WO2020121639A1 - Polymerizable compound-containing liquid crystal composition, liquid crystal display device, and polymerizable compound - Google Patents

Abstract

The present invention addresses the problem of providing: a polymerizable compound-containing a liquid crystal composition in which precipitation of a polymerizable compound is suppressed and with which a fast polymerization rate, a reduced residual amount of an unreacted polymerizable compound, a high voltage holding ratio (VHR), and a high tilt stability can be achieved at the same time; a liquid crystal display device using said liquid crystal composition; and a polymerizable compound suitable for the preparation of the polymerizable compound-containing liquid crystal composition. The present invention solves said problem by providing a liquid crystal composition which contains one or two or more polymerizable compounds represented by general formula (i).

Description

Polymerizable compound-containing liquid crystal composition, liquid crystal display device, and polymerizable compound

The present invention relates to a liquid crystal composition containing a polymerizable compound, a liquid crystal display device using the same, and a polymerizable compound. In the present specification, a liquid crystal composition containing a polymerizable compound is referred to as a polymerizable compound-containing liquid crystal composition. Further, the polymerizable compound means a compound having a polymerizable group.

A PSA (Polymer Sustained Alignment) type liquid crystal display element has a structure in which a polymer structure is formed in the cell to control the pretilt angle of liquid crystal molecules, and is used as a liquid crystal display element because of its high-speed response and high contrast. Has been transformed.

A PSA type liquid crystal display device is manufactured by injecting a liquid crystal composition containing a polymerizable compound between substrates, irradiating ultraviolet rays in a state in which a voltage is applied to align liquid crystal molecules to polymerize the polymerizable compound. This is done by fixing the orientation of liquid crystal molecules. As a polymerizable compound-containing liquid crystal composition suitable for this, in Patent Documents 1 to 3, the following compound (A) having a biphenyl skeleton or a compound (B) having a terphenyl skeleton as a polymerizable compound is described. , A liquid crystal composition containing a compound (C) having a cinnamic acid skeleton is disclosed.

International Publication No. 2010/084823 Japanese Patent Publication No. 2013-509457 JP, 2011-202168, A

In recent years, in the production of PSA type liquid crystal display elements, a polymerizable compound-containing liquid crystal composition having an appropriately high polymerization rate has been demanded for the purpose of improving production efficiency. However, since the liquid crystal composition containing the compound (A) as the polymerizable compound has an insufficient polymerization rate, a long UV irradiation time is required to reduce the residual amount of the polymerizable compound. Although the liquid crystal composition containing the compound (B) as the polymerizable compound has an appropriately high polymerization rate, display defects (burn-in) are likely to occur due to a large amount of change in the pretilt angle. The liquid crystal composition containing the compound (C) as the polymerizable compound has a problem that precipitation of the polymerizable compound is observed during storage. Therefore, it is required to improve the physical properties of the polymerizable compound-containing liquid crystal composition.

The problem to be solved by the present invention is that the precipitation of a polymerizable compound is suppressed, sufficient polymerization can be performed at a high speed, and a high voltage holding ratio (VHR) and high tilt stability can be achieved at the same time. It is to provide a liquid crystal composition, a liquid crystal display device using the same, and a polymerizable compound suitable for preparation of the polymerizable compound-containing liquid crystal composition.

As a result of diligent studies by the present inventors on the above problems, they have found that the above problems can be solved by a liquid crystal composition containing a polymerizable compound having a specific chemical structure, and have completed the present invention.

That is, the present invention has the general formula (i):

(In the formula, A ⁱ¹ and A ⁱ² are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═) and (c). Naphthalenediyl group, 1,2,3,4-tetrahydronaphthalenediyl group or decahydronaphthalenediyl group (one -CH= present in naphthalenediyl group or 1,2,3,4-tetrahydronaphthalenediyl group) Two or more -CH= that are not adjacent to each other may be replaced with -N=.)
Represents a group selected from the group consisting of: the group (a), the group (b) and the group (c) each independently represent an alkyl group having 1 to 8 carbon atoms and a group having 1 to 8 carbon atoms. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or P ⁱ³ —S ⁱ³ —,
P ⁱ¹ , P ^i2, and P ⁱ³ are each independently the formula (R-1) to the formula (R-9).

(In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and m ^r5 , m ^r7 , n ^r5 and n ^r7 each independently represent a group selected from 0, 1, or 2),
S ⁱ¹ , S ⁱ² and S ⁱ³ each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH ₂ — in the alkylene group or two or more not adjacent to each other. -CH _2- may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other,
R ⁱ¹ represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom,
n ⁱ¹ represents 1, 2 or 3,
When there are a plurality of A ⁱ² , S ⁱ² , P ⁱ³ and/or S ⁱ³ , they may be the same or different. The liquid crystal composition containing 1 type or 2 types or more of the polymeric compound represented by these.

The present invention also provides a liquid crystal display device, a liquid crystal display device for active matrix driving, a PSA mode, a PSVA mode, which uses a liquid crystal composition containing one or more polymerizable compounds represented by the general formula (i). Provided is a liquid crystal display device for PS-IPS mode or PS-FFS mode.

Further, the present invention provides a polymerizable compound represented by the above general formula (i).

According to the present invention, a low viscosity (η), a small rotational viscosity (γ1) and a large value are obtained without decreasing the refractive index anisotropy (Δn) and the nematic phase-isotropic liquid phase transition temperature (Tni). It is possible to provide a polymerizable compound-containing liquid crystal composition that exhibits an elastic constant (K33), suppresses precipitation of the polymerizable compound, has a sufficiently high polymerization rate of the polymerizable compound, and is sufficiently polymerizable. The liquid crystal display device using the polymerizable compound-containing liquid crystal composition of the present invention has a small residual amount of unreacted polymerizable compound, high voltage holding ratio (VHR), high-speed response, and high tilt stability. It is possible to exhibit excellent display quality in which there is no display defect such as alignment defect due to change in pretilt angle or display defect such as burn-in.

I. Polymerizable Compound-Containing Liquid Crystal Composition First, the polymerizable compound-containing liquid crystal composition of the present invention will be described. In the following description, "total amount" means "total mass", and the unit "%" of the content of each compound means "% by mass".

The polymerizable compound-containing liquid crystal composition of the present invention has the general formula (i):

(In the formula, A ⁱ¹ and A ⁱ² are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═) and (c). Naphthalenediyl group, 1,2,3,4-tetrahydronaphthalenediyl group or decahydronaphthalenediyl group (one -CH= present in naphthalenediyl group or 1,2,3,4-tetrahydronaphthalenediyl group) Two or more -CH= that are not adjacent to each other may be replaced with -N=.)
Represents a group selected from the group consisting of: the group (a), the group (b) and the group (c) each independently represent an alkyl group having 1 to 8 carbon atoms and a group having 1 to 8 carbon atoms. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or P ⁱ³ —S ⁱ³ —,
P ⁱ¹ , P ^i2, and P ⁱ³ are each independently the formula (R-1) to the formula (R-9).

(In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and m ^r5 , m ^r7 , n ^r5 and n ^r7 each independently represent a group selected from 0, 1, or 2),
S ⁱ¹ , S ⁱ² and S ⁱ³ each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH ₂ — in the alkylene group or two or more not adjacent to each other. -CH _2- may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other,
R ⁱ¹ represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom,
n ⁱ¹ represents 1, 2 or 3,
When there are a plurality of A ⁱ² , S ⁱ² , P ⁱ³ and/or S ⁱ³ , they may be the same or different. ) A liquid crystal composition containing one or more polymerizable compounds represented by the formula (1).

According to the present invention, the precipitation of the polymerizable compound represented by the general formula (i) is small, the polymerization rate of the polymerization compound is sufficiently high, and the polymerization reaction proceeds sufficiently. A liquid crystal composition containing a polymerizable compound having a small residual amount of the compound can be obtained. The polymerizable compound-containing liquid crystal composition of the present invention can have the above-mentioned characteristics while satisfying various characteristics required for a liquid crystal display device such as high-speed response, high contrast, and low power consumption. Further, by using the polymerizable compound-containing liquid crystal composition of the present invention, it is possible to suppress the occurrence of display defects (burn-in) due to changes in the pretilt angle, and to simultaneously achieve high voltage holding ratio (VHR) and high tilt stability. An achievable liquid crystal display device can be manufactured.

Thus, the polymerizable compound-containing liquid crystal composition of the present invention is useful for producing a PSA-type or PSVA-type liquid crystal display device having excellent reliability after the ultraviolet irradiation step. Further, according to the polymerizable compound-containing liquid crystal composition of the present invention, it is possible to control the tilt angle and the residual amount of the polymerizable compound, so that the energy cost for manufacturing a liquid crystal display device can be optimized and reduced. Therefore, the production efficiency of the liquid crystal display device can be easily improved. Therefore, the polymerizable compound-containing liquid crystal composition of the present invention and the liquid crystal display device using the same are very useful.

(Polymerizable compound)
The polymerizable compound essentially contained in the present invention is represented by the above general formula (i).

In the general formula (i), A ⁱ¹ and A ⁱ² are
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═) and (c). Naphthalenediyl group, 1,2,3,4-tetrahydronaphthalenediyl group or decahydronaphthalenediyl group (one -CH= present in naphthalenediyl group or 1,2,3,4-tetrahydronaphthalenediyl group) Two or more -CH= that are not adjacent to each other may be replaced with -N=.)
Represents a group selected from the group consisting of

Here, the naphthalenediyl group which A ⁱ¹ and A ⁱ² can take is one of two positions selected from the 1 to 8 positions, which is bonded to S ⁱ¹ or S ⁱ² and, on the other hand, in the above general formula (i). It is a group that binds to a structural site represented by the following formula (hereinafter referred to as a specific structural site).

(In the above formula, * ^connects with A ^i2, and ★★ connects with A ⁱ¹ .)

Examples of the naphthalenediyl group include naphthalene-1,2-diyl group, naphthalene-1,3-diyl group, naphthalene-1,4-diyl group, naphthalene-1,5-diyl group, naphthalene-1,6-diyl group. Group, naphthalene-1,7-diyl group, naphthalene-1,8-diyl group, naphthalene-2,3-diyl group, naphthalene-2,6-diyl group, naphthalene-2,7-diyl group and the like. ..

Further, the 1,2,3,4-tetrahydronaphthalenediyl group which A ⁱ¹ and A ⁱ² can have is a bond with S ⁱ¹ or S ⁱ² at one of two positions selected from 1 to 8 and the other. It is a group that binds to the above-mentioned specific structural site in the general formula (i). Examples of the 1,2,3,4-tetrahydronaphthalenediyl group include a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group and 1,2,3,4-tetrahydronaphthalene-1,4-diyl group. Group, 1,2,3,4-tetrahydronaphthalene-1,5-diyl group and the like. In addition, the decahydronaphthalenediyl group which A ⁱ¹ and A ⁱ² can take is one of two positions selected from the 1 to 10 positions, which is bonded to S ⁱ¹ or S ^i2, and the other is a general formula (i). It is a group that binds to the above-mentioned specific structure site. Examples of the decahydronaphthalenediyl group include a decahydronaphthalene-2,6-diyl group.

The above group (a), group (b) and group (c) are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen, a cyano group or a nitro group. Alternatively, it may be substituted with P ⁱ³ −S ⁱ³ −.

Above all, it is preferable that A ⁱ¹ and A ⁱ² each independently represent one of the following structures.

(In the formula, R ⁱ² and R ⁱ³ each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a fluorine atom or P ⁱ³ —S ⁱ³ —)

A ⁱ¹ and A ⁱ² are each independently 1,4-phenylene group, 2-methyl-1,4-phenylene group, 3-methyl-1,4-phenylene group, 2-methoxy-1,4- More preferably, it is a phenylene group, 3-methoxy-1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group or naphthalene-2,6-diyl group. , 1,4-phenylene group, 2-fluoro-1,4-phenylene group or 3-fluoro-1,4-phenylene group is more preferable, and 1,4-phenylene group is particularly preferable.

In the general formula (i), the number of rings represented by A ⁱ¹ is one. On the other hand, in the general formula (i), the number of rings represented by A ⁱ² is one or two or more depending on the number of n ⁱ¹ . The polymerizable compound represented by the general formula (i) has such a structure, so that the ring represented by A ⁱ¹ in the general formula (i) such as the compound (C) described above has 2 rings. It is presumed that the solubility is improved as compared with one or more polymerizable compounds, and as a result, precipitation is less likely to occur. If the A ⁱ² is more, all the plurality of A ⁱ² may be the same group or may be different groups.

In the general formula (i), P ⁱ¹ , P ⁱ² and P ⁱ³ each independently represent a group selected from the above formulas (R-1) to (R-9). P ⁱ¹ , P ⁱ² and P ⁱ³ may all be the same polymerizable group (formula (R-1) to (R-9)) or at least one group may be different. , All may be different polymerizable groups. Both P ⁱ¹ and P ⁱ² may be the same polymerizable group or different polymerizable groups, but when P ⁱ¹ and P ⁱ² are the same polymerizable group, the compound represented by the general formula (i) It has an advantage that the compound represented by is easy to synthesize. Also, if the P ⁱ³ there are multiple, all of the plurality of P ⁱ³ may be the same group or may be different groups.

In the general formula (i), P ⁱ¹ , P ⁱ² and P ⁱ³ are each independently a formula (R-1), a formula (R-2), a formula (R-3) and a formula (R-4). , Formula (R-5) or formula (R-7), preferably formula (R-1), formula (R-2), formula (R-3) or formula (R-4) Is more preferable, formula (R-1) is more preferable, and acryloxy group or methacryloxy group is particularly preferable.

Further, among P ⁱ¹ , P ⁱ² and P ⁱ³ , at least one of P ⁱ¹ and P ⁱ² is preferably the formula (R-1), more preferably an acryloxy group or a methacryloxy group, A methacryloxy group is more preferred, and it is particularly preferred that both P ⁱ¹ and P ⁱ² are methacryloxy groups. This is because when both P ⁱ¹ and P ⁱ² are methacryloxy groups, display defects due to changes in the pretilt angle are less likely to occur when used in a liquid crystal display element. Also, the degree of polymerization of the polymerizable compound can be increased as compared with the case where both P ⁱ¹ and P ⁱ² are acryloxy groups.

In the general formula (i), R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ in the formulas (R-1) to (R-9) each independently have 1 to 5 carbon atoms. Represents either an alkyl group, a fluorine atom or a hydrogen atom. Among them, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are each independently preferably a methyl group or a hydrogen atom, and are hydrogen atoms when the polymerization rate of the polymerizable compound is important. Is preferred, and a methyl group is preferred when importance is attached to reduction of display defects due to changes in the pretilt angle.

Further, m ^r5 , m ^r7 , n ^r5 and n ^r7 in formulas (R-1) to (R-9) each independently represent 0, 1 or 2.

In the general formula (i), S ⁱ¹ , S ⁱ² and S ⁱ³ each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms. One -CH ₂ in the alkylene group - or nonadjacent two or more -CH ₂ -, as the oxygen atoms are not directly adjacent, -O -, - OCO- or -COO- in substituted May be. Among them, S ⁱ¹ , S ⁱ² and S ⁱ³ are each independently preferably a single bond or an alkylene group having 1 to 5 carbon atoms, and particularly preferably a single bond. When S ⁱ¹ , S ^i2, and S ⁱ³ are single bonds, the residual amount of the polymerizable compound after the irradiation of ultraviolet rays is sufficiently small, and display defects due to changes in the pretilt angle are less likely to occur. If S ⁱ² have multiple all of the plurality of ^{S i2} may be the same or different all ^{S i2} or at least one ^{S i2.}

In the above general formula (i), ⁿⁱ¹ represents 1, 2 or 3, but it is more preferably 1 or 2 since the solubility in the liquid crystal composition is good, and the solubility in the liquid crystal composition is more preferable. It is particularly preferable that it is 1, since it is more favorable.

In the general formula (i), R ⁱ¹ represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and among them, R ⁱ¹ is a methyl group, an ethyl group, a fluorine atom or a hydrogen atom. Is preferred, and a hydrogen atom is more preferred.

In the polymerizable compound-containing liquid crystal composition of the present invention, the lower limit of the content of the polymerizable compound represented by the general formula (i) is preferably 0.01%, preferably 0.02%, and 0.03%. Preferably, 0.04% is preferable, 0.05% is preferable, 0.06% is preferable, 0.07% is preferable, 0.08% is preferable, 0.09% is preferable, 0.1% is preferable. 0.12% is preferred, 0.15% is preferred, 0.17% is preferred, 0.2% is preferred, 0.22% is preferred, 0.25% is preferred, 0.27% is preferred, 0.3% is preferred, 0.32% is preferred, 0.35% is preferred, 0.37% is preferred, 0.4% is preferred, 0.42% is preferred, 0.45% is preferred, 0 0.5% is preferable and 0.55% is preferable. In the polymerizable compound-containing composition of the present invention, the upper limit of the content of the polymerizable compound represented by formula (i) is preferably 5%, 4.5%, preferably 4%, 3.5. % Is preferred, 3% is preferred, 2.5% is preferred, 2% is preferred, 1.5% is preferred, 1% is preferred, 0.95% is preferred, 0.9% is preferred, 0.85 % Is preferred, 0.8% is preferred, 0.75% is preferred, 0.7% is preferred, 0.65% is preferred, 0.6% is preferred, 0.55% is preferred, 0.5% Is preferable, 0.45% is preferable, and 0.4% is preferable.

More specifically, in order to obtain a small residual amount of the polymerizable compound or a high voltage holding ratio (VHR), the content of the polymerizable compound represented by the general formula (i) in the polymerizable compound-containing liquid crystal composition is 0. It is preferably within the range of 0.2% to 1.5%. When importance is attached to suppression of precipitation of the polymerizable compound at low temperatures, the content of the polymerizable compound represented by the general formula (i) in the polymerizable compound-containing liquid crystal composition is 0.01% to 1.0%. It is preferably within the range of %. Furthermore, when the polymerizable compound-containing liquid crystal composition of the present invention contains a plurality of polymerizable compounds represented by the general formula (i), the content of each is within the range of 0.01% to 0.6%. Is preferred. Therefore, in order to solve all of these problems, it is particularly desirable to adjust the polymerizable compound represented by the general formula (i) in the range of 0.1% to 1.0%.

As the polymerizable compound represented by the general formula (i), specifically, compounds represented by the general formulas (i-1) to (i-33) are preferable.

(In the formula, R ⁱ⁴ and R ⁱ⁵ each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom.)

In the above formula, R ⁱ⁴ and R ⁱ⁵ are each independently an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and among them, a methyl group or a hydrogen atom is preferable.

Among the compounds represented by the above general formulas (i-1) to (i-33), the compounds represented by the general formulas (i-1) to (i-12) or the general formulas (i-12) or The compounds represented by the formulas (i-17) to (i-33) are more preferable, and in addition to the above-mentioned viewpoints, the compounds represented by the general formula (i-1) from the viewpoint of good tilt stability (hard to cause seizure) The compounds represented by general formula (i-12), general formula (i-23) to general formula (i-26), or general formula (i-28) to general formula (i-33) are more preferable, and In addition to the above, from the viewpoint of good solubility in the liquid crystal composition, high tilt stability, and sufficient polymerization at a high speed, the compounds of the general formula (i-1) to the general formula (i-5), The compound represented by the general formula (i-25), the general formula (i-26), or the general formula (i-28) to the general formula (i-33) is more preferable, and the compound represented by the general formula (i-1) is The compounds represented are particularly preferred.

(Liquid crystal composition)
In the polymerizable compound-containing liquid crystal composition of the present invention, the liquid crystal composition is a host liquid crystal to which the polymerizable compound represented by the general formula (i) is added, and contains at least the liquid crystal compound. The liquid crystal composition preferably contains one kind or two or more kinds of compounds selected from the compounds represented by the general formulas (N-1), (N-2) and (N-3). These compounds correspond to dielectrically negative compounds (the sign of Δε is negative and the absolute value thereof is larger than 2).

(In the formula, each of R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31, and R ^N32 independently represents an alkyl group having 1 to 8 carbon atoms, and one of the alkyl groups or a non-adjacent group is present. Two or more —CH ₂ — of each may independently be substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are each independently (a) a 1,4-cyclohexylene group (one —CH ₂ — present in this group or adjacent Two or more —CH ₂ — which are not present may be replaced by —O—.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced with —N═).
(C) 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 One -CH= present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more -CH= not adjacent to each other may be replaced by -N=. ) And (d) represents a group selected from the group consisting of 1,4-cyclohexenylene groups, wherein the groups (a), (b), (c) and (d) are each independently cyano. A group, which may be substituted with a fluorine atom or a chlorine atom,
Z ^N11 , Z ^N12 , Z ^N21 , Z ^N22 , Z ^N31 and Z ^N32 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- Represents
X ^N21 represents a hydrogen atom or a fluorine atom,
T ^N31 represents —CH ₂ — or an oxygen atom,
n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, and n ^N11 +n ^N12 , n ^N21 +n ^N22 and n ^N31 +n ^N32 are respectively Independently, 1, 2 or 3, and when there are a plurality of A ^N11 to A ^N32 and Z ^N11 to Z ^N32 , they may be the same or different. )

The compounds represented by the general formulas (N-1), (N-2) and (N-3) are preferably compounds having a negative Δε and an absolute value larger than 3.

In the general formulas (N-1), (N-2) and (N-3), R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31 and R ^N32 each independently have 1 to 10 carbon atoms. 8 represents an alkyl group, and one or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —CH═CH—, —C≡C—, —O—, —CO— , -COO- or -OCO-. Among them, R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31, and R ^N32 are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or 2 to 8 carbon atoms. An alkenyl group having 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or a carbon atom. An alkenyloxy group having 2 to 5 carbon atoms is preferable, an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferable, an alkyl group having 2 to 5 carbon atoms or 2 to 3 carbon atoms. Is more preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.

Further, R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31 and R ^{N32 each} have a linear carbon number of 1 to 5 when the ring structure to which they are bonded is a phenyl group (aromatic). The alkyl group, the straight-chain alkoxy group having 1 to 4 carbon atoms and the alkenyl group having 4 to 5 carbon atoms are preferable. , ^RN11 , ^RN12 , ^RN21 , ^RN21 , ^RN22 , ^RN31 and ^RN32 are linear carbon atoms when the ring structure to which they are bonded is a saturated ring structure such as cyclohexane, pyran and dioxane. Preferred are an alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31 and R ^N32 preferably have a total of carbon atoms and oxygen atoms, if any, of 5 or less, and a straight chain. It is preferably in the form of a circle.

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

In the general formulas (N-1), (N-2) and (N-3), A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are each independently (a) 1,4 - cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced with —N═).
(C) 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 One -CH= present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more -CH= not adjacent to each other may be replaced by -N=. ) And (d) represents a group selected from the group consisting of 1,4-cyclohexenylene groups.

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

A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are preferably aromatic when it is required to independently increase Δn, and fat is used to improve the response speed. It is preferably a family. The above-mentioned group (a), group (b), group (c) and group (d) are trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group. 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- It is preferable to represent a tetrahydronaphthalene-2,6-diyl group, and it is more preferable to represent the following structure:

It is particularly preferable to represent a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group.

In formulas (N-1), (N-2) and (N-3), Z ^N11 , Z ^N12 , Z ^N21 , Z ^N22 , Z ^N31 and Z ^N32 are each independently a single bond or —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 represents a -C≡C-, inter alia _{-CH 2 O -, - CF 2} O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably represents a single _{bond, -CH 2 O -, - CH} 2 CH 2 - or a single bond is more preferable, _-CH 2 O-or a single bond is particularly preferred.

In formulas (N-1), (N-2) and (N-3), X ^N21 represents a hydrogen atom or a fluorine atom, and among them, a fluorine atom is preferable.

In formulas (N-1), (N-2) and (N-3), T ^N31 represents —CH ₂ — or an oxygen atom, and among them, an oxygen atom is preferable.

In the general formulas (N-1), (N-2) and (N-3), n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 are each independently an integer of 0 to 3. Represents. In addition, n ^N11 +n ^N12 , n ^N21 +n ^N22, and n ^N31 +n ^N32 are 1, 2 or 3 independently. Among them, n ^N11 +n ^N12 , n ^N21 +n ^N22, and n ^N31 +n ^N32 are preferably 1 or 2, and at this time, a combination in which n ^N11 is 1 and n ^N12 is 0, n ^N11 is 2 and n ^N12 is 0. A combination, a combination in which n ^N11 is 1 and n ^N12 is 1, a combination in which n ^N11 is 2 and n ^N12 is 1, a combination in which n ^N21 is 1 and n ^N22 is 0, n ^N21 is 2 A combination in which n ^N22 is 0, a combination in which n ^N31 is 1 and n ^N32 is 0, and a combination in which n ^N31 is 2 and n ^N32 is 0 are preferable.

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

The lower limit of the preferred content of the compound represented by formula (N-2) based on the total amount of the liquid crystal composition is 1%, 10%, 20%, 30%, 40 %, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. Is.

The lower limit of the preferred content of the compound represented by formula (N-3) based on the total amount of the liquid crystal composition is 1%, 10%, 20%, 30%, 40 %, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The preferable upper limit of the content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%. Is.

When a composition that keeps the viscosity of the liquid crystal composition low and has a high response speed is required, it is preferable that the lower limit value and the upper limit value are low. When a composition having a high Tni and high temperature stability is required for the liquid crystal composition, it is preferable that the lower limit value is low and the upper limit value is low. Further, 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 high and the upper limit value is high.

Examples of the compound represented by the general formula (N-1) include compounds represented by the following general formulas (N-1a) to (N-1g).

^{(Wherein, R N11} and ^{R N12} are as defined ^{R N11} and ^{R N12} in the general formula ^{(N-1), n Na11} represents 0 or ^{1, n NB11} is 1 or ^{2, n NC11} is 0 or 1, n ^Nd11 represents 1 or 2, n ^Ne11 represents 1 or 2, n ^Nf12 represents 1 or 2, n ^Ng11 represents 1 or 2, and A ^Ne11 represents trans-1,4. ^{Represents a} cyclohexylene group or a 1,4-phenylene group, A ^Ng11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group, and n ^Nd11 Is 2, at least one of A ^Ng11 represents a 1,4-cyclohexenylene group, Z ^Ne11 represents a single bond or ethylene, but at least one existing in the molecule represents ethylene, and a plurality of them in the molecule. The existing A ^Ne11 , Z ^Ne11 , and/or A ^Ng11 may be the same or different.)

More specifically, the compound represented by the general formula (N-1) is a compound selected from the group of compounds represented by the general formulas (N-1-1) to (N-1-21). Is preferred.

The compound represented by the general formula (N-1-1) is the following compound.

(In the formula, R ^N111 and R ^N112 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group, pentyl group or vinyl group. R ^N112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group or a butoxy group.

The compound represented by the general formula (N-1-1) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the formula (N-1-1) is preferably set higher when the improvement of Δε is important, and is higher when the solubility at low temperature is important. The effect is high when the content is set high, and the effect is high when the content is set low when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-1) with respect to the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%. The preferable upper limit of the content is 50%, 40%, 38%, 35%, 33%, 30%, 28% with respect to the total amount of the liquid crystal composition. Yes, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% Yes, 5%, 3%.

The compound represented by the general formula (N-1-1) is a compound selected from the group of compounds represented by the formulas (N-1-1.1) to (N-1-1.25). Are preferred, and compounds represented by formulas (N-1-1.1) to (N-1-1.4) are preferred, and formulas (N-1-1.1) and (N-1) Compounds represented by -1.3) are preferred.

The compounds represented by the formulas (N-1-1.1) to (N-1-1.25) can be used alone or in combination. The lower limit of the preferable content of the compound alone or with respect to the total amount of the liquid crystal composition is 5%, 10%, 13%, 15%, 17%, 20%. Yes, 23%, 25%, 27%, 30%, 33%, 35%. The preferable upper limit of the content is 50%, 40%, 38%, 35%, 33%, 30%, 28% with respect to the total amount of the liquid crystal composition. Yes, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% Yes, 5%, 3%.

The compound represented by the general formula (N-1-2) is the following compound.

(In the formula, R ^N121 and R ^N122 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group or a pentyl group. R ^N122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group. preferable.

The compound represented by the general formula (N-1-2) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-2) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important. The effect is high when the content is set low, and the effect is high when the content is set high when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-2) with respect to the total amount of the liquid crystal composition is 5%, 7%, 10%, and 13%. , 15%, 17%, 20%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37% , 40% and 42%. The preferable upper limit of the content is 50%, 48%, 45%, 43%, 40%, 38%, 35% with respect to the total amount of the liquid crystal composition. Yes, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10% Yes, 8%, 7%, 6%, 5%.

The compound represented by the general formula (N-1-2) is a compound selected from the group of compounds represented by the formula (N-1-2.1) to the formula (N-1-2.25). Are preferred, and formula (N-1-2.3) to formula (N-1-2.7), formula (N-1-2.10), formula (N-1-2.11), formula (N -1-2.13) and the compound represented by the formula (N-1-2.20) are preferable, and when the improvement in Δε is emphasized, the compounds represented by the formula (N-1-2.3) The compound represented by (N-1-2.7) is preferable, and when importance is attached to the improvement of Tni, the formula (N-1-2.10), the formula (N-1-2.11) and the formula (N-1-2.11) The compound represented by formula (N-1-2.13) is preferable, and the compound represented by formula (N-1-2.20) is preferable when the improvement in response speed is emphasized.

The compounds represented by formulas (N-1-2.1) to (N-1-2.25) can be used alone or in combination, but the total amount of the liquid crystal composition is The lower limit of the preferred content of these compounds alone or with respect to is 5%, 10%, 13%, 15%, 17%, 20% and 23%. Yes, 25%, 27%, 30%, 33%, 35%. The preferable upper limit of the content is 50%, 40%, 38%, 35%, 33%, 30%, 28% with respect to the total amount of the liquid crystal composition. Yes, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6% Yes, 5%, 3%.

The compound represented by the general formula (N-1-3) is the following compound.

(In the formula, R ^N131 and R ^N132 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group. R ^N132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably a 1-propenyl group, an ethoxy group, a propoxy group or a butoxy group. ..

The compound represented by the general formula (N-1-3) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the formula (N-1-3) is preferably set higher when the improvement of Δε is important, and is higher when the solubility at low temperature is important. The effect is high when the content is set high, and the effect is high when the content is set high when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-3) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-3) is a compound selected from the group of compounds represented by the formula (N-1-3.1) to the formula (N-1-3.21). Are preferably the compounds represented by the formulas (N-1-3.1) to (N-1-3.7) and the formula (N-1-3.21), and the compounds represented by the formula (N-1 -3.1), formula (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) and formula (N-1-3.6) The compounds represented by the formulas (N-1-3.3), (N-1-3.4) and (N-1-3.6) are preferred.

The compounds represented by the formula (N-1-3.1) to the formula (N-1-3.4), the formula (N-1-3.6) and the formula (N-1-3.21) are independent. Although they can be used in combination with each other or in combination, the combination of formula (N-1-3.1) and formula (N-1-3.2), formula (N-1-3.3) ), the formula (N-1-3.4) and the formula (N-1-3.6), and a combination of two or three kinds thereof is preferable, and the formula (N-1-3.3) and the formula (N −1-3.4) and the formula (N-1-3.6) are preferably used in combination. The lower limit of the preferable content of the compound alone or with respect to the total amount of the liquid crystal composition is 5%, 10%, 13%, 15%, 17%, 20%. is there. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-4) is the following compound.

^{(Wherein, R N141} and ^{R N142} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

R ^N141 and ^{R N142} are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group or an alkoxy group having 1 to 4 carbon atoms carbon atoms 4-5 preferably a methyl group, a propyl group, an ethoxy A group or butoxy group is preferred.

The compound represented by the general formula (N-1-4) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-4) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important, the content is preferably set higher. The effect is high when the content is set high, and the effect is high when the content is set low when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-4) based on the total amount of the liquid crystal composition is 3%, 5%, 7%, and 10%. , 13%, 15%, 17%, 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%, 11%, 10%, 8%.

The compound represented by the general formula (N-1-4) is a compound selected from the group of compounds represented by the formulas (N-1-4.1) to (N-1-4.24). Are preferred, and compounds represented by formulas (N-1-4.1) to (N-1-4.4) are preferred. Formulas (N-1-4.1) and (N-1) -4.2) and compounds represented by the formula (N-1-4.4) are preferred.

The compounds represented by the formulas (N-1-4.1) to (N-1-4.24) can be used alone or in combination, but the amount is not limited to the total amount of the liquid crystal composition. On the other hand, the lower limit of the preferable content of the compound alone or these compounds is 3%, 5%, 7%, 10%, 13%, 15%, 17%. , 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%, 11%, 10%, 8%.

The compound represented by the general formula (N-1-5) is the following compound.

(In the formula, R ^N151 and R ^N152 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N151 and R ^N152 are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. Is preferred.

The compound represented by the general formula (N-1-5) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-5) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important. The effect is high when the content is set low, and the effect is high when the content is set high when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-5) based on the total amount of the liquid crystal composition is 5%, 8%, 10%, and 13%. , 15%, 17% and 20%. The upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, 23%, 20% with respect to the total amount of the liquid crystal composition. Yes, 18%, 15%, 13%.

The compound represented by the general formula (N-1-5) is a compound selected from the group of compounds represented by the formulas (N-1-5.1) to (N-1-5.12). Are preferred, and compounds represented by formula (N-1-5.1), formula (N-1-5.2) and formula (N-1-5.4) are preferred.

The compounds represented by formula (N-1-5.1), formula (N-1-5.2) and formula (N-1-5.4) may be used alone or in combination. However, the lower limit of the preferable content of the compound alone or in the total amount of the liquid crystal composition is 5%, 8%, 10%, 13%, 15% with respect to the total amount of the liquid crystal composition. And 17% and 20%. The upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, 23%, 20% with respect to the total amount of the liquid crystal composition. Yes, 18%, 15%, 13%.

The compound represented by the general formula (N-1-10) is the following compound.

(In the formula, R ^N1101 and R ^N1102 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N1101 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. R ^N1102 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compound represented by the general formula (N-1-10) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-10) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important. The effect is high when the content is set high, and the effect is high when the content is set low when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-10) is 5%, 10%, 13%, and 15% with respect to the total amount of the liquid crystal composition. , 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-10) is a compound selected from the group of compounds represented by the formulas (N-1-10.1) to (N-1-10.14). Compounds represented by Formulas (N-1-10.1) to (N-1-10.5) are preferred, and Formulas (N-1-10.1) and (N-1) are preferred. Compounds represented by -10.2) are preferable.

The compounds represented by formula (N-1-10.1) and formula (N-1-10.2) can be used alone or in combination, but the total amount of the liquid crystal composition is not limited. The lower limit of the preferred content of these compounds alone or with respect to is 5%, 10%, 13%, 15%, 17%, 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-11) is the following compound.

(In the formula, R ^N1111 and R ^N1112 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N1111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. R ^N1112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.

The compound represented by the general formula (N-1-11) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-11) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important. The effect is high when the content is set low, and the effect is high when the content is set high when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-11) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-11) is a compound selected from the group of compounds represented by the formulas (N-1-11.1) to (N-1-11.14). Are preferred, and compounds represented by formulas (N-1-11.1) to (N-1-11.14) are preferred. Formulas (N-1-11.2) and (N-1) -11.4) is preferred.

The compounds represented by formula (N-1-11.2) and formula (N-1-11.4) can be used alone or in combination, but the total amount of the liquid crystal composition is not limited. The lower limit of the preferred content of these compounds alone or with respect to is 5%, 10%, 13%, 15%, 17%, 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compounds represented by the general formula (N-1-12) are the following compounds.

(In the formula, R ^N1121 and R ^N1122 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group. R ^N1122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group or a butoxy group.

The compound represented by the general formula (N-1-12) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-12) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important. The effect is high when the content is set high, and the effect is high when the content is set low when Tni is important. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-12) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compounds represented by the general formula (N-1-13) are the following compounds.

(In the formula, R ^N1131 and R ^N1132 each independently have the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N1131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably an ethyl group, a propyl group or a butyl group. R ^N1132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.

The compound represented by the general formula (N-1-13) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-13) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important, the content is preferably set higher. If the content is set high, the effect is high, and if Tni is important, the content is set high, the effect is high. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-13) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-14) is the following compound.

(In the formula, R ^N1141 and R ^N1142 each independently have the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N1141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a methyl group, an ethyl group, a propyl group or a butyl group. R ^N1142 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group, a propoxy group or a butoxy group.

The compound represented by the general formula (N-1-14) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-14) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important. If the content is set high, the effect is high, and if Tni is important, the content is set high, the effect is high. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-14) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-14) is a compound selected from the group of compounds represented by the formulas (N-1-14. 1) to (N-1-14.5). Are preferred, and compounds represented by formulas (N-1-14.1) to (N-1-14.3.) are preferred, and formulas (N-1-14.2) and (N-1) are preferred. The compound represented by -14.3) is preferable.

The compound represented by the general formula (N-1-20) is the following compound.

(In the formula, R ^N1201 and R ^N1202 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N1201 and R ^N1202 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.

The compound represented by the general formula (N-1-20) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-20) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important. If the content is set high, the effect is high, and if Tni is important, the content is set high, the effect is high. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-20) based on the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-21) is the following compound.

(In the formula, R ^N1211 and R ^N1212 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N1211 and R ^N1212 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.

The compound represented by the general formula (N-1-21) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-21) is preferably set higher when the improvement in Δε is important, and is included when the solubility at low temperature is important. The effect is high when the amount is set high, and the effect is high when the content is set high when Tni is important. Furthermore, in the case of improving the drop mark and the seizure property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-21) with respect to the total amount of the liquid crystal composition is 5%, 10%, 13%, and 15%. , 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%.

The compound represented by the general formula (N-1-22) is the following compound.

(In the formula, R ^N1221 and R ^N1222 each independently represent the same meaning as R ^N11 and R ^N12 in the general formula (N-1).)

R ^N1221 and R ^N1222 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.

The compound represented by the general formula (N-1-22) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The content of the compound represented by the general formula (N-1-22) is preferably set higher when the improvement of Δε is important, and when the solubility at low temperature is important. If the content is set high, the effect is high, and if Tni is important, the content is set high, the effect is high. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (N-1-22) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 13%. , 15%, 17% and 20%. The preferable upper limit of the content is 35%, 30%, 28%, 25%, 23%, 20%, 18% with respect to the total amount of the liquid crystal composition. Yes, 15%, 13%, 10%, 5%.

The compound represented by the general formula (N-1-22) is a compound selected from the group of compounds represented by the formula (N-1-22.12) to the formula (N-1-22.12). Are preferred, and compounds represented by formulas (N-1-22.1) to (N-1-22.5) are preferred, and compounds represented by formulas (N-1-22.1) to (N-1-) are preferred. The compound represented by 22.4) is preferable.

The liquid crystal composition preferably contains one kind or two or more kinds of compounds represented by the general formula (L). The compound represented by the general formula (L) corresponds to a dielectrically almost neutral compound (Δε value is −2 to −2). Therefore, the number of polar groups such as halogens in the molecule is preferably 2 or less, more preferably 1 or less, and preferably not.

(In the formula, R ^L1 and R ^L2 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — groups in the alkyl group are independent of each other. And may be substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
n ^L1 represents 0, 1, 2 or 3,
A ^L1 , A ^L2 and A ^L3 are each independently (a) a 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more —CH ₂ which are not adjacent to each other). -May be replaced with -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═) and (c). 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 , -CH= present in the 3,3,4-tetrahydronaphthalene-2,6-diyl group or two or more -CH= not adjacent to each other may be replaced with -N=.)
Represents a group selected from the group consisting of, the above groups (a), (b) and (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^L1 and Z ^L2 are each independently a single bond, —CH ₂ CH ₂ —, —(CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —. Represents OCF ₂ —, —CF ₂ O—, —CH═NN═CH—, —CH═CH—, —CF═CF— or —C≡C—,
When n ^L1 is 2 or 3 and a plurality of A ^L2 are present, they may be the same or different, and when n ^L1 is 2 or 3 and Z ^L2 is present a plurality of them. May be the same or different. However, compounds represented by formulas (N-1), (N-2) and (N-3) are excluded. )

The compounds represented by the general formula (L) may be used alone or in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The type of compound used is, for example, one type in one embodiment of the present invention. Alternatively, in another embodiment of the present invention, there are two types, three types, four types, five types, six types, seven types, eight types, nine types, and ten types. More than type.

In the liquid crystal composition, the content of the compound represented by the general formula (L) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the drop mark, the burn-in, the dielectric constant. It is necessary to appropriately adjust according to required performance such as anisotropy.

The lower limit of the preferred content of the compound represented by formula (L) with respect to the total amount of the liquid crystal composition is 1%, 10%, 20%, 30%, and 40%. Yes, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%.

When a composition that keeps the viscosity of the liquid crystal composition low and has a high response speed is required, it is preferable that the content of the compound represented by the formula (L) has a high lower limit and a high upper limit. When a composition having a high Tni and high temperature stability is required for the liquid crystal composition, the lower limit of the content of the compound represented by formula (L) is preferably high and the upper limit thereof is preferably high. When it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable that the lower limit of the content of the compound represented by the formula (L) is low and the upper limit thereof is low.

In the general formula (L), both R ^L1 and R ^L2 are preferably alkyl groups when importance is placed on reliability, and alkoxy groups when importance is placed on reducing the volatility of the compound. Is preferred, and when importance is attached to the reduction of viscosity, at least one is preferably an alkenyl group.

In the general formula (L), the number of halogen atoms present in the molecule is preferably 0, 1, 2 or 3, and 0 or 1 is preferable, and 1 is preferable when the compatibility with other liquid crystal molecules is important. ..

In the above general formula (L), R ^L1 and R ^L2 are a linear alkyl group having 1 to 5 carbon atoms or a linear alkyl group when the ring structure to which it is bonded is a phenyl group (aromatic). Preferred are an alkoxy group having 1 to 4 carbon atoms and an alkenyl group having 4 to 5 carbon atoms. On the other hand, R ^L1 and R ^L2 are each a linear alkyl group having 1 to 5 carbon atoms or a linear alkyl group having a saturated ring structure such as cyclohexane, pyran or dioxane to which it is bonded. An alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, each of R ^L1 and R ^L2 preferably has a total of 5 or less carbon atoms and oxygen atoms, if any, and is preferably linear.

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

In the general formula (L), n ^L1 is preferably 0 when importance is attached to the response speed, 2 or 3 is preferable for improving the maximum temperature of the nematic phase, and 1 is preferable for achieving a balance between them. preferable. Further, in order to satisfy the properties required for the composition, it is preferable to combine compounds having different values of n ^L1 .

In the general formula (L), A ^L1 , A ^L2, and A ^L3 are preferably aromatic when it is required to increase Δn, and are aliphatic in order to improve the response speed. preferable. A ^L1 , A ^L2 and A ^L3 are each independently a 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 It is preferable to represent a -2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and it is more preferable to represent the following structure. Preferably

It is particularly preferable to represent a trans-1,4-cyclohexylene group or a 1,4-phenylene group.

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

The compound represented by the general formula (L) preferably has 0 or 1 halogen atom in the molecule.

The compound represented by the general formula (L) is preferably a compound selected from the group of compounds represented by the general formulas (L-1) to (L-7).

The compound represented by the general formula (L-1) is the following compound.

(In the formula, R ^L11 and R ^L12 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)

R ^L11 and R ^L12 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. ..

The compound represented by the general formula (L-1) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The lower limit of the preferred content of the compound represented by formula (L-1) is 1%, 2%, 3%, or 5% with respect to the total amount of the liquid crystal composition. 7%, 10%, 15%, 20%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%. Further, the upper limit of the preferable content of the compound represented by the general formula (L-1) is 95%, 90%, 85%, and 80% with respect to the total amount of the liquid crystal composition. Yes, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30% Yes, 25%.

When a composition that keeps the viscosity of the liquid crystal composition low and has a fast response speed is required, it is preferable that the content of the compound represented by the general formula (L-1) has a high lower limit and a high upper limit. When a composition having a high Tni and high temperature stability is required for the liquid crystal composition, the lower limit of the content of the compound represented by formula (L-1) is moderate and the upper limit thereof is moderate. Is preferred. When it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, the lower limit and the upper limit of the content of the compound represented by the general formula (L-1) are preferably low.

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

(In the formula, R ^L12 has the same meaning as in the general formula (L-1).)

The compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.1) to the formula (L-1-1.3). Is preferably a compound represented by the formula (L-1-1.2) and/or the formula (L-1-1.3), and particularly preferably a compound represented by the formula (L-1-1.3) It is preferably a compound represented.

The lower limit of the preferred content of the compound represented by formula (L-1-1.3) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, and 5%. , 7%, and 10%. The preferred upper limit of the content is 20%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the liquid crystal composition. Yes, 5%, 3%.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-2).

(In the formula, R ^L12 has the same meaning as in the general formula (L-1).)

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

The compound represented by the general formula (L-1-2) is a compound selected from the group of compounds represented by the formula (L-1-2.1) to the formula (L-1-2.4). Are preferred, and compounds represented by formula (L-1-2.2) to formula (L-1-2.4) are preferred. In particular, the compound represented by the formula (L-1-2.2) is preferable because it improves the response speed of the liquid crystal composition. Further, when obtaining a Tni higher than the response speed, it is preferable to use the compound represented by the formula (L-1-2.3) and/or the formula (L-1-2.4). The content of the compound represented by the formula (L-1-2.3) or the formula (L-1-2.4) is not preferably 30% or more in order to improve the solubility at low temperature.

The lower limit of the preferred content of the compound represented by formula (L-1-2.2) with respect to the total amount of the liquid crystal composition is 10%, 15%, 18%, and 20%. , 23%, 25%, 27%, 30%, 33%, 35%, 38%, 40%. The preferable upper limit of the content is 60%, 55%, 50%, 45%, 43%, 40%, 38% with respect to the total amount of the liquid crystal composition. Yes, 35%, 32%, 30%, 27%, 25%, 22%.

The lower limit of the preferred total content of the compound represented by formula (L-1-1.3) and the compound represented by formula (L-1-2.2) is based on the total amount of the liquid crystal composition. 10%, 15%, 20%, 25%, 27%, 30%, 35%, 40%. The preferable upper limit of the content is 60%, 55%, 50%, 45%, 43%, 40%, 38% with respect to the total amount of the liquid crystal composition. Yes, 35%, 32%, 30%, 27%, 25%, 22%.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-3).

(In the formula, R ^L13 and R ^L14 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)

R ^L13 and R ^L14 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear alkenyl group having 2 to 5 carbon atoms. ..

The lower limit of the preferred content of the compound represented by formula (L-1-3) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 13%. , 15%, 17%, 20%, 23%, 25%, 30%. The preferable upper limit of the content is 60%, 55%, 50%, 45%, 40%, 37%, 35% with respect to the total amount of the liquid crystal composition. Yes, 33%, 30%, 27%, 27%, 25%, 23%, 20%, 17%, 15%, 13%, 10% is there.

The compound represented by the general formula (L-1-3) is a compound selected from the compound group represented by the formulas (L-1-3.1) to (L-1-3.13). Is preferably a compound represented by the formula (L-1-3.1), the formula (L-1-3.3) and/or the formula (L-1-3.4), It is preferably a compound represented by L-1-3.1) and/or a formula (L-1-3.3). In particular, the compound represented by the formula (L-1-3.1) is preferable because it improves the response speed of the liquid crystal composition. Further, when obtaining Tni higher than the response speed, the formula (L-1-3.3), the formula (L-1-3.4), the formula (L-1-3.11) and the formula (L- It is preferable to use the compound represented by 1-3.12). The total of the compounds represented by the formula (L-1-3.3), the formula (L-1-3.4), the formula (L-1-3.11) and the formula (L-1-3.13) The content of is not preferably 20% or more in order to improve the solubility at low temperature.

The lower limit of the preferred content of the compound represented by formula (L-1-3.1) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, and 5%. , 7%, 10%, 13%, 15%, 18%, 20%. The preferable upper limit of the content is 20%, 17%, 15%, 13%, 10%, 8%, 7% with respect to the total amount of the liquid crystal composition. Yes, 6%.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-4) and/or (L-1-5).

(In the formula, R ^L15 and R ^L16 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)

R ^L15 and R ^L16 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. ..

The lower limit of the preferred content of the compound represented by formula (L-1-4) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 13%. , 15%, 17% and 20%. The preferable upper limit of the content is 25%, 23%, 20%, 17%, 15%, 13%, 10% with respect to the total amount of the liquid crystal composition. is there.

The lower limit of the preferred content of the compound represented by formula (L-1-5) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 13%. , 15%, 17% and 20%. The preferable upper limit of the content is 25%, 23%, 20%, 17%, 15%, 13%, 10% with respect to the total amount of the liquid crystal composition. is there.

The compounds represented by the general formulas (L-1-4) and (L-1-5) are the compounds represented by the formulas (L-1-4.1) to (L-1-5.3). A compound selected from the group is preferable, and a compound represented by the formula (L-1-4.2) and/or the formula (L-1-5.2) is preferable.

The lower limit of the preferred content of the compound represented by formula (L-1-4.2) is 1%, 2%, 3%, and 5% with respect to the total amount of the liquid crystal composition. , 7%, 10%, 13%, 15%, 18%, 20%. The preferable upper limit of the content is 20%, 17%, 15%, 13%, 10%, 8%, 7% with respect to the total amount of the liquid crystal composition. Yes, 6%.

Formula (L-1-1.3), Formula (L-1-2.2), Formula (L-1-3.1), Formula (L-1-3.3), Formula (L-1- It is preferable to combine two or more compounds selected from the compounds represented by formula (3.4), formula (L-1-3.11) and formula (L-1-3.12), and formula (L-1 -1.3), formula (L-1-2.2), formula (L-1-3.1), formula (L-1-3.3), formula (L-1-3.4) and It is preferable to combine two or more compounds selected from the compounds represented by formula (L-1-4.2). The preferred lower limit of the total content of these compounds is 1%, 2%, 3%, 5%, 7% with respect to the total amount of the liquid crystal composition. 10%, 13%, 15%, 18%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, and the upper limit value is 80%, 70%, 60%, 50%, 45%, 40%, 37% with respect to the total amount of the liquid crystal composition. , 35%, 33%, 30%, 28%, 25%, 23%, 20%.

Further, when the reliability of the composition is emphasized, it is represented by the formula (L-1-3.1), the formula (L-1-3.3) and the formula (L-1-3.4)). It is preferable to combine two or more compounds selected from the following compounds. When importance is attached to the response speed of the composition, the formula (L-1-1.3) and the formula (L-1-2.2) are used. It is preferable to combine two or more compounds selected from the compounds shown.

The compound represented by formula (L-1) is preferably a compound selected from the group of compounds represented by formula (L-1-6).

(In the formula, R ^L17 and R ^L18 each independently represent a methyl group or a hydrogen atom.)

The lower limit of the preferred content of the compound represented by formula (L-1-6) based on the total amount of the liquid crystal composition is 1%, 5%, 10%, and 15%. , 17%, 20%, 23%, 25%, 27%, 30%, 35%. The preferable upper limit of the content is 60%, 55%, 50%, 45%, 42%, 40%, 38% with respect to the total amount of the liquid crystal composition. Yes, 35%, 33%, 30%.

The compound represented by the general formula (L-1-6) is a compound selected from the compound group represented by the formulas (L-1-6.1) to (L-1-6.3). Is preferred.

The compound represented by the general formula (L-2) is the following compound.

(In the formula, R ^L21 and R ^L22 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)

R ^L21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ^L22 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a carbon atom. Alkoxy groups of the numbers 1 to 4 are preferred.

The compound represented by the general formula (L-2) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

Regarding the content of the compound represented by the general formula (L-2), when the solubility at low temperature is important, the effect is high when the content is set high, and conversely, when the response speed is important. The effect is high when the content is set low. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The lower limit of the preferred content of the compound represented by formula (L-2) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 % And 10%. The preferred upper limit of the content is 20%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the liquid crystal composition. Yes, 5%, 3%.

The compound represented by formula (L-2) is preferably a compound selected from the group of compounds represented by formula (L-2.1) to formula (L-2.6), Compounds represented by -2.1), formula (L-2.3), formula (L-2.4) and formula (L-2.6) are preferred.

The compound represented by the general formula (L-3) is the following compound.

(In the formula, R ^L31 and R ^L32 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)

R ^L31 and R ^L32 are preferably each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

The compound represented by the general formula (L-3) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The lower limit of the preferred content of the compound represented by formula (L-3) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 % And 10%. The preferred upper limit of the content is 20%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the liquid crystal composition. Yes, 5%, 3%.

Regarding the content of the compound represented by the general formula (L-3), when a high birefringence is to be obtained, it is highly effective to set the content higher. On the contrary, when a high Tni is important, The effect is high when the content is set low. Further, in the case of improving the dripping mark and the burn-in property, it is preferable to set the content range to the middle.

The compound represented by formula (L-3) is preferably a compound selected from the group of compounds represented by formula (L-3.1) to formula (L-3.7), It is preferably a compound represented by the formula (L-3.5) from -3.2).

The compound represented by the general formula (L-4) is the following compound.

(In the formula, R ^L41 and R ^L42 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)

R ^L41 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ^L42 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a carbon atom Alkoxy groups of the numbers 1 to 4 are preferred. )

The compound represented by the general formula (L-4) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

In the liquid crystal composition, the content of the compound represented by the general formula (L-4) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the dripping mark, the seizure, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.

The lower limit of the preferred content of the compound represented by formula (L-4) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 %, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%. The upper limit of the preferred content of the compound represented by formula (L-4) based on the total amount of the liquid crystal composition is 50%, 40%, 35%, 30%, 20 %, 15%, 10%, 5%.

The compound represented by the general formula (L-4) is preferably, for example, a compound represented by the formula (L-4.1) to the formula (L-4.3).

The liquid crystal composition contains the compound represented by the formula (L-4.1) according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. Or may contain a compound represented by the formula (L-4.2), represented by a compound represented by the formula (L-4.1) and a compound represented by the formula (L-4.2). It may contain both the compound and the compound represented by the formula (L-4.1) to the formula (L-4.3). The lower limit of the preferred content of the compound represented by formula (L-4.1) or formula (L-4.2) is 3% or 5%, based on the total amount of the liquid crystal composition. 7%, 9%, 11%, 12%, 12%, 13%, 18%, 21%, preferred upper limit values are 45, 40%, 35 %, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%.

When both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, both compounds are preferably contained in the total amount of the liquid crystal composition. The lower limit of the amount is 15%, 19%, 24%, 30%, and the preferred upper limit is 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (L-4) is preferably, for example, a compound represented by the formula (L-4.4) to the formula (L-4.6), and the compound represented by the formula (L-4.4): It is preferable that it is a compound represented by these.

The liquid crystal composition contains the compound represented by the formula (L-4.4) according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. Also contains a compound represented by the formula (L-4.5), a compound represented by the formula (L-4.4) and a compound represented by the formula (L-4.5) Both may be included.

The lower limit of the preferred content of the compound represented by formula (L-4.4) or formula (L-4.5) is 3% or 5%, based on the total amount of the liquid crystal composition. 7%, 9%, 11%, 12%, 13%, 18%, 21%. Preferred upper limits are 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13 %, 10%, 8%.

When both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) are contained, the both compounds are preferably contained in the total amount of the liquid crystal composition. The lower limit of the amount is 15%, 19%, 24%, 30%, and the preferred upper limit is 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (L-4) is preferably a compound represented by the formula (L-4.7) to the formula (L-4.10), and particularly, the compound represented by the formula (L-4. The compound represented by 9) is preferable.

The compound represented by the general formula (L-5) is the following compound.

(In the formula, R ^L51 and R ^L52 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)

R ^L51 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ^L52 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or a carbon atom Alkoxy groups of the numbers 1 to 4 are preferred.

The compound represented by the general formula (L-5) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

In the liquid crystal composition, the content of the compound represented by the general formula (L-5) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the dripping mark, the seizure, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.

The lower limit of the preferred content of the compound represented by formula (L-5) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 %, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%. The upper limit of the preferred content of the compound represented by formula (L-5) based on the total amount of the liquid crystal composition is 50%, 40%, 35%, 30%, 20 %, 15%, 10%, 5%

The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) and/or the formula (L-5.2), and particularly, the compound represented by the formula (L- It is preferably a compound represented by 5.1). The lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, and 7%. The upper limits of the preferred contents of these compounds are 20%, 15%, 13%, 10% and 9%.

The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) and/or the formula (L-5.4). The lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, and 7%. The upper limits of the preferred contents of these compounds are 20%, 15%, 13%, 10% and 9%.

The compound represented by the general formula (L-5) is preferably a compound selected from the group of compounds represented by the formulas (L-5.5) to (L-5.7), and particularly preferably the compound represented by the formula (L-5.5) It is preferably a compound represented by L-5.7). The lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, and 7%. The upper limits of the preferred contents of these compounds are 20%, 15%, 13%, 10% and 9%.

The compound represented by the general formula (L-6) is the following compound.

(In the formula, R ^L61 and R ^L62 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L), and X ^L61 and X ^L62 each independently represent a hydrogen atom or a fluorine atom. )

R ^L61 and R ^L62 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and one of X ^L61 and X ^L62 is a fluorine atom and the other is a hydrogen atom. Preferably.

The compound represented by the general formula (L-6) can be used alone, or two or more compounds can be used in combination. The kinds of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, one type, two types, three types, four types, and five or more types in one embodiment of the present invention.

The lower limit of the preferred content of the compound represented by formula (L-6) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 %, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%. The upper limit of the preferred content of the compound represented by formula (L-6) based on the total amount of the liquid crystal composition is 50%, 40%, 35%, 30%, 20 %, 15%, 10%, 5%. When focusing on increasing Δn, it is preferable to increase the content, and when focusing on precipitation at low temperature, the content is preferably low.

The compound represented by the general formula (L-6) is preferably a compound represented by the formula (L-6.1) to the formula (L-6.9).

The types of compounds that can be combined are not particularly limited, but it is preferable to contain 1 to 3 types of these compounds, and more preferably 1 to 4 types. Further, the fact that the selected compound has a wide molecular weight distribution is also effective for solubility. Therefore, for example, one kind of the compounds represented by the formulas (L-6.1) and (L-6.2) or the formula (L- 6.4) and (L-6.5), one type, compounds represented by formula (L-6.6) and (L-6.7), one type, formula (L It is preferable to select one kind of compound from the compounds represented by -6.8) and (L-6.9) and to combine these appropriately. Among them, it is represented by formula (L-6.1), formula (L-6.3), formula (L-6.4), formula (L-6.6) and formula (L-6.9). It is preferable to include a compound.

The compound represented by the general formula (L-6) is preferably, for example, a compound represented by the formula (L-6.10) to the formula (L-6.17), and among them, the compound represented by the formula (L- The compound represented by 6.11) is preferable.

The lower limit of the preferable content of these compounds with respect to the total amount of the liquid crystal composition is 1%, 2%, 3%, 5% and 7%. The upper limits of the preferred contents of these compounds are 20%, 15%, 13%, 10% and 9%.

The compound represented by the general formula (L-7) is the following compound.

(In the formula, R ^L71 and R ^L72 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L), and A ^L71 and A ^L72 are each independently A ^L2 in the general formula (L) and It has the same meaning as A ^L3 , but the hydrogen atoms on A ^L71 and A ^L72 may each independently be replaced by a fluorine atom, and Z ^L71 has the same meaning as Z ^L2 in formula (L), (X ^L71 and X ^L72 each independently represent a fluorine atom or a hydrogen atom.)

In the formula, R ^L71 and R ^L72 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and A ^L71 and A ^L72 Are each independently preferably a 1,4-cyclohexylene group or a 1,4-phenylene group, hydrogen atoms on A ^L71 and A ^L72 may be each independently substituted by a fluorine atom, and Z ^L71 is a single group. A bond or COO- is preferred, a single bond is preferred, and X ^L71 and X ^L72 are preferably hydrogen atoms.

There are no particular restrictions on the types of compounds that can be combined, but they are combined according to the required performance such as low temperature solubility, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, two types, three types, and four types in one embodiment of the present invention.

In the liquid crystal composition, the content of the compound represented by the general formula (L-7) is such that the solubility at low temperature, the transition temperature, the electrical reliability, the birefringence, the process compatibility, the dripping mark, the burn-in, It is necessary to appropriately adjust according to the required performance such as dielectric anisotropy.

The lower limit of the preferred content of the compound represented by formula (L-7) based on the total amount of the liquid crystal composition is 1%, 2%, 3%, 5%, 7 %, 10%, 14%, 16%, 20%. The upper limit of the preferred amount of the compound represented by formula (L-7) based on the total amount of the liquid crystal composition is 30%, 25%, 23%, 20%, 18 %, 15%, 10%, 5%.

The liquid crystal composition preferably contains a large amount of the compound represented by the formula (L-7) when an embodiment having a high Tni is desired, and when an embodiment having a low viscosity is desired, the content thereof is preferably increased. It is preferable to use a small amount.

The compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.1) to the formula (L-7.4), and the compound represented by the formula (L-7.2) The compound represented by is preferable.

The compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.11) to the formula (L-7.13), and the compound represented by the formula (L-7.11) The compound represented by is preferable.

The compound represented by the general formula (L-7) is a compound represented by the formula (L-7.21) to the formula (L-7.23). It is preferably a compound represented by the formula (L-7.21).

The compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.31) to the formula (L-7.34), and a compound represented by the formula (L-7.31) And/or a compound represented by the formula (L-7.32) are preferred.

The compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.41) to the formula (L-7.44), and a compound represented by the formula (L-7.41) And/or a compound represented by the formula (L-7.42) is preferable.

The compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.51) to the formula (L-7.53).

(Other compounds)
The polymerizable compound-containing liquid crystal composition of the present invention may contain a polymerization initiator in order to promote the polymerization, although the polymerization proceeds even when the polymerization initiator is not present. Examples of the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides and the like.

The polymerizable compound-containing liquid crystal composition of the present invention contains the polymerizable compound represented by the general formula (i), but other polymerizable compounds may be used in combination. Examples of the other polymerizable compound include compounds represented by the following general formula (P).

(In the general formula (P), R ^p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or —Sp ^p2 —P ^p2 , and one of the alkyl group or non- Two or more adjacent —CH ₂ — may be independently substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—, One or two or more hydrogen atoms in the alkyl group may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
P ^p1 and P ^p2 are each independently a general formula (P ^p1 -1) to a formula (P ^p1 -9)

(In the formula, R ^p11 and R ^p12 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms, W ^p11 is a single bond, —O Represents a —, —COO— or methylene group, and t ^p11 represents 0, 1 or 2, but when a plurality of R ^p11 , R ^p12 , W ^p11 and/or t ^p11 are present in the molecule, they are the same. It may be either different or different.)
Sp ^p1 and Sp ^p2 each independently represent a single bond or a spacer group,
Z ^p1 and Z ^p2 are each independently a single bond, —O—, —S—, —CH ₂ —, —OCH ₂ —, —CH ₂ O—, —CO—, —C ₂ H ₄ —, — _{COO -, - OCO -, -} OCOOCH 2 -, - CH 2 OCOO -, - OCH 2 CH 2 O -, - CO-NR ZP1 -, - NR ZP1 -CO -, - SCH 2 -, - CH 2 S- ^{, -CH = CR ZP1 -COO -,} - CH = CR ZP1 -OCO -, - COO-CR ZP1 = CH -, - OCO-CR ZP1 = CH -, - COO-CR ZP1 = CH-COO -, - COO -CR ^ZP1 =CH- ^{OCO-, -OCO} -CR ^ZP1 =CH- ^{COO-, -OCO} -CR ^ZP1 =CH- ^OCO- , -(CH ₂ ) _z -COO-, -(CH ₂ ) ₂ -OCO- , -OCO-(CH ₂ ) ₂ -, -(C=O)-O-(CH ₂ ) ₂ -, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-. _{, -CF 2 -, - CF 2} O -, - OCF 2 -, - CF 2 CH 2 -, - CH 2 CF 2 -, - CF 2 CF 2 - or -C≡C- ^{(wherein, R ZP1} is Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, but when a plurality of R ^ZP1's are present in the molecule, they may be the same or different).
A ^p1 , A ^p2 and A ^p3 are each independently
^(A p) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B ^p ) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced with —N═) and (c). ^p ) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, phenanthrene-2,7-diyl group or anthracene Selected from the group consisting of -2,6-diyl groups (one -CH= present in these groups or two or more -CH= not adjacent to each other may be replaced by -N=). represents a group, the above groups (a ^p), 1 or 2 or more hydrogen atoms present in the radical (b ^p) and group (c ^p) are each independently a halogen atom, a cyano group, a carbon atom It may be substituted with an alkyl group of the formulas 1 to 8 or —Sp ^p2 —P ^p2 , and one or two or more non-adjacent —CH ₂ — in the alkyl group are independently —CH═CH. -, -C≡C-, -O-, -CO-, -COO- or -OCO- may be substituted,
m ^p1 represents 0, 1, 2 or 3, and when a plurality of Z ^p1 , A ^p2 , Sp ^p2 and/or P ^p2 are present in the molecule, they may be the same or different, A ^p3 represents a single bond when m ^p1 is 0 and A ^p1 is a phenanthrene-2,7-diyl group or anthracene-2,6-diyl group. However, the compound represented by the general formula (i) is excluded. )

The compound represented by the general formula (P) is preferably contained in one kind or two or more kinds.

In the general formula (P), R ^p1 is preferably —Sp ^p2 —P ^p2 .

P ^p1 and P ^p2 each independently represent one of formulas (P ^p1 -1) to (P ^p1 -3), and preferably (P ^p1 -1).

R ^p11 and R ^p12 are preferably each independently a hydrogen atom or a methyl group.

0 or 1 is preferable for ^tp11 .

W ^p11 is preferably a single bond, a methylene group or an ethylene group.

m ^p1 is preferably 0, 1 or 2, and preferably 0 or 1.

Z ^p1 and Z ^p2 are each independently a single bond, —OCH ₂ —, —CH ₂ O—, —CO—, —C ₂ H ₄ —, —COO—, —OCO—, —COOC ₂ H ₄ —. _{, -OCOC 2 H 4 -, -} C 2 H 4 OCO -, - C 2 H 4 COO -, - CH = CH -, - CF 2 -, - CF 2 O -, - (CH 2) 2 -COO- , -(CH ₂ ) ₂ -OCO-, -OCO-(CH ₂ ) ₂ -, -CH=CH-COO-, -COO-CH=CH-, -OCOCH=CH-, -COO-(CH ₂ ) ₂ −, —OCF ₂ — or —C≡C— is preferable, and a single bond, —OCH ₂ —, —CH ₂ O—, —C ₂ H ₄ —, —COO—, —OCO—, —COOC ₂ H _{4 is used.} -, -OCOC ₂ H ₄ -, -C ₂ H ₄ OCO-, -C ₂ H ₄ COO-, -CH=CH-, -(CH ₂ ) ₂ -COO-, -(CH ₂ ) ₂ -OCO- , -OCO-(CH ₂ ) ₂ -, -CH=CH-COO-, -COO-CH=CH-, -OCOCH=CH-, -COO-(CH ₂ ) ₂ -or -C≡C- is preferable. , only one -OCH ₂ present in the molecule _{-, - CH 2 O -,} - C 2 H 4 -, - COO -, - OCO -, - COOC 2 H 4 -, - OCOC 2 H 4 -, _{-C 2 H 4 OCO -, -} C 2 H 4 COO -, - CH = CH -, - (CH 2) 2 -COO -, - (CH 2) 2 -OCO -, - OCO- (CH 2) 2 -, -CH=CH-COO-, -COO-CH=CH-, -OCOCH=CH-, -COO-(CH ₂ ) ₂ -or -C≡C- and all others are single bonds. Is preferred, only one of which is present in the molecule is —OCH ₂ —, —CH ₂ O—, —C ₂ H ₄ —, —COO— or —OCO—, and the others are all single bonds. It is preferable that all are single bonds.

Further, only one of Z ^p1 and Z ^p2 existing in the molecule is —CH═CH—COO—, —COO—CH═CH—, —(CH ₂ ) ₂ —COO—, —(CH ₂ ) ₂ It is preferably a linking group selected from the group consisting of —OCO—, —O—CO—(CH ₂ ) ₂ —, and —COO—(CH ₂ ) ₂ —, and the others are preferably single bonds.

Sp ^p1 and Sp ^p2 each independently represent a single bond or a spacer group, and the spacer group is preferably an alkylene group having 1 to 30 carbon atoms, and —CH ₂ — in the alkylene group has a plurality of oxygen atoms. Unless directly linked, they may be substituted with -O-, -CO-, -COO-, -OCO-, -CH=CH- or -C≡C-, and the hydrogen atom in the alkylene group is a halogen atom. May be substituted with, but a linear alkylene group having 1 to 10 carbon atoms or a single bond is preferable.
A ^p1 , A ^p2 and A ^p3 are each independently preferably a 1,4-phenylene group or a 1,4-cyclohexylene group, more preferably a 1,4-phenylene group. The 1,4-phenylene group is preferably substituted with one fluorine atom, one methyl group or one methoxy group in order to improve the compatibility with the liquid crystal compound.

The total content of the compounds represented by the general formula (P) is 0.05 to 10 with respect to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention containing the compound represented by the general formula (P). %, preferably 0.1 to 8%, more preferably 0.1 to 5%, and 0.1 to 3%. It is preferably in the range of 0.2 to 2%, preferably in the range of 0.2 to 1.3%, and in the range of 0.2 to 1%. It is preferably in the range of 0.2 to 0.56%.

The preferable lower limit of the total content of the compounds represented by the general formula (P) is 0 with respect to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention containing the compound represented by the general formula (P). 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0. 25% and 0.3%.

The preferable upper limit of the total content of the compounds represented by the general formula (P) is 10 with respect to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention containing the compound represented by the general formula (P). %, 8%, 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, 0.5% is there.

When the content of the compound represented by the general formula (P) contained in the polymerizable compound-containing liquid crystal composition of the present invention is small, the effect of adding the compound represented by the general formula (P) is difficult to appear and the liquid crystal composition However, if the above content is too large, the amount remaining after curing will increase, the curing will take time, and the reliability of the liquid crystal will increase. And other problems occur. Therefore, the content is set in consideration of these balances.

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

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

Preferred examples of the compound represented by the general formula (P) include polymerizable compounds represented by the following formulas (P-2-1) to (P-2-9).

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

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

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

Preferred examples of the compound represented by the general formula (P) include polymerizable compounds represented by the following formulas (P-4-1) to (P-4-19).

(In the formula, P ^p41 , P ^p42 , Sp ^p41, and Sp ^p42 have the same meanings as P ^p1 , P ^p2 , Sp ^p1, and Sp ^{p2 in} the general formula (P-4).)

When the polymerizable compound-containing liquid crystal composition of the present invention contains the compound represented by the general formula (P), the total content of the compound represented by the general formula (i) and the compound represented by the general formula (P) is contained. The amount is preferably in the range of 0.05 to 10%, preferably 0.1 to 8%, and 0.1 to the total amount of the polymerizable compound-containing liquid crystal composition. Is preferably in the range of 5% to 5%, more preferably in the range of 0.1% to 3%, preferably in the range of 0.2% to 2%, and 0.2% to 1.3%. Is preferably in the range of 0.2 to 1%, more preferably 0.2 to 0.56%.

When the polymerizable compound-containing liquid crystal composition of the present invention contains the compound represented by the general formula (P), the total content of the compound represented by the general formula (i) and the compound represented by the general formula (P) is contained. The preferred lower limit of the amount is 0.01%, 0.03%, 0.05%, 0.08%, and 0.1% with respect to the polymerizable compound-containing liquid crystal composition. %, 0.15%, 0.2%, 0.25%, 0.3%.

When the polymerizable compound-containing liquid crystal composition of the present invention contains the compound represented by the general formula (P), the total content of the compound represented by the general formula (i) and the compound represented by the general formula (P) is contained. The preferable upper limit of the amount is 10%, 8%, 5%, 3%, 1.5%, 1.2% with respect to the polymerizable compound-containing liquid crystal composition. , 1%, 0.8%, 0.5%.

The polymerizable compound-containing liquid crystal composition of the present invention may further contain a compound represented by the general formula (Q).

(In the formula, R ^Q represents a straight chain alkyl group or a branched chain alkyl group having 1 to 22 carbon atoms, and one or more CH ₂ groups in the alkyl group are such that oxygen atoms are not directly adjacent to each other. May be substituted with —O—, —CH═CH—, —CO—, —OCO—, —COO—, —C≡C—, —CF ₂ O—, —OCF ₂ —, and M ^Q is trans. Represents a 1,4-cyclohexylene group, a 1,4-phenylene group or a single bond.)

In the above general formula (Q), R ^Q represents a straight chain alkyl group or a branched chain alkyl group having 1 to 22 carbon atoms, and one or more CH ₂ groups in the alkyl group have an oxygen atom. It may be substituted with -O-, -CH=CH-, -CO-, -OCO-, -COO-, -C≡C-, -CF ₂ O-, -OCF _2- so as not to be directly adjacent to each other. A linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group, a linear alkyl group in which one CH ₂ group is replaced with —OCO— or —COO—, a branched alkyl group, a branched alkoxy group, 1 A branched chain alkyl group in which one CH ₂ group is replaced by —OCO— or —COO— is preferable, a straight chain alkyl group having 1 to 20 carbon atoms, and one CH ₂ group is replaced by —OCO— or —COO— A straight chain alkyl group, a branched chain alkyl group, a branched alkoxy group, and a branched chain alkyl group in which one CH ₂ group is replaced with —OCO— or —COO— are more preferable.

In the general formula (Q), M ^Q represents a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a single bond, but a trans-1,4-cyclohexylene group or a 1,4-cyclohexylene group. A phenylene group is preferred.

More specifically, the compound represented by the general formula (Q) is preferably a compound represented by the following general formula (Qa) to general formula (Qd).

In the formula, R ^Q1 is preferably a straight chain alkyl group or a branched chain alkyl group having 1 to 10 carbon atoms, R ^Q2 is preferably a straight chain alkyl group or a branched chain alkyl group having 1 to 20 carbon atoms, and R ^Q3 is A linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group, a linear alkoxy group or a branched alkoxy group is preferable, and L ^Q is preferably a linear alkylene group having 1 to 8 carbon atoms or a branched alkylene group. ..

The compound represented by the general formula (Q) is a compound represented by the general formula (Qc) and the general formula (Qd) among the compounds represented by the general formula (Qa) to the general formula (Qd). More preferably, it is the compound represented.

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains one or more compounds represented by formula (Q), and more preferably one to five compounds. In this case, the content of the compound represented by the general formula (Q) relative to the total amount of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 0.001 to 1%, and 0.001 to 0.1%. % Is more preferable, and 0.001 to 0.05% is particularly preferable.

The polymerizable compound-containing liquid crystal composition of the present invention may contain a usual nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal, an antioxidant, an ultraviolet absorber, a light stabilizer or an infrared absorber in addition to the above compounds. good.

Specific examples of the antioxidants and light stabilizers that can be used in the present invention include compounds represented by the following formulas (III-1) to (III-40).

(In the above formulas (III-1) to (III-40), n represents an integer of 0 to 20.)

The polymerizable compound-containing liquid crystal composition of the present invention contains one or more compounds represented by the general formula (Q) or compounds selected from the general formulas (III-1) to (III-40). It is more preferable to contain 1 to 5 types, and the content is preferably 0.001 to 1%, more preferably 0.001 to 0.1%, and 0.001 to 0.05. % Is particularly preferred.

(Other)
The dielectric constant anisotropy (Δε) of the polymerizable compound-containing liquid crystal composition of the present invention at 20° C. is preferably −2.0 to −8.0, more preferably −2.0 to −5.0, 2.5 to -5.0 is particularly preferred.

The refractive index anisotropy (Δn) at 20° C. of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 0.08 to 0.14, more preferably 0.09 to 0.13, and 0.09 to 0. .12 is particularly preferred. More specifically, it is preferably 0.10 to 0.13 when it corresponds to a thin cell gap and 0.08 to 0.10 when it corresponds to a thick cell gap.

The viscosity (η) at 20° C. of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 10 to 50 mPa·s, preferably 10 to 40 mPa·s, and 10 to 35 mPa·s. Is preferable, 10 to 30 mPa·s is preferable, 10 to 25 mPa·s is more preferable, and 10 to 22 mPa·s is particularly preferable.

The rotational viscosity (γ ₁ ) at 20° C. of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 50 to 160 mPa·s, preferably 60 to 160 mPa·s, and 60 to 150 mPa·s. Is preferably 60 to 140 mPa·s, preferably 60 to 130 mPa·s, more preferably 60 to 125 mPa·s, and even more preferably 60 to 120 mPa·s, It is more preferably 60 to 115 mPa·s, more preferably 60 to 110 mPa·s, and particularly preferably 60 to 100 mPa·s.

The nematic phase-isotropic liquid phase transition temperature (Tni) of the polymerizable compound-containing liquid crystal composition of the present invention is preferably 60° C. to 120° C., more preferably 70° C. to 100° C., and particularly 70° C. to 85° C. preferable.

In the whole polymerizable compound-containing liquid crystal composition of the present invention, the compound represented by the general formula (i), the general formula (N-1), the general formula (N-2), the general formula (N-3) and the general formula (L) The upper limit of the proportion occupied by the components composed only of the represented compounds is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass, 94% by mass, 93% by mass, It is preferably 92% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, and 84% by mass.

Further, in the whole polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1), general formula (N-2), general formula (N-3) and general formula (L ), the lower limit of the proportion of the components composed only of the compound is 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass% %, 89 mass %, 90 mass %, 91 mass %, 92 mass %, 93 mass %, 94 mass %, 95 mass %, 96 mass %, 97 mass %, 98 mass %, 99 mass %. ..

Of the entire polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1a), general formula (N-1b), general formula (N-1c), and general formula (N-1d) ), general formulas (N-1e) and compounds represented by general formula (L), the upper limit of the proportion of the components composed of only the compounds is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96 mass %, 95 mass %, 94 mass %, 93 mass %, 92 mass %, 91 mass %, 90 mass %, 89 mass %, 88 mass %, 87 mass %, 86 mass %, 85 mass %, 84 mass % Is preferable.

Further, in the whole polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1a), general formula (N-1b), general formula (N-1c), and general formula (N -1d), general formulas (N-1e) and compounds represented by general formula (L), the lower limit of the proportion of the components composed of only the compounds is 78% by mass, 80% by mass, 81% by mass, 83% by mass. %, 85 mass %, 86 mass %, 87 mass %, 88 mass %, 89 mass %, 90 mass %, 91 mass %, 92 mass %, 93 mass %, 94 mass %, 95 mass %, 96 mass %, It is preferably 97% by mass, 98% by mass, and 99% by mass.

Of the entire polymerizable compound-containing liquid crystal composition of the present invention, it is composed of only the compounds represented by the general formula (i), the general formula (N-1c), the general formula (N-1d), and the general formula (L). The lower limit value of the proportion occupied by the components is 50 mass %, 61 mass %, 63 mass %, 65 mass %, 66 mass %, 67 mass %, 68 mass %, 70 mass %, 71 mass %, 73 mass %. , 75 mass%, 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 It is preferably mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, and 99 mass%.

Further, of the entire polymerizable compound-containing liquid crystal composition of the present invention, only the compounds represented by the general formula (i), the general formula (N-1c), the general formula (N-1d), and the general formula (L) The upper limit of the proportion occupied by the components consisting of 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 It is preferably mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, and 84 mass%.

Of the entire polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1-4), general formula (N-1b), general formula (N-1c), and general formula (N -1d), general formulas (N-1e) and compounds represented by general formula (L), the upper limits of the proportions of the components composed only of the compounds are 100% by mass, 99% by mass, 98% by mass and 97% by mass. %, 96 mass %, 95 mass %, 94 mass %, 93 mass %, 92 mass %, 91 mass %, 90 mass %, 89 mass %, 88 mass %, 87 mass %, 86 mass %, 85 mass %, It is preferably 84% by mass.

Further, in the whole liquid crystal composition containing a polymerizable compound of the present invention, the general formula (i), the general formula (N-1-4), the general formula (N-1b), the general formula (N-1c), the general formula The lower limit values of the proportions of the components composed only of the compounds represented by (N-1d), the general formula (N-1e) and the general formula (L) are 78% by mass, 80% by mass, 81% by mass, 83% by mass, 85% by mass, 86% by mass, 87% by mass, 88% by mass, 89% by mass, 90% by mass, 91% by mass, 92% by mass, 93% by mass, 94% by mass, 95% by mass, 96% by mass %, 97% by mass, 98% by mass, and 99% by mass are preferable.

Of the entire polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1a), general formula (N-1b), general formula (N-1c), and general formula (N-1d) ), general formula (N-1e), general formula (L-1), general formula (L-3), general formula (L-4), general formula (L-5) and general formula (L-6). The upper limit of the proportion occupied by the components composed only of the represented compounds is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass, 94% by mass, 93% by mass, 92 mass %, 91 mass %, 90 mass %, 89 mass %, 88 mass %, 87 mass %, 86 mass %, 85 mass %, 84 mass %, 83 mass %, 82 mass %, 81 mass %, 80 mass % Is preferable.

Further, in the whole polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1a), general formula (N-1b), general formula (N-1c), and general formula (N -1d), general formula (N-1e) and general formula (L-1), general formula (L-3), general formula (L-4), general formula (L-5) and general formula (L-6) ), the lower limit of the proportion occupied by the component composed only of the compound is 68 mass%, 70 mass%, 71 mass%, 73 mass%, 75 mass%, 78 mass%, 80 mass%, 81 mass% %, 83 mass %, 85 mass %, 86 mass %, 87 mass %, 88 mass %, 89 mass %, 90 mass %, 91 mass %, 92 mass %, 93 mass %, 94 mass %, 95 mass %, It is preferably 96% by mass, 97% by mass, 98% by mass and 99% by mass.

Of the whole polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1a), general formula (L-1), general formula (L-3), and general formula (L-4 ), a general formula (L-5) and a compound represented by the general formula (L-6) alone, the upper limit of the proportion occupied by the components is 100% by mass, 99% by mass, 98% by mass, 97% by mass. %, 96 mass %, 95 mass %, 94 mass %, 93 mass %, 92 mass %, 91 mass %, 90 mass %, 89 mass %, 88 mass %, 87 mass %, 86 mass %, 85 mass %, 84 mass %, 83 mass %, 82 mass %, 81 mass %, 80 mass %, 79 mass %, 78 mass %, 77 mass %, 76 mass %, 75 mass %, 74 mass %, 73 mass %, 72 mass %. %, 71 mass %, 70 mass %, 69 mass %, 68 mass %, 67 mass %, 66 mass %, 65 mass %, 64 mass %, 63 mass %, 62 mass %.

Further, in the whole polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1a), general formula (L-1), general formula (L-3), and general formula (L -4), the lower limit of the proportion occupied by the components composed only of the compounds represented by the general formula (L-5) and the general formula (L-6) is 38% by mass, 40% by mass, 41% by mass, 43 mass%, 45 mass%, 48 mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass% %, 74 mass %, 76 mass %, 78 mass %, 80 mass %, 82 mass %, 84 mass %, 86 mass %, 88 mass %, 90 mass %, and 92 mass %.

Of the entire polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1d), general formula (L-1), general formula (L-3), and general formula (L-4 ), a general formula (L-5) and a compound represented by the general formula (L-6) alone, the upper limit of the proportion occupied by the components is 100% by mass, 99% by mass, 98% by mass, 97% by mass. %, 96 mass %, 95 mass %, 94 mass %, 93 mass %, 92 mass %, 91 mass %, 90 mass %, 89 mass %, 88 mass %, 87 mass %, 86 mass %, 85 mass %, 84 mass %, 83 mass %, 82 mass %, 81 mass %, 80 mass %, 79 mass %, 78 mass %, 77 mass %, 76 mass %, 75 mass %, 74 mass %, 73 mass %, 72 mass %. %, 71 mass %, 70 mass %, 69 mass %, 68 mass %, 67 mass %, 66 mass %, 65 mass %, 64 mass %, 63 mass %, 62 mass %.

Further, in the whole polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1d), general formula (L-1), general formula (L-3), and general formula (L -4), the lower limit of the proportion occupied by the components composed only of the compounds represented by the general formula (L-5) and the general formula (L-6) is 38% by mass, 40% by mass, 41% by mass, 43 mass%, 45 mass%, 48 mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass% %, 74 mass %, 76 mass %, 78 mass %, 80 mass %, 82 mass %, 84 mass %, 86 mass %, 88 mass %, 90 mass %, and 92 mass %.

Of the whole polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1c), general formula (N-1d), general formula (L-1), and general formula (L-3 ), and the lower limit of the proportion occupied by the component composed only of the compound represented by the general formula (L-5) is 38% by mass, 40% by mass, 41% by mass, 43% by mass, 45% by mass, 48% by mass. Mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass%, 74 mass%, 76 mass% , 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 It is preferably mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.

Further, in the whole polymerizable compound-containing liquid crystal composition of the present invention, general formula (i), general formula (N-1c), general formula (N-1d), general formula (L-1), and general formula (L -3), and the upper limit of the proportion of the components composed only of the compound represented by the general formula (L-5) is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass. 95 mass %, 94 mass %, 93 mass %, 92 mass %, 91 mass %, 90 mass %, 89 mass %, 88 mass %, 87 mass %, 86 mass %, 85 mass %, 84 mass %, 83 mass %. % By mass, 82% by mass, 81% by mass, 80% by mass, 79% by mass, 78% by mass, 77% by mass, 76% by mass, 75% by mass, 74% by mass, 73% by mass, 72% by mass, 71% by mass , 70 mass %, 69 mass %, 68 mass %, 67 mass %, 66 mass %, 65 mass %, 64 mass %, 63 mass %, 62 mass %.

The polymerizable compound-containing liquid crystal composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms are bonded to each other such as a peracid (—CO—OO—) structure in the molecule. When the reliability and long-term stability of the liquid crystal composition are emphasized, the content of the compound having a carbonyl group contained in the polymerizable compound-containing liquid crystal composition of the present invention is the total amount of the polymerizable compound-containing liquid crystal composition. Is preferably 5% or less, more preferably 3% or less, still more preferably 1% or less, and most preferably substantially not contained.

When importance is attached to the stability by UV irradiation, in the polymerizable compound-containing liquid crystal composition of the present invention, the content of the compound substituted with a chlorine atom is 15% with respect to the total amount of the polymerizable compound-containing liquid crystal composition. It is preferably not more than 10%, preferably not more than 10%, more preferably not more than 8%, more preferably not more than 5%, preferably not more than 3%, and not substantially contained. Is more preferable.

The polymerizable compound-containing liquid crystal composition of the present invention preferably contains a large amount of a compound in which all the ring structures in the molecule are 6-membered rings. In the polymerizable compound-containing liquid crystal composition of the present invention, the content of compounds in which all ring structures in the molecule are 6-membered rings is 80% or more based on the total amount of the polymerizable compound-containing liquid crystal composition. It is preferably 90% or more, more preferably 95% or more, and the polymerizable compound-containing liquid crystal composition is a compound in which the ring structure in the molecule is substantially all 6-membered ring. Most preferably it is configured.

In order to suppress deterioration due to oxidation, the polymerizable compound-containing liquid crystal composition of the present invention preferably contains a small amount of a compound having a cyclohexenylene group as a ring structure. In the polymerizable compound-containing liquid crystal composition of the present invention, the content of the compound having a cyclohexenylene group is preferably 10% or less with respect to the total amount of the polymerizable compound-containing liquid crystal composition, and 8% or less. It is preferable that the content is 5% or less, more preferably 3% or less, and further preferably substantially not contained.

When importance is attached to the improvement of viscosity and the improvement of Tni, the polymerizable compound-containing liquid crystal composition of the present invention contains a molecule of 2-methylbenzene-1,4-diyl group in which a hydrogen atom may be substituted with halogen. It is preferable that the content of the compound contained therein is small. In the polymerizable compound-containing liquid crystal composition of the present invention, the content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is 10% or less based on the total amount of the polymerizable compound-containing liquid crystal composition. Is preferable, 8% or less is preferable, 5% or less is more preferable, 3% or less is preferable, and it is more preferable not to contain substantially.

In the present application, “substantially free from” means not including except an unintended inclusion.

II. Liquid Crystal Display Element Next, the liquid crystal display element of the present invention will be described. The liquid crystal display device of the present invention is a liquid crystal composition containing one or more polymerizable compounds represented by the general formula (i), in other words, the above-mentioned item "I. Polymerizable compound-containing liquid crystal composition". A liquid crystal display device using the polymerizable compound-containing liquid crystal composition described in 1. The liquid crystal display device using the polymerizable compound-containing liquid crystal composition of the present invention has a remarkable feature of high-speed response. In addition, a tilt angle is sufficiently obtained, and there is no unreacted polymerizable compound. Since the number is so small as not to be a problem and the voltage holding ratio (VHR) is high, there are no defects such as alignment defects and display defects, or they are sufficiently suppressed. In addition, since the tilt angle and the residual amount of the polymerizable compound can be easily controlled, it is easy to optimize and reduce the energy cost for manufacturing, which is optimal for improving production efficiency and stable mass production.

The liquid crystal display device using the polymerizable compound-containing liquid crystal composition of the present invention is particularly useful as an active matrix driving liquid crystal display device, and has a PSA mode, a PSVA mode, a VA mode, a PS-IPS mode or a PS-FFS mode. It can be used for a liquid crystal display device.

The liquid crystal display element of the present invention includes a first substrate and a second substrate which are arranged to face each other, a common electrode provided on the first substrate or the second substrate, and the first substrate or the first substrate. It is preferable to have a pixel electrode provided on the second substrate and having a thin film transistor, and a liquid crystal layer containing the polymerizable compound-containing liquid crystal composition provided between the first substrate and the second substrate. If necessary, an alignment film for controlling the alignment direction of the liquid crystal molecules may be provided on the facing surface side of at least one of the first substrate and the second substrate so as to come into contact with the liquid crystal layer. The alignment film may not be provided on both the second substrate and the second substrate. As the alignment film, a vertical alignment film, a horizontal alignment film, or the like can be appropriately selected according to the driving mode of the liquid crystal display element, and a rubbing alignment film (eg, polyimide alignment film) or a photo alignment film (eg, decomposition type). A known alignment film such as a polyimide alignment film) can be used. Further, a color filter may be appropriately provided on the first substrate or the second substrate, and a color filter can be provided on the pixel electrode or the common electrode.

The two substrates of the liquid crystal cell used in the liquid crystal display device of the present invention can be made of a transparent transparent material such as glass or plastic, and one of them may be an opaque material such as silicon. The transparent substrate having the transparent electrode layer can be obtained, for example, by sputtering indium tin oxide (ITO) on a transparent substrate such as a glass plate.

The color filter can be prepared by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like. The method for producing a color filter by the pigment dispersion method will be described as an example. A curable colored composition for a color filter is applied on the transparent substrate, subjected to patterning treatment, and cured by heating or light irradiation. By performing this step for each of the three colors of red, green, and blue, a pixel portion for a color filter can be created. In addition, a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal specific resistance element may be provided on the substrate.

The first substrate and the second substrate are preferably opposed to each other so that the common electrode and the pixel electrode layer are inside.

The distance between the first substrate and the second substrate may be adjusted via a spacer. At this time, the thickness of the obtained liquid crystal layer is preferably adjusted to 1 to 100 μm, more preferably 1.5 to 10 μm. When a polarizing plate is used, it is preferable to adjust the product of the refractive index anisotropy Δn of the liquid crystal and the cell thickness d so as to maximize the contrast. Further, when there are two polarizing plates, it is possible to adjust the polarization axis of each polarizing plate so that the viewing angle and contrast are good. Furthermore, a retardation film for expanding the viewing angle can also be used. Examples of the spacer include glass particles, plastic particles, alumina particles, and photoresist material. After that, a sealing agent such as an epoxy thermosetting composition is screen-printed on the substrates with a liquid crystal injection port provided, the substrates are bonded to each other, and the sealing agent is thermally cured by heating.

As a method for sandwiching the polymerizable compound-containing liquid crystal composition between the two substrates, a usual vacuum injection method or ODF method can be used.

As a method of polymerizing the polymerizable compound contained in the polymerizable compound-containing liquid crystal composition, in order to obtain a good alignment performance of the liquid crystal, an appropriate polymerization rate is desirable, so that an active energy ray such as an ultraviolet ray or an electron beam is used. A method of polymerizing by irradiating a single type or a combination or sequential irradiation is preferable. When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used. Further, when the polymerization is carried out in a state where the polymerizable compound-containing liquid crystal composition is sandwiched between two substrates, at least the substrate on the irradiation surface side must be provided with appropriate transparency to active energy rays. I have to. Moreover, after polymerizing only a specific part using a mask during light irradiation, the orientation state of the unpolymerized part is changed by changing the conditions such as electric field, magnetic field or temperature, and further irradiation with active energy rays is performed. It is also possible to use a means of polymerizing the polymer. In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating electric field to the polymerizable compound-containing liquid crystal composition. The AC electric field to be applied is preferably AC having a frequency of 10 Hz to 10 kHz, more preferably 60 Hz to 10 kHz, and the voltage is selected depending on the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In the PSVA mode liquid crystal display element, it is preferable to control the pretilt angle from 80 degrees to 89.9 degrees from the viewpoint of alignment stability and contrast.

The temperature at the time of irradiation with active energy rays such as ultraviolet rays or electron rays used when polymerizing the polymerizable compound contained in the polymerizable compound-containing liquid crystal composition is not particularly limited. For example, when the polymerizable compound-containing liquid crystal composition is applied to a liquid crystal display device provided with a substrate having an alignment film, it is preferably within a temperature range in which the liquid crystal state of the polymerizable compound-containing liquid crystal composition is maintained. .. It is preferable to polymerize at a temperature close to room temperature, that is, typically at 15 to 35°C.

On the other hand, for example, when the polymerizable compound-containing liquid crystal composition is applied to a liquid crystal display device provided with a substrate having no alignment film, when applied to a liquid crystal display device provided with a substrate having the above alignment film A wider temperature range than the above temperature range may be used.

A metal halide lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, or the like can be used as the lamp that generates ultraviolet rays. As the wavelength of the ultraviolet rays to be irradiated, it is preferable to irradiate the ultraviolet rays in a wavelength range other than the absorption wavelength range of the polymerizable compound-containing liquid crystal composition, and it is preferable to use the ultraviolet rays after cutting the ultraviolet rays if necessary. The intensity of the ultraviolet rays applied is preferably 0.1 mW/cm ² to 100 W/cm ^{2, and} more preferably ² mW/cm ² to 50 W/cm ² . The amount of energy of the ultraviolet rays to be irradiated can be appropriately adjusted, but is preferably 10 mJ/cm ² to 500 J/cm ^{2, and} more preferably 100 mJ/cm ² to 200 J/cm ² . The intensity may be changed when the ultraviolet rays are irradiated. The time for irradiating with ultraviolet rays is appropriately selected depending on the intensity of ultraviolet rays for irradiation, but is preferably 10 seconds to 3600 seconds, more preferably 10 seconds to 600 seconds.

III. Polymerizable Compound The polymerizable compound of the present invention is a compound represented by the general formula (i).

(In the formula, A ⁱ¹ and A ⁱ² are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═) and (c). Naphthalenediyl group, 1,2,3,4-tetrahydronaphthalenediyl group or decahydronaphthalenediyl group (one -CH= present in naphthalenediyl group or 1,2,3,4-tetrahydronaphthalenediyl group) Two or more -CH= that are not adjacent to each other may be replaced with -N=.)
Represents a group selected from the group consisting of: the group (a), the group (b) and the group (c) each independently represent an alkyl group having 1 to 8 carbon atoms and a group having 1 to 8 carbon atoms. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or P ⁱ³ —S ⁱ³ —,
P ⁱ¹ , P ^i2, and P ⁱ³ are each independently the formula (R-1) to the formula (R-9).

(In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and m ^r5 , m ^r7 , n ^r5 and n ^r7 each independently represent a group selected from 0, 1, or 2),
S ⁱ¹ , S ⁱ² and S ⁱ³ each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH ₂ — in the alkylene group or two or more not adjacent to each other. -CH _2- may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other,
R ⁱ¹ represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom,
n ⁱ¹ represents 1, 2 or 3,
When there are a plurality of A ⁱ² , S ⁱ² , P ⁱ³ and/or S ⁱ³ , they may be the same or different. )

According to the polymerizable compound of the present invention, when the polymerizable compound-containing liquid crystal composition is added to the liquid crystal composition, it is difficult to precipitate from the polymerizable compound-containing liquid crystal composition, the polymerization rate is fast, and the ultraviolet rays are short. Since sufficient polymerization is possible even by irradiation, the amount of unreacted polymerizable compound remaining can be reduced. Further, according to the polymerizable compound of the present invention, it is possible to suppress display failure (burn-in) due to a large change in the pretilt angle in the liquid crystal display element.

Since the details of the polymerizable compound of the present invention have been described in the above section “I. Polymerizable compound-containing liquid crystal composition”, description thereof will be omitted here.

The present invention is not limited to the above embodiment. The above-described embodiment is merely an example, and the invention having substantially the same configuration as the technical idea described in the scope of claims of the present invention and exhibiting the same action and effect is the present invention It is included in the technical scope of.

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Moreover, "%" in the following Examples and Comparative Examples means "mass %".

The following abbreviations are used for the description of compounds in the following examples and comparative examples.

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

(Linking group)
-1O- -CH ₂ -O-
-2- --CH ₂ --CH ₂ -

(Ring structure)

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

Tni: Nematic phase-isotropic liquid phase transition temperature (°C)
Δn: refractive index anisotropy at 20°C η: viscosity at 20°C (mPa·s)
γ ₁ : rotational viscosity at 20°C (mPa·s)
Δε: Dielectric anisotropy at 20° C.

The manufacturing method and evaluation method of liquid crystal display elements in the following examples and comparative examples are as follows.

(Method of manufacturing liquid crystal display element)
First, a polymerizable compound-containing liquid crystal composition to be described later was injected by a vacuum injection method into a liquid crystal cell having a cell gap of 3.5 μm and including a substrate with ITO, which was coated with a polyimide alignment film that induces vertical alignment and rubbed. Then, the liquid crystal cell in which the polymerizable compound-containing liquid crystal composition was injected was irradiated with ultraviolet rays for an arbitrary time using a fluorescent UV lamp to obtain a liquid crystal display element. At this time, the fluorescent UV lamp was adjusted so that the illuminance measured under the condition of the central wavelength of 313 nm was 3 mW/cm ² .

(Method of evaluating residual amount of polymerizable compound)
Under the irradiation conditions described above, the residual amount [ppm] of the polymerizable compound in the liquid crystal display device after irradiation with ultraviolet rays for 150 seconds, 15 minutes or 60 minutes was measured. A method for measuring the residual amount of the polymerizable compound will be described. First, the decomposed liquid crystal display element and acetonitrile were put in a test tube, shaken and filtered to obtain an acetonitrile solution of an elution component containing a liquid crystal composition, a polymer and an unreacted polymerizable compound. This was analyzed by a high performance liquid chromatograph (column: reversed-phase non-polar column, developing solvent: mixed solvent of acetonitrile 70% and water 30%) to calculate the peak area of each component. The amount of the remaining polymerizable compound was determined from the peak area ratio of the liquid crystal compound as an index and the peak area of the unreacted polymerizable compound. The residual amount of the polymerizable compound was determined from this value and the amount of the polymerizable compound initially added. The detection limit of the residual amount of the polymerizable compound was 100 ppm.

(VHR evaluation method)
The liquid crystal cell in which the polymerizable compound-containing liquid crystal composition was injected was irradiated with ultraviolet rays for 60 minutes under the above irradiation conditions, and VHR was measured. The measurement conditions of VHR were 1 V, 0.6 Hz, and 60°C.

(Evaluation method for burn-in)
The liquid crystal cell in which the polymerizable compound-containing liquid crystal composition was injected was irradiated with ultraviolet rays for 60 minutes under the above irradiation conditions, and then the display defect (burn-in) was evaluated due to the change in the pretilt angle. First, the pretilt angle of the liquid crystal display element was measured and used as the pretilt angle (initial). A backlight was irradiated for 3 hours while applying a voltage of 30 V at a frequency of 100 Hz to this liquid crystal display element. Then, the pretilt angle was measured and used as the pretilt angle (after the test). The value obtained by subtracting the pretilt angle (after the test) from the measured pretilt angle (initial) was taken as the pretilt angle change amount (=absolute value of pretilt angle change) [°]. The pretilt angle was measured using OPTIPRO manufactured by Shintech. The closer the pretilt angle change amount is to 0[°], the lower the possibility of display failure due to the change of the pretilt angle becomes, and when it becomes 0.5[°] or more, the display failure due to the change of the pretilt angle occurs. More likely.

1. Synthesis of Polymerizable Compound (Example 1A) Synthesis of Polymerizable Compound Represented by Formula (i-1a)

First, in a nitrogen atmosphere, in a reaction vessel, 10.0 g of a compound represented by the formula (i-1a-1), tert-butyl acrylate 8.9 g, potassium carbonate 12.0 g, N,N-dimethylacetamide 100 mL, palladium acetate (II) 0.010 g was added, and the mixture was heated with stirring at 120° C. for 5 hours. After cooling to room temperature, the reaction solution was poured into 5% hydrochloric acid. It was extracted with ethyl acetate, and the organic layer was washed successively with water and brine. Purification by column chromatography (alumina, ethyl acetate) gave 10.2 g of the compound represented by the formula (i-1a-2).

Next, under a nitrogen atmosphere, 10.2 g of the compound represented by the formula (i-1a-2), 4.4 g of methacrylic acid, 0.6 g of 4-dimethylaminopyridine, and 100 mL of dichloromethane were added to a reaction vessel. While cooling with ice, 7.0 g of diisopropylcarbodiimide was added dropwise, and the mixture was stirred at room temperature for 7 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 5% hydrochloric acid, water and brine. Purification by column chromatography (silica gel, dichloromethane/hexane) gave 10.7 g of the compound represented by the formula (i-1a-3).

Next, 10.7 g of the compound represented by the formula (i-1a-3), 30 mL of dichloromethane and 60 mL of formic acid were added to a reaction vessel, and the mixture was heated with stirring at 40° C. for 6 hours. After evaporating the solvent under reduced pressure, the obtained solid was washed with water. By drying, 8.2 g of the compound represented by the formula (i-1a-4) was obtained.

Subsequently, 10.0 g of the compound represented by the formula (i-1a-5), 1.3 g of pyridinium p-toluenesulfonate, and 100 mL of dichloromethane were added to the reaction vessel. While cooling with ice, 5.0 g of 3,4-dihydro-2H-pyran was added dropwise, and the mixture was stirred at room temperature for 8 hours. The reaction solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine. Purification by column chromatography (alumina, dichloromethane) gave 12.8 g of the compound represented by the formula (i-1a-6).

Next, 12.8 g of the compound represented by the formula (i-1a-6), 50 mL of tetrahydrofuran, 50 mL of ethanol, and a palladium catalyst (E106 O/W 5% Pd manufactured by Evonik) were added to the pressure resistant reactor. The mixture was heated and stirred at a hydrogen pressure of 0.5 MPa and 50° C. for 8 hours. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure. Purification by column chromatography (alumina, ethyl acetate) yielded 8.3 g of a compound represented by the formula (i-1a-7).

Next, under a nitrogen atmosphere, 8.3 g of the compound represented by the formula (i-1a-7), 4.0 g of methacrylic acid, 0.5 g of 4-dimethylaminopyridine, and 90 mL of dichloromethane were added to a reaction vessel. While cooling with ice, 6.5 g of diisopropylcarbodiimide was added dropwise, and the mixture was stirred at room temperature for 7 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 5% hydrochloric acid, water and brine. Purification by column chromatography (alumina, dichloromethane) gave 9.0 g of a compound represented by the formula (i-1a-8).

Next, 9.0 g of the compound represented by the formula (i-1a-8), 70 mL of tetrahydrofuran, 70 mL of methanol, and 0.1 mL of concentrated hydrochloric acid were added to a reaction vessel, and the mixture was stirred at room temperature for 6 hours. Ethyl acetate was added to the reaction solution, which was washed successively with water and brine. Purification by column chromatography (alumina, ethyl acetate) and recrystallization (ethyl acetate/hexane) yielded 5.5 g of a compound represented by the formula (i-1a-9).

In a nitrogen atmosphere, 5.5 g of the compound represented by the formula (i-1a-9), 7.1 g of the compound represented by the formula (i-1a-4) and 0.4 g of 4-dimethylaminopyridine in a reaction vessel under a nitrogen atmosphere. 100 mL of dichloromethane was added. While cooling with ice, 4.7 g of diisopropylcarbodiimide was added dropwise, and the mixture was stirred at room temperature for 7 hours. The precipitate was removed by filtration, and the filtrate was washed successively with 5% hydrochloric acid, water and brine. Purification by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane/methanol) gave 9.7 g of a compound represented by the formula (i-1a).

The phase transition temperature, ¹ H NMR peak value, and LC-MS of the obtained compound represented by the formula (i-1a) were as follows.
-Phase transition temperature (temperature rise 5°C/min): C 161 I
¹ H NMR (CDCl ₃ ) δ 2.08 (m, 6H), 5.78 (d, 2H), 6.37 (d, 2H), 6.59 (d, 1H), 7.16-7 .22 (m, 6H), 7.63 (d, 2H), 7.86 (d, 1H) ppm
・LC-MS: 393 [M+1]

(Example 2A) Synthesis of polymerizable compound represented by formula (i-24a)

First, 13.8 g of the compound represented by the formula (i-24a-1), 1.4 g of p-toluenesulfonic acid monohydrate, and 150 mL of ethyl acetate were added to a reaction vessel equipped with a Dean-Stark apparatus. While the solvent was removed, new ethyl acetate was added, and the mixture was heated under reflux for 5 hours. After cooling, the reaction solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine. Purification by column chromatography (alumina, ethyl acetate) and recrystallization (ethyl acetate/hexane) gave 13.9 g of the compound represented by the formula (i-24a-2).

Next, under a nitrogen atmosphere, 13.9 g of the compound represented by the formula (i-24a-2), 0.3 g of pyridinium p-toluenesulfonic acid, and 60 mL of dichloromethane were added to a reaction vessel. With cooling with ice, 7.5 g of 3,4-dihydro-2H-pyran was added dropwise, and the mixture was stirred at room temperature for 10 hours. The reaction solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine. Purification by column chromatography (alumina, dichloromethane) and recrystallization (dichloromethane/methanol) gave 16.6 g of a compound represented by the formula (i-24a-3).

Next, 16.6 g of the compound represented by the formula (i-24a-3) and 300 mL of methanol were added to the reaction vessel. 8.4 mL of 50% sodium hydroxide aqueous solution was added at room temperature, and the mixture was heated with stirring at 50° C. for 4 hours. The reaction solution was poured into water. The aqueous layer was adjusted to pH 7 and then extracted with ethyl acetate. The organic layer was washed successively with water and brine. Purification by column chromatography (alumina, ethyl acetate) and recrystallization (ethyl acetate/hexane) gave 12.7 g of the compound represented by the formula (i-24a-4).

Next, under a nitrogen atmosphere, 12.4 g of the compound represented by the formula (i-24a-4), 0.6 g of 4-dimethylaminopyridine, 99 mL of dichloromethane, and 4.6 g of methacrylic acid were added to a reaction vessel. While cooling with ice, 6.8 g of diisopropylcarbodiimide was added dropwise, and the mixture was stirred at room temperature for 10 hours. The precipitated solid was removed by filtration, and the solvent was evaporated under reduced pressure. Recrystallization (methanol) was performed. Purification by column chromatography (NH2 silica gel, dichloromethane/hexane) and recrystallization (dichloromethane/methanol) yielded 5.4 g of a compound represented by the formula (i-24a-5).

Next, 5.4 g of the compound represented by the formula (i-24a-5), 50 mL of tetrahydrofuran, and 50 mL of methanol were added to the reaction vessel. 0.2 mL of concentrated hydrochloric acid was added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine. Purification by column chromatography (alumina, ethyl acetate) and recrystallization (ethyl acetate/hexane) yielded 4.0 g of a compound represented by the formula (i-24a-6).

Next, under a nitrogen atmosphere, 4.0 g of the compound represented by the formula (i-24a-6) in a reaction vessel, 3.5 g of the compound represented by the formula (i-1a-4) synthesized in Example 1A, 0.2 g of 4-dimethylaminopyridine and 50 mL of dichloromethane were added. 2.3 g of diisopropylcarbodiimide was added dropwise while cooling with ice, and the mixture was stirred at room temperature for 10 hours. The precipitated solid was removed by filtration, and the solvent was evaporated under reduced pressure. Recrystallization (methanol) was performed. Purification by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane/methanol) yielded 5.9 g of a compound represented by the formula (i-24a).

The phase transition temperature, ¹ H NMR peak value, and LC-MS of the obtained compound represented by the formula (i-24a) were as follows.
・Phase transition temperature (temperature increase 5° C./min): C 179 N >220 I
¹ H NMR (CDCl ₃ ) δ 1.54-1.67 (m, 4H), 1.95-2.01 (m, 5H), 2.07 (s, 3H), 2.14-2. 14 (m, 2H), 2.57 (m, 1H), 4.85 (m, 1H), 5.55 (m, 1H), 5.79 (m, 1H), 6.11 (s, 1H) ), 6.37 (s, 1H), 6.59 (d, 1H), 7.09 (d, 2H), 7.20 (d, 2H), 7.24 (d, 2H), 7.62. (D, 2H), 7.85 (d, 1H) ppm.
・LC-MS: 475 [M+1]

(Example 3A) Synthesis of polymerizable compound represented by formula (i-31a)

First, under a nitrogen atmosphere, 25.0 g of the compound represented by the formula (i-31a-1), 0.7 g of pyridinium paratoluenesulfonate, and 120 mL of dichloromethane were added to a reaction vessel. While cooling with ice, 16.8 g of 3,4-dihydro-2H-pyran was added dropwise, and the mixture was stirred at room temperature for 2 hours. Water was poured into the reaction solution, and the organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine. Purification by column chromatography (NH2 silica gel, dichloromethane) gave 38.2 g of the compound represented by the formula (i-31a-2).

Then, under a nitrogen atmosphere, 38.0 g of the compound represented by the formula (i-31a-2) and 0.5 g of dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) were placed in a reaction vessel. , Potassium carbonate (2 mol/L aqueous solution) 150 mL, and tetrahydrofuran 500 mL were added, and the mixture was heated with stirring at 60°C. A solution of 23.1 g of the compound represented by the formula (i-31a-3) in tetrahydrofuran (100 mL)/water (20 mL) was added dropwise, and the mixture was heated with stirring at 60° C. for 10 hours. After cooling to room temperature, water was poured into the reaction solution. It was extracted with ethyl acetate and the organic layer was washed with brine. Purification by column chromatography (alumina, dichloromethane) gave 45.7 g of the compound represented by the formula (i-31a-4).

Next, under a nitrogen atmosphere, 45.7 g of the compound represented by the formula (i-31a-4), 1.6 g of 4-dimethylaminopyridine, 300 mL of dichloromethane, and 14.7 g of methacrylic acid were added to a reaction vessel. While cooling with ice, 22.3 g of diisopropylcarbodiimide was added dropwise, and the mixture was stirred at room temperature for 6 hours. The precipitated solid was removed by filtration, and the organic layer was washed successively with 10% hydrochloric acid and brine. Purification by column chromatography (alumina, dichloromethane) and recrystallization (dichloromethane/methanol, −78° C.) gave 25.0 g of the compound represented by the formula (i-31a-5).

Next, 25.0 g of the compound represented by the formula (i-31a-5), 250 mL of tetrahydrofuran, and 50 mL of methanol were added to the reaction vessel. 0.2 mL of concentrated hydrochloric acid was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine. Purification by column chromatography (silica gel, dichloromethane) and recrystallization (hexane) gave 12.5 g of the compound represented by the formula (i-31a-6).

Next, under a nitrogen atmosphere, 3.7 g of the compound represented by the formula (i-31a-6) and 3.2 g of the compound represented by the formula (i-1a-4) synthesized in Example 1A were placed in a reaction vessel. 0.2 g of 4-dimethylaminopyridine and 50 mL of dichloromethane were added. 2.1 g of diisopropylcarbodiimide was added dropwise while cooling with ice, and the mixture was stirred at room temperature for 4 hours. The precipitated solid was removed by filtration, and the organic layer was washed successively with 10% hydrochloric acid and brine. Purification by column chromatography (silica gel, dichloromethane) and recrystallization (dichloromethane/methanol) gave 5.9 g of the compound represented by the formula (i-31a).

The phase transition temperature, ¹ H NMR peak value, and LC-MS of the obtained compound represented by the formula (i-31a) were as follows.
-Phase transition temperature (temperature increase 5°C/min): C160N>220I
_{^{· 1 H NMR (CDCl 3)}} δ 2.08 (s, 3H), 2.09 (s, 3H), 2.29 (s, 3H), 5.79 (dt, 2H), 6.38 (d , 2H), 6.62 (d, 1H), 7.06 (m, 2H), 7.16-7.35 (m, 7H), 7.64 (d, 2H), 7.87 (d, 1H) ppm.
・LC-MS: 483 [M+1]

(Example 4A) Synthesis of polymerizable compound represented by formula (i-33a)

First, in a nitrogen atmosphere, in a reaction vessel, 25.0 g of a compound represented by the formula (i-33a-2), 0.5 g of dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II), 160 mL of potassium carbonate (2 mol/L aqueous solution) and 500 mL of tetrahydrofuran were added, and the mixture was heated with stirring at 60°C. A solution of 35.0 g of the compound represented by the formula (i-33a-1) in tetrahydrofuran (100 mL)/water (20 mL) was added dropwise, and the mixture was heated with stirring at 60° C. for 3 hours. After cooling to room temperature, water was poured into the reaction solution. It was extracted with ethyl acetate and the organic layer was washed with brine. Purification by column chromatography (alumina, dichloromethane) gave 44.7 g of the compound represented by the formula (i-33a-3).

Subsequently, under a nitrogen atmosphere, 44.7 g of the compound represented by the formula (i-33a-3), 1.6 g of 4-dimethylaminopyridine, 300 mL of dichloromethane, and 12.7 g of methacrylic acid were added to a reaction vessel. While cooling with ice, 20.3 g of diisopropylcarbodiimide was added dropwise, and the mixture was stirred at room temperature for 2 hours. The precipitated solid was removed by filtration, and the organic layer was washed successively with 10% hydrochloric acid and brine. Purification by column chromatography (alumina, dichloromethane) and recrystallization (dichloromethane/methanol) gave 37.0 g of the compound represented by the formula (i-33a-4).

Subsequently, 37.0 g of the compound represented by the formula (i-33a-4), 250 mL of tetrahydrofuran, and 50 mL of methanol were added to the reaction vessel. 0.2 mL of concentrated hydrochloric acid was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with brine. Purification by column chromatography (silica gel, dichloromethane) and reprecipitation (hexane) gave 25.3 g of the compound represented by the formula (i-33a-5).

Under a nitrogen atmosphere, 3.7 g of the compound represented by the formula (i-33a-5), 3.2 g of the compound represented by the formula (i-1a-4) synthesized in Example 1A, and 4-dimethyl in a reaction vessel. 0.2 g of aminopyridine and 50 mL of dichloromethane were added. 2.1 g of diisopropylcarbodiimide was added dropwise while cooling with ice, and the mixture was stirred at room temperature for 5 hours. The precipitated solid was removed by filtration, and the organic layer was washed successively with 10% hydrochloric acid and brine. Purification by column chromatography (silica gel, dichloromethane), recrystallization (dichloromethane/methanol) and column chromatography (silica gel, dichloromethane/hexane) gave 1.8 g of the compound represented by the formula (i-33a). It was

The phase transition temperature, ¹ H NMR peak value, and LC-MS of the obtained compound represented by the formula (i-33a) were as follows.
・Phase transition temperature (temperature increase 5° C./min): C 165 N 200 poly
_{^{· 1 H NMR (CDCl 3)}} δ 2.08 (s, 6H), 2.29 (s, 3H), 5.78 (dt, 2H), 6.37 (dt, 2H), 6.63 (d , 1H), 7.01 (m, 2H), 7.22 (m, 5H), 7.35 (m, 2H), 7.64 (d, 2H), 7.88 (d, 1H) ppm.
・LC-MS: 483 [M+1]

(Example 5A) Synthesis of Polymerizable Compounds Represented by Formulas (i-2a) and (i-18a) Represented by formulas (i-2a) and (i-18a) according to the method of Example 1A. The respective polymerizable compounds were synthesized.

2. Preparation of Liquid Crystal Composition Containing Polymerizable Compound and Evaluation Results (Preparation of Liquid Crystal Composition and Physical Properties)
Liquid crystal compositions LC-001 to LC-005 before adding the polymerizable compound were prepared, and the physical properties thereof were measured. Table 1 shows the configurations of the liquid crystal compositions LC-001 to LC-005 and the results of their physical properties.

(Comparative Examples 1 and 2)
A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the following formula (A) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001 was designated as Comparative Example 1. did.

A polymerizable compound-containing liquid crystal composition prepared by adding 0.3 part by mass of a compound represented by the following formula (B) as a polymerizable compound to Comparative Example 2 was added to Liquid Crystal Composition LC-001 as 99.7 parts by mass. did.

(Examples 1B to 4B)
A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-1a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001 was used as Example 1B. And

A polymerizable compound-containing liquid crystal containing a polymerizable compound obtained by adding 0.3 part by mass of the compound represented by the formula (i-24a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. The composition was Example 2B.

A polymerizable compound-containing liquid crystal containing a polymerizable compound obtained by adding 0.3 part by mass of the compound represented by the formula (i-31a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. The composition was Example 3B.

A polymerizable compound-containing liquid crystal containing a polymerizable compound obtained by adding 0.3 part by mass of the compound represented by the formula (i-33a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. The composition was Example 4B.

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Examples 1 and 2 and Examples 1B to 4B, the residual amount of the polymerizable compound after irradiation with ultraviolet rays for a predetermined time, VHR after irradiation with ultraviolet rays for 60 minutes, and pretilt angle change amount are as follows. Table 2 below. The physical properties of the polymerizable compound-containing liquid crystal compositions of Comparative Examples 1 to 2 and Examples 1B to 4B were the same as those of the liquid crystal composition LC-001.

In the polymerizable compound-containing liquid crystal composition of Comparative Example 1, the pretilt angle change amount was a sufficiently small value, but the amount of the polymerizable compound remaining after irradiation with ultraviolet rays for 60 minutes was large. In the polymerizable compound-containing liquid crystal composition of Comparative Example 2, the residual amount of the polymerizable compound after irradiation with ultraviolet rays for 60 minutes was less than the detection limit, but the amount of change in pretilt angle was large.

On the other hand, in Examples 1B to 4B, which are the polymerizable compound-containing liquid crystal compositions of the present invention, the residual amount of the polymerizable compound after irradiation with ultraviolet rays for 60 minutes was less than the detection limit, and the amount was significantly smaller than that in Comparative Example 1. Indicated. From this, it was found that the polymerization rate of the polymerizable compound in Examples 1B to 4B was sufficiently higher than that in Comparative Example 1. It was also confirmed that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2. Furthermore, in Examples 1B to 4B, the VHR after irradiation with ultraviolet rays for 60 minutes was a sufficiently high value as compared with Comparative Examples 1 and 2.

From the above, in the polymerizable compound-containing liquid crystal composition of the present invention, the polymerization rate of the polymerizable compound represented by the general formula (i) is sufficiently high, and the residual amount of the unreacted polymerizable compound is suppressed. It was confirmed that the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently high and that a display defect due to a change in the pretilt angle was unlikely to occur.

(Comparative example 3)
Comparative Example 3 was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (C) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. ..

In the polymerizable compound-containing liquid crystal composition of Comparative Example 3, the residual amount and VHR of the polymerizable compound after irradiation with ultraviolet rays for 60 minutes and the result of the pretilt angle change amount were the same as those in Examples 1B to 4B, but at room temperature. When it was stored at 240° C. for 240 hours, the precipitation of the polymerizable compound was confirmed. On the other hand, the polymerizable compound-containing liquid crystal compositions of Examples 1B to 4B retained a uniform nematic liquid crystal phase even after being stored at room temperature for 240 hours, and precipitation of the polymerizable compound was not confirmed.

From the above, it was confirmed that the polymerizable compound-containing liquid crystal composition of the present invention suppressed the precipitation of the polymerizable compound represented by the general formula (i). The polymerizable compound represented by the formula (C) used in Comparative Example 3 corresponds to the case where the number of A ⁱ¹ in the general formula (i) is two. From the results of Comparative Example 3, when A ⁱ¹ in the general formula (i) is 2 or more, the solubility is lowered and the compound is easily precipitated, and in the compound represented by the general formula (i) in the present invention, There was one A ⁱ¹ in the general formula (i), which suggests that the solubility is improved and precipitation is less likely to occur.

(Examples 5B to 8B)
A polymerizable compound-containing liquid crystal composition obtained by adding 0.4 part by mass of the compound represented by the formula (i-1a) as a polymerizable compound to Example 9B was obtained based on 99.6 parts by mass of the liquid crystal composition LC-001. And

A polymerizable compound-containing liquid crystal composition obtained by adding 0.6 part by mass of the compound represented by the formula (i-1a) as a polymerizable compound to 99.4 parts by mass of the liquid crystal composition LC-001 was prepared as Example 6B. And

A polymerizable compound-containing liquid crystal composition obtained by adding 50 ppm of the antioxidant represented by the formula (H-1) to Example 1 was used as Example 7B.

Example 8B was a liquid crystal composition containing a polymerizable compound in which 50 ppm of the antioxidant represented by the formula (H-2) was further added to Example 1.

The polymerizable compound-containing liquid crystal compositions of Examples 5B to 8B were evaluated in the same manner as in Example 1B. As a result, in Examples 5B to 8B, as in Example 1B, the residual amount of the unreacted polymerizable compound after irradiation with ultraviolet rays for 60 minutes was less than the detection limit, and the polymerization rate was higher than that in Comparative Example 1, The amount of change in pretilt angle was sufficiently smaller than in Example 2. In addition, in Examples 5B to 8B, the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than that in Comparative Examples 1 and 2. Further, in Examples 5B to 8B, precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 5B to 8B also solved the problems of the present invention.

(Examples 9B to 12B)
Example 9B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-1a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-002. And

Example 10B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-1a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-003. And

A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-1a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-004 was used as Example 11B. And

Example 12B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-1a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-005. And

The polymerizable compound-containing liquid crystal compositions of Examples 9B to 12B were evaluated in the same manner as in Example 1B. As a result, in all of Examples 9B to 12B, the residual amount of the unreacted polymerizable compound after irradiation with ultraviolet rays for 150 seconds and after irradiation with ultraviolet rays for 15 minutes was the same as that of Example 1B, which was smaller than that of Comparative Example 1. Further, the residual amount of the unreacted polymerizable compound in Examples 9B to 12B after irradiation with ultraviolet rays for 60 minutes was also less than the detection limit as in Example 1B. Therefore, it was suggested that Examples 9B to 12B had a higher polymerization rate than Comparative Example 1. Further, Examples 9B to 12B all showed the same amount of change in pretilt angle as Example 1B, suggesting that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2. In addition, in Examples 9B to 12B, the VHR after irradiation with ultraviolet rays for 60 minutes was equivalent to that in Example 1B, and the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than those in Comparative Examples 1 and 2. Furthermore, in Examples 9B to 12B, precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 9B to 12B solved the problems of the present invention.

(Examples 13B to 16B)
A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-31a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-002 was used as Example 13B. And

Example 14B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-31a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-003. And

A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-31a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-004 was used as Example 15B. And

Example 16B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-31a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-005. And

The polymerizable compound-containing liquid crystal compositions of Examples 13B to 16B were evaluated in the same manner as in Example 3B. As a result, in all of Examples 13B to 16B, the residual amount of the unreacted polymerizable compound after irradiation with ultraviolet rays for 150 seconds and after irradiation with ultraviolet rays for 15 minutes was the same as that of Example 3B, which was smaller than that of Comparative Example 1. Further, the residual amount of the unreacted polymerizable compound in Examples 13B to 16B after irradiation with ultraviolet rays for 60 minutes was also less than the detection limit as in Example 3B. Therefore, it was suggested that Examples 13B to 16B had a higher polymerization rate than Comparative Example 1. Further, Examples 13B to 16B all showed the same amount of change in pretilt angle as Example 3B, suggesting that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2. In addition, in Examples 13B to 16B, the VHR after irradiation with ultraviolet rays for 60 minutes was equivalent to that in Example 3B, and the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than that in Comparative Examples 1 and 2. Furthermore, in Examples 13B to 16B, precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 13B to 16B solved the problem of the present invention.

(Examples 17B to 20B)
A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by formula (i-33a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-002 was used as Example 17B. And

A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-33a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-003 was used as Example 18B. And

Example 19B was a liquid crystal composition containing a polymerizable compound in which 0.3 part by mass of the compound represented by the formula (i-33a) was added as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-004. And

A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-33a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-005 was used as Example 20B. And

The polymerizable compound-containing liquid crystal compositions of Examples 17B to 20B were evaluated in the same manner as in Example 4B. As a result, in each of Examples 17B to 20B, the residual amount of the unreacted polymerizable compound after irradiation with ultraviolet rays for 150 seconds and after irradiation with ultraviolet rays for 15 minutes was the same as that of Example 4B, which was smaller than that of Comparative Example 1. Further, the residual amount of the unreacted polymerizable compound in Examples 17B to 20B after irradiation with ultraviolet rays for 60 minutes was also less than the detection limit as in Example 4B. Therefore, it was suggested that Examples 17B to 20B had a higher polymerization rate than Comparative Example 1. Further, Examples 17B to 20B all showed the same amount of change in pretilt angle as Example 4B, suggesting that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2. Further, in Examples 17B to 20B, the VHR after irradiation with ultraviolet rays for 60 minutes was the same as that of Example 4B, and the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than those in Comparative Examples 1 and 2. Furthermore, in Examples 17B to 20B, precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 17B to 20B solved the problems of the present invention.

(Examples 21B to 22B)
A polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by the formula (i-2a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001 was used as Example 21B. And

Example 22B was a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 part by mass of the compound represented by formula (i-18a) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And

The polymerizable compound-containing liquid crystal compositions of Examples 21B to 22B were evaluated in the same manner as in Example 1B. As a result, in each of Examples 21B to 22B, the residual amount of the unreacted polymerizable compound after the irradiation of the ultraviolet rays for 150 seconds and the irradiation of the ultraviolet rays for 15 minutes was the same as that of Example 1B, which was smaller than that of Comparative Example 1. Further, the residual amount of the unreacted polymerizable compound in Examples 21B to 22B after irradiation with ultraviolet rays for 60 minutes was also less than the detection limit as in Example 1B. Therefore, it was suggested that Examples 21B to 22B had a higher polymerization rate than Comparative Example 1. Further, Examples 21B to 22B all showed the same amount of change in pretilt angle as Example 1B, suggesting that the amount of change in pretilt angle was sufficiently smaller than that in Comparative Example 2. Further, in Examples 21B to 22B, the VHR after irradiation with ultraviolet rays for 60 minutes was equivalent to that in Example 1B, and the VHR after irradiation with ultraviolet rays for 60 minutes was sufficiently higher than that in Comparative Examples 1 and 2. Furthermore, in Examples 21B to 22B, precipitation of the polymerizable compound after storage for 240 hours at room temperature was not confirmed. From this, it was confirmed that the polymerizable compound-containing liquid crystal compositions of Examples 21B to 22B solved the problem of the present invention.

Claims (9)

General formula (i)

(In the formula, A ⁱ¹ and A ⁱ² are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═) and (c). Naphthalenediyl group, 1,2,3,4-tetrahydronaphthalenediyl group or decahydronaphthalenediyl group (one -CH= present in naphthalenediyl group or 1,2,3,4-tetrahydronaphthalenediyl group) Two or more -CH= that are not adjacent to each other may be replaced with -N=.)
Represents a group selected from the group consisting of: the group (a), the group (b) and the group (c) each independently represent an alkyl group having 1 to 8 carbon atoms and a group having 1 to 8 carbon atoms. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or P ⁱ³ —S ⁱ³ —,
P ⁱ¹ , P ^i2, and P ⁱ³ are each independently the formula (R-1) to the formula (R-9).

(In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and m ^r5 , m ^r7 , n ^r5 and n ^r7 each independently represent a group selected from 0, 1, or 2),
S ⁱ¹ , S ⁱ² and S ⁱ³ each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH ₂ — in the alkylene group or two or more not adjacent to each other. -CH _2- may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other,
R ⁱ¹ represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom,
n ⁱ¹ represents 1, 2 or 3,
When there are a plurality of A ⁱ² , S ⁱ² , P ⁱ³ and/or S ⁱ³ , they may be the same or different. ) A polymerizable compound-containing liquid crystal composition containing one or more polymerizable compounds represented by the formula (1). The polymerizable compound-containing liquid crystal composition according to claim 1, which contains one or more polymerizable compounds in which n ⁱ¹ in the general formula (i) represents 1. The polymerizable compound-containing liquid crystal composition according to claim 1, wherein R ⁱ¹ in the general formula (i) contains one or more polymerizable compounds each representing a hydrogen atom. Furthermore, general formulas (N-1), (N-2) and (N-3)

(In the formula, each of R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31, and R ^N32 independently represents an alkyl group having 1 to 8 carbon atoms, and one of the alkyl groups or a non-adjacent group is present. Two or more —CH ₂ — of each may independently be substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are each independently (a) a 1,4-cyclohexylene group (one —CH ₂ — present in this group or adjacent Two or more —CH ₂ — which are not present may be replaced by —O—.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced with —N═).
(C) 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 One -CH= present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent -CH= may be replaced by -N=. ) And (d) represents a group selected from the group consisting of 1,4-cyclohexenylene groups, wherein the group (a), the group (b), the group (c) and the group (d) are each independently , A cyano group, optionally substituted with a fluorine atom or a chlorine atom,
Z ^N11 , Z ^N12 , Z ^N21 , Z ^N22 , Z ^N31 and Z ^N32 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- Represents
X ^N21 represents a hydrogen atom or a fluorine atom,
T ^N31 represents —CH ₂ — or an oxygen atom,
n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, and n ^N11 +n ^N12 , n ^N21 +n ^N22 and n ^N31 +n ^N32 are respectively Independently, 1, 2 or 3, and when there are a plurality of A ^N11 to A ^N32 and Z ^N11 to Z ^N32 , they may be the same or different. 4. The polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 3, which contains one kind or two or more kinds of compounds selected from the compounds represented by the formula (4). Furthermore, the general formula (L)

(In the formula, R ^L1 and R ^L2 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — groups in the alkyl group are independent of each other. And may be substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
n ^L1 represents 0, 1, 2 or 3,
A ^L1 , A ^L2 and A ^L3 are each independently (a) a 1,4-cyclohexylene group (one —CH ₂ — present in this group or two or more —CH ₂ which are not adjacent to each other). -May be replaced with -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═) and (c). 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 , -CH= present in the 3,3,4-tetrahydronaphthalene-2,6-diyl group or two or more -CH= not adjacent to each other may be replaced with -N=.)
Represents a group selected from the group consisting of, the group (a), the group (b) and the group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^L1 and Z ^L2 are each independently a single bond, —CH ₂ CH ₂ —, —(CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —. Represents OCF ₂ —, —CF ₂ O—, —CH═NN═CH—, —CH═CH—, —CF═CF— or —C≡C—,
When n ^L1 is 2 or 3 and a plurality of A ^L2 are present, they may be the same or different, and when n ^L1 is 2 or 3 and Z ^L2 is present a plurality of them. May be the same or different. However, compounds represented by formulas (N-1), (N-2) and (N-3) are excluded. 5. The polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 4, which contains one kind or two or more kinds of compounds selected from the compounds represented by the formula (4). A liquid crystal display device using the polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 5. A liquid crystal display device for driving an active matrix, which uses the liquid crystal composition containing a polymerizable compound according to any one of claims 1 to 5. A liquid crystal display device for PSA mode, PSVA mode, PS-IPS mode or PS-FFS mode, which uses the polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 5. General formula (i)

(In the formula, A ⁱ¹ and A ⁱ² are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) 1,4-phenylene group (one —CH═ present in this group or two or more —CH═ which are not adjacent to each other may be replaced by —N═) and (c). Naphthalenediyl group, 1,2,3,4-tetrahydronaphthalenediyl group or decahydronaphthalenediyl group (one -CH= present in naphthalenediyl group or 1,2,3,4-tetrahydronaphthalenediyl group) Two or more -CH= that are not adjacent to each other may be replaced with -N=.)
Represents a group selected from the group consisting of: the group (a), the group (b) and the group (c) each independently represent an alkyl group having 1 to 8 carbon atoms and a group having 1 to 8 carbon atoms. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or P ⁱ³ —S ⁱ³ —,
P ⁱ¹ , P ^i2, and P ⁱ³ are each independently the formula (R-1) to the formula (R-9).

(In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ each independently represent an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and m ^r5 , m ^r7 , n ^r5 and n ^r7 each independently represent a group selected from 0, 1, or 2),
S ⁱ¹ , S ⁱ² and S ⁱ³ each independently represent a single bond or an alkylene group having 1 to 15 carbon atoms, and one —CH ₂ — in the alkylene group or two or more not adjacent to each other. -CH _2- may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other,
R ⁱ¹ represents an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom,
n ⁱ¹ represents 1, 2 or 3,
When there are a plurality of A ⁱ² , S ⁱ² , P ⁱ³ and/or S ⁱ³ , they may be the same or different. ) A polymerizable compound represented by.