JPWO2020116555A1 - Liquid crystal composition and liquid crystal display element - Google Patents

Abstract

The problem to be solved by the present invention is that the polymerization rate of the polymerizable compound is sufficiently high, and the element using the polymerizable compound has no or extremely few display defects due to a change in the pretilt angle, and has a sufficient pretilt angle. Another object of the present invention is to provide a liquid crystal composition containing a polymerizable compound for producing a PSA-type or PSVA-type liquid crystal display element having excellent response performance, and to provide a liquid crystal display element using the same. A liquid crystal composition containing one or more polymerizable compounds represented by the general formula (I-1Np) is provided, and a liquid crystal display device using these is also provided.

Description

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

The PSA (Polymer Sustained Alignment) type liquid crystal display element has a structure in which a polymer structure is formed in a cell in order to control the pretilt angle of the liquid crystal molecule, and is practical as a liquid crystal display element due to its high-speed response and high contrast. It has been transformed.

In the production of a PSA type liquid crystal display element, a polymerizable composition containing a liquid crystal compound and a polymerizable compound is injected between substrates, and a voltage is applied to polymerize the polymerizable compound in a state where the liquid crystal molecules are oriented to polymerize the liquid crystal molecules. It is done by fixing the orientation of. It is known that the cause of the burn-in, which is a display defect of the PSA type liquid crystal display element, is due to impurities and a change in the orientation of the liquid crystal molecules (change in the pretilt angle).

The seizure caused by the change in the pretilt angle of the liquid crystal molecules is that the structure of the polymer changes when the same pattern is continuously displayed for a long time when the display element is configured, and as a result, the pretilt angle changes. Is. Therefore, a polymerizable compound that forms a polymer having a rigid structure in which the polymer structure does not change is required.

Conventionally, in order to prevent seizure by improving the rigidity of a polymer, Patent Document 1 uses a polymerizable compound having a biphenyl structure as a ring structure to form a display element, and Patent Document 2 has a ring structure. Disclosed as a display element using a polymerizable compound having a terphenyl structure.

As shown in Examples of Patent Document 1 and Patent Document 2, by using the following compound (A) having a biphenyl skeleton and compound (B) having a terphenyl skeleton, Attempts have been made to improve seizure caused by changes in the pretilt angle.

In recent years, in the manufacture of liquid crystal elements, a liquid crystal composition having an appropriately high polymerization rate has been required for the purpose of improving production efficiency. However, since the polymerization rate of the liquid crystal composition containing the compound (A) and the compound (B) is not sufficient, improvement has been required. Further, the conventional polymerizable compound has been required to further improve the pretilt angle imparting and the solubility.

WO2010 / 084823 Japanese Unexamined Patent Publication No. 2012-241125

The problem to be solved by the present invention is to obtain a polymerizable compound having a sufficiently high polymerization rate and capable of forming a pretilt angle in a shorter ultraviolet irradiation time, and a liquid crystal composition and a liquid crystal display element using the polymerizable compound. Is to provide. Further, the problem to be solved by the present invention is to manufacture a PSA type or PSVA type liquid crystal display element which has no or extremely few display defects due to a change in the pretilt angle, has a sufficient pretilt angle, and is excellent in response performance. It is an object of the present invention to provide a liquid crystal composition containing a polymerizable compound for the purpose, and to provide a liquid crystal display element using the same.

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

The liquid crystal composition containing the polymerizable compound of the present invention has a low viscosity (η) and a small viscosity without lowering the refractive index anisotropy (Δn) and the nematic phase-isotropic liquid phase transition temperature (Tni). It is a liquid crystal composition that exhibits rotational viscosity (γ1) and a large elastic constant (K33), has a sufficiently high polymerization rate and pretilt angle formation of the polymerizable compound, and does not precipitate the polymerizable compound. In addition, the liquid crystal display element using the liquid crystal composition of the present invention has a sufficient pretilt angle, a small residual amount of the polymerizable compound, a high voltage retention rate (VHR), a high-speed response, and poor orientation. It shows excellent display quality with no or suppressed display defects such as burn-in.

In the liquid crystal composition of the present invention, the pretilt angle and the residual amount of the polymerizable compound can be controlled by using a specific polymerizable compound, and the production efficiency can be easily improved by optimizing and reducing the energy cost for production. .. Therefore, the liquid crystal composition of the present invention and the liquid crystal display device using the same are very useful.

The liquid crystal composition of the present invention has the general formula (I).

(In the formula, X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ are independently hydrogen atom, halogen atom, cyano group, nitro group or alkyl having 1 to 8 carbon atoms. Group or formula (i-Z)

When X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ or X ⁱ⁷ represent an alkyl group, one −CH ₂ − or present in the alkyl group represents the group represented by. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. The hydrogen atom in the alkyl group may be replaced with a fluorine atom, provided that at least one of X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ . Represents a group represented by the formula (iZ).
^Mi1 and ^Mi2 are independent of each other
(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 = existing in this group or two or more -CH = not adjacent to each other may be replaced with -N =) and (c). Naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2) , 6-Diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-Diyl group contains one -CH = or two or more non-adjacent -CH = to -N = May be replaced.)
Represents a group selected from the group consisting of, and the above groups (a), groups (b) and groups (c) are independently alkyl groups having 1 to 8 carbon atoms and alkoxy groups having 1 to 8 carbon atoms. It may be replaced with a group, an alkyl halide group having 1 to 8 carbon atoms, an alkoxy halide group having 1 to 8 carbon atoms, a halogen atom, a cyano group, a nitro group or −S ^i3- P ⁱ³ .
L ⁱ¹ and ^{L i2} are each independently a single _{bond, -C 2 H 4 -, -} C 3 H 6 -, - C 4 H 8 -, - OCH 2 -, - CH 2 O -, - CO-, -COO-, -OCO-, -OCOOCH _2- , -CH ₂ OCOO-, -OCH ₂ CH ₂ O-, -CH = CRa-COO-, -CH = CRa-OCO-, -COO-CRa = CH- , -OCO-CRa = CH-, -COO-CRa = CH-COO-, -COO-CRa = CH-OCO-, -OCO-CRa = CH-COO-, -OCO-CRa = CH-OCO-,- _{CH 2 OCO -, - COOCH 2} -, - OCOCH 2 -, - C 2 H 4 OCO -, - C 2 H 4 COO -, - COOC 2 H 4 -, - OCOC 2 H 4 -, - CH = CH- , -CF = CF-, -CF = CH-, -CH = CF-, -CF ₂ O-, -OCF _2- , -CF ₂ CH _2- , -CH ₂ CF _2- , -CF ₂ CF _2- Or -C≡C-, (in the formula, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).
Z ⁱ¹ is a halogen atom, a cyano group, a nitro ^group, an -S i2 ^{-P i2} or an alkyl group having 1 to 8 carbon atoms, the one present in the alkyl group -CH ₂ - or two or more −CH ₂₋ is replaced with −O−, −CH = CH−, −C≡C−, −COO−, −OCO−, −CO− or −S− so that oxygen atoms are not directly adjacent to each other. Also, the hydrogen atom in the alkyl group may be replaced with a fluorine atom,
Independently S ^{i1, S i2} and ^{S i3} are respectively a single bond or an alkylene group having 1 to 15 carbon atoms, one -CH ₂ in the alkylene group - or two or more -CH ₂ - Is replaced with -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO-, -OCOO- or -S- so that the oxygen atoms are not directly adjacent. Well,
P ⁱ¹ , P ⁱ² and P ⁱ³ are independently expressed in equations (R-1) to (R-9).

(In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ independently represent either 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).
^mi1 represents 0, 1 or 2, ^mi2 represents 0, 1 or 2,
^{M i1, M i2, L i1} , L i2, Z i1, S i2, S i3, P i2, or if ^{the P i3} there are a plurality, respectively, may be different and the same. )
It is a liquid crystal composition containing one kind or two or more kinds of polymerizable compounds represented by.

The liquid crystal composition containing the polymerizable compound represented by the general formula (I) can impart a desired pretilt angle with a moderately high polymerization rate and a short ultraviolet irradiation time. Further, if the polymerization rate is moderately high, the residual amount of the polymerizable compound can be reduced. Therefore, the production efficiency of manufacturing the PSA type liquid crystal display element can be improved. In addition, display defects (for example, defects such as burn-in) due to changes in the pre-tilt angle do not occur or are extremely small. The display defects in the present specification include display defects due to changes in the pretilt angle after polymerization over time, display defects due to the residual amount of unreacted polymerizable compound, and display defects due to a decrease in voltage retention rate. I am considering it.
(Polymerizable compound)
The compound represented by formula (I), the compound represented by the general formula (ia) which binds at the position X ⁱ⁶ is adjacent to the X ⁱ⁷ (if X ⁱ⁶ is substituted at the 2-position of naphthalene), X ⁱ⁶ encompasses a compound represented by the general formula (ib) which binds to a position adjacent to the ^{X i5 (if X i6} is substituted at the 1-position of the naphthalene).

In the above general formula (I), general formula (ia) and general formula (ib), X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ are independently hydrogen atoms and halogens, respectively. An atom, a cyano group, a nitro group, an alkyl group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, or the formula (i-Z). )

It is preferable to represent a group represented by. The alkyl group and the alkoxy group preferably have 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and further preferably 1 to 3 carbon atoms. The alkyl group and the alkoxy group may be linear or branched, but linear is particularly preferable. X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ are alkyl groups having 1 to 3 carbon atoms which may be independently substituted with hydrogen atom, fluorine atom and fluorine atom, respectively. Alternatively, it is more preferable to represent any of the formula (i-Z), and it is further preferable to represent an alkyl group having 1 to 3 carbon atoms or the formula (i-Z) which may be substituted with a hydrogen atom or a fluorine atom. ..

As the alkyl group having 1 to 8 carbon atoms which may be substituted with the fluorine atom, a linear alkyl group is preferable, and a methyl group, an ethyl group, a propyl group or a butyl group or a hydrogen atom of these groups is fluorine. Examples thereof include an atom-substituted alkyl fluoride group, of which a methyl group, an ethyl group, a propyl group, a monofluoromethyl group, a difluoromethyl group and a trifluoromethyl group are preferable, and a methyl group or an ethyl group is more preferable. Preferably, a methyl group is particularly preferred. From the viewpoint of electron conjugation and as the number of carbon atoms increases, the substituent becomes bulky, which tends to cause a decrease in the polymerization rate and the degree of polymerization. Therefore, a methyl group is particularly preferable.

Here, at least one of X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ represents a group represented by the formula (i-Z). More ^{preferably, X i1, X i2, X} i3 and preferably represents a group represented by at least 1 Exemplary ethynylphenylbiadamantane derivatives of ^{X i7 (i-Z),} at least Exemplary ethynylphenylbiadamantane derivatives of ^{X i1} and ^{X i2} (i-Z ) Is more preferable. In particular, when Z ⁱ¹ represents −S ^i2- P ⁱ² , it is preferable that at least one of X ⁱ¹ and X ⁱ² represents a group represented by the formula (i-Z).
When two or more groups of X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ represent a group represented by the formula (i-Z), one of a plurality of ^{mi 2} exists. It is preferable that only one represents 0, 1 or 2, and the other ^mi2 represents 0.

In the above general formula (I), general formula (ia) and general formula (ib), among X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ , a group other than a hydrogen atom is represented. The number of things is preferably 1 or more and 3 or less, more preferably 1 or 2, and particularly preferably 1.

In the general formula (I), the general formula (ia) and the general formula (ib), of the X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ , -S ^i2- P ⁱ² is used. The number of groups having is preferably 0, 1, 2 or 3, more preferably 1 or 2, and particularly preferably 1. Further, in the general formula (I), the general formula (ia) and the general formula (ib), the total number of groups having -S ^i2- P ⁱ² and the number of groups having -S ^i3- P ^i3. Is preferably 0, 1, 2 or 3, more preferably 1 or 2, and particularly preferably 1.

In the general formula (I), the general formula (ia), and the general formula (ib), ^Mi1 and ^Mi2 are independent of each other.
(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 = existing in this group or two or more -CH = not adjacent to each other may be replaced with -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) , 3,4-Tetrahydronaphthalene-2,6-Diyl One -CH = present in the group or two or more non-adjacent -CH = may be replaced with -N =).
Represents a group selected from the group consisting of, and the above groups (a), groups (b) and groups (c) are independently alkyl groups having 1 to 8 carbon atoms and 1 to 8 carbon atoms, respectively. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or a ^Pi3- S ^i3- , but it preferably represents the following structure.

(In the formula, R ^im1 and R ^im2 independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a fluorine atom, or ^Pi3 −S ⁱ³ −).
1,4-Phenylene group, 2-methyl-1,4-phenylene group, 3-methyl-1,4-phenylene group, 2-methoxy-1,4-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, more preferably 1,4-phenylene group, 2-methyl-1. , 4-Phenylene group, 3-Methyl-1,4-Phenylene group, 2-Fluoro-1,4-Phenylene group, or 3-Fluoro-1,4-Phenylene group is more preferable, 1,4- It is more preferably a phenylene group, a 2-methyl-1,4-phenylene group or a 2-fluoro-1,4-phenylene group, and particularly preferably a 1,4-phenylene group.

The general formula (I), formula (ia) and the general formula ^{(ib), L i1} and ^{L i2} are each independently a single _{bond, -C 2 H 4 -, -} C 3 H 6 -, - C _{4 H 8 -, - OCH 2} -, - CH 2 O -, - CO -, - COO -, - OCO -, - OCOOCH 2 -, - CH 2 OCOO -, - OCH 2 CH 2 O -, - CH = CRa-COO-, -CH = CRa-OCO-, -COO-CRa = CH-, -OCO-CRa = CH-, -COO-CRa = CH-COO-, -COO-CRa = CH-OCO-,- _{OCO-CRa = CH-COO -} , - OCO-CRa = CH-OCO -, - CH 2 OCO -, - COOCH 2 -, - OCOCH 2 -, - C 2 H 4 OCO -, - C 2 H 4 COO- _{, -COOC 2 H 4 -, -} OCOC 2 H 4 -, - CH = CH -, - CF = CF -, - CF = CH -, - CH = CF -, - CF 2 O -, - OCF 2 -, _{-CF 2 CH 2 -, - CH} 2 CF 2 -, - CF 2 CF 2 - or -C≡C -, the (in the formulas, Ra are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms Represents), but single bond, -CH = CH-, -CF = CF-, -C≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF _2- , -CH = CHCOO _{-, - OCOCH = CH -,} - OCH 2 CH 2 O -, - CH 2 O -, - OCH 2 -, - C 2 H 4 COO -, - OCOC 2 H 4 - or -C 1-10 alkylene It preferably represents a group, single bond, -COO-, -OCO-, -CH = CHCOO-, -OCOCH = CH-, -OCH ₂ CH ₂ O-, -CH ₂ O-, -OCH ₂ -,- _{C 2 H 4 COO -, -} OCOC 2 H 4 - or is more preferably a straight or branched alkylene group having 1 to 6 carbon atoms, a single bond, -COO -, - OCO -, - OCH _{2 CH 2 O -, - CH} 2 O -, - OCH 2 -, - C 2 H 4 COO -, - OCOC 2 H 4 - or alkylene group having a carbon number of 2 (ethylene group _(-CH 2 _CH 2 -) ) Is more preferable, and a single bond is particularly preferable.
In the general formula (I), the general formula (ia) and the general formula (ib), ^mi1 and ^mi2 independently represent 0, 1 or 2, but it is particularly preferable to represent 0 or 1. It is preferable that ^mi1 + ^mi2 represent 0, 1 or 2. In order to have a sufficient pretilt angle with a short ultraviolet irradiation time and reduce the residual amount of the polymerizable compound, ^mi1 + ^mi2 preferably represent 0 or 1, and more preferably 1. Further, when used in combination with a polymerizable compound other than the compounds represented by the general formula (I), the general formula (ia) and the general formula (ib), the residual amount of the polymerizable compound is reduced and a high voltage is maintained. In order to obtain the rate (VHR), it is preferable that ^mi1 + ^mi2 represent 0 or 1.
In the general formula (I), the general formula (ia) and the general formula (ib), ^Pi1 , ^Pi2 and ^Pi3 are all the same polymerizable groups (formulas (R-1) to (R-9)). However, it may be a different polymerizable group.

In the general formula (I), the general formula (ia) and the general formula (ib), ^Pi1 , ^Pi2 and ^Pi3 are independently represented by the formulas (R-1), formula (R-2) and formula (R-2). (R-3), formula (R-4), formula (R-5) or formula (R-7) is preferable, and formula (R-1), formula (R-2), formula (R-). 3) or the formula (R-4) is more preferable, the formula (R-1) is further preferable, and an acrylic oxy group or a methacryloxy group is particularly preferable.

At least one of P ⁱ¹ and P ⁱ² is preferably of the formula (R-1), more preferably an acrylic oxy group or a methacrylic acid group, further preferably a methacrylic oxy group, and P ⁱ¹ and P. It is particularly preferable that ⁱ² is a methacrylic acid group.

R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are preferably methyl groups or hydrogen atoms, respectively, and preferably hydrogen atoms when the polymerization rate of the polymerizable compound is important. A methyl group is preferable when it is important to reduce display defects due to changes in the pretilt angle.

In the general formula (I), the general formula (ia) and the general formula (ib), S ⁱ¹ , S ⁱ² and S ⁱ³ are independently single-bonded or linear alkylene groups having 1 to 10 carbon atoms. It is preferable to represent a linear alkylene group having 2 to 8 carbon atoms or a single bond. Is, -CH = CH - - -CH ₂ in the alkyl group, - O -, - COO-, or -OCO- may be substituted with, -CH ₂ - hydrogen may be substituted by fluorine. S ⁱ¹ , S ⁱ² and S ⁱ³ are more preferably single bonds or alkylene groups having 1 to 5 carbon atoms, and particularly preferably single bonds. If S ^i1, S ⁱ² and S ⁱ³ is a single bond, the remaining amount is sufficiently small polymerizable compounds after ultraviolet irradiation, the display failure is unlikely to occur due to a change in the pretilt angle.

In the general formula (I), the general formula (ia) and the general formula (ib), Z ⁱ¹ represents a cyano group, a nitro group, −S ^i2- P ⁱ² or an alkyl group having 1 to 8 carbon atoms, and the alkyl represents the alkyl group. -CH _2- in the group may be replaced by -CH = CH-, -C≡C-, -O-, -COO-, -OCO- or -OCOO-, but -O- is not continuous. It is preferable that −S ^i2- P ⁱ² represents a linear or branched alkyl group having 1 to 8 carbon atoms, and −CH ₂₋ in the alkyl group represents −CH = CH−, −O−, −. It preferably represents a group that may be substituted with OCO- (where -O- is not continuous). From the viewpoint of improving the reliability of the liquid crystal display element, it is particularly preferable that Z ⁱ¹ represents −S ^i2- P ⁱ² , an alkyl group having 2 to 6 carbon atoms, and an alkoxy group.
Further, the compound represented by the general formula (I) is preferably represented by the general formula (I-Np).

(In the formula, X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ are independently hydrogen atom, halogen atom, cyano group, nitro group or alkyl having 1 to 8 carbon atoms. Group or formula (i-Z)

When X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ or X ⁱ⁷ represent an alkyl group, one −CH ₂ − or present in the alkyl group represents the group represented by. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. The hydrogen atom in the alkyl group may be replaced with a fluorine atom, provided that at least one of X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ . Represents a group represented by the formula (iZ).
^{M i1,} M ⁱ² and ^{M i3} 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 = existing in this group or two or more -CH = not adjacent to each other may be replaced with -N =) and (c). Naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2) , 6-Diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-Diyl group contains one -CH = or two or more non-adjacent -CH = to -N = May be replaced.)
Represents a group selected from the group consisting of, and the above groups (a), groups (b) and groups (c) are independently alkyl groups having 1 to 8 carbon atoms and alkoxy groups having 1 to 8 carbon atoms. It may be replaced with a group, an alkyl halide group having 1 to 8 carbon atoms, an alkoxy halide group having 1 to 8 carbon atoms, a halogen atom, a cyano group, a nitro group or −S ^i3- P ⁱ³ .
L ⁱ¹ and ^{L i2} are each independently a single _{bond, -C 2 H 4 -, -} C 3 H 6 -, - C 4 H 8 -, - OCH 2 -, - CH 2 O -, - CO-, -COO-, -OCO-, -OCOOCH _2- , -CH ₂ OCOO-, -OCH ₂ CH ₂ O-, -CH = CRa-COO-, -CH = CRa-OCO-, -COO-CRa = CH- , -OCO-CRa = CH-, -COO-CRa = CH-COO-, -COO-CRa = CH-OCO-, -OCO-CRa = CH-COO-, -OCO-CRa = CH-OCO-,- _{CH 2 OCO -, - COOCH 2} -, - OCOCH 2 -, - C 2 H 4 OCO -, - C 2 H 4 COO -, - COOC 2 H 4 -, - OCOC 2 H 4 -, - CH = CH- , -CF = CF-, -CF = CH-, -CH = CF-, -CF ₂ O-, -OCF _2- , -CF ₂ CH _2- , -CH ₂ CF _2- , -CF ₂ CF _2- Or -C≡C-, (in the formula, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).
Z ⁱ¹ is a halogen atom, a cyano group, a nitro ^group, an -S i2 ^{-P i2} or an alkyl group having 1 to 8 carbon atoms, the one present in the alkyl group -CH ₂ - or two or more −CH ²⁻ is replaced with −O−, −CH = CH−, −C≡C−, −COO−, −OCO−, −CO− or −S− so that oxygen atoms are not directly adjacent to each other. Also, the hydrogen atom in the alkyl group may be replaced with a fluorine atom,
S ⁱ¹ represents a single bond
S ⁱ² and ^{S i3} are each independently a single bond or an alkylene group having 1 to 15 carbon atoms, one -CH ₂ in the alkylene group - or two or more -CH ₂ -, the oxygen It may be replaced with -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO-, -OCOO- or -S- so that the atoms are not directly adjacent.
P ⁱ¹ , P ⁱ² and P ⁱ³ are independently expressed in equations (R-1) to (R-9).

(In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ independently represent either 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).
q ⁱ¹ represents 0 or 1, ^mi2 represents 0, 1 or 2,
^{M i1, M i2, L i1} , L i2, Z i1, S i2, S i3, P i2, or if ^{the P i3} there are a plurality, respectively, may have the same or different and
The total number of ^{Pi 1} , ^{Pi 2} and ^{Pi 3} numbers included in the general formula (I) is 2 or 3. )
In the above general formula (I-Np), X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ are independently hydrogen atom, halogen atom, cyano group, nitro group and fluorine atom. An alkyl group having 1 to 8 carbon atoms which may be substituted with, an alkoxy group having 1 to 8 carbon atoms which may be substituted with a fluorine atom, or the formula (i-Z).

It is preferable to represent a group represented by. The alkyl group and the alkoxy group preferably have 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and further preferably 1 to 3 carbon atoms. The alkyl group and the alkoxy group may be linear or branched, but linear is particularly preferable. X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ are alkyl groups having 1 to 3 carbon atoms which may be independently substituted with hydrogen atom, fluorine atom and fluorine atom, respectively. Alternatively, it is more preferable to represent any of the formula (i-Z), and it is further preferable to represent an alkyl group having 1 to 3 carbon atoms or the formula (i-Z) which may be substituted with a hydrogen atom or a fluorine atom. ..

As the alkyl group having 1 to 8 carbon atoms which may be substituted with the fluorine atom, a linear alkyl group is preferable, and a methyl group, an ethyl group, a propyl group or a butyl group or a hydrogen atom of these groups is fluorine. Examples thereof include an atom-substituted alkyl fluoride group, of which a methyl group, an ethyl group, a propyl group, a monofluoromethyl group, a difluoromethyl group and a trifluoromethyl group are preferable, and a methyl group or an ethyl group is more preferable. Preferably, a methyl group is particularly preferred. From the viewpoint of electron conjugation and as the number of carbon atoms increases, the substituent becomes bulky, which tends to cause a decrease in the polymerization rate and the degree of polymerization. Therefore, a methyl group is particularly preferable.

Here, at least one of X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ represents a group represented by the formula (i-Z). More ^{preferably, X i1, X i2, X} i3 and preferably represents a group represented by at least 1 Exemplary ethynylphenylbiadamantane derivatives of ^{X i7 (i-Z),} at least Exemplary ethynylphenylbiadamantane derivatives of ^{X i1} and ^{X i2} (i-Z ) Is more preferable. In particular, when Z ⁱ¹ represents −S ^i2- P ⁱ² , it is preferable that at least one of X ⁱ¹ and X ⁱ² represents a group represented by the formula (i-Z).
When two or more groups of X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ represent a group represented by the formula (i-Z), one of a plurality of ^{mi 2} exists. It is preferable that only one represents 0, 1 or 2, and the other ^mi2 represents 0.

In the above general formula (I-Np), among X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ , the number of those representing a group other than a hydrogen atom is 1 or more and 3 or less. It is preferably 1 or 2, more preferably 1, and particularly preferably 1.

In the above general formula (I-Np), among X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ , the number of groups having −S ^i2- P ⁱ² is 0, 1, It is preferably 2 or 3, more preferably 1 or 2, and particularly preferably 1. Further, in the above general formula (I-Np), the total number of ^{Pi 1} , ^{Pi 2} and ^Pi 3 is preferably 2 or 3, and particularly preferably 2. When the total number of ^{Pi 1} , ^{Pi 2} and ^{Pi 3} is 1 or less, display defects occur due to changes in the pretilt angle, which is not preferable. Further, when the total number of ^{Pi 1} , ^{Pi 2} and ^{Pi 3} is 4 or more, the solubility in the liquid crystal composition is lowered and a sufficient amount of the polymerizable compound cannot be added, which is not preferable.

In the above general formula (I-Np), ^Mi1 , ^Mi2 and ^Mi3 are independent of each other.
(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 = existing in this group or two or more -CH = not adjacent to each other may be replaced with -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) , 3,4-Tetrahydronaphthalene-2,6-Diyl One -CH = present in the group or two or more non-adjacent -CH = may be replaced with -N =).
Represents a group selected from the group consisting of, and each of the above groups (a), group (b) and group (c) independently has an alkyl group having 1 to 8 carbon atoms and an alkoxy having 1 to 8 carbon atoms. A structure which may be substituted with a group, a halogen, a cyano group, a nitro group or a ^Pi3- S ^i3- is preferable, and the group is selected from the group consisting of the above groups (b) and (c), respectively. A structure which may be independently substituted with an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, halogen or ^Pi3- S ^i3- is more preferable, and among them, the following structure is represented. Is even more preferable

(In the formula, R ^im1 and R ^im2 independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a fluorine atom, or ^Pi3 −S ⁱ³ −).
1,4-Phenylene group, 2-methyl-1,4-phenylene group, 3-methyl-1,4-phenylene group, 2-methoxy-1,4-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, more preferably 1,4-phenylene group, 2-methyl-1. , 4-Phenylene group, 3-Methyl-1,4-Phenylene group, 2-Fluoro-1,4-Phenylene group, or 3-Fluoro-1,4-Phenylene group is more preferable, 1,4- A phenylene group, a 2-methyl-1,4-phenylene group or a 2-fluoro-1,4-phenylene group is particularly preferable, and a 1,4-phenylene group is particularly preferable. In particular, when ^Mi3 is the above-mentioned preferable group, particularly aromatic, the absorption wavelength of the polymerizable compound can be extended to a long wavelength region because the ^Mi3 and the naphthalene ring have a conjugated structure, and the polymerization rate can be increased. Since the speed is increased, the residual amount of the polymerizable compound can be reduced.

In the formula ^{(I-Np), L i1} and ^{L i2} are each independently a single _{bond, -C 2 H 4 -, -} C 3 H 6 -, - C 4 H 8 -, - OCH 2 -, -CH ₂ O-, -CO-, -COO-, -OCO-, -OCOOCH _2- , -CH ₂ OCOO-, -OCH ₂ CH ₂ O-, -CH = CRa-COO-, -CH = CRa- OCO-, -COO-CRa = CH-, -OCO-CRa = CH-, -COO-CRa = CH-COO-, -COO-CRa = CH-OCO-, -OCO-CRa = CH-COO-,- _{OCO-CRa = CH-OCO -} , - CH 2 OCO -, - COOCH 2 -, - OCOCH 2 -, - C 2 H 4 OCO -, - C 2 H 4 COO -, - COOC 2 H 4 -, - OCOC _{2 H 4 -, - CH =} CH -, - CF = CF -, - CF = CH -, - CH = CF -, - CF 2 O -, - OCF 2 -, - CF 2 CH 2 -, - CH 2 CF _2- , -CF ₂ CF _2- or -C≡C-, (in the formula, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), but a single bond,- CH = CH-, -CF = CF-, -C≡C-, -COO-, -OCO-, -CF ₂ O-, -OCF _2- , -CH = CHCOO-, -OCOCH = CH-, -OCH _{2 CH 2 O -, - CH} 2 O -, - OCH 2 -, - C 2 H 4 COO -, - OCOC 2 H 4 - or preferably represent an alkylene group having 1 to 10 carbon atoms, a single bond, -COO-, -OCO-, -CH = CHCOO-, -OCOCH = CH-, -OCH ₂ CH ₂ O-, -CH ₂ O-, -OCH _2- , -C ₂ H ₄ COO-, -OCOC ₂ H ₄ - or is more preferably a straight or branched alkylene group having 1 to 6 carbon atoms, a single _{bond, -COO -, - OCO -,} - OCH 2 CH 2 O -, - CH 2 O It is more preferable to represent −, −OCH ₂ −, −C ₂ H ₄ COO −, −OCOC ₂ H ₄ − or an alkylene group having 2 carbon atoms (ethylene group (−CH ₂ CH ₂ −)), and a single bond. Is particularly preferable.
In the above general formula (I-Np), q ⁱ¹ represents 0 or 1, and preferably 0. Although ^mi2 independently represents 0, 1 or 2, it is preferable to represent 0 or 1, and it is particularly preferable to represent 1. q ⁱ¹ + ^mi2 preferably represents 0, 1 or 2. In order to have a sufficient pretilt angle with a short ultraviolet irradiation time and reduce the residual amount of the polymerizable compound, q ⁱ¹ + ^mi2 preferably represents 0 or 1, and more preferably 1. Further, when used in combination with a polymerizable compound other than the compound represented by the general formula (I-Np), in order to reduce the residual amount of the polymerizable compound and obtain a high voltage retention rate (VHR), it is preferred that q ⁱ¹ + ^{m i2} represents 0 or 1.
In the general formula ^{(I-Np), P i1} , P i2 and P ⁱ³ represent a polymerizable group selected from the group consisting of formulas (R-1) ~ (R -9). P ^i1, P ⁱ² and P ⁱ³ may all be of the same polymerizable group, may be different polymerizable groups.

In the formula ^{(I-Np), P i1} , P i2 and P ⁱ³ are each independently formula (R-1), formula (R-2), formula (R-3), formula (R- 4), preferably of formula (R-5) or formula (R-7), with formula (R-1), formula (R-2), formula (R-3) or formula (R-4). It is more preferable to have an acrylic group, more preferably the formula (R-1), and particularly preferably an acrylic oxy group or a methacryloxy group.

At least one of P ⁱ¹ and P ⁱ² is preferably a formula (R-1), more preferably an acrylic group or a methacrylic group, both acryloxy group or methacryloxy the P ⁱ¹ and P ⁱ² It is more preferably a group, and it is particularly preferable that both ^Pi1 and ^Pi2 are methacrylicoxy groups, or one of ^Pi1 and ^Pi2 is an acrylicoxy group and the other is a methacrylicoxy group.

In the above formulas (R-1) to (R-9), R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are preferably methyl groups or hydrogen atoms, respectively, and are polymerizable compounds. A hydrogen atom is preferable when the polymerization rate of the compound is important, and a methyl group is preferable when the reduction of display defects due to a change in the pretilt angle is important.

In the above general formula (I-Np), since ^Si1 represents a single bond, ^Mi3 and the naphthalene ring can be directly bonded to effectively form a conjugated structure, so that the absorption wavelength of the polymerizable compound can be determined. It can be expanded to a long wavelength region, the polymerization rate can be increased, and the residual amount of the polymerizable compound can be reduced.
In the above general formula (I-Np), S ⁱ² and S ⁱ³ each independently represent a single bond or a linear alkylene group having 1 to 10 carbon atoms, and preferably have 2 to 8 carbon atoms. More preferably, it represents a linear alkylene group or a single bond. Is, -CH = CH - - -CH ₂ in the alkyl group, - O -, - COO-, or -OCO- may be substituted with, -CH ₂ - hydrogen may be substituted by fluorine. S ⁱ² and S ⁱ³ are more preferably single bonds or alkylene groups having 1 to 5 carbon atoms, and particularly preferably single bonds. When S ⁱ² and S ⁱ³ are single bonds, the residual amount of the polymerizable compound after irradiation with ultraviolet rays is sufficiently small, and display defects due to changes in the pretilt angle are less likely to occur.

In the above general formula (I-Np), Z ⁱ¹ represents a cyano group, a nitro group, -S ^i2- P ⁱ² or an alkyl group having 1 to 8 carbon atoms, and -CH _2- in the alkyl group represents -CH. = CH-, -C≡C-, -O-, -COO-, -OCO- or -OCOO- may be substituted, but -O- is preferably not continuous, -S ^i2- P ⁱ² , Represents a linear or branched alkyl group having 1 to 8 carbon atoms, and −CH ₂ − in the alkyl group is replaced with −CH = CH−, −O−, −OCO− (where −O− is It is preferable to represent a group that may be (not continuous). From the viewpoint of improving the reliability of the liquid crystal display element, Z ⁱ¹ preferably represents -S ^i2- P ⁱ² , an alkyl group having 2 to 6 carbon atoms, and an alkoxy group, and preferably represents -S ^i2- P ^i2. Is particularly preferable.
Further, the compound represented by the above general formula (I-Np) is preferably represented by the general formula (i-Np-1) or the general formula (i-Np-2).

^{(Wherein, M in1, M in3, L} in1, S in1, S in2, P in1, P in2 and ^{q in1} is, ^M in the general formula ^{(I-Np) i1, M} i3, L i1, S i1, It has the same meaning as S ⁱ² , P ⁱ¹ , P ⁱ² and q ⁱ¹ , respectively.
X ⁱⁿ¹ , X ⁱⁿ² , X ⁱⁿ³ , X ⁱⁿ⁴ , X ⁱⁿ⁵ , ^Xin6 and ^Xin7 are independently hydrogen atoms, halogen atoms, cyano groups, nitro groups or alkyl groups having 1 to 8 carbon atoms or formulas ( i-nZ)

^Represents a group represented by, and when X ⁱⁿ¹ , X ⁱⁿ² , X ⁱⁿ³ , X ⁱⁿ⁴ , X ⁱⁿ⁵ , X ⁱⁿ⁶ or X ⁱⁿ⁷ represents an alkyl group, one −CH ₂ − or present in the alkyl group. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. The hydrogen atom in the alkyl group may be replaced with a fluorine atom.
M ⁱⁿ² and ^{M in4} each independently represent the same meaning as ^{M i2} in formula (i-Z),
L ⁱⁿ² and ^{L in4} each independently represent the same meaning as ^{L i2} in formula (i-Z),
m ⁱⁿ² and ^{m in4} each independently represent the same meaning as ^{m i2} in formula (i-Z),
Z ⁱⁿ² is halogen atom, a cyano group, a nitro group, -S ⁱⁿ⁴ -P ⁱⁿ⁴ or an alkyl group having 1 to 8 carbon atoms, the one present in the alkyl group -CH ₂ - or two or more −CH ²⁻ is replaced with −O−, −CH = CH−, −C≡C−, −COO−, −OCO−, −CO− or −S− so that oxygen atoms are not directly adjacent to each other. At best, also hydrogen atoms in the alkyl group may be replaced by fluorine atoms, ^{S in4} and ^{P in4} each represent a same meaning as ^{S i2} and ^{P i2} in formula (i-nZ),
^{M in1, M in2, M in4} , L in1, L in2, L in4, m in4, ^{if Z} in2, ^{S in4} and ^{P in4} there are a plurality, respectively, may have the same or different and
However, the general formula (i-Np-1) or ^{P in1,} the total number of ^{P in2} and ^{P in4} number included in the general formula (i-Np-2) is 2 or 3. )
The general formula (i-Np-1) or general formula (i-Np-2), preferred structure of ^{M in1, M in3, L in1} , S in1, S in2, P in1, P in2 and ^{q in1} is These are the same as the preferable structures in M ⁱ¹ , M ⁱ³ , ^{Li 1} , S ⁱ¹ , S ⁱ² , P ⁱ¹ , P ^{i 2} and q ^{i 1} in the above general formula (I-Np), respectively. In the general formula (i-Np-1) or the general formula (i-Np-2), the preferred structures of X ⁱⁿ¹ , X ⁱⁿ² , ^Xin3 , ^Xin4 , ^Xin5 , ^Xin6 and ^Xin7 are the above general ^formulas , respectively. It is the same as the preferable structure in X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ in the formula (I-Np). The general formula (i-Np-1) or general formula ^(i-Np-2), M in2, L preferred structure of ⁱⁿ² and ^{m in2} is, ^M i2, respectively in the above formula ^{(i-Z), L i2} And ^mi2 are similar to the preferred structure. In the above formula ^(i-nZ), the preferred structure of the M ^{in4, L in4} and ^{m in4} are respectively the same as the preferred structure in the ^{M i2, L i2} and ^{m i2} in the formula (i-Z). In the above formula ^(i-nZ), the preferred structure of the ^{Z in2} are respectively the same as the preferred structure in ^{Z i2} in the formula (i-Z). In the above formula (i-nZ), the preferred structure of the ^{S in4} and ^{P in4} are respectively the same as the preferred structure in the ^{S i2} and ^{P i2} in the formula (i-Z).

The compounds represented by the general formula (I) are the general formula (ia-1), the general formula (ib-1), the general formula (ia-2), the general formula (ib-2), and the general formula (ia-). 3), it is preferably represented by the general formula (ib-3), the general formula (ia-4) and the general formula (ib-4).

(In the formula, X ^ia1 , X ^ia2 , X ^ia3 , X ^ia4 , X ^ia5 , X ^ia6 , X ^ia7 , X ^ib1 , X ^ib2 , X ^ib3 , X ^ib4 , X ^ib5 , X ^ib6 and X ^ib6 , respectively. Represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -S ^i4- P ^i4, or an alkyl group having 1 to 8 carbon atoms, and one -CH _2- or two or more existing in the alkyl group. −CH ₂₋ is replaced with −O−, −CH = CH−, −C≡C−, −COO−, −OCO−, −CO− or −S− so that oxygen atoms are not directly adjacent to each other. Also, the hydrogen atom in the alkyl group may be replaced with a fluorine atom,
^{P i1,} P i2, ^{S i1} and ^{S i2} of the general formula (I) represents respectively the same meaning as ^{P i1, P i2, S} i1 and ^{S i2 during, S i4} and ^{P i4} is the general formula (I) It has the same meaning as S ⁱ² and ^{Pi 2} of. )

(In the formula, X ^ia1 , X ^ia2 , X ^ia3 , X ^ia4 , X ^ia5 , X ^ia6 , X ^ia7 , X ^ib1 , X ^ib2 , X ^ib3 , X ^ib4 , X ^ib5 , X ^ib6 and X ^ib6 , respectively. Represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, -S ^i4- P ^i4, or an alkyl group having 1 to 8 carbon atoms, and one -CH _2- or two or more existing in the alkyl group. −CH ₂₋ is replaced with −O−, −CH = CH−, −C≡C−, −COO−, −OCO−, −CO− or −S− so that oxygen atoms are not directly adjacent to each other. Also, the hydrogen atom in the alkyl group may be replaced with a fluorine atom,
^{M i1, M i2, L i1} , L i2, P i1, S i1 and ^{Z i1} is, ^M in the general formula (I) ^i1, M ^i2, and ^{L i1, L i2, P i1} , S i1 and ^{Z i1} each represent the same ^{meaning, S i4} and ^{P i4} the general formula (I) ^{S i2} and ^{P i2} in the same meaning, respectively,
^mia1 and ^mib1 represent 0, 1 or 2, ^mia2 and ^mib2 represent 0, 1 or 2, but ^mia1 + ^mia2 ≧ 1, and ^mib1 + ^mib2 ≧ 1. .. )
General formula (ia-1), general formula (ib-1), general formula (ia-2), general formula (ib-2), general formula (ia-3), general formula (ib-3), general formula In (ia-4) or the general formula (ib-4), X ^ia1 , X ^ia2 , X ^ia3 , X ^ia4 , X ^ia5 , X ^ia6 , X ^ia7 , X ^ib1 , X ^ib2 , X ^ib3 , X ^ib4 , X ^ib5. , X ^ib6 and X ^ib7 are independently substituted with hydrogen atom, halogen atom, cyano group, nitro group, fluorine atom, alkyl group having 1 to 8 carbon atoms, and carbon which may be substituted with fluorine atom, respectively. It is preferable to represent an alkoxy group having 1 to 8 atoms or −S ^i4- P ⁱ⁴ .

When Z ⁱ¹ in the general formula (ia-3), the general formula (ib-3), the general formula (ia-4) or the general formula (ib-4) represents a group other than −S ⁱ² −P ⁱ² , X ^ia1 , X ^ia2 , X ^ia3 , X ^ia4 , X ^ia5 , X ^ia6 , X ^ia7 , X ^ib1 , X ^ib2 , X ^ib3 , X ^ib4 , X ^ib5 , X ^ib6 and X ^ib7 It is preferable to represent S ^i4- P ⁱ⁴ . ^{Incidentally, M i1, M i2, L} i1, L i2, P i1, S i1, Z i1, S i4 and ^P preferred group is represented by formula of ^{i4 M} in ^{(I) i1, M i2,} L i1, L i2 , P ⁱ¹ , S ⁱ¹ , and Z ⁱ¹ .

The compound represented by the general formula (I) is preferably a compound represented by the general formula (II) from the viewpoint of having a sufficient pretilt angle and increasing the voltage holding ratio (VHR).

Compound represented by the general formula ^(II), the compound represented by the general formula is bound to a position ^{where X II6} is adjacent to the ^{X ii7} (iia) and ^{(if X II6} is substituted at the 2-position of naphthalene), It ^includes a compound represented by the general formula (iib) in which X ^{ii 6} binds to a position adjacent to X ^{ii 5} (when X ^{ii 6} is replaced with the 1-position of naphthalene).

^{(Wherein, M i1, L i1, S} i1, P i1 and ^{m i1} is the general formula ^(M i1 in ^{I), L i1, S i1} , P i1 and ^{m i1} represents the same meaning, respectively,
X ⁱⁱ¹ , X ⁱⁱ² , X ⁱⁱ³ , X ⁱⁱ⁴ , X ⁱⁱ⁵ , X ⁱⁱ⁶ and X ⁱⁱ⁷ are independently hydrogen atoms, halogen atoms, cyano groups, nitro groups or alkyl groups having 1 to 8 carbon atoms or formulas ( ii-Z)

When X ⁱⁱ¹ , X ⁱⁱ² , X ⁱⁱ³ , X ⁱⁱ⁴ , X ⁱⁱ⁵ , X ^{ii 6} or X ^{ii 7} represent an alkyl group, one −CH ₂ − or present in the alkyl group represents the group represented by. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. The hydrogen atom in the alkyl group may be replaced with a fluorine atom, provided that at least one of X ⁱⁱ¹ , X ⁱⁱ² , X ⁱⁱ³ , X ⁱⁱ⁴ , X ⁱⁱ⁵ , X ⁱⁱ⁶ and X ⁱⁱ⁷ . Represents a group represented by the formula (ii-Z).
M ^{ii2, L ii2} and ^{Z ii1} have the same meanings respectively as ^{M i2, L i2} and ^{Z i1} in formula (i-Z),
m ⁱⁱ² each represents 0, 1, or 2, provided ^that represents the ^m i1 ⁺ m ⁱⁱ² ≧ 1. )
X ⁱⁱ¹ , X ⁱⁱ² , X ⁱⁱ³ , X ⁱⁱ⁴ , X ⁱⁱ⁵ , X ⁱⁱ⁶ , X ⁱⁱ⁷ , M ⁱ¹ , M ⁱⁱ² , L ⁱ¹ , L in the general formula (II), the general formula (ia) and the general formula (iib). Preferred groups of ⁱⁱ² , Z ⁱⁱ¹ , S ⁱ¹ and P ⁱ¹ are X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ , X ⁱ⁷ , M ⁱ¹ , M ⁱ² , L in the general formula (I). ^{It is the same as i1} , ^Li2 , ^Zi1 , ^Si1 and ^Pi1 .

Since the maximum absorption wavelength of ultraviolet rays tends to shift to a long wavelength region as the number of rings increases, it is preferable in that it has a sufficient pretilt angle with a short ultraviolet irradiation time and the residual amount of the polymerizable compound is reduced.

Formula (II), in the general formula (iia) and the general formula ^{(iib), m ii1 + m} ii2 is preferably represents 1 or 2.

As the polymerizable compound represented by the general formula (I) according to the present invention, specifically, compounds represented by the general formulas (i-1) to (i-515) are preferable. Among the compounds represented by the general formulas (i-1) to (i-515), the general formulas (i-1) to (i-120) and the general formulas (i-161) to general formulas (i-161) to general formulas (i-120). i-193), general formulas (i-201) to general formulas (i-290) and general formulas (i-331) to general formulas (i-505) are preferable, and general formulas (i-1) to general formulas (i-1) to general formulas (i-1). i-12), general formula (i-18) to general formula (i-20), general formula (i-31) to general formula (i-42), general formula (i-48) to general formula (i-) 50), general formulas (i-161) to general formulas (i-173), general formulas (i-181) to general formulas (i-193), general formulas (i-201) to general formulas (i-220). , General formulas (i-231) to general formulas (i-250), and general formulas (i-331) to general formulas (i-505) are more preferable. When importance is attached to solubility, general formulas (i-1) to general formulas (i-12), general formulas (i-18) to general formulas (i-20), general formulas (i-31) to general formulas ( i-42), general formula (i-48) to general formula (i-50), general formula (i-201) to general formula (i-220) and general formula (i-231) to general formula (i-) 250) is preferable, and when the polymerization rate of the polymerizable compound is emphasized, general formulas (i-161) to (i-173), general formulas (i-181) to general formulas (i-193) and general formulas (i-193) are used. Formulas (i-331) to general formulas (i-505) are preferable.

The compound represented by the general formula (I) is the general formula (Im).

^(Wherein, M ^i1, L ^{i1, S i1} and ^{m i1} of the general formula (I) and ^{M i1,} L ^{i1, S} i1 and ^{m i1} in the same meaning, respectively,
X ^im1 , X ^im2 , X ^im3 , X ^im4 , X ^im5 , X ^im6 and X ^im7 are independently hydrogen atoms, halogen atoms, cyano groups, nitro groups or alkyl groups having 1 to 8 carbon atoms or formulas ( i-Zm)

^Represents a group represented by, and when X ^im1 , X ^im2 , X ^im3 , X ^im4 , X ^im5 , X ^im6 or X ^im7 represents an alkyl group, one −CH ₂ − or present in the alkyl group. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. may be replaced by, also, a hydrogen atom in the alkyl group may be substituted by a fluorine atom, provided ^{that, X im1, X im2, X} im3, X im4, at least one of X ^{im5, X im6} and ^{X IM7} One represents a group represented by the formula (i-Zm).
Y ^im1 and Y ^im2 independently represent a hydroxyl group, a protected hydroxyl group or a masked hydroxyl group, a halogen atom, a cyano group, a nitro group, ^-Pim2 or an alkyl group having 1 to 8 carbon atoms, and the alkyl group. one -CH ₂ present in the - or two or more -CH ² -, as the oxygen atoms are not directly adjacent, -O -, - CH = CH -, - C≡C -, - COO- , --OCO -, - may be replaced by CO- or -S-, also hydrogen atoms in the alkyl group may be replaced by fluorine atoms, provided ^that at least one hydroxyl group of ^{Y im1} or ^{Y im2} Represents a protected or masked hydroxyl group,
^Sim2 has the same meaning as ^Si1 and
P ^im2 has the same meaning as ^{P i1} of the general formula (I),
M ^{i2, L i2} and ^{m i2} have the same meanings respectively as ^{M i2, L i2} and ^{m i2} in formula (i-Z). )
It can be produced from the compound represented by.

The compound represented by the general formula (II) can be produced from the compound represented by the general formula (IIm).

Compound represented by the general formula (IIm) ^is the compound represented by the general formula that binds ^to a position ^{X Iim6} is adjacent to the ^{X iim7 (iiam) (if X Iim6} is substituted at the 2-position of naphthalene), X ^Iim6 encompasses a compound represented by the general formula (Iibm) that binds to a position adjacent to the ^{X iim5 (if X Iim6} is substituted at the 1-position of the naphthalene).

^{(Wherein, M i1, L i1, S} i1 and ^{m i1} represent the same meanings respectively as in the general formula ^(M i1 in ^II), L ^{i1, S} i1 and ^{m i1,}
X ^im1 , X ^im2 , X ^im3 , X ^im4 , X ^im5 , X ^im6 and X ^im7 are independently hydrogen atoms, halogen atoms, cyano groups, nitro groups or alkyl groups having 1 to 8 carbon atoms or formulas ( ii-Zm)

In represents a group represented ^{by, X iim1, X iim2, X} iim3, X iim4, X iim5, X iim6 or ^{if X Iim7} represents an alkyl group, one -CH ₂ present in the alkyl group -, or For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. may be replaced by, also, a hydrogen atom in the alkyl group may be substituted by a fluorine atom, provided ^{that, X iim1, X iim2, X} iim3, X iim4, at least one of ^{X iim5,} X iim6 and ^{X Iim7} One represents a group represented by the formula (ii-Zm).
Y ^im1 and Y ^im2 independently represent a hydroxyl group, a protected hydroxyl group or a masked hydroxyl group, a halogen atom, a cyano group, a nitro group, ^-Pim2 or an alkyl group having 1 to 8 carbon atoms, and the alkyl group. one -CH ₂ present in the - or two or more -CH ² -, as the oxygen atoms are not directly adjacent, -O -, - CH = CH -, - C≡C -, - COO- , -OCO-, -CO- or -S-, and the hydrogen atom in the alkyl group may be replaced with a fluorine atom, provided that at least one of ^Yim1 or ^Yim2 is a hydroxyl group. Represents a protected or masked hydroxyl group,
^Sim2 has the same meaning as S ⁱ¹
P ^IIM2 has the same meaning as ^{P i1} in formula (II),
M ^{ii2, L ii2} and ^{m ii2} each represent a same meaning as ^{M ii2, L} ii2 and ^{m ii2} in the formula (ii-Z). )
It can be produced from the compound represented by.

^X im1 in the general formula ^{(Im), X im2, X} im3, X im4, X im5, X im6, X im7, M i1, M i2, L i1, L i2, S i1, S im2, P im2, m Preferred groups of ⁱ¹ and ^mi2 are X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ , X ⁱ⁷ , M ⁱ¹ , M ⁱ² , L ⁱ¹ , L ⁱ² , S in the general formula (I). It is the same as the preferred groups of ⁱ¹ , S ⁱ² , ^Pi2 , ^mi1 and ^mi2 . In general formula (IIm), the general formula (iiam), ^X in the general formula ^{(iibm) iim1, X iim2,} X iim3, X iim4, X iim5, X iim6, X iim7, M i1, M ii2, L i1 ^{, L ii2, S i1, S} iim2, P iim2, preferred group of ^{m i1} and ^{m ii2} the general formula (II) in the ^{X ii1, X ii2, X ii3} , X ii4, X ii5, X ii6, X ii7 is the same as ^{M i1, M ii2, L i1} , L ii2, S i1, S i2, P i2, preferred group of ^{m i1} and ^{m ii2.}
The compound represented by the general formula (I-Np) can be produced from the compound represented by the general formula (I-Npm).

^{(Wherein, M i1, M i3, L} i1, S i1 and ^{q i1} are in the general formula ^{(I-Np) M i1,} M i3, L i1, each represents the same meaning as ^{S i1} and ^{q i1,}
X ^im1 , X ^im2 , X ^im3 , X ^im4 , X ^im5 , X ^im6 and X ^im7 are independently hydrogen atoms, halogen atoms, cyano groups, nitro groups or alkyl groups having 1 to 8 carbon atoms or formulas (i). -Zm)

^Represents a group represented by, and when X ^im1 , X ^im2 , X ^im3 , X ^im4 , X ^im5 , X ^im6 or X ^im7 represents an alkyl group, one −CH ₂ − or present in the alkyl group. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. may be replaced by, also, a hydrogen atom in the alkyl group may be substituted by a fluorine atom, provided ^{that, X im1, X im2, X} im3, X im4, at least one of X ^{im5, X im6} and ^{X IM7} One represents a group represented by the formula (i-Zm).
Y ^im1 and Y ^im2 independently represent a hydroxyl group, a protected hydroxyl group or a masked hydroxyl group, a halogen atom, a cyano group, a nitro group, ^-Pim2 or an alkyl group having 1 to 8 carbon atoms, and the alkyl group. one -CH ₂ present in the - or two or more -CH ² -, as the oxygen atoms are not directly adjacent, -O -, - CH = CH -, - C≡C -, - COO- , --OCO -, - may be replaced by CO- or -S-, also hydrogen atoms in the alkyl group may be replaced by fluorine atoms, provided ^that at least one hydroxyl group of ^{Y im1} or ^{Y im2} Represents a protected or masked hydroxyl group,
S ^im2 has the same meaning as ^{S i2} in formula (i-Z),
P ^im2 has the same meaning as ^{P i2} in formula (i-Z),
M ^{i2, L i2} and ^{m i2} represent the same meanings respectively as ^{M i2, L i2} and ^{m i2} in formula (i-Z),
^{M i1, M i2, L i1} , L i2, Z i1, S im2, S i3, P im2, or if ^{the P i3} there are a plurality, respectively, may have the same or different and
^Y im1 included in the general formula ^{(I-Npm), Y im2} , the total number of the number of ^{P im2} and ^{P i3} is 2 or 3. )
It can be produced from the compound represented by.

The compound represented by the general formula (i-Np-1) or the general formula (i-Np-2) is a compound represented by the general formula (i-Np-1m) or the general formula (i-Np-2m). Can be manufactured from.

^{(Wherein, M in1, M in3, L} in1, S in1, S in2 and ^{q in1} has the general formula (I-Np-1) or general formula (I-Np-2) in the ^{M in1, M in3,} L ^{in1, S in1,} respectively ^{S in2} and ^{q in1} the same meaning,
X in ^1m , X in ^2m , X in ^3m , X in ^4m , X in ^5m , X in ^6m and X in ^7m are independently hydrogen atoms, halogen atoms, cyano groups, nitro groups or alkyl groups having 1 to 8 carbon atoms or formulas ( i-nZm)

When X in 1 ^m , X in 2 ^m , X in 3 ^m , X in 4 ^m , X in 5 ^m , X in ^{6 m} or X in ^{7 m} represent an alkyl group, one −CH ₂ − or present in the alkyl group represents the group represented by. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. The hydrogen atom in the alkyl group may be replaced with a fluorine atom.
^Min2 , ^Lin2 and ^min2 have the same meanings as ^Min2 , ^Lin2 and the formula ^min2 in the general formula (I-Np-1) or the general formula (I-Np-2), respectively.
M ^{in4, L in4} and ^{m in4} have the same meanings respectively as ^{M in4, L in4} and ^{m in4} in formula (i-nZ),
Y ^im1 , Y ^{im 2} and Y ^im 4 independently represent a hydroxyl group, a protected hydroxyl group or a masked hydroxyl group, a halogen atom, a cyano group, a nitro group, −P ⁱⁿ⁴ or an alkyl group having 1 to 8 carbon atoms. one -CH ₂ present in the alkyl group -, or two or more -CH ² -, as the oxygen atoms are not directly adjacent, -O -, - CH = CH -, - C≡C-, It may be replaced with −COO−, −OCO−, −CO− or −S−, and the hydrogen atom in the alkyl group may be replaced with a fluorine atom, provided that at least one of ^Yim1 or ^Yim2 . One represents a hydroxyl group, a protected hydroxyl group or a masked hydroxyl group, and ^Sin4 and ^Pin4 have the same meanings as ^Sin4 and ^Pin4 in the formula ( ^inZ ), respectively.
^{M in1, M in2, M in4} , L in1, L in2, L in4, m in4, ^{if Z} in2, ^{S in4} and ^{P in4} there are a plurality, respectively, may have the same or different and
However, the general formula (i-Np-1m) or the general formula (i-Np-2m) contained in ^{Y iim1, Y iim2,} the total number of the number of ^{Y Iim4} and ^{P in4} is 2 or 3. )
General formula (Im), general formula (IIm), general formula (iima), general formula (iimb), general formula (I-Npm), general formula (i-Np-1m) or general formula (i-Np-2m) ), Y ^im1 , Y ^im2 , Y ^im1 , Y ^{im 2} or Y ^im 4 independently represent a hydroxyl group, a protected hydroxyl group or a masked hydroxyl group. The protected hydroxyl group or the masked hydroxyl group is not particularly limited as long as it is a known one obtained by converting a hydroxyl group into an inactive functional group, and for example, an ether type, an acetal type, an ester type, a silyl ether type and the like. Functional groups can be mentioned. More specifically, examples of the ether-based functional group include a methyl group, a benzyl group, and methoxymethyl. Further, examples of the acetal-based functional group include a tetrahydropyranyl group. Further, examples of the ester-based functional group include a formyl group and an acetyl group. Examples of the silyl ether-based functional group include a trimethylsilyl group and a t-butyldimethylsilyl group.

General formula (Im), general formula (IIm), general formula (iima), general formula (iimb), general formula (I-Npm), general formula (i-Np-1m) or general formula (i-Np-2m) The compound represented by) is, for example, a general formula (Im), a general formula (IIm), a general formula (iima), a general formula (iimb), a general formula (i-Np-1m) or a general formula (i-Np). and ^{Y im1, Y im2, Y iim1} , compound group represented by ^{Y IIM2} or ^{Y Iim4} represents a hydroxyl group in the compound represented by -2m), and the general formula (iiim)

(In the formula, ^{Pi 1} has the same meaning as ^{Pi 1} in the general formula (i), the general formula (ii) or the general formula (I-Np)).

Specifically, it can be produced by the following method.
(Production Method 1) Production of Compound Represented by General Formula (ia-3-1) In the presence of potassium carbonate and tetrakis (triphenylphosphine) palladium (0) in an ethanol solvent, 4-bromo-1-naphthol and the terminal are added. A phenylnaphthalene derivative (S-1) was obtained by Suzuki coupling with boric acid having a methoxy group, and then a dihydroxy compound (S-2) in which a methoxy group was converted into a phenolic hydroxyl group by hydrobromic acid in acetic acid was obtained. obtain. Further, the target compound (ia-3-1) can be obtained by a condensation reaction with diisopropylcarbodiimide using methacrylic acid in a dichloromethane solvent in the presence of dimethylaminopyridine.

^{(Wherein, M i1, M i2, L} i1, L i2, m i1 and ^{m i2} is ^M i1 in the general formula ^{(I), M i2, L} i1, L i2, the same meaning as ^{m i1} and ^{m i2} Represents.)
(Production Method 2) Production of Compound Represented by General Formula (ia-3-1) In the presence of pyridinium paratoluenesulfonate in a dichloromethane solvent, 4-bromo-1-naphthol and 3,4-dihydro-2H-pyran were added. The reaction was carried out to obtain a hydroxyl-protected substance (S-3) of naphthalene, and then Suzuki coupling with potassium carbonate and boric acid having a hydroxyl group at the terminal in the presence of tetrakis (triphenylphosphine) palladium (0) in an ethanol solvent. To obtain a phenylnaphthalene derivative (S-4) and further add an aqueous hydrochloric acid solution in THF to react to obtain a dihydroxy compound (S-2). Then, the target compound (ia-3-1) can be obtained by a condensation reaction with diisopropylcarbodiimide using methacrylic acid in a dichloromethane solvent in the presence of dimethylaminopyridine.

^{(Wherein, M i1, M i2, L} i1, L i2, m i1 and ^{m i2} is ^M i1 in the general formula ^{(I), M i2, L} i1, L i2, the same meaning as ^{m i1} and ^{m i2} Represents.)
(Production Method 3) Production of Compound Represented by General Formula (ia-3-2) From (S-4) to (S) by a condensation reaction with diisopropylcarbodiimide using methacrylic acid in the presence of dimethylaminopyridine in a dichloromethane solvent. -5) is obtained. Further, an aqueous hydrochloric acid solution is added to THF and reacted to obtain a hydroxy compound (S-6). Then, the target compound (ia-3-2) can be obtained by an esterification reaction using acrylic acid chloride in a dichloromethane solvent in the presence of diisopropylethylamine.

^{(Wherein, M i1, M i2, L} i1, L i2, m i1 and ^{m i2} is ^M i1 in the general formula ^{(I), M i2, L} i1, L i2, the same meaning as ^{m i1} and ^{m i2} Represents.)
(Liquid crystal composition)
When the compound represented by the general formula (I) is added for the liquid crystal composition, one or more compounds represented by the general formula (I) of the present invention may be added, and the general formula (I) In addition to the compound represented by I), a known polymerizable compound used in the liquid crystal composition, an antioxidant and the like may be further contained.

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

More specifically, in order to obtain a sufficient pretilt angle or a small residual amount of the polymerizable compound or a high voltage retention (VHR), the content is preferably 0.2 to 1.5% by mass, but precipitation at a low temperature. The content thereof is preferably 0.01 to 1.0% by mass when the suppression of the above is emphasized. When a plurality of polymerizable compounds represented by the general formula (I) are contained, the content of each is preferably 0.01 to 0.6% by mass. 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% by mass.

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

(Wherein, R ^L1 and R ^L2 represent each independently an alkyl group having 1 to 8 carbon atoms, one or non-adjacent two or more -CH 2 in the alkyl group _- is independently It may be replaced by −CH = CH−, −C≡C−, −O−, −CO−, −COO− or −OCO−.
n ^L1 represents 0, 1, 2 or 3
A ^{L1, A L2,} and ^{A L3} each independently (a) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - May be replaced with -O-) and (b) 1,4-phenylene group (one -CH = present in this group or two or more non-adjacent -CH = -N May be replaced with =)
(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 = existing in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent -CH = may be replaced with -N =. )
Represents a group selected from the group consisting of, and the above group (a), group (b) and group (c) may be independently substituted with a cyano group, a fluorine atom or a chlorine atom, respectively.
Z ^L1 and ^{Z L2} each independently represent a single _{bond, -CH 2 CH 2 -, -} (CH 2) 4 -, - OCH 2 -, - CH 2 O -, - COO -, - OCO -, - OCF 2 Represents −, −CF ₂ O−, −CH = NN = CH−, −CH = CH−, −CF = CF− or −C≡C−.
If n ^L1 is 2 or 3 and there are a plurality of A ^L2s , they may be the same or different, and if n ^L1 is 2 or 3 and there are a plurality of Z ^L3s , they may be the same or different. May be the same or different, except for the compounds represented by the general formulas (N-1), (N-2) and (N-3). )
The compound represented by the general formula (L) may be used alone, or may be used in combination. The types of compounds that can be combined are not particularly limited, but they are appropriately combined and used according to desired performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The type of compound used is, for example, one type as 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. More than a kind.

In the composition of the present invention, the content of the compound represented by the general formula (L) includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, seizure, and the like. It is necessary to make appropriate adjustments according to the required performance such as dielectric anisotropy.

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

When a composition having a low viscosity and a high response rate is required, it is preferable that the above lower limit value is high and the upper limit value is high. Further, when a composition having a high Tni of the composition of the present invention and good temperature stability is required, it is preferable that the above lower limit value is high and the upper limit value is high. Further, when it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable that the above lower limit value is low and the upper limit value is low.

Both ^RL1 and ^RL2 are preferably alkyl groups when reliability is important, and alkoxy groups are preferable when reducing the volatility of the compound is important, and reduction of viscosity is important. It is preferable that at least one of them is an alkenyl group.

The number of halogen atoms present in the molecule is preferably 0, 1, 2 or 3, preferably 0 or 1, and preferably 1 when compatibility with other liquid crystal molecules is important.

^RL1 and ^RL2 are linear alkyl groups having 1 to 5 carbon atoms and linear carbon atoms 1 to 4 when the ring structure to which they are bonded is a phenyl group (aromatic). The alkoxy group and the alkenyl group having 4 to 5 carbon atoms are preferable, and when the ring structure to which the alkoxy group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, the linear carbon atom number is 1 to 5. Alkyl groups, linear alkoxy groups having 1 to 4 carbon atoms and linear alkenyl groups having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

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

n ^L1 is preferably 0 when the response speed is important, 2 or 3 is preferable for improving the upper limit temperature of the nematic phase, and 1 is preferable for balancing these. Further, in order to satisfy the properties required for the composition, it is preferable to combine compounds having different values.

Preferably A ^L1, A ^L2, and A ^L3 if it is required to increase the Δn is aromatic, preferably to improve the response speed is an aliphatic, independently trans - 1,4-Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group , 1,4-Cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 It preferably represents a −diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, more preferably the following structure.

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

Z ^L1 and Z ^L2 are preferably single-bonded when response speed is important.

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

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

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

^{(Wherein, R L11} and ^{R L12} are each independently the same meaning as ^{R L1} and ^{R L2} in Formula (L).)
R ^L11 and ^RL12 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

The lower limit of the preferable content is 1%, 2%, 3%, 5%, 7%, 10%, and 15% based on the total amount of the composition of the present invention. %, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%. The preferred upper limit of the content is 95%, 90%, 85%, 80%, 75%, 70%, 65% with respect to the total amount of the composition of the present invention. %, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25%.

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

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

(In the formula, ^RL12 has the same meaning as in the general formula (L-1).)
The compound represented by the general formula (L-1-1) shall be a compound selected from the compound group represented by the formulas (L-1-1.1) to (L-1-1.3). Is preferable, and it is preferable that the compound is represented by the formula (L-1-1.2) or the formula (L-1-1.3), and in particular, the compound is represented by the formula (L-1-1.3). It is preferably a compound.

The lower limit of the preferable content of the compound represented by the formula (L-1-1.3) with respect to the total amount of the composition of the present invention is 1%, 2% and 3%. It is 5%, 7%, and 10%. The upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7%, and 6% with respect to the total amount of the composition of the present invention. %, 5%, and 3%.

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

(In the formula, ^RL12 has the same meaning as in the general formula (L-1).)
The lower limit of the preferable content of the compound represented by the formula (L-1-2) with respect to the total amount of the composition of the present invention is 1%, 5%, 10% and 15%. , 17%, 20%, 23%, 25%, 27%, 30%, 35%. The preferred upper limit of the content is 60%, 55%, 50%, 45%, 42%, 40%, 38, based on the total amount of the composition of the present invention. %, 35%, 33%, 30%.

Further, the compound represented by the general formula (L-1-2) is a compound selected from the compound group represented by the formulas (L-1-2.1) to (L-1-2.4). It is preferable that the compound is represented by the formulas (L-1-2.2) to (L-1-2.4). In particular, the compound represented by the formula (L-1-2.2) is preferable because it particularly improves the response rate of the composition of the present invention. Further, when obtaining Tni higher than the response speed, it is preferable to use a compound represented by the formula (L-1-2.3) or the formula (L1-2.4). The content of the compounds represented by the formulas (L-1-2.3) and (L-1-2.4) is not preferably 30% or more in order to improve the solubility at a low temperature.

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

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

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

(In the formula, ^RL13 and ^RL14 independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
As ^RL13 and ^RL14 , a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms is preferable.

The lower limit of the preferable content of the compound represented by the formula (L-1-3) with respect to the total amount of the composition of the present invention is 1%, 5%, 10% and 13%. , 15%, 17%, 20%, 23%, 25%, and 30%. The preferred upper limit of the content is 60%, 55%, 50%, 45%, 40%, 37%, 35% with respect to the total amount of the composition of the present invention. %, 33%, 30%, 27%, 25%, 23%, 20%, 17%, 15%, 13%, 10 %.
Further, 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). It is preferable that the compound is represented by the formula (L-1-3.1), the formula (L-1-3.3) or the formula (L-1-3.4). In particular, the compound represented by the formula (L-1-3.1) is preferable because it particularly improves the response rate of the composition of the present invention. 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-) are obtained. It is preferable to use the compound represented by 1-3.13). Total of compounds represented by formula (L-1-3.3), formula (L-1-3.4), formula (L-1-3.11) and 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 preferable content of the compound represented by the formula (L-1-3.1) with respect to the total amount of the composition of the present invention is 1%, 2% and 3%. It is 5%, 7%, 10%, 13%, 15%, 18%, and 20%. The upper limit of the preferable content is 20%, 17%, 15%, 13%, 10%, 8%, and 7% with respect to the total amount of the composition of the present invention. It is%, and it is 6%.

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

(In the formula, ^RL15 and ^RL16 independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
As ^RL15 and ^RL16 , a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms is preferable.

The lower limit of the preferable content of the compound represented by the formula (L-1-4) with respect to the total amount of the composition of the present invention is 1%, 5%, 10% and 13%. It is 15%, it is 17%, and it is 20%. The upper limit of the preferable content is 25%, 23%, 20%, 17%, 15%, 13%, and 10% with respect to the total amount of the composition of the present invention. %.

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

Further, the compounds represented by the general formulas (L-1-4) and (L-1-5) are represented by the formulas (L-1-5.3) from the formulas (L-1-4.1). It is preferable that the compound is selected from the above-mentioned compound group, and the compound represented by the formula (L-1-4.2) or the formula (L-1-5.2) is preferable.

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

Equation (L-1-1.3), Equation (L-1-2.2), Equation (L-1-3.1), Equation (L-1-3.3), Equation (L-1- It is preferable to combine two or more compounds selected from the compounds represented by 3.4), the formula (L-1-3.11) and the formula (L-1-3.12), and the 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 the formula (L-1-4.2), and the lower limit of the preferable content of the total content of these compounds is the composition of the present invention. 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, etc. , 20%, 23%, 25%, 27%, 30%, 33%, 35%, and the upper limit is relative to the total amount of the composition of the present invention. , 80%, 70%, 60%, 50%, 45%, 40%, 37%, 35%, 33%, 30%. , 28%, 25%, 23%, 20%. When the reliability of the composition is emphasized, the compounds represented by the formulas (L-1-3.1), (L-1-3.3) and (L-1-3.4) are used. It is preferable to combine two or more selected compounds, and when the response speed of the composition is important, it is represented by the formulas (L-1-1.3) and (L-1-2.2). It is preferable to combine two or more compounds selected from the compounds.
The compound represented by the general formula (L-1) is preferably a compound selected from the compound group represented by the general formula (L-1-6).

(In the formula, ^RL17 and ^RL18 each independently represent a methyl group or a hydrogen atom.)
The lower limit of the preferable content of the compound represented by the formula (L-1-6) with respect to the total amount of the composition of the present invention is 1%, 5%, 10% and 15%. , 17%, 20%, 23%, 25%, 27%, 30%, 35%. The preferred upper limit of the content is 60%, 55%, 50%, 45%, 42%, 40%, 38, based on the total amount of the composition of the present invention. %, 35%, 33%, 30%.

Further, 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). It is preferable to have.

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

^{(Wherein, R L21} and ^{R L22} are each independently the same meaning as ^{R L1} and ^{R L2} in Formula (L).)
^RL21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and ^RL22 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the solubility at low temperature is emphasized, the effect is high when the content is set high, and conversely, when the response speed is emphasized, the effect is high when the content is set low. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (L-2) is preferably a compound selected from the compound group represented by the formulas (L-2.1) to (L-2.6), preferably the formula. It is preferably a compound represented by (L-2.1), formula (L-2.3), formula (L-2.4) and formula (L-2.6).

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

^{(Wherein, R L31} and ^{R L32} are each independently the same meaning as ^{R L1} and ^{R L2} in Formula (L).)
^RL31 and ^RL32 are preferably alkyl groups having 1 to 5 carbon atoms, alkenyl groups having 4 to 5 carbon atoms, or alkoxy groups having 1 to 4 carbon atoms, respectively.

The compound represented by the general formula (L-3) can be used alone, or two or more compounds can be used in combination. The types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

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

When a high birefringence is obtained, the effect is high when the content is set high, and conversely, when high Tni is emphasized, the effect is high when the content is set low. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

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

^{(Wherein, R L41} and ^{R L42} are each independently the same meaning as ^{R L1} and ^{R L2} in Formula (L).)
^RL41 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and ^RL42 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

In the composition of the present invention, the content of the compound represented by the general formula (L-4) includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dropping marks, and the like. It is necessary to make appropriate adjustments according to the required performance such as seizure and dielectric anisotropy.

The lower limit of the preferable content of the compound represented by the formula (L-4) with respect to the total amount of the composition of the present invention is 1%, 2%, 3% and 5%. , 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%. .. The upper limit of the preferable content of the compound represented by the formula (L-4) with respect to the total amount of the composition of the present invention is 50%, 40%, 35%, and 30%. , 20%, 15%, 10%, 5%.

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

Depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc., even if the compound represented by the formula (L-4.1) is contained, the formula (L) Even if it contains the compound represented by 4.2), it contains both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2). It may contain all the compounds represented by the formulas (L-4.1) to (L-4.3). The lower limit of the preferable content of the compound represented by the formula (L-4.1) or the formula (L-4.2) with respect to the total amount of the composition of the present invention is 3%, which is 5%. Yes, 7%, 9%, 11%, 12%, 13%, 18%, 21%, and 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-4.1) and the compound represented by the formula (L-4.2) are contained, both compounds are used with respect to the total amount of the composition of the present invention. The lower limit of the preferred content is 15%, 19%, 24%, 30%, and the preferred upper limit is 45, 40%, 35%, 30%. Yes, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (L-4) is preferably a compound represented by the formulas (L-4.4) to (L-4.6), for example, preferably the compound represented by the formula (L-4.4). ) Is preferable.

Depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc., even if the compound represented by the formula (L-4.4) is contained, the formula (L) Even if it contains the compound represented by −4.5), it contains both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5). You may be.

The lower limit of the preferable content of the compound represented by the formula (L-4.4) or the formula (L-4.5) with respect to the total amount of the composition of the present invention is 3%, which is 5%. Yes, 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, both compounds are used with respect to the total amount of the composition of the present invention. The lower limit of the preferred content is 15%, 19%, 24%, 30%, and the preferred upper limit is 45, 40%, 35%, 30%. Yes, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (L-4) is preferably a compound represented by the formulas (L-4.7) to (L-4.10), and in particular, 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.

^{(Wherein, R L51} and ^{R L52} are each independently the same meaning as ^{R L1} and ^{R L2} in Formula (L).)
^RL51 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and ^RL52 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

In the composition of the present invention, the content of the compound represented by the general formula (L-5) includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dropping marks, and the like. It is necessary to make appropriate adjustments according to the required performance such as seizure and dielectric anisotropy.

The lower limit of the preferable content of the compound represented by the formula (L-5) with respect to the total amount of the composition of the present invention is 1%, 2%, 3% and 5%. , 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40%. .. The upper limit of the preferable content of the compound represented by the formula (L-5) with respect to the total amount of the composition of the present invention is 50%, 40%, 35%, and 30%. , 20%, 15%, 10%, 5% The compounds represented by the general formula (L-5) are of the formula (L-5.1) or the formula (L-5.2). ) Is preferable, and a compound represented by the formula (L-5.1) is particularly preferable.

The lower limit of the preferable content of these compounds with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% and 7%. The upper limit of the preferable content of these compounds is 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) or the formula (L-5.4).

The lower limit of the preferable content of these compounds with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% and 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.

The compound represented by the general formula (L-5) is preferably a compound selected from the compound group represented by the formulas (L-5.5) to (L-5.7), and particularly the compound represented by the formula (L-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 composition of the present invention is 1%, 2%, 3%, 5% and 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.

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

^{(Wherein, R L61} and ^{R L62} each independently represent the same meaning as ^{R L1} and ^{R L2} in Formula ^{(L), X L61} and ^{X L62} each independently represents a hydrogen atom or a fluorine atom. )
R ^L61 and ^RL62 are preferably alkyl groups having 1 to 5 carbon atoms or alkenyl groups having 2 to 5 carbon atoms independently, and one of ^XL61 and ^XL62 is a fluorine atom and the other is a hydrogen atom. Is preferable.

The compound represented by the general formula (L-6) may be used alone, or may be used in combination of two or more compounds. The types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

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

The compound represented by the general formula (L-6) is preferably a compound represented by the formulas (L-6.1) to (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 even more preferably 1 to 4 types. Further, since the wide molecular weight distribution of the selected compound is also effective for solubility, for example, one kind from the compounds represented by the formula (L-6.1) or (L-6.2), the formula (L-). One type from the compound represented by 6.4) or (L-6.5), one type from the compound represented by the formula (L-6.6) or the formula (L-6.7), one type from the compound represented by the formula (L-6.7), the formula (L). It is preferable to select one kind of compound from the compounds represented by −6.8) or (L-6.9) and combine these appropriately. Among them, it is represented by the formula (L-6.1), the formula (L-6.3), the formula (L-6.4), the formula (L-6.6) and the formula (L-6.9). It preferably contains a compound.

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

The lower limit of the preferable content of these compounds with respect to the total amount of the composition of the present invention is 1%, 2%, 3%, 5% and 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, and 9%.

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

^{(Wherein, R L71} and ^{R L72} each independently represent the same meaning as ^{R L1} and ^{R L2} in Formula ^{(L), A L71} and ^{A L72} is ^{A L2} and in the general formula (L) independently Although it has the same meaning as A ^L3 , the hydrogen atoms on A ^L71 and A ^L72 may be independently substituted with fluorine atoms, and Z ^L71 has the same meaning as Z ^L2 in the general formula (L). X ^L71 and X ^L72 independently represent a fluorine atom or a hydrogen atom.)
In the formula, ^RL71 and ^RL72 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 ^AL71 and ^AL72. Is preferably a 1,4-cyclohexylene group or a 1,4-phenylene group independently, and the hydrogen atom on ^AL71 and ^AL72 may be independently substituted with a fluorine atom, and Z ^L71 is ^simply. Bonds or -COO- are preferred, single bonds are preferred, and ^XL71 and ^XL72 are preferably hydrogen atoms.

The types of compounds that can be combined are not particularly limited, but they are combined 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, two types, three types, and four types as one embodiment of the present invention.

In the composition of the present invention, the content of the compound represented by the general formula (L-7) includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dropping marks, and the like. It is necessary to make appropriate adjustments according to the required performance such as seizure and dielectric anisotropy.

The lower limit of the preferable content of the compound represented by the formula (L-7) with respect to the total amount of the composition of the present invention is 1%, 2%, 3% and 5%. , 7%, 10%, 14%, 16%, 20%. The upper limit of the preferable content of the compound represented by the formula (L-7) with respect to the total amount of the composition of the present invention is 30%, 25%, 23%, and 20%. , 18%, 15%, 10%, 5%.

When an embodiment of Tni having a high composition of the present invention is desired, it is preferable to increase the content of the compound represented by the formula (L-7), and when an embodiment having a low viscosity is desired, the content is high. It is preferable to reduce the amount.

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulas (L-7.1) to (L-7.4), and the compound represented by the formula (L-7. It is preferably a compound represented by 2).

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulas (L-7.11) to (L-7.13), and the compound represented by the formula (L-7. It is preferably a compound represented by 11).

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

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulas (L-7.31) to (L-7.34), and the compound represented by the formula (L-7. It is preferably a compound represented by 31) or / and the formula (L-7.32).

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulas (L-7.41) to (L-7.44), and the compound represented by the formula (L-7. It is preferably a compound represented by 41) or / and the formula (L-7.42).

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

The composition of the present invention preferably contains one or more compounds selected from the compounds represented by the general formulas (N-1), (N-2) and (N-3). These compounds are dielectrically negative compounds (the sign of Δε is negative and their absolute value is greater than 2).

(In the formula, ^RN11 , ^RN12 , ^RN21 , ^RN22 , ^RN31 and ^RN32 each independently represent an alkyl group having 1 to 8 carbon atoms, and one of the alkyl groups or two non-adjacent ones. More than one −CH ₂₋ may be independently 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 independently (a) 1,4-cyclohexylene groups (one -CH _2- or adjacent to each other in this group). no more than one -CH ₂ - may be replaced by -O-),.
(B) A 1,4-phenylene group (one -CH = existing in this group or two or more non-adjacent -CH = 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 = existing in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent -CH = may be replaced with -N =. ) And (d) represent a group selected from the group consisting of 1,4-cyclohexenylene groups, and the above groups (a), group (b), group (c) and group (d) are independently cyano. It may be substituted with a group, 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-
X ^N21 represents a hydrogen atom or a fluorine atom.
^TN31 represents −CH _2- or oxygen atom,
n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, but n ^N11 + n ^N12 , n ^N21 + n ^N22 and n ^N31 + n ^N32 are independent of each other. When it is 1, 2 or 3, and 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 of more than 3.

In the general formulas (N-1), (N-2) and (N-3), ^RN11 , ^RN12 , ^RN21 , ^RN22 , ^RN31 and ^RN32 are independent of each other and have 1 to 8 carbon atoms. Alkyl group, alkoxy group having 1 to 8 carbon atoms, alkenyl group having 2 to 8 carbon atoms or alkenyloxy group having 2 to 8 carbon atoms is preferable, and the alkyl group having 1 to 5 carbon atoms and the number of carbon atoms are preferable. An alkoxy group having 1 to 5 atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferable. More preferably, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is further preferable, and an alkenyl group (propenyl group) having 3 carbon atoms is particularly preferable.

When the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and carbon are used. An alkoxy group having 4 to 5 atoms is preferable, and when the ring structure to which the alkoxy group is bonded is a saturated ring structure such as cyclohexane, pyran, or dioxane, a linear alkyl group having 1 to 5 carbon atoms or a linear chain is used. Alkoxy groups having 1 to 4 carbon atoms and linear alkenyl groups having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

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

A ^N11 , ^AN12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are preferably aromatics when it is required to increase Δn independently, and fats are used to improve the response rate. It is preferably a group, and is preferably a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, 3,5. -Difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1 , 4-Diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, which are preferably represented as follows. It is more preferable to represent the structure of

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

^{Z N11, Z N12, Z N21} , Z N22, Z N31 and ^{Z N32} _-CH 2 each _{independently O -, - CF 2 O -} , - CH 2 CH 2 -, - CF 2 CF 2 - or a single bond preferably represents _{an, -CH 2 O -, - CH} 2 CH 2 - or a single bond is more preferable, _-CH 2 O-or a single bond is particularly preferred.

Fluorine atom is preferable for X ^N21 .

Oxygen atom is preferable for ^TN31 .

n ^N11 + n ^N12 , n ^N21 + n ^N22 and n ^N31 + n ^N32 are preferably 1 or 2, n ^N11 is 1 and n ^N12 is 0, n ^N11 is 2 and n ^N12 is 0, n ^{The combination of N11} being 1 and ^nN12 being 1, the combination of ^nN11 being 2 and ^nN12 being 1, the combination of ^nN21 being 1 and ^nN22 being 0, ^nN21 being 2 and ^nN22 being A combination of 0, a combination of n ^N31 of 1 and n ^N32 of 0, and a combination of n ^N31 of 2 and n ^N32 of 0 are preferred.

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

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

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

When a composition having a low viscosity and a high response rate is required, it is preferable that the above lower limit value is low and the upper limit value is low. Further, when a composition having a high Tni of the composition of the present invention and good temperature stability is required, it is preferable that the above 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 drive voltage low, it is preferable that the above lower limit value is high and the upper limit value is high.

Examples of the compound represented by the general formula (N-1) include a group of 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 ^Represents 0 or 1, n ^Nd11 represents 1 or 2, n ^Ne11 represents 1 or 2, n ^Nf12 represents 1 or 2, n ^{Ng 11} represents 1 or 2, and A ^{Ne 11} represents trans-1,4. ^{-Represents a} cyclohexylene group or a 1,4-phenylene group, and A ^Ng11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group, but at least one. ^{Represents a} 1,4-cyclohexenylene group, Z ^Ne11 represents a single bond or ethylene, but at least one present in the molecule represents ethylene, and multiple A ^Ne11 , Z ^Ne11 , and / or present in the molecule. A ^{Ng 11} may be the same or different.)
More specifically, the compound represented by the general formula (N-1) may be a compound selected from the compound group represented by the general formulas (N-1-1) to (N-1-22). preferable.

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

^{(Wherein, R N111} and ^{R N112} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN111 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, a pentyl group or a vinyl group. ^RN112 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set low. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (N-1-1) is a compound selected from the compound group represented by the formulas (N-1-1.1) to (N-1-1.25). It is preferable that the compound is represented by the formulas (N-1-1.1) to (N-1-1.4), and the formulas (N-1-1.1) and the formula (N-1-1.4) are preferable. The compound represented by -1-1.3) is preferable.

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

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

^{(Wherein, R N121} and ^{R N122} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN121 is 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, a butyl group or a pentyl group. The ^RN122 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set low, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (N-1-2) is a compound selected from the compound group represented by the formulas (N-1-2.1) to (N-1-2.25). It is preferable that there are formulas (N-1-2.3) to formulas (N-1-2.7), formulas (N1-2.10), formulas (N-1-2.11), and formulas. It is preferably a compound represented by (N-1-2.13) and the formula (N1-2.20), and when the improvement of Δε is emphasized, the formula (N-1-2.3) is used. is preferably a compound represented by the formula (N-1-2.7) _from when emphasizing improvements in _{T NI} formula (N-1-2.10), formula (N-1-2.11) And the compound represented by the formula (N-1-2.13) is preferable, and the compound represented by the formula (N-1-2.20) is used when the improvement of the response speed is emphasized. Is preferable.

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

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

^{(Wherein, R N131} and ^{R N132} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. ^RN132 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (N-1--3) is a compound selected from the compound group represented by the formulas (N-1-3.21) to (N-1-3.21). It is preferable that the compound is represented by the formulas (N-1-3.1) to (N-1-3.7) and (N-1-3.21), and is preferably the compound represented by the formula (N-1-3.21). -1-3.1), Eq. (N-1-3.2), Eq. (N-1-3.3), Eq. (N-1-3.4) and Eq. (N-1-3.6) ) Is preferable.

The compounds represented by the formulas (N-1-3.1) to (N-1-3.4), the formula (N-1-3.6) and the formula (N-1-3.21) are independent. It can be used in the above or in combination, but it is a combination of the formulas (N-1-3.1) and (N-1-3.2) and the formula (N-1-3.3). ), Formula (N-1-3.4) and formula (N-1-3.6), 2 or 3 combinations are preferred. The lower limit of the preferred content of the composition alone or of these compounds relative to the total amount of the compositions of the present invention is 5%, 10%, 13%, 15%, 17%, 20 %. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 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).)
Independently R ^N141 and ^{R N142} are each an alkyl group having 1 to 5 carbon atoms, preferably an alkenyl group or an alkoxy group having 1 to 4 carbon atoms carbon atoms 4-5, methyl group, propyl group, ethoxy A group or a butoxy group is preferable.

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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set low. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (N-1--4) is a compound selected from the compound group represented by the formulas (N-1-4.2) to (N-1-4.24). It is preferable that the compound is represented by the formulas (N-1-4.1) to (N-1-4.4), and the compounds are preferably of the formulas (N-1-4.1) and (N-1-4.4). The compounds represented by -1-4.2) and the formula (N-1-4.4) are preferable.

The compounds represented by the formulas (N-1-4.1) to (N-1-4.24) can be used alone or in combination, but the composition of the present invention can be used. The lower limit of the preferred content of these compounds alone or of these compounds relative to the total amount is 3%, 5%, 7%, 10%, 13%, 15%, 17%. It is 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 13%, 11%, 10%, 8%.

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

^{(Wherein, R N151} and ^{R N152} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
Each of ^RN151 and ^RN152 is 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 preferable.

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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set low, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (N-1-5) is a compound selected from the compound group represented by the formulas (N-1-5.1) to (N-1-5.12). It is preferable that the compound is represented by the formula (N-1-5.1), the formula (N-1-5.2) and the formula (N-1-5.4).

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

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

^{(Wherein, R N1101} and ^{R N1102} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1101 is 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, a butyl group, a vinyl group or a 1-propenyl group. ^RN1102 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set low. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (N-1-10) is a compound selected from the compound group represented by the formulas (N-1-10.14) to (N-110.14). It is preferable that the compound is represented by the formulas (N-1-10.1) to (N-1-10.5), and the compounds are preferably represented by the formulas (N-1-10.1) to (N-1-10.5). The compound represented by 1-10.2) is preferable.

The compounds represented by the formulas (N-1-10.1) and (N-1-10.2) can be used alone or in combination, but the compositions of the present invention can be used. The lower limit of the preferred content of these compounds alone or of these compounds relative to the total amount of is 5%, 10%, 13%, 15%, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 13%.

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

^{(Wherein, R N1111} and ^{R N1112} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1111 is 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, a butyl group, a vinyl group or a 1-propenyl group. ^RN1112 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set low, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (N-1-11) is a compound selected from the compound group represented by the formulas (N-1-11.1) to (N-1-1.14). It is preferable that the compound is represented by the formulas (N-1-11.1) to (N-1-1.14), and the formulas (N-1-11.2) and the formula (N-N-1-11.2) are preferable. The compound represented by 1-11.4) is preferable.

The compounds represented by the formulas (N-1-11.2) and (N-1-11.4) can be used alone or in combination, but the compositions of the present invention can be used. The lower limit of the preferred content of these compounds alone or of these compounds relative to the total amount of is 5%, 10%, 13%, 15%, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 13%.

The compound represented by the general formula (N-1-12) is the following compound.

^{(Wherein, R N1121} and ^{R N1122} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. ^RN1122 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set low. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

The compound represented by the general formula (N-1-13) is the following compound.

^{(Wherein, R N1131} and ^{R N1132} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. ^RN1132 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

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

^{(Wherein, R N1141} and ^{R N1142} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. ^RN1142 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 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set low. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

The compound represented by the general formula (N-1-15) is the following compound.

^{(Wherein, R N1151} and ^{R N1152} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1151 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. ^RN1152 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 preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-15) can be used alone, or two or more compounds can be used in combination. The types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

The compound represented by the general formula (N-1-16) is the following compound.

^{(Wherein, R N1161} and ^{R N1162} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1161 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. ^RN1162 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 preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-16) can be used alone, or two or more compounds can be used in combination. The types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

The lower limit of the preferable content of the compound represented by the formula (N-1-16) with respect to the total amount of the composition of the present invention is 5%, 10%, 13% and 15%. It is 17% and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 13%.

The compound represented by the general formula (N-1-17) is the following compound.

^{(Wherein, R N1171} and ^{R N1172} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1171 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. ^RN1172 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 preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-17) can be used alone, or two or more compounds can be used in combination. The types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

The compound represented by the general formula (N-1-18) is the following compound.

^{(Wherein, R N1181} and ^{R N1182} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1181 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. ^RN1182 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 preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-18) can be used alone, or two or more compounds can be used in combination. The types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

Further, the compound represented by the general formula (N-1-18) is a compound selected from the compound group represented by the formulas (N-1-18.1) to (N-1-18.5). It is preferable that the compound is represented by the formulas (N-1-18.1) to (N-1-11.3), and the compounds are preferably represented by the formulas (N-1-18.2) and (N-1-11.3). The compound represented by 1-18.3) is preferable.

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

^{(Wherein, R N1201} and ^{R N1202} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1201 and ^RN1202 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

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

^{(Wherein, R N1211} and ^{R N1212} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1211 and ^RN1212 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

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

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

^{(Wherein, R N1221} and ^{R N1222} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN1221 and ^RN1222 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, 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 types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

The lower limit of the preferable content of the compound represented by the formula (N-2-1) with respect to the total amount of the composition of the present invention is 1%, 5%, 10% and 13%. It is 15%, it is 17%, and it is 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, 13%, 10%, 5%.

Further, the compound represented by the general formula (N-1-22) is a compound selected from the compound group represented by the formulas (N-1-22.1) to (N-1-2.12.2). It is preferable that the compound is represented by the formulas (N-1-22.1) to (N-1-22.5), and the compounds are preferably represented by the formulas (N-1-22.1) to (N-). The compound represented by 1-22.4) is preferable.

The compound represented by the general formula (N-3) is preferably a compound selected from the compound group represented by the general formula (N-3-2).

^{(Wherein, R N321} and ^{R N322} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-3).)
^RN321 and ^RN322 are 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 or a pentyl group.

The compound represented by the general formula (N-3-2) can be used alone, or two or more compounds can be used in combination. The types 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, two types, three types, four types, and five or more types as one embodiment of the present invention.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when is set high. Further, when improving the dripping marks and the seizure characteristics, it is preferable to set the content range in the middle.

The lower limit of the preferable content of the compound represented by the formula (N-3-2) with respect to the total amount of the composition of the present invention is 3%, 5%, 10% and 13%. , 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%. The preferred upper limit of the content is 50%, 40%, 38%, 35%, 33%, 30%, 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 % And 5%.

Further, the compound represented by the general formula (N-3-2) is a compound selected from the compound group represented by the formulas (N-3-2.1) to (N-3-2.3). It is preferable to have.

The composition of the present invention preferably contains one or more compounds represented by the general formula (J). These compounds are dielectrically positive compounds (Δε is greater than 2).

(In the formula, R ^J1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent −CH ₂ − in the alkyl group are independently −CH = CH−, −. It may be replaced by C≡C−, −O−, −CO−, −COO− or −OCO−.
n ^J1 represents 0, 1, 2, 3 or 4
A ^J1 , A ^J2 and A ^J3 are independent of each other.
(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 = existing in this group or two or more -CH = not adjacent to each other may be replaced with -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) , 3,4-Tetrahydronaphthalene-2,6-Diyl One -CH = present in the group or two or more non-adjacent -CH = may be replaced with -N =).
Represents a group selected from the group consisting of, and the above groups (a), group (b) and group (c) are independently cyano groups, fluorine atoms, chlorine atoms, methyl groups, trifluoromethyl groups or trifluoro groups. It may be substituted with a methoxy group,
Z ^J1 and ^{Z J2} each independently represent a single _{bond, -CH 2 CH 2 -, -} (CH 2) 4 -, - OCH 2 -, - CH 2 O -, - OCF 2 -, - CF 2 O-, Represents -COO-, -OCO- or -C≡C-
When n ^J1 is 2, 3 or 4 and there are a plurality of A ^J2s , they may be the same or different, and when n ^J1 is 2, 3 or 4 and there are a plurality of Z ^J1s. If so, they may be the same or different,
^XJ1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a 2,2,2-trifluoroethyl group. )
In the general formula ^{(J), R J1} is an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, alkenyloxy of alkenyl or 2 to 8 carbon atoms having from 2 to 8 carbon atoms The group is preferable, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable. Alkyl groups having 1 to 5 or alkenyl groups having 2 to 5 carbon atoms are more preferable, alkyl groups having 2 to 5 carbon atoms or alkenyl groups having 2 to 3 carbon atoms are further preferable, and alkenyl groups having 3 carbon atoms are more preferable. (Propenyl group) is particularly preferable.

Preferably R ^J1 is an alkyl group in the case of emphasizing reliability, it is preferred when emphasizing a reduction in viscosity is an alkenyl group.

When the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and carbon are used. An alkoxy group having 4 to 5 atoms is preferable, and when the ring structure to which the alkoxy group is bonded is a saturated ring structure such as cyclohexane, pyran, or dioxane, a linear alkyl group having 1 to 5 carbon atoms or a linear chain is used. Alkoxy groups having 1 to 4 carbon atoms and linear alkenyl groups having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

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

A ^J1 , A ^J2 and A ^J3 are preferably aromatic when it is required to increase Δn independently, and are preferably aliphatic in order to improve the response rate, and trans-. 1,4-Cyclohexylene group, 1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene It preferably represents a -2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, which are substituted with fluorine atoms. It may be more preferable to represent the following structure.

It is more preferable to represent the following structure.

Z ^J1 and Z ^J2 independently represent -CH ₂ O-, -OCH _2- , -CF ₂ O-, -CH ₂ CH _2- , -CF ₂ CF _2- or single bond, respectively. OCH _2- , -CF ₂ O-, -CH ₂ CH _2- or single bond is more preferred, and -OCH _2- , -CF ₂ O- or single bond is particularly preferred.

^XJ1 is preferably a fluorine atom or a trifluoromethoxy group, preferably a fluorine atom.

n ^J1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, 0 or 1 is preferable in the case of focusing on improvement of [Delta] _[epsilon], in the case of emphasizing _{T NI} 1 or 2 preferable.

The types of compounds that can be combined are not particularly limited, but they are used in combination according to desired performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, two types, and three types as one embodiment of the present invention. Furthermore, in another embodiment of the present invention, there are four types, five types, six types, and seven or more types.

In the composition of the present invention, the content of the compound represented by the general formula (J) includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, seizure, and the like. It is necessary to make appropriate adjustments according to the required performance such as dielectric anisotropy.

The lower limit of the preferable content of the compound represented by the general formula (J) with respect to the total amount of the composition of the present invention is 1%, 10%, 20%, and 30%. It is 40%, 50%, 55%, 60%, 65%, 70%, 75%, and 80%. The preferred upper limit of the content is, for example, 95%, 85%, 75%, 65%, 55% in one embodiment of the invention, relative to the total amount of the composition of the invention. Yes, 45%, 35%, 25%.

When a composition having a low viscosity and a high response rate is required, it is preferable to lower the lower limit value and lower the upper limit value. Further, when the _TNI of the composition of the present invention is kept high and a composition having good temperature stability is required, it is preferable to lower the lower limit value and lower the upper limit value. Further, when it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable to raise the above lower limit value and raise the upper limit value.

Preferably R ^J1 is an alkyl group in the case of emphasizing reliability, it is preferred when emphasizing a reduction in viscosity is an alkenyl group.

As the compound represented by the general formula (J), the compound represented by the general formula (M) is preferable.

The composition of the present invention preferably contains one or more compounds represented by the general formula (M). These compounds are dielectrically positive compounds (Δε is greater than 2).

^{(Wherein, R M1} represents an alkyl group having 1 to 8 carbon atoms, one or non-adjacent two or more -CH ₂ in the alkyl group - are each independently -CH = CH -, - It may be replaced by C≡C−, −O−, −CO−, −COO− or −OCO−.
n ^M1 represents 0, 1, 2, 3 or 4
^AM1 and ^AM2 are independent of each other
(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- or -S- (May be) and (b) 1,4-phenylene group (one -CH = existing in this 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, and the hydrogen atoms on the above groups (a) and (b) may be independently substituted with cyano groups, fluorine atoms or chlorine atoms, respectively.
Z ^M1 and ^{Z M2} each independently represent a single _{bond, -CH 2 CH 2 -, -} (CH 2) 4 -, - OCH 2 -, - CH 2 O -, - OCF 2 -, - CF 2 O-, Represents −COO−, −OCO− or −C≡C−
When n ^M1 is 2, 3 or 4 and there are a plurality of ^AM2 , they may be the same or different, and when n ^M1 is 2, 3 or 4 and there are a plurality of Z ^M1s. If so, they may be the same or different,
X ^M1 and X ^M3 independently represent a hydrogen atom, a chlorine atom or a fluorine atom, respectively.
X ^M2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a 2,2,2-trifluoroethyl group.

In the general formula (M), ^RM1 is an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy having 2 to 8 carbon atoms. The group is preferable, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferable. Alkyl groups having 1 to 5 or alkenyl groups having 2 to 5 carbon atoms are more preferable, alkyl groups having 2 to 5 carbon atoms or alkenyl groups having 2 to 3 carbon atoms are further preferable, and alkenyl groups having 3 carbon atoms are more preferable. (Propenyl group) is particularly preferable.

Preferably R ^M1 is an alkyl group in the case of emphasizing reliability, it is preferred when emphasizing a reduction in viscosity is an alkenyl group.

When the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and carbon are used. An alkoxy group having 4 to 5 atoms is preferable, and when the ring structure to which the alkoxy group is bonded is a saturated ring structure such as cyclohexane, pyran, or dioxane, a linear alkyl group having 1 to 5 carbon atoms or a linear chain is used. Alkoxy groups having 1 to 4 carbon atoms and linear alkenyl groups having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

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

Preferably when it is desired A ^M1 and A ^M2 is to increase the Δn each independently is an aromatic, preferably to improve the response speed is an aliphatic, trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2, 3-Difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It is preferable to represent a diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably to represent the following structure.

It is more preferable to represent the following structure.

Z ^M1 and ^{Z M2} each _{independently -CH 2 O -, - CF 2} O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, _-CF 2 O-, -CH ₂ CH _2- or single bond is more preferred, and -CF ₂ O- or single bond is particularly preferred.

n ^M1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, 0 or 1 is preferable in the case of focusing on improvement of [Delta] _[epsilon], in the case of emphasizing _{T NI} 1 or 2 preferable.

The types of compounds that can be combined are not particularly limited, but they are used in combination according to desired performance such as solubility at low temperature, transition temperature, electrical reliability, and birefringence. The types of compounds used are, for example, one type, two types, and three types as one embodiment of the present invention. Furthermore, in another embodiment of the present invention, there are four types, five types, six types, and seven or more types.

In the composition of the present invention, the content of the compound represented by the general formula (M) includes solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dripping marks, seizure, and the like. It is necessary to make appropriate adjustments according to the required performance such as dielectric anisotropy.

The lower limit of the preferable content of the compound represented by the formula (M) with respect to the total amount of the composition of the present invention is 1%, 10%, 20%, 30%, 40. %, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The preferred upper limit of the content is, for example, 95%, 85%, 75%, 65%, 55% in one embodiment of the invention, relative to the total amount of the composition of the invention. Yes, 45%, 35%, 25%.

When a composition having a low viscosity and a high response rate is required, it is preferable to lower the lower limit value and lower the upper limit value. Further, when the _TNI of the composition of the present invention is kept high and a composition having good temperature stability is required, it is preferable to lower the lower limit value and lower the upper limit value. Further, when it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable to raise the above lower limit value and raise the upper limit value.

The liquid crystal composition according to the present invention contains a polymerizable compound represented by the general formula (I), but other polymerizable compounds may be used in combination. By using other polymerizable compounds in combination, the polymerization rate and the formation of the pretilt angle of the polymerizable compound can be further accelerated. In addition, a sufficient pretilt angle can be obtained, the residual amount of the polymerizable compound is small, a high voltage retention rate (VHR) can be obtained, and seizure of the liquid crystal display element can be suppressed. Examples of the other polymerizable compound include the following general formula (P).

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

(In the formula, R ^p11 and R ^p12 independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or an alkyl halide group having 1 to 5 carbon atoms, and W ^p11 is a single bond, −O. Representing a −, −COO− or methylene group, t ^p11 represents 0, 1 or 2, but if there are multiple R ^p11 , R ^p12 , W ^p11 and / or t ^{p11 in} the molecule, they are the same. It may be different or different.)
Represents one of
Sp ^p1 and Sp ^p2 independently represent a single bond or a spacer group, respectively.
Z ^p1 and Z ^p2 are independent, single-bonded, -O-, -S-, -CH _2- , -OCH _2- , -CH ₂ O-, -CO-, -C ₂ H ₄ -,-, respectively. _{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, z are each They independently represent integers 1 to 4, and R ^ZP1 independently represent hydrogen atoms or alkyl groups with 1 to 4 carbon atoms, but if there are multiple R ^ZP1s in the molecule, they are the same. It may be different.)
Represents
A ^p1 , A ^p2 and A ^p3 are independent of each other.
^(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 (the one present in the group -CH = or non-adjacent two or more -CH = may be replaced by -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 -2,6-diyl groups (one -CH = existing in these groups or two or more -CH = not adjacent to each other may be replaced with -N =, and hydrogen existing in this group. The atom may be substituted with a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an alkenyl group having 1 to 8 carbon atoms.)
Represents a group selected from the group consisting of the above group (a ^p), group (b ^p) and group (c ^p) are each independently hydrogen atoms present in this group may be substituted with a halogen atom, a carbon It may be substituted with an alkyl group having 1 to 8 atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 1 to 8 carbon atoms. It may be substituted with a cyano group, a fluorine atom, a chlorine atom or -Sp ^p2 -P ^p2 .
m ^p1 represents 0, 1, 2 or 3, and when a plurality of Z ^p1 , ^Ap2 , 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 an anthracene-2,6-diyl group.
However, the compound represented by the general formula (I) is excluded. )
The compound represented by is preferable. Further, it is preferable that the polymerizable monomer is contained alone or in combination of two or more.

In the general formula (P) according to the present invention, R ^p1 is preferably −Sp ^p2 −P ^p2 .

It is preferable that P ^p1 and P ^p2 are independently one of the formulas (P ^p1-1 ) to (P ^p1 -3), and it is preferably (P ^p1-1 ).

It is preferable that R ^p11 and R ^p12 are independently hydrogen atoms or methyl groups, respectively.

t ^p11 is preferably 0 or 1.

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

m ^p1 is preferably 0, 1 or 2, 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-, more preferably a single _{bond, -OCH 2 -, - CH 2} O -, - C 2 H 4 -, - COO -, - OCO -, - COOC 2 H 4 _{-, - OCOC 2 H 4 -} , - C 2 H 4 OCO -, - C 2 H 4 COO -, - CH = CH -, - (CH 2) 2 -COO -, - (CH 2) 2 -OCO- , -OCO- (CH ₂ ) _2- , -CH = CH-COO-, -COO-CH = CH-, -OCOCH = CH-, -COO- (CH ₂ ) ₂ -or -C≡C- are preferred. , 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-bonded. preferably, only one present in the _{molecule, -OCH 2 -, - CH 2} O -, - C 2 H 4 -, - COO- or a -OCO-, that other are all single bonds Preferably, all are single-bonded.

Also, only one of Z ^p1 and Z ^p2 present in the molecule is -CH = CH-COO-, -COO-CH = CH-,-(CH ₂ ) _2- COO-,-(CH ₂ ) _2. It is a linking group selected from the group consisting of −OCO−, −O—CO− (CH ₂ ) ₂ −, −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, but the spacer group is preferably an alkylene group having 1 to 30 carbon atoms, and −CH ₂ − in the alkylene group contains oxygen atoms. As long as it is not directly linked, it 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. Although it may be substituted with, a linear alkylene group having 1 to 10 carbon atoms or a single bond is preferable.
A ^p1 , A ^p2 and A ^p3 are independent of each other, preferably a 1,4-phenylene group or a 1,4-cyclohexylene group, 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 preferably 0.05 to 10% with respect to the composition containing the compound represented by the general formula (P) of the present application. It preferably contains 0.1 to 8%, preferably 0.1 to 5%, preferably 0.1 to 3%, and preferably 0.2 to 2%. It is preferably contained in an amount of 0.2 to 1.3%, preferably 0.2 to 1%, and preferably 0.2 to 0.56%.

The preferable lower limit of the total content of the compounds represented by the general formula (P) is 0.01% with respect to the composition containing the compound represented by the general formula (P) of the present application, and is 0. 03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3 %.

The preferable upper limit of the total content of the compounds represented by the general formula (P) is 10% and 8% with respect to the composition containing the compound represented by the general formula (P) of the present application. It is 5%, it is 3%, it is 1.5%, it is 1.2%, it is 1%, it is 0.8%, and it is 0.5%.

If the content is low, the effect of adding the compound represented by the general formula (P) is unlikely to appear, and problems such as weak orientation control force of the liquid crystal composition or weakening over time occur. Problems such as a large amount remaining afterwards, a long curing time, and a decrease in the reliability of the liquid crystal occur. Therefore, the content is set in consideration of these balances.

The total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is preferably 0.05 to 10% with respect to the composition containing these compounds. , 0.1 to 8% is preferably contained, 0.1 to 5% is preferably contained, 0.1 to 3% is preferably contained, and 0.2 to 2% is contained. It is preferable that it contains 0.2 to 1.3%, preferably 0.2 to 1%, and preferably 0.2 to 0.56%.

The preferable lower limit of the total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is 0.01% with respect to the composition containing these compounds, which is 0. .03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.03%. It is 3%.

The preferable upper limit of the total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is 10% and 8% with respect to the composition containing these compounds. Yes, 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, 0.5%.

If the content is small, the effect of adding the compound represented by the general formula (I) and the compound represented by the general formula (P) is unlikely to appear, and the orientation regulating force of the liquid crystal composition becomes weak or weak with time. If the amount is too large, the amount remaining after curing will increase, curing will take time, and the reliability of the liquid crystal will decrease. Therefore, the content is set in consideration of these balances.

Preferred examples of the compound represented by the general formula (P) according to the present invention 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), respectively.)
Preferred examples of the compound represented by the general formula (P) according to the present invention include polymerizable compounds represented by the following formulas (P-2-1) to (P-2-14).

(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), respectively.)
Preferred examples of the compound represented by the general formula (P) according to the present invention 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) according to the present invention include polymerizable compounds represented by the following formulas (P-4-1) to (P-4-21).

(In the formula, P ^p41 , P ^p42 , Sp ^p41 and Sp ^p42 have the same meanings as P ^p1 , P ^p2 , Sp ^p1 and Sp ^p2 in the general formula (P). Multiple P ^p41 , P ^{p42 in the} formula. , Sp ^p41 and Sp ^p42 may be the same or different, respectively.)
When the monomer is added to the composition of the present invention, the polymerization proceeds even in the absence of the polymerization initiator, but the polymerization initiator may be contained in order to promote the polymerization. Examples of the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, acylphosphine oxides and the like.

The composition in the present invention can further contain a compound represented by the general formula (Q).

(Wherein, R ^Q represents a straight-chain alkyl group or branched alkyl group having from 1 22 carbon atoms, one or two or more CH ₂ groups in the alkyl group, so that the oxygen atoms are not directly adjacent a, -O -, - CH = CH -, - CO -, - OCO -, - COO -, - C≡C -, - CF 2 O -, - OCF 2 - may be replaced by, ^{M Q} is trans Represents a -1,4-cyclohexylene group, a 1,4-phenylene group or a single bond)
^RQ represents a linear 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 −O so that oxygen atoms are not directly adjacent to each other. −, −CH = CH−, −CO−, −OCO−, −COO−, −C≡C−, −CF ₂ O−, −OCF ₂₋ may be substituted, but the number of carbon atoms is 1 to 10. Linear alkyl group, linear alkoxy group, linear alkyl group in which one CH ₂ group is substituted with -OCO- or -COO-, branched chain alkyl group, branched alkoxy group, one CH ₂ group is -OCO- Alternatively, a branched chain alkyl group substituted with -COO- is preferable, a linear alkyl group having 1 to 20 carbon atoms, and a linear alkyl group in which one CH ₂ group is substituted with -OCO- or -COO-, or branched. A chain alkyl group, a branched alkoxy group, and a branched chain alkyl group in which one CH ₂ group is substituted with -OCO- or -COO- are further preferable. ^MQ represents a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a single bond, with a trans-1,4-cyclohexylene group or a 1,4-phenylene group being preferred.

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

Wherein, R ^Q1 is preferably a linear alkyl group or branched alkyl group having 1 to 10 carbon atoms, R ^Q2 is preferably a linear alkyl group or branched alkyl group having 1 to 20 carbon atoms, R ^Q3 is linear alkyl group having a carbon number of 1 to 8, branched chain alkyl group, preferably a linear alkoxy group or a branched chain alkoxy group, L ^Q is preferably a linear alkylene group or branched alkylene group having 1 to 8 carbon atoms .. Among the compounds represented by the general formulas (Qa) to (Qd), the compounds represented by the general formulas (Qc) and the general formula (Qd) are more preferable.

The composition of the present invention preferably contains one or two compounds represented by the general formula (Q), more preferably one to five, and the content thereof is from 0.001. It is preferably 1%, more preferably 0.001 to 0.1%, and particularly preferably 0.001 to 0.05%.

In addition to the above-mentioned compounds, the liquid crystal composition of the present invention may contain ordinary nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, antioxidants, ultraviolet absorbers, light stabilizers, infrared absorbers and the like.

Further, as an antioxidant or a light stabilizer that can be used in the present invention, more specifically, the compounds represented by the following (III-1) to (III-40) are preferable.

(In the formula, n represents an integer from 0 to 20.)
The composition of the present invention preferably contains one or more compounds represented by the general formula (Q) or compounds selected from the general formulas (III-1) to (III-40). , The content thereof is more preferably 0.001 to 1%, further preferably 0.001 to 0.1%, and particularly preferably 0.001 to 0.05%.

In the liquid crystal composition of the present invention, the dielectric anisotropy (Δε) at 20 ° C. is preferably from -2.0 to -8.0, more preferably from -2.0 to -5.0, and from -2.5. -5.0 is particularly preferable.

In the liquid crystal composition of the present invention, the refractive index anisotropy (Δn) at 20 ° C. is preferably 0.08 to 0.14, more preferably 0.09 to 0.13, and particularly 0.09 to 0.12. preferable. More specifically, it is preferably 0.10 to 0.13 when dealing with a thin cell gap, and preferably 0.08 to 0.10. When dealing with a thick cell gap.

The liquid crystal composition of the present invention has a viscosity (η) at 20 ° C. of preferably 10 to 50 mPa · s, preferably 10 to 40 mPa · s, and preferably 10 to 35 mPa · s. It is preferably from 10 to 30 mPa · s, more preferably from 10 to 25 mPa · s, and particularly preferably from 10 to 22 mPa · s.

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

In the liquid crystal composition of the present invention, the nematic phase-isotropic liquid phase transition temperature (T _ni ) is preferably 60 ° C to 120 ° C, more preferably 70 ° C to 100 ° C, and particularly preferably 70 ° C to 85 ° C.

A preferred embodiment of the liquid crystal composition according to the present invention is divided into a case where the entire liquid crystal composition exhibits positive dielectric anisotropy and a case where the entire liquid crystal composition exhibits negative dielectric anisotropy. Is preferable.

For example, when the entire liquid crystal composition according to the present invention exhibits positive dielectric anisotropy, a compound selected from a polymerizable compound represented by the general formula (I) and a compound represented by the general formula (J). It is preferable to include one kind or two or more kinds and a compound represented by the general formula (L).

The upper limit of the proportion of the component composed only of the compounds represented by the general formula (I), the general formula (J) and the general formula (L) in the entire liquid crystal composition according to the present invention 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% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87 It is preferably mass%, 86% by mass, 85% by mass, and 84% by mass.

Further, the lower limit of the proportion of the component composed only of the compounds represented by the general formula (I), the general formula (J) and the general formula (L) in the entire liquid crystal composition according to the present invention is 78. Mass%, 80% by mass, 81% by mass, 83% by mass, 85% by mass, 86% by mass, 87% by mass, 88% by mass, 89% by mass, 90% by mass, 91% by mass, 92% by mass, 93% by mass , 94% by mass, 95% by mass, 96% by mass, 97% by mass, 98% by mass, and 99% by mass.

The upper limit of the proportion of the component composed only of the compounds represented by the general formula (I), the general formula (P) and the general formula (L) in the entire liquid crystal composition according to the present invention 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% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87 It is preferably mass%, 86% by mass, 85% by mass, and 84% by mass.

Further, the lower limit of the proportion of the component composed only of the compounds represented by the general formula (I), the general formula (P) and the general formula (L) in the entire liquid crystal composition according to the present invention is 78. 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.

For example, when the entire liquid crystal composition according to the present invention exhibits negative dielectric anisotropy, the polymerizable compound represented by the general formula (I) and the general formulas (N-1), (N-2) and It is preferable to include one or more compounds selected from the compounds represented by (N-3) and the compound represented by the general formula (L).

Among the entire liquid crystal composition according to the present invention, it is 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 ratio of the component composed only of the compound 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% 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, among the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1), the general formula (N-2), the general formula (N-3) and the general formula (L) are represented. The lower limit of the proportion of the component composed only of the compound is 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. It is preferably mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.

Of the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), and the general formula The upper limit of the proportion of the component composed only of the compound represented by the formula (N-1e) and the general formula (L) 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% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, 84% by mass. Is preferable.

Further, among the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), and the general formula (N-1d) , The lower limit of the proportion of the component composed only of the compound represented by the general formula (N-1e) and the general formula (L) 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%, 97 mass% , 98% by mass, preferably 99% by mass.

Of the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1-4), the general formula (N-1b), the general formula (N-1c), and the general formula (N-1d) , The upper limit of the proportion of the component composed only of the compound represented by the general formula (N-1e) and the general formula (L) is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96. Mass%, 95% by mass, 94% by mass, 93% by mass, 92% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, 84% by mass Is preferable.

Further, among the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1-4), the general formula (N-1b), the general formula (N-1c), and the general formula (N-). 1d), the lower limit of the proportion of the component composed only of the compound represented by the general formula (N-1e) and the general formula (L) is 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 It is preferably mass%, 98% by mass, and 99% by mass.

Of the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), and the general formula It is represented by the formula (N-1e), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5) and the general formula (L-6). The upper limit of the ratio of the component composed only of the compound 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% by mass. , 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, 84% by mass, 83% by mass, 82% by mass, 81% by mass, 80% by mass. Is preferable.

Further, among the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), and the 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 of the component composed only of the compound is 68% by mass, 70% by mass, 71% by mass, 73% by mass, 75% by mass, 78% by mass, 80% by mass, 81% by 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% by mass, 98% by mass, and 99% by mass are preferable.

Of the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1a), the general formula (L-1), the general formula (L-3), the general formula (L-4), and the general formula The upper limit of the proportion of the component composed only of the compound represented by the formula (L-5) and the general formula (L-6) is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96. Mass%, 95% by mass, 94% by mass, 93% by mass, 92% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, 84% by mass , 83% 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. It is preferably mass%, 70 mass%, 69 mass%, 68 mass%, 67 mass%, 66 mass%, 65 mass%, 64 mass%, 63 mass%, 62 mass%.

Further, among the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1a), the general formula (L-1), the general formula (L-3), and the general formula (L-4) , The lower limit of the proportion of the component composed only of the compound represented by the general formula (L-5) and the general formula (L-6) is 38% by mass, 40% by mass, 41% by mass, 43% by mass. , 45% by mass, 48% by mass, 50% by mass, 61% by mass, 63% by mass, 65% by mass, 66% by mass, 67% by mass, 68% by mass, 69% by mass, 70% by mass, 72% by mass, 74 It is preferably mass%, 76 mass%, 78 mass%, 80 mass%, 82 mass%, 84 mass%, 86 mass%, 88 mass%, 90 mass%, 92 mass%.

Of the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1d), the general formula (L-1), the general formula (L-3), the general formula (L-4), and the general formula The upper limit of the proportion of the component composed only of the compound represented by the formula (L-5) and the general formula (L-6) is 100% by mass, 99% by mass, 98% by mass, 97% by mass, 96. Mass%, 95% by mass, 94% by mass, 93% by mass, 92% by mass, 91% by mass, 90% by mass, 89% by mass, 88% by mass, 87% by mass, 86% by mass, 85% by mass, 84% by mass , 83% 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. It is preferably mass%, 70 mass%, 69 mass%, 68 mass%, 67 mass%, 66 mass%, 65 mass%, 64 mass%, 63 mass%, 62 mass%.

Further, among the entire liquid crystal composition according to the present invention, the general formula (I), the general formula (N-1d), the general formula (L-1), the general formula (L-3), and the general formula (L-4) , The lower limit of the proportion of the component composed only of the compound represented by the general formula (L-5) and the general formula (L-6) is 38% by mass, 40% by mass, 41% by mass, 43% by mass. , 45% by mass, 48% by mass, 50% by mass, 61% by mass, 63% by mass, 65% by mass, 66% by mass, 67% by mass, 68% by mass, 69% by mass, 70% by mass, 72% by mass, 74 It is preferably mass%, 76 mass%, 78 mass%, 80 mass%, 82 mass%, 84 mass%, 86 mass%, 88 mass%, 90 mass%, 92 mass%.

The 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 composition are emphasized, the content of the compound having a carbonyl group is preferably 5% or less, more preferably 3% or less, based on the total mass of the composition. It is preferably 1% or less, and most preferably not substantially contained.

When the stability by UV irradiation is emphasized, the content of the compound substituted with chlorine atoms is preferably 15% or less, preferably 10% or less, based on the total mass of the composition. % Or less, more preferably 5% or less, more preferably 3% or less, and even more preferably substantially no content.

It is preferable to increase the content of the compound having all 6-membered ring structures in the molecule, and the content of the compound having all 6-membered ring structures in the molecule is 80 with respect to the total mass of the composition. % Or more, more preferably 90% or more, further preferably 95% or more, and the composition is composed only of a compound in which substantially all the ring structures in the molecule are 6-membered rings. It is most preferable to do so.

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

When the improvement of viscosity and the improvement of _TNI are emphasized, the content of the compound having a 2-methylbenzene-1,4-diyl group in which the hydrogen atom may be substituted with halogen should be reduced. The content of the compound having a 2-methylbenzene-1,4-diyl group in the molecule is preferably 10% or less, preferably 8% or less, based on the total mass of the composition. It is preferably 5% or less, more preferably 3% or less, and even more preferably substantially absent.

In the present application, substantially not contained means that it is not contained except for an unintentionally contained substance.
(Liquid crystal display element)
The liquid crystal display device using the liquid crystal composition of the present invention has a remarkable feature of high-speed response, and in addition, a sufficient tilt angle can be obtained, and there is no problem whether there is an unreacted polymerizable compound or not. Since it is not so small and the voltage retention rate (VHR) is high, there are no defects such as poor orientation and poor display, or they are sufficiently suppressed. Further, 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 production, which is most suitable for improving production efficiency and stable mass production.

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

As an example of the liquid crystal display element according to the present invention, a first substrate and a second substrate arranged to face each other, a common electrode provided on the first substrate or the second substrate, and the first substrate. It is preferable to have a pixel electrode provided on the substrate or the second substrate and having a thin film transistor, and a liquid crystal layer containing a liquid crystal composition provided between the first substrate and the second substrate. If necessary, an alignment film for controlling the orientation direction of the liquid crystal molecules may be provided on the facing surface side of at least one substrate of the first substrate and / or the second substrate so as to come into contact with the liquid crystal layer. As the alignment film, a vertical alignment film, a horizontal alignment film, or the like can be appropriately selected according to the drive mode of the liquid crystal display element, such as a rubbing alignment film (for example, polyimide) or a photoalignment film (decomposition type polyimide, etc.). A known alignment film of the above can be used. Further, the color filter may be appropriately provided on the first substrate or the second substrate, and the color filter may be provided on the pixel electrode or the common electrode.

For the two substrates of the liquid crystal cell used in the liquid crystal display element according to the present invention, a transparent material having flexibility such as glass or plastic can be used, and one of them may be an opaque material such as silicon. A transparent substrate having a 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 produced by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like. To explain a method for producing a color filter by a pigment dispersion method as an example, a curable coloring composition for a color filter is applied onto the transparent substrate, subjected to a 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 resistivity element may be installed on the substrate.

It is preferable that the first substrate and the second substrate face each other so that the common electrode and the pixel electrode layer are on the inside.

The distance between the first substrate and the second substrate may be adjusted via a spacer. At this time, it is preferable to adjust the thickness of the obtained dimming layer to be 1 to 100 μm. It is more preferably 1.5 to 10 μm, and 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, the polarization axis of each polarizing plate can be adjusted so that the viewing angle and contrast can be improved. Further, a retardation film for widening the viewing angle can also be used. Examples of the spacer include glass particles, plastic particles, alumina particles, photoresist material and the like. Then, a sealant such as an epoxy-based thermosetting composition is screen-printed on the substrate in the form of providing a liquid crystal injection port, the substrates are bonded to each other, and the sealant is thermoset by heating.

As a method for sandwiching the liquid crystal composition between the two substrates, a normal vacuum injection method, an ODF method, or the like can be used.

As a method for polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention, an appropriate polymerization rate is desirable in order to obtain good orientation performance of the liquid crystal. Therefore, active energy rays such as ultraviolet rays or electron beams are simply used. A method of polymerizing by irradiating one or a combination or in order is preferable. When ultraviolet rays are used, a polarized light source may be used, or a non-polarized light source may be used. Further, when polymerization is carried out with the liquid crystal composition sandwiched between two substrates, at least the substrate on the irradiation surface side must be provided with appropriate transparency with respect to active energy rays. In addition, after polymerizing only a specific part using a mask during light irradiation, the orientation state of the unpolymerized part is changed by changing conditions such as electric field, magnetic field, or temperature, and further irradiation with active energy rays. You may use the means of polymerizing. In particular, when exposed to ultraviolet rays, it is preferable to expose the liquid crystal composition to ultraviolet rays while applying an AC electric field. The AC electric field to be applied is preferably an AC having a frequency of 10 Hz to 10 kHz, more preferably a frequency of 60 Hz to 10 kHz, and the voltage is selected depending on a 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 a liquid crystal display element such as a liquid crystal display element in PSVA mode, in which the orientation of liquid crystal molecules when no voltage is applied, that is, the initial orientation of the liquid crystal is substantially perpendicular to the substrate, pretilt from the viewpoint of orientation stability and contrast. It is preferable to control the angle from 80 degrees to 89.9 degrees. In addition, substantially vertical includes an angle having a pre-tilt angle as described above, and preferably the angle between the long axis direction of the liquid crystal molecule and the substrate is 70 degrees or more, more preferably 75 degrees or more, still more preferably. It is 80 degrees or more.

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

On the other hand, for example, when the liquid crystal composition of the present invention is applied to a liquid crystal display element having a substrate having no alignment film, it is applied to the liquid crystal display element having the substrate having the alignment film at the time of irradiation. The temperature range may be wider than the temperature range.

As the lamp that generates ultraviolet rays, a metal halide lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, or the like can be used. Further, 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 liquid crystal composition, and it is preferable to cut the ultraviolet rays before use. The intensity of the ultraviolet rays to be irradiated 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 irradiating with ultraviolet rays. The time for irradiating the ultraviolet rays is appropriately selected depending on the intensity of the ultraviolet rays to be irradiated, but is preferably 10 seconds to 3600 seconds, more preferably 10 seconds to 600 seconds.

Although an example of the liquid crystal display element and the method for manufacturing the liquid crystal display element of the present invention has been described above, the present invention is not limited to the above-described embodiment.

For example, the liquid crystal display element of the present invention may replace a part of the configuration with another configuration exhibiting the same function, or may add an arbitrary configuration. Further, the method for manufacturing a liquid crystal display element of the present invention may have an additional step having an arbitrary purpose, or may be replaced with an arbitrary step in which the same action / effect can be obtained.

The present invention will be described in more detail with reference to Examples below, but the present invention is not limited to these Examples. In addition, "%" in the compositions of the following Examples and Comparative Examples means "mass%". The following abbreviations are used for the description of compounds in the examples.
<Synthesis of liquid crystal compounds>
(Reference example 1)
To a reaction vessel equipped with a stirrer, a cooler and a thermometer, 5.0 g (31 mmol) of 1,4-naphthalenediol, 6.4 g (74 mmol) of methacrylic acid, 800 mg of dimethylaminopyridine and 100 ml of methylene chloride were added. The reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 9.3 g (74 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 150 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column, and recrystallization with methylene chloride / hexane gave 7.2 g of the target compound represented by the formula (RM-1).

^{1 1} H-NMR (solvent: deuterated chloroform): δ: 2.16 (s, 6H), 5.87 (m, 2H), 6.52 (m, 2H), 7.32 (s, 2H), 7 .52-7.56 (m, 2H), 7.86-7.91 (m, 2H)
¹³ C-NMR (solvent: deuterated chloroform): δ: 17.9, 109.3, 122.6, 127.1, 128.0, 128.8, 135.3, 145.5, 166.0
Infrared absorption spectrum (IR) (KBr): 1740-1730, 1600, 760 cm ^-1
Melting point: 67 ° C
(Reference example 2)
In a reaction vessel equipped with a stirrer, cooler and thermometer, 6.4 g (40 mmol) of 1,5-naphthalenediol, 7.6 g (88 mmol) of methacrylate, 1.0 g (8 mmol) of dimethylaminopyridine, 200 mL of dichloromethane was added, and the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 11.6 g (92 mmol) of diisopropylcarbodiimide was added dropwise. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 24 hours. After filtering the reaction solution, the filtrate was washed with a 10% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a silica gel column in a double amount (weight ratio), and 2.9 g of the target compound represented by the formula (RM-2) was obtained by recrystallization with dichloromethane / methanol.

^{1 1} H-NMR (solvent: deuterated chloroform): δ: 2.16 (s, 6H), 5.87 (m, 2H), 6.52 (m, 2H), 7.33 (m, 2H), 7 .51 (m, 2H), 7.79 (m, 2H)
13C-NMR (solvent: deuterated chloroform): δ: 18.5, 118.7, 119.2, 126.0, 127.7, 128.3, 135.6, 146.9, 165.6
Infrared absorption spectrum (IR) (KBr): 1740, 1240, 1120, 950, 780 cm-1
Melting point: 113 ° C
(Example 3)
12 g (62 mmol) of 4-bromo-1-naphthol, 8.6 g (56 mmol) of p-methoxyphenylboric acid, 13 g (98 mmol) of potassium carbonate, in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. 1 g of tetrakistriphenylphosphine palladium, 200 ml of tetrahydrofuran, and 100 ml of pure water were added, and the reactor was heated to 85 ° C. in a nitrogen gas atmosphere to react. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 5% aqueous hydrochloric acid solution, pure water, and saturated brine. After distilling off the solvent, purification was carried out with a silica gel column in a double amount (weight ratio) to obtain 9 g of the compound represented by the formula (1).

Next, 9 g of the compound represented by the formula (1), 36 ml of acetic acid and 22 ml of hydrobromic acid were added to a reaction vessel equipped with a stirrer, a cooler and a thermometer, and the mixture was refluxed at 120 ° C. for 5 hours. After completion of the reaction, the mixture was cooled, and the precipitated crystals were washed with water and a water / methanol mixed solvent and then vacuum dried to obtain 7.5 g of the compound represented by the formula (2).

Further, in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 7.5 g (31 mmol) of the compound represented by the above formula (2), 6.4 g (74 mmol) of methacrylic acid, 800 mg of dimethylaminopyridine, and methylene chloride 100 ml was added, the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 9.3 g (74 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 150 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column, and 6.5 g of the target compound represented by the formula (RM-3) was obtained by recrystallization with methylene chloride / hexane.

(Physical characteristic value)
^{1 1} H-NMR (solvent: deuterated chloroform): δ: 2.11 (s, 3H), 2.19 (s, 3H), 5.80 (s, 1H), 5.89 (s, 1H), 6 .41 (s, 1H), 6.56 (s, 1H), 7.24-7.27 (m, 2H), 7.33-7.35 (m, 1H), 7.42-7.55 (M, 5H), 7.90-7.95 (m, 2H)
¹³ C-NMR (solvent: deuterated chloroform): δ: 18.4, 18.5, 117.6, 121.4, 121.5, 126.3, 126.5, 126.6, 127.0, 127 .4, 127.7, 131.1, 132.8, 135.8, 135.9, 137.4, 137.5, 146.3, 150.3, 165.9
Infrared absorption spectrum (IR) (KBr): 1740, 1640, 1600-1580, 810 cm ^-1
Melting point: 117 ° C
(Example 4)
24 g (124 mmol) of 5-bromo-1-naphthol, 17.2 g (112 mmol) of p-methoxyphenylboric acid, 26 g (196 mmol) of potassium carbonate, in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. 2 g of tetrakistriphenylphosphine palladium, 400 ml of tetrahydrofuran, and 200 ml of pure water were added, and the reactor was heated to 85 ° C. in a nitrogen gas atmosphere to react. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 5% aqueous hydrochloric acid solution, pure water, and saturated brine. After distilling off the solvent, purification was carried out with a silica gel column in a double amount (weight ratio) to obtain 18 g of the compound represented by the formula (3).

Next, 18 g of the compound represented by the formula (3), 72 ml of acetic acid and 44 ml of hydrobromic acid were added to a reaction vessel equipped with a stirrer, a cooler and a thermometer, and the mixture was refluxed at 120 ° C. for 5 hours. After completion of the reaction, the mixture was cooled, and the precipitated crystals were washed with water and a water / methanol mixed solvent and then vacuum dried to obtain 15 g of the compound represented by the formula (4).

Further, in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 15 g (62 mmol) of the compound represented by the above formula (4), 12.8 g (148 mmol) of methacrylic acid, 1.6 g of dimethylaminopyridine, and methylene chloride 200 ml was added, the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 18.6 g (148 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 300 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column, and recrystallization with methylene chloride / hexane gave 12.1 g of the target compound represented by the formula (RM-4).

(Physical characteristic value)
^{1 1} H-NMR (solvent: deuterated chloroform): δ: 2.11 (s, 3H), 2.17 (s, 3H), 5.79 (s, 1H), 5.88 (s, 1H), 6 .40 (s, 1H), 6.54 (s, 1H), 7.24-7.30 (m, 3H), 7.42-7.54 (m, 5H), 7.78 (d, 1H) ), 7.88 (d, 1H)
Melting point: 99 ° C
(Example 5)
20 g (70 mmol) of 1,4-dibromonaphthalene, 19.4 g (141 mmol) of p-hydroxyphenylboric acid, 34 g (245 mmol) of potassium carbonate, tetrakis in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. 4 g of triphenylphosphine palladium, 300 ml of tetrahydrofuran, and 150 ml of pure water were added, and the reactor was heated to 85 ° C. in a nitrogen gas atmosphere to react. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 5% aqueous hydrochloric acid solution, pure water, and saturated brine. After distilling off the solvent, purification was carried out with a silica gel column in a 10-fold amount (weight ratio) to obtain 11 g of the compound represented by the formula (5).

Next, 11 g (35 mmol) of the compound represented by the above formula (5), 7.2 g (84 mmol) of methacrylic acid, 940 mg of dimethylaminopyridine, and 70 ml of methylene chloride were placed in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. In addition, the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 10.6 g (84 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 100 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column, and 11.2 g of the target compound represented by the formula (RM-5) was obtained by recrystallization with methylene chloride / hexane.

(Physical characteristic value)
^{1 1} H-NMR (solvent: deuterated chloroform): δ: 2.11 (s, 6H), 5.80 (s, 2H), 6.41 (s, 2H), 7.25-7.29 (m, 4H), 7.43-7.46 (m, 4H), 7.53-7.56 (m, 4H), 7.94-7.98 (m, 2H)
Melting point: 163 ° C
(Example 6)
20 g (70 mmol) of 1,5-dibromonaphthalene, 19.4 g (141 mmol) of p-hydroxyphenylboric acid, 34 g (245 mmol) of potassium carbonate, tetrakis in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. 4 g of triphenylphosphine palladium, 300 ml of tetrahydrofuran, and 150 ml of pure water were added, and the reactor was heated to 85 ° C. in a nitrogen gas atmosphere to react. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 5% aqueous hydrochloric acid solution, pure water, and saturated brine. After distilling off the solvent, purification was carried out with a silica gel column in a 10-fold amount (weight ratio) to obtain 11 g of the compound represented by the formula (6).

Next, 11 g (35 mmol) of the compound represented by the above formula (6), 7.2 g (84 mmol) of methacrylic acid, 940 mg of dimethylaminopyridine, and 70 ml of methylene chloride were placed in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. In addition, the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 10.6 g (84 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 100 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column, and recrystallization with methylene chloride / hexane gave 12.5 g of the target compound represented by the formula (RM-6).

(Physical characteristic value)
^{1 1} H-NMR (solvent: deuterated chloroform): δ: 2.11 (s, 6H), 5.80 (s, 2H), 6.41 (s, 2H), 7.26 (d, 4H), 7 .42-7.49 (m, 6H), 7.50 (d, 2H), 7.91 (d, 2H)
Melting point: 223 ° C
(Example 7)
12 g (54 mmol) of 4-bromo-1-naphthol, 11.9 g (4- (tetrahydro-2H-pyran-2-yloxy) phenyl) boronic acid in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. 54 mmol), 18.7 g (135 mmol) of potassium carbonate, 1.5 g of tetrakistriphenylphosphine palladium, 200 ml of tetrahydrofuran, and 100 ml of pure water were added, and the reactor was heated to 85 ° C. under a nitrogen gas atmosphere to react. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 5% aqueous hydrochloric acid solution, pure water, and saturated brine. After distilling off the solvent, purification was carried out with a silica gel column in a double amount (weight ratio) to obtain 14 g of the compound shown in (7).

Next, 14 g (44 mmol) of the compound represented by the above formula (7), 5.3 g (61 mmol) of methacrylic acid, 530 mg of dimethylaminopyridine, and 77 ml of methylene chloride were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer. The reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 7.2 g (57 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 35 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column, and recrystallization with methylene chloride / hexane gave 14 g of the compound represented by the formula (8).

Further, 14 g of the compound represented by the above formula (8), 70 ml of tetrahydrofuran and 28 ml of a 10% hydrochloric acid aqueous solution were added to a reaction vessel equipped with a stirrer, a cooler and a thermometer, and the mixture was reacted at 40 ° C. for 5 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with pure water and saturated brine. After distilling off the solvent, purification was carried out with a silica gel column in a double amount (weight ratio), and 8.9 g of the compound represented by the formula (9) was obtained by recrystallization with methylene chloride / hexane.

Finally, 8.9 g (29 mmol) of the compound represented by the above formula (9), 4.5 g (35 mmol) of diisopropylethylamine, and 120 ml of methylene chloride were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer. The reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 3 g (34 mmol) of acryloyl chloride was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. 50 ml of methylene chloride was added to the reaction solution, washed with aqueous hydrochloric acid solution, subsequently washed with water, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a 10-fold amount (weight ratio) of a silica column to obtain 6.5 g of the target compound represented by the formula (RM-7).

(Physical characteristic value)
^{1 1} H-NMR (solvent: deuterated chloroform): δ: 2.18 (s, 3H), 5.87-5.88 (m, 1H), 6.05 (dd, 1H), 6.38 (dd, dd, 1H), 6.55 (s, 1H), 6.66 (dd, 1H), 7.25-7.28 (m, 2H), 7.33 (d, 1H), 7.42-7.54 (M, 5H), 7.89-7.95 (m, 2H)
Infrared absorption spectrum (IR) (KBr): 1730, 1640, 1600-1580, 760 cm ^-1
Melting point: 101 ° C
(Example 8)
Add 8.5 g (27 mmol) of the compound represented by the above formula (5), 2.3 g (27 mmol) of methacrylic acid, 160 mg of dimethylaminopyridine, and 60 ml of methylene chloride, and keep the reaction vessel at 5 ° C. or lower in an ice-cooled bath. , 3.4 g (27 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 30 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a 10-fold amount (weight ratio) of silica column, and 4.4 g of the target compound represented by the formula (10) was obtained by recrystallization with methylene chloride / hexane.

Next, 4.4 g (12 mmol) of the compound represented by the above formula (10), 1.8 g (14 mmol) of diisopropylethylamine, and 50 ml of methylene chloride were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer, and ice was added. The reaction vessel was kept at 5 ° C. or lower in a cold bath, and 1.2 g (13 mmol) of acryloyl chloride was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. To the reaction solution, 20 ml of methylene chloride was added, and the mixture was washed with an aqueous hydrochloric acid solution, subsequently with water, further with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column to obtain 4.1 g of the target compound represented by the formula (RM-8).

(Physical characteristic value)
^{1 1} H-NMR (solvent: deuterated chloroform): δ: 2.11 (s, 3H), 5.79 (t, 1H), 6.05 (dd, 1H), 6.35-6.42 (m, 2H), 6.66 (dd, 1H), 7.25-7.33 (m, 4H), 7.41-7.56 (m, 8H), 7.93-7.98 (m, 2H)
Melting point: 148 ° C
(Example 9)
10 g (44 mmol) of 4-bromo-1-naphthol, 8 g (47 mmol) of 3-fluoro-4-methoxyphenylboric acid, 9 g (70 mmol) of potassium carbonate in a reaction vessel equipped with a stirrer, a cooler, and a thermometer. ), Tetrakistriphenylphosphine palladium (500 mg), tetrahydrofuran (200 ml), and pure water (100 ml) were added, and the reactor was heated to 85 ° C. under a nitrogen gas atmosphere to react. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 5% aqueous hydrochloric acid solution, pure water, and saturated brine. After distilling off the solvent, purification was carried out with a silica gel column in a double amount (weight ratio) to obtain 9 g of the compound represented by the formula (11).

Next, 9 g of the compound represented by the formula (11), 36 ml of acetic acid, and 22 ml of hydrobromic acid were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer, and the mixture was refluxed at 120 ° C. for 5 hours. After completion of the reaction, the mixture was cooled, and the precipitated crystals were washed with water and a water / methanol mixed solvent and then vacuum dried to obtain 7.3 g of the compound represented by the formula (12).

Further, in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 7 g (27 mmol) of the compound represented by the above formula (12), 6.6 g (77 mmol) of methacrylic acid, 200 mg of dimethylaminopyridine and 100 ml of methylene chloride were added. In addition, the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 8.3 g (66 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 150 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column, and recrystallization with methylene chloride / hexane gave 4.2 g of the target compound represented by the formula (RM-9).

(Physical characteristic value)
LC-MS 391.1 (MS + H)
(Reference example 3)
In a reaction vessel equipped with a stirrer, condenser and thermometer, 6.8 g (27 mmol) of 4-bromo-1-naphthoic acid, 4.7 g (38 mmol) of 4-methoxyphenol, 100 mg of dimethylaminopyridine, methylene chloride. 100 ml was added, the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 4.2 g (33 mmol) of diisopropylcarbodiimide was slowly added dropwise in an atmosphere of nitrogen gas. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 5 hours. After filtering the reaction solution, 150 ml of methylene chloride was added to the filtrate, washed with a 5% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out with a double amount (weight ratio) of an alumina column, and 7.7 g of the compound represented by the formula (13) was obtained by recrystallization with methylene chloride / hexane.

Next, 0.6 g (23.7 mmol) of magnesium, 22 mL of THF, and 7.7 g of the compound represented by the formula (13) were added dropwise to a reaction vessel equipped with a stirrer, a cooler, and a thermometer, and then refluxed at 66 ° C. for 1 hour. I let you. Then, the mixture was cooled to 5 ° C., 2.7 g (25.9 mmol) of trimethyl borate was added dropwise, and the mixture was reacted at room temperature for 1 hour. The mixture was cooled to 5 ° C., 30 ml of a 5% aqueous hydrochloric acid solution was added, and the mixture was stirred at room temperature for 1 hour. After washing with water, 10 ml of a 5% aqueous sodium bicarbonate solution was added, the mixture was cooled to 5 ° C., and 1 ml of a 30% aqueous hydrogen peroxide solution and 22 ml of toluene were added. Further, the mixture was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, it was purified by a double amount (weight ratio) of an alumina column and dried. Recrystallization from methylene chloride / methanol gave 7.7 g of the compound represented by the formula (14).

6.6 g of the compound represented by the formula (15) was obtained by the same method except that the compound represented by the formula (1) of Example 3 was changed to the compound represented by the formula (14).

7.8 g of the target compound represented by the formula (RM-10) was obtained by the same method except that the compound represented by the formula (2) of Example 3 was changed to the compound represented by the formula (15).

(Physical characteristic value)
LC-MS 417.2 (MS + H)
<Adjustment / evaluation of liquid crystal composition>
The following abbreviations are used to describe compounds in the following examples.

(Side chain)
−N −C _n H _{2n + 1} linear alkyl group having n carbon atoms n−C _n H _{2n + 1} − linear alkyl group having n _{+ 1} carbon atoms −On −OC _n H _{2n + 1} linear alkoxy group having n ₊ carbon atoms Group −V −CH = CH ₂
−V1 −CH = CH-CH ₃
V-CH ₂ = CH-
1V-CH _3- CH = CH-
(Connecting group)
-1O--CH _2- O-
−N− −C _n H _2n−
(Ring structure)

The characteristics measured in the examples are as follows.

T _ni : Nematic phase-isotropic liquid phase transition temperature (° C)
Δn: Refractive index anisotropy at 20 ° C. γ ₁ : Rotational viscosity at 20 ° C. (mPa · s)
Δε: Dielectric constant anisotropy at 20 ° C

(Manufacturing method of liquid crystal display element)
First, a polymerizable compound-containing liquid crystal composition described later was injected by a vacuum injection method into a liquid crystal cell having a cell gap of 3.5 μm containing a substrate with ITO coated and rubbed with a polyimide alignment film that induces vertical orientation.

Then, the liquid crystal cell into 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 center wavelength of 313 nm was 3 mW / cm ² .
(Evaluation method of residual amount of polymerizable compound)
Under the above irradiation conditions, the residual amount [ppm] of the polymerizable compound in the liquid crystal display element after irradiation with ultraviolet rays for 150 seconds was measured. A method for measuring the residual amount of this polymerizable compound will be described. First, the decomposed liquid crystal display element and acetonitrile were placed in a test tube and filtered by shaking 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 high performance liquid chromatography, and the peak area of each component was calculated. The residual amount of the polymerizable compound was determined from the peak area of the liquid crystal compound as an index, the peak area ratio of the unreacted polymerizable compound, and the amount of the initially added polymerizable compound. The detection limit of the residual amount of the polymerizable compound was 100 ppm.

(Evaluation method of pre-tilt angle)
First, the pretilt angle of the liquid crystal cell into which the polymerizable compound-containing liquid crystal composition was injected was measured and used as the pretilt angle (before ultraviolet irradiation). The liquid crystal cell was irradiated with ultraviolet rays for 150 seconds under the above-mentioned irradiation conditions while applying a voltage of 10 V at a frequency of 100 Hz. Then, the pre-tilt angle was measured and used as the pre-tilt angle (after ultraviolet irradiation). The value obtained by subtracting the pretilt angle (after ultraviolet irradiation) from the measured pretilt angle (before ultraviolet irradiation) was defined as the amount of change in pretilt angle [°] due to ultraviolet irradiation. The pre-tilt angle was measured using OPTIPRO manufactured by Shintec.
(VHR evaluation method)
The liquid crystal cell into which the polymerizable compound-containing liquid crystal composition was injected was irradiated with ultraviolet rays for 60 minutes under the above-mentioned irradiation conditions, and VHR was measured. The measurement conditions for VHR were 1 V, 60 Hz, and 60 ° C.

(Evaluation method of burn-in)
The liquid crystal cell into 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 display defects (burn-in) due to changes in the pretilt angle were evaluated. First, the pre-tilt angle of the liquid crystal display element was measured and used as the pre-tilt angle (initial). The liquid crystal display element was irradiated with a backlight for 24 hours while applying a voltage of 30 V at a frequency of 100 Hz. Then, the pre-tilt angle was measured and used as the pre-tilt angle (after the test). The value obtained by subtracting the pretilt angle (after the test) from the measured pretilt angle (initial) was defined as the amount of change in the pretilt angle (= absolute value of the change in the pretilt angle) [°]. The pre-tilt angle was measured using OPTIPRO manufactured by Shintec. The closer the amount of change in the pretilt angle is to 0 [°], the lower the possibility of display defects due to changes in the pretilt angle, and when it is 0.5 [°] or more, display defects due to changes in the pretilt angle occur. More likely.

(Preparation and evaluation results of liquid crystal composition)
Liquid crystal compositions of LC-001 to LC-005 were prepared, and their physical characteristics were measured. Table 1 shows the composition of the liquid crystal composition and the results of its physical property values.

(Table 1)

(Comparative Example 1, Reference Example 4, Examples 11 to 16)
Comparative Example 1 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-R1) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

Reference Example 4 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-2) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

Example 11 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-3) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

Example 12 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-4) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

Example 13 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-5) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

Example 14 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-6) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

Example 15 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-7) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

Example 16 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-8) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Example 1, Reference Example 4 and Examples 11 to 16, the residual amount of the polymerizable compound after ultraviolet irradiation, the amount of change in pretilt angle due to ultraviolet irradiation, the amount of change in pretilt angle in the seizure test, and the amount of change in pretilt angle in the seizure test. The VHR after UV irradiation is shown in Table 2 below.

(Table 2)

In Examples 11 to 16 of the polymerizable compound-containing liquid crystal composition of the present invention, the residual amount of the polymerizable compound after irradiation with ultraviolet rays was smaller than that of Comparative Example 1 and Reference Example 4, and the polymerization rate of the polymerizable compound was sufficient. It turned out to be fast. Further, it was found that the amount of change in the pretilt angle due to ultraviolet irradiation was larger than that in Comparative Example 1 and Reference Example 4, and that the pretilt angle could be formed in a short time. In addition, the VHR after irradiation with ultraviolet rays for 60 minutes was a sufficiently high value. From the above, it was confirmed that the polymerizable compound-containing liquid crystal composition of the present invention has a sufficiently high reaction rate of the polymerizable compound, can form a pretilt angle in a short time, and exhibits a sufficiently high VHR.
(Comparative Example 2, Reference Examples 5 to 6, Examples 17 to 23)
Comparative Example 2 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.3 parts by mass of a compound represented by the formula (RM-A) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-1) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added by 0.03 parts by mass was designated as Reference Example 5.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-2) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added by 0.03 parts by mass was designated as Reference Example 6.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-3) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 17.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-4) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition to which 0.03 part by mass was added was designated as Example 18.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-5) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 19.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-6) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 20.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-7) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition to which 0.03 part by mass was added was designated as Example 21.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-8) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition to which 0.03 part by mass was added was designated as Example 22.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-11) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition to which 0.03 part by mass was added was designated as Example 23.

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Examples 2, Reference Examples 5 to 6 and Examples 17 to 23, the residual amount of the polymerizable compound after ultraviolet irradiation, the amount of change in the pretilt angle due to ultraviolet irradiation, VHR after ultraviolet irradiation, and The amount of change in the pretilt angle in the seizure test is shown in Tables 3 and 4 below.

(Table 3)

(Table 4)

In Examples 17 to 23, 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 is smaller than that of Comparative Examples 2 and 5 to 6, and the polymerization rate of the polymerizable compound is high. It turned out to be fast enough. It was found that the amount of change in the pretilt angle due to ultraviolet irradiation was larger than that in Comparative Examples 2 and 5 to 6, and the pretilt angle could be formed in a short time. It was also confirmed that the VHR after UV irradiation was sufficiently high and the amount of change in the pretilt angle in the seizure test was sufficiently small.
(Comparative Example 3 and Examples 24 to 29)
Comparative Example 3 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.30 parts by mass of a compound represented by the formula (RM-B) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-3) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 24.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-4) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 25.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-5) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added by 0.03 parts by mass was designated as Example 26.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-6) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition to which 0.03 part by mass was added was designated as Example 27.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-7) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 28.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-8) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition to which 0.03 part by mass was added was designated as Example 29.

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Examples 3 and 24 to 29, the residual amount of the polymerizable compound after ultraviolet irradiation, the amount of change in pretilt angle due to ultraviolet irradiation, the change in VHR after ultraviolet irradiation, and the change in pretilt angle in the seizure test. The amounts are shown in Table 5 below.
(Table 5)

It was found that in Examples 24 to 29, 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 was smaller than that in Comparative Example 3, and the polymerization rate of the polymerizable compound was sufficiently high. It was. It was found that the amount of change in the pre-tilt angle due to ultraviolet irradiation showed a value larger than that in Comparative Example 3, and the pre-tilt angle could be formed in a short time. It was also confirmed that the VHR after UV irradiation was sufficiently high and the amount of change in the pretilt angle in the seizure test was sufficiently small.
(Comparative Example 4 and Example 30)
Comparative Example 4 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.30 parts by mass of a compound represented by the formula (RM-C) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-001. And said.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-C) and the compound represented by the formula (RM-3) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 30.

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Examples 4 and 30, the residual amount of the polymerizable compound after ultraviolet irradiation, the amount of change in pretilt angle due to ultraviolet irradiation, the amount of change in VHR after ultraviolet irradiation and the amount of change in pretilt angle in the seizure test were It was as shown in Table 6 below.
(Table 6)

In Example 30, which is the polymerizable compound-containing liquid crystal composition of the present invention, the residual amount of the polymerizable compound after irradiation with ultraviolet rays was smaller than that of Comparative Example 4, and it was found that the polymerization rate of the polymerizable compound was sufficiently high. The amount of change in the pre-tilt angle due to ultraviolet irradiation showed a larger value than in Comparative Example 4, and it was found that the pre-tilt angle could be formed in a short time. It was also confirmed that the VHR after UV irradiation was sufficiently high and the amount of change in the pretilt angle in the seizure test was sufficiently small.
(Examples 31 to 36, Reference Example 7)
With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.25 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-3) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition added by 0.05 parts by mass was designated as Example 31.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.20 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-3) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.1 parts by mass was designated as Example 32.

With respect to 99.6 parts by mass of the liquid crystal composition LC-001, 0.36 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-3) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added by 0.04 parts by mass was designated as Example 33.

A liquid crystal composition containing a polymerizable compound to which 50 ppm of an antioxidant represented by the formula (H-1) was further added to Example 17 was designated as Example 34.

A liquid crystal composition containing a polymerizable compound to which 50 ppm of an antioxidant represented by the formula (H-2) was further added to Example 17 was designated as Example 35.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-9) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 36.

With respect to 99.7 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-A) and the compound represented by the formula (RM-10) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added by 0.03 parts by mass was designated as Reference Example 7.
It was confirmed that Examples 31 to 36 solve the problems of the present invention in the same manner as in Examples 11 to 30.

(Comparative Example 5 and Examples 37 to 38)
Comparative Example 5 is a polymerizable compound-containing liquid crystal composition obtained by adding 0.30 parts by mass of a compound represented by the formula (RM-B) as a polymerizable compound to 99.7 parts by mass of the liquid crystal composition LC-002. And said.

With respect to 99.7 parts by mass of the liquid crystal composition LC-002, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-3) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added in an amount of 0.03 parts by mass was designated as Example 37.

With respect to 99.7 parts by mass of the liquid crystal composition LC-002, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-7) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added by 0.03 parts by mass was designated as Example 38.

Regarding the polymerizable compound-containing liquid crystal compositions of Comparative Examples 5 and 37 to 38, the residual amount of the polymerizable compound after ultraviolet irradiation, the amount of change in pretilt angle due to ultraviolet irradiation, the change in VHR after ultraviolet irradiation, and the change in pretilt angle in the seizure test. The amounts are shown in Table 7 below.
(Table 7)

It was found that in Examples 37 to 38, 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 was smaller than that in Comparative Example 5, and the polymerization rate of the polymerizable compound was sufficiently high. It was. The amount of change in the pre-tilt angle due to ultraviolet irradiation showed a value larger than that in Comparative Example 5, and it was found that the pre-tilt angle could be formed in a short time. Further, it was confirmed that the VHR after UV irradiation was the same as that of Comparative Example 5, and the amount of change in the pretilt angle in the seizure test was sufficiently small.
(Examples 39 to 41)
With respect to 99.7 parts by mass of the liquid crystal composition LC-003, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-7) were used as the polymerizable compound. A liquid crystal composition containing a polymerizable compound added by 0.03 parts by mass was designated as Example 39.

With respect to 99.7 parts by mass of the liquid crystal composition LC-004, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-7) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition to which 0.03 part by mass was added was designated as Example 40.

With respect to 99.7 parts by mass of the liquid crystal composition LC-005, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-7) were used as the polymerizable compound. The polymerizable compound-containing liquid crystal composition to which 0.03 part by mass was added was designated as Example 41.
It was confirmed that Examples 39 to 41 solved the problems of the present invention in the same manner as in Examples 11 to 38.
(Example 42)
With respect to 99.2 parts by mass of the liquid crystal composition LC-001, 0.27 parts by mass of the compound represented by the formula (RM-B) and the compound represented by the formula (RM-3) were used as the polymerizable compound. Example 42 was a liquid crystal composition containing a polymerizable compound in which 0.03 parts by mass and 0.5 parts by mass of the compound represented by the formula (SRM-1) were added.

When the composition of Example 42 was evaluated by the same method except that a liquid crystal cell having no alignment film was used in the above-mentioned method for manufacturing a liquid crystal display element, Example 42 was evaluated in Examples 11 to 11. It was confirmed that the problem of the present invention was solved in the same manner as in 41.

Claims (12)

General formula (I-Np)

(In the formula, X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ are independently hydrogen atom, halogen atom, cyano group, nitro group or alkyl having 1 to 8 carbon atoms. Group or formula (i-Z)

When X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ or X ⁱ⁷ represent an alkyl group, one −CH ₂ − or present in the alkyl group represents the group represented by. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. The hydrogen atom in the alkyl group may be replaced with a fluorine atom, provided that at least one of X ⁱ¹ , X ⁱ² , X ⁱ³ , X ⁱ⁴ , X ⁱ⁵ , X ⁱ⁶ and X ⁱ⁷ . Represents a group represented by the formula (iZ).
^{M i1,} M ⁱ² and ^{M i3} 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 = existing in this group or two or more -CH = not adjacent to each other may be replaced with -N =) and (c). Naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2) , 6-Diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-Diyl group contains one -CH = or two or more non-adjacent -CH = to -N = May be replaced.)
Represents a group selected from the group consisting of, and the above groups (a), groups (b) and groups (c) are independently alkyl groups having 1 to 8 carbon atoms and alkoxy groups having 1 to 8 carbon atoms. It may be replaced with a group, an alkyl halide group having 1 to 8 carbon atoms, an alkoxy halide group having 1 to 8 carbon atoms, a halogen atom, a cyano group, a nitro group or −S ^i3- P ⁱ³ .
L ⁱ¹ and ^{L i2} are each independently a single _{bond, -C 2 H 4 -, -} C 3 H 6 -, - C 4 H 8 -, - OCH 2 -, - CH 2 O -, - CO-, -COO-, -OCO-, -OCOOCH _2- , -CH ₂ OCOO-, -OCH ₂ CH ₂ O-, -CH = CRa-COO-, -CH = CRa-OCO-, -COO-CRa = CH- , -OCO-CRa = CH-, -COO-CRa = CH-COO-, -COO-CRa = CH-OCO-, -OCO-CRa = CH-COO-, -OCO-CRa = CH-OCO-,- _{CH 2 OCO -, - COOCH 2} -, - OCOCH 2 -, - C 2 H 4 OCO -, - C 2 H 4 COO -, - COOC 2 H 4 -, - OCOC 2 H 4 -, - CH = CH- , -CF = CF-, -CF = CH-, -CH = CF-, -CF ₂ O-, -OCF _2- , -CF ₂ CH _2- , -CH ₂ CF _2- , -CF ₂ CF _2- Or -C≡C-, (in the formula, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).
Z ⁱ¹ is a halogen atom, a cyano group, a nitro ^group, an -S i2 ^{-P i2} or an alkyl group having 1 to 8 carbon atoms, the one present in the alkyl group -CH ₂ - or two or more −CH ₂₋ is replaced with −O−, −CH = CH−, −C≡C−, −COO−, −OCO−, −CO− or −S− so that oxygen atoms are not directly adjacent to each other. Also, the hydrogen atom in the alkyl group may be replaced with a fluorine atom,
S ⁱ¹ represents a single bond
S ⁱ² and ^{S i3} are each independently a single bond or an alkylene group having 1 to 15 carbon atoms, one -CH ₂ in the alkylene group - or two or more -CH ₂ -, the oxygen It may be replaced with -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO-, -OCOO- or -S- so that the atoms are not directly adjacent.
P ⁱ¹ , P ⁱ² and P ⁱ³ are independently expressed in equations (R-1) to (R-9).

(In the formula, R ¹¹ , R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ independently represent either 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).
q ⁱ¹ represents 0 or 1, ^mi2 represents 0, 1 or 2,
^{M i1, M i2, L i1} , L i2, Z i1, S i2, S i3, P i2, or if ^{the P i3} there are a plurality, respectively, may have the same or different and
The total number of ^{Pi 1} , ^{Pi 2} and ^{Pi 3} included in the general formula (I-Np) is 2 or 3. )
A liquid crystal composition containing one or more polymerizable compounds represented by. Further general formula (L)

^{(Wherein, R L1} and ^{R L2} are each independently an alkyl group having 1 to 8 carbon atoms, one or two or more -CH ₂ non-adjacent in the alkyl group - each independently Then, it may be replaced by -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-.
n ^L1 represents 0, 1, 2 or 3
A ^L1 , A ^L2, and A ^L3 are independently (a) 1,4-cyclohexylene groups (one -CH _2- existing in this group or two or more -CH ₂ not adjacent to each other. -May be replaced with -O-.)
(B) 1,4-phenylene group (one -CH = existing in this group or two or more -CH = not adjacent to each other may be replaced with -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) , 3,4-Tetrahydronaphthalene-2,6-Diyl One -CH = present in the group or two or more non-adjacent -CH = may be replaced with -N =).
Representing a group selected from the group consisting of, the above group (a), group (b) and group (c) may be independently 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 -, - It represents OCF _2- , -CF ₂ O-, -CH = N-N = CH-, -CH = CH-, -CF = CF- or -C≡C-.
If n ^L1 is 2 or 3 and there are a plurality of A ^L2s , they may be the same or different, and if n ^L1 is 2 or 3 and there are a plurality of Z ^L2s , they may be the same or different. May be the same or different. The liquid crystal composition according to claim 1, which contains one kind or two or more kinds of compounds selected from the compounds represented by). Furthermore, the general formulas (N-1), (N-2) and (N-3)

(In the formula, ^RN11 , ^RN12 , ^RN21 , ^RN22 , ^RN31 and ^RN32 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or non-adjacent of the alkyl groups. of two or more -CH ₂ - are each independently -CH = CH -, - C≡C - , - O -, - CO -, - COO- or -OCO- may be substituted by,
A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are independently (a) 1,4-cyclohexylene groups (one -CH _2- or adjacent to each other in this group). Two or more -CH ₂ − that are not present may be replaced with -O-.)
(B) 1,4-Phenylene group (one -CH = existing in this group or two or more -CH = 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 = existing in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent -CH = may be replaced with -N =. ) And (d) represent a group selected from the group consisting of 1,4-cyclohexenylene groups, and the above groups (a), group (b), group (c) and group (d) are independently cyano. It may be substituted with a group, 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- Represent,
X ^N21 represents a hydrogen atom or a fluorine atom.
^TN31 represents −CH _2- or oxygen atom,
n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, while n ^N11 + n ^N12 , n ^N21 + n ^N22 and n ^N31 + n ^N32 , respectively. Independently, it is 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. However, compounds represented by the general formula (L) are excluded. The liquid crystal composition according to claim 1 or 2, which contains one kind or two or more kinds of compounds selected from the compounds represented by). Further general formula (J)

(In the formula, R ^J1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent −CH ₂ −s in the alkyl group are independently −CH = CH−. , -C≡C-, -O-, -CO-, -COO- or -OCO- may be substituted.
n ^J1 represents 0, 1, 2, 3 or 4
A ^J1 , A ^J2 and A ^J3 are independent of each other.
(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 = existing in this group or two or more -CH = not adjacent to each other may be replaced with -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) , 3,4-Tetrahydronaphthalene-2,6-Diyl One -CH = present in the group or two or more non-adjacent -CH = may be replaced with -N =).
Represents a group selected from the group consisting of, and the above groups (a), group (b) and group (c) are independently cyano groups, fluorine atoms, chlorine atoms, methyl groups, trifluoromethyl groups or trifluoro groups. It may be substituted with a methoxy group,
Z ^J1 and ^{Z J2} are each independently a single _{bond, -CH 2 CH 2 -, -} (CH 2) 4 -, - OCH 2 -, - CH 2 O -, - OCF 2 -, - CF 2 O Represents −, −COO−, −OCO− or −C≡C−
When n ^J1 is 2, 3 or 4 and there are a plurality of A ^J2s , they may be the same or different, and when n ^J1 is 2, 3 or 4 and there are a plurality of Z ^J1s. If so, they may be the same or different,
^XJ1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a 2,2,2-trifluoroethyl group. The 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). Further general formula (P)

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

(In the formula, R ^p11 and R ^p12 independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or an alkyl halide group having 1 to 5 carbon atoms, and W ^p11 is a single bond, −O. Representing a −, −COO− or methylene group, t ^p11 represents 0, 1 or 2, but if there are multiple R ^p11 , R ^p12 , W ^p11 and / or t ^{p11 in} the molecule, they are the same. It may be different or different.)
Represents one of
Sp ^p1 and Sp ^p2 independently represent a single bond or a spacer group, respectively.
Z ^p1 and Z ^p2 are independent, single-bonded, -O-, -S-, -CH _2- , -OCH _2- , -CH ₂ O-, -CO-, -C ₂ H ₄ -,-, respectively. _{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, z are each They independently represent integers 1 to 4, and R ^ZP1 independently represent hydrogen atoms or alkyl groups with 1 to 4 carbon atoms, but if there are multiple R ^ZP1s in the molecule, they are the same. It may be different.)
Represents
A ^p1 , A ^p2 and A ^p3 are independent of each other.
^(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 (the one present in the group -CH = or non-adjacent two or more -CH = may be replaced by -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 -2,6-diyl groups (one -CH = existing in these groups 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 group (a ^p), group (b ^p) and group (c ^p) are each independently hydrogen atoms present in this group may be substituted with a halogen atom, a carbon It may be substituted with an alkyl group having 1 to 8 atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 1 to 8 carbon atoms. It may be substituted with a cyano group, a fluorine atom, a chlorine atom or -Sp ^p2 -P ^p2 .
m ^p1 represents 0, 1, 2 or 3, and when a plurality of Z ^p1 , ^Ap2 , 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 an anthracene-2,6-diyl group.
However, compounds represented by the general formula (I-Np) are excluded. )
The liquid crystal composition according to any one of claims 1 to 4, which contains one or more polymerizable compounds represented by. A liquid crystal display device using the liquid crystal composition according to any one of claims 1 to 5. The liquid crystal display element according to claim 6, for PSA mode, PSVA mode, PS-IPS mode, or PS-FFS mode. The liquid crystal display element according to claim 6 or 7, wherein at least one of the two substrates does not have an alignment film. The liquid crystal display element according to any one of claims 6 to 8, wherein the orientation of the liquid crystal molecules when no voltage is applied is substantially perpendicular to the substrate. General formula (i-Np-1) or general formula (i-Np-2)

^{(Wherein, M in1, M in3, L} in1, S in1, S in2, P in1, P in2 and ^{q in1} is, ^M in the general formula ^{(I-Np) i1, M} i3, L i1, S i1, It has the same meaning as S ⁱ² , P ⁱ¹ , P ⁱ² and q ⁱ¹ , respectively.
X ⁱⁿ¹ , X ⁱⁿ² , X ⁱⁿ³ , X ⁱⁿ⁴ , X ⁱⁿ⁵ , ^Xin6 and ^Xin7 are independently hydrogen atoms, halogen atoms, cyano groups, nitro groups or alkyl groups having 1 to 8 carbon atoms or formulas ( i-nZ)

^Represents a group represented by, and when X ⁱⁿ¹ , X ⁱⁿ² , X ⁱⁿ³ , X ⁱⁿ⁴ , X ⁱⁿ⁵ , X ⁱⁿ⁶ or X ⁱⁿ⁷ represents an alkyl group, one −CH ₂ − or present in the alkyl group. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. The hydrogen atom in the alkyl group may be replaced with a fluorine atom.
M ⁱⁿ² and ^{M in4} each independently represent the same meaning as ^{M i2} in formula (i-Z),
L ⁱⁿ² and ^{L in4} each independently represent the same meaning as ^{L i2} in formula (i-Z),
m ⁱⁿ² and ^{m in4} each independently represent the same meaning as ^{m i2} in formula (i-Z),
Z ⁱⁿ² is halogen atom, a cyano group, a nitro group, -S ⁱⁿ⁴ -P ⁱⁿ⁴ or an alkyl group having 1 to 8 carbon atoms, the one present in the alkyl group -CH ₂ - or two or more −CH ₂₋ is replaced with −O−, −CH = CH−, −C≡C−, −COO−, −OCO−, −CO− or −S− so that oxygen atoms are not directly adjacent to each other. At best, also hydrogen atoms in the alkyl group may be replaced by fluorine atoms, ^{S in4} and ^{P in4} each represent a same meaning as ^{S i2} and ^{P i2} in formula (i-Z),
^{M in1, M in2, M in4} , L in1, L in2, L in4, m in4, ^{if Z} in2, ^{S in4} and ^{P in4} there are a plurality, respectively, may have the same or different and
However, the general formula (i-Np-1) or ^{P in1,} the total number of the number of ^{P in2} and ^{P in4} included in the general formula (i-Np-2) is 2 or 3. )
The compound represented by. General formula (i-Np-1m) or general formula (i-Np-2m)

^{(Wherein, M in1, M in3, L} in1, S in1, S in2 and ^{q in1} has the general formula (I-Np-1) or general formula (I-Np-2) in the ^{M in1, M in3,} L ^{in1, S in1,} respectively ^{S in2} and ^{q in1} the same meaning,
X in ^1m , X in ^2m , X in ^3m , X in ^4m , X in ^5m , X in ^6m and X in ^7m are independently hydrogen atoms, halogen atoms, cyano groups, nitro groups or alkyl groups having 1 to 8 carbon atoms or formulas ( i-nZm)

When X in 1 ^m , X in 2 ^m , X in 3 ^m , X in 4 ^m , X in 5 ^m , X in ^{6 m} or X in ^{7 m} represent an alkyl group, one −CH ₂ − or present in the alkyl group represents the group represented by. For two or more -CH _2- , -O-, -CH = CH-, -C≡C-, -COO-, -OCO-, -CO- or -S- so that oxygen atoms are not directly adjacent to each other. The hydrogen atom in the alkyl group may be replaced with a fluorine atom.
^Min2 , ^Lin2 and ^min2 have the same meanings as ^Min2 , ^Lin2 and the formula ^min2 in the general formula (I-Np-1) or the general formula (I-Np-2), respectively.
M ^{in4, L in4} and ^{m in4} have the same meanings respectively as ^{M in4, L in4} and ^{m in4} in formula (i-nZ),
Y ^im1 , Y ^{im 2} and Y ^im 4 independently represent a hydroxyl group, a protected hydroxyl group or a masked hydroxyl group, a halogen atom, a cyano group, a nitro group, −P ⁱⁿ⁴ or an alkyl group having 1 to 8 carbon atoms. one -CH ₂ present in the alkyl group -, or two or more -CH ₂ -, as the oxygen atoms are not directly adjacent, -O -, - CH = CH -, - C≡C-, It may be replaced with −COO−, −OCO−, −CO− or −S−, and the hydrogen atom in the alkyl group may be replaced with a fluorine atom, provided that at least one of ^Yim1 or ^Yim2 . One represents a hydroxyl group, a protected hydroxyl group or a masked hydroxyl group, and ^Sin4 and ^Pin4 have the same meanings as ^Sin4 and ^Pin4 in the formula ( ^inZ ), respectively.
^{M in1, M in2, M in4} , L in1, L in2, L in4, m in4, ^{if Z} in2, ^{S in4} and ^{P in4} there are a plurality, respectively, may have the same or different and
However, the general formula (i-Np-1m) or ^{Y iim1, Y iim2, Y iim4} and ^P total number of number ⁱⁿ⁴ included in the general formula (i-Np-2m) is 2 or 3. )
The method for producing a compound represented by the general formula (I-Np-1) or the general formula (I-Np-2) according to claim 10, which is produced from the compound represented by. A compound represented by the general formula (i-Np-1m) and the general formula (i-Np-2m) according to claim 11.