shortened and a decrease in VHR can be suppressed. Furthermore, by specifying the content of the compound of formula (i) within a predetermined range, the amount of change in pretilt angle [°] can be increased even with short-term UV irradiation.

(Examples 5 and 6)
A polymerizable compound-containing liquid crystal composition was prepared as Example 5, in which 99 parts by mass of the liquid crystal composition LC-001 was added with 1 part by mass of a compound represented by formula (i-1-1-4A) as the formula (i) compound and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1).

Example 6 was a polymerizable compound-containing liquid crystal composition prepared by adding 99 parts by mass of liquid crystal composition LC-001, 1 part by mass of a compound represented by formula (i-1-1-37A) as the formula (i) compound, and 0.3 parts by mass of polymerizable compound A represented by formula (RM-A1) as the polymerizable compound.

For the polymerizable compound-containing liquid crystal compositions of Examples 5 and 6, the UV irradiation time _TND [min] at which the residual amount of the polymerizable compound became less than the lower detection limit, the VHR [%] after _TND UV irradiation, and the pretilt angle change [°] after 200 seconds of UV irradiation were as shown in Table 4 below.

The polymerizable compound-containing liquid crystal compositions of Examples 5 and 6 were also evaluated in the same manner as in Example 1. As a result, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 5 and 6, like Example 1, also solved the problems of the present invention.

Examples 7 to 12
A polymerizable compound-containing liquid crystal composition was prepared as Example 7, in which 99 parts by mass of the liquid crystal composition LC-002 were added with 1 part by mass of a compound represented by formula (i-1-1-4A) as the formula (i) compound and 0.3 parts by mass of a polymerizable compound A represented by formula (RM-A1).

Example 8 was a polymerizable compound-containing liquid crystal composition prepared by adding 99 parts by mass of liquid crystal composition LC-002, 1 part by mass of a compound represented by formula (i-1-1-37A) as the formula (i) compound, and 0.3 parts by mass of polymerizable compound A represented by formula (RM-A1) as the polymerizable compound.

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

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

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

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

For the polymerizable compound-containing liquid crystal compositions of Examples 7 to 12, the UV irradiation time _TND [min] at which the residual amount of the polymerizable compound became less than the lower detection limit, the VHR [%] after _TND UV irradiation, and the pretilt angle change [°] after 200 seconds of UV irradiation were as shown in Table 5 below.

The polymerizable compound-containing liquid crystal compositions of Examples 7 to 12 also had shorter _TND , higher VHR values, and larger pretilt angle changes than those of Comparative Example 4, in which no compound of Formula (i) was added to LC-002. In particular, Example 11, which contained the compound of Formula (i-1-1B), had a smaller _TND and a higher VHR value after UV irradiation than those of Examples 7 to 10 and 12. This is presumably because the compound of Formula (i) does not have a substituent on the ring adjacent to the fused ring, which allows for a shorter UV irradiation time and suppresses deterioration due to UV irradiation.

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

Comparative Example 7 was a polymerizable compound-containing liquid crystal composition prepared by adding 0.3 parts by mass of polymerizable compound A represented by formula (RM-A1) and 0.4 parts by mass of polymerizable compound A represented by formula (RM-B1) to 100 parts by mass of liquid crystal composition LC-002.

Comparative Example 13 was a polymerizable compound-containing liquid crystal composition prepared by adding 99 parts by mass of liquid crystal composition LC-002, 1 part by mass of a compound represented by formula (i-1-1-4A) as the formula (i) compound, and 0.7 parts by mass of polymerizable compound A represented by formula (RM-A1) as the polymerizable compound.

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

For the polymerizable compound-containing liquid crystal compositions of Comparative Examples 6 and 7 and Examples 13 and 14, the UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound became less than the lower detection limit, the VHR [%] after T _ND UV irradiation, and the pretilt angle change [°] after 200 seconds of UV irradiation were as shown in the following Table 6. The content (% by mass) of the compound of formula (i) in the total amount of the polymerizable compound-containing liquid crystal composition was calculated by {parts by mass of the compound of formula (i)/(parts by mass of the liquid crystal composition+parts by mass of the compound of formula (i)+parts by mass of the polymerizable compounds (A and B))}×100.

The UV irradiation time T _ND [minutes] at which the residual amount of the polymerizable compound became below the lower detection limit was shorter in Examples 13 and 14 than in Comparative Examples 6 and 7. The VHR [%] after UV T _ND irradiation was sufficiently higher in Example 13 than in Comparative Example 6, and was also sufficiently higher in Example 17 than in Comparative Example 7. The pretilt angle change [°] after 200 seconds of UV irradiation was larger in Example 13 than in Comparative Example 6, and was also larger in Example 17 than in Comparative Example 7.

Example 14, in which 0.4 parts by mass of the 0.7 parts by mass of the compound of formula (RM-A1) in Example 13 was replaced with the compound of formula (RM-B1), had a higher VHR value than Example 13, and Example 14, which contained polymerizable compound A, polymerizable compound B, and the compound of formula (i), had a value significantly higher than Comparative Examples 6 and 7 and Example 13. These results demonstrate that the inclusion of both polymerizable compound A and polymerizable compound B can further suppress the decrease in VHR.

The results of the above-mentioned Examples and Comparative Examples demonstrate that when the content of the compound of general formula (i) is within a specified range, it is possible to polymerize sufficiently at a high speed, a large tilt angle can be formed with weak or little UV light, and the VHR after UV irradiation is also high. Furthermore, it was found that the occurrence of display defects (burn-in) due to backlight exposure is suppressed, demonstrating high tilt stability.

(Examples 15 to 19)
A polymerizable compound-containing liquid crystal composition was prepared as Example 15, in which 99 parts by mass of the liquid crystal composition LC-001 were added with 1 part by mass of a compound represented by formula (i-1-1-1A) as the compound of Formula (i) and 0.3 parts by mass of a polymerizable compound represented by formula (RM-A2).

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

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

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

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

The polymerizable compound-containing liquid crystal compositions of Examples 15 to 19 were evaluated in the same manner as in Example 1. As a result, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 15 to 19 also solved the problems of the present invention, as in Example 1, suggesting that the effects of the present invention can be achieved by including a predetermined amount of the compound of formula (i), regardless of the type of polymerizable compound.

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

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

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

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

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

The polymerizable compound-containing liquid crystal compositions of Examples 20 to 24 were also evaluated in the same manner as in Example 4. As a result, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 20 to 24 also solved the problems of the present invention, as in Example 4, suggesting that regardless of the type of polymerizable compound, the effects of the present invention can be achieved by including a predetermined amount of the compound of formula (i), even when an alkenyl compound is included.

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

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

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

The polymerizable compound-containing liquid crystal compositions of Examples 25 to 27 were also evaluated in the same manner as in Example 1. As a result, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 25 to 27, like Example 1, also solved the problems of the present invention, suggesting that the effects of the present invention can be achieved by including a specified amount of the compound of formula (i), regardless of the composition of the liquid crystal composition and the type of polymerizable compound in the present invention.

(Examples 28 to 31)
To the polymerizable compound-containing liquid crystal composition obtained in Example 2, 0.005 parts by mass of an antioxidant represented by formula (H-2-1) was further added to prepare a polymerizable compound-containing liquid crystal composition as Example 28.

The polymerizable compound-containing liquid crystal composition obtained in Example 2 was further supplemented with 0.005 parts by mass of an antioxidant represented by formula (H-4-1) to prepare a polymerizable compound-containing liquid crystal composition, designated Example 29.

The polymerizable compound-containing liquid crystal composition obtained in Example 4 was further supplemented with 0.005 parts by mass of an antioxidant represented by formula (H-2-1), to prepare a polymerizable compound-containing liquid crystal composition designated Example 30.

The polymerizable compound-containing liquid crystal composition obtained in Example 4 was further supplemented with 0.005 parts by mass of an antioxidant represented by formula (H-4-1), to prepare a polymerizable compound-containing liquid crystal composition designated Example 31.

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

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

(Examples 32-46)

Liquid crystal compositions LC-006 to LC-010, before the addition of the compound of formula (i) and the polymerizable compound, were prepared in the same manner as LC-001 to LC-005, and their physical properties were measured in the same manner as LC-001 to LC-005. The configurations of liquid crystal compositions LC-006 to LC-010 and the resulting physical properties are shown in Table 7.

Next, polymerizable compound-containing liquid crystal compositions were prepared in the same manner as in Example 1, 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, resulting in Examples 32 to 46.

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

(Examples 47 to 76)
To each of the polymerizable compound-containing liquid crystal compositions used in Examples 32 to 46, 0.005 parts by mass of an antioxidant represented by formula (H-2-1) was further added, and the resulting polymerizable compound-containing liquid crystal compositions were designated Examples 47 to 61.

Furthermore, 0.005 parts by mass of an antioxidant represented by formula (H-4-1) was further added to each of the polymerizable compound-containing liquid crystal compositions used in Examples 32 to 46, and the resulting polymerizable compound-containing liquid crystal compositions were designated Examples 62 to 76.

The polymerizable compound-containing liquid crystal compositions of Examples 47 to 76 were also evaluated in the same manner as in Example 1. As a result, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 47 to 76 were superior to the comparative examples, just like Example 1. From the above, it was confirmed that the problems of the present invention were solved.

Claims (10)

Contains one or more compounds represented by general formula (i-1-1-1) and one or more polymerizable compounds,
A polymerizable compound-containing liquid crystal composition in which the total content of the compounds represented by general formula (i-1-1-1) is more than 0% by mass and less than 2.0% by mass.
(In the formula, R ⁱ¹¹¹ and R ⁱ¹¹² each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 2 to 10 carbon atoms, and one or more hydrogen atoms present in these groups may be substituted with a fluorine atom.) The polymerizable compound may be a compound represented by the general formula (P):
(In the above general formula (P), R ^p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms, or -Sp ^p2 -P ^p2 , one or two or more non-adjacent -CH ₂ - groups in the alkyl group may each independently be substituted with -CH═CH-, -C≡C-, -O-, -CO-, -COO-, or -OCO-, and one or two or more hydrogen atoms in the alkyl group may each independently be substituted with a cyano group, a fluorine atom, or a chlorine atom;
P ^p1 and P ^p2 each independently represent a group represented by the general formula (P ^p1 -1) to the general formula (P ^p1 -9):
(wherein R ^p11 and R ^p12 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms; W ^p11 represents a single bond, —O—, —COO—, or an alkylene group having 1 to 5 carbon atoms; and t ^p11 represents 0, 1, or 2, but when a plurality of R ^p11 , R ^p12 , W ^p11 , and/or t ^p11 are present in a molecule, they may be the same or different.)
Sp ^p1 and Sp ^p2 each independently represent a single bond or a spacer group;
Z ^p1 and Z ^p2 each independently represent 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} —COO—, —COO-CR ^ZP1 ═CH—OCO—, —OCO-CR ^ZP1 ═CH—COO—, —OCO-CR ^ZP1 ═CH—OCO—, —(CH ₂ ) _z -COO—, —( _CH 2 ) z -OCO—, —OCO-(CH ₂ ) _z -, —(C═O)—O—(CH ₂ ) _z -, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF ₂ —, —CF ₂ O—, —OCF ₂ —, —CF ₂ CH ₂ —, —CH ₂ CF ₂ —, —CF ₂ CF ₂ —, or —C≡C— (wherein z's each independently represent an integer of 1 to ₄ , and R Each ^{R ZP1} independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and when there are multiple R ^ZP1s in a molecule, they may be the same or different. In addition, * in the formula represents the point of attachment to Sp ^p1 or Sp ^p2 .
represents
A ^p1 and A ^p2 each independently represent
(a ^p ) a 1,4-cyclohexylene group (in which one —CH ₂ — or two or more non-adjacent —CH ₂ — groups may be replaced by —O—).
(b ^p ) a 1,4-phenylene group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=), and (c ^p ) a naphthalenediyl group, a 1,2,3,4-tetrahydronaphthalenediyl group, a decahydronaphthalenediyl group, a phenanthrene-2,7-diyl group, or an anthracene-2,6-diyl group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=).
represents a group selected from the group consisting of
A ^p3 represents a group selected from the group consisting of the above groups (a ^p ), (b ^p ), and (c ^p ), and a single bond;
The above groups (a ^p ), (b ^p ) and (c ^p ) each independently represent that a hydrogen atom present in this group may be substituted with a cyano group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms or -Sp ^p2 -P ^p2 ;
m ^p1 represents 0, 1, 2 or 3, and when a plurality of Z ^p1 , A ^p2 , Sp ^p2 and/or P ^p2 are present in a molecule, they may be the same or different,
When m ^p1 is 0 and A ^p1 is a group other than a naphthalenediyl group, a phenanthrene-2,7-diyl group, or an anthracene-2,6-diyl group, A ^p3 represents a group other than a single bond. Further, general formula (L):
(wherein R ^L1 and R ^L2 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — groups in the alkyl group may each independently be replaced by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—;
n ^L1 represents 0, 1, 2 or 3;
A ^L1 , A ^L2 and A ^L3 each independently represent (a) a 1,4-cyclohexylene group (in which one —CH ₂ — or two or more non-adjacent —CH ₂ — groups may be replaced by —O—).
(b) a 1,4-phenylene group (one -CH= or two or more non-adjacent -CH= groups in this group may be replaced by -N=), and (c) a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one -CH= or two or more non-adjacent -CH= groups in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by -N=).
wherein the groups (a), (b) and (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom;
Z ^L1 and Z ^L2 each independently 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 a plurality of A ^L2s are present, they may be the same or different; when n ^L1 is 2 or 3 and a plurality of Z ^L2s are present, they may be the same or different.
However, compounds represented by general formula (i-1-1-1) are excluded.
3. The polymerizable compound-containing liquid crystal composition according to claim 1, which contains one or more compounds selected from the group consisting of compounds represented by the following formula: Further, general formula (N-1)
(In the formula, R ^N11 and R ^N12 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — groups in the alkyl group may each independently be replaced by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—;
A ^N11 and A ^N12 each independently represent (a) a 1,4-cyclohexylene group (in which one —CH ₂ — or two or more non-adjacent —CH ₂ — groups may be replaced by —O—).
(b) a 1,4-phenylene group (in which one —CH= or two or more non-adjacent —CH= groups may be replaced by —N=).
(c) a group selected from the group consisting of a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or a decahydronaphthalene-2,6-diyl group (one —CH= or two or more non-adjacent —CH= groups present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be replaced by —N=), and (d) a 1,4-cyclohexenylene group, wherein the groups (a), (b), (c), and (d) each independently may be substituted by a cyano group, a fluorine atom, or a chlorine atom,
Z ^N11 and Z ^N12 each independently 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—;
n ^N11 and n ^N12 each independently represent an integer of 0 to 3, provided that n ^N11 +n ^N12 is 1, 2 or 3, and when a plurality of A ^N11 to A ^N12 and Z ^N11 to Z ^N12 are present, they may be the same or different.
However, the compounds represented by general formula (i-1-1-1) and general formula (L) are excluded. 4. The liquid crystal composition according to claim 3, wherein 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 polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 5, further comprising, as the polymerizable compound, one or more polymerizable compounds B having one or more polymerizable groups and one or more polar groups within the molecular structure. The polymerizable compound B has the general formula (AT):
(wherein Sp ^AT1 represents a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, one or more hydrogen atoms in the alkylene group may be substituted with —OH, —CN, —W ^AT1 -Z ^AT1 or P ^AP1 -Sp ^AP1 —, and one or two or more non-adjacent —CH ₂ — groups in the alkylene group may be substituted with a cyclic group, —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO— so that the oxygen atoms are not directly bonded,
^WAT1 is a single bond or the following general formula (WAT1) or (WAT2):
(In the formula, Sp ^WAT1 and Sp ^WAT2 each independently represent a single bond or a linear or branched alkylene group having 1 to 25 carbon atoms, one or more hydrogen atoms in the alkylene group may be substituted with —OH, —CN, or P ^AP1 -Sp ^AP1 —, and one or two or more non-adjacent —CH ₂ — groups in the alkylene group may be substituted with a cyclic group, —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—, so that the oxygen atoms are not directly adjacent to each other. * in the formula represents a bond.)
Z ^AT1 represents a monovalent polar group containing a polar element, and one or more hydrogen atoms in Z ^AT1 may be substituted with —OH, —CN, or —P ^AP1 —Sp ^AP1 —.
^PAP1 represents a polymerizable group;
Sp ^AP1 represents a spacer group.
* in the formula represents a bond.)
The liquid crystal composition according to claim 6 , wherein the compound is a compound represented by the formula: A liquid crystal display element using a liquid crystal composition containing a polymerizable compound according to any one of claims 1 to 7. An active matrix liquid crystal display element using a liquid crystal composition containing a polymerizable compound according to any one of claims 1 to 7. A liquid crystal display element for PSA mode, PSVA mode, PS-IPS mode, or PS-FFS mode, using the polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 7.