CN113174269A

CN113174269A - Polymerizable compound-containing liquid crystal composition and liquid crystal display element using same

Info

Publication number: CN113174269A
Application number: CN202110040761.XA
Authority: CN
Inventors: 长谷部浩史; 藤沢宣
Original assignee: DIC Corp
Current assignee: DIC Corp
Priority date: 2020-01-27
Filing date: 2021-01-13
Publication date: 2021-07-27
Also published as: JP2021116358A; TW202138548A

Abstract

The present invention has been made to solve the above problems, and an object of the present invention is to provide a polymerizable compound-containing liquid crystal composition that can produce a liquid crystal display element having a small pretilt angle variation while maintaining a constant transmittance, while achieving a fast off-response, and a liquid crystal display element using the same. The present invention provides a polymerizable compound-containing liquid crystal composition and a liquid crystal display element using the same, wherein the polymerizable compound-containing liquid crystal composition comprises: one or more polymerizable compounds represented by general formula (PI), one or more compounds represented by general formula (PII), and one or more liquid crystal compounds selected from the group consisting of compounds represented by general formulae (N-01) to (N-05).

Description

Polymerizable compound-containing liquid crystal composition and liquid crystal display element using same

Technical Field

The present invention relates to a liquid crystal composition containing a polymerizable compound and a liquid crystal display element using the same.

Background

In recent years, liquid crystal televisions have been increasing in size, and as a result, the moving speed of a display object moving on a screen has become faster, and therefore, it has been demanded to increase the response speed of liquid crystal. Therefore, in order to achieve higher display speed, for example, polymer-stabilized (PS) or polymer-sustained alignment (PSA) displays have been widely used, which mainly employ a vertical alignment mode and provide a pretilt angle to a liquid crystal material to increase the rise response (on response) at the time of voltage application (see patent documents 1 to 4).

Specifically, the PS or PSA display is obtained by adding a small amount of polymerizable compound to a liquid crystal medium, applying an electric field to upper and lower electrodes to tilt liquid crystal molecules in one direction, and irradiating ultraviolet light (UV light) in this state to polymerize the polymerizable compound, thereby forming a polymer layer on an alignment film. PS or PSA displays use a technique of fixing the alignment state of a tilted liquid crystal by the polymer layer, thereby speeding up the rising response (on response) at the time of voltage application.

However, as the size of liquid crystal televisions has increased in recent years, the moving speed of a display object moving on a screen has become faster, and thus further improvement in the response speed of liquid crystal is required.

Therefore, conventionally, as a means for improving the response speed, not only the increase in the rising response (on response) at the time of voltage application but also the improvement in the response speed at the time of discharge from the time of voltage application (at the time of switching-off) have been attempted, and for example, patent document 5 discloses a liquid crystal display element in which a composition containing a liquid crystal compound and a diacrylate containing a liquid crystal ortho group and containing the diacrylate in a range of approximately 2 to 15 mass% is injected into a liquid crystal cell and then irradiated with ultraviolet light to form a polymer network formed of a polymer of the diacrylate in the liquid crystal cell. The composition disclosed in patent document 5 contains a large amount of polymerizable compounds, as compared with the case of the composition used in a PS or PSA display, and the liquid crystal display element forms a polymer network in a liquid crystal layer. As a result, the relaxation process to the initial alignment state at the time of the off response (hereinafter, simply referred to as "off response") is accelerated by utilizing the interaction between the polymer and the liquid crystal molecules in the attractive force, and the off response is speeded up.

However, the liquid crystal display element described above is still susceptible to improvement in that the more the interaction between the polymer and the liquid crystal molecules, that is, the faster the response speed, the more the stability of the pretilt angle is easily deteriorated, and the more the transmittance is easily deteriorated.

[ Prior art documents ]

[ patent document ]

[ patent document 1] Japanese patent laid-open No. 2003-307720

[ patent document 2] Japanese patent application laid-open No. 2009-104119

[ patent document 3] Japanese patent application laid-open No. 2008-116931

[ patent document 4] specification of U.S. patent application publication No. 2010/0188618

[ patent document 5] International publication No. 2015/122457

Disclosure of Invention

[ problems to be solved by the invention ]

The present invention has been made to solve the above problems, and an object of the present invention is to provide a polymerizable compound-containing liquid crystal composition that can produce a liquid crystal display element having a small pretilt angle variation while maintaining a constant transmittance, while achieving a fast off-response, and a liquid crystal display element using the same.

[ means for solving problems ]

The present inventors have made extensive studies and as a result, have found that the above-mentioned problems can be solved by containing a polymerizable compound having a specific structure in a liquid crystal composition at a specific concentration, and have completed the present invention.

That is, the present invention provides a polymerizable compound-containing liquid crystal composition having negative dielectric anisotropy and comprising:

one or more polymerizable compounds represented by the general formula (PI);

one or more polymerizable compounds represented by the following general formula (PII); and

one or more liquid crystal compounds selected from the group consisting of compounds represented by the following general formulae (N-01) to (N-05),

[ solution 1]

(in the general formula (PI),

R¹⁰²、R¹⁰³、R¹⁰⁴、R¹⁰⁵、R¹⁰⁶、R¹⁰⁷、R¹⁰⁸and R¹⁰⁹Each independently represents any one of an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom,

P¹¹and P¹²Each independently represents any one of the following general formulae (R-1) to (R-9),

[ solution 2]

(in the general formula (R-1) to the general formula (R-9),

R²¹、R³¹、R⁴¹、R⁵¹and R⁶¹Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms,

w and T each independently represent a single bond, -O-, -COO-, or an alkylene group having 1 to 5 carbon atoms,

p, t and q each independently represent 0, 1 or 2,

is represented by¹¹Or S¹²Key node of (2)

S¹¹And S¹²Each independently represents a single bond or an alkylene group having 1 to 15 carbon atoms, but S¹¹And S¹²Not simultaneously represent a single bond, one or two or more-CH groups which are not adjacent to each other in the alkylene group₂May be independently substituted by-O-, -OCO-or-COO-in such a way that the oxygen atoms are not directly adjacent to each other

[ solution 3]

(in the general formula (PII),

R²⁰¹、R²⁰²、R²⁰³、R²⁰⁴、R²⁰⁵、R²⁰⁶、R²⁰⁷、R²⁰⁸、R²⁰⁹and R²¹⁰Each independently represents P²¹An alkyl group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, a fluorine atom or a hydrogen atom, provided that R²⁰¹、R²⁰²、R²⁰³、R²⁰⁴、R²⁰⁵、R²⁰⁶、R²⁰⁷、R²⁰⁸、R²⁰⁹And R²¹⁰At least one of them represents P²¹，

P²¹Represents any one of general formulae (R-1) to (R-9) in the general formula (PI),

n²¹represents a number of 0, 1 or 2,

A²¹is selected from the group consisting of

(a)1, 4-cyclohexylene radical (one-CH present in the radical)₂-or two or more-CH's which are not contiguous₂-is substitutable as-O-)

(b)1, 4-phenylene (one or two or more-CH-which are not adjacent to each other present in the group may be substituted by-N) and

(c) naphthalenediyl, 1,2,3, 4-tetrahydronaphthalenediyl or decahydronaphthalenediyl (where one or two or more-CH groups which are not adjacent to each other may be replaced by-N-H-in naphthalenediyl or 1,2,3, 4-tetrahydronaphthalenediyl)

The hydrogen atoms in the group (a), the group (b) and the group (c) may be independently substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or P²¹Substituted at A²¹In the case of plural, A²¹Can be the same or different and can be different,

L²¹represents a single bond, -OCH₂-、-CH₂O-、-C₂H₄-、-OC₂H₄O-、-COO-、-OCO-、-CH＝CR^a-COO-、

-CH＝CR^a-OCO-、-COO-CR^a＝CH-、-OCO-CR^a＝CH-、-(CH₂)_z-COO-、-(CH₂)_z-OCO-、-OCO-(CH₂)_z-、-COO-(CH₂)_z-、-CH＝CH-、-CF₂O-、-OCF₂-or-C ≡ C-,

R^aeach independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

z independently represents an integer of 1 to 4 respectively

[ solution 4]

(in the general formula (N-01) to the general formula (N-05),

R²¹and R²²Independently represents 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, and one or two or more-CH groups which are not adjacent to each other₂-may be independently substituted by-CH ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-, respectively, in such a way that oxygen atoms are not directly adjacent,

Z¹each independently represents a single bond, -CH₂CH₂-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-, -CF-or-C.ident.C-,

m independently represents 1 or 2),

the total content of the polymerizable compounds represented by the general formula (PII) is 0.6 to 1.4 mass%, and the mass ratio (PII/PI) of the total content of the polymerizable compounds represented by the general formula (PII) to the total content of the polymerizable compounds represented by the general formula (PI) is 0.25 or more.

[ Effect of the invention ]

According to the present invention, a polymerizable compound-containing liquid crystal composition which can produce a liquid crystal display element having a small amount of change in pretilt angle even when the response speed is increased by the interaction between liquid crystal and a polymer while maintaining a constant transmittance while realizing a fast off response, and a liquid crystal display element using the same can be provided.

Detailed Description

Hereinafter, the polymerizable compound-containing liquid crystal composition of the present invention and the liquid crystal display element using the same will be described in detail. In the following description, the polymerizable compound represented by the general formula (PI) may be referred to as a polymerizable compound (PI). The same applies to other compounds.

The term "polymerizable compound" refers to a "compound having a polymerizable group".

A. Liquid crystal composition containing polymerizable compound

[1] A polymerizable compound represented by the general formula (PI)

The polymerizable compound-containing liquid crystal composition of the present invention contains one or more polymerizable compounds represented by the general formula (PI).

[ solution 5]

In the general formula (PI), R¹⁰²、R¹⁰³、R¹⁰⁴、R¹⁰⁵、R¹⁰⁶、R¹⁰⁷、R¹⁰⁸And R¹⁰⁹Each independently represents any one of an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom.

The alkyl group having 1 to 18 carbon atoms may be linear or branched, but is preferably linear from the viewpoint of obtaining good orientation.

The number of carbon atoms of the alkyl group having 1 to 18 carbon atoms is preferably 1 to 3 when importance is placed on solubility in the liquid crystal composition, and is preferably 10 to 18 when importance is placed on vertical alignment of the liquid crystal composition.

The alkoxy group having 1 to 18 carbon atoms may be linear or branched, but is preferably linear from the viewpoint of obtaining good orientation.

The number of carbon atoms of the alkoxy group having 1 to 18 carbon atoms is preferably 1 to 3 when importance is placed on solubility in the liquid crystal composition, and is preferably 10 to 18 when importance is placed on vertical alignment of the liquid crystal composition.

Examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom.

From the viewpoint of ensuring compatibility with the liquid crystal compound, R is preferable¹⁰²、R¹⁰³、R¹⁰⁶、R¹⁰⁷And R¹⁰⁹At least one of them is a halogen atom, more preferably a fluorine atom.

In the general formula (PI), P¹¹And P¹²Each independently represents any one of the following general formulae (R-1) to (R-9).

[ solution 6]

In the general formula (R-1) to the general formula (R-9), R²¹、R³¹、R⁴¹、R⁵¹And R⁶¹Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a haloalkyl group having 1 to 5 carbon atoms.

Examples of the alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, and a propyl group.

Examples of the haloalkyl group having 1 to 5 carbon atoms include a trifluoromethyl group, a difluoroethyl group and the like.

As R²¹、R³¹、R⁴¹、R⁵¹And R⁶¹Preferably, each is independently a hydrogen atom or a methyl group.

In the general formulae (R-1) to (R-9), W and T each independently represent a single bond, -O-, -COO-, or an alkylene group having 1 to 5 carbon atoms.

Examples of the alkylene group having 1 to 5 carbon atoms include a methylene group, an ethylene group, and a propylene group.

In the general formulae (R-1) to (R-9), p, t and q each independently represent 0, 1 or 2, preferably 0 or 1.

In general formula (R-1) to general formula (R-9), represents and S¹¹Or S¹²The key node of (1).

From the viewpoint of ensuring proper reactivity, wherein P¹¹And P¹²Preferably independently of each other, of the formula (R-1), the formula (R-2), the formula (R-3), the formula (R-4), the formula (R-5) or the formula (R-7), preferably of the formula (R-1), the formula (R-2), the formula (R-3) or the formula (R-4), preferably of the formula (R-1), preferably acrylic acid (R-1)²¹Hydrogen atom) or a methacrylic group (in the formula (R-1), R²¹Methyl), preferably a methacrylate group.

In addition, P¹¹And P¹²May be the same or different, but are preferably the same.

In addition, in P¹¹And P¹²When the same formulae (R-1) to (R-9) are selected, the same symbols in the formulae may be the same or different.

In addition, from the viewpoint of compatibility with the liquid crystal compound, it is preferable that R in the polymerizable compound represented by the general formula (PI)¹⁰²、R¹⁰³、R¹⁰⁴、R¹⁰⁵、R¹⁰⁶、R¹⁰⁷、R¹⁰⁸And R¹⁰⁹Not simultaneously representing a hydrogen atom, R¹⁰²、R¹⁰³、R¹⁰⁴、R¹⁰⁵、R¹⁰⁶、R¹⁰⁷、R¹⁰⁸And R¹⁰⁹At least one of the above groups is a halogen atom, an alkyl group having 1 to 18 carbon atoms or an alkoxy group having 1 to 18 carbon atoms.

In the general formula (PI), S¹¹And S¹²Each independently represents a single bond or an alkylene group having 1 to 15 carbon atoms, but S¹¹And S¹²Not simultaneously represent a single bond, one or two or more-CH groups which are not adjacent to each other in the alkylene group₂Can be taken independently of one another via-O-, -OCO-or-COO-in such a way that the oxygen atoms are not directly adjacent to one anotherAnd (4) generation.

I.e. S¹¹And S¹²At least one of which is an alkylene group of a desired number of carbon atoms.

The number of carbon atoms of the alkylene group is 1 to 15, preferably 1 to 8, preferably 1 to 4, preferably 2 to 3.

By making S¹¹And S¹²At least one of which is one of the radicals or non-adjacent two or more-CH₂Alkylene of the desired number of carbon atoms which may each be independently substituted by-O-, -OCO-or-COO-in such a way that the oxygen atoms are not directly adjacent, and S¹¹And S¹²In comparison with the case where both are single bonds, a polymer network which does not easily disturb the orientation of the liquid crystal compound can be easily formed in the liquid crystal layer. Thus, the liquid crystal display element using the polymerizable compound-containing liquid crystal composition of the present invention has advantages that the light transmittance can be improved and the off-response speed by the interaction of the polymer with the liquid crystal molecules due to the attractive force can be increased. Further, the polymerizable compound represented by the general formula (PI) has an advantage that compatibility with the liquid crystal compound is improved, and the polymerizable compound is less likely to precipitate by low-temperature storage. Wherein S is¹¹And S¹²Preferably, each is independently an alkylene group having 1 to 15 carbon atoms (one of the groups-CH)₂-optionally substituted with-O-, preferably an alkylene group having 1 to 8 carbon atoms (one of the groups-CH)₂-may be substituted with-O-, preferably an alkylene group having 1 to 4 carbon atoms (one of the groups-CH)₂May be substituted by-O-, preferably one of the radicals-CH₂An alkylene group having 1 to 4 carbon atoms substituted with-O-. Among them, preferred is-CH bonded to a benzene ring₂-alkylene substituted by-O-.

Specifically, in the general formula (PI), SP¹¹And/or SP¹²Particularly preferably an alkylene group having 1 to 4 carbon atoms (one-CH group in the group) bonded to an aromatic ring via one oxygen atom₂-may be substituted by-O) -, i.e., -O- (CH)₂)_s- (s represents an integer of 1 to 3).

In addition, two or more S of the general formula (PI)¹¹And S¹²May be the same or different.

The types of the polymerizable compounds represented by the general formula (PI) contained in the polymerizable compound-containing liquid crystal composition of the present invention are preferably one to five, preferably one to four, preferably one to three, preferably one to two.

In another embodiment, the polymerizable compound represented by the general formula (PI) is preferably two to five, preferably two to four, and preferably two to three in kind, from the viewpoint of improving the vertical alignment property and the alignment unevenness.

Preferred examples of the polymerizable compound represented by the general formula (PI) include compounds represented by the following general formulae (PI-1) to (PI-18).

[ solution 7]

[ solution 8]

[ solution 9]

In the general formulae (PI-1) to (PI-18), Sp^11-1And Sp^12-1Each independently represents an alkylene group having 1 to 8 carbon atoms or-O- (CH)₂)_s- (s represents an integer of 1 to 7, and oxygen atom is bonded to the ring).

Among them, the polymerizable compound represented by the general formula (PI) is preferably one or more selected from the group consisting of the compounds represented by the above-mentioned formulae (PI-1), (PI-2), (PI-4), (PI-5) and (PI-6), and is preferably one or more selected from the group consisting of the compounds represented by the general formulae (PI-1), (PI-2) and (PI-4).

Preferable specific examples of the polymerizable compound represented by the general formula (PI) include compounds represented by the following structural formulae (PI-1-1) to (PI-6-2).

[ solution 10]

[ solution 11]

The higher the content of the polymerizable compound represented by the general formula (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2), the more dense the polymer network can be formed in the liquid crystal layer in the liquid crystal display element produced using the polymerizable compound-containing liquid crystal composition of the present invention, and the faster the switching response can be achieved.

Specifically, the lower limit of the content of the polymerizable compound represented by the general formula (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2) is preferably 2.0% by mass or more, preferably 2.1% by mass or more, and preferably 2.2% by mass or more, based on 100% by mass of the polymerizable compound-containing liquid crystal composition.

In particular, a liquid crystal display element manufactured using the polymerizable compound-containing liquid crystal composition of the present invention contains 2.3 mass% or more of the polymerizable compound (monomer) represented by the general formula (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1) to (PI-6-2) is preferable because a polymer network (polymer network) is formed not only on the substrate surface of the liquid crystal display but also in the liquid crystal medium, and therefore, the orientation is strongly stabilized by the polymer network when no voltage is applied, and as a result, the switching response is more effectively accelerated.

On the other hand, if the content of the polymerizable compound represented by the general formula (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2) is too high, a liquid crystal display element using the liquid crystal composition containing the polymerizable compound may cause a decrease in light transmittance or an increase in driving voltage.

Therefore, the upper limit of the content of the polymerizable compound represented by the general formula (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2) is preferably 5.6% by mass or less, preferably 4.8% by mass or less, preferably 4.0% by mass or less, preferably 3.5% by mass or less, preferably 3.2% by mass or less, and preferably 3.0% by mass or less, based on 100% by mass of the polymerizable compound-containing liquid crystal composition.

More specific contents of the polymerizable compounds represented by the general formula (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2) in the polymerizable compound-containing liquid crystal composition of the present invention can be set in combination with the above upper limit and lower limit, and are, for example, preferably in the range of 2.0 to 5.6 mass%, preferably in the range of 2.1 to 4.8 mass%, preferably in the range of 2.2 to 4.0 mass%, and preferably in the range of 2.3 to 3.5 mass%.

When the polymerizable compound-containing liquid crystal composition of the present invention contains two or more polymerizable compounds represented by the general formula (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2), the phrase "the content of the polymerizable compounds represented by the general formula (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2) in 100% by mass of the polymerizable compound-containing liquid crystal composition" means the total content of two or more polymerizable compounds represented by the general formulae (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2).

[2] A polymerizable compound represented by the general formula (PII)

The polymerizable compound-containing liquid crystal composition of the present invention contains one or more polymerizable compounds represented by the general formula (PII).

[ solution 12]

General formula (PII)) In, R²⁰¹、R²⁰²、R²⁰³、R²⁰⁴、R²⁰⁵、R²⁰⁶、R²⁰⁷、R²⁰⁸、R²⁰⁹And R²¹⁰Each independently represents P²¹An alkyl group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, a fluorine atom or a hydrogen atom, provided that R²⁰¹、R²⁰²、R²⁰³、R²⁰⁴、R²⁰⁵、R²⁰⁶、R²⁰⁷、R²⁰⁸、R²⁰⁹And R²¹⁰At least one of them represents P²¹。

P²¹And the above-mentioned "[ 1]]P described in the polymerizable Compound represented by the general formula (PI)¹¹And P¹²The same definition is applied.

Wherein, P²¹Preferably of the general formula (R-1), preferably acrylic acid (R)²¹H) or methacrylic acid group (R)²¹＝CH₃) Preferably a methacrylic acid group (R)²¹＝CH₃)。

The alkyl group having 1 to 18 carbon atoms may be linear or branched, but is preferably linear from the viewpoint of ensuring good liquid crystallinity of the liquid crystal composition containing the polymerizable compound.

The number of carbon atoms of the alkyl group having 1 to 18 carbon atoms is preferably 1 to 16, preferably 1 to 10, preferably 1 to 8, preferably 1 to 6, preferably 1 to 4, preferably 1 to 3.

The alkoxy group having 1 to 18 carbon atoms may be linear or branched, but is preferably linear from the viewpoint of ensuring good liquid crystallinity of a liquid crystal composition containing a polymerizable compound.

In the general formula (PII), n²¹0, 1 or 2, from the viewpoint of ensuring good low-temperature storage stability of the polymerizable compound-containing liquid crystal compositionPreferably 0 or 1.

In the general formula (PII), A²¹Represents a group selected from (a)1, 4-cyclohexylene (one-CH present in said group)₂-or two or more-CH's which are not contiguous₂A group which may be substituted by-O-), (b)1, 4-phenylene (one or two or more noncontiguous-CH-may be substituted by-N-) and (c) naphthalenediyl, 1,2,3, 4-tetrahydronaphthalenediyl or decahydronaphthalenediyl (naphthalenediyl or one or two or more noncontiguous-CH-present in 1,2,3, 4-tetrahydronaphthalenediyl) wherein hydrogen atoms in the group (a), the group (b) and the group (c) may independently be substituted by an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or P²¹And (4) substitution.

Examples of the halogen atom include a chlorine atom, a bromine atom, and a fluorine atom is preferable.

In the group (c), the naphthalenediyl group and the 1,2,3, 4-tetrahydronaphthalenediyl group are groups bonded at two positions selected from the 1-8 positions, specifically, at one of two positions selected from the 1-8 positions with an adjacent benzene ring (phenyl group) or an adjacent A²¹Bonding at another position with an adjacent A²¹Or L²¹Bonding.

In the group (c), the decahydronaphthalenediyl group is a group bonded to two positions selected from the 1-10 positions, specifically to the adjacent benzene ring (phenyl group) or the adjacent A at one of two positions selected from the 1-10 positions²¹Bonding at another position with an adjacent A²¹Or L²¹Bonding.

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

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

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

In the general formula (PII), A²¹Among them, 1, 4-phenylene or naphthalene-2, 6-diyl is preferable, and 1, 4-phenylene is preferable.

In A²¹In the case of plural, A²¹May be the same or different.

In the general formula (PII), L²¹Represents a single bond, -OCH₂-、-CH₂O-、-C₂H₄-、-OC₂H₄O-、-COO-、-OCO-、-CH＝CR^a-COO-、-CH＝CR^a-OCO-、-COO-CR^a＝CH-、-OCO-CR^a＝CH-、-(CH₂)_z-COO-、-(CH₂)_z-OCO-、-OCO-(CH₂)_z-、-COO-(CH₂)_z-、-CH＝CH-、-CF₂O-、-OCF₂-or-C ≡ C-,

z independently represents an integer of 1 to 4.

Wherein as L²¹Preferably a single bond, -OCH₂-、-CH₂O-、-C₂H₄-、-COO-、-OCO-、-CH＝CH-COO-(R^a＝H)、-CH＝CH-OCO-(R^a＝H)、-COO-CH＝CH-(R^a＝H)、-OCO-CH＝CH-(R^a＝H)、-(CH₂)₂-COO-(z＝2)、-(CH₂)₂-OCO-(z＝2)、-OCO-(CH₂)₂-(z＝2)、-COO-(CH₂)₂-(z＝2)、-CH＝CH-、-CF₂O-、-OCF₂-or-C ≡ C-.

P in the formula (PII)²¹The number of (c) is preferably 2 or more.

In addition, P in the formula (PII)²¹The number of (c) is preferably 4 or less.

P in the formula (PII)²¹The number of (a) is preferably 2 or more and 4 or less, preferably 2 or more and 3 or less, preferably 2.

That is, the compound represented by the general formula (PII) is a compound represented by two benzene rings (phenyl groups) and, if necessary, ring A²¹The structure formed by connection is not ring A²¹Has at least one P in the two phenyl rings (phenyl groups)²¹Therefore, the compound represented by the general formula (PII) exerts an action and an effect as a polymerizable compound. In particular, the polymerizable compound of the formula (PII) contributes to improvement of the stability of the pretilt angle although it contributes less to improvement of the off-switching speed than the polymerizable compound of the formula (PI).

In the general formula (PII), R²⁰¹、R²⁰²、R²⁰³、R²⁰⁴、R²⁰⁵、R²⁰⁶、R²⁰⁷、R²⁰⁸、R²⁰⁹And R²¹⁰Is at least one of P²¹Preferably R²⁰¹、R²⁰²、R²⁰⁴、R²⁰⁷、R²⁰⁹And R²¹⁰Is at least one of P²¹Preferably R²⁰¹And R²¹⁰Is at least one of P²¹。

In the general formula (PII), in P²¹In the case of plural, each P²¹May be the same or different.

Particularly preferably R²⁰¹And R²¹⁰Are each independently P²¹In this case, R²⁰¹And R²¹⁰May be the same P²¹Or may be different P²¹。

In addition, in R²⁰¹And R²¹⁰Are each independently P²¹In the case of (1), R²⁰²、R²⁰³、R²⁰⁴、R²⁰⁵、R²⁰⁶、R²⁰⁷、R²⁰⁸And R²⁰⁹Preferably each independently is P²¹An alkyl group having 1 to 3 carbon atoms, a fluorine atom or a hydrogen atom, preferably P²¹Fluorine atom or hydrogen atom, preferably fluorine atom or hydrogen atom.

The polymerizable compound represented by the general formula (PII) contained in the polymerizable compound-containing liquid crystal composition of the present invention is preferably one to five, preferably one to four, preferably one to three, preferably one to two in kind.

In another embodiment, the polymerizable compound represented by the general formula (PII) is preferably two to five species, preferably two to four species, and preferably two to three species, from the viewpoint of improving the vertical alignment property and the alignment unevenness.

Preferred examples of the polymerizable compound represented by the general formula (PII) of the present invention include compounds represented by the following general formula (PII-a).

[ solution 13]

In the general formula (PII-A), R^A202、R^A203、R^A204、R^A205、R^A206、R^A207、R^A208And R^A209Each independently represents an alkyl group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, a fluorine atom or a hydrogen atom.

As R^A202、R^A203、R^A204、R^A205、R^A206、R^A207、R^A208And R^A209Combinations of (1) include R^A202、R^A203、R^A204、R^A205、R^A206、R^A208And R^A209Represents a hydrogen atom, R^A207Represents a combination of any one of an alkyl group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, and the like.

Preferred examples of the polymerizable compound represented by the general formula (PII) of the present invention include compounds represented by the following structural formulae (PII-1) to (PII-49), and preferably a compound represented by the structural formula (PII-5).

[ solution 14]

[ solution 15]

[ solution 16]

[ solution 17]

[ solution 18]

[ solution 19]

[ solution 20]

[ solution 21]

The content of the polymerizable compound represented by the general formula (PII), the general formula (PII-A), the structural formula (PII-1) to the structural formula (PII-49) is 0.6 mass% or more and 1.4 mass% or less, preferably 0.7 mass% to 1.2 mass%, and preferably 0.8 mass% or more and 1.1 mass% or less, based on 100 mass% of the polymerizable compound-containing liquid crystal composition.

When the content of the polymerizable compound represented by the general formula (PII), the general formula (PII-A), the structural formula (PII-1) to the structural formula (PII-49) is less than 0.6% by mass, the stability of the pretilt angle is deteriorated.

When the content of the polymerizable compound represented by the general formula (PII), the general formula (PII-A), the structural formula (PII-1) to the structural formula (PII-49) exceeds 1.4% by mass, the transmittance of the liquid crystal display element deteriorates.

When the polymerizable compound-containing liquid crystal composition of the present invention contains two or more polymerizable compounds represented by the general formula (PII), the general formula (PII-A), the structural formula (PII-1) to the structural formula (PII-49), the "content of the polymerizable compounds represented by the general formula (PII), the general formula (PII-A), the structural formula (PII-1) to the structural formula (PII-49) in 100% by mass of the polymerizable compound-containing liquid crystal composition" means the total content of the two or more polymerizable compounds represented by the general formula (PII), the general formula (PII-A), the structural formula (PII-1) to the structural formula (PII-49).

The mass ratio (PII/PI) of the total content of the polymerizable compounds represented by the general formula (PII), the general formula (PII-A), the structural formula (PII-1) to the structural formula (PII-49) to the total content of the polymerizable compounds represented by the general formula (PI), the general formula (PI-1) to the general formula (PI-18), the structural formula (PI-1-1) to the structural formula (PI-6-2) is 0.25 or more, preferably 0.28 or more, and preferably 0.3 or more.

When the mass ratio (PII/PI) of the total content of the polymerizable compounds represented by the general formula (PII), the general formula (PII-A), the structural formula (PII-1) to the structural formula (PII-49) to the total content of the polymerizable compounds represented by the general formula (PI), the general formula (PI-1) to the general formula (PI-18), the structural formula (PI-1-1) to the structural formula (PI-6-2) is less than 0.25, the stability of the pretilt angle is deteriorated.

From the viewpoint of suppressing deterioration of transmittance, the mass ratio (PII/PI) of the total content of the polymerizable compounds represented by the general formula (PII), the general formula (PII-a), the structural formula (PII-1) to the structural formula (PII-49) to the total content of the polymerizable compounds represented by the general formula (PI), the general formula (PI-1) to the general formula (PI-18), the structural formula (PI-1-1) to the structural formula (PI-6-2) is preferably 0.5 or less, preferably 0.4 or less, and preferably 0.36 or less.

From the viewpoint of achieving both the transmittance and the stability of the pretilt angle, the mass ratio (PII/PI) of the total content of the polymerizable compounds represented by the general formulae (PII), (PII-A), and (PII-1) to (PII-49) to the total content of the polymerizable compounds represented by the general formulae (PI), and (PI-1) to (PI-18) and (PI-1-1) to (PI-6-2) is preferably 0.25 to 0.5, more preferably 0.28 to 0.4, and still more preferably 0.3 to 0.36.

From the viewpoint of achieving both good response speed and good transmittance, the total content of the polymerizable compounds represented by the general formulae (PI), the general formulae (PI-1) to (PI-18), and the structural formulae (PI-1-1) to (PI-6-2), and the polymerizable compounds represented by the general formulae (PII), the general formulae (PII-A), and the structural formulae (PII-1) to (PII-49) is preferably 2.25 to 7.0% by mass, and more preferably 2.5 to 4.2% by mass, based on 100% by mass of the polymerizable compound-containing liquid crystal composition.

[3] Liquid crystal compounds

The polymerizable compound-containing liquid crystal composition of the present invention contains one or more liquid crystal compounds selected from the group of compounds represented by general formulae (N-01) to (N-05).

These liquid crystal compounds correspond to compounds having negative dielectric anisotropy. The "liquid crystal compound having negative dielectric anisotropy" refers to a compound in which Δ ∈ has a negative sign and an absolute value thereof is greater than 2. The Δ ∈ of the compound is a value obtained by extrapolating from a measured value of dielectric anisotropy of a composition in which the dielectric property is substantially neutral at 20 ℃.

[ solution 22]

In the general formula (N-01) to the general formula (N-05), R²¹And R²²Each independently represents 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 atomsOne or non-adjacent two or more-CH groups₂-may be independently substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-, respectively, in such a way that the oxygen atoms are not directly adjacent.

R²¹Preferably an alkyl group having 1 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 2 to 4 carbon atoms. However, in Z¹R is other than a single bond²¹Preferably an alkyl group having 1 to 3 carbon atoms.

R²²Preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably an alkoxy group having 1 to 4 carbon atoms.

The alkenyl group having 2 to 8 carbon atoms includes those represented by the formulae (R1) to (R5), and preferably those represented by the formulae (R1) and (R2).

[ solution 23]

(Black dots in the formulae represent carbon atoms in the ring structure.)

Z¹Each independently represents a single bond, -CH₂CH₂-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH ═ CH-, -CF ═ CF-or-C ≡ C-.

m independently represents 1 or 2.

When m is 1, Z¹Preferably a single bond or-CH₂O-。

When m is 2, Z¹Preferably a single bond, -CH₂CH₂-or-CH₂O-。

The fluorine atom of the compounds represented by the general formulae (N-01) to (N-05) may be substituted with a chlorine atom which is also a halogen atom. However, the content of the compound substituted with a chlorine atom is preferably as small as possible, and is preferably not contained.

The hydrogen atoms present in the ring of the compounds represented by the general formulae (N-01) to (N-05) may each independently be substituted by a fluorine atom or a chlorine atom.

The compounds represented by the general formulae (N-01) to (N-05) are preferably compounds having negative Δ ∈ and an absolute value of greater than 3. In particular, R²²Preferably represents an alkoxy group having 1 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkoxy group having 1 to 4 carbon atoms.

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

[ solution 24]

In the general formula (N-01-1) to the general formula (N-01-4), R²⁴Each independently represents an alkyl group having 1 to 5 carbon atoms.

In the general formula (N-01-1) to the general formula (N-01-4), R²³Each independently represents an alkoxy group having 1 to 4 carbon atoms.

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

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-01-3) and a compound represented by the general formula (N-01-4).

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

[ solution 25]

In the general formulae (N-02-1) to (N-02-3), R²⁴Each independently represents an alkyl group having 1 to 5 carbon atoms.

In the general formulae (N-02-1) to (N-02-3), R²³Each independently represents an alkoxy group having 1 to 4 carbon atoms.

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

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

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-02-1) and a compound represented by the general formula (N-01-4).

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

[ solution 26]

In the general formula (N-03-1), R²⁴Represents an alkyl group having 1 to 5 carbon atoms.

In the general formula (N-03-1), R²³Represents an alkoxy group having 1 to 4 carbon atoms.

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

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

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

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-03-1), a compound represented by the general formula (N-01-4), and a compound represented by the general formula (N-02-1).

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

[ solution 27]

In the general formula (N-04-1), R²⁴Represents an alkyl group having 1 to 5 carbon atoms.

In the general formula (N-04-1), R²³Represents an alkoxy group having 1 to 4 carbon atoms.

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

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-04-1), a compound represented by the general formula (N-01-4), and a compound represented by the general formula (N-02-1).

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

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-04-1), a compound represented by the general formula (N-02-1), and a compound represented by the general formula (N-03-1).

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains a compound represented by the general formula (N-04-1), a compound represented by the general formula (N-01-4), a compound represented by the general formula (N-02-1), and a compound represented by the general formula (N-03-1).

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

[ solution 28]

The preferable lower limit of the total content of the liquid crystal compound represented by the general formula (N-01) in 100% by mass of the liquid crystal composition containing a polymerizable compound 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, and 80% by mass.

The preferable upper limit of the total content of the liquid crystal compound represented by the general formula (N-01) in 100% by mass of the liquid crystal composition containing a polymerizable compound is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, 20% by mass, 15% by mass, and 10% by mass.

The preferable lower limit of the total content of the liquid crystal compound represented by the general formula (N-02) in 100% by mass of the liquid crystal composition containing a polymerizable compound 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, and 80% by mass.

The preferable upper limit of the total content of the liquid crystal compound represented by the general formula (N-02) in 100% by mass of the liquid crystal composition containing a polymerizable compound is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, 20% by mass, 15% by mass, and 10% by mass.

The preferable lower limit of the total content of the liquid crystal compound represented by the general formula (N-03) in 100% by mass of the liquid crystal composition containing a polymerizable compound 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, and 80% by mass.

The preferable upper limit of the total content of the liquid crystal compound represented by the general formula (N-03) in 100% by mass of the liquid crystal composition containing a polymerizable compound is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, 20% by mass, 15% by mass, and 10% by mass.

The preferable lower limit of the total content of the liquid crystal compound represented by the general formula (N-04) in 100% by mass of the liquid crystal composition containing a polymerizable compound 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, and 80% by mass.

The preferable upper limit of the total content of the liquid crystal compound represented by the general formula (N-04) in 100% by mass of the liquid crystal composition containing a polymerizable compound is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, 20% by mass, 15% by mass, and 10% by mass.

The preferable lower limit of the total content of the liquid crystal compound represented by the general formula (N-05) in 100% by mass of the liquid crystal composition containing a polymerizable compound is 0% by mass, 2% by mass, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, and 20% by mass.

The preferable upper limit value of the total content of the liquid crystal compound represented by the general formula (N-05) in 100% by mass of the liquid crystal composition containing a polymerizable compound 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.

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more compounds selected from the group of compounds represented by general formulae (NU-01) to (NU-08).

[ solution 29]

In the general formulae (NU-01) to (NU-08), 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^NU81And R^NU82Each independently represents any one of 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, and one or two or more-CH groups which are not adjacent to each other₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-.

As 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^NU81And R^NU82Preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms. When importance is attached to the response speed, R is preferable^NU11、R^NU21、R^NU41And R^NU51At least one of the above groups is an alkenyl group having 2 to 3 carbon atoms.

In more detail, R^NU11、R^NU12、R^NU31、R^NU41、R^NU51、R^NU61、R^NU71、R^NU81Particularly preferably an alkyl group having 1 to 5 carbon atoms, R^NU12、R^NU22、R^NU32、R^NU42、R^NU52、R^NU62、R^NU72And R^NU82Particularly preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.

Examples of the alkenyl group having 2 to 3 carbon atoms include those represented by the formulae (R1) to (R5), and preferably those represented by the formula (R1) or (R2).

[ solution 30]

(Black dots in the formulae represent carbon atoms in the ring structure.)

The upper limit of the total content of the liquid crystal compound having an alkenyl group selected from the group of compounds represented by the general formulae (NU-01) to (NU-08) is preferably 30% by mass or less, preferably 25% by mass or less, preferably 20% by mass or less, preferably 15% by mass or less, preferably 10% by mass or less, preferably 5% by mass or less, based on 100% by mass of the polymerizable compound-containing liquid crystal composition. In addition, when importance is attached to a high Voltage Holding Ratio (VHR), it is preferably 10% by mass or less, preferably 5% by mass or less, preferably 1% by mass or less, and preferably not included.

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

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

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

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

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

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

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

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

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

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

The liquid crystal composition of the present invention more preferably contains a compound represented by the general formula (NU-01). Here, in the general formula (NU-01), R^NU51Particularly preferably an alkyl group having 1 to 5 carbon atoms, R^NU52Particularly preferably an alkyl group having 1 to 5 carbon atoms.

The liquid crystal composition of the present invention more preferably contains a compound represented by the general formula (NU-01) and a compound represented by the general formula (NU-05). Here, in the general formula (NU-01), R^NU51Particularly preferably an alkyl group having 1 to 5 carbon atoms, R^NU52Particularly preferably an alkyl group having 1 to 5 carbon atoms.

The liquid crystal composition of the present invention more preferably contains a compound represented by the general formula (NU-01), a compound represented by the general formula (NU-02), and a compound represented by the general formula (NU-05). Here, in the general formula (NU-01), R^NU51Particularly preferably an alkyl group having 1 to 5 carbon atoms, R^NU52Particularly preferably an alkyl group having 1 to 5 carbon atoms.

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

The preferable range of the total content of the liquid crystal compound represented by the general formula (NU-01) in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 1% by mass to 60% by mass, preferably 10% by mass to 50% by mass, and preferably 20% by mass to 40% by mass.

The preferable range of the total content of the liquid crystal compound represented by the general formula (NU-02) in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 1% by mass to 40% by mass, preferably 5% by mass to 25% by mass, and preferably 5% by mass to 20% by mass.

The preferable range of the total content of the liquid crystal compound represented by the general formula (NU-03) in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 1% by mass to 30% by mass, preferably 1% by mass to 20% by mass, and preferably 3% by mass to 15% by mass.

The preferable range of the total content of the liquid crystal compound represented by the general formula (NU-04) in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 0% by mass to 30% by mass, preferably 0% by mass to 20% by mass, and preferably 0% by mass to 10% by mass.

The preferable range of the total content of the liquid crystal compound represented by the general formula (NU-05) in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 1% by mass to 30% by mass, preferably 1% by mass to 20% by mass, and preferably 3% by mass to 20% by mass.

The preferable range of the total content of the liquid crystal compound represented by the general formula (NU-06) in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 0% by mass to 30% by mass, preferably 0% by mass to 20% by mass, and preferably 0% by mass to 10% by mass.

The preferable range of the total content of the liquid crystal compound represented by the general formula (NU-07) in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 0% by mass to 30% by mass, preferably 0% by mass to 20% by mass, and preferably 0% by mass to 20% by mass.

The preferable range of the total content of the liquid crystal compound represented by the general formula (NU-08) in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 0% by mass to 30% by mass, preferably 0% by mass to 20% by mass, and preferably 0% by mass to 10% by mass.

The polymerizable compound-containing liquid crystal composition of the present invention may contain one or more compounds having positive dielectric anisotropy as described in paragraphs 0236 to 0509 of Japanese patent application No. 6233550.

The polymerizable compound-containing liquid crystal composition of the present invention is preferably free of a compound having a structure in which oxygen atoms are bonded to each other, such as a peracid (-CO-OO-) structure, in the molecule.

In the polymerizable compound-containing liquid crystal composition of the present invention, when importance is attached to stability against UV irradiation, the total content of the compounds substituted with chlorine atoms in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably 15% by mass or less, preferably 10% by mass or less, preferably 8% by mass or less, preferably 5% by mass or less, preferably 3% by mass or less, and preferably substantially none.

The polymerizable compound-containing liquid crystal composition of the present invention is preferably a liquid crystal compound containing a large number of intramolecular ring structures all of which are six-membered rings.

The preferable range of the total content of the liquid crystal compounds having all six-membered rings in the intramolecular ring structure in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably 80% by mass or more, preferably 90% by mass or more, preferably 95% by mass or more, and the polymerizable compound-containing liquid crystal composition of the present invention is preferably constituted by substantially only the compounds having all six-membered rings in the intramolecular ring structure.

In order to suppress deterioration of the polymerizable compound-containing liquid crystal composition due to oxidation, the polymerizable compound-containing liquid crystal composition of the present invention preferably has a reduced content of the compound having a cyclohexenylene group as a ring structure, and the total content of the cyclohexenylene group-containing compounds in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably 10% by mass or less, preferably 8% by mass or less, preferably 5% by mass or less, preferably 3% by mass or less, and preferably substantially none.

Attention is paid to improvement of viscosity and T of a polymerizable compound-containing liquid crystal composition_NIIn the case of the improvement of (2), the polymerizable compound-containing liquid crystal composition of the present invention is preferably reduced in the content of a compound having a 2-methylbenzene-1, 4-diyl group in which a hydrogen atom may be substituted with a halogen in the molecule.

The preferable range of the total content of the compound having 2-methylbenzene-1, 4-diyl in the molecule in 100% by mass of the liquid crystal composition containing a polymerizable compound is preferably 10% by mass or less, preferably 8% by mass or less, preferably 5% by mass or less, preferably 3% by mass or less, and preferably substantially not contained.

Further, "substantially not containing" means not containing except for an unintentionally contained substance.

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

[4] Additive agent

The polymerizable compound-containing liquid crystal composition of the present invention may contain an antioxidant, an ultraviolet absorber, a light stabilizer, an infrared absorber, or the like. Among them, the polymerizable compound-containing liquid crystal composition of the present invention preferably contains an antioxidant so that polymerization does not occur in a heating treatment which is one of the steps of manufacturing a liquid crystal display element.

The antioxidant is preferably an antioxidant represented by the general formula (H-1) to (H-4).

[ solution 31]

The lower limit of the total content of the antioxidants in 100% by mass of the liquid crystal composition containing the polymerizable compound is preferably 10 ppm by mass, preferably 20 ppm by mass, preferably 50ppm by mass, and the upper limit thereof is preferably 10000 ppm by mass, preferably 1000 ppm by mass, preferably 500 ppm by mass, preferably 100 ppm by mass.

In the general formula (H-1) to the general formula (H-3), R^H1Each independently represents an alkyl group having 3 to 7 carbon atoms.

More specifically, R of the formula (H-1)^H1Represents an alkyl group having 7 carbon atoms. R of the formula (H-2)^H1Represents an alkyl group having 3 carbon atoms. R of the formula (H-3)^H1Represents an alkyl group having 3 carbon atoms.

In the general formula (H-4), M^H1Represents an alkylene group having 4 to 10 carbon atoms (one or two or more-CH groups which are not adjacent to each other in the above-mentioned group)₂The radicals may not be directly adjacent to oxygen atomsWherein the substituent is-COO-or-OCO-, a single bond, 1, 4-phenylene (any hydrogen atom in the 1, 4-phenylene may be substituted with a fluorine atom), or trans-1, 4-cyclohexylene.

The alkylene group having 4 to 10 carbon atoms has 4 to 10 carbon atoms, preferably 4 to 8 carbon atoms.

Examples of the alkylene group having 4 to 10 carbon atoms include 1, 8-octylene group and the like.

In the polymerizable compound-containing liquid crystal composition of the present invention, a polymerization initiator may be added for the purpose of rapidly polymerizing the polymerizable compound. The polymerization initiator is preferably a photopolymerization initiator.

Examples of the photopolymerization initiator include: diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzildimethylketal, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) one, acetophenone systems such as 1-hydroxycyclohexyl-phenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone, 4 '-phenoxyacetophenone, and 4' -ethoxyacetophenone; benzoin systems such as benzoin, benzoin isopropyl ether, benzoin isobutyl ether, benzoin methyl ether, and benzoin ethyl ether; acylphosphine oxide systems such as 2,4, 6-trimethylbenzoyldiphenylphosphine oxide; benzil and methylphenylglyoxylate; benzophenone-series such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4,4' -dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4 ' -methyl-diphenylsulfide, acrylated benzophenone, 3',4,4' -tetrakis (t-butylperoxycarbonyl) benzophenone, 3' -dimethyl-4-methoxybenzophenone, 2, 5-dimethylbenzophenone, and 3, 4-dimethylbenzophenone; thioxanthone systems such as 2-isopropylthioxanthone, 2, 4-dimethylthioxanthone, 2, 4-diethylthioxanthone and 2, 4-dichlorothioxanthone; aminobenzophenone systems such as milone and 4,4' -diethylaminobenzophenone; 10-butyl-2-chloroacridone, 2-ethylanthraquinone, 9, 10-phenanthrenequinone, camphorquinone, and the like.

The upper limit of the total content of the photopolymerization initiators in the polymerizable compound-containing liquid crystal composition is preferably 100 mass ppm, preferably 56 mass ppm, preferably 48 mass ppm, and preferably 36 mass ppm, based on 100 mass% of the polymerizable compound-containing liquid crystal composition.

[5] Liquid crystal composition containing polymerizable compound

The polymerizable compound-containing liquid crystal composition of the present invention can be produced by, for example, mixing the polymerizable compound (PI), the polymerizable compound (PII), the liquid crystal composition used for the polymerizable compound-containing liquid crystal composition, and additives as needed.

Nematic phase-isotropic liquid phase transition temperature (T) of liquid crystal composition used in liquid crystal composition containing polymerizable compound_NI) Preferably 60 ℃ to 120 ℃, preferably 70 ℃ to 100 ℃, and preferably 70 ℃ to 85 ℃. In the present invention, T represents 60 ℃ or higher_NIHigh.

In the case of liquid crystal television applications, T_NIPreferably 70 to 80 ℃ and T in the case of mobile use_NIPreferably 80 ℃ to 90 ℃, and T is used for outdoor Display such as Public Information Display (PID)_NIPreferably from 90 ℃ to 110 ℃.

The refractive index anisotropy (Delta n) of the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition at 20 ℃ is preferably 0.08 to 0.14, preferably 0.09 to 0.13, and preferably 0.09 to 0.12. More specifically, the thickness is preferably 0.10 to 0.13 in the case of a thin cell gap, and preferably 0.08 to 0.10 in the case of a thick cell gap. The liquid crystal composition used in the liquid crystal composition containing the polymerizable compound preferably has a refractive index anisotropy (Δ n) of 0.098 to 0.118 at 20 ℃.

The rotational viscosity (. gamma.1) at 20 ℃ of the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition is preferably 50 to 160 mPas, preferably 55 to 160 mPas, preferably 60 to 160 mPas, preferably 80 to 150 mPas, preferably 90 to 140 mPas, preferably 90 to 130 mPas, preferably 90 to 115 mPas.

The liquid crystal composition used in the liquid crystal composition containing the polymerizable compound preferably has a dielectric anisotropy (. DELTA.. di-elect cons.) at 20 ℃ of-1.7 to-4.5, preferably-2.5 to-4.3, preferably-2.7 to-4.0, preferably-2.6 to-3.9.

B. Liquid crystal display element

Next, a liquid crystal display device in which a polymer obtained by polymerizing the polymerizable compound is present as a polymer network in the liquid crystal composition containing the polymerizable compound sandwiched between two transparent substrates each having at least one electrode will be described.

More specifically, the liquid crystal display element of the present invention is a liquid crystal display element comprising two transparent substrates having at least one electrode, and the polymerizable compound-containing liquid crystal composition described above sandwiched between the two transparent substrates and polymerized, wherein a polymer obtained by polymerizing the polymerizable compound is present in the polymerizable compound-containing liquid crystal composition as a polymer network.

Examples of the polymerization treatment include ultraviolet irradiation.

According to the liquid crystal display element of the present invention, by using the polymerizable compound-containing liquid crystal composition described in the above "a.

The liquid crystal display element of the present invention preferably has an alignment layer for aligning the polymerizable compound-containing liquid crystal composition on at least one transparent substrate. And applying a voltage to the alignment layer provided on the substrate and the electrode provided on the substrate to control the alignment of the liquid crystal molecules. Further, it is preferable that the polymer network has uniaxial refractive index anisotropy, and the optical axis direction or easy orientation axis direction of the polymer network is the same direction as the easy orientation axis direction of the liquid crystal composition containing the polymerizable compound.

In addition, it is preferable that the easy alignment axis direction of the alignment layer is the same as the easy alignment axis direction of the polymer network.

Preferably, the polymer network layer is formed to have a thickness of 0.5% or more of the cell thickness in the cell cross section.

The liquid crystal layer is formed in a liquid crystal such that the optical axis direction of a polymer network having refractive index anisotropy forms a pretilt angle with respect to a substrate surface by applying an alternating current electric field to a liquid crystal composition containing a polymerizable compound in a temperature range of-50 ℃ to 50 ℃ while irradiating ultraviolet rays or electron beams. By providing a polarizing plate, a retardation film, or the like, display is performed by utilizing the orientation state thereof.

The cell structure of the liquid crystal display element is preferably a Vertical Alignment (VA) mode, an In-Plane Switching (IPS) mode, a Fringe Field Switching (FFS) mode, a Vertical Alignment-Twisted Nematic (VA-TN) mode, a Twisted Nematic (TN) mode, or an Electrically Controlled Birefringence (ECB) mode.

The liquid crystal display element of the present invention is different from a Polymer Stabilized Alignment (PSA) type liquid crystal display element having a Polymer or copolymer on an Alignment film, in that the Polymer or copolymer is contained in a liquid crystal composition.

The two substrates used in the liquid crystal display device of the present invention may be made of glass or a transparent material having flexibility such as plastic. The transparent substrate having a transparent electrode layer can be obtained by, for example, sputtering Indium Tin Oxide (ITO) on a transparent substrate such as a glass plate.

The liquid crystal display device of the present invention may include various components constituting a general liquid crystal display device, such as a color filter, a pixel electrode, a spacer, and a polarizing plate. The liquid crystal display element of the present invention can be manufactured by a conventional method, and can be manufactured by a method disclosed in, for example, japanese patent No. 6090482 and international publication No. 2017/027272.

The present invention is not limited to the above embodiments. The above-described embodiments are illustrative, and any embodiments having substantially the same configuration as the technical idea described in the claims of the present invention and having the same operation and effect are included in the technical scope of the present invention.

[ examples ]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. In the compositions of examples and comparative examples below, "%" means "% by mass".

In the examples, the measured properties of the liquid crystal compositions are as follows.

T_ni: nematic phase-isotropic liquid phase transition temperature (. degree.C.)

Δ n: refractive index anisotropy at 20 DEG C

n_o: ordinary refractive index at 20 DEG C

Δ ε: dielectric anisotropy at 20 DEG C

γ₁: rotational viscosity (mPa. s) at 20 DEG C

(Voltage-transmittance characteristic)

The evaluation characteristics in the examples and comparative examples are the following symbols and contents, respectively.

T0: the transmittance [% ] when the applied voltage is zero represents the magnitude of the black level important for the contrast, and the smaller the value, the better the black level and the larger the contrast.

T100: light transmittance (% by mass) when light transmittance hardly changes with increase in applied voltage

V90: the difference between T100 and T0 was defined as the total change in light transmittance, and the applied voltage [ V ] at which the light transmittance was 90% was used

The voltage was measured by applying a voltage in the range of 0 to 40 volts using a 60Hz square wave, and the transmittance change was used as the voltage-transmittance characteristic.

(response characteristics)

toff: the off response toff was measured as the time of the transmittance change occurring between the voltage V90 and zero volts by a burst wave due to a rectangular wave with a switching response time of 60Hz, in which the applied transmittance was changed from the bright field state formed by the applied voltage V90 to the dark field state with the applied voltage zero.

(Change in Angle of Tilt)

First, the pretilt angle of the liquid crystal display element was measured as the pretilt angle (initial stage). Next, after applying a rectangular voltage of 30V at a frequency of 100Hz to the liquid crystal display element while maintaining for 3 hours, the pretilt angle was measured as the pretilt angle (after the test). The value obtained by subtracting the pretilt angle (after the test) from the measured pretilt angle (initial value) was defined as the tilt angle change (═ absolute value of pretilt angle change) [ ° ]. The pretilt angle is measured using a pretilt angle measurement system ("OPTIPRO") manufactured by Shintech corporation. The magnitude of the applied voltage (30V) is several times larger than the normal drive voltage, and this evaluation test is an accelerated test.

(liquid Crystal composition used for liquid Crystal composition containing polymerizable Compound)

Liquid crystal composition used for polymerizable compound-containing liquid crystal composition: LCN-1

A liquid crystal composition used for a polymerizable compound-containing liquid crystal composition having the following composition was prepared and used. In addition, "%" means "% by mass".

[ solution 32]

T of the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition_ni(nematic phase-isotropic liquid phase transition temperature) 75.6 (DEG C.), DELTA.n (refractive index anisotropy) 0.120, and n_oThe refractive index (ordinary refractive index) was 1.491, Δ ∈ (dielectric anisotropy) was-2.7, γ₁(rotational viscosity) was 100 (mPas).

The following antioxidant was added in an amount of 50ppm to the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition to prepare a liquid crystal composition LCN-1.

[ solution 33]

(examples 1 to 31)

Polymerizable compound-containing liquid crystal compositions (LCNP-1) to polymerizable compound-containing liquid crystal compositions (LCNP-31) shown in tables 1 to 6 were prepared by mixing a polymerizable compound and a liquid crystal composition used for the polymerizable compound-containing liquid crystal composition.

The structure of the polymerizable compound used is shown below.

[ chemical 34]

[ Table 1]

[ Table 2]

[ Table 3]

[ Table 4]

[ Table 5]

[ Table 6]

Comparative examples 1 to 7

The polymerizable compound-containing liquid crystal compositions (LCNP-R1) to the polymerizable compound-containing liquid crystal compositions (LCNP-R7) shown in tables 7 and 8 were prepared by mixing the polymerizable compound and the liquid crystal compositions not containing the polymerizable compound. In comparative example 7, a liquid crystal composition containing no polymerizable compound was used as it is.

[ Table 7]

[ Table 8]

(example 32 to example 62)

In a Vertical Alignment (VA) cell having a cell gap of 3.4 μm and two transparent substrates coated with a polyimide vertical alignment film and having electrodes, a polymerizable compound-containing liquid crystal composition (LCNP-1) to a polymerizable compound-containing liquid crystal composition (LCNP-31) were injected into the cell by vacuum injection. The polyimide vertical alignment films of two transparent substrates having electrodes were subjected to rubbing alignment treatment so that the pretilt angle became 3 °, and the upper and lower transparent substrates were arranged in an antiparallel alignment in the cell.

The illuminance measured by irradiating a high-pressure mercury lamp with a filter for cutting off ultraviolet rays having a wavelength of 325nm or less at a central wavelength of 365nm is set to 90mW/cm²The cumulative quantity of light was 10J/cm²Ultraviolet rays of (1). Subsequently, the illuminance measured by further irradiation with a fluorescent UV lamp at a central wavelength of 313nm was set to 3mW/cm²The cumulative quantity of light was 3.6J/cm²The ultraviolet ray of (2) to obtain a liquid crystal display element. When the cell is placed between two orthogonal polarizers, it will be blackened and the dark field will not change even if the cell is rotated in the azimuth directionAs a result, it was confirmed that the optical axis direction of the polymer network and the easy alignment axis direction of the liquid crystal were the same direction.

The resulting liquid crystal display element was disposed such that the rubbing direction between two polarizing plates orthogonal to the transmission axis was at an angle of 45 ° to the transmission axis. In this state, toff as a response characteristic and T100 as a voltage-transmittance characteristic were measured. In addition, the change in tilt angle is also measured separately.

Subsequently, the two substrates constituting the cell were peeled off, and the liquid crystal adhered to the surfaces of the substrates was washed with hexane. The polymer network on the surface of the substrate was observed by a scanning electron microscope, and as a result, the polymer network having a height of 0.5 μm or more was observed.

The measured toff, T100 and tilt angle changes are shown in the table.

[ Table 9]

[ Table 10]

[ Table 11]

[ Table 12]

[ Table 13]

[ Table 14]

(comparative examples 7 to 13)

Liquid crystal display elements were produced in the same manner as in examples 32 to 62, and toff, T100, and tilt angle changes were measured. In comparative example 13, only toff and T100 were measured. The results are shown in the table.

[ Table 15]

[ Table 16]

As can be seen from comparison of examples 32 to 62 with comparative examples 7, 8, 10 and 11 in which the mass ratio (PII/PI) of the total content of the polymerizable compounds represented by the general formula (PII) to the total content of the polymerizable compounds represented by the general formula (PI) is less than 0.25, even when the same off-response speed is obtained, the tilt angle change can be suppressed to 0.2 ° or less by using the polymerizable compound-containing liquid crystal composition of the present invention.

Further, as is clear from comparison of examples 32 to 62 with comparative examples 9 and 12 in which the total content of the polymerizable compounds represented by the general formula (PII) exceeds 1.4% by mass, even when the same off-response speed is obtained, the use of the polymerizable compound-containing liquid crystal composition of the present invention can suppress the change in tilt angle to 0.2 ° or less and achieve high transmittance at the same time.

Claims

1. A polymerizable compound-containing liquid crystal composition having a negative dielectric anisotropy, comprising:

one or more polymerizable compounds represented by the following general formula (PI);

in the general formula (PI), the compound is represented by the general formula (PI),

in the general formula (R-1) to the general formula (R-9),

p, t and q each independently represent 0, 1 or 2,

is represented by¹¹Or S¹²The bonding point of (a) is (b),

S¹¹and S¹²Each independently represents a single bond or an alkylene group having 1 to 15 carbon atoms, but S¹¹And S¹²Not simultaneously represent a single bond, one or two or more-CH groups which are not adjacent to each other in the alkylene group₂Independently via-O-or via-O-in such a way that the oxygen atoms are not directly adjacent,-OCO-or-COO-substitution

In the general formula (PII) in which,

n²¹represents a number of 0, 1 or 2,

A²¹represents a group selected from the group consisting of (a), (b) and (c),

(a)1, 4-cyclohexylene radical, in which one of the radicals-CH present is₂-or two or more-CH's which are not contiguous₂-may be substituted by-O-

(b)1, 4-phenylene, wherein one or two or more-CH-which are not adjacent to each other present in the group may be substituted by-N ═

(c) Naphthalenediyl, 1,2,3, 4-tetrahydronaphthalenediyl or decahydronaphthalenediyl, wherein one or two or more noncontiguous-CH groups present in naphthalenediyl or 1,2,3, 4-tetrahydronaphthalenediyl may be substituted by-N ═

L²¹represents a single bond, -OCH₂-、-CH₂O-、-C₂H₄-、-OC₂H₄O-、-COO-、-OCO-、-CH＝CR^a-COO-、-CH＝CR^a-OCO-、-COO-CR^a＝CH-、-OCO-CR^a＝CH-、-(CH₂)_z-COO-、-(CH₂)_z-OCO-、-OCO-(CH₂)_z-、-COO-(CH₂)_z-、-CH＝CH-、-CF₂O-、-OCF₂-or-C ≡ C-,

z independently represents an integer of 1 to 4,

in the general formula (N-01) to the general formula (N-05),

m independently represents 1 or 2,

the total content of the polymerizable compounds represented by the general formula (PII) is 0.6 to 1.4 mass%, and the mass ratio of the total content of the polymerizable compounds represented by the general formula (PII) to the total content of the polymerizable compounds represented by the general formula (PI), that is, the general formula (PII)/general formula (PI), is 0.25 or more.

2. The polymerizable compound-containing liquid crystal composition according to claim 1, wherein the total content of the polymerizable compound represented by the general formula (PI) and the polymerizable compound represented by the general formula (PII) is 2.25 to 7.0% by mass.

3. The polymerizable compound-containing liquid crystal composition according to claim 1 or 2, further comprising a photopolymerization initiator.

4. A liquid crystal display element, wherein a polymer obtained by polymerizing the polymerizable compound according to claim 1 is present in a polymer network in the polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 3 sandwiched between two transparent substrates each having an electrode.

5. The liquid crystal display element according to claim 4, wherein at least one transparent substrate has an alignment layer for aligning the polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 3.

6. The liquid crystal display element according to claim 4 or 5, wherein the polymer network has uniaxial refractive index anisotropy, and an optical axis direction or an easy-alignment axis direction of the polymer network is the same direction as an easy-alignment axis direction of the liquid crystal composition containing a polymerizable compound.

7. The liquid crystal display element according to claim 4 or 5, wherein a polymer network layer having a thickness of 0.5% or more of a cell thickness is formed in a cell cross section.

8. The liquid crystal display element according to claim 4 or 5, wherein a cell structure of the liquid crystal display element is a vertical alignment mode, an in-plane switching mode, a fringe field switching mode, a vertical alignment-twisted nematic mode, a twisted nematic mode, or an electrically controlled birefringence mode.