WO2017110494A1

WO2017110494A1 - Nematic liquid crystal composition and liquid crystal display element using same

Info

Publication number: WO2017110494A1
Application number: PCT/JP2016/086519
Authority: WO
Inventors: 麻里奈後藤; 須藤　豪
Original assignee: Dic株式会社
Priority date: 2015-12-21
Filing date: 2016-12-08
Publication date: 2017-06-29
Also published as: JPWO2017110494A1; JP6255637B2

Abstract

[Problem] The present invention addresses the problem of providing a liquid crystal composition that is highly compatible with other liquid crystal compositions, exhibits a sufficiently high Δn, and has a sufficiently small γ1. The present invention also addresses the problem of providing: a polymerizable-compound-containing liquid crystal composition that is highly compatible with other liquid crystal compositions, that exhibits a sufficiently high Δn, that has a sufficiently small γ1, in which the polymerizable compound has a sufficiently high reaction rate, and with which residues of the polymerizable compound after UV radiation are sufficiently inhibited; and a liquid crystal display element of PSA type or the like, which uses the composition, has a sufficiently high response speed, is capable of performing 3D display, and in which uniform and stable alignment control is obtained at lower energy cost. [Solution] Provided are: a liquid crystal composition containing one or more compounds selected from compounds represented by general formula (I); and a liquid crystal display element using the liquid crystal composition.

Description

Nematic liquid crystal composition and liquid crystal display device using the same

The present invention relates to a nematic liquid crystal composition and a liquid crystal display device using the same.

As a display method of a liquid crystal display element used for a clock, a calculator, various measuring instruments, an automobile panel, a printer, a computer, a television, a clock, an advertisement display board, and the like, TN (twisted Nematic) type, STN (super twisted nematic) type, VA (hereinafter also referred to as vertical alignment) type using TFT (thin film transistor), IPS (in-plane switching) type, FFS (fringe field switching) type There are types. A liquid crystal composition having a negative dielectric anisotropy (Δε) is generally used for a VA type widely used for a liquid crystal TV and the like, a TN type used for a PC monitor, a touch panel, etc. In general, a liquid crystal composition having a positive Δε is generally used for the IPS type widely used in the field. There is a demand for a liquid crystal composition that exhibits low voltage driving, high-speed response, and a wide operating temperature range in all driving methods, not limited to these IPS and VA types. In order to meet such requirements, a liquid crystal composition having a large absolute value Δε, a small viscosity (η), and a high nematic phase-isotropic liquid phase transition temperature (Tni) is required. Further, from the setting of Δn × d, which is the product of refractive index anisotropy (Δn) and cell gap (d), it is necessary to adjust Δn of the liquid crystal composition to an appropriate range according to the cell gap. When a liquid crystal display element is applied to a television, a display, or the like, high-speed response is important, and therefore a liquid crystal composition having a larger Δn and a smaller rotational viscosity (γ1) than the current one is required. Therefore, at present, development of a liquid crystal composition that achieves a high Δn with a relatively low viscosity is desired.

For example, Patent Document 1 is cited as a technique focusing on a liquid crystal compound having a naphthalene ring in order to prepare a liquid crystal composition exhibiting a high Δn among properties required for a liquid crystal composition. The patent document 1 discloses various liquid crystal compositions having negative or positive Δε including a liquid crystal compound having a naphthalene ring, and describes that display characteristics are improved by a liquid crystal material having a relatively large Δn. Yes.

In addition, PSA (Polymer Sustained Alignment) technology that controls the pretilt angle of liquid crystal molecules by adding a polymerizable compound to the liquid crystal composition and forming a polymer structure derived from the polymerizable compound in the cell is a high-speed response and It has been put into practical use as a next-generation liquid crystal display element due to features such as high contrast, and is manufactured by polymerizing the polymerizable compound in a state where liquid crystal molecules are aligned by applying voltage and fixing the alignment of liquid crystal molecules. Is. Therefore, in the step of polymerizing the polymerizable compound in the liquid crystal composition used for the PSA type liquid crystal display element, the polymerization reaction rate of the polymerizable compound is very important for productivity. It is also very important to adjust the pretilt angle that affects the response speed and contrast of the PSA type liquid crystal display element and the residual amount of the polymerizable compound that affects the reliability such as display unevenness and image sticking. Furthermore, since the polymerization reaction rate of the polymerizable compound depends on the wavelength and irradiation intensity of the UV irradiation lamp used in the polymerization, the development of a polymerizable compound-containing liquid crystal composition containing the polymerizable compound adapted to the specifications of the UV irradiation lamp Is required. For example, Cited Document 2 specifies a polymerizable compound to be added to a liquid crystal composition on the assumption that the conventional technology has not sufficiently solved problems such as adjustment of the pretilt angle and polymerization reaction rate of the polymerizable compound. It is described that the structure improves compatibility with other liquid crystal compounds, optimizes the polymerization reaction rate of polymerizable compounds, or reduces the amount of unpolymerized polymerizable compounds present after polymerization. .

JP 2001-040354 A International Publication No. 2014/148472 Pamphlet

As shown in the Examples of Patent Document 1 and Patent Document 2, the conventional compounds (A), (B) and (C) having a naphthalene skeleton as described below are used. As a result, the liquid crystal composition has been increased in Δn.

However, although the compound (A) and the compound (B) have a naphthalene ring, the aromatic ring is only a naphthalene ring, and thus a liquid crystal composition having Δn that can satisfy the current requirement has not been realized. In addition, when the compound (A) or the compound (B) is used in a liquid crystal composition containing a polymerizable compound that is a PSA technique, the polymerization rate is slow, which affects the response speed and contrast of the PSA type liquid crystal display device. There arises a problem that the residual amount of the polymerizable compound that affects the reliability such as the pretilt angle to be given, display unevenness and image sticking does not fall within a predetermined range. Further, since the compound (C) is composed of an aromatic ring, it is suitable for increasing the Δn of the liquid crystal composition, but it was confirmed that the compatibility with other liquid crystal compositions is low. In addition, the low-temperature storage stability, which is the degree of precipitation of the liquid crystal compound that occurs when the liquid crystal composition is stored in a low-temperature state, also decreases, and a new problem that the compound (C) precipitates from the liquid crystal composition during low-temperature storage. It has been confirmed that this occurs.

Therefore, the problem to be solved by the present invention is to provide a liquid crystal composition having good compatibility with other liquid crystal compositions. Another problem to be solved by the present invention is to provide a liquid crystal composition exhibiting a sufficiently high Δn and sufficiently small γ1. Another problem to be solved by the present invention is that it has good compatibility with other liquid crystal compositions, exhibits sufficiently high Δn, γ1 is sufficiently small, the reaction rate of the polymerizable compound is sufficiently high, and UV irradiation Provided is a polymerizable compound-containing liquid crystal composition in which the remaining of the polymerizable compound is sufficiently suppressed, and the response speed using the polymerizable compound is sufficiently fast, 3D display is possible, and uniform and stable alignment control is further achieved. An object of the present invention is to provide a liquid crystal display element such as a PSA type which can be obtained with low energy cost.

The present inventors have studied various liquid crystal compounds and various chemical substances, and found that the above problems can be solved by combining specific liquid crystal compounds, and have completed the present invention.

The present invention is a liquid crystal composition excellent in compatibility.
The present invention is a liquid crystal composition exhibiting high Δn and sufficiently low γ1.
The present invention is a liquid crystal composition excellent in low-temperature storage stability.
When the liquid crystal composition of the present invention contains a polymerizable compound, the reaction rate of the polymerizable compound is sufficiently high, and the residue of the polymerizable compound after UV irradiation is sufficiently suppressed.
When the liquid crystal composition of the present invention contains a polymerizable compound, the liquid crystal composition is excellent in compatibility with the polymerizable compound and other liquid crystal compounds, exhibits a high Δn, and has a sufficiently low rotational viscosity (γ1).
When the liquid crystal composition of the present invention contains a polymerizable compound, the pretilt angle can be controlled after polymerization.

The first of the present invention is the general formula (I):

(In the general formula (I), R ^I1 and R ^I2 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, or 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 by a fluorine atom,
L ^I1 and L ^I2 each independently represent a hydrogen atom, a methyl group, a —CF ₃ group, a fluorine atom or a chlorine atom,
A ^I1 and B ^I1 are each independently a trans-1,4-cyclohexylene group (one or non-adjacent two or more —CH ₂ — in the group is substituted by —O— or S—). 1,4-phenylene group (one or two or more non-adjacent —CH═ in the group may be substituted by —N═), 1,4-cyclohexenylene 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, or 1,2, Represents a 3,4-tetrahydronaphthalene-2,6-diyl group, and the hydrogen atom of A ^I1 or B ^I1 may be substituted with a methyl group, a —CF ₃ group, a fluorine atom or a chlorine atom;
One of L ^I1 or L ^I2 is substituted with a methyl group, —CF ₃ group, a fluorine atom or a chlorine atom, or a hydrogen atom of A ^I1 or B ^I1 is a methyl group, —CF ₃ group, fluorine Substituted with an atom or chlorine atom,
m ^I1 represents 0, 1 or 2, and n ^I1 represents 0, 1 or 2. However, when there are a plurality of A ^{I1 s} , they may be different or the same. However, when there are a plurality of ^BI1s , they may be different or the same. Is a liquid crystal composition containing one or more compounds selected from the group of compounds represented by:

The liquid crystal composition according to the present invention exhibits high compatibility and high Δn. In the liquid crystal compound contained in the composition, when a substituent is introduced into the ring, the intermolecular interaction is weakened. Therefore, compatibility with other liquid crystal compounds contained in the composition is increased, and the composition as a whole has high compatibility. Show. Further, when the position and structure of the substituents in the liquid crystal compound contained in the composition are asymmetric, higher compatibility is exhibited.

In the general formula (I), R ^I1 represents an alkyl group having 1 to 5 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms. It preferably represents an oxy group.

In the general formula (I), R ^I2 represents an alkyl group having 1 to 5 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms. It preferably represents an oxy group.

In the present specification, the alkyl group, alkoxy group, alkenyl group or alkenyloxy group may be linear or branched, but is preferably linear. In addition, when the compound contained in the liquid crystal composition according to the present invention has an alkenyl group as a side chain, when the alkenyl group is bonded to cyclohexane, the alkenyl group has 2 to 5 carbon atoms. Preferably, when the alkenyl group is bonded to benzene, the alkenyl group preferably has 4 to 5 carbon atoms, and the unsaturated bond of the alkenyl group and benzene are not directly bonded. It is preferable.

In the above general formula (I), A ^I1 represents 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4 -Phenylene group, 2,3-difluoro-1,4-phenylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2, 3,4-tetrahydronaphthalene-2,6-diyl group is preferred, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro A 1,4-phenylene group and a 2,3-difluoro-1,4-phenylene group are more preferable, and a 1,4-phenylene group is particularly preferable.

In the above general formula (I), B ^I1 represents 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4 -Phenylene group, 2,3-difluoro-1,4-phenylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2, 3,4-tetrahydronaphthalene-2,6-diyl group is preferred, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro A 1,4-phenylene group and a 2,3-difluoro-1,4-phenylene group are more preferable, and a 1,4-phenylene group is particularly preferable.

All of A ^I1 and B ^I1 are preferably aromatic rings because they exhibit high Δn.

The hydrogen atom of ring A ^I1 or B ^{I1 according to} the present invention may be substituted with a substituent. The substituent is preferably one selected from the group consisting of a methyl group, a —CF ₃ group, a fluorine atom and a chlorine atom, and the hydrogen atom of A ^I1 or B ^I1 is a methyl group or a fluorine atom. More preferably it is substituted.

In the general formula (I) according to the present invention, it is preferable that a hydrogen atom of a ring other than the naphthalene ring is substituted with a substituent. The substituent is preferably one or more selected from the group consisting of a methyl group, a —CF ₃ group, a fluorine atom and a chlorine atom.

In the general formula (I) according to the present invention, one or more selected from the group consisting of benzene rings having A ^I1 , B ^I1 and L ^I1 and L ^I2 have a substituent other than a hydrogen atom. The substituent is one or more selected from the group consisting of a methyl group, a —CF ₃ group, a fluorine atom and a chlorine atom. In this case, the number of substituents in each ring is preferably 1 or less.

One or more selected from the group consisting of A ^I1 , B ^I1 and L ^I1 and L ^I2 have a substituent other than a hydrogen atom, and the substituent is a methyl group , -CF ₃ group, is one or more selected from the group consisting of fluorine atom and chlorine atom. In this case, the number of substituents in each ring is preferably 1 or less.

That is, the hydrogen atom of A ^I1 or B ^I1 is substituted with a methyl group, —CF ₃ group, a fluorine atom or a chlorine atom, or one of L ^I1 or L ^I2 is a methyl group, —CF ₃ group, A fluorine atom or a chlorine atom.

Since a compound in which a substituent is introduced into the ring A ^I1 or B ^I1 has a weak intermolecular interaction, compatibility with other liquid crystal compounds is increased. Further, when it is asymmetric, higher compatibility is exhibited.

The number of substituents in ring A ^I1 or B ^I1 is preferably 0 or more and 4 or less, more preferably 0 or more and 2 or less, and particularly preferably 0 or 1.

It is preferable that one or less of the substituents is substituted for one ring A ^I1 or B ^I1 .

m ^I1 represents 0, 1 or 2, and is preferably 0 or 1 when importance is attached to the viscosity, and preferably 1 or 2 when importance is attached to Tni. In order to increase the compatibility with other liquid crystal components, 0 or 1 is preferable. However, when there are a plurality of A ^{I1 s} , they may be different or the same.

n ^I1 represents 0, 1 or 2, and is preferably 0 or 1 when importance is attached to the viscosity, and preferably 1 or 2 when importance is attached to Tni. In order to increase the compatibility with other liquid crystal components, 0 or 1 is preferable. However, when there are a plurality of ^BI1s , they may be different or the same.

m ^I1 + n ^I1 is preferably 0 or 1 when importance is attached to the viscosity, and m ^I1 + n ^I1 is preferably 2 or more when importance is attached to Tni. In order to increase the compatibility, 0 or 1 is preferable, and 1 is more preferable.

L ^I1 and L ^I2 each independently preferably represent a hydrogen atom, a methyl group, a —CF ₃ group or a fluorine atom, and more preferably a hydrogen atom or a fluorine atom.

Further, the number of substituents in ring ^{A I1} or ^{B ^I1,} the sum of the number of substituents other than hydrogen atoms of ^{L I1} and ^{L I2} is preferably from 1 to four, it is 1 to 2 More preferably, one is more preferable. The number of substituents in ring A ^I1 or B ^I1 is 0 (in other words, the hydrogen atom of ring A ^I1 or B ^I1 is unsubstituted), and one of L ^I1 and L ^I2 is a fluorine atom, and the other Is particularly preferably a hydrogen atom.

It is preferable that either one of L ^I1 and L ^I2 is a fluorine atom and the other is a hydrogen atom in terms of compatibility with other liquid crystal compounds and reliability such as VHR.

Preferred embodiments of the compound represented by formula (I) according to the present invention are the following three embodiments.
^{(1) m I1} is 1 or more, and at least one of the hydrogen atoms of the ring of a benzene ring ^{which n l1} is provided with a case ring ^{A I1} and ^{L I1} and ^{L I2} of 0 is substituted with a substituent . In this case, it is preferable that each ring has one substituent (in the compound represented by the general formula (I), one substituent is substituted with one substituent for one ring). There are 1 to 3 rings.) Furthermore, when m ^I1 is 2 or more, the rings A ^I1 may be the same or different, the substituent may be the same or different, and the position of the substituent may be the same or different. good. The substituent preferably represents a hydrogen atom, a methyl group, a —CF ₃ group or a fluorine atom.
(2) When m ^I1 is 0 and n ¹¹ is 1 or more The ring B ^I1 and the hydrogen atom of at least one of the benzene rings provided with L ^I1 and L ^I2 are substituted with a substituent . In this case, it is preferable that each ring has one substituent (in the compound represented by the general formula (I), one substituent is substituted with one substituent for one ring). There are 1 to 3 rings.) Furthermore, when n ^I1 is 2 or more, the rings B ^I1 may be the same or different, the substituent may be the same or different, and the position of the substituent may be the same or different. good. The substituent preferably represents a hydrogen atom, a methyl group, a —CF ₃ group or a fluorine atom.
(3) When m ^I1 is 1 or more and n ¹¹ is 1 or more The hydrogen atom of at least one of the benzene rings having ring A ^I1 , ring B ^I1, and L ^I1 and L ^I2 is a substituent Has been replaced by In this case, it is preferable that each ring has one substituent (in the compound represented by the general formula (I), one substituent is substituted with one substituent for one ring). There are 1 to 5 rings.) Furthermore, when n ^I1 is 2 or more, the rings B ^I1 may be the same or different, the substituent may be the same or different, and the position of the substituent may be the same or different. good. When m ^I1 is 2 or more, the rings A ^I1 may be the same or different, the substituent may be the same or different, and the position of the substituent may be the same or different. The substituent preferably represents a hydrogen atom, a methyl group, a —CF ₃ group or a fluorine atom.

The content of the compound represented by the general formula (I) contained in the liquid crystal composition according to the present invention is preferably 0.1% by mass, preferably 0.3% by mass, and 0.5% by mass as the lower limit. Is preferred, 0.7% by weight is preferred, 1% by weight is preferred, 1.3% by weight is preferred, 1.5% by weight is preferred, 1.8% by weight is preferred, 2% by weight is preferred and 2.3% is preferred. % By mass is preferable, 2.6% by mass is preferable, 2.8% by mass is preferable, 3% by mass is preferable, 3.2% by mass is preferable, 3.5% by mass is preferable, and 3.7% by mass is preferable. 4% by mass is preferable, 4.3% by mass is preferable, 4.5% by mass is preferable, 4.7% by mass is preferable, 5% by mass is preferable, 7% by mass is preferable, and 10% by mass is preferable. % By mass is preferred, and 15% by mass is preferred. As an upper limit, 50 mass% is preferable, 45 mass% is preferable, 43 mass% is preferable, 40 mass% is preferable, 38 mass% is preferable, 36 mass% is preferable, 34 mass% is preferable, 30 mass% is 30 mass%. Preferably, 28% by weight is preferred, 26% by weight is preferred, 24% by weight is preferred, 22% by weight is preferred, 20% by weight is preferred, 18% by weight is preferred, 15% by weight is preferred, 13% by weight is preferred, 10% by mass is preferable, 9% by mass is preferable, 8% by mass is preferable, 7% by mass is preferable, 6% by mass is preferable, 5% by mass is preferable, 4.5% by mass is preferable, and 4.2% by mass is preferable. Preferably, 4% by mass is preferable, 3.8% by mass is preferable, 3.5% by mass is preferable, 3.2% by mass is preferable, 3% by mass is preferable, and 2.8% by mass is preferable. Ku is preferably 2.5 mass%, preferably 2.3% by mass.

General formula (I) according to the present invention is represented by the following general formula (I ′):

(In the above general formula (I ′), L ^I1 to L ^I6 each independently represent a methyl group, —CF ₃ group, fluorine atom or chlorine atom, and any one of L ^I1 , L ^I3 or L ^I5 Or two or any one or two of L ^I2 , L ^I4 or L ^I6 represents a methyl group, a —CF ₃ group or a fluorine atom, and R ^I1 , R ^I2 , m ^I1 and n ^I1 are each represented by the above general formula ( Since it is the same as I), it is omitted.

In the general formula (I ′), when m ^I1 is 1 or more and n ^I1 is 0, either L ^I1 or L ^I3 or either L ^I2 or L ^I4 is a methyl group, —CF _Three groups or fluorine atoms are preferred. In this case, when m ^I1 is 2, a plurality of L ^I3 or L ^I4 may be independently the same or different.

In the general formula (I ′), when m ^I1 is 0 and n ^I1 is 1 or more, either L ^I1 or L ^I5 or either L ^I2 or L ^I6 is a methyl group, —CF _Three groups or fluorine atoms are preferred. In this case, when n ^I1 is 2, a plurality of L ^I5 or L ^I6 may be independently the same or different.

In the general formula (I ′), when m ^I1 is 1 or more and n ^I1 is 1 or more, any one or two of L ^I1 , L ^I3 or L ^I5 or L ^I2 , L ^I4 or L It is preferable that any one or two of ^I6 is a methyl group, a —CF ₃ group or a fluorine atom. In this case, when m ^I1 is 2, a plurality of L ^I3 or L ^I4 may be independently the same or different. When n ^I1 is 2, a plurality of L ^I5 or L ^I6 may be independently the same or different.

In the above general formula (I ′), it is preferable that either L ^I1 or L ^I2 is substituted with 1 or less methyl group, —CF ₃ group or fluorine atom.

In the general formula (I ′), when n ^I1 is 1 or more, it is preferable that either L ^I5 or L ^I6 is substituted with 1 or less methyl group, —CF ₃ group, or fluorine atom.

In the general formula (I ′), a naphthalene ring, a benzene ring provided with L ^I1 and L ^I2 , a benzene ring provided with L ^I3 and L ^I4, and a benzene ring provided with L ^I5 and L ^I6 Four types of rings are described, and one benzene ring other than the naphthalene ring is preferably substituted with 1 or less methyl group, —CF ₃ group or fluorine atom, and the methyl group or fluorine atom is It is more preferable that 1 or less is substituted, and it is more preferable that 1 or less fluorine atom is substituted.

In the general formula (I ′), 1 to 4 of the substituents L ^I1 to L ^I6 are preferably a methyl group, —CF ₃ group, a fluorine atom or a chlorine atom, preferably 1 to 3 methyl groups, -CF ₃ group, more preferably a fluorine atom or a chlorine atom, more preferably 1 to 2 methyl groups, -CF ₃ group, a fluorine atom or chlorine atom, still more preferably 1 methyl group, -CF ₃ group Particularly preferred is a fluorine atom or a chlorine atom.

General formula (I) according to the present invention is represented by general formula (I-1) to general formula (I-9).

(In the above general formulas (I-1) to (I-9), R ^I1 and R ^I2 are as described above), and it may be one or more compounds selected from the group consisting of preferable.

The compounds represented by the general formulas (I-1) to (I-9) are preferable from the viewpoint of exhibiting high Δn, and the chemical structure is asymmetric, so that compatibility with other liquid crystal compounds is achieved. Becomes higher.

The compounds represented by the general formulas (I-1) to (I-9) according to the present invention are dielectrically nearly neutral, such as 3,5-difluoro-1,4-phenylene groups and 2,3-difluoro groups. Compared with a dielectrically positive or negative compound in which two or more fluorine atoms such as 1,4-phenylene group are substituted with a ring structure, the light resistance is superior, so that the backlight or the like is changed over time. Stable to light.

The total content of the compounds represented by general formulas (I-1) to (I-9) contained in the liquid crystal composition according to the present invention is preferably 0.1% by mass as the lower limit, and 0.3% by mass. %, 0.5% by weight is preferred, 1% by weight is preferred, 3% by weight is preferred, 5% by weight is preferred, 7% by weight is preferred, 10% by weight is preferred, 12% by weight is preferred, 15% by weight % Is preferred. As an upper limit, 50 mass% is preferable, 45 mass% is preferable, 43 mass% is preferable, 40 mass% is preferable, 38 mass% is preferable, 36 mass% is preferable, 34 mass% is preferable, 30 mass% is 30 mass%. Preferably, 28% by weight is preferred, 26% by weight is preferred, 24% by weight is preferred, 22% by weight is preferred, 20% by weight is preferred, 18% by weight is preferred, 15% by weight is preferred, 13% by weight is preferred, 10 mass% is preferable.

The compound represented by the general formula (I-1) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-1-1) to (I-1-13), for example. It is preferable that it is 1 type or 2 types or more.

The compound represented by the general formula (I-2) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-2-1) to (I-2-13), for example. It is preferable that it is 1 type or 2 types or more.

The compound represented by the general formula (I-3) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-3-1) to (I-3-12), for example. It is preferable that it is 1 type or 2 types or more.

The compound represented by the general formula (I-4) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-4-1) to (I-4-12), for example. It is preferable that it is 1 type or 2 types or more.

The compound represented by the general formula (I-5) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-5-1) to (I-5-4), for example. It is preferable that it is 1 type or 2 types or more.

The compound represented by the general formula (I-6) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-6-1) to (I-6-4), for example. It is preferable that it is 1 type or 2 types or more.

The compound represented by the general formula (I-7) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-7-1) to (I-7-4), for example. It is preferable that it is 1 type or 2 types or more.

The compound represented by the general formula (I-8) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-8-1) to (I-8-4), for example. It is preferable that it is 1 type or 2 types or more.

The compound represented by the general formula (I-9) according to the present invention is selected from the group consisting of compounds represented by the following formulas (I-9-1) to (I-9-4), for example. It is preferable that it is 1 type or 2 types or more.

Of the compounds of the above general formulas (I-1-1) to (I-9-4), (I-1-1) to (I-2-13) are preferred, and (I-1-2), (I I-1-5), (I-1-8), (I-1-10), (I-2-1), (I-2-6), (I-2-9) and (I- 2-11) is more preferable, and (I-1-2), (I-1-8), (I-2-9) and (I-2-11) are particularly preferable. Compounds such as (I-1-2), (I-1-8), (I-2-9) and (I-2-11) are preferred from the viewpoint of compatibility with other liquid crystal compounds.

The liquid crystal composition according to the present invention preferably contains a polymerizable compound. Since the compound represented by the general formula (I) according to the present invention contains a naphthalene ring essentially, it has a long UV absorption edge wavelength, and has a UV sensitizing effect irradiated during polymerization of the polymerizable compound.

Examples of the polymerizable compound according to the present invention include general formulas (RM-1) and (RM-2):

“In the general formula (RM-1), Z ^M1 and Z ^M2 are represented by the following:

(In the formula (Z ^M1 ), X ^M11 to X ^M15 are each independently one or more selected from the group consisting of a methyl group, a —CF ₃ group, a fluorine atom and a chlorine atom, or a formula (RM -S11), but at least one of X ^M11 to X ^M15 represents the formula (RM-S11).)

(In the formula (Z ^M2 ), X ^M21 to X ^M25 are each independently one or more selected from the group consisting of a methyl group, a —CF ₃ group, a fluorine atom and a chlorine atom, or a formula (RM -S21), but at least one of X ^M21 to X ^M25 represents the formula (RM-S21).)
(In the above formula (RM-S11) and the above formula (RM-S21), S ^M11 and S ^M21 each independently represents an alkylene group having 1 to 12 carbon atoms or a single bond, and — CH ₂ — may be replaced by —O—, —COO—, —OCO—, or —OCOO— as those in which oxygen atoms are not directly bonded to each other,
R ^M11 and R ^M21 each independently represent the following formulas (R-1) to (R-15):

Represents one of the following:
L ^M1 and L ^M2 are each independently a single bond, —O—, —CH ₂ —, —OCH ₂ —, —CH ₂ O—, —CO—, —C ₂ H ₄ —, —COO—, —OCO—, —CH═CH—COO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—OCO—, —COOC ₂ H ₄ —, —OCOC ₂ H ₄ —, _{_{_{_{-C 2 H 4 OCO -, -}}}} C 2 H 4 COO -, - OCOCH 2 -, - CH 2 COO -, - CH = CH -, - CF = CH -, - CH = CF -, - CF = CF- _{_{_{, -CF 2 -, - CF 2}}} O -, - OCF 2 -, - CF 2 CH 2 -, - CH 2 CF 2 -, - CF 2 CF 2 - or -C≡C- ^{represent, L M2} is more If present, they may be the same or different. )
M ^M1 represents a 1,4-phenylene group, a 1,4-cyclohexylene group or a naphthalene-2,6-diyl group, and the hydrogen atom contained in these groups is a fluorine atom, a chlorine atom or a carbon atom An alkyl group of 1-8, halogenated alkyl group, halogenated alkoxy group, alkoxy group, nitro group or

( ^Wherein S ^M1 represents an alkylene group having 1 to 12 carbon atoms or a single bond, and —CH ₂ — in the alkylene group represents an oxygen atom, —COO—, — OCO— or —OCOO— may be substituted, and R ^M1 represents any of the above formulas (R-1) to (R-15).
May be optionally substituted, if M ^M1 there are a plurality, they may be the same or different,
m ^M1 represents 0, 1 or 2.

When there are a plurality of S ^M11 , S ^M21 , S ^M1 , R ^M11 , R ^M21 and / or R ^M1 , they may be the same or different. "

“In the general formula (RM-2), X ^M1 to X ^M8 each independently represents a hydrogen atom or a fluorine atom,
S ^M2 and S ^M3 each independently represents an alkylene group having 1 to 12 carbon atoms or a single bond, and —CH ₂ — in the alkylene group represents an oxygen atom, — May be replaced by COO-, -OCO- or -OCOO-,
R ^M2 and R ^M3 represent any of the above formulas (R-1) to (R-15). It is preferable that it is 1 type, or 2 or more types selected from the group which consists of a polymeric compound represented by this.

In the general formula (RM-1), Z ^M1 represents the general formula (Z ^M1 )

And one or two of X ^M11 to X ^M15 preferably represent the general formula (RM-S11), and more preferably X ^M13 represents the general formula (RM-S11).

In the general formula (RM-1), Z ^M2 represents the general formula (Z ^M2 ).

And one or two of X ^M21 to X ^M25 preferably represent the general formula (RM-S21), and more preferably X ^M23 represents the general formula (RM-S21).
R ^M11 and R ^M21 each independently preferably represent formula (R-1) or formula (R-2).

In the general formula (RM-1), M ^M1 is preferably a 1,4-phenylene group, and the hydrogen atom contained in these groups is a fluorine atom, a chlorine atom or an alkyl having 1 to 8 carbon atoms. Group, a halogenated alkyl group, a halogenated alkoxy group, an alkoxy group, a nitro group or the above general formula (RM-S11).

A polymerizable compound in which M ^M1 is a 1,4-phenylene group has a sufficiently high polymerization rate.

In the general formula (RM-1), L ^M1 and L ^M2 are each independently —OCH ₂ —, —CH ₂ O—, —C ₂ H ₄ —, —COO—, —OCO—, —CH═ CH-COO -, - COO- CH = CH -, - OCO-CH = CH -, - CH = CH-OCO -, - COOC 2 H 4 -, - OCOC 2 H 4 -, - C 2 H 4 OCO- , —C ₂ H ₄ COO—, —CH═CH—, —CF═CH—, —CH═CF—, —CF═CF—, —CF ₂ O—, —OCF ₂ —, —CF ₂ CH ₂ — , —CH ₂ CF ₂ —, —CF ₂ CF ₂ —, —C≡C— or a single bond is preferred. In order to improve compatibility with liquid crystal molecules, L ^M1 and L ^M2 are more preferably an even number of atoms in which the length of the linking group connecting the rings is even.

In the general formula (RM-1), m ^M1 preferably represents 0 or 1. m The polymerizable compound in which ^M1 represents 0 or 1 exhibits high compatibility with other liquid crystal compounds.

In the liquid crystal composition according to the present invention, the content of the polymerizable compound represented by the general formula (RM-1) is 0.01 to 5% by mass with respect to the entire liquid crystal composition, but the lower limit of the content is 0. 0.02% by mass is preferable, 0.03% by mass is preferable, 0.04% by mass is preferable, 0.05% by mass is preferable, 0.06% by mass is preferable, 0.07% by mass is preferable, and 0.08% by mass. % By mass is preferable, 0.09% by mass is preferable, 0.1% by mass is preferable, 0.15% by mass is preferable, 0.2% by mass is preferable, 0.25% by mass is preferable, and 0.3% by mass Is preferable, 0.35% by mass is preferable, 0.4% by mass is preferable, 0.5% by mass is preferable, 0.55% by mass is preferable, and the upper limit of the content is preferably 4.5% by mass, and 4% by mass. % Is preferable, and 3.5% by mass is preferable. 3% by weight is preferred, 2.5% by weight is preferred, 2% by weight is preferred, 1.5% by weight is preferred, 1% by weight is preferred, 0.95% by weight is preferred, 0.9% by weight is preferred, 0.85 mass% is preferable, 0.8 mass% is preferable, 0.75 mass% is preferable, 0.7 mass% is preferable, 0.65 mass% is preferable, 0.6 mass% is preferable, and 55 mass% is preferable.

Specifically, the polymerizable compound represented by the general formula (RM-1) according to the present invention is represented by the following general formula (RM-1-1) and general formula (RM-1-2). It is preferable that it is 1 type (s) or 2 or more types selected from the polymeric compound group.

(In the general formula (RM-1-1) and formula ^{(RM-1-2), R 107} ^is, P ^{107 -S} 107 - ^{represents, R 110} ^is, P ^{110 -S} 110 - represents, P ¹⁰⁷ and P ¹¹⁰ each independently represent any of the above formulas (R-1) to (R-15), and S ¹⁰⁷ and S ¹¹⁰ each independently represent a single bond or a carbon number of 1 to 15 Represents an alkylene group, one or more —CH ₂ — in the alkylene group may be substituted with —O—, —OCO— or —COO— so that the oxygen atom is not directly adjacent;
R ¹⁰⁸ , R ¹⁰⁹ , R ¹¹¹ and R ¹¹² are each independently an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine atom, a hydrogen atom or the above formula (R-1 ) To any one of formulas (R-15)
A ¹⁵ represents 1,4-phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, indane-2, Represents a 5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or a 1,3-dioxane-2,5-diyl group, but the group is unsubstituted or has the number of carbon atoms May be substituted with an alkyl group of 1 to 12, halogen (fluorine atom, chlorine atom), cyano group or nitro group,
L ¹⁵ represents a single _{_{_{_{bond, -OCH 2 -, - CH 2}}}} O -, - C 2 H 4 -, - COO -, - OCO -, - CH = CR a -COO -, - CH = CR a -OCO-, —COO—CR ^a ═CH—, —OCO—CR ^a ═CH—, — (CH ₂ ) _Y —COO—, — (CH ₂ ) _Y —OCO—, —OCO— (CH ₂ ) _Y —, —COO — (CH ₂ ) _Y —, —CH═CH—, —CF ₂ O—, —OCF ₂ —, or —C≡C— (wherein each R ^a is independently a hydrogen atom or 1 carbon atom) Represents an alkyl group of 3, wherein Y represents an integer of 1 to 4),
X ¹⁵ , X ¹⁶ , X ¹⁷ and X ¹⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a fluorine atom. )
In the above general formulas (RM-1-1) and (RM-1-2), S ¹⁰⁷ and S ^{110 each} represents a single bond or an alkylene group having 1 to 6 carbon atoms (one or two of the alkylene groups). One or more -CH 2 _-. is the so oxygen atoms are not directly adjacent, is preferably -O- in may be substituted), is particularly preferably a single bond.

In the above general formula (RM-1-1), A ¹⁵ is 1,4 substituted with an unsubstituted alkyl group having 1 to 12 carbon atoms, halogen (fluorine atom, chlorine atom), cyano group or nitro group. -Preferably a phenylene group or a naphthalene-2,6-diyl group, an unsubstituted 1,4-phenylene group substituted with an alkyl group having 1 to 3 carbon atoms or a fluorine atom, or naphthalene-2,6- More preferred is a diyl group. In this case, the number of substituents of A ¹⁵ is preferably 0-2.

In the above general formula (RM-1-1) and general formula (RM-1-2), L ¹⁵ has an even number of atoms in a single bond or a connecting portion that connects the ring to the ring from the viewpoint of compatibility. (For example, Y is preferably 2 or 4).

In the liquid crystal composition according to the present invention, the content of the polymerizable compound represented by the general formula (RM-1-1) and the general formula (RM-1-2) with respect to the entire liquid crystal composition is 0.01 to 5 The lower limit of the content is preferably 0.02% by mass, preferably 0.03% by mass, preferably 0.04% by mass, preferably 0.05% by mass, and preferably 0.06% by mass. 0.07% by mass, 0.08% by mass is preferable, 0.09% by mass is preferable, 0.1% by mass is preferable, 0.15% by mass is preferable, 0.2% by mass is preferable, and 0% by mass is preferable. .25% by mass is preferable, 0.3% by mass is preferable, 0.35% by mass is preferable, 0.4% by mass is preferable, 0.5% by mass is preferable, and 0.55% by mass is preferable. The upper limit is preferably 4.5% by mass, preferably 4% by mass. 3.5% by mass is preferable, 3% by mass is preferable, 2.5% by mass is preferable, 2% by mass is preferable, 1.5% by mass is preferable, 1% by mass is preferable, and 0.95% by mass is preferable. Preferably, 0.9% by weight is preferred, 0.85% by weight is preferred, 0.8% by weight is preferred, 0.75% by weight is preferred, 0.7% by weight is preferred, 0.65% by weight is preferred, 0.6 mass% is preferable and 0.55 mass% is preferable.

The compound represented by the general formula (RM-1-2) according to the present invention is preferably one or more polymerizable compounds represented by the general formula (IV).

In the general formula (IV), ^{R 7} and ^{R 8} each independently represent any one of the above formulas (R-1) the formula (R-15), ^{X 8} from ^{X 1} are each independently Represents a trifluoromethyl group, a trifluoromethoxy group, a fluorine atom or a hydrogen atom.

The structure of the biphenyl skeleton in the general formula (IV) is more preferably formula (IV-11) to formula (IV-15), and particularly preferably formula (IV-11).

A polymerizable compound containing a skeleton represented by the formulas (IV-11) to (IV-15) has an optimum orientation regulating force after polymerization, and a good orientation state can be obtained.

Specifically, the compound represented by the general formula (RM-1) according to the present invention is preferably a compound represented by the general formula (XX-1) to the general formula (XX-13). More preferred are formulas (XX-7) from 1).

In formula (XX-1) to general formula (XX-13), Sp ^xx represents an alkylene group having 1 to 8 carbon atoms or —O— (CH ₂ ) _s — (wherein s represents an integer of 2 to 7) And an oxygen atom is bonded to the ring).

In formula (XX-1) to general formula (XX-13), the hydrogen atom in the 1,4-phenylene group is further —F, —Cl, —CF ₃ , —CH ₃ , formula (R-1) To any one of formulas (R-15).

In addition, as the compound represented by the general formula (RM-1), for example, polymerizable compounds such as the formula (M1) to the formula (M18) are preferable.

In addition, polymerizable compounds such as formula (M19) to formula (M34) are also preferable.

The hydrogen atoms in the 1,4-phenylene group and naphthalene group in the formulas (M19) to (M34) may be further substituted with —F, —Cl, —CF ₃ , or —CH ₃ .

In addition, polymerizable compounds such as formula (M35) to formula (M65) are also preferable.

In the liquid crystal composition according to the present invention, the content of the polymerizable compound represented by formulas (M1) to (M65) is 0.01 to 5% by mass with respect to the entire liquid crystal composition, but the lower limit of the content Is preferably 0.02 mass%, preferably 0.03 mass%, preferably 0.04 mass%, preferably 0.05 mass%, preferably 0.06 mass%, preferably 0.07 mass%, 0.08% by mass, 0.09% by mass is preferable, 0.1% by mass is preferable, 0.15% by mass is preferable, 0.2% by mass is preferable, 0.25% by mass is preferable, and 0.3% by mass is preferable. % By mass is preferable, 0.35% by mass is preferable, 0.4% by mass is preferable, 0.5% by mass is preferable, 0.55% by mass is preferable, and the upper limit of the content is preferably 4.5% by mass, 4% by mass is preferable, and 3.5% by mass is preferable. 3 mass% is preferable, 2.5 mass% is preferable, 2 mass% is preferable, 1.5 mass% is preferable, 1 mass% is preferable, 0.95 mass% is preferable, and 0.9 mass% is Preferably, 0.85 mass% is preferable, 0.8 mass% is preferable, 0.75 mass% is preferable, 0.7 mass% is preferable, 0.65 mass% is preferable, 0.6 mass% is preferable, 0.55 mass% is preferable.

In the general formula (RM-2), it is preferable that R ^M2 and R ^M3 each independently represent any of the above formulas (R-1) and (R-2).

In the above general formula (RM-2), S ^M2 and S ^M3 are each independently an alkylene group having 1 to 6 carbon atoms (wherein —CH ₂ — in the alkylene group is such that oxygen atoms are not directly bonded to each other). As an oxygen atom, —COO—, —OCO— or —OCOO—) or a single bond is preferable.

In the liquid crystal composition according to the present invention, the content of the polymerizable compound represented by the general formula (RM-2) is 0.01 to 5% by mass with respect to the entire liquid crystal composition, but the lower limit of the content is 0. 0.02% by mass is preferable, 0.03% by mass is preferable, 0.04% by mass is preferable, 0.05% by mass is preferable, 0.06% by mass is preferable, 0.07% by mass is preferable, and 0.08% by mass. % By mass is preferable, 0.09% by mass is preferable, 0.1% by mass is preferable, 0.15% by mass is preferable, 0.2% by mass is preferable, 0.25% by mass is preferable, and 0.3% by mass Is preferable, 0.35% by mass is preferable, 0.4% by mass is preferable, 0.5% by mass is preferable, 0.55% by mass is preferable, and the upper limit of the content is preferably 4.5% by mass, and 4% by mass. % Is preferable, and 3.5% by mass is preferable. 3% by weight is preferred, 2.5% by weight is preferred, 2% by weight is preferred, 1.5% by weight is preferred, 1% by weight is preferred, 0.95% by weight is preferred, 0.9% by weight is preferred, 0.85 mass% is preferable, 0.8 mass% is preferable, 0.75 mass% is preferable, 0.7 mass% is preferable, 0.65 mass% is preferable, 0.6 mass% is preferable, and 55 mass% is preferable.

Preferred examples of the compound represented by the general formula (RM-2) according to the present invention include polymerizable compounds represented by the following formulas (RM-2-1) to (RM-2-52).

The specific content of the polymerizable monomer represented by the above formulas (RM-2-1) to (RM-2-52) is preferably 5% by mass or less, more preferably 3% by mass or less. It is more preferably 2% by mass or less, particularly preferably 1% by mass or less, and most preferably 0.8% by mass or less.

The liquid crystal composition according to the present invention preferably exhibits a liquid crystal phase at (25 ° C.), more preferably exhibits a nematic phase, and a nematic liquid crystal composition having a negative dielectric anisotropy is preferable.

The liquid crystal composition according to the present invention preferably contains a liquid crystal compound having a dielectric anisotropy smaller than −2 in addition to the compound represented by the general formula (I). It is more preferable to contain a neutral compound (Δε value is −2 to 2) and a negative compound (Δε value is smaller than −2). The liquid crystal compound having a dielectric anisotropy smaller than −2 is preferably contained in the liquid crystal composition in an amount of 1 to 15 types, preferably 2 to 12 types, and more preferably 3 to 10 types. It is preferable to include 4 or more to 8 or less.

In addition, Δε of the compound is a value extrapolated from a measured value of dielectric anisotropy of a composition prepared by adding to a dielectrically neutral composition at 25 ° C. In addition, although content is described in% below, this means the mass%.

The liquid crystal compound having a dielectric anisotropy smaller than −2 according to the present invention preferably contains one or more compounds represented by the following general formula (II).

The liquid crystal composition according to the present invention has the general formula (II)

(In the general formula (II), R ^N1 and R ^N2 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms. or an alkenyloxy group having 2 to 10 carbon ^{atoms, R N1} and ^{R N2} being present in one -CH ₂ - or nonadjacent two or more -CH ₂ - are each independently -O -And / or S- may be substituted, and one or two or more hydrogen atoms present in these groups may be independently substituted with a fluorine atom or a chlorine atom,
C ^N1 and D ^N1 are each independently a trans-1,4-cyclohexylene group (one or non-adjacent two or more —CH ₂ — in the group is substituted by —O— or —S—). 1), 4-phenylene group (one or two or more non-adjacent —CH═ in the group may be substituted by —N═), 2-fluoro-1, 4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3 , 4-Tetrahydronaphthalene-2,6-di Yl group,
m ^N1 and m ^N2 each independently represent 0, 1, 2, or 3. Z ^N1 and ^{Z N2} are, each _{_{_{independently, -OCH 2 -, - CH 2}}} O -, - CF 2 O -, - OCF 2 -, - C 2 H 4 -, - CF 2 CF 2 - or a single bond Represents. When a plurality of C ^N1 , D ^N1 , Z ^N1 and / or Z ^N2 are present, they may be the same or different. It is preferable that it is 1 type, or 2 or more types chosen from the compound group represented by this.

In the general formula (II), R ^N1 and R ^N2 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or It preferably represents an alkenyloxy group having 2 to 5 carbon atoms.

In the general formula ^{(II), C N1} and ^{D N1} are, each independently, trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3- Fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [ 2.2.2] Octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2 , 6-diyl group is preferable, and trans-1,4-cyclohexylene group or 1,4-phenylene group is more preferable.

In the general formula (II), Z ^N1 and Z ^N2 are each independently —OCH ₂ —, —CH ₂ O—, —CF ₂ O—, —OCF ₂ —, —C ₂ H ₄ —, — CF ₂ CF ₂ — or a single bond is preferable, —OCH ₂ —, —CH ₂ O—, —C ₂ H ₄ — or a single bond is more preferable.

In the general formula (II), it is preferable that m ^N1 and m ^N2 each independently represent 0, 1 or 2. m ^N1 + m ^N2 is preferably 1, 2 or 3, more preferably 1 or 2.

The total content of the compound represented by the general formula (II) contained in the liquid crystal composition according to the present invention is preferably 1% by mass, preferably 3% by mass, preferably 5% by mass, as the lower limit. %, Preferably 10% by weight, preferably 12% by weight, preferably 15% by weight, preferably 17% by weight, preferably 20% by weight, preferably 22% by weight, preferably 25% by weight, and 27% by weight. Preferably, 30 mass% is preferable. As an upper limit, 70 mass% is preferable, 67 mass% is preferable, 65 mass% is preferable, 63 mass% is preferable, 60 mass% is preferable, 57 mass% is preferable, 55 mass% is preferable, and 53 mass% is 53 mass%. Preferably, 50% by weight is preferred, 45% by weight is preferred, 43% by weight is preferred, 40% by weight is preferred, 38% by weight is preferred, 36% by weight is preferred, 34% by weight is preferred, 30% by weight is preferred, 28% by mass is preferable, 26% by mass is preferable, 24% by mass is preferable, 22% by mass is preferable, 20% by mass is preferable, 18% by mass is preferable, 15% by mass is preferable, 13% by mass is preferable, and 10% by mass. % Is preferred.

The compound represented by general formula (II) according to the present invention is one or more selected from the group consisting of compounds represented by general formula (II-A1) to general formula (II-C4). Preferably there is.

(In the above general formula, R ^N3 and R ^N4 each independently represents an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and 1 present in R ^N3 and R ^N4. Or two or more hydrogen atoms may be each independently substituted with a fluorine atom or a chlorine atom.)
In the liquid crystal composition according to the present invention, among the compounds represented by the general formulas (II-A1) to (II-C4), the general formula (II-A1), the general formula (II-A3), the general formula Formula (II-B1), Formula (II-B2), Formula (II-B3), Formula (II-B4), Formula (II-B6), Formula (II-C1), Formula (II) II-C2) and general formula (II-C4) are preferred, and general formula (II-A1), general formula (II-A3), general formula (II-B1), general formula (II-B2), The general formula (II-B3), the general formula (II-B4), the general formula (II-B6), and the general formula (II-C4) are more preferable.

The compound represented by formula (II-A1) according to the present invention is preferably a compound selected from the group of compounds represented by formula (II-A1-1) to formula (II-A1-12) The compounds represented by formula (II-A1-4), formula (II-A1-5), formula (II-A1-10) and formula (II-A1-11) are preferred.

The compounds represented by formula (II-A1-1) to formula (II-A1-12) can be used alone or in combination.

The lower limit value of the compound represented by formula (II-A1) alone or the preferred content of these compounds with respect to the total amount of the composition of the present invention is 3%, 5%, 10% 13%, 15%, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by general formula (II-A2) is preferably a compound selected from the group of compounds represented by formula (II-A2-1) to formula (II-A2-12).

The compounds represented by the formulas (II-A2-1) to (II-A2-12) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit of the preferable content of the compound represented by general formula (II-A2) alone or these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by formula (II-A3) according to the present invention is preferably a compound selected from the group of compounds represented by formula (II-A3-1) to formula (II-A3-12). Formula (II-A3-2), Formula (II-A3-5), Formula (II-A3-8), Formula (II-A3-9), Formula (II-A3-10) and Formula (II- A compound represented by A3-11) is preferred.

The compounds represented by the formulas (II-A3-1) to (II-A3-12) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by the general formula (II-A3) alone or the preferred content of these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by general formula (II-A4) according to the present invention is preferably a compound selected from the group of compounds represented by formula (II-A4-1) to formula (II-A4-12) .

The compounds represented by the formulas (II-A4-1) to (II-A4-12) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by the general formula (II-A4) alone or the preferred content of these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by formula (II-A5) according to the present invention is preferably a compound selected from the group of compounds represented by formula (II-A5-1) to formula (II-A5-6) Further preferred are compounds represented by formula (II-A5-2) and formula (II-A5-5).

The compounds represented by the formulas (II-A5-1) to (II-A5-6) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by the general formula (II-A5) alone or the preferred content of these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by formula (II-B1) according to the present invention is one or more selected from the group consisting of formulas (II-B1-1) to (II-B1-8) And is preferably a compound represented by formulas (II-B1-1) to (II-B1-4), represented by formula (II-B1-1) and formula (II-B1-3). Are preferred.

The compounds represented by the formulas (II-B1-1) to (II-B1-8) can be used singly or in combination, but with respect to the total amount of the composition of the present invention. The lower limit value of the compound represented by the general formula (II-B1) alone or a preferable content of these compounds is 5%, 10%, 13%, 15%, 17% , 20%, 23%, 25%, 27%, 30%, 33%, and 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% %, 5%, 3%.

The compound represented by formula (II-B2) according to the present invention is one or more selected from the group consisting of formulas (II-B2-1) to (II-B2-8) Are preferred, and compounds represented by formulas (II-B2-1) to (II-B2-4) are preferred.

The compounds represented by the formulas (II-B2-1) to (II-B2-8) can be used alone or in combination, but with respect to the total amount of the composition of the present invention. The lower limit value of the compound represented by the general formula (II-B2) alone or a preferable content of these compounds is 3%, 5%, 7%, 10%, 13% 15%, 17%, and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 13%, 11%, 10%, and 8%.

The compound represented by formula (II-B3) according to the present invention is one or more selected from the group consisting of formulas (II-B3-1) to (II-B3-11) Are preferred, and compounds represented by formulas (II-B3-1) to (II-B2-7) are preferred.

The compounds represented by the formulas (II-B3-1) to (II-B3-11) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by the general formula (II-B3) alone or the preferred content of these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% %, 5%, and 4%.

The compound represented by formula (II-B4) according to the present invention is one or more selected from the group consisting of formulas (II-B4-1) to (II-B4-9) Are preferred, and compounds represented by formulas (II-B4-1) to (II-B4-7) are preferred.

The compounds represented by the formulas (II-B4-1) to (II-B4-9) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit of the preferred content of the compound represented by the general formula (II-B4) alone or these compounds is 3%, 5%, 7%, 10%, 13% Yes, 15%, 17%, 20%, 23%, 25%. The upper limit of the preferable content is 40%, 37%, 35%, 33%, 30%, 28%, and 25% with respect to the total amount of the composition of the present invention. %, 23%, 20%, 18%, 15%, 13%.

The compound represented by formula (II-B5) according to the present invention is one or more selected from the group consisting of formulas (II-B5-1) to (II-B5-12) Are preferred, and compounds represented by formulas (II-B5-1) to (II-B5-6) are preferred.

The compounds represented by the formulas (II-B5-1) to (II-B5-12) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by the general formula (II-B5) alone or the preferred content of these compounds is 2%, 10%, 13%, 15%, 17% Yes, 20%. The upper limit of the preferable content is 50%, 40%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the composition of the present invention. %, 15%, 10%, 8%, 5%, 3%.

The compound represented by the general formula (II-B6) is preferably one or more selected from the group consisting of formulas (II-B6-1) to (II-B6-6), Compounds represented by formulas (II-B6-1) to (II-B6-4) are preferred.

The compounds represented by formula (II-B6-1) and formula (II-B6-6) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of all the compounds represented by the general formula (II-B6) alone or the preferred content of these compounds is 5%, 8%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the composition of the present invention. %, 18%, 15% and 13%.

The compound represented by formula (II-C1) according to the present invention is preferably a compound selected from the group of compounds represented by formula (II-C1-1) to formula (II-C1-10) The compounds represented by formula (II-C1-5), formula (II-C1-6), formula (II-C1-7) and formula (II-C1-9) are preferred.

The compounds represented by the formulas (II-C1-1) to (II-C1-10) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by the general formula (II-C1) alone or the preferred content of these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by formula (II-C2) according to the present invention is preferably a compound selected from the group of compounds represented by formula (II-C2-1) to formula (II-C2-10) Compounds represented by formula (II-C2-2), formula (II-C2-5), formula (II-C2-6) and formula (II-C2-7) are preferred.

The compounds represented by the formulas (II-C2-1) to (II-C2-10) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit of the preferred content of the compound represented by the general formula (II-C2) alone or these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by general formula (II-C3) according to the present invention is preferably a compound selected from the group of compounds represented by formula (II-C3-1) to formula (II-C3-10). The compounds represented by formula (II-C3-2), formula (II-C3-5) and formula (II-C3-7) are preferred.

The compounds represented by formula (II-C3-1) to formula (II-C3-10) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by general formula (II-C3) alone or the preferred content of these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by formula (II-C4) according to the present invention is preferably a compound selected from the group of compounds represented by formula (II-C4-1) to formula (II-C4-12). Compounds represented by formula (II-C4-1), formula (II-C4-4), formula (II-C4-7) and formula (II-C4-10) are preferred.

The compounds represented by the formulas (II-C4-1) to (II-C4-12) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by the general formula (II-C4) alone or the preferable content of these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The liquid crystal composition according to the present invention preferably contains a liquid crystal compound having a dielectric anisotropy of −2 or more and 2 or less in addition to the compound represented by the general formula (I). The liquid crystal compound having a dielectric anisotropy of −2 or more and 2 or less is preferably contained in the liquid crystal composition in an amount of 1 to 15 types, preferably 2 to 12 types, and more preferably 3 to 10 types. It is preferable to include not more than 4 species, and it is preferable to include 4 to 8 species.

As the liquid crystal compound having a dielectric anisotropy of −2 or more and 2 or less according to the present invention, the following general formula (III):

(In the general formula (III), R ^NP1 and R ^NP2 each independently represents an alkyl group having 1 to 10 carbon atoms, and one or non-adjacent two or more —CH in the alkyl group. ₂ — each independently may be substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
m ^NP1 represents 0, 1, 2 or 3,
E ^NP1 , F ^NP1 and G ^NP1 are each independently a trans-1,4-cyclohexylene group (one or non-adjacent two or more —CH ₂ — in the group is represented by —O— or S—). May be substituted), 1,4-phenylene group (one or two or more non-adjacent —CH═ may be substituted by —N═), naphthalene-2, 6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2,3,4) -Tetrahydronaphthalene-2,6-diyl group represented by one —CH═ or two or more non-adjacent —CH═ may be replaced by —N═. The hydrogen atom contained in the group is a cyano group It may be substituted with a fluorine atom or a chlorine atom,
Z ^NP1 and Z ^NP2 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, — OCF ₂ —, —CF ₂ O—, —CH═NN—CH—, —CH═CH—, —CF═CF— or —C≡C—
When a plurality of F ^NP1 or Z ^NP2 are present, they may be the same or different. However, in general formula (III), the compounds represented by general formula (I) and general formula (II) are excluded. It is preferable that it is a compound chosen from the compound group represented by this.

In addition, the compound represented by the general formula (III) preferably has a dielectric anisotropy of −2 or more and 2 or less, and the number of halogens in the molecule of the general formula (III) is 1 or less. Is preferred.

When importance is attached to reliability, both R ^NP1 and R ^NP2 are preferably alkyl groups. When importance is attached to reducing the volatility of the compound, it is preferably an alkoxy group, and importance is placed on lowering viscosity. In this case, at least one is preferably an alkenyl group.

R ^NP1 and R ^NP2 are each a linear alkyl group having 1 to 5 carbon atoms or a linear carbon atom having 1 to 4 carbon atoms when the ring structure to which they are bonded is a phenyl group (aromatic). When the ring structure to which it is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a straight-chain C 1-5 carbon atom is preferred. Alkyl groups, linear alkoxy groups having 1 to 4 carbon atoms and linear alkenyl groups having 2 to 5 carbon atoms are preferred. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

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

E ^NP1 , F ^NP1, and G ^NP1 are preferably aromatic when it is required to increase Δn, and are preferably aliphatic for improving the response speed, and are independently trans- 1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 -Diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, preferably a trans-1,4-cyclohexylene group or 1,4-phenylene group Succoth is more preferable.

Z ^NP1 and Z ^NP2 are preferably single bonds when the response speed is important.

When considering the response speed, m ^NP1 is preferably 0, 2 or 3 is preferable for improving the upper limit temperature of the nematic phase, and 1 is preferable for balancing these. In order to satisfy the properties required for the composition, it is preferable to combine compounds having different values.

The total content of the compound represented by the general formula (III) contained in the liquid crystal composition according to the present invention is preferably 1% by mass, preferably 3% by mass, preferably 5% by mass as the lower limit. %, Preferably 10% by weight, preferably 12% by weight, preferably 15% by weight, preferably 17% by weight, preferably 20% by weight, preferably 22% by weight, preferably 25% by weight, and 27% by weight. Preferably, 30 mass% is preferable. As an upper limit, 70 mass% is preferable, 67 mass% is preferable, 65 mass% is preferable, 63 mass% is preferable, 60 mass% is preferable, 57 mass% is preferable, 55 mass% is preferable, and 53 mass% is 53 mass%. Preferably, 50% by weight is preferred, 45% by weight is preferred, 43% by weight is preferred, 40% by weight is preferred, 38% by weight is preferred, 36% by weight is preferred, 34% by weight is preferred, 30% by weight is preferred, 28% by mass is preferable, 26% by mass is preferable, 24% by mass is preferable, 22% by mass is preferable, 20% by mass is preferable, 18% by mass is preferable, 15% by mass is preferable, 13% by mass is preferable, and 10% by mass. % Is preferred.

The compound represented by general formula (III) according to the present invention is one or more selected from the group consisting of compounds represented by general formula (III-A) to general formula (III-J). Preferably there is.

(In the formula, R ^NP1 and R ^NP2 are the same as those in the general formula (III), and X ^np1 and X ^np2 are each independently a hydrogen atom or a fluorine atom.)
In the general formula (III-A), R ^NP1 and R ^NP2 are a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear carbon. An alkenyl group having 2 to 5 atoms is preferred.

The compound represented by the general formula (III-A) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they can be used in appropriate combinations depending on the required properties such as low-temperature solubility (low-temperature storage stability), transition temperature, electrical reliability, and birefringence. To do. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

The lower limit of the preferable content of the general formula (III-A) in the liquid crystal composition according to the present invention is 1%, 2%, 3%, and 5% with respect to the total amount of the liquid crystal composition. %, 7%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50% % And 55%. The upper limit of the preferable content is 95%, 90%, 85%, 80%, 75%, 70%, 65%, based on the total amount of the composition of the present invention. %, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%.

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

The compound represented by the general formula (III-A) is preferably one or more compounds selected from the group of compounds represented by the general formulas (III-A1) to (III-A5). .

(Wherein R ^NP2 represents the same meaning as in general formula (III-A).)
(Wherein R ^NP3 and R ^NP4 each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
(In the formula, each R ^NP5 independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
The lower limit of the preferable content of the compound represented by the formula (III-A1) with respect to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% 15%, 17%, 20%, 23%, and 25%. The upper limit of the preferable content is 55%, 53%, 50%, 45%, 40%, 37%, and 35% with respect to the total amount of the composition of the present invention. %, 33%, 30%, 27%, 25%, 23%, 23%, 20%, 17%, 15%, 13%, 10% %, 8% and 7%.

The compound represented by general formula (III-A1) according to the present invention is preferably a compound selected from the group of compounds represented by formula (III-A1-1) to formula (III-A1-3). A compound represented by formula (III-A1-2) or (III-A1-3) is preferable, and a compound represented by formula (III-A1-3) is particularly preferable.

The lower limit of the preferable content of the compound represented by the formula (III-A1-3) with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7% and 10%. The upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7%, and 6% with respect to the total amount of the composition of the present invention. %, 5%, 3%.

The lower limit of the preferable content of the compound represented by the formula (III-A1-2) with respect to the total amount of the composition of the present invention is 1%, 5%, 10%, 15% 17%, 20%, 23%, 25%, 27%, 30%, 35%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 42%, 40%, and 38% with respect to the total amount of the composition of the present invention. %, 35%, 33%, and 30%.

The lower limit of the preferable content of the compound represented by the formula (III-A2) with respect to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% 15%, 17%, 20%, 23%, 25%, 30%. The upper limit of the preferable content is 65%, 63%, 60%, 57%, 55%, 53%, 53%, and 50% with respect to the total amount of the composition of the present invention. %, 45%, 40%, 37%, 35%, 33%, 30%, 27%, 25%, 23%, 20% %, 17%, 15%, 13%, and 10%.

The compound represented by general formula (III-A2) according to the present invention is preferably a compound selected from the group of compounds represented by formula (III-A2-1) to formula (III-A2-4) A compound represented by formula (III-A2-2) to formula (III-A2-4) is preferable. In particular, the compound represented by the formula (III-A2-2) is preferable because the response speed of the composition of the present invention is particularly improved. When obtaining Tni higher than the response speed, it is preferable to use a compound represented by formula (III-A2-3) or formula (III-A2-4). The content of the compounds represented by the formulas (III-A2-3) and (III-A2-4) is preferably not more than 30% in order to improve the solubility at low temperatures.

The lower limit of the preferable content of the compound represented by the formula (III-A2-2) with respect to the total amount of the composition of the present invention is 10%, 15%, 18%, 20% 23%, 25%, 27%, 30%, 33%, 35%, 38%, 40%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 43%, 40%, and 38% with respect to the total amount of the composition of the present invention. %, 35%, 32%, 30%, 27%, 25%, and 22%.

The lower limit of the total preferable content of the compound represented by the formula (III-A2-3) and the compound represented by the formula (III-A2-2) with respect to the total amount of the composition of the present invention is 10 %, 15%, 20%, 25%, 27%, 30%, 35%, and 40%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 43%, 40%, and 38% with respect to the total amount of the composition of the present invention. %, 35%, 32%, 30%, 27%, 25%, and 22%.

The lower limit of the preferable content of the compound represented by the formula (III-A3) with respect to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% 15%, 17%, 20%, 23%, 25%, 30%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 40%, 37%, and 35% with respect to the total amount of the composition of the present invention. %, 33%, 30%, 27%, 25%, 23%, 23%, 20%, 17%, 15%, 13%, 10% %.

Further, the compound represented by the general formula (III-A3) is preferably a compound selected from the group of compounds represented by the formula (III-A3-1) to the formula (III-A3-6) A compound represented by formula (III-A3-1), formula (III-A3-3) or formula (III-A3-4) is preferred. In particular, the compound represented by the formula (III-A3-1) is preferable because the response speed of the composition of the present invention is particularly improved. Further, when obtaining Tni higher than the response speed, it is represented by the formula (III-A3-3), formula (III-A3-4), formula (III-A3-5) and formula (III-A3-6). It is preferable to use the compound. The total content of the compounds represented by formula (III-A3-3), formula (III-A3-4), formula (III-A3-5) and formula (III-A3-6) is In order to improve the solubility, it is not preferable to make it 20% or more.

The lower limit of the preferable content of the compound represented by the formula (III-A3-1) with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7%, 10%, 13%, 15%, 18%, 20%. The upper limit of the preferable content is 20%, 17%, 15%, 13%, 10%, 8%, and 7% with respect to the total amount of the composition of the present invention. % And 6%.

The lower limit of the preferable content of the compound represented by the formula (III-A4) with respect to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% 15%, 17%, and 20%. The upper limit of the preferable content is 25%, 23%, 20%, 17%, 15%, 13%, and 10% with respect to the total amount of the composition of the present invention. %.

The lower limit of the preferable content of the compound represented by the formula (III-A5) with respect to the total amount of the composition of the present invention is 1%, 5%, 10%, 13% 15%, 17%, and 20%. The upper limit of the preferable content is 25%, 23%, 20%, 17%, 15%, 13%, and 10% with respect to the total amount of the composition of the present invention. %.

Further, the compounds represented by the general formulas (III-A4) and (III-A5) are compounds selected from the group of compounds represented by the formulas (III-A4-1) to (III-A5-3) Preferably, it is a compound represented by formula (III-A4-2) or formula (III-A5-2).

The lower limit of the preferable content of the compound represented by the formula (III-A4-2) with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% 7%, 10%, 13%, 15%, 18%, 20%. The upper limit of the preferable content is 20%, 17%, 15%, 13%, 10%, 8%, and 7% with respect to the total amount of the composition of the present invention. % And 6%.

Formula (III-A1-3), Formula (III-A2-2), Formula (III-A3-1), Formula (III-A3-3), Formula (III-A3-4), Formula (III-A3) −5) and two or more compounds selected from the compounds represented by formula (III-A3-6) are preferably combined, and are represented by formula (III-A1-3), formula (III-A2-2), formula Combining two or more compounds selected from the compounds represented by (III-A3-1), formula (III-A3-3), formula (III-A3-4) and formula (III-A4-2) The lower limit of the preferred content of the total content of these compounds is 1%, 2%, 3%, 5% with respect to the total amount of the composition of the present invention, 7%, 10%, 13%, 15%, 18%, 20 23% 25% 27% 30% 33% 35% The upper limit is 80% of the total amount of the composition of the present invention. 70%, 60%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 28% 25%, 23%, 20%. When emphasizing the reliability of the composition, two or more selected from compounds represented by formula (III-A3-1), formula (III-A3-3) and formula (III-A3-4)) It is preferable to combine these compounds, and when importance is attached to the response speed of the composition, two or more compounds selected from the compounds represented by formula (III-A1-3) and formula (III-A2-2) Are preferably combined.

The compound represented by formula (III-B) according to the present invention is preferably a compound selected from the group of compounds represented by formula (III-B-1) to formula (III-B-8). .

The compounds represented by the formulas (III-B-1) to (III-B-8) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit value of the compound represented by general formula (III-B) alone or the preferred content of these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by general formula (III-C) according to the present invention is preferably a compound selected from the group of compounds represented by formula (III-C-1) to formula (III-C-8). Compounds represented by formula (III-C-1), formula (III-C-2) and formula (III-C-3) are preferred.

The compounds represented by the formulas (III-C-1) to (III-C-8) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit of the preferred content of the compound represented by general formula (III-C) alone or these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by general formula (III-D) according to the present invention is preferably a compound selected from the group of compounds represented by formula (III-D-1) to formula (III-D-6). The compounds represented by formula (III-D-1), formula (III-D-3), formula (III-D-4) and formula (III-D-6) are preferred.

The lower limit value of the compound represented by formula (III-D) alone or the preferred content of these compounds with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%, and 10%. The upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7%, and 6% with respect to the total amount of the composition of the present invention. %, 5%, 3%.

The compound represented by general formula (III-E) according to the present invention is preferably a compound selected from the group of compounds represented by formula (III-E-1) to formula (III-E-8). .

The compounds represented by the formulas (III-E-1) to (III-E-8) can be used alone or in combination, but the total amount of the composition of the present invention is not limited. The lower limit of the preferred content of the compound represented by the general formula (III-E) alone or these compounds is 3%, 5%, 10%, 13%, 15% Yes, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

The compound represented by general formula (III-F) according to the present invention is preferably a compound selected from the group of compounds represented by formula (III-F-1) to formula (III-F-6). A compound represented by formula (III-F-1) or formula (III-F-2) is preferable.

When a high birefringence is obtained, the effect is high when the content is set to be large. On the other hand, when high Tni is emphasized, the effect is high when the content is set low. Furthermore, when improving dripping marks and image sticking characteristics, it is preferable to set the content range in the middle.

The lower limit value of the compound represented by the formula (III-F) alone or the preferred content of these compounds with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%, and 10%. The upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7%, and 6% with respect to the total amount of the composition of the present invention. %, 5%, 3%.

The compound represented by the general formula (III-G) according to the present invention is preferably, for example, a compound represented by the formula (III-G-1) to the formula (III-G-3).

Contains a compound represented by the formula (III-G-1) according to required performance such as solubility at low temperature (low temperature storage stability), transition temperature, electrical reliability, birefringence and the like. Even if it contains a compound represented by the formula (III-G-2), a compound represented by the formula (III-G-1) and a compound represented by the formula (III-G-2) And all of the compounds represented by formulas (III-G-1) to (III-G-3) may be contained. The lower limit of the preferable content of the compound represented by the formula (III-G-1) or the formula (III-G-2) with respect to the total amount of the composition of the present invention is 3%, Yes, 7%, 9%, 11%, 12%, 13%, 18%, 21%, and the preferred upper limit is 45, 40% , 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8% .

When both the compound represented by the formula (III-G-1) and the compound represented by the formula (III-G-2) are contained, both compounds with respect to the total amount of the composition of the present invention The lower limit of the preferred content is 15%, 19%, 24%, and 30%, and the preferred upper limit is 45, 40%, 35%, and 30%. Yes, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (III-G) according to the present invention is preferably a compound represented by the formula (III-G-4) to (III-G-6), for example. A compound represented by -G-4) is preferred.

Contains a compound represented by the formula (III-G-4) according to required performance such as solubility at low temperature (low temperature storage stability), transition temperature, electrical reliability, birefringence and the like. Even if it contains a compound represented by the formula (III-G-5), a compound represented by the formula (III-G-4) and a compound represented by the formula (III-G-5) And may contain both.

The lower limit of the preferable content of the compound represented by the formula (III-G-4) or the formula (III-G-5) with respect to the total amount of the composition of the present invention is 3%, Yes, 7%, 9%, 11%, 12%, 13%, 18%, 21%. Preferred upper limit values are 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13% %, 10%, and 8%.

When both the compound represented by the formula (III-G-4) and the compound represented by the formula (III-G-5) are contained, both compounds relative to the total amount of the composition of the present invention The lower limit of the preferred content is 15%, 19%, 24%, and 30%, and the preferred upper limit is 45, 40%, 35%, and 30%. Yes, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (III-G) according to the present invention is preferably a compound represented by the formula (III-G-7) to the formula (III-G-10).

The lower limit value of the compound represented by formula (III-G) alone or the preferred content of these compounds with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%. The upper limit of the preferable content of the compound represented by the formula (III-G) with respect to the total amount of the composition of the present invention is 50%, 40%, 35%, 30%. 20%, 15%, 10%, 5%.

The compound represented by the general formula (III-H) according to the present invention is preferably a compound represented by the formula (III-H-1) or the formula (III-H-7). A compound represented by III-H-1) is preferred.

The lower limit value of the compound represented by formula (III-H) alone or the preferred content of these compounds with respect to the total amount of the composition of the present invention is 1%, 2%, 3% 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35% 40%. The upper limit of the preferable content of the compound represented by the formula (III-H) with respect to the total amount of the composition of the present invention is 50%, 40%, 35%, and 30%. 20%, 15%, 10%, 5%.

The compound represented by formula (III-I) according to the present invention is preferably a compound represented by formula (III-I-1) to formula (III-I-9).

There are no particular restrictions on the types of compounds that can be combined, but 1 to 3 types of these compounds are preferably contained, more preferably 1 to 4 types. Further, since the wide molecular weight distribution of the selected compound is also effective for compatibility (also referred to as solubility), for example, from the compound represented by the formula (III-I-1) or (III-I-2) From the compound represented by the type, formula (III-I-4) or (III-I-5), one from the compound represented by formula (III-I-6) or (III-I-7) It is preferable to select one compound from one compound represented by the formula (III-I-8) or (III-I-9) and combine them as appropriate. Among them, represented by formula (III-I-1), formula (III-I-3), formula (III-I-4), formula (III-I-6) and formula (III-I-9) It is preferable to include a compound.

Further, the compound represented by the general formula (III-I) is preferably, for example, a compound represented by the formula (III-I-10) to the formula (III-I-17). A compound represented by III-I-11) is preferred.

The lower limit value of the compound represented by formula (III-I) alone or the preferred content of these compounds with respect to the total amount of the composition of the present invention is 1%, 2%, 3% 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35% 40%. The upper limit of the preferable content of the compound represented by the general formula (III-I) with respect to the total amount of the composition of the present invention is 50%, 40%, 35%, 30% Yes, 20%, 15%, 10%, 5%. When emphasizing to increase Δn, it is preferable to increase the content, and when emphasizing the precipitation at low temperature, it is preferable to decrease the content.

Of the compounds represented by general formula (I), general formula (II), general formula (III), general formula (RM-1) and general formula (RM-2) with respect to the total amount of the composition of the present invention. The lower limit of the total preferable content is 80%, 85%, 88%, 90%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 100%. The upper limit of the preferable content is 100%, 99%, 98%, and 95%.

The lower limit of the preferable total content of the compounds represented by formula (I), formula (II-A1) and formula (II-A3) relative to the total amount of the composition of the present invention is 15% 17%, 20%, 23%, 25%, 28%, 30%, 32%, 35%. The upper limit of the preferable content is 90%, 80%, 70%, 65%, 60%, 55%, 52%, 50%, 47% 45%, 42%, 40%, 37%, 35%.

Preferred total content of compounds represented by general formula (I), general formula (II-A1), general formula (II-A3) and general formula (II-B4) with respect to the total amount of the composition of the present invention The lower limit of the amount is 15%, 17%, 20%, 23%, 25%, 28%, 30%, 32%, 35% 37% and 40%. The upper limit of the preferable content is 92%, 80%, 70%, 65%, 63%, 60%, 57%, 55%, 53% , 50%, 47%, 45%, 43%, 42%, 40%, 38%, 37%.

General formula (I), general formula (II-A1), general formula (II-A3), general formula (II-B4), general formula (III-A), general formula with respect to the total amount of the composition of the present invention The preferred total content of the compounds represented by formula (III-D), general formula (III-F), general formula (III-G), general formula (III-H) and general formula (III-I) The lower limits are 65%, 67%, 70, 72%, 75%, 78%, 80%, 82%, 85%, 87% 90%. The upper limit of the preferable content is 100%, 98%, 95%, 93%, 90%, 87%, 85%, 83%, 80% 78%, 75%, 73%, 70%, 68%.

In the liquid crystal composition according to the present invention, Δε at 25 ° C. is preferably −2.0 to −6.0, more preferably −2.5 to −5.0, and −2.5 to −3. 5 is particularly preferred.

In the liquid crystal composition according to the present invention, Δn at 25 ° C. is preferably 0.08 to 0.13, more preferably 0.09 to 0.13, and particularly preferably 0.10 to 0.12. More specifically, it is preferably 0.10 to 0.13 when dealing with a thin cell gap, and preferably 0.08 to 0.10 when dealing with a thick cell gap.

The liquid crystal composition according to the present invention has an η at 20 ° C. of 10 to 30 mPa · s, more preferably 10 to 25 mPa · s, and particularly preferably 10 to 20 mPa · s.

The liquid crystal composition according to the present invention has a rotational viscosity (γ1) at 25 ° C. of 20 to 250 mPa · s, preferably 25 to 200 mPa · s, and preferably 30 to 160 mPa · s, 30 To 140 mPa · s, preferably 40 to 140 mPa · s, preferably 40 to 130 mPa · s, preferably 40 to 125 mPa · s, and 40 to 120 mPa · s. More preferably, the pressure is 40 to 115 mPa · s, still more preferably 40 to 110 mPa · s, and particularly preferably 40 to 100 mPa · s.

The liquid crystal composition according to the present invention has a Tni of 60 ° C. to 120 ° C., more preferably 70 ° C. to 100 ° C., and particularly preferably 70 ° C. to 85 ° C.

The composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms such as a peracid (—CO—OO—) structure are bonded in the molecule.

When emphasizing the reliability and long-term stability of the composition, the content of the compound having a carbonyl group is preferably 5% or less, more preferably 3% or less with respect to the total mass of the composition. Preferably, it is more preferably 1% or less, and most preferably not substantially contained.

When importance is attached to the stability by UV irradiation, the content of the compound substituted with chlorine atoms is preferably 15% or less, preferably 10% or less, based on the total mass of the composition. % Or less, preferably 5% or less, more preferably 3% or less, and still more preferably substantially not contained.

It is preferable to increase the content of the compound in which the ring structure in the molecule is a monocyclic 6-membered ring other than the general formula (I) from the balance of the entire physical properties of the liquid crystal composition, and the ring structure in the molecule has the general formula The content of the compound which is a monocyclic 6-membered ring except for (I) is preferably 80% or more, more preferably 90% or more, more preferably 95% or more with respect to the total mass of the composition. More preferably, it is most preferable that the composition is composed only of compounds in which the ring structure in the molecule is a monocyclic 6-membered ring except for the general formula (I).

In order to suppress deterioration due to oxidation of the composition, it is preferable to reduce the content of the compound having a cyclohexenylene group as a ring structure, and the content of the compound having a cyclohexenylene group as the total mass of the composition. On the other hand, it is preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and still more preferably not contained.

When importance is attached to improvement of viscosity and improvement of Tni, the 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, may be reduced. Preferably, the content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is preferably 10% or less, more preferably 8% or less, based on the total mass of the composition. It is more preferably 5% or less, more preferably 3% or less, and still more preferably substantially not containing other than the general formula (I).

“Substantially not contained” in the present application means that it is not contained except for an unintentionally contained product.

The second aspect of the present invention is a liquid crystal display device provided with a liquid crystal composition containing a compound represented by the general formula (I). The liquid crystal display device using the liquid crystal composition containing the compound of the present invention is useful for achieving both high-speed response and suppression of display failure, and is particularly useful for a liquid crystal display device for active matrix driving. It can be applied to liquid crystal display elements for mode, PSVA mode, PSA mode, IPS mode, FFS mode or ECB mode.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. Further, “%” in the compositions of the following Examples and Comparative Examples means “% by mass”.

The following abbreviations are used for the description of compounds in the examples.
(Side chain)
-N -C _n H _{2n + 1} linear alkyl group having n carbon atoms n- C _n H _{2n + 1-} linear alkyl group having n carbon atoms -On -OC _n H _{2n + 1} linear alkoxyl having n carbon atoms Group nO— C _n H _{2n + 1} O— Linear alkoxyl group having n carbon atoms —nO— —C _n H _2n O—
-V -CH = CH ₂
V- CH ₂ = CH-
-V1 -CH = CH-CH ₃
1V- CH ₃ —CH═CH—
(Ring structure)

In the examples, the measured characteristics are as follows.

T _ni : Nematic phase-isotropic liquid phase transition temperature (° C.)
Δn: refractive index anisotropy at 25 ° C. η: viscosity at 20 ° C. (mPa · s)
γ1: rotational viscosity at 25 ° C. (mPa · s)
Δε: dielectric anisotropy at 25 ° C. K33: elastic constant K ₃₃ (pN) at 25 ° C.
Residual amount of polymerizable compound: A test panel into which a polymerizable liquid crystal composition was injected was irradiated with UV at 24 J or 48 J while applying a rectangular wave of 5 V at a frequency of 100 Hz. Then, it is the residual amount [ppm] of the polymerizable compound when the solution obtained by peeling the substrate of the panel and extracting the liquid crystal composition adhering to the surface with acetonitrile is measured by HPLC.

Pretilt angle: Pretilt angle measured by crystal rotation method using TBA-105 manufactured by Autronic after irradiating UV with 24J while applying a rectangular wave of 5V at a frequency of 100 Hz to a test panel into which a polymerizable liquid crystal composition was injected. [°].

Compatibility: The liquid crystal composition was placed in a 0.5 g vial, and after 240 hours, the presence or absence of precipitation was visually observed. If the precipitation was confirmed, it was rated as x. The storage temperature was 25 ° C, -25 ° C or -30 ° C.

<Production and evaluation of liquid crystal composition>
(Comparative Example 1, Comparative Example 2, Example 1, Example 2, Example 3 and Example 4)
LC-R1 (Comparative Example 1), LC-R2 (Comparative Example 2), LC-001 (Example 1), LC-002 (Example 2), LC-003 (Example 3) and LC-004 (implemented) The liquid crystal composition of Example 4) was prepared, its physical properties were measured, and compatibility was confirmed. Table 1 shows the composition of the liquid crystal composition, its physical properties and compatibility results.

(Table 1)

As a result of the compatibility test at 25 ° C., LC-001, LC-002, LC-003, and LC-004 were able to retain the nematic liquid crystal phase without any particular problem, but LC-R1 was precipitated immediately after dissolution. As a result, physical properties could not be measured. Since precipitation was confirmed even after depositing the deposited LC-R1 at 25 ° C. for 240 hours, it was determined as x. In addition, LC-R2, which has a reduced content of naphthalene compound in which the aromatic ring is not substituted with a fluorine atom, was also observed immediately after dissolution, as in LC-R1, and physical properties could not be measured. In addition, since LC-R2 was confirmed to precipitate even after being stored at 25 ° C. for 240 hours, it was determined as x. From this, it was confirmed that using a naphthalene compound in which the hydrogen atom of the aromatic ring is not substituted with a substituent is not preferable from the viewpoint of compatibility.

From the above, it was confirmed that LC-001, LC-002, LC-003, and LC-004, which are liquid crystal compositions of the present invention, show high compatibility. Thereby, it was confirmed that the liquid crystal composition of the present invention has solved the solubility (or compatibility) which is a problem of the prior art.

(Example 5, Example 6 and Example 7)
LC-005 (Example 5), LC-006 (Example 6), and LC-007 (Example 7) liquid crystal compositions were prepared, and low-temperature storage stability, which is one index of compatibility, was confirmed. The results are shown in Table 2.

(Table 2)

In the compatibility test at -25 ° C. (so-called low-temperature storage stability test), LC-005, LC-006 and LC-007 were not particularly problematic and could hold the nematic liquid crystal phase even after 240 hours.

In compatibility at -30 ° C (so-called low-temperature storage stability), LC-005 was able to retain the liquid crystal phase even after 240 hours, but LC-006 and LC-007 were confirmed to precipitate after 240 hours. It was done.

As shown in Comparative Examples 1 and 2 in Table 1, the liquid crystal composition containing 2-Ph-Ph-Np-3 is considered to be precipitated even at a low temperature because it was precipitated at room temperature (25 ° C.).

From the above, it was confirmed that LC-005, LC-006 and LC-007, which are the liquid crystal compositions of the present invention, have high compatibility, particularly excellent low-temperature storage stability. Thereby, it was confirmed that the liquid crystal composition of the present invention solves the problems of compatibility (or compatibility) and low-temperature storage stability, which are problems of the prior art.

In addition, when the experimental results of Examples 1 to 7 are seen, the liquid crystal composition of the present application is excellent in the compatibility between the liquid crystal compounds constituting the liquid crystal composition because the result of excellent compatibility is obtained. That is confirmed.

Next, a liquid crystal composition containing a liquid crystal monomer in the liquid crystal composition will be described.
<Preparation and Evaluation of Polymerizable Compound-Containing Liquid Crystal Composition>
(Comparative Example 3 and Example 8)
Polymerizable compound-containing liquid crystal compositions of LC-R3 (Comparative Example 3) and LC-A (Example 8) were prepared, and their physical properties were measured. Table 3 shows the composition of the polymerizable compound-containing liquid crystal composition and the results of its physical property values.

(Table 3)

LC-R3 and LC-A were each injected into a cell with ITO coated with a polyimide alignment film that induces homeotropic alignment with a cell gap of 3.5 μm by a vacuum injection method, while applying a rectangular wave of 5 V at a frequency of 100 Hz, Adjust the irradiation intensity of the cell surface to 100 mW / cm ² with a high-pressure mercury lamp through a filter that cuts out ultraviolet rays of 320 nm or less, and then irradiate with UV to polymerize the polymerizable compound in the polymerizable compound-containing liquid crystal composition. A vertically aligned liquid crystal display element was obtained. This liquid crystal display element (PSVA mode) showed high contrast and was confirmed to have a sufficiently fast response.

When UV was irradiated for 24 [J], LC-R3 had a residual amount of polymerizable compound of 1454 [ppm], whereas LC-A was 410 [ppm].

When UV was irradiated for 48 [J], LC-R3 had a residual polymerizable compound content of 1359 [ppm], whereas LC-A was 0 [ppm].

The remaining amount of the polymerizable compound in LC-A which is the polymerizable compound-containing liquid crystal composition of the present invention is sufficiently smaller than that of LC-R3 which is Comparative Example 3, and is sufficiently polymerized by less UV irradiation. Was confirmed to advance.

In addition, LC-A, which is a polymerizable compound-containing liquid crystal composition of the present invention, and LC-R3, which is Comparative Example 3, each have a pretilt angle of 85 [°] when irradiated with UV, so that alignment control is sufficiently performed. Is confirmed to be possible. The pretilt angle was measured at 25 ° C., and TBA105 manufactured by AUTRONIC-MELCHERS was used.

From the above, the liquid crystal composition of the present invention sufficiently suppresses the remaining of the polymerizable compound, so that display unevenness and image sticking are extremely suppressed, and the pretilt angle that affects display performance such as high-speed response and high contrast is obtained. It was confirmed that control was possible.

When the polymerizable compound of the formula (XX-5) used for LC-A was replaced with the polymerizable compound of the formula (XX-2), the same evaluation as in Example 8 was performed, and the problem of the present invention was solved. It was confirmed that

When the polymerizable compound of the formula (XX-5) used for LC-A was replaced with the polymerizable compound of the formula (M20) and evaluated in the same manner as in Example 8, the problem of the present invention was solved. It was confirmed that

When the polymerizable compound of the formula (XX-5) used in LC-A was replaced with the polymerizable compound of the formula (RM-2-1), the same evaluation as in Example 8 was performed. It was confirmed that the problem was solved.

The same evaluation as in Example 8 was performed by replacing 0.05% of the polymerizable compound of the formula (XX-5) used in LC-A with the polymerizable compound of the formula (XX-7). It was confirmed that the problems of the present invention were solved.

Of the polymerizable compounds of the formula (XX-5) used for LC-A, 0.02% was substituted with the polymerizable compound of the formula (M65), and the same evaluation as in Example 8 was performed. It was confirmed that the problem was solved.

(Comparative Example 4 and Example 9)
Polymerizable compound-containing liquid crystal compositions of LC-R4 (Comparative Example 4) and LC-B (Example 9) were prepared and their physical properties were measured. The constitution of the polymerizable compound-containing liquid crystal composition and the results of its physical property values are shown in Table 4.

(Table 4)

LC-R4 and LC-B were each injected by vacuum injection into a cell with ITO coated with a polyimide alignment film that induces homeotropic alignment with a cell gap of 3.5 μm, and a rectangular wave of 20 V was applied at a frequency of 100 Hz, Adjust the irradiation intensity of the cell surface to 100 mW / cm ² with a high-pressure mercury lamp through a filter that cuts out ultraviolet rays of 320 nm or less, and then irradiate with UV to polymerize the polymerizable compound in the polymerizable compound-containing liquid crystal composition. A vertically aligned liquid crystal display element was obtained. This liquid crystal display element (PSVA mode) was confirmed to exhibit a high contrast and a sufficiently high-speed response because the pretilt angle was sufficiently controlled in orientation.

When UV was irradiated for 24 [J], the residual amount of the polymerizable compound in LC-R4 was 1916 [ppm], whereas that in LC-B was 426 [ppm].

When UV was irradiated for 48 [J], LC-R4 had a residual polymerizable compound content of 1208 [ppm], whereas LC-B was 0 [ppm].

The remaining amount of the polymerizable compound in LC-B, which is the polymerizable compound-containing liquid crystal composition of the present invention, is sufficiently smaller than that of LC-R4 which is Comparative Example 4, and is sufficiently polymerized by less UV irradiation. Was confirmed to advance. As described above, it was confirmed that the remaining of the polymerizable compound was sufficiently suppressed and display unevenness and image sticking were extremely suppressed.

In addition, LC-B, which is a polymerizable compound-containing liquid crystal composition of the present invention, and LC-R4, which is Comparative Example 4, each have a pretilt angle of 86 [°] when irradiated with UV, so that alignment control is sufficient. Is confirmed to be possible. The pretilt angle was measured at 25 ° C., and TBA105 manufactured by AUTRONIC-MELCHERS was used.

(Example 10, Example 11 and Example 12)
LC-012, LC-013 and LC-014 liquid crystal compositions were prepared and their physical properties were measured. The composition of the liquid crystal composition and its physical property values are shown in Table 5.

(Table 5)

A polymerizable compound-containing liquid crystal composition obtained by adding 0.4 parts by weight of the compound represented by the formula (XX-5) to 99.6 parts by weight of the liquid crystal composition LC-012 was determined as Example 10.

A polymerizable compound-containing liquid crystal composition obtained by adding 0.4 part by weight of the compound represented by the formula (XX-5) to 99.6 parts by weight of the liquid crystal composition LC-013 was determined as Example 11.

A polymerizable compound-containing liquid crystal composition obtained by adding 0.4 part by weight of the compound represented by the formula (XX-5) to 99.6 parts by weight of the liquid crystal composition LC-014 was defined as Example 12.

As for Example 10, Example 11 and Example 12 as well as Example 8 and Example 9, when PSVA type liquid crystal display elements were used, it was confirmed that they showed high contrast and sufficiently fast response. . Moreover, the residual amount of the polymerizable compound after UV irradiation was sufficiently small, and it was confirmed that the polymerization proceeded sufficiently with a small amount of UV irradiation.

From the results of Examples 8 to 12, it can be confirmed that the liquid crystal composition according to the present invention is a liquid crystal composition that easily accepts the monomer and does not inhibit the reactivity of the monomer or has the effect of improving the reactivity of the monomer. .

Claims

Formula (I)

(In the general formula (I), R I1 and R I2 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms. or an alkenyloxy group having 2 to 10 carbon atoms, R I1 and R I2 in present in one -CH 2 - or nonadjacent two or more -CH 2 - are each independently -O -And / or S- may be substituted, and one or more hydrogen atoms present in these groups may each independently be substituted by a fluorine atom,
L I1 and L I2 each independently represent a hydrogen atom, a methyl group, a —CF 3 group, a fluorine atom or a chlorine atom,
A I1 and B I1 are each independently a trans-1,4-cyclohexylene group (one or non-adjacent two or more —CH 2 — in the group is substituted by —O— or S—). 1,4-phenylene group (one or two or more non-adjacent —CH═ in the group may be substituted by —N═), 1,4-cyclohexenylene 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, or 1,2, Represents a 3,4-tetrahydronaphthalene-2,6-diyl group, and the hydrogen atom of A I1 or B I1 may be substituted with a methyl group, a —CF 3 group, a fluorine atom or a chlorine atom;
One or more selected from the group consisting of A I1 , B I1 and L I1 and L I2 have a substituent other than a hydrogen atom, and the substituent is a methyl group , —CF 3 group, one or more selected from the group consisting of fluorine atom and chlorine atom, and each ring has 1 or less substituent,
m I1 represents 0, 1 or 2, and n I1 represents 0, 1 or 2. However, when there are a plurality of A I1 s , they may be different or the same. However, when there are a plurality of BI1s , they may be different or the same. A liquid crystal composition containing one or more compounds selected from the group of compounds represented by:
The general formula (I) is changed from the general formula (I-1) to the general formula (I-9).

(In the general formulas (I-1) to (I-9), R I1 and R I2 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, or a carbon atom. Represents an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 2 to 10 carbon atoms, and one or two or more hydrogen atoms present in these groups may be substituted by fluorine atoms. The liquid crystal composition according to claim 1, wherein the liquid crystal composition is one or more compounds selected from the group consisting of:
Formulas (RM-1) and (RM-2)

“In the general formula (RM-1), Z M1 and Z M2 are represented by the following:

(In the formula (Z M1 ), X M11 to X M15 are each independently one or more selected from the group consisting of a methyl group, a —CF 3 group, a fluorine atom and a chlorine atom, or a formula (RM -S11), but at least one of X M11 to X M15 represents the formula (RM-S11).)

(In the formula (Z M2 ), X M21 to X M25 are each independently one or more selected from the group consisting of a methyl group, a —CF 3 group, a fluorine atom and a chlorine atom, or a formula (RM -S21), but at least one of X M21 to X M25 represents the formula (RM-S21).)
(In the above formula (RM-S11) and the above formula (RM-S21), S M11 and S M21 each independently represents an alkylene group having 1 to 12 carbon atoms or a single bond, and — CH 2 — may be replaced by —O—, —COO—, —OCO—, or —OCOO— as those in which oxygen atoms are not directly bonded to each other,
R M11 and R M21 each independently represent the following formulas (R-1) to (R-15):

Represents one of the following:
L M1 and L M2 are each independently a single bond, —O—, —CH 2 —, —OCH 2 —, —CH 2 O—, —CO—, —C 2 H 4 —, —COO—, —OCO—, —CH═CH—COO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—OCO—, —COOC 2 H 4 —, —OCOC 2 H 4 —, -C 2 H 4 OCO -, - C 2 H 4 COO -, - OCOCH 2 -, - CH 2 COO -, - CH = CH -, - CF = CH -, - CH = CF -, - CF = CF- , -CF 2 -, - CF 2 O -, - OCF 2 -, - CF 2 CH 2 -, - CH 2 CF 2 -, - CF 2 CF 2 - or -C≡C- represent, L M2 is more If present, they may be the same or different. )
M M1 represents a 1,4-phenylene group, a 1,4-cyclohexylene group or a naphthalene-2,6-diyl group, and the hydrogen atom contained in these groups is a fluorine atom, a chlorine atom or a carbon atom An alkyl group of 1-8, halogenated alkyl group, halogenated alkoxy group, alkoxy group, nitro group or

( Wherein S M1 represents an alkylene group having 1 to 12 carbon atoms or a single bond, and —CH 2 — in the alkylene group represents an oxygen atom, —COO—, — OCO— or —OCOO— may be substituted, and R M1 represents any of the above formulas (R-1) to (R-15).
May be optionally substituted, if M M1 there are a plurality, they may be the same or different,
m M1 represents 0, 1 or 2.
When there are a plurality of S M11 , S M21 , S M1 , R M11 , R M21 and / or R M1 , they may be the same or different. "

“In the general formula (RM-2), X M1 to X M8 each independently represents a hydrogen atom or a fluorine atom,
S M2 and S M3 each independently represents an alkylene group having 1 to 12 carbon atoms or a single bond, and —CH 2 — in the alkylene group represents an oxygen atom, — May be replaced by COO-, -OCO- or -OCOO-,
R M2 and R M3 represent any of the above formulas (R-1) to (R-15). The liquid crystal composition according to claim 1, comprising one or more selected from the group consisting of a polymerizable compound represented by the formula:
Formula (II)

(In the general formula (II), R N1 and R N2 are each independently an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms. or an alkenyloxy group having 2 to 10 carbon atoms, R N1 and R N2 being present in one -CH 2 - or nonadjacent two or more -CH 2 - are each independently -O -And / or S- may be substituted, and one or two or more hydrogen atoms present in these groups may be independently substituted with a fluorine atom or a chlorine atom,
C N1 and D N1 are each independently a trans-1,4-cyclohexylene group (one or non-adjacent two or more —CH 2 — in the group is substituted by —O— or S—). 1), 4-phenylene group (one or two or more non-adjacent —CH═ in the group may be substituted by —N═), 2-fluoro-1,4 -Phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3 4-tetrahydronaphthalene-2,6-dii Group
m N1 and m N2 each independently represent 0, 1, 2 or 3, and Z N1 and Z N2 each independently represent —OCH 2 —, —CH 2 O—, —CF 2 O— , —OCF 2 —, —C 2 H 4 —, —CF 2 CF 2 — or a single bond, and when there are a plurality of C N1 , D N1 , Z N1 and / or Z N2 , they are the same Or different. The liquid crystal composition according to claim 1, comprising one or more compounds selected from the group of compounds represented by:
The general formula (II) is changed from the general formula (II-A1) to the general formula (II-A5), from the general formula (II-B1) to the general formula (II-B6), and from the general formula (II-C1) to the general formula (II). II-C4)

(In the above general formula, R N3 and R N4 each independently represents an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and 1 present in R N3 and R N4. The liquid crystal composition according to claim 4, wherein one or two or more hydrogen atoms may be each independently substituted with a fluorine atom or a chlorine atom.
Formula (III)

(In the general formula (III), R NP1 and R NP2 each independently represents an alkyl group having 1 to 10 carbon atoms, and one or non-adjacent two or more —CH in the alkyl group. 2 — each independently may be substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
m NP1 represents 0, 1, 2 or 3,
E NP1 , F NP1 and G NP1 are each independently a trans-1,4-cyclohexylene group (one or non-adjacent two or more —CH 2 — in the group is —O— or —S—). ), 1,4-phenylene group (one or two or more non-adjacent —CH═ in the group may be substituted by —N═), naphthalene-2 , 6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (naphthalene-2,6-diyl or 1,2,3 In the 4-tetrahydronaphthalene-2,6-diyl group, one —CH═ or two or more non-adjacent —CH═ may be replaced by —N═. The hydrogen atom contained in the group of It may be substituted with a fluorine atom or a chlorine atom,
Z NP1 and Z NP2 are each independently a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, — OCF 2 —, —CF 2 O—, —CH═NN—CH—, —CH═CH—, —CF═CF— or —C≡C—
When a plurality of F NP1 or Z NP2 are present, they may be the same or different. However, in general formula (III), the compounds represented by general formula (I) and general formula (II) are excluded. 6. The liquid crystal composition according to claim 1, which contains one or more compounds selected from the group of compounds represented by formula (1):
General formula (III) is changed from general formula (III-A) to general formula (III-J)

(Wherein R NP1 and R NP2 represent the same meaning as in general formula (III) described in claim 6, and X np1 and X np2 are each independently a hydrogen atom or a fluorine atom). The liquid crystal composition according to claim 6, comprising one or more compounds selected from the group.
The liquid crystal display element using the liquid-crystal composition of any one of Claim 1 to 7.
A liquid crystal display element for a PSA mode, a PSVA mode, a VA mode, an IPS mode, an FFS mode, or an ECB mode, using the liquid crystal composition according to claim 1.