JP7006659B2 - Polymerizable monomer, liquid crystal composition using it, and liquid crystal display element - Google Patents

Description

The present invention relates to a novel polymerizable monomer, a liquid crystal composition containing the polymerizable monomer and a spontaneously oriented monomer, and a liquid crystal display element using the same.

In general, a liquid crystal display element such as a liquid crystal panel or a liquid crystal display changes the state of arrangement of liquid crystal molecules by an external stimulus such as an electric field, and uses the change in optical characteristics accompanying the change in the display. Such a liquid crystal display element is configured such that the gap between two transparent substrates is filled with liquid crystal molecules, and the liquid crystal molecules are arranged in advance in a specific direction on the surface of the substrate that comes into contact with the liquid crystal molecules. Generally, an alignment film is formed to form an alignment film.

However, due to the problem of alignment defects caused by scratches and dust on the surface of the alignment film in the manufacturing process of the liquid crystal display element and the increase in the size of the substrate, uniform orientation is achieved over the entire surface of the substrate for a long period of time. There is a problem that it becomes difficult to design and manage the alignment film for obtaining.

Therefore, in recent years, there has been a demand for the development of a liquid crystal display element that does not require an alignment film by using a liquid crystal composition containing a spontaneously oriented material that controls the orientation of liquid crystal molecules in the liquid crystal layer.

For example, in Patent Document 1, instead of lauryl acrylate having a relatively weak interaction with a liquid crystal molecule, a monofunctional biphenyl monomer having an octyl group and showing high linearity and a monofunctional biphenyl monomer having a stearyl group and showing a low straight line are shown. A liquid crystal composition containing a spontaneously oriented material that suppresses a decrease in voltage retention by using a liquid crystal composition containing a functional biphenyl monomer has been described. Further, Patent Document 2 discloses various liquid crystal compositions containing a polymerizable self-alignment additive that controls the orientation of liquid crystal molecules instead of the alignment film, and includes a nematic LC medium, a polymerizable self-alignment additive, and the like. When a liquid crystal composition containing a polymerizable compound, if necessary, is filled into a test cell without an orientation layer, it has a spontaneous homeotropic (vertical) orientation with respect to the substrate surface and this vertical orientation is much more stable up to the transparent point. Yes, it is stated that the formed VA cell can be reversibly switched by applying a voltage.

U.S. Patent Publication No. 2017-0123275 Special Table 2015-168826 Gazette

However, a composition containing two types of hydrophobic monomers having a long alkyl chain and a biphenyl skeleton as shown in Patent Document 1 described above does not interact with the liquid crystal molecules of the liquid crystal layer packed between the pair of substrates. It is considered to be stronger than lauryl acrylate, but there is a problem that the orientation direction of liquid crystal molecules cannot be regulated due to its low adsorption force to the substrate.

Further, in Patent Document 2, since a polymerizable self-oriented additive having a polar group such as a hydroxyl group is used, it is considered that the adsorption force to the substrate is higher than that of the monomer of Patent Document 1. However, if the adsorptive force of the polymerizable self-alignment additive to the substrate is too high, the polymerizable self-alignment additive does not spread uniformly on the substrate, which causes a problem of uneven orientation. Further, a pair of a liquid crystal composition containing a polymerizable compound having a highly symmetric chemical structure as used in Patent Document 2 and a polymerizable self-oriented additive having a polar group such as a hydroxyl group as a liquid crystal layer. In the system filled between the substrates, the liquid crystal layer exhibits hydrophobic properties, and therefore the polymerizable compound exists in the horizontal direction with respect to the substrate from the viewpoint of free energy. There is a problem that it is difficult for the molecule to form a vertical orientation with respect to the substrate. Further, the liquid crystal composition containing the polymerizable self-alignment additive having a polar group such as a hydroxyl group has a problem that the liquid crystal compound and the polymerizable compound are precipitated because the compatibility with the hydrophobic liquid crystal molecule is lowered. Occurs.

Therefore, the problem to be solved by the present invention is to provide a novel polymerizable monomer having excellent vertical orientation and compatibility or a liquid crystal composition having excellent vertical orientation and compatibility, and to display a liquid crystal using the same. The purpose is to provide an element.

As a result of diligent studies by the present inventors, one or more self-oriented polymerizable monomers and one or more polymerizable monomers (or polymerizable compounds) having a specific chemical structure are included. It has been found that the above-mentioned problems can be solved by the liquid crystal composition and the liquid crystal display element using the liquid crystal composition, and the present invention has been completed.

The liquid crystal composition according to the present invention exhibits high compatibility and excellent vertical orientation with respect to liquid crystal molecules.

The liquid crystal composition according to the present invention exhibits excellent expandability (wetting and spreading) with respect to the substrate.

The liquid crystal composition according to the present invention has no orientation unevenness or can reduce orientation unevenness.

The liquid crystal display element according to the present invention exhibits orientation unevenness with no or reduced orientation unevenness.

The polymerizable monomer according to the present invention exhibits high compatibility and excellent vertical orientation with respect to liquid crystal molecules.

The liquid crystal composition containing the polymerizable monomer according to the present invention exhibits excellent expandability (wetting and spreading) with respect to the substrate.

The liquid crystal composition containing the polymerizable monomer according to the present invention has no orientation unevenness or can reduce orientation unevenness.

The figure which shows the evaluation result of the orientation test of the comparative example. The figure which shows the evaluation result of the orientation test of this invention.

The first aspect of the present invention is that the polymerizable monomer represented by the following general formula (I) has a chemical structure different from that of the polymerizable monomer represented by the general formula (I) and has a polar group. A liquid crystal composition comprising an orienting monomer.
Is.

(In the above general formula (I), R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ are independently P ¹¹ -S ¹¹ respectively. -, Represents any of an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom, and P ¹¹ is represented by the following formula (RI) to formula (R-). Represents one of IX)

(In the above formulas (RI) to (R-IX), R ²¹ , R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ are independent of each other and have a hydrogen atom and an alkyl group having 1 to 5 carbon atoms. Alternatively, it is an alkyl halide group having 1 to 5 carbon atoms, W is a single bond, -O- or a methylene group, T is a single bond or -COO-, and p, t and q are independent of each other. It is 0, 1 or 2.)
S ¹¹ represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or more -CH _2- in the alkylene group is -O-, so that oxygen atoms are not directly adjacent to each other. May be substituted with -OCO- or -COO-,
n ¹¹ represents 0, 1 or 2,
A ¹¹ is the following group (a), group (b) and group (c):
(A) 1,4-Cyclohexylene group (one -CH _2- or two or more non-adjacent -CH ₂ -existing in this group may be replaced with -O-).
(B) 1,4-Phenylene group (one -CH = existing in this group or two or more non-adjacent -CH = 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-A single -CH = present in a 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 groups (a), groups (b) and groups (c) are independently alkyl groups having 1 to 12 carbon atoms and 1 to 12 carbon atoms, respectively. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or ^P11 - ^S11- .
L ¹⁰ and L ¹¹ are independently single-bonded, -OCH _2- , -CH ₂ O-, -C ₂ H _4- , -OC ₂ H ₄ O-, -COO-, -OCO-,-, respectively. CH = CR ^a -COO-, -CH = CR ^a -OCO-, -COO-CR ^a = CH-, -OCO-CR ^a = CH-,-(CH ₂ ) _z -COO-,-(CH ₂ ) _z -OCO-, -OCO- (CH ₂ ) _z- , -COO- (CH ₂ ) _z- , -CH = CH-, -CF ₂ O-, -OCF _2- or -C≡C- (in the formula) , Ra independently represent ^a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and z in the above formula independently represent an integer of 1 to 4).
It has at least two or more P ¹¹ -S ¹¹ -in one molecule of the above general formula (I), and has.
One molecule of the above general formula (I) has an alkyl group having 1 to 18 carbon atoms, and one or _two or more non-adjacent alkyl groups in the alkyl group are independently of each other. May be replaced by O-
When a plurality of P ¹¹ , S ¹¹ , L ¹⁰ , L ¹¹ and A ¹¹ exist, they may be the same or different from each other. )
As a result, a liquid crystal composition that imparts excellent vertical orientation to liquid crystal molecules and has excellent compatibility is provided. In addition, the liquid crystal composition can vertically orient liquid crystal molecules without requiring an alignment film.

In the above general formula (I), A ¹¹ represents a group selected from the group consisting of the following groups (a) to (c), and the following groups (a), groups (b) and groups (c) are respectively. Independently, it may be substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to ¹² carbon atoms, a halogen, a cyano group, a nitro group or P11- ^S11- .
(A) 1,4-Cyclohexylene group (one -CH _2- or two or more non-adjacent -CH ₂ -existing in this group may be replaced with -O-).
(B) 1,4-Phenylene group (one -CH = existing in this group or two or more non-adjacent -CH = 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-A single -CH = present in a diyl group or two or more non-adjacent -CH = may be replaced with -N =).
In the above general formula (I), A ¹¹ is substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogen, a cyano group, a nitro group or P ¹¹ -S ^11- . It may be a 1,4-phenylene group or a naphthalene-2,6-diyl group, preferably an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogen, a cyano group, or a nitro group. It is more preferably a 1,4-phenylene group which may be substituted with a group or P ¹¹ -S ^11- .

In the above general formula (I), L ¹⁰ is a single bond, -OCH _2- , -CH ₂ O-, -C ₂ H _4- , -COO-, -OCO-, -CH = CH-COO-,- CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -C ₂ H ₄ -COO-, -C ₂ H ₄ -OCO-, -OCO-C ₂ H _4- , -COO-C ₂ H _4- , -CH = CH-, -CF ₂ O-, -OCF _2- or -C≡C- is preferable, and single bond, -OCH _2- , -CH ₂ O-, -C ₂ H 4-, -COO-, -OCO-, -C ₂ H ₄ -COO-, -C ₂ H ₄ -OCO-, -OCO-C ₂ H _4- , -COO _{-C 2 H 4 - ,} - CF ₂ O-, -OCF _2- or -C≡C- are more preferable, and a single bond is particularly preferable.

Since the above-mentioned linking group L ¹⁰ is an even-numbered link and the molecule is linear, it is easy to be familiar with the liquid crystal molecule.

In the above general formula (I), L ¹¹ is a single bond, -OCH _2- , -CH ₂ O-, -C ₂ H _4- , -COO-, -OCO-, -CH = CH-COO-,-. CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -C ₂ H ₄ -COO-, -C ₂ H ₄ -OCO-, -OCO-C ₂ H _4- , -COO-C ₂ H _4- , -CH = CH-, -CF ₂ O-, -OCF _2- or -C≡C- is preferable, and single bond, -OCH _2- , -CH ₂ O-, -C ₂ H 4-, -COO-, -OCO-, -C ₂ H ₄ -COO-, -C ₂ H ₄ -OCO-, -OCO-C ₂ H _4- , -COO _{-C 2 H 4 - ,} - CH = CH-, -CF ₂ O-, -OCF _2- or -C≡C- are more preferable, and a single bond is particularly preferable.

Since the above-mentioned linking group L ¹¹ is an even-numbered link and the molecule is linear, it is easy to be familiar with the liquid crystal molecule.

In the above general formula (I), L ¹⁰ and L ¹¹ may be the same or different from each other, but it is more preferable that L ¹⁰ and L ¹¹ are the same.

In the above general formula (I), R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ are independently P ¹¹ -S ^11- , respectively. It represents any of an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom, and in this case, the preferred number of carbon atoms of the alkyl group and the alkoxy group is that of the liquid crystal. When orientation is important, 10 to 18 is preferable, and when solubility in a liquid crystal compound is important, 1 to 4 is preferable. Further, the alkyl group and the alkoxy group may be linear or branched, but linear is particularly preferable.

Further, when at least one or more of R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ represent an alkyl group having 1 to 18 carbon atoms. The preferable number of carbon atoms of the alkyl group is preferably 10 to 18 when the orientation of the liquid crystal is important, and 1 to 4 when the solubility in the liquid crystal compound is important. Further, the alkyl group may be linear or branched, but linear is particularly preferable.

In the above general formula (I), R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ are independently P ¹¹ -S ^11- , respectively. It is preferable to represent an alkyl group having 1 to 10 carbon atoms, a halogen atom or a hydrogen atom, and P11- ^S11- , an alkyl group having ¹ to 3 carbon atoms, a fluorine atom or a hydrogen atom. It is more preferable to represent it. From the standpoint of solubility, the alkyl chain should not be too long.

It has at least two or more P ¹¹ -S ¹¹ -in one molecule of the polymerizable monomer represented by the general formula (I). It is preferable that the polymerizable monomer represented by the general formula (I) has two or more polymerizable groups from the viewpoint of the crosslinking density.

In the above general formula (I), at least two or more of P ¹¹ -S ¹¹ among R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ . -It is preferable to have 2 to 4 P ¹¹ -S ^11- , and it is further preferable to have 2 to 3 P ¹¹ -S ^11- .

The polymerizable monomer represented by the general formula (I) preferably has 1 to 4 polymerizable groups on the outer portion of the mesogen skeleton from the viewpoint of polymerizable properties.

That is, the polymerizable monomer represented by the general formula (I) has at least two or more P ¹¹ -S ¹¹ -in one molecule. In this case, (1) A ¹¹ is provided with two or more P ¹¹ -S ^11- , and (2) A ¹¹ is provided with one or more P ¹¹ -S ^11- , and R ¹⁰¹ and R are provided. One of ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ , with at least one P ¹¹ -S ^11- , and (3). Any of R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ , with at least two P ¹¹ -S ^11- . It can be divided into three parts.

In the above general formula (I), (1) when A ¹¹ has two or more P ¹¹ − S ¹¹ −, the A ¹¹ is preferably a 6-membered ring group, and P at the 2nd and 5th positions. A structure in which ¹¹ -S ^11- is substituted is preferable, and a structure in which A ¹¹ is a 1,4 phenylene group and P ¹¹ -S ¹¹ -is substituted at the 2- and 5-positions is more preferable. ..

In the above general formula (I), (2) A ¹¹ comprises 1 or more P ¹¹ -S ¹¹ -and R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , In any of R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ , in the form of having at least one P ¹¹ -S ^11- , A ¹¹ is the base of the 6-membered ring and is the ⁶ -membered ring. A structure in which one of the 2nd and 3rd positions of the above has P ¹¹ -S ¹¹ -and the R ¹⁰¹ or R ¹¹⁰ has P ¹¹ -S ¹¹ -is preferable.

In the above general formula (I), in any one of (3) R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ , two or more Ps. A preferred embodiment comprising ¹¹ -S ¹¹ -is a structure in which R ¹⁰¹ and R ¹¹⁰ are P ¹¹ -S ^11- (P ¹¹ and S ¹¹ may be the same or different, respectively). A structure in which R ¹⁰¹ and R ¹⁰⁷ are P ¹¹ -S ^11- (P ¹¹ and S ¹¹ may be the same or different, respectively), and R ¹⁰⁸ and R ¹¹⁰ are P ¹¹ -S ^11- . The structure (P ¹¹ and S ¹¹ may be the same or different from each other) and the like can be mentioned.

When R ¹⁰¹ and R ¹¹⁰ are P ¹¹ -S ^11- , it is preferable from the viewpoint of solubility in the liquid crystal compound.

As a preferable form in which three P ¹¹ -S ¹¹ -are provided in one molecule of the polymerizable monomer represented by the general formula (I), R ¹⁰¹ , R ¹¹⁰ and R ¹⁰⁷ are P ¹¹ -S ^11- . The structure (P ¹¹ and S ¹¹ may be the same or different, respectively) and the structure in which R ¹⁰¹ , R ¹¹⁰ and R ¹⁰² are P ¹¹ -S ^11- (P ¹¹ and S ¹¹ are P 11 and S 11 respectively). (It may be the same or different), and A ¹¹ is the base of the 6-membered ring, and one of the 2- and 3-positions of A ¹¹ which is the 6-membered ring has P ¹¹ -S ^11- . Further, there is a structure in which R ¹⁰¹ and R ¹¹⁰ are P ¹¹ -S ^11- .

As a preferable form in which four P ¹¹ -S ¹¹ -are provided in one molecule of the polymerizable monomer represented by the general formula (I), R ¹⁰² , R ¹⁰⁴ , R ¹⁰⁷ and R ¹⁰⁹ are P ¹¹ -S ¹¹ . -A structure (P ¹¹ and S ¹¹ may be the same or different, respectively) and R ¹⁰² , R ¹⁰⁴ and R ¹⁰⁷ are P ¹¹ -S ¹¹ -and are 6-membered rings. Examples thereof include a structure in which one of the 2nd and 3rd positions of A ¹¹ has P ¹¹ -S ^11- .

Needless to say, when a plurality of P ^{11 and S 11 exist as described above, P 11 and S 11} may be the same or different from each other.

One molecule of the above general formula (I) has at least one alkyl group having 1 to 18 carbon atoms, and one or _two or more non-adjacent alkyl groups in the alkyl group are independent of each other. Then, it may be replaced by —O—.

As a result, the long-chain alkyl group faces the hydrophobic liquid crystal layer side, and the liquid crystal molecules follow the same direction in the direction perpendicular to the substrate, which has the effect of improving the vertical orientation.
Alkyl group having 1 to 18 carbon atoms in one molecule of the polymerizable monomer represented by the general formula (I) (one in the alkyl group or two or more non-adjacent −CH ₂ ). — May be independently substituted with —O—), preferably an alkyl group having 1 to 18 carbon atoms or an alkoxy group having 1 to 18 carbon atoms. More preferably, it is an alkyl group having 1 to 18 carbon atoms.
When the polymerizable monomer represented by the general formula (I) has one or more alkyl groups in one molecule, the alkyl moiety is easily compatible with the hydrophobic liquid crystal and is arranged in a brush shape toward the liquid crystal layer side. , It is preferable because the liquid crystal molecules are vertically oriented accordingly.

Further, an alkyl group having 1 to 18 carbon atoms having one or more in one molecule of the polymerizable monomer represented by the general formula (I) (one in the alkyl group or two or more non-adjacent ones- CH _2- may be independently substituted with —O—.) Preferred forms include linear or branched, preferably linear. Further, the preferable number of carbon atoms of the alkyl group is preferably 1 to 3 when the solubility and expandability of the liquid crystal composition are emphasized. On the other hand, when the vertical orientation with respect to the liquid crystal molecules is emphasized, 10 to 19 are preferable.

In one molecule of the polymerizable monomer represented by the general formula (I), one or two alkyl groups having 1 to 18 carbon atoms (one in the alkyl group or two or more non-adjacent alkyl groups- CH ₂ -may be independently substituted with —O—).

It is preferable from the viewpoint of orientation that one molecule of the polymerizable monomer represented by the general formula (I) has one or two alkyl groups having 1 to 18 carbon atoms.

In one molecule of the polymerizable monomer represented by the above general formula (I), one alkyl group having 1 to 18 carbon atoms (one in the alkyl group or _two or more non-adjacent-CH2-). Can be independently substituted by —O—), either at the 2nd or 3rd position of R ¹⁰² , R ¹⁰³ , R ¹⁰⁶ , R ¹⁰⁷ and A ¹¹ which is a 6-membered ring. Is preferable. Further, in one molecule of the polymerizable monomer represented by the general formula (I), two alkyl groups having 1 to 18 carbon atoms (one in the alkyl group or two or more non-adjacent ones- CH ₂ -may be independently substituted with —O—), the combination of the positions of the two alkyl groups is R ¹⁰² and R ¹⁰⁴ , R ¹⁰³ and R ¹⁰⁵ , R ¹⁰² . And R ¹⁰³ , R ¹⁰⁶ and R ¹⁰⁸ , R ¹⁰⁷ and R ¹⁰⁹ , or a combination of R ¹⁰⁶ and R ¹⁰⁷ is preferred, R ¹⁰² and R ¹⁰⁴ , R ¹⁰³ and R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁸ or R ¹⁰⁷ and R ^109. The combination of is more preferable.

In the above general formula (I), n ¹¹ represents 0, 1 or 2, n ¹¹ is preferably 0 or 1, and n ¹¹ is more preferably 0.

Further, in the above general formula (I), when n ¹¹ is 2, L ¹¹ and A ¹¹ may be the same or different from each other.

The compound represented by the general formula (I) has a structure in which two benzene rings and, if necessary, ring A ¹¹ are linked, and P ¹¹ -S ¹¹ -is at least 2 in these two benzene rings and ring A ¹¹ . Therefore, the compound represented by the general formula (I) has an action / effect as a polymerizable monomer.

In the general formula (I), P ¹¹ represents any of the following formulas (RI) to (R-IX).

(In the above formulas (RI) to (R-IX), R ²¹ , R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ are independent of each other and have a hydrogen atom and an alkyl group having 1 to 5 carbon atoms. Alternatively, it is an alkyl halide group having 1 to 5 carbon atoms, W is a single bond, -O- or a methylene group, T is a single bond or -COO-, and p, t and q are independent of each other. It is 0, 1 or 2.)
Of these, in the above general formula (I), P ¹¹ is independently represented by the formula (R-1), the formula (R-2), the formula (R-3), the formula (R-4), and the formula (R). -5) or formula (R-7) is preferable, and formula (R-1), formula (R-2), formula (R-3) or formula (R-4) is more preferable. The formula (R-1) is more preferable, an acrylic group or a methacrylic group is more preferable, and a methacrylic group is even more preferable.

In the general formula (I), S ¹¹ is preferably a single bond or an alkylene group having 1 to 3 carbon atoms, and more preferably a single bond.

The lower limit of the content of the polymerizable monomer represented by the general formula (I) in the liquid crystal composition of the present invention is preferably 0.02% by mass, preferably 0.03% by mass, and preferably 0.04% by mass. 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, 0.1% by mass is preferable, and 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, 0.25% by mass is preferable, and 0.27% by mass is preferable. % 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, 0.4% by mass is preferable, and 0.42% by mass is preferable. It is preferably 0.45% by mass, preferably 0.5% by mass, and preferably 0.55% by mass. 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 2.5% by mass, preferably 2.3% by mass, and preferably 2.1% by mass. 2% by mass is preferable, 1.8% by mass is preferable, 1.6% 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. Preferably, 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. 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.

The liquid crystal composition according to the present invention contains one or more kinds of polymerizable monomers represented by the general formula (I), and 1 to 5 kinds of polymerizable monomers represented by the general formula (I). It is preferable to include 1 to 4 kinds of polymerizable monomers represented by the general formula (I), and preferably 1 to 3 kinds of polymerizable monomers represented by the general formula (I). Is preferable. In another embodiment, from the viewpoint of improving vertical orientation and uneven orientation, it is preferable to include 2 to 5 types of polymerizable monomers represented by the general formula (I), and 2 to 4 types of general. It preferably contains a polymerizable monomer represented by the formula (I).

The preferred form of the polymerizable monomer represented by the general formula (I) according to the present invention is preferably represented by the general formula (Ia).

(In the above general formula (Ia), R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ and R ¹⁰⁹ are independently from P ¹¹ -S ^11- and the number of carbon atoms is 1. It represents an alkyl group of 18, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom, and P ¹¹ represents any of the following formulas (RI) to (R-IX). ,

(In the above formulas (RI) to (R-IX), R ²¹ , R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ are independent of each other and have a hydrogen atom and an alkyl group having 1 to 5 carbon atoms. Alternatively, it is an alkyl halide group having 1 to 5 carbon atoms, W is a single bond, -O- or a methylene group, T is a single bond or -COO-, and p, t and q are independent of each other. It is 0, 1 or 2.)
S ¹¹ represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or more -CH _2- in the alkylene group is -O-, so that oxygen atoms are not directly adjacent to each other. May be substituted with -OCO- or -COO-,
At least one of R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ and R ¹⁰⁹ is an alkyl group having 1 to 18 carbon atoms and an alkoxy group having 1 to 18 carbon atoms. However, the plurality of P ¹¹ and S ¹¹ may be the same or different from each other. )
In the above general formula (Ia), it is preferable that any one of R ¹⁰² , R ¹⁰³ , R ¹⁰⁶ , and R ¹⁰⁷ is an alkyl group having 1 to 18 carbon atoms or an alkoxy group having 1 to 18 carbon atoms. Further, in the above general formula (Ia), when two alkyl groups having 1 to 18 carbon atoms or an alkoxy group having 1 to 18 carbon atoms are provided, the combination of the positions of the two alkyl groups is R. A combination of ¹⁰² and R ¹⁰⁴ , R ¹⁰³ and R ¹⁰⁵ , R ¹⁰² and R ¹⁰³ , R ¹⁰⁶ and R ¹⁰⁸ , R ¹⁰⁷ and R ¹⁰⁹ , or R ¹⁰⁶ and R ¹⁰⁷ is preferred, with R ¹⁰² and R ¹⁰⁴ , R ¹⁰³ and R being preferred. A combination of ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁸ or R ¹⁰⁷ and R ¹⁰⁹ is more preferred.

In the above general formula (Ia), P ¹¹ is independently represented by the formula (R-1), the formula (R-2), the formula (R-3), the formula (R-4), and the formula (R-5). ) Or formula (R-7), more preferably formula (R-1), formula (R-2), formula (R-3) or formula (R-4), and formula (R-4). R-1) is more preferable, an acrylic group or a methacrylic group is more preferable, and a methacrylic group is even more preferable. Further, the two or more P ^11s of the above general formula (Ia) may be the same or different, but are preferably the same.

In the above general formula (Ia), S ¹¹ is preferably a single bond or an alkylene group having 1 to 3 carbon atoms, and more preferably a single bond. Further, the two or more ^S11s of the above general formula (Ia) may be the same or different, but are preferably the same.

The preferred embodiments of the alkyl group having 1 to 18 carbon atoms and the alkoxy group having 1 to 18 carbon atoms are the same as those in the general formula (I).

The lower limit of the content of the polymerizable monomer represented by the general formula (Ia) in the liquid crystal composition of the present invention is preferably 0.02% by mass, preferably 0.03% by mass, and preferably 0.04% by mass. 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, 0.1% by mass is preferable, and 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, 0.25% by mass is preferable, and 0.27% by mass is preferable. % 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, 0.4% by mass is preferable, and 0.42% by mass is preferable. It is preferably 0.45% by mass, preferably 0.5% by mass, and preferably 0.55% by mass. 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 2.5% by mass, preferably 2.3% by mass, and preferably 2.1% by mass. 2% by mass is preferable, 1.8% by mass is preferable, 1.6% 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. Preferably, 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. 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.

The liquid crystal composition according to the present invention preferably contains one kind or two or more kinds of polymerizable monomers represented by the general formula (Ia). The type of the polymerizable monomer represented by the general formula (Ia) contained in the liquid crystal composition according to the present invention is 1 to 5 types, 1 to 4 types, 1 to 3 types, and 1 to 2 types. Is preferable. In another embodiment, it is preferable to include 2 to 5 types, 2 to 4 types, and 2 to 3 types from the viewpoint of improving vertical orientation and alignment unevenness.

Suitable compounds of the polymerizable monomer represented by the general formula (I) according to the present invention include the following formulas RM-1 to RM-75-6.

In the above formula, ^RM1 , ^RM2 and ^RM3 independently represent either an alkyl group having 1 to 5 carbon atoms, a fluorine atom or a hydrogen atom, and each of them has an alkyl group having 1 carbon atom or hydrogen. It is more preferable to represent an atom.

The above formulas RM-1 to RM-66 are preferable, and RM-2 to RM-4, RM-16 to RM-18, RM-20 to RM-26, RM-30 to RM-32, RM-34 to RM- 36, RM-38, RM-42, RM-45 to RM-48, RM-50 and RM-55 to RM-57 are more preferred, with RM-2 to RM-4 and RM-16 to RM-18. More preferred.

The liquid crystal composition according to the present invention essentially contains a spontaneously oriented monomer that controls the orientation of liquid crystal molecules. Further, the spontaneously oriented monomer has at least one polar group and has a chemical structure different from that of the polymerizable monomer represented by the general formula (I) according to the present invention.
It is preferable that the polar group has a role of an adsorption site that adsorbs to the substrate, the membrane, and the electrode.

The polar group of the spontaneously oriented monomer according to the present invention is preferably one or more selected from the group consisting of the following formulas (K-1) to (K-28).

(In the above formulas (K-1) to (K-23), ^RK1 and ^RK2 independently represent a hydrogen atom or a linear or branched alkyl group or alkyloxy group having 1 to 5 carbon atoms. , ^RK3 represents a hydrogen atom or a linear or branched alkyl group of 1 to 20 and one or two or more non-adjacent -CH _2- in this alkyl group is -O-, -COO- or-. It may be substituted with OCO-, and ^RK4 and ^RK5 each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and W ^K1 is a methine group, ≡C- _CH3 , ≡C. -C ₂ H ₅ , ≡ C-C ₃ H ₇ , ≡ C-C ₄ H ₉ , ≡ C-C ₅ H ₁₁ , ≡ C-C ₆ H ₁₃ or a nitrogen atom, where X ^K1 and X ^{K 2} are respectively. Independently, -CH _2- , oxygen atom, -C (= O)-or sulfur atom, Y ^K1 , Y ^K2 and Y ^K3 independently represent a methine group or a nitrogen atom, and Z ^K1 is. Z K2 represents an oxygen atom or a sulfur atom, Z ^K2 represents a carbon atom or a silicon atom, Z ^K 3 represents an oxygen atom, and Z ^K 4 represents a single bond or a double bond.)

(In the formula, Y ⁱ¹ represents a linear or branched alkyl group having 3 to 20 carbon atoms, a halogenated alkyl group or a cyanated alkyl group, and at least two or more secondary carbons in these alkyl groups. The atom is substituted with-(C = X ⁱ¹ )-and / or-(CH-CN)-and the secondary carbon atom in the alkyl group is -CH = so that the oxygen atom is not directly adjacent. It may be substituted with CH-, -C≡C-, -O-, -NH-, -COO- or -OCO-, where X ⁱ¹ represents an oxygen atom, a sulfur atom, NH or NR ^il .
S ⁱ¹ and S ⁱ³ independently represent an alkylene group or a single bond having 1 to 6 carbon atoms, and -CH _2- in the alkylene group is -CH = CH-,-so that oxygen atoms are not directly adjacent to each other. C≡C-, -C (= CH ₂ )-, -C (= CHR ⁱ³ )-, -C (= CR ⁱ³ ₂ )-, -O-, -NH-, -C = O-, -COO- Alternatively, it may be replaced with -OCO-.
S ⁱ² represents a carbon atom, a nitrogen atom or a silicon atom, and represents
R ⁱ² represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, and the secondary carbon atom in these groups is -O-, -CH = CH so that the oxygen atom is not directly adjacent to each other. It may be replaced with-or -C≡C-.
P ⁱ¹ represents a polymerizable group and represents
Sp ⁱ¹ represents a spacer group or a single bond.
n ⁱ¹ represents an integer of 1 to 3, n ⁱ² and n ⁱ³ each independently represent an integer of 0 to 2, but when S ⁱ² represents a carbon atom or a silicon atom, n ⁱ¹ + n ⁱ² + n ⁱ³ is 3 When S ⁱ² represents a nitrogen atom, n ⁱ¹ + n ⁱ² + n ⁱ³ is 2. R ⁱ³ has the same meaning as R ⁱ³ in the general formula (i), and there are a plurality of R ⁱ² , X ⁱ¹ , Y ⁱ¹ , S ⁱ¹ , S ^{i 3} , ^{Pi 1} and Sp ⁱ 1 in the general formula (K-1). If so, they may be the same or different. )

(In the formula, S ⁱ¹ , P ^{i 1} and S p i ¹ have the same meanings as S ^{i 1} , P ^{i 1} and S p i 1 in the general formula ( ^{K-1), respectively, and RK21 is} a linear or linear chain having 1 to 10 carbon atoms. Represents a branched alkyl group, halogenated alkyl group or cyanated alkyl group, and at least two or more secondary carbon atoms in these alkyl groups are -CH = CH-, -C so that oxygen atoms are not directly adjacent to each other. It may be replaced with ≡C-, -O-, or -NH-, and ⁿⁱ⁴ and ^niK21 independently represent 0 or 1, respectively.)
The spontaneously oriented monomer according to the present invention has at least one polar group, a mesogen group, and at least one polymerizable group, and is a polymerizable monomer represented by the general formula (I) according to the present invention. It has a different chemical structure from. The polar group may be attached to a mesogen group or a polymerizable group via a spacer.

The spacer preferably represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or more -CH _2- in the alkylene group is such that oxygen atoms are not directly adjacent to each other. It may be substituted with —O—, —OCO— or —COO—.

The mesogen group has a general formula (mes):

(In the formula, Z ^me1 is a single bond, -CH = CH-, -CF = CF-, -C≡C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF ₂ O- , -OCF _2- , -CH = CHCOO-, -OCOCH = CH-, -CH ₂ -CH ₂ COO-, -OCOCH ₂ -CH _2- , -CH = C (CH ₃ ) COO-, -OCOC (CH) ₃ ) = CH-, -CH ₂ -CH (CH ₃ ) COO-, -OCOCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-, or an alkylene group having 2 to 20 carbon atoms. One or two or more non-adjacent -CH _2- in this alkylene group may be substituted with -O-, -COO- or -OCO-, except that if ^Ki1 is (K-11), it is a mesogen. Based on at least -CH ₂ -CH ₂ COO-, -OCOCH ₂ -CH _2- , -CH = C (CH ₃ ) COO-, -OCOC (CH ₃ ) = CH-, -CH ₂ -CH (CH ₃ ) Includes any one of COO-, -OCOCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-
A ^me1 represents a divalent 6-membered ring aromatic group, a divalent 6-membered ring heteroarophatic group, a divalent 6-membered ring aliphatic group, and a divalent 6-membered ring heteroaliphatic group. The hydrogen atom in the ring structure may be substituted with a halogen atom, ^P11 - ^S11- , and a polar group. When a plurality of Z ^me1 and A ^me1 exist, they may be the same or different from each other. ^Mme1 represents an integer of 1 to 5, and the black dot at the left end and the black dot in the formula (me). The black dot at the right end represents the bond. )
The spontaneously oriented monomer according to the present invention is one or two selected from the group consisting of compounds represented by the general formula (i), the general formula (ii), the general formula (iii) and the general formula (iv). The above compounds are preferable.

(In the above general formula (i), R ^al1 , R ^al2 , Z ^al1 , Z ^al2 , L ^al1 , L ^al2 , L ^al3 , Sp ^al1 , Sp ^al2 , Sp ^al3 , X ^al1 , X ^al2 , X ^al3 , ^mal1 , ^Mal2 , ^mal3 , ^nal1 , ^nal2 , ^nal3 , ^pal1 and ^pal2 are independent of each other, respectively.
R ^al1 represents a linear, branched or cyclic alkyl having a hydrogen atom, a halogen atom and 1 to 20 carbon atoms, where one or more non-adjacent CHs in the alkyl group. The _two groups are formed by -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O- so that O and / or S atoms do not bond directly to each other. It may be substituted, and one or more hydrogen atoms may be substituted by F or Cl.
R ^al2 represents a group having any of the following partial structures:

Sp ^al1 , Sp ^al2 and Sp ^al3 are independent of each other and represent an alkyl group or a single bond having 1 to 12 carbon atoms.
X ^al1 , X ^al2 and X ^al3 each independently represent an alkyl group, an acrylic group, a methacrylic group or a vinyl group, respectively.
Z ^al1 is -O-, -S-, -CO-, -CO-O-, -OCO-, -O-CO-O-, -OCH _2- , -CH ₂ O-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF ₂ -,-(CH ₂ ) _n ^al- , -CF ₂ CH _2- , -CH ₂ CF _2- ,-(CF ₂ ) _n ^al- , -CH = CH-, -CF = CF-, -C≡C-, -CH = CH-COO-, -OCO-CH = CH-,-(CR ^al3 R ^al4) ) _N ^a1- , -CH (-Sp ^al1- X ^al1 )-, -CH ₂ CH (-Sp ^al1- X ^al1 )-, -CH (-Sp ^al1- X ^al1 ) CH (-Sp ^al1- X ^al1 ) -Indicates
Z ^al2 are independent of each other, single bond, -O-, -S-, -CO-, -CO-O-, -OCO-, -O-CO-O-, -OCH _2- , -CH ₂ O-, -SCH 2-, -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF ₂ -,-(CH ₂ ) _n1- , -CF ₂ CH _2- , -CH ₂ CF ₂ -,-(CF ₂ ) _n ^al- , -CH = CH-, -CF = CF-, -C≡C-, -CH = CH-COO-, -OCO-CH = CH- ,-(CR ^al3 R ^al4 ) _na1- , -CH (-Sp ^al1- X ^al1 )-, -CH ₂ CH (-Sp ^al1- X ^al1 )-, -CH (-Sp ^al1 -X ^al1 ) CH (- Sp ^al1 -X ^al1 )-is shown.
L ^al1 , L ^al2 , and L ^al3 are independent of each other, and hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, -CN, -NO ₂ , -NCO, -NCS, -OCN, -SCN,- C (= O) N (R ^al3 ) ₂ , -C (= O) R ^al3 , an arbitrarily substituted silyl group having 3 to 15 carbon atoms, an arbitrarily substituted aryl group or cycloalkyl group or It represents 1 to 25 carbon atoms, where one or more hydrogen atoms may be replaced by halogen atoms (fluorine atoms, chlorine atoms).
The R ^al 3 represents an alkyl group having 1 to 12 carbon atoms, the R ^al 4 represents an alkyl group having a hydrogen atom or 1 to 12 carbon atoms, and the n ^al represents an alkyl group having 1 to 12 carbon atoms. Represents an integer
p ^al1 and ^pal2 are independent of each other and represent 0 or 1, and ^mal1 , ^mal2 and ^mal3 are independent of each other and represent integers from 0 to 3, where n ^al1 , n ^al2 and n ^al3 are. Representing an integer from 0 to 3 independently of each other. )
General formula (ii):

(In the formula, Z ⁱⁱ¹ is a single bond, -CH = CH-, -CF = CF-, -C≡C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF ₂ O- , -OCF _2- , -CH = CHCOO-, -OCOCH = CH-, -CH ₂ -CH ₂ COO-, -OCOCH ₂ -CH _2- , -CH = C (CH ₃ ) COO-, -OCOC (CH) ₃ ) = CH-, -CH ₂ -CH (CH ₃ ) COO-, -OCOCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-, or an alkylene group having 2 to 20 carbon atoms. One or two or more non-adjacent -CH _2- in this alkylene group may be substituted with -O-, -COO- or -OCO-, except that if ^Ki1 is (K-11), it is a mesogen. Based on at least -CH ₂ -CH ₂ COO-, -OCOCH ₂ -CH _2- , -CH = C (CH ₃ ) COO-, -OCOC (CH ₃ ) = CH-, -CH ₂ -CH (CH ₃ ) Includes any one of COO-, -OCOCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-
A ⁱⁱ¹ represents a divalent 6-membered ring aromatic group, a divalent 6-membered ring heteroaromatic group, a divalent 6-membered ring aliphatic group, and a divalent 6-membered ring complex aliphatic group. The hydrogen atom in the ring structure may be substituted with a halogen atom or a monovalent organic group having a substituent represented by P ⁱ¹ -Sp i1- and a substituent represented by the general formula K ^{i 1} , or R ^{i 1} , but at least one. Is replaced by P ⁱ¹ -Sp ^i1-
When a plurality of Z ⁱⁱ¹ and A ⁱⁱ¹ exist, they may be the same or different from each other.
^mii1 represents an integer from 1 to 5.
R ⁱⁱ¹ and R ⁱⁱ² independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, an alkyl halide group, or P ⁱ¹ -Sp ^i1- , and-in the alkyl group. CH _2- may be replaced with -CH = CH-, -C≡C-, -O-, -NH-, -COO- or -OCO-, but -O- is not continuous and R ⁱⁱ¹ And R ⁱⁱ² represent a monovalent organic group having a substituent represented by K ⁱ¹ , and having one or more P ⁱ¹ -Sp ^i1- in the general formula (ii). It has a monovalent organic group having one or more substituents represented by K ⁱ¹ and one or more R ^i1s . However, when K ⁱ¹ is (K-11), Z ⁱⁱ¹ is -CH ₂ -CH ₂ COO-, -OCOCH ₂ -CH _{2-, -CH 2 -} CH (CH ₃ ) COO-, -OCOCH (CH). ₃ ) -A compound represented by "CH _2- , -OCH ₂ CH ₂ O-" (hereinafter, also referred to as "compound (ii)").
The above P ⁱ¹ -Sp ^{i1- (P i1 represents} a polymerizable group, and represents a substituent selected from the group represented by the following general formulas (P-1) to (P-15) (in the formula). , The black dot on the right end represents the bond.),

Sp ⁱ¹ represents a spacer group. ), A monovalent organic group having a substituent represented by K ⁱ¹ (K ⁱ¹ represents a substituent represented by the following general formulas (K-1) to (K-11)) and R ⁱ¹ (R ⁱ¹ represents a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, an alkyl halide group, or P ⁱ¹ -Sp ^i1- , and -CH _2- in the alkyl group is -CH = CH-, -C≡C-, -O-, -NH-, -COO- or -OCO- may be substituted, but -O- is not continuous)
In the above general formula (ii), Z ⁱⁱ¹ is preferably single-bonded, -CH = CH-, -C≡C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CH = CHCOO. -, -OCOCH = CH-, -CH ₂ -CH ₂ COO-, -OCOCH ₂ -CH _2- , -CH = C (CH ₃ ) COO-, -OCOC (CH ₃ ) = CH-, -CH _2- CH (CH ₃ ) COO-, -OCOCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-, or a linear or branched alkylene group having 1 to 40 carbon atoms, or in the alkylene group. One or two or more non-adjacent -CH _2- represents a group substituted with -O-, more preferably a single bond, -COO-, -OCO-, -CH = CHCOO-, -OCOCH = CH-, -CH ₂ -CH ₂ COO-, -OCOCH ₂ -CH _2- , -CH = C (CH ₃ ) COO-, -OCOC (CH ₃ ) = CH-, -CH ₂ -CH (CH ₃ ) COO-, -OCOCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-, or a linear or branched alkylene group having 1 to 40 carbon atoms, or one or adjacent to the alkylene group. No two or more -CH ₂ -s are single-bonded at -O-, a linear alkylene group with 2 to 15 carbon atoms, or one or two or more non-adjacent -CH _2s in the alkylene group. -Represents a group substituted with -O-, more preferably single bond, CH ₂ -CH ₂ COO-, -OCOCH ₂ -CH _2- , -CH = C (CH ₃ ) COO-, -OCOC ( CH ₃ ) = CH-, -CH ₂ -CH (CH ₃ ) COO-, -OCOCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-, or an alkylene group having 2 carbon atoms (ethylene group (ethylene group) -CH ₂ CH _2- )) or a group in which one of -CH _2- in the ethylene group is substituted with -O- (-CH ₂ O-, -OCH _2- ), or a group having 3 to 13 carbon atoms. Represents a linear alkylene group or a group in which one or two or more non-adjacent _—CH2 −s in the alkylene group are substituted with —O—.

A ⁱⁱ¹ preferably represents a divalent 6-membered ring aromatic group or a divalent 6-membered ring aliphatic group, but is a divalent, unsubstituted 6-membered ring aromatic group, or a divalent, unsubstituted 6 The membered ring aliphatic group or the hydrogen atom in these ring structures is not substituted or is substituted with an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and a halogen atom. A divalent unsubstituted 6-membered ring aromatic group, a group in which a hydrogen atom in the ring structure is substituted with a fluorine atom, or a divalent unsubstituted 6-membered ring aliphatic group is preferable. The above hydrogen atom may be substituted with a halogen atom, an alkyl group or an alkoxy group, preferably a 1,4-phenylene group, a 2,6-naphthalene group or a 1,4-cyclohexyl group, but at least one substituent. Is replaced by P ⁱ¹ -Sp ^i1- .

^mii1 preferably represents an integer of 2 to 5, and more preferably an integer of 2 to 4.

General formula (iii);

(In the above general formula (iii), ^Riii1 is an alkyl group having 1 to 15 carbon atoms, in which at least one -CH _2- is substituted with -O- or -S-. Also, at least one- (CH ₂ ) _2- may be substituted with -CH = CH- or -C≡C-, in which at least one hydrogen atom is substituted with a halogen atom. May,
A ⁱⁱⁱ¹ and A ⁱⁱⁱ⁴ are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenanthrene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, respectively. , 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidin-2,5-diyl, pyridine-2 , 5-Diyl, Fluoren-2,7-Diyl, Phenanthrene-2,7-Diyl, Anthracen-2,6-Diyl, Perhydrocyclopenta [a] Phenanthrene-3,17-Diyl, or 2,3,4 , 7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta [a] phenanthrene-3,17-diyl, at least one hydrogen in these rings. Atoms are fluorine atoms, chlorine atoms, alkyl groups with 1 to 12 carbon atoms, alkenyl groups with 2 to 12 carbon atoms, alkoxy groups with 1 to 11 carbon atoms, or alkenyloxy groups with 2 to 11 carbon atoms. In these groups, at least one hydrogen atom may be substituted with a fluorine atom or a chlorine atom.
Z ⁱⁱⁱ¹ is a single bond or an alkylene having 1 to 10 carbon atoms, in which at least one -CH _2- is -O-, -CO-, -COO-, -OCO-, or -OCOO. It may be substituted with −, and at least one − (CH _{2) 2} − may be substituted with −CH = CH— or −C≡C−, and in these groups, at least one hydrogen atom is a. May be substituted with a halogen atom,
^Siii1 is a single bond or an alkylene group having 1 to 10 carbon atoms, in which at least one -CH _2- is -O-, -CO-, -COO-, -OCO-, or. -OCOO- may be substituted, and at least one- (CH ₂ ) _2- may be substituted with -CH = CH- or -C≡C-, and in these groups, at least one hydrogen is. , May be replaced with a halogen atom,
^Kiii1 and ^Kiii2 are independently from hydrogen atom, halogen atom, alkyl group having 1 to 5 carbon atoms, or at least one hydrogen atom substituted with a halogen atom (for example, a fluorine atom). It is an alkyl group of 5 and
ⁿⁱⁱⁱ¹ is 0, 1, 2, 3, or 4,
^Riii2 is a group represented by the formula (iii-1) or the formula (iii-2).

In equations (iii-1) and (iii-2),
S ^{ii 2} and S ^{ii 3} are each independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the alkylene group, at least one -CH _2- is -O-, -NH-, -CO. -, -COO-, -OCO-, or -OCOO- may be substituted, and at least one- (CH ₂ ) _2- may be substituted with -CH = CH- or -C≡C-. In these groups, at least one hydrogen atom may be substituted with a halogen atom.
^Siii1 is = CH- or = N-,
X ^{iii 1} is -OH, -NH ₂ , -OR ³ , -N (R ³ ) ₂ , formula (X ^{ii 1} ), -COOH, -SH, -B (OH) ₂ , or -Si (R ³ ) ₃ . A group represented by, wherein R ³ is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and in the alkyl group, at least one -CH _2- is -O- or -CH. = CH-may be substituted, and in these groups, at least one hydrogen atom may be substituted with a halogen atom.
Equation ( ^Xiii1 ):

(Nii2 is an integer from 1 to 5.)
General formula (iv);

Since the compound represented by the general formula (iv) has a partial structure represented by ^{Ki 1} , it is oriented toward a substrate sandwiching the liquid crystal composition (liquid crystal layer) when used in a liquid crystal composition. The liquid crystal molecules can be held in a vertically oriented state. Since the partial structure represented by ^{Ki 1} has polarity, the compound represented by the general formula (iv) is adsorbed on the substrate sandwiching the liquid crystal composition (liquid crystal layer), and the compound is represented by ^{Ki 1} . Since it has a partial structure at the end of the compound, it is considered that the liquid crystal molecules are held in a vertically oriented state. Therefore, according to the liquid crystal composition using the polymerizable compound of the present embodiment, the liquid crystal molecules are oriented without providing the PI layer (the vertical orientation of the liquid crystal molecules is induced when no voltage is applied, and the liquid crystal molecules are oriented when the voltage is applied. (Achieves horizontal orientation) is possible. For this reason, liquid crystal compositions containing compound (iv) are preferably used to aid in the vertical orientation of liquid crystal molecules.

In addition, the present inventors have not only the orientation of the liquid crystal molecules but also the storage stability of the liquid crystal composition because the liquid crystal composition containing the compound (iv) in the present embodiment has a partial structure represented by ^Ki1 . We have found that stability can be ensured.

Further, the liquid crystal composition containing the compound (iv) represented by the general formula (iv) has a polymerizable group at a specific position as a substituent of ^Ai2 or ^Ai3 or as a substituent of ^Ki1 . Therefore, better orientation can be maintained.

From the above viewpoint, the compound (iv) in the liquid crystal composition of the present embodiment may have a partial structure represented by ^Ki1 at the end of the molecule, preferably at the end of the main chain of the molecule. The chemical structure to which the partial structure represented by ⁱ¹ is bound is not particularly limited as long as it does not impair the function of the liquid crystal composition.

Hereinafter, specific examples of the compound represented by the general formula (iv) will be described.

^Ki1 in the general formula (iv) is preferably a linear or branched alkyl group having 3 to 40 carbon atoms, a linear or branched alkyl halide having 3 to 40 carbon atoms, and 3 to 3 carbon atoms. Forty linear or branched alkyl cyanoated groups, where at least two or more secondary carbon atoms in ^{Ki1 are-(C = X i1 )} -and / or-(CH-CN)-. It is substituted with, and at least two or more secondary carbon atoms in Ki1 are preferably substituted ^{with-(C = X i1 )} -, and at least three or more secondary carbon atoms are-. It is preferable that it is substituted with (C = X ⁱ¹ )-, and at least four or more secondary carbon atoms are preferably substituted with-(C = X ⁱ¹ )-. X ⁱ¹ is preferably an oxygen atom from the viewpoint of improving the voltage retention rate (VHR). K ⁱ¹ preferably represents a linear or branched alkyl group having 3 to 30 carbon atoms, a linear or branched halogenated alkyl group, or a linear or branched cyanated alkyl group, and is the first in the alkyl group. Secondary carbon atoms should be so that oxygen atoms are not directly adjacent to each other- (C = CH ₂ )-,-(C = CHR ⁱ³ )-,-(C = CR ⁱ³ ₂ )-, -CH = CH-, -C≡ It may be substituted with C—, —O—, and more preferably, it represents a linear or branched alkyl group having 3 to 20 carbon atoms or a linear or branched cyanoated alkyl group, and is the first in the alkyl group. Secondary carbon atoms may be substituted with-(C = CH ₂ )-,-(C = CHR ⁱ³ )-,-(C = CR ⁱ³ ₂ )-, -O- so that oxygen atoms are not directly adjacent to each other. , More preferably, it represents a branched alkyl group or a branched cyanated alkyl group having 3 to 20 carbon atoms so that the secondary carbon atom in the alkyl group is not directly adjacent to the oxygen atom-(C = CH). ₂ ) It may be replaced with − or —O—. R ⁱ³ is preferably a linear or branched alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 7 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms, and the first of the alkyl groups. The secondary carbon atom may be substituted with -O-, -CH = CH- or -C≡C- so that the oxygen atom is not directly adjacent.

Further, it is preferable that the hydrogen atom in ^Ki1 is substituted with a polymerizable group, that is, ^Pi1 -Sp ^i1- . The presence of polar groups and polymerizable groups in ^Ki1 provides better orientation.

K ⁱ¹ preferably represents the general formula (K-24).

(In the formula, Y ⁱ¹ represents a linear or branched alkyl group having 3 to 20 carbon atoms, a halogenated alkyl group or a cyanated alkyl group, and at least two or more secondary carbons in these alkyl groups. The atom is substituted with-(C = X ⁱ¹ )-and / or-(CH-CN)-and the secondary carbon atom in the alkyl group is -CH = so that the oxygen atom is not directly adjacent. It may be substituted with CH-, -C≡C-, -O-, -NH-, -COO- or -OCO-, and the hydrogen atom in these alkyl groups is substituted with ^Pi1 -Sp ^i1- . X ⁱ¹ represents an oxygen atom, a sulfur atom, NH or NR ⁱ³ .
S ⁱ¹ and S ⁱ³ independently represent an alkylene group or a single bond having 1 to 6 carbon atoms, and -CH _2- in the alkylene group is -CH = CH-,-so that oxygen atoms are not directly adjacent to each other. C≡C-,-(C = CH ₂ )-,-(C = CHR ⁱ³ )-,-(C = CR ⁱ³ ₂ )-, -O-, -NH-,-(C = O)-,- It may be replaced with COO- or -OCO-,
S ⁱ² represents a carbon atom, a nitrogen atom or a silicon atom, and represents
R ⁱ² represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group or a cyanated alkyl group, and the secondary carbon atom in these groups is not directly adjacent to an oxygen atom. As in -O-, -CH = CH-, -C≡C-, -C (= ^Xi1 )-or -CH (-CN)-may be substituted.
P ⁱ¹ represents a polymerizable group and represents
Sp ⁱ¹ represents a spacer group or a single bond.
n ⁱ¹ represents an integer of 1 to 3, n ⁱ² and n ⁱ³ each independently represent an integer of 0 to 2, but when S ⁱ² represents a carbon atom or a silicon atom, n ⁱ¹ + n ⁱ² + n ⁱ³ is 3 When S ⁱ² represents a nitrogen atom, n ⁱ¹ + n ⁱ² + n ⁱ³ is 2. R ⁱ³ has the same meaning as R ⁱ³ in the general formula (i), and there are a plurality of R ⁱ² , X ⁱ¹ , Y ⁱ¹ , S ⁱ¹ , S ^{i 3} , ^{Pi 1} and Sp ⁱ 1 in the general formula (K-1). If so, they may be the same or different. )
S ⁱ¹ and S ⁱ³ in the general formula (K-1) are preferably a linear or branched alkylene group or a single bond having 1 to 6 carbon atoms, and -CH _2- in the alkylene group is an oxygen atom. May be replaced with -CH = CH-,-(C = CH ₂ )-, -O-,-(C = O)-, -COO- or -OCO- so that they are not directly adjacent to each other, more preferably. , Single bond, linear alkylene group having 1 to 6 carbon atoms, or -CH _2- in the alkylene group is preferably a group substituted with -O- so that oxygen atoms are not directly adjacent to each other. .. Specifically, S ⁱ¹ and S ⁱ³ are-(CH _{2) n-, -O- (CH 2 )} n-,-(CH ₂ ) n-O-,-(CH ₂ ) n-O- (CH). ₂ ) It is preferable to represent m-, -COO- (CH ₂ ) n-, -OCO- (CH ₂ ) n- (n and m represent integers of 1 to 6).
S ⁱ² is preferably a carbon atom. R ⁱ² preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms, in which -CH _2- is -O-, -C (= X ⁱ¹ )-or-. It may be substituted with CH (-CN)-(whereever -O- is not continuous) and preferably represents a hydrogen atom or a linear or branched alkyl group having 1 to 7 carbon atoms, said alkyl group. -CH ₂ -in the medium may be replaced with -O-, -C (= X ⁱ¹ )-or -CH (-CN)-(however, -O- is not continuous), and more preferably hydrogen. A straight chain alkyl group having 1 to 3 atoms and 1 to 3 carbon atoms is preferable.

Y ⁱ¹ is an alkyl group having 3 to 20 carbon atoms, a linear or branched alkyl halide group having 3 to 20 carbon atoms, and a linear or branched alkyl halide group having 3 to 20 carbon atoms. So, at least two or more secondary carbon atoms in Y ⁱ¹ are substituted with-(C = X ⁱ¹ )-and / or-(CH-CN)-and at least two or more in Y ⁱ¹ . The secondary carbon atom is preferably substituted with-(C = X ⁱ¹ )-. X ⁱ¹ is preferably an oxygen atom from the viewpoint of improving the voltage retention rate (VHR). Y ⁱ¹ preferably represents a linear or branched alkyl group having 3 to 10 carbon atoms, a halogenated alkyl group, or a cyanated alkyl group, and the secondary carbon atom in the alkyl group is directly adjacent to an oxygen atom. Replaced with-(C = CH ₂ )-,-(C = CHR ⁱ³ )-,-(C = CR ⁱ³ ₂ )-, -CH = CH-, -C≡C-, -O- so as not to It is also preferable, and more preferably, it represents a linear or branched alkyl group or cyanated alkyl group having 3 to 7 carbon atoms so that the secondary carbon atom in the alkyl group is not directly adjacent to the oxygen atom. It may be substituted with C = CH ₂ )-,-(C = CHR ⁱ³ )-,-(C = CR ⁱ³ ₂ )-, -O-, and more preferably a linear chain having 3 to 7 carbon atoms or Representing a branched alkyl group, the secondary carbon atom in the alkyl group may be substituted with —O— so that the oxygen atom is not directly adjacent. Further, the hydrogen atom in the alkyl group may be substituted with ^Pi1 -Sp ^i1- .

It is preferable that Y ⁱ¹ represents a group selected from the general formula (Y-1) from the viewpoint of improving the orientation of the liquid crystal display.

(In the formula, ^WiY1 represents a single bond or an oxygen atom, a broken line represents a single bond or a double bond, and ^RiY1 is a straight line having a hydrogen atom and 1 to 20 carbon atoms when the broken line represents a single bond. Or a branched alkyl group or P ⁱ¹ -Sp ^i1- , and the secondary carbon atom in the alkyl group is -O-, -CH = CH-, -C≡C- or so that the oxygen atom is not directly adjacent. It may be substituted with -CO-, and when the broken line represents a double bond, it represents = CH ₂ , = CHR ^iY4 , or = CR ^iY4 ₂ , where R ^iY4 is a straight line with hydrogen atoms and 1 to 20 carbon atoms. Alternatively, it represents a branched alkyl group, and the secondary carbon atom in the alkyl group may be substituted with -O-, -CH = CH- or -C≡C- so that the oxygen atom is not directly adjacent to each other. ^iY3 has the same meaning as R ^iY1 when the broken line represents a single bond, and R ^iY2 is a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group, and a cyanated alkyl group. Representing, the secondary carbon atoms in these alkyl groups are -CH = CH-, -C≡C-, -O-, -NH-, -COO-, -OCO-, so that oxygen atoms are not directly adjacent to each other. It may be replaced with −C (= O) − or −CH ₂ (−CN) −, where R ^iY2 represents Pi1 ^{−Sp i1 −} and n ^iY1 is 0 when the broken line represents a double bond. Yes, the broken line is ¹ when it represents a single bond, ^niY2 represents an integer from 0 to 5, Pi1 represents a polymerizable group, Sp ⁱ¹ represents a spacer group or a single bond, and R ^iY1 , R ^iY3 , When a plurality of R ^iY4 , Pi ¹ and Sp ^{i 1} exist, they may be the same or different, and they are combined with S ^{i 3} by *.)
When the broken line represents a single bond, R ^iY1 is preferably a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, and is preferably a hydrogen atom or an alkyl group. An alkyl group having 1 to 3 carbon atoms is preferable, and the secondary carbon atom in the alkyl group is substituted with -O-, -CH = CH- or -C≡C- so that the oxygen atom is not directly adjacent to the alkyl group. May be good. Specifically, it preferably represents a hydrogen atom, and from the viewpoint of improving heat resistance, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, -CO-CH ₃ , and -CH. It is preferable to represent ₂ -O-CH ₃ . Further, R ^iY1 is preferably represented as ^Pi1 -Sp ^i1- from the viewpoint of improving heat resistance. When R ^iY1 represents P ⁱ¹ -Sp ^i1- , the decomposition product generated by the decomposition of the compound represented by the general formula (i) by heat is polymerized, so that the increase of impurities can be prevented. , It is considered that the adverse effect on the liquid crystal composition is reduced. P ⁱ¹ represents a polymerizable group, and preferably represents an acryloyl group, a methacryloyl group, or a substituent selected from the group represented by the general formulas (P-1) to (P-15) described later. Sp ⁱ¹ preferably represents a linear alkylene group or a single bond having 1 to 18 carbon atoms, more preferably represents a linear alkylene group or a single bond having 2 to 15 carbon atoms, and more preferably represents a carbon atom number. Represents 2-8 linear alkylene groups or single bonds.

When the broken line represents a double bond, it preferably represents = CH ₂ , = CHR ^iY4 , or = CR ^iY4 ₂ and = CH ₂ . R ^iY4 is preferably a linear or branched alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 7 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms, and the first of the alkyl groups. The secondary carbon atom may be substituted with -O-, -CH = CH- or -C≡C- so that the oxygen atom is not directly adjacent.

The preferred group of R ^iY3 is the same as the preferred group of R ^iY1 when the dashed line represents a single bond. n ^iY1 is preferably 0.

Preferred combinations of R ^iY1 and R ^iY3 include hydrogen atoms, alkyl groups having 1 to 3 carbon atoms, alkoxy groups having 1 to 3 carbon atoms, and -CH ₂ -O-CH ₃ and the like. When either R ^iY1 or R ^iY3 represents ^Pi1 -Sp ^i1- or -CO-CH ₃ , the other preferably represents a hydrogen atom. n ^iY2 is preferably an integer of 0 to 3, more preferably 0, 1 or 2, and more preferably 0 or 1.

R ^iY2 is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group or a cyanated alkyl group, and preferably an alkyl group having 1 to 7 carbon atoms, a halogenated alkyl group or a cyanated alkyl group. , Alkyl groups having 1 to 3 carbon atoms are preferable. Further, it is preferable that the secondary carbon atom in the alkyl group is substituted with -O-,-(C = ^Xi2 )-or-( _CH2 -CN)-so that the oxygen atom is not directly adjacent to each other. .. Oxygen atom is preferable for X ⁱ² from the viewpoint of improving VHR. Further, R ^iY2 preferably represents P ⁱ¹ -Sp ^i1- . When R ^iY2 represents P ⁱ¹ -Sp ^i1- , the decomposition product generated by the decomposition of the compound represented by the general formula (i) by heat is polymerized, so that the increase of impurities can be prevented. , It is considered that the adverse effect on the liquid crystal composition is reduced.

More specifically, the general formula (Y-1) is a formula (Y-1-1), (Y-1-2), (Y-1-3a), (Y-1-3b), (Y). -1-4) is preferable.

(In the formula, ^niY11 represents 0 or 1, ^RiY21 represents an alkyl group having 1 to 10 carbon atoms, an alkyl halide group, and an alkyl cyanated group, and the secondary carbon atom in these alkyl groups is -CH = CH-, -C≡C-, -O-, -NH-, -COO-, -OCO-,-(C = O)-or-( _CH2 -CN) so that oxygen atoms are not directly adjacent to each other. )-May be substituted, and R ^iY21 represents Pi1 ^{−Sp i1-} , and R ^iY31 and R ^iY32 are independently hydrogen atoms and linear or branched alkyl groups having 1 to 10 carbon atoms, respectively. The secondary carbon atom in the alkyl group may be substituted with -O-, -CH = CH-, -C≡C- or -CO- so that the oxygen atom is not directly adjacent to the alkyl group. R ^iY31 and R ^iY32 represent P ⁱ¹ -Sp ^i1- ).
The R ^iY21 is preferably an alkyl group having 1 to 7 carbon atoms, a halogenated alkyl group or a cyanated alkyl group, and preferably an alkyl group having 1 to 3 carbon atoms. Further, R ^iY21 preferably represents P ⁱ¹ -Sp ^i1- . R ^iY31 and R ^iY32 are preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, preferably a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, and 1 to 1 carbon atom. It is preferable to represent 3 alkoxy groups, -CO-CH ₃ , and -CH ₂ -O-CH ₃ . Further, it is preferable that at least one of R ^iY31 and R ^iY32 represents ^Pi1 -Sp ^i1- .

From the viewpoint of improving the compatibility with the liquid crystal compound, it is preferable to have the structure of the formula (Y-1-1). As the formula (Y-1-1), the formulas (Y-1-1a) to (Y-1-1h) are preferable.

(In the formula, ^niY11 represents 0 or 1.)
From the viewpoint of improving compatibility with the liquid crystal compound and heat resistance, it is preferable to have the structure of the formula (Y-1-2). As the formula (Y-1-2), the formulas (Y-1-2a) to (Y-1-2f) are preferable.

(In the formula, ^niY11 represents 0 or 1.) From the viewpoint of improving heat resistance, it is preferable to have the structures of the formula (Y-1-3a) and the formula (Y-1-3b). The formula (Y-1-3a) is preferably the formula (Y-1-3aa), and the formula (Y-1-3b) is preferably the formula (Y-1-3ba).

(In the formula, ^niY11 represents 0 or 1.)
From the viewpoint of improving the orientation and voltage retention of the liquid crystal composition, it is preferable to have the structure of the formula (Y-1-4). As the formula (Y-1-4), the formulas (Y-1-4a) to (Y-1-4f) are preferable. In particular, the structures (Y-1-4a) to (Y-1-4c) are preferable because they have a good balance between the compatibility with the liquid crystal compound and the orientation of the liquid crystal composition.

(In the formula, ^niY11 represents 0 or 1.)
Further, it is preferable that Y ⁱ¹ represents a group selected from the general formula (Y-2).

(In the formula, ^WiiY1 , R ^iY3 and R ^iY2 have the same meanings as ^WiiY1 , R ^iY3 and R ^iY2 in the general formula (Y-1).)
The general formula (Y-2) preferably represents the general formula (Y-2-1).

(In the formula, n ^iY11 , R ^iY21 and R ⁱ³¹ have the same meanings as n ^iY11 , R ^iY21 and R ⁱ³¹ in the general formula (Y-1-1).)
Further, it is preferable that Y ⁱ¹ represents a group selected from the general formula (Y-3) from the viewpoint of improving heat resistance.

(In the formula, R ^iY1 , R ^iY2 , R ^iY3 , ^niY1 and ^niY1 have the same meanings as R ^iY1 , R ^iY2 , R ^iY3 , n ^iY1 and n ^iY1 in the general formula (Y-1), respectively.)
The general formula (Y-3) preferably represents the general formula (Y-3-1) to the general formula (Y-3-4).

(In the formula, R ^iY21 , R ^iY31 , R ^iY32 and n ^iY11 have the same meanings as R ^iY21 , R ^iY31 , R ^iY32 and n ^iY11 in the general formula (Y-1-1), respectively.)
More specifically, the general formula (Y-3-1) is preferably the general formula (Y-3-11).

(In the formula, R ^iY21 has the same meaning as R ^iY21 in the general formula (Y-3-1).)
Further, it is preferable that Y ⁱ¹ represents a group selected from the general formula (Y-4) from the viewpoint of improving heat resistance.

(In the formula, R ^iY1 , R ^iY2 , R ^iY3 , ^niY1 and ^niY1 have the same meanings as R ^iY1 , R ^iY2 , R ^iY3 , n ^iY1 and n ^iY1 in the general formula (Y-1), respectively.)
The general formula (Y-4) preferably represents the general formula (Y-4-1) to the general formula (Y-4-3b).

(In the formula, R ^iY21 , R ^iY31 , R ^iY32 and n ^iY11 have the same meanings as R ^iY21 , R ^iY31 , R ^iY32 and n ^iY11 in the general formula (Y-1-1), respectively.)
More specifically, the general formula (Y-4-1) is preferably the general formula (Y-4-11).

(In the formula, R ^iY21 has the same meaning as R ^iY21 in the general formula (Y-4-1).)
P ⁱ¹ preferably represents a substituent selected from the group represented by the following formulas (P-1) to (P-15). From the viewpoint of ease of handling and reactivity, any of the substituents of the formulas (P-1) to (P-3), (P-14) and (P-15) is preferable, and the formula (P-1) is preferable. , (P-2) are more preferable.

(In the formula, the black dot at the right end represents the bond.)

Sp ⁱ¹ preferably represents a linear alkylene group or a single bond having 1 to 18 carbon atoms, more preferably represents a linear alkylene group or a single bond having 2 to 15 carbon atoms, and more preferably a carbon atom. Represents a linear alkylene group or single bond of number 2-8.

n ⁱ¹ preferably represents 1 or 2 from the viewpoint of improving the orientation of the liquid crystal and the solubility in the liquid crystal compound. n ⁱ² preferably represents 0 or 1, and more preferably 1 from the viewpoint of improving the orientation. n ⁱ³ preferably represents 0 or 1.

The general formula (K-24) preferably represents a group selected from the general formula (K-24A) or (K-24B).

(In the formula, S ⁱ¹ , S ⁱ² , S ⁱ³ , Y ⁱ¹ , P ^{i 1} and S p i 1 are S ⁱ 1, S ⁱ 2, S i ³ , Y i ¹ , P ^{i 1} and S p i ¹ in the general formula (K-1). They have the same meaning, n ^iA1 represents an integer of 1 to 3, n ^iA3 represents an integer of 0 to 2, ^niB1 represents an integer of 1 to 2, and n ^iB3 represents 0 or 1, but S. If ⁱ² represents a carbon atom or a silicon atom, n ^iA1 + n ^iA3 is 3, n ^iB1 + n ^iB3 is 2, and if S ⁱ² represents a nitrogen atom, n ^iA1 + n ^iA3 is 2, and n ^iB1 is. 1, ^niB3 represents 0.)

^Ki1 in the formula (i) is an important structure for vertically orienting the liquid crystal composition, and by adjoining the polar group and the polymerizing group, better orientation can be obtained, and the liquid crystal composition can also be oriented. Shows good solubility in. Therefore, when the orientation of the liquid crystal is important, the general formula (K-24B) is preferable. On the other hand, when the solubility in the liquid crystal compound is important, the general formula (K-24A) is preferable. Preferred examples of the general formulas (K-24A) to (K-24B) are the following formulas (K-24A-1) to (K-24A-4) and formulas (K-24B-1) to (K-24B). -6) can be mentioned, but the formulas (K-24A-1) to (K-24A-3) are preferable from the viewpoint of solubility in the liquid crystal composition, and the formula (K-24B) is preferable from the viewpoint of orientation. -2) to (K-24B-4) are preferable, and formulas (K-24A-1), (K-24B-2) and (K-24B-4) are particularly preferable.

(In the formula, S ⁱ¹ , Y ^{i 1} and P ^{i 1} independently represent the same meanings as S ^{i 1} , Y ^{i 1} and P ⁱ 1 in the general formula (K-24).)
Further, the general formula (K-24) is a general formula (K-24-1), (K-24-2), (K-24-3a), (K-24-3b), (K-24-3b). 4a), (K-24-4b) (K-24-Y2), (K-24-Y3) and (K-24-Y4) are preferably represented.

(In the formula, n ^iY11 , R ^iY21 , R ^iY31 and R ^iY32 are independently the same as n ^iY11 , R ^iY21 , R ^iY31 and R ^iY32 in the general formulas (Y-1-1) to (Y-4), respectively. Sp ⁱ¹ and Pi ¹ have the same meaning as Sp ^{i 1} and Pi ¹ in the general formula (i), respectively, and R ^iK1 represents an alkylene group or a single bond having 1 to 6 carbon atoms. -CH _2- in the group may be substituted with -CH = CH-, -C≡C- or -O- so that oxygen atoms are not directly adjacent to each other, and ^{niK1 and niK2 are} independently 0. Or represents 1.)
R ^iK1 is preferably a linear alkylene group having 1 to 6 carbon atoms, and preferably a linear alkylene group having 1 to 3 carbon atoms. Preferred groups of R ^iY21 , R ^iY31 , R ^iY32 , Sp ⁱ¹ and Pi ¹ are general formulas (Y-1-1) to (Y-1-4), (Y-2) to (Y-4), and more. It is the same as R ^iY21 , R ^iY31 , R ^iY32 , Sp ⁱ¹ and Pi ¹ in the general formula (i).

Further, K ⁱ¹ preferably represents the general formulas (K-25) to (K-28).

(In the formula, S ⁱ¹ , P ^{i 1} and S p ^{i 1} have the same meanings as S ^{i 1} , P i 1 and S p i 1 in the general formula ( ^{K-24), respectively, and RK21 is} a linear or linear chain having 1 to 10 carbon atoms. Represents a branched alkyl group, halogenated alkyl group or cyanated alkyl group, and at least one secondary carbon atom in these alkyl groups is -CH = CH-, -C so that oxygen atoms are not directly adjacent to each other. It may be replaced with ≡C-, -O-, or -NH-, and ⁿⁱ⁴ and ^niK21 independently represent 0 or 1, respectively.)
^RK21 preferably represents a linear or branched alkyl group having 1 to 5 carbon atoms, a halogenated alkyl group or a cyanated alkyl group, and a linear alkyl group or a cyanated alkyl group having 1 to 3 carbon atoms. It is more preferable to represent it. Further, it is preferable that at least one or more secondary carbon atoms in these alkyl groups are substituted with —O— so that oxygen atoms are not directly adjacent to each other. Specifically, the ^RK21 is preferably an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, and a cyanated alkyl group having 1 to 3 carbon atoms.

The general formula (K-25) preferably represents the following general formulas (K-25-1) to (K-25-3).

(In the formula, S ⁱ¹ , P ⁱ 1, S p i 1, n i 4 and ^{ni K21 have} the same meanings as S ^{i 1} , P ^{i 1} , Sp ^{i 1} , n i 4 and n ^{i K21 in} the general formula (K-25), respectively, and R ^K211 represents a linear or branched alkyl group having 1 to 3 carbon atoms, a halogenated alkyl group, or a cyanated alkyl group.)
The general formula (K-26) preferably represents the following general formulas (K-26-1) and (K-26-2).

(In the formula, ^{Si1 has the same meaning as Si1 in the general formula (K-26), and RK211 is a} linear or branched alkyl group having 1 to 3 carbon atoms, an alkyl halide group or an alkyl cyanated. Represents a group.)
The general formula (K-27) preferably represents the following general formula (K-27-1).

(In the formula, S ⁱ¹ , P ^{i 1} , Sp ⁱ 1 and n i 4 have the same meanings as S ^{i 1} , P ^{i 1} , Sp ^{i 1} and n i ^K21 in the general formula (K-27), respectively, and ^{RK2 11 has} 1 carbon atom. Represents a linear or branched alkyl group of 3 to 3, an alkyl halide group or an alkyl cyanated group).
The general formula (K-28) preferably represents the following general formula (K-28-1).

(In the formula, S ⁱ¹ , P ^{i 1} , Sp ⁱ 1 and n i 4 have the same meanings as S ^{i 1} , P ^{i 1} , Sp ^{i 1} and n i ^K21 in the general formula (K-28), respectively, and ^{RK2 11 has} 1 carbon atom. Represents a linear or branched alkyl group of 3 to 3, an alkyl halide group or an alkyl cyanated group).
The preferred groups of S ⁱ¹ , P i 1 and S p ^{i 1} are the same as those of S ^{i 1} , P i 1 and S p ^{i 1} in the general formula (K-24).

In formula (i), Z ⁱ¹ and Z ⁱ¹ are preferably single-bonded, -CH = CH-, -C≡C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CH =. CHCOO-, -OCOCCH = CH-, -CH = C (CH ₃ ) COO-, -OCOC (CH ₃ ) = CH-, -CH ₂ -CH (CH ₃ ) COO-, -OCOCCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-, a linear or branched alkylene group having 1 to 40 carbon atoms, or one or two or more non-adjacent -CH _2- in the alkylene group is -O. Represents a group substituted with-, more preferably a single bond, -COO-, -OCO-, -CH = CHCOO-, -OCOCH = CH-, -CH = C (CH ₃ ) COO-, -OCOC ( CH ₃ ) = CH-, -CH ₂ -CH (CH ₃ ) COO-, -OCOCH (CH ₃ ) -CH _2- , -OCH ₂ CH ₂ O-, linear or branched with 1 to 10 carbon atoms. Represents an alkylene group in the form of an alkylene group, or a group in which one or two or more -CH _2- but not adjacent to each other are substituted with -O-, more preferably a single bond and having 2 to 15 carbon atoms. Represents a linear alkylene group, or a group in which one or two or more non-adjacent _—CH2 −s in the alkylene group are substituted with —O—, more preferably a single bond, —COO−, −. OCO-, -OCOO-, -OOCO-, -OCH ₂ CH ₂ O-, or an alkylene group having 2 carbon atoms (ethylene group (-CH ₂ CH _2- )) or -CH _2-1 in an ethylene group. A group in which an element is substituted with -O- (-CH ₂ O-, -OCH _2- ), or a group in which one of -CH _2- in an ethylene group is substituted with -COO-, -OCO- (-). CH-CHCOO-, -OCOCH-CH-).

R ⁱ¹ preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms, or a halogenated alkyl group, so that the secondary carbon atom in the alkyl group is not directly adjacent to the oxygen atom. O—, which is often substituted, more preferably represents a linear or branched alkyl group having 3 to 18 carbon atoms so that the secondary carbon atom in the alkyl group is not directly adjacent to the oxygen atom. May be replaced with —O—. From the viewpoint of improving the orientation of the liquid crystal compound, the number ^{of carbon atoms of Ri1} is preferably 3 or more, preferably 4 or more, and preferably 5 or more.

A ⁱ¹ is a divalent 6-membered ring aromatic group, a divalent 6-membered ring heteroaromatic group, a 2-valent 6-membered ring aliphatic group, or a divalent 6-membered ring complex aliphatic group, or divalent. A 5-membered ring aromatic group, a divalent 5-membered ring heteroaromatic group, a divalent 5-membered ring aliphatic group, or a divalent 5-membered ring heteroaromatic group is preferable, and specifically, 1,4 -Phenylene group, 1,4-cyclohexylene group, anthracene-2,6-diyl group, phenanthren-2,7-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene- 2,6-diyl group, cyclopentane-1,3-diyl group, indan-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group and 1,3-dioxane- It is preferable to represent a ring structure selected from 2,5-diyl groups, and it is preferable that the ring structure is unsubstituted or substituted with ^Li1 . ^Li1 is an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, and the like. It preferably represents a cyano group or a nitro group. A ⁱ¹ preferably represents a divalent 6-membered ring aromatic group or a divalent 6-membered ring aliphatic group, but is a divalent, unsubstituted 6-membered ring aromatic group, and is a divalent, unsubstituted 6-membered group. The ring aliphatic group, or a group in which the hydrogen atom in these ring structures is substituted with an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom is preferable, and the divalent group is used. The unsubstituted 6-membered ring aromatic group, the group in which the hydrogen atom in the ring structure is substituted with a fluorine atom, or the divalent unsubstituted 6-membered ring aliphatic group is preferable, and the hydrogen atom on the substituent is A 1,4-phenylene group, a 2,6-naphthalene group or a 1,4-cyclohexyl group which may be substituted with a halogen atom, an alkyl group or an alkoxy group is more preferable.

A ⁱ² and A ⁱ³ are independently divalent 6-membered ring aromatic groups, divalent 6-membered ring heteroaromatic groups, 2-valent 6-membered ring aliphatic groups, or divalent 6-membered ring complex. An aliphatic group, a divalent 5-membered ring aromatic group, a divalent 5-membered ring heteroaromatic group, a divalent 5-membered ring aliphatic group, or a divalent 5-membered ring heteroaromatic group is preferable. Specifically, 1,4-phenylene group, 1,4-cyclohexylene group, anthracene-2,6-diyl group, phenanthren-2,7-diyl group, pyridine-2,5-diyl group, pyrimidin-2, 5-Diyl group, naphthalene-2,6-diyl group, cyclopentane-1,3-diyl group, indan-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group And 1,3-dioxane-2,5-diyl groups are preferably represented, the ring structure being unsubstituted or substituted with ^Li1 , ^Pi1 -Sp ^i1- or K ⁱ¹ . It is preferable that it is. Further, it is also preferable that ^Ai3 represents a ring structure selected from a 1,3-phenylene group, a 1,3-cyclohexylene group and a naphthalene 2,5-diyl group.

The preferred groups of ^Lii1 are the same as ^Lii1 in ^Ai1 . A ⁱ² and A ⁱ³ preferably represent a divalent 6-membered ring aromatic group or a divalent 6-membered ring aliphatic group, but are divalent, unsubstituted, 6-membered ring aromatic groups, and 2-valent, unsubstituted. 6-membered ring aliphatic group, or a group in which the hydrogen atom in these ring structures is substituted with an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogen atom or P-Sp-. Is preferable, a divalent unsubstituted 6-membered ring aromatic group, a group in which a hydrogen atom in the ring structure is substituted with a fluorine atom, or a divalent unsubstituted 6-membered ring aliphatic group is preferable. , The hydrogen atom on the substituent may be substituted with a halogen atom, an alkyl group or an alkoxy group, a P-Sp-, a 1,4-phenylene group, a 2,6-naphthalene group or a 1,4-cyclohexyl group. preferable. It is also preferable that A ⁱ³ is replaced with K ⁱ¹ .

Here, the general formula (i) has at least one or more ^Pi1 -Sp ^i1- as a substituent of A ⁱ² or A ⁱ³ or as a substituent of Ki ¹ , but further improves reliability. From the viewpoint, the number of polymerizable groups in the general formula (i) is preferably 2 or more, and preferably 3 or more. When reliability is important, polyfunctionalization can be easily achieved by introducing a polymerization group into the ^Ai2 or ^Ai3 part, and a strong polymer can be constructed. The position where P ⁱ¹ -Sp i1- is replaced in A ⁱ² or A ^{i 3} is preferably in the vicinity of K ^{i 1 ,} and it is more preferable that A ^{i 3} is replaced with P ⁱ¹ -Sp ^i1- .

^mi1 preferably represents an integer of 0 to 3, and more preferably represents an integer of 0 to 1.

The compound represented by the general formula (iv) is preferably a compound represented by the following general formula (iv-1).

(In the formula, R ⁱ¹ , A ⁱ¹ , A ⁱ² , Z ⁱ¹ , Z ⁱ² , ^{mi 1} , ^{Pi 1} and Sp ^{i 1} are independently R ^{i 1} , A ⁱ 1, A ⁱ 2, Z ⁱ 1 in the general formula (iv). , Z ⁱ² , ^{mi 1, Pi 1 and Sp i 1, and Y i 1 independently represent the same meaning as Y i 1 in the general formula (K-24), R iK1 , n iK 1 , n i K2} . Independently represent the same meanings as R ^iK1 , ^niK1 , and ^niK2 in the general formula (K-24-1), ^Li11 represents an alkyl group having 1 to 3 carbon atoms, and ^mi3 represents 0 to 0. Represents an integer of 3, ^mi4 represents an integer of 0 to 3, while ^mi3 + ^mi4 represents 0 to 4).
The compounds represented by the general formula (iv-1) are the following general formulas (iv-1-1), (iv-1-2), (iv-1-3a), (iv-1-3b), and the like. It is preferably (iv-1-4), (iv-1-Y2), (iv-1-Y3) and (iv-1-Y4).

(In the formula, R ⁱ¹ , A ⁱ¹ , A ⁱ² , Z ⁱ¹ , Z ⁱ² , ^{mi 1} , ^{Pi 1} and Sp ^{i 1} are independently R ^{i 1} , A ⁱ 1, A ⁱ 2, Z ⁱ 1 in the general formula (iv). , Z ⁱ² , ^{mi 1, Pi 1 and Sp i 1, and R iK1, R iY21, R i3Y1, R i3Y2 , n iK1 , n iK2 , n iY11} are independent general formulas (K-24-). 1) It has the same meaning as R ^iK1 , R ^iY21 , R ⁱ³¹ , R ⁱ³² , ^niK1 , n ^iK2 , and n ^iY11 in (K-24-3), and ^{Li i11} is an alkyl group having 1 to 3 carbon atoms. , ^Mi 3 represents an ^integer of 0 to 3, mi 4 represents an integer of 0 to 3, and mi ³ + ^mi 4 represents 0 to 4).
In addition, the preferable group of each code | symbol in the general formula (iv-1) and the general formula (iv-1-1), (iv-1-2), (iv-1-3) is the above-mentioned general formula (i). , The same as the preferred groups in the general formula (K-1) and the general formulas (K-1-1) to (K-1-3).

Further, the compound represented by the general formula (iv) is preferably a compound represented by the following general formulas (iv-2) to (iv-5).

(In the formula, R ⁱ¹ , A ⁱ¹ , A ⁱ² , Z ⁱ¹ , Z ⁱ² , ^{mi 1} , ^{Pi 1} and Sp ^{i 1} are independently R ^{i 1} , A ⁱ 1, A ⁱ 2, Z ⁱ 1 in the general formula (iv). , Z ⁱ² , mi 1, Pi ¹ and Sp ^{i 1} , and n ⁱ⁴ , n ^iK21 , ^RK21 are independently the same as n ⁱ⁴ , n ^iK21 , ^RK21 in the general formula ( ^K -24). Representing a meaning, ^Ri22 represents an alkylene group or a single bond having 1 to 6 carbon atoms, and -CH _2- in the alkylene group is -CH = CH-, -C≡C so that oxygen atoms are not directly adjacent to each other. It may be substituted with − or ^—O— , Li 11 represents an alkyl group having 1 to 3 carbon atoms, ^{ni 22} represents 0 or 1, mi 23 represents an ^integer of 0 to 3, and mi 24 represents an ^integer of 0 to 3. It represents an integer from 0 to 3, but ^mi23 + ^mi24 represents 0 to 4.)
R ⁱ²² is preferably a linear alkylene group having 1 to 6 carbon atoms, and preferably a linear alkylene group having 1 to 3 carbon atoms. The preferred groups of R ^iY21 , R ^iY31 , R ^iY32 , Sp ⁱ¹ and P ⁱ¹ are the general formulas (Y-1-1) to (Y-1-3), and the R ^iY21 and R ^iY31 in the general formula (i). , R ^iY32 , Sp ⁱ¹ , and Pi ¹ . The preferred group of each reference numeral in the general formula (iv-2) is the same as the preferred group in the general formula (iv) and the general formula (K-24).

The general formula (iv) preferably represents the following general formulas (R-1) to (R-6).

(In the formula, R ⁱ¹ , K ^{i 1} and ^{Li 1} have the same meanings as R ^{i 1} , K ^{i 1} and ^{Li 1} in the general formula (iv), respectively.)
More specific examples of the general formula (iv) are represented by the following formulas (R-1-1) to (R-6-7), but are not limited thereto.

(In the formula, R ⁱ¹ , P ^{i 1} , S ⁱ 1 and Y ^{i 1} have the same meanings as R ^{i 1} , P ^{i 1} , S ^{i 1} and Y i 1 in the general formula (iv) and the general formula (K-1), respectively. show.)
The lower limit of the content of the spontaneously oriented monomer in the liquid crystal composition of the present invention is preferably 0.02% by mass, preferably 0.03% by mass, preferably 0.04% by mass, and preferably 0.05% by mass. 0.06% by mass is preferable, 0.07% by mass is preferable, 0.08% by mass is preferable, 0.09% by mass is preferable, 0.1% by mass is preferable, 0.12% by mass is preferable, and 0. 15% by mass is preferable, 0.17% by mass is preferable, 0.2% by mass is preferable, 0.22% by mass is preferable, 0.25% by mass is preferable, 0.27% by mass is preferable, and 0.3% by mass is preferable. % Is preferable, 0.32% by mass is preferable, 0.35% by mass is preferable, 0.37% by mass is preferable, 0.4% by mass is preferable, 0.42% by mass is preferable, and 0.45% by mass is preferable. It is preferably 0.5% by mass, preferably 0.55% by mass. 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 2.5% by mass, preferably 2.3% by mass, and preferably 2.1% by mass. 2% by mass is preferable, 1.8% by mass is preferable, 1.6% 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. Preferably, 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. 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.

Specifically, the following compounds are mentioned as preferable spontaneous orientation monomers.

The liquid crystal composition according to the present invention is represented by the general formulas (N-1), (N-2) and (N-3) in addition to the compound represented by the general formula (I) and the spontaneously oriented monomer. It is preferable to contain one or more compounds selected from the compounds. These compounds are dielectrically negative compounds (the sign of Δε is negative and its absolute value is larger than 2).

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

(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 with -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-.
^{AN11, AN12, AN21, AN22, AN31 and AN32 are independently ( a )} 1,4-cyclohexylene groups (one -CH _2- or adjacent to each other present in this group). Two or more -CH _2- that are not used 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 = present 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 independently single-bonded, -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 an oxygen atom and represents
Although n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, 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 ^{AN11 to AN32 and Z N11 to Z N32 , they} may be the same or different. )
The compounds represented by the general formulas (N-1), (N-2) and (N-3) are preferably compounds having a negative Δε and an absolute value larger than 3.

In the general formulas (N-1), (N-2) and (N-3), ^RN11 , ^RN12 , ^RN21 , ^RN22 , ^RN31 and ^RN32 are independent of each other and have 1 to 8 carbon atoms. Alkoxy 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 an alkyl group having 1 to 5 carbon atoms and carbon atom number of carbon atoms are preferable. Alkoxy groups of 1 to 5, alkenyl groups having 2 to 5 carbon atoms, or alkenyloxy groups having 2 to 5 carbon atoms are preferable. R ¹¹ , R ²¹ and R ³¹ are independent of each other, more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 2 to 5 carbon atoms, and R ¹² , R ²² and R ³² are independent of each other. , An alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is more preferable.

When the ring structure to which the terminal groups ( ^RN11 , ^RN12 , ^RN21 , ^RN22 , ^RN31 and ^RN32 ) are bonded is a phenyl group (aromatic), the number of linear carbon atoms is 1 to 1. An alkyl group of 5 and a linear alkoxy group having 1 to 4 carbon atoms and an alkenyl group having 4 to 5 carbon atoms are preferable, and the ring structure to which the terminal group is bonded is a saturated ring such as cyclohexane, pyran and dioxane. In the case of the structure, 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 are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if any, 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.)

^{AN11, AN12, AN21, AN22, AN31 and AN32 are preferably aromatics when it} is required to increase Δn independently, and fat is used to improve the response rate. It is preferably a group, 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, preferably represented below. 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 are independently -CH ₂ O-, -CF ₂ O-, -CH ₂ CH _2- , -CF ₂ CF _2- or single bond, respectively. , -CH ₂ O-, -CH ₂ CH _2- or single bond is more preferable, and -CH ₂ O- or single bond is particularly preferable.

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 ^N11 is 1 and n ^N12 is 1, n ^N11 is 2 and n ^N12 is 1, n ^N21 is 1 and n ^N22 is 0, n ^N21 is 2 and n ^N22 is. 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 upper limit of the preferred 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 upper limit of the preferred 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 upper limit of the preferred 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 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 having good temperature stability is required, it is preferable that the lower limit value is low and the upper limit value is low. Further, when it is desired to increase the dielectric anisotropy in order to keep the 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).

(In the formula, ^RN11 and ^RN12 have the same meanings as ^RN11 and ^RN12 in the general formula (N-1), ^nNa12 represents 0 or 1, ^nNb11 represents 0 or 1, and ^nNc11 represents 0 or 1. Represents 0 or 1, n ^{Nd 11} represents 0 or 1, n Ne 11 represents 1 or 2, n N ^f12 represents 1 or 2, n ^{Ng 11} represents 1 or 2, and A ^{Ne 11} represents trans-1,4. -Representing a cyclohexylene group or a 1,4-phenylene group, A ^Ng11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group, but n ^Ng11. When 1 represents an 1,4-cyclohexenylene group, when n ^Ng11 is 2, at least one ^ANg11 represents a 1,4-cyclohexenylene group and Z ^Ne11 is a single bond or ethylene ^. When n ^Ne11 is 1, Z ^Ne11 represents an ethylene group. When n ^Ne11 is 2, at least one Z ^Ne11 represents an ethylene group.)
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.

(In the formula, ^RN111 and ^RN112 independently represent the same meanings as ^RN11 and ^RN12 in the general formula (N-1).)
^{The 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. ^{The 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when set to a small value. 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%. It is 17%, 20%, 23%, 25%, 27%, 30%, 33%, and 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 %, 5%, 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 (N1-1.1) to (N1-1.22). 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) are preferable. The compound represented by -1-1.3) is preferable.

The compounds represented by the formulas (N-1-1.1) to (N-1-1.22) 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%, and 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 %, 5%, and 3%.

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

(In the formula, ^RN121 and ^RN122 independently represent the same meanings as ^RN11 and ^RN12 in the general formula (N-1).)
The ^RN121 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, 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) 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.

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 if you set a large amount. 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 upper limit of the preferable content is 50%, 48%, 45%, 43%, 40%, 38%, and 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%, and 5%.

Further, the compound represented by the general formula (N-1-2) is a compound selected from the compound group represented by the formula (N-1-2.1) to the formula (N-1-2.22). 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 preferable that the compound is represented by (N-1-2.13) and the formula (N-1-2.20), and when the improvement of Δε is emphasized, the formula (N-1-2.3) is used. From the above, the compound represented by the formula (N- _1-2.7 ) is preferable, and when the improvement of TNI is emphasized, the formula (N1-2.10) and the formula (N-1-2.11) are used. 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-1-2.22) can be used alone or in combination, but the composition of the present invention. The lower limit of the preferred content of these compounds alone or these compounds relative to the total amount of is 5%, 10%, 13%, 15%, 17%, 20%, 23. %, 25%, 27%, 30%, 33%, 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 %, 5%, and 3%.

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

(In the formula, ^RN131 and ^RN132 independently represent the same meanings as ^RN11 and ^RN12 in the general formula (N-1).)
^{The 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. ^{The 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

Further, the compound represented by the general formula (N-1--3) is a compound selected from the compound group represented by the formula (N-1-3.21) to the formula (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 the formula (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 preferred.

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. Although it can be used in the above or in combination, the combination of the formula (N-1-3.1) and the formula (N-1-3.2) and the formula (N-1-3.3) can be used. ), A combination of 2 or 3 selected from the formula (N-1-3.4) and the formula (N-1-3.6) is preferable. The lower limit of the preferred content of the composition alone or of these compounds relative to the total amount of the composition 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%, and 13%.

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

(In the formula, ^RN141 and ^RN142 independently represent the same meanings as ^RN11 and ^RN12 in the general formula (N-1).)
^RN141 and ^RN142 are independent of each other, 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, preferably a methyl group, a propyl group, and an ethoxy group. Groups or butoxy groups are preferred.

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

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when set to a small value. 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-1-4.1) to (N-1-4.14). It is preferable that the compound is represented by the formulas (N-1-4.1) to (N-1-4.4), and the formula (N-1-4.1) and the formula (N) are preferable. The compounds represented by 1-4.4.2) and the formula (N-1-4.4) are preferable.

The compounds represented by the formulas (N-1-4.1) to (N-1-4.14) 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 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.

(In the formula, ^RN151 and ^RN152 independently represent the same meanings as ^RN11 and ^RN12 in the general formula (N-1).)
^RN151 and ^RN152 are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, preferably an ethyl group, a propyl group, or a butyl group. Is preferable.

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

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 if you set a large amount. 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 upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the composition of the present invention. %, 18%, 15%, and 13%.

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-1-5.6). 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 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 upper limit of the preferable content is 35%, 33%, 30%, 28%, 25%, 23%, and 20% with respect to the total amount of the composition of the present invention. %, 18%, 15%, and 13%.

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

(In the formula, ^RN1101 and ^RN1102 independently represent the same meanings as ^RN11 and ^RN12 in the general formula (N-1).)
The ^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. The ^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) 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.

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 set to a high value. 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%, and 13%.

Further, the compound represented by the general formula (N-1-10) is a compound selected from the compound group represented by the formula (N-1-10.14) to the formula (N-110.14). It is preferably present, and is represented by the formulas (N-1-10.1) to (N-1-10.5) formulas (N-110.13) and formulas (N-110.14). It is preferably a compound, preferably of formula (N-110.1), formula (N-1-10.2), formula (N-110.13) and formula (N-110.14). The compound represented by is preferable.

The compounds represented by the formulas (N-110.10), (N-1-10.2), (N-110.13) and (N-110.14) are independent. Although it can be used in combination or in combination, the lower limit of the preferable content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5% and 10%. , 13%, 15%, 17%, 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

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

(In the formula, ^RN1111 and ^RN1112 independently represent the same meanings as ^RN11 and ^RN12 in the general formula (N-1).)
^{The 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) 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.

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 set to a high value. 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%, and 13%.

Further, the compound represented by the general formula (N-1-111) 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 formula (N-1-11.2) and the formula (N) 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 composition of the present invention can be used. The lower limit of the preferred content of a single substance or these compounds with respect to the total amount of is 5%, 10%, 13%, 15%, 17%, and 20%. The upper limit of the preferable content is 35%, 30%, 28%, 25%, 23%, 20%, and 18% with respect to the total amount of the composition of the present invention. %, 15%, and 13%.

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

(In the formula, ^RN1121 and ^RN1122 independently represent the same meanings as ^RN11 and ^RN12 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

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

(In the formula, ^RN1131 and ^RN1132 independently represent the same meanings as ^RN11 and ^RN12 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, and 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

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

(In the formula, ^RN1141 and ^RN1142 independently represent the same meanings as ^RN11 and ^RN12 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, and 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

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

(In the formula, ^RN1151 and ^RN1152 independently represent the same meanings as ^RN11 and ^RN12 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, and preferably an ethyl group, a propyl group or a butyl group. ^{The 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

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

(In the formula, ^RN1161 and ^RN1162 independently represent the same meanings as ^RN11 and ^RN12 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, and preferably an ethyl group, a propyl group or a butyl group. ^{The 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

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

(In the formula, ^RN1171 and ^RN1172 independently represent the same meanings as ^RN11 and ^RN12 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, and 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

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

(In the formula, ^RN1181 and ^RN1182 independently represent the same meanings as ^RN11 and ^RN12 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

Further, the compound represented by the general formula (N-1-18) is a compound selected from the compound group represented by the formulas (N1-18.1) to (N1-18.5). It is preferable that the compound is represented by the formulas (N1-18.1) to (N1-18.3), and the formulas (N1-18.2) and the formula (N) are preferable. The compound represented by -1-18.3) is preferable.

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

(In the formula, ^RN1201 and ^RN1202 independently represent the same meanings as ^RN11 and ^RN12 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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%, and 13%.

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

(In the formula, ^RN1211 and ^RN1212 independently represent the same meanings as ^RN11 and ^RN12 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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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 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%, and 13%.

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

(In the formula, ^RN1221 and ^RN1222 have the same meanings as ^RN11 and ^RN12 in the general formula (N-1), respectively.)
^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) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high if you set it to a large extent. 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-1-22) 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-1-222.12). 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-2) is preferably a compound selected from the compound group represented by the following general formulas (N-2-1) to (N-2-3).

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

(In the formula, ^RN211 and ^RN212 independently represent the same meanings as ^RN21 and ^RN22 in the general formula (N-2).)
The compound represented by the general formula (N-2-2) is the following compound.

(In the formula, ^RN221 and ^RN222 independently represent the same meanings as ^RN21 and ^RN22 in the general formula (N-2).)
The compound represented by the general formula (N-2-3) is the following compound.

(In the formula, ^RN231 and ^RN232 independently represent the same meanings as ^RN21 and ^RN22 in the general formula (N-2).)
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).

(In the formula, ^RN321 and ^RN322 independently represent the same meanings as ^RN31 and ^RN32 in the general formula (N-3).)
^{The RN321} and ^RN322 are preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a propyl group or a pentyl group.

The compound represented by the general formula (N-3-2) 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.

When the improvement of Δε is emphasized, it is preferable to set the content high, when the solubility at low temperature is emphasized, the effect is high when the content is set high, and when the _TNI is emphasized, the content is high. The effect is high when set to a small value. 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%, and 35%. The upper limit of the preferable content is 50%, 40%, 38%, 35%, 33%, 30%, and 28% with respect to the total amount of the composition of the present invention. %, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6 % And 5%.

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

The liquid crystal composition according to the present invention preferably contains one or more compounds represented by the general formula (L) in addition to the compound represented by the general formula (I). The compound represented by the general formula (L) corresponds to a dielectrically almost neutral compound (value of Δε is -2 to 2).

(In the formula, ^RL1 and ^RL2 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent _−CH2- in the alkyl group are independent of each other. It may be substituted with -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-.
n ^L1 represents 0, 1, 2 or 3
A ^L1 , A ^L2 and A ^L3 are independently (a) 1,4-cyclohexylene groups (one -CH _2- existing in this group-or _two or more non-adjacent-CH 2--). May be replaced with -O-.)
(B) 1,4-Phenylene group (one -CH = existing in this group or two or more non-adjacent -CH = 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-A single -CH = present in a 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 groups (a), groups (b) and groups (c) may be independently substituted with cyano groups, fluorine atoms or chlorine atoms, respectively.
Z ^L1 and Z ^L2 are independently single-bonded, -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-
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, 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 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) is 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%, 40. %, 50%, 55%, 60%, 65%, 70%, 75%, 80%. The upper limit of the preferred 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 having 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. If so, 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.

When the ring structure to which ^RL1 and ^RL2 are bonded is a phenyl group (aromatic), ^RL1 and ^RL2 are independently linear alkyl groups having 1 to 5 carbon atoms and linear chains. Alkoxy groups having 1 to 4 carbon atoms and alkenyl groups having 4 to 5 carbon atoms are preferable, and when the ring structure to which ^RL1 and ^RL2 are bonded is a saturated ring structure such as cyclohexane, pyran and dioxane. , ^RL1 and ^RL2 are independent, linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, and linear carbon atoms 2 to 5. Alkoxy group is preferred. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if any, 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.

^AL1 , ^AL2 and ^AL3 are preferably aromatic when it is required to increase Δn, and preferably aliphatic in order to improve the response rate, and each of them is independently trans-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 is preferable to represent a diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and it is more preferable to represent 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 bonds when response speed is important.

The compound represented by the general formula (L) preferably has 0 or 1 halogen atom in the molecule. As the halogen atom, a fluorine atom or a chlorine atom is preferable, and a fluorine atom is more preferable.

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.

(In the formula, RL11 and ^RL12 independently represent the same meanings as ^RL1 and ^RL2 in the general formula ( ^L )).
^{RL11 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) 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 preferred content is 1%, 2%, 3%, 5%, 7%, 10%, 15 with respect to 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 having good temperature stability is required, it is preferable that the 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 it is a compound represented by the formula (L-1-1.2) or the formula (L-1-1.3), and in particular, it 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%. It is 17%, 20%, 23%, 25%, 27%, 30%, and 35%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 42%, 40%, and 38% with respect to the total amount of the composition of the present invention. %, 35%, 33%, and 30%.

Further, the compound represented by the general formula (L-1-2) is a compound selected from the compound group represented by the formula (L-1-2.1) to the formula (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 (L-1-2.4). 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%, 23%, 25%, 27%, 30%, 33%, 35%, 38%, and 40%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 43%, 40%, and 38% with respect to the total amount of the composition of the present invention. %, 35%, 32%, 30%, 27%, 25%, 22%.

The lower limit of the preferable total 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 upper limit of the preferable content is 60%, 55%, 50%, 45%, 43%, 40%, and 38% with respect to the total amount of the composition of the present invention. %, 35%, 32%, 30%, 27%, 25%, 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.)
^RL13 and ^RL14 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. ..

The lower limit of the 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 upper limit of the preferable content is 60%, 55%, 50%, 45%, 40%, 37%, and 35% with respect to the total amount of the composition of the present invention. %, 33%, 30%, 27%, 25%, 23%, 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 1-3.12). Total of compounds represented by formula (L-1-3.3), formula (L-1-3.4), formula (L-1-3.11) and formula (L-1-3.12). The content of the above 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. % And 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.)
^RL15 and ^RL16 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. ..

The lower limit of the 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 formulas (L-1-4.1) to (L-1-5.3). It is preferable that the compound is selected from the above-mentioned compound group, and it is preferable that the compound is represented by the formula (L-1-4.2) or the formula (L-1-5.2).

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. % And 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%, and 18%. , 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 compounds selected from the above, 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 kinds of compounds selected from the above 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 independently represent a methyl group or a hydrogen atom, respectively.)
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%. It is 17%, 20%, 23%, 25%, 27%, 30%, and 35%. The upper limit of the preferable content is 60%, 55%, 50%, 45%, 42%, 40%, and 38% with respect to the total amount of the composition of the present invention. %, 35%, 33%, and 30%.

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.

(In the formula, ^RL21 and ^RL22 independently represent the same meanings as ^RL1 and RL2 in the general 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-1) 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.

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 formula (L-2.1) to the formula (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.

(In the formula, ^RL31 and ^RL32 independently represent the same meanings as ^RL1 and RL2 in the general formula ( ^L )).
^{As RL31} and ^RL32 , 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 are preferable, respectively.

The compound represented by the general formula (L-3) 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-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 index is obtained, a large content is highly effective, and conversely, when a high Tni is emphasized, a low content is highly effective. 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 preferable that the compound is represented by the formula (L-3.7) from (L-3.2).

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

(In the formula, ^RL41 and ^RL42 independently represent the same meanings as ^RL1 and RL2 in the general 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) 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.

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, dripping 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) is contained. 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 the preferred upper limit is 45, 40%. , 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%. ..

When both the compound represented by the formula (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% and 30%, and the preferred upper limit is 45, 40%, 35% and 30%. Yes, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (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) is contained. 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%, and 21%. Preferred upper limits are 45, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13 %, 10%, and 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% and 30%, and the preferred upper limit is 45, 40%, 35% and 30%. Yes, 25%, 23%, 20%, 18%, 15%, 13%.

The compound represented by the general formula (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.

(In the formula, ^RL51 and ^RL52 independently represent the same meanings as ^RL1 and RL2 in the general 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) 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.

In the composition of the present invention, the content of the compound represented by the general formula (L-5) is solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dripping 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 compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2), and in particular, the compound represented by the formula (L-5. It is preferably a compound represented by 1).

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.

(In the formula, ^RL61 and ^RL62 independently represent the same meanings as ^{RL1 and RL2 in the general formula (L), and XL61 and XL62 independently} represent a hydrogen atom or a fluorine atom, respectively. )
^RL61 and ^RL62 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and one of ^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 the emphasis is on increasing Δn, it is preferable to increase the content, and when the emphasis is 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 compound 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), 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 them 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), 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.

(In the formula, ^RL71 and ^RL72 independently represent the same meanings as RL1 and RL2 in the general formula ( ^L ), and ^AL71 and ^AL72 independently represent ^AL2 and LL2 in the general formula ( ^L ), respectively. Although it has the same meaning as A ^L3 , the hydrogen atom on A ^L71 and A ^L72 may be independently substituted with a fluorine atom, and Z ^L71 has the same meaning as Z ^L2 in the general formula (L). ^XL71 and ^XL72 independently represent a fluorine atom or a hydrogen atom, respectively.)
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 are preferable. Is preferably a 1,4-cyclohexylene group or a 1,4-phenylene group independently, and hydrogen atoms on A ^L71 and A ^L72 may be independently substituted with fluorine atoms, respectively, and Z ^L71 is simply. Bonds or -COO- are preferable, single bonds are preferable, and hydrogen atoms are preferable for ^XL71 and ^XL72 .

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, two, three, and four 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) is solubility at low temperature, transition temperature, electrical reliability, birefringence, process compatibility, dripping 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. 31) or / and a compound represented by the formula (L-7.32) are preferable.

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), preferably the compound represented by the formula (L-7. 41) or / and a compound represented by the formula (L-7.42) are preferable.

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 liquid crystal composition according to the present invention contains a polymerizable monomer represented by the general formula (I) and a spontaneously oriented monomer, but other polymerizable compounds may be used in combination. That is, the liquid crystal composition according to the present invention preferably further contains a polymerizable compound represented by the general formula (II).
Examples of the other polymerizable compound include the general formula (II) :.

(In the formula, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , R ²⁰⁹ and R ²¹⁰ are independently converted into ^P21 - ^S21- and fluorine atoms, respectively. It represents any of an alkyl group having 1 to 18 carbon atoms which may be substituted, an alkoxy group having ¹ to 18 carbon atoms which may be substituted by a fluorine atom, a fluorine atom or a hydrogen atom, and P21 is the above general formula. Represents any of (RI) to (R-IX) of (I).
S ²¹ represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or more -CH _2- in the alkylene group is -O-, so that oxygen atoms are not directly adjacent to each other. May be substituted with -OCO- or -COO-,
n ²¹ represents 0, 1 or 2,
A ²¹ is
(A) 1,4-Cyclohexylene group (one -CH _2- or two or more non-adjacent -CH ₂ -existing in this group may be replaced with -O-).
(B) 1,4-Phenylene group (one -CH = existing in this group or two or more non-adjacent -CH = 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-A single -CH = present in a 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 groups (a), groups (b) and groups (c) are independently alkyl groups having 1 to 12 carbon atoms and 1 to 12 carbon atoms, respectively. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or P ²¹ -S ^21- .
It has at least one P ²¹ -S ²¹ -in one molecule of the above general formula (II) and has at least one P 21-S 21-.
L ²¹ is a single bond, -OCH _2- , -CH ₂ O-, -C ₂ H _4- , -OC ₂ H ₄ O-, -COO-, -OCO-, -CH = CR ^a -COO-,- CH = CR ^a -OCO-, -COO-CR ^{a = CH-, -OCO-CR a =} CH-,-(CH ₂ ) _z -COO-,-(CH ₂ ) _z -OCO-, -OCO- ( CH ₂ ) _z- , -COO- (CH ₂ ) _z- , -CH = CH-, -CF ₂ O-, -OCF _2- or -C≡C- (In the formula, R ^a is hydrogen independently. Represents an atom or an alkyl group having 1 to 3 carbon atoms, and in the above formula, z independently represents an integer of 1 to 4).
When a plurality of P ²¹ , S ²¹ , and A ²¹ are present, they may be the same or different from each other, except for the compound represented by the general formula (I). ) Is preferable.

The liquid crystal composition containing the polymerizable compound represented by the general formula (I) and the polymerizable compound represented by the general formula (II) is effective from the viewpoint of further reducing the occurrence of display defects.

In the above general formula (II), it is preferable to have 1 or 2 or more P ²¹ -S ²¹ -in one molecule of the compound represented by the general formula (II), and 4 or less P ²¹ -S ^21- . The number of P ²¹ -S ^21- present in one molecule of the general formula (II) is preferably 1 or more and 4 or less, more preferably 1 or more and 3 or less, and the general formula (II). The number of P ²¹ − S ²¹ − in the molecule of the compound represented by is particularly preferably 2 or 3.

That is, the compound represented by the general formula (II) has a structure in which two benzene rings and, if necessary, ring A ²¹ are linked, and P ²¹ -S ²¹ -is formed in these two benzene rings and ring A ²¹ . Since it has at least one compound, the compound represented by the general formula (II) exhibits an action / effect as a polymerizable compound.

In the above general formula (II), one or more selected from the group consisting of R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , R ²⁰⁹ and R ²¹⁰ . When is P ²¹ -S ^21- , it is preferable that any one or more of R ²⁰¹ , R ²⁰² , R ²⁰⁴ , R ²⁰⁷ , R ²⁰⁹ or R ²¹⁰ is P ²¹ -S ^21- . , R ²⁰¹ and R ²¹⁰ are more preferably P ²¹ -S ^21- .

In the above general formula (II), R ²⁰¹ and R ²¹⁰ are preferably P ²¹ -S ²¹ -independently, respectively, and in this case, R ²⁰¹ and R ²¹⁰ are the same P ²¹ -S ^21- . It may be different P ²¹ -S ^21- .

In the above general formula (II), R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , R ²⁰⁹ and R ²¹⁰ are independently P ²¹ -S ^21- . , An alkyl group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, and any of a fluorine atom or a hydrogen atom. In the case, the preferred number of carbon atoms of the alkyl group and the alkoxy group is 1 to 16, more preferably 1 to 10, still more preferably 1 to 8, still more preferably 1 to 6, and further. It is more preferably 1 to 4, and particularly preferably 1 to 3. Further, the alkyl group and the alkoxy group may be linear or branched, but linear is particularly preferable.

In the above general formula (II), R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ and R ²⁰⁹ are independently derived from ^P21 - ^S21- and the number of carbon atoms of 1. It is preferably an alkyl group of 3, a fluorine atom or a hydrogen atom, more preferably ^P21 - ^S21- , a fluorine atom or a hydrogen atom, and even more preferably a fluorine atom or a hydrogen atom.

P ²¹ is preferably of the formula (R-1), more preferably an acrylic group or a methacrylic group, and even more preferably a methacrylic group.

S ²¹ is preferably a single bond or an alkylene group having 1 to 3 carbon atoms, and more preferably a single bond.

In the above general formula (II), n ²¹ is preferably 0 or 1.

In the above general formula (II), A ²¹ is preferably a 1,4-phenylene group or a naphthalene-2,6-diyl group, and more preferably a 1,4-phenylene group.

In the above general formula (II), L ²¹ is a single bond, -OCH _2- , -CH ₂ O-, -C ₂ H _4- , -COO-, -OCO-, -CH = CH-COO-,-. CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -C ₂ H ₄ -COO-, -C ₂ H ₄ -OCO-, -OCO-C ₂ H _4- , -COO-C ₂ H _4- , -CH = CH-, -CF ₂ O-, -OCF _2- or -C≡C- are preferable.

The content of the polymerizable compound represented by the general formula (II) is 0.01 to 5% by mass, but the lower limit of the content is preferably 0.02% by mass, preferably 0.03% by mass, and 0. It is preferably 0.04% by mass, preferably 0.05% by mass, preferably 0.06% by mass, preferably 0.07% by mass, preferably 0.08% by mass, preferably 0.09% by mass, and 0.1. By mass% is preferable, 0.15% by mass is preferable, 0.2% by mass is preferable, 0.25% by mass is preferable, 0.3% by mass is preferable, 0.35% by mass is preferable, and 0.4% by mass is preferable. Is preferable, 0.5% by mass is preferable, 0.55% by mass is preferable, and the upper limit of the content is preferably 4.5% by mass, preferably 4% by mass, preferably 3.5% by mass, and 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, 0.9% by mass is preferable, and 0.85 by mass is preferable. 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, 0.6% by mass is preferable, and 0.55% by mass is preferable. Is preferable.

Of the entire liquid crystal composition (100% by mass) according to the present invention, the upper limit of the total content with the polymerizable compound represented by the general formula (I) and the general formula (II) is preferably 6% by mass. 5.8% by mass is preferable, 5.5% by mass is preferable, 5.2% by mass is preferable, 5% by mass is preferable, 4.8% by mass is preferable, 4.6% by mass is preferable, and 4.4% by mass is preferable. % Is preferable, 4.2% by mass is preferable, 4% by mass is preferable, 3.5% by mass is preferable, 3% by mass is preferable, 2.5% by mass is preferable, 2% by mass is preferable, and 1.5% by mass is preferable. % Is preferable, 1% by mass is preferable, 0.95% by mass is preferable, 0.9% by mass 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, 0.6% by mass is preferable, and 0.55% by mass is preferable.
The lower limit of the total content is preferably 0.02% by mass, preferably 0.03% by mass, preferably 0.04% by mass, preferably 0.05% by mass, preferably 0.06% by mass, and 0. .07% by mass is preferable, 0.08% by mass is preferable, 0.09% by mass is preferable, 0.1% by mass is preferable, 0.15% by mass is preferable, 0.2% by mass is preferable, and 0.25% by mass is preferable. By mass% is preferable, 0.3% by mass is preferable, 0.35% by mass is preferable, 0.4% by mass is preferable, and 0.5% by mass is preferable.

The compound represented by the general formula (II) according to the present invention is preferably a polymerizable compound represented by the general formula (IV).

In the general formula (IV), R ⁷ and R ⁸ independently represent any of the above formulas (R-1) to (R-9), and X ¹ to X ⁸ are independent of each other. Represents a trifluoromethyl group, a fluorine atom or a hydrogen atom.

In the above general formula (IV), it is preferable that R ⁷ and R ⁸ are independently methacrylic groups or acrylic groups, respectively.

The compound represented by the general formula (IV) is more preferably one kind or two or more kinds selected from the group consisting of the formulas (IV-11) to (IV-15), and more preferably the formula (IV-). 11) is particularly preferable.

When the polymerizable compound represented by the formulas (IV-11) to (IV-15) is used in combination with the general formula (I), a better orientation state can be obtained.

Specifically, the compound represented by the general formula (II) according to the present invention is preferably, for example, a compound represented by the general formula (XX-1) to the general formula (XX-13), and the formula (XX-1). The formula (XX-7) is more preferable.

From the formula (XX-1) to the general formula (XX-13), Sp ^xx is an alkylene group having 1 to 8 carbon atoms or -O- (CH ₂ ) _s- (in the formula, s is an integer from 1 to 7). It represents, and the oxygen atom is assumed to be bonded to the ring.).

From the formula (XX-1) to the general formula (XX-13), the hydrogen atom in the 1,4-phenylene group is further added to -F, -Cl, -CF ₃ , -CH ₃ or the formula (R-1). May be replaced by any of the formulas (R-15).

Further, as the compound represented by the general formula (II), for example, a polymerizable compound represented by the formulas (M1) to (M18) is preferable.

Further, polymerizable compounds such as those of the formulas (M19) to (M34) are also preferable.

The hydrogen atoms in the 1,4-phenylene group and the naphthalene group in the formula (M19) to the formula (M34) may be further substituted with —F, —Cl, _—CF3 , _—CH3 .

Further, as the compound represented by the general formula (II), a polymerizable compound represented by the formulas (M35) to (M65) is also preferable.

In the liquid crystal composition according to the present invention, the content of the polymerizable compound represented by the formulas (M1) to (M65) in the entire liquid crystal composition is 0.01 to 5% by mass, but the lower limit of the content. Is preferably 0.02% by mass, preferably 0.03% by mass, preferably 0.04% by mass, preferably 0.05% by mass, preferably 0.06% by mass, preferably 0.07% by mass, and 0. .08% by mass is preferable, 0.09% by mass is preferable, 0.1% by mass is preferable, 0.15% by mass is preferable, 0.2% by mass is preferable, 0.25% by mass is preferable, and 0.3 by mass is preferable. By mass% is preferable, 0.35% by mass is preferable, 0.4% by mass is preferable, 0.5% by mass is preferable, 0.55% by mass is preferable, and the upper limit of the content is preferably 4.5% by mass. 4% by mass is preferable, 3.5% by mass is preferable, 3% by mass is preferable, 2.5% by mass is preferable, 2% by mass is preferable, 1.5% by mass is preferable, 1% by mass is preferable, and 0. 95% by mass is preferable, 0.9% by mass 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, and 0.65% by mass is preferable. % Is preferable, 0.6% by mass is preferable, and 0.55% by mass is preferable.

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.

Examples of the antioxidant include hindered phenol represented by the general formula (H-1) to the general formula (H-4).

From the general formula (H-1) to the general formula (H-4), ^RH1 is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms. Represents an alkoxyoxy group having 2 to 10 carbon atoms, but one -CH _2- or two or more non-adjacent-CH ₂ -existing in the group is independently -O- or -S-, respectively. In addition, one or more hydrogen atoms present in the group may be independently substituted with a fluorine atom or a chlorine atom, respectively. More specifically, it may be an alkyl group having 2 to 7 carbon atoms, an alkoxy group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms. It is more preferable that it is an alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms.

In the general formula (H-4), ^MH4 is an alkylene group having 1 to 15 carbon atoms (one or two or more -CH _2- in the alkylene group is -CH 2- so that oxygen atoms are not directly adjacent to each other-. It may be replaced with O-, -CO-, -COO-, -OCO-), -OCH _2- , -CH ₂ O-, -COO-, -OCO-, -CF ₂ O-,- OCF _2- , -CF ₂ CF _2- , -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-,- C≡C-, single bond, 1,4-phenylene group (any hydrogen atom in the 1,4-phenylene group may be substituted with a fluorine atom) or trans-1,4-cyclohexylene group. Although it is represented, it is preferably an alkylene group having 1 to 14 carbon atoms, and a large number of carbon atoms is preferable in consideration of volatileness, but it is preferable that the number of carbon atoms is not too large in consideration of viscosity. The number of carbon atoms is more preferably 2 to 12, the number of carbon atoms is 3 to 10, the number of carbon atoms is 4 to 10, the number of carbon atoms is 5 to 10, and the number of carbon atoms is 6 to 10.

In the general formula (H-1) to the general formula (H-4), one in the 1,4-phenylene group or two or more non-adjacent -CH = may be substituted with -N =. Further, the hydrogen atom in the 1,4-phenylene group may be independently substituted with a fluorine atom or a chlorine atom.

From the general formula (H-1) to the general formula (H-4), one in the 1,4-cyclohexylene group or two or more non-adjacent -CH ₂ -s are substituted with -O- or -S-. It may have been done. Further, the hydrogen atom in the 1,4-cyclohexylene group may be independently substituted with a fluorine atom or a chlorine atom.

More specifically, for example, formulas (H-11) to formulas (H-15) can be mentioned.

When the liquid crystal composition of the present invention contains an antioxidant, it is preferably 10% by mass or more, preferably 20% by mass or more, and preferably 50% by mass or more. When the antioxidant is contained, the upper limit is 10,000 mass ppm, but 1000 mass ppm is preferable, 500 mass ppm is preferable, and 100 mass ppm is preferable.

The liquid crystal composition of the present invention has a dielectric anisotropy (Δε) at 20 ° C. of −2.0 to −8.0, preferably −2.0 to −6.0, and preferably −2.0 to −2.0. -5.0 is more preferable, and -2.5 to -5.0 is particularly preferable.

The liquid crystal composition of the present invention has a refractive index anisotropy (Δn) of 0.08 to 0.14 at 20 ° C., more preferably 0.09 to 0.13, and more preferably 0.09 to 0.12. Especially 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 10 to 50 mPa · s, preferably 10 to 45 mPa · s, preferably 10 to 40 mPa · s, and 10 to 35 mPa. -S is preferable, 10 to 30 mPa · s is preferable, 10 to 25 mPa · s is more preferable, and 10 to 22 mPa · s is particularly preferable.

The liquid crystal composition of the present invention has a rotational viscosity (γ ₁ ) at 20 ° C. of 50 to 160 mPa · s, preferably 55 to 160 mPa · s, preferably 60 to 160 mPa · s, and 60. From 60 to 150 mPa · s, preferably 60 to 140 mPa · s, preferably 60 to 130 mPa · s, preferably 60 to 125 mPa · s, and preferably 60 to 120 mPa · s. It is more preferably 60 to 115 mPa · s, more preferably 60 to 110 mPa · s, and particularly preferably 60 to 100 mPa · s.

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

For example, when the entire liquid crystal composition according to the present invention exhibits negative permittivity anisotropy, a spontaneously oriented monomer, a polymerizable monomer represented by the general formula (I), and a general formula (N-1). It is preferable to include one kind or two or more kinds of compounds selected from the compounds represented by (N-2) and (N-3), and a compound represented by the general formula (L).

Of the entire liquid crystal composition according to the present invention, one or more spontaneously oriented monomers, one or more polymerizable monomers represented by the general formula (I), and the general formula (N-). 1), the upper limit of the ratio occupied only by the compound represented by the general formula (N-2), the general formula (N-3) and the general formula (L) is 100% by mass and 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 It is preferably mass%, 85% by mass, and 84% by mass.

Further, among the entire liquid crystal composition according to the present invention, one kind or two or more kinds of spontaneously oriented monomers, one kind or two or more kinds of polymerizable monomers represented by the general formula (I), and general formulas ( The lower limit of the proportion of the component composed only of the compounds represented by N-1), the general formula (N-2), the general formula (N-3) and the general formula (L) is 78% by mass, 80. Mass%, 81% by mass, 83% by mass, 85% by mass, 86% by mass, 87% by mass, 88% by mass, 89% by mass, 90% by mass, 91% by mass, 92% by mass, 93% by mass, 94% by mass. , 95% by mass, 96% by mass, 97% by mass, 98% by mass, and 99% by mass are preferable.

Of the entire liquid crystal composition according to the present invention, one or more spontaneously oriented monomers, one or more polymerizable monomers represented by the general formula (I), and the general formula (N-). 1a), general formula (N-1b), general formula (N-1c), general formula (N-1d), general formula (N-1e) and general formula (L). The upper limit of the ratio of the components 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. It is preferably 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, one kind or two or more kinds of spontaneously oriented monomers, one kind or two or more kinds of polymerizable monomers represented by the general formula (I), and general formulas ( Consists only of compounds represented by N-1a), general formula (N-1b), general formula (N-1c), general formula (N-1d), general formula (N-1e) and general formula (L). The lower limit of the ratio occupied by the components 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% by mass, 98% by mass, 99% by mass.

Of the entire liquid crystal composition according to the present invention, one or more spontaneously oriented monomers, a polymerizable monomer represented by the general formula (I), and a polymerizable compound represented by the general formula (II). Is represented by the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), the general formula (N-1e), 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, and 85% by mass are preferable.

Further, among the entire liquid crystal composition according to the present invention, one or more spontaneously oriented monomers, the polymerizable monomer represented by the general formula (I), and the polymerization represented by the general formula (II). With the sex compound, the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), the general formula (N-1e) and the general formula (L). The lower limit of the ratio of the component composed only of the represented 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, It is preferably 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, and 98% by mass.

Of the entire liquid crystal composition according to the present invention, one or more spontaneously oriented monomers, a polymerizable monomer represented by the general formula (I), and a polymerizable compound represented by the general formula (II). Is represented by the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), the general formula (N-1e), 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, and 85% by mass are preferable.

Further, among the entire liquid crystal composition according to the present invention, one or more spontaneously oriented monomers, the polymerizable monomer represented by the general formula (I), and the polymerization represented by the general formula (II). With the sex compound, the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), the general formula (N-1e) and the general formula (L). The lower limit of the ratio of the component composed only of the represented 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, It is preferably 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, and 98% by mass.

Of the entire liquid crystal composition according to the present invention, one or more spontaneously oriented monomers, two or more polymerizable monomers represented by the general formula (II-1), and the general formula (N-1a). ), General formula (N-1b), general formula (N-1c), general formula (N-1d), general formula (N-1e) and general formula (L). The upper limit of the ratio 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, and 85% by mass are preferable.

Further, among the entire liquid crystal composition according to the present invention, one or more spontaneously oriented monomers, two or more polymerizable monomers represented by the general formula (II-1), and the general formula (N). -1a), general formula (N-1b), general formula (N-1c), general formula (N-1d), general formula (N-1e) and general formula (L). The lower limit of the proportion of the components 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, It is preferably 91% by mass, 92% by mass, 93% by mass, 94% by mass, 95% by mass, 96% by mass, 97% by mass, and 98% by mass.

In addition, the liquid crystal composition according to the present invention has one or more spontaneously oriented monomers and one or more polymerizable monomers represented by the general formula (I) when orientation is important. Indispensably include a monomer and a general formula (N-1-1), a general formula (N-1-2), a general formula (N-1-3) or a general formula (N-1--4). Is preferable.

Further, the liquid crystal composition according to the present invention has one or more spontaneously oriented monomers and one or more polymerizable monomers represented by the general formula (I) when the response speed is emphasized. The monomer is essentially contained, and it is preferable that the general formula (N-1-10) or the general formula (N-1-11) is contained.
In addition, the liquid crystal composition according to the present invention has one or more spontaneously oriented monomers and one or more polymerizable monomers represented by the general formula (I) when orientation is important. A monomer and one or more kinds of polymerizable compounds represented by the general formula (II) are essentially contained, and the general formula (N-1-1), the general formula (N-1-2), and the general formula are included. It is preferable to include the formula (N-1-3) or the general formula (N-1-4).

Further, the liquid crystal composition according to the present invention has one or more spontaneously oriented monomers and one or more polymerizable monomers represented by the general formula (I) when the response speed is emphasized. Essentially comprising a monomer and one or more polymerizable compounds represented by the general formula (II), including the general formula (N-1-10) or the general formula (N-1-11). Is preferable.

Further, in the liquid crystal composition according to the present invention, when orientation is emphasized, one kind or two or more kinds of spontaneously oriented monomers and two or more kinds of polymerizable compounds represented by the general formula (II-1) are used. And, indispensably, and may include a general formula (N-1-1), a general formula (N-1-2), a general formula (N-1-3), or a general formula (N-1--4). preferable.

Further, in the liquid crystal composition according to the present invention, when the response speed is emphasized, one kind or two or more kinds of spontaneously oriented monomers and two or more kinds of polymerizable compounds represented by the general formula (II-1) are used. And are essentially included, and it is preferable to include the general formula (N-1-10) or the general formula (N-1-11).

Of the entire liquid crystal composition according to the present invention, the general formula (N-1-4), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), and the general formula (N-). The upper limit of the ratio of the component composed only of the compound represented by 1e) and the general formula (L) is 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.

Further, among the entire liquid crystal composition according to the present invention, the general formula (N-1-4), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), and the general formula (N-1d) The lower limit of the proportion of the component composed only of the compound represented by N-1e) and the general formula (L) is 78% by mass, 80% by mass, 81% by mass, 83% by mass, 85% by mass, 86. 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. Is preferable.

Of the entire liquid crystal composition according to the present invention, the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), and the general formula (N-1e). , General formula (L-1), general formula (L-3), general formula (L-4), general formula (L-5) and general formula (L-6). The upper limit of the ratio of the components is 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. It is preferably 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, and 80% by mass.

Further, among the entire liquid crystal composition according to the present invention, the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), and the general formula (N-). 1e) and composed only of compounds represented by 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 lower limit of the ratio occupied by the components 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% 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. It is preferably by mass%.

The liquid crystal display element 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 it does not matter whether there is an unreacted polymerizable compound or not. Since the voltage retention rate (VHR) is high, the voltage retention rate (VHR) is high, so that there are no problems such as misalignment and display failure, and the voltage retention rate (VHR) is 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 manufacturing, 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 is a liquid crystal display element for PSA mode, PSVA mode, VA mode, PS-IPS mode or PS-FFS mode. Can be used for.

The liquid crystal display element according to the present invention includes a first substrate and a second substrate arranged opposite to each other, a common electrode provided on the first substrate or the second substrate, and the first substrate or the above. It is preferable to have a pixel electrode provided on the second substrate and having a thin film transistor, and a liquid crystal layer containing 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 be in 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 to improve the viewing angle and contrast. 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.

The second aspect of the present invention is a liquid crystal composition used for a liquid crystal display element having no alignment film on the surface of at least one of a pair of substrates, and contains a polymerizable compound having two or more kinds of biphenyl skeletons. It is a liquid crystal composition. When two or more kinds of polymerizable compounds having a biphenyl group are contained, the reaction rate differs, so that uneven orientation and display defects can be reduced.

The polymerizable compound having a biphenyl skeleton may be any compound having a biphenyl skeleton in which two benzene rings are directly linked, and is a concept including terphenyl. Therefore, a polymerizable compound having two or more kinds of biphenyl skeletons means that there are two or more kinds of polymerizable compounds having a biphenyl skeleton in which two benzene rings are directly linked.

The polymerizable compound having a biphenyl group according to the present invention has the following formula (II-1):

(In the above general formula (II-1), R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , R ²⁰⁹ , R ²¹⁰ , R ²¹¹ , R ²¹² , R ²¹³ and R ²¹⁴ is independently P ²¹ -S ^21- , an alkyl group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, and an alkoxy group having 1 to 18 carbon atoms which may be substituted with a fluorine atom. , Halogen atom (fluorine atom) or hydrogen atom, P ²¹ represents any of (RI) to (R-IX) of the above general formula (I), and S ²¹ represents a single bond or Representing an alkylene group having 1 to 15 carbon atoms, one or more -CH _2- in the alkylene group is -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other. It may be substituted with, and n ²¹ is preferably represented by 0, 1 or 2).

In the above general formula (II-1), it is preferable to have 1 or 2 or more P ²¹ -S ²¹ -in one molecule of the compound represented by the general formula (II-1), and P ²¹ of 4 or less. It is preferable to have —S ²¹ −, and the number of P ²¹ −S ²¹ − present in one molecule of the general formula (II) is preferably 1 or more and 4 or less, more preferably 1 or more and 3 or less, and the above general. It is particularly preferable that the number of P ²¹ − S ²¹ − in the molecule of the compound represented by the formula (II) is 2 or 3.

That is, the compound represented by the general formula (II-1) has two benzene rings (biphenyl structure), and has at least one P ²¹ -S ^21- in these two benzene rings. Therefore, the compound represented by the general formula (II) exhibits an action / effect as a polymerizable compound.

In the above general formula (II-1), when one kind or two or more kinds of P ²¹ -S ^21- are included, any one of R ²⁰¹ , R ²⁰² , R ²⁰⁴ , R ²⁰⁷ , R ²⁰⁹ or R ²¹⁰ is included. Alternatively, it is preferable that two or more kinds are P ²¹ -S ^21- , and it is more preferable that R ²⁰¹ and R ²¹⁰ are P ²¹ -S ^21- .

In the above general formula (II-1), R ²⁰¹ and R ²¹⁰ are preferably P ²¹ -S ²¹ -independently, respectively, and in this case, R ²⁰¹ and R ²¹⁰ are the same P ²¹ -S ²¹ . -Or, it may be a different P ²¹ -S ^21- .

In the above general formula (II), R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , R ²⁰⁹ , R ²¹⁰ , R ²¹¹ , R ²¹² , R ²¹³ and R ²¹⁴ are Independently, P ²¹ -S ^21- , an alkyl group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, an alkoxy group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, and a fluorine atom. Alternatively, it represents either a hydrogen atom, and in this case, the alkyl group and the alkoxy group preferably have 1 to 16 carbon atoms, more preferably 1 to 10 atoms, still more preferably 1 to 8 atoms. It is even more preferably 1 to 6, even more preferably 1 to 4, and particularly preferably 1 to 3. Further, the alkyl group and the alkoxy group may be linear or branched, but linear is particularly preferable.

In the above general formula (II-1), R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , R ²⁰⁹ , R ²¹⁰ , R ²¹¹ , R ²¹² , R ²¹³ and R. Each of ²¹⁴ is preferably P ²¹ -S ^21- , an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a fluorine atom or a hydrogen atom, and P ²¹ -S ²¹ . -, It is more preferably a fluorine atom or a hydrogen atom, and more preferably a fluorine atom or a hydrogen atom.

In the above general formula (II-1), P ²¹ is preferably of the formula (RI), more preferably of an acrylic group or a methacrylic group, and even more preferably of a methacrylic group.

In the above general formula (II-1), S ²¹ is preferably a single bond or an alkylene group having 1 to 3 carbon atoms, and more preferably a single bond.

In the above general formula (II-1), n ²¹ is preferably 0.

The liquid crystal composition according to the present invention preferably contains 2 to 6 kinds of polymerizable compounds having a biphenyl group represented by the above general formula (II-1), and more preferably 2 to 5 kinds. It is more preferable to include 2 to 4 types, further preferably to contain 2 to 3 types, and particularly preferably 2 types. When two or more kinds of polymerizable compounds having a biphenyl group represented by the above general formula (II-1) having different chemical structures are contained, the reaction rate differs, so that uneven orientation and display defects can be reduced. can.

Further, as one of the polymerizable compounds having two or more kinds of biphenyl skeletons, the compound represented by the general formula (Ia) may be used.

Examples of the polymerizable compound having a biphenyl skeleton that can be suitably used for the liquid crystal composition according to the present invention include a polymerizable compound represented by the above formula (XX-1) to the general formula (XX-13), and the above formula RM-1. RM-14 and formula I-1-1 to formula I-7-6.

Therefore, in the liquid crystal composition according to the present invention, as a preferred embodiment of the polymerizable compound having two or more kinds of biphenyl skeletons, the polymerizable compound represented by the above formula (XX-1) to the general formula (XX-13) is possible. Two kinds selected from the group consisting of a compound, a polymerizable compound represented by the above formulas RM-1 to RM-14, and a polymerizable compound represented by the formulas I-1-1 to I-7-6. ..

The total content of the polymerizable compound having two or more kinds of biphenyl skeletons is 0.02 to 10% by mass, but the lower limit of the content is 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, 0.15% by mass is preferable, 0.2% by mass is preferable, 0.25% by mass is preferable, 0.3% by mass is preferable, 0.35% by mass is preferable, and 0.4% by mass is preferable. % Is preferable, 0.5% by mass is preferable, 0.55% by mass is preferable, and the upper limit of the content is 5% by mass, 4.5% by mass is preferable, 4% by mass is preferable, and 3.5% by mass is preferable. Preferably, 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. Preferably, 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. 0.55% by mass is preferable.

The liquid crystal composition according to the present invention preferably contains a spontaneously oriented monomer having a chemical structure different from that of each of the polymerizable compounds having two or more kinds of biphenyl skeletons and having a polar group.

As the spontaneously oriented monomer, the above-mentioned spontaneously oriented monomer can be preferably used.

Further, as a preferred embodiment of the liquid crystal composition according to the present invention, two or more kinds of polymerizable compounds having a biphenyl group represented by the above general formula (II-1) and one kind or one of the above-mentioned spontaneously oriented monomers are used. It contains two or more kinds, a group of compounds represented by the general formulas (N-1a) to (N-1g), and a compound represented by the general formula (L), and these compounds are 85 to 85 of the liquid crystal composition. It preferably occupies 100% by mass.

A third aspect of the present invention is a first substrate and a second substrate arranged opposite to each other, a liquid crystal layer filled between the first substrate and the second substrate, and the first substrate. Each pixel has a plurality of gate bus lines and data bus lines arranged in a matrix, a thin film transistor provided at an intersection of the gate bus line and the data bus line, and a pixel electrode driven by the thin film transistor. A polymerizable compound having two or more kinds of biphenyl skeletons between the electrode layer, the common electrode formed on the first substrate or the second substrate, and the first substrate and the second substrate. A liquid crystal display element having a cured resin component and having at least one of the substrate surfaces having no alignment film.
As a method for polymerizing the polymerizable compound or the polymerizable monomer and the spontaneously oriented monomer 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. A method of polymerizing by irradiating an active energy ray such as an electron beam alone, in 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 the polymerization is carried out in a state where the liquid crystal composition is sandwiched between two substrates, at least the substrate on the irradiation surface side must be provided with appropriate transparency to the active energy rays. In addition, after polymerizing only a specific part using a mask during light irradiation, the orientation 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 the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In the liquid crystal display element in the PSVA mode, it is preferable to control the pretilt angle from 80 degrees to 89.9 degrees from the viewpoint of orientation stability and contrast.

The temperature at the time of irradiation with active energy rays such as ultraviolet rays or electron beams used for 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. A temperature range wider than the temperature range may be used.

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 region 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.

The third of the present invention is a compound represented by the general formula (I).

(In the above general formula (I), R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ are independently P ¹¹ -S ¹¹ respectively. -, Represents any of an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom, and P ¹¹ is represented by the following formula (RI) to formula (R-). Represents one of IX)

(In the above formulas (RI) to (R-IX), R ²¹ , R ³¹ , R ⁴¹ , R ⁵¹ and R ⁶¹ are independent of each other and have a hydrogen atom and an alkyl group having 1 to 5 carbon atoms. W is a single bond, —O— or a methylene group, T is a single bond or —COO—, and p, t and q are independently 0, 1 or 2 respectively.)
S ¹¹ represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or more -CH _2- in the alkylene group is -O-, so that oxygen atoms are not directly adjacent to each other. May be substituted with -OCO- or -COO-,
n ¹¹ represents 0, 1 or 2,
A ¹¹ is the following group (a), group (b) and group (c):
(A) 1,4-Cyclohexylene group (one -CH _2- or two or more non-adjacent -CH ₂ -existing in this group may be replaced with -O-).
(B) 1,4-Phenylene group (one -CH = existing in this group or two or more non-adjacent -CH = 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-A single -CH = present in a 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 groups (a), groups (b) and groups (c) are independently alkyl groups having 1 to 12 carbon atoms and 1 to 12 carbon atoms, respectively. It may be substituted with an alkoxy group, a halogen, a cyano group, a nitro group or ^P11 - ^S11- .
L ¹⁰ and L ¹¹ are independently single-bonded, -OCH _2- , -CH ₂ O-, -C ₂ H _4- , -OC ₂ H ₄ O-, -COO-, -OCO-,-, respectively. CH = CR ^a -COO-, -CH = CR ^a -OCO-, -COO-CR ^a = CH-, -OCO-CR ^a = CH-,-(CH ₂ ) _z -COO-,-(CH ₂ ) _z -OCO-, -OCO- (CH ₂ ) _z- , -COO- (CH ₂ ) _z- , -CH = CH-, -CF ₂ O-, -OCF _2- or -C≡C- (in the formula) , Ra independently represent ^a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and z in the above formula independently represent an integer of 1 to 4).
It has at least two or more P ¹¹ -S ¹¹ -in one molecule of the above general formula (I), and has.
One molecule of the above general formula (I) has an alkyl group having 1 to 18 carbon atoms, and one or _two or more non-adjacent alkyl groups in the alkyl group are independently of each other. May be replaced by O-
When a plurality of P ¹¹ , S ¹¹ , L ¹¹ and A ¹¹ exist, they may be the same or different from each other. )
The preferred form of the compound represented by the general formula (I) according to the present invention is as described above. The most preferable form of the compound represented by the general formula (I) according to the present invention is, that is, in the above general formula (I), A ¹¹ is an alkyl group having 1 to 12 carbon atoms and 1 to 1 carbon atom. It is a 1,4-phenylene group which may be substituted with ¹² alkoxy groups, halogens, cyano groups, nitro groups or P11- ^S11- .
Both L ¹⁰ and L ¹¹ are single bonds, and they are single bonds.
R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ are independently P ¹¹ -S ^11- and have 1 to 10 carbon atoms, respectively. Represents a chain alkyl group, a linear alkoxy group having 1 to 10 carbon atoms, a halogen atom or a hydrogen atom.
It has at least two or more P ¹¹ -S ¹¹ -in one molecule of the polymerizable monomer represented by the general formula (I).
Alkyl groups having 1 to 10 carbon atoms in one molecule of the above general formula (I) (one in the alkyl group or two or more non-adjacent _—CH2 −s are independently formed by —O—. Have at least one (may be substituted)
n ¹¹ represents 0 or 1 and represents
It is particularly preferable that P ¹¹ is the above formula (R-1) and S ¹¹ is a single bond or an alkylene group having 1 to 3 carbon atoms.

Hereinafter, the synthesis of an example of the compound represented by the general formula (I) according to the present invention will be described.

Production of compound represented by the general formula (RM-3) Suzuki coupling reaction of 4-bromo-2,6-dimethylphenol and 4-bromo-2,6-dimethylphenol using a palladium catalyst was carried out (S). -1) is obtained. Then, deacetalization is performed, and the desired product (RM-3) can be obtained by an esterification reaction with methacrylic acid.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. Further, "%" in the compositions of the following Examples and Comparative Examples means "% by mass". The following abbreviations are used for the description of compounds in the examples.

(Synthesis Example 1)
"Method of synthesizing RM-3"
20 g of 4-bromo-2,6-dimethylphenol, 100 ml of 2 mol / l potassium carbonate aqueous solution, dichlorobis [di-t-butyl (p-dimethylaminophenol) phosphino] in a reaction vessel equipped with a stirrer, a cooler, and a dropping funnel. 3.5 g of palladium and 100 ml of THF were charged and stirred at 50 ° C. 100 ml of a THF solution of 24 g of 4-benzyloxyphenylboronic acid was slowly added dropwise. The reaction was carried out at 50 ° C. for 5 hours. After completion of the reaction, the mixture was cooled, 200 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, the solvent was distilled off, purification was performed with a silica gel column, and recrystallization was performed with hexane / ethyl acetate. -26 g of benzyloxy-3,5-dimethyl-4-biphenol was obtained.

18 g of 4'-benzyloxy-3,5-dimethyl-4-biphenol and 100 ml of THF were added to the autoclave, and the mixture was stirred at 50 ° C. for 3 hours under a hydrogen pressure of 0.5 MPa. After the reaction, the filtrate was filtered through cellulose, washed with THF, concentrated, purified with a silica gel column, and washed with hexane to obtain 13 g of the target compound 4,4'-dihydroxy-3,5-biphenyl. ..

Further, in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 8 g (37 mmol) of synthesized 4,4'-dihydroxy-3,5-biphenyl, 7.1 g (82 mmol) of methacrylic acid, and dimethylaminopyridine 0 .23 g and 160 ml of dichloromethane were charged, and the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 11 g (90 mmol) of diisopropylcarbodiimide was slowly added dropwise. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 11 hours. After filtering the reaction solution, 150 ml of dichloromethane 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 performed by column chromatography using silica gel to obtain 11 g of the target compound represented by the formula (RM-3).

The physical property values ( ¹ H-NMR, ¹³ C-NMR and melting point) of the obtained compound are as follows. Physical characteristics: ^{1 1} H-NMR (solvent: deuterated chloroform): δ: 7.57-7.54 (m, 2 H), 7.26 (s, 2 H), 7.19-7.15 (m, 2H), 6.39 (d, 2H), 5.76 (dq, 2H), 2.21 (s, 6H), 2.11 (d, 3H), 2.07 (d, 3 H)
¹³ C-NMR (solvent: deuterated chloroform): δ 165.8, 165.1, 150.2, 147.8, 138.4, 138.0, 135.8, 135.5, 130.5, 130. 5, 128.0, 128.0, 127.3, 127.3, 127.2, 127.1, 121.7, 121.7, 18.4, 18.3, 16.4, 16.4
Melting point: 111 ° C
(Synthesis Example 2)
"Method of synthesizing RM-4"
In a reaction vessel equipped with a stirrer, a cooler, and a dropping funnel, 10 g of 4-bromo-3,5-dimethylphenol, 50 ml of a 2 mol / l potassium carbonate aqueous solution, dichlorobis [di-t-butyl (p-dimethylaminophenol) phosphino] 1.8 g of palladium and 50 ml of THF were charged and stirred at 50 ° C. 36 ml of a THF solution of 12 g of 4-benzyloxyphenylboronic acid was slowly added dropwise. The reaction was carried out at 50 ° C. for 4 hours. After completion of the reaction, the mixture was cooled, 50 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, the solvent was distilled off, purification was performed with a silica gel column, and washing with hexane / ethyl acetate was performed. 13 g of benzyloxy-2,6-dimethyl-4-biphenol was obtained.

11 g of 4'-benzyloxy-2,6-dimethyl-4-biphenol and 100 ml of THF were added to the autoclave, and the mixture was stirred at 50 ° C. for 3 hours under a hydrogen pressure of 0.5 MPa. After the reaction, the filtrate was filtered with cellulose, washed with THF, concentrated, purified with a silica gel column, and washed with hexane to obtain 7 g of the target compound 4,4'-dihydroxy-2,6-biphenyl. ..

Further, in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 7 g (32 mmol) of 4,4'-dihydroxy-2,6-biphenyl, 6.0 g (70 mmol) of methacrylic acid, 0.2 g of dimethylaminopyridine. , 140 ml of dichloromethane was charged, the reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 50 ml of THF in which 9.6 g (76 mmol) of diisopropylcarbodiimide was dissolved was slowly added dropwise. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 15 hours. After filtering the reaction solution, 120 ml of dichloromethane 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 performed by column chromatography using amino silica gel, and further dispersion washing with methanol was performed. After precipitation at −20 ° C., filtration and vacuum drying were carried out to obtain 11 g of the target compound represented by the formula (RM-4).

The physical property values ( ¹ H-NMR, ¹³ C-NMR and melting point) of the obtained compound are as follows. Physical characteristics: ^{1 1} H-NMR (solvent: deuterated chloroform): δ7.64-7.54 (m, 4H), 7.26 (s, 2H), 6.75 (d, 2H), 6. 15 (dq, 2H), 2.48-2.46 (m, 6H), 2.43 (s, 6H)
¹³ C-NMR (solvent: deuterated chloroform): δ166.4, 166.1, 150.1, 149.9, 138.8, 138.1, 136.3, 136.2, 130.5, 130.5 , 128.4, 128.4, 127.5, 127.4, 122.2, 121.9, 120.4, 120.4, 21.3, 21.2, 18.7, 18.7
Melting point: 89 ° C
(Synthesis Example 3)
"Method of synthesizing RM-7"
In a reaction vessel equipped with a stirrer, cooler and thermometer under a nitrogen atmosphere, 25 g of 1-benzyloxy-2-bromobenzene, 10 g of triethylamine, 13 g of 1-trimethylsilyl-1-propine, and 250 ml of N, N-dimethylformamide. Was charged, 1.5 g of tetrakistriphenylphosphine palladium was added as a catalyst at room temperature, and then the reaction vessel was heated to 70 ° C. and stirred for 7 hours. After allowing to cool, water and toluene were added to separate the liquids, toluene was added to the aqueous layer for extraction, and the combined organic layer was washed with water and saturated brine. After adding anhydrous sodium sulfate and drying, the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 18 g of the target compound represented by the following chemical formula.

18 g of the previously synthesized compound, 0.5 g of 5% palladium carbon and 60 ml of THF were added to the autoclave, and the mixture was stirred at 40 ° C. for 5 hours under a hydrogen pressure of 0.5 MPa. After the reaction, the filtrate was filtered through cellulose and washed with THF, and the filtrate was concentrated and purified by a silica gel column to obtain 16 g of the target compound represented by the following chemical formula.

16 g of 1-benzyloxy-2-propylbenzene and 100 ml of acetonitrile were charged in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 12.5 g of N-bromosuccinimide was added at 0 ° C., and the mixture was stirred at room temperature for 4 hours. .. The reaction mixture was concentrated under reduced pressure, hexane was added, and the precipitate was filtered. The filtrate was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to obtain 18 g of the target compound represented by the following chemical formula.

In a reaction vessel equipped with a stirrer, a cooler, and a dropping funnel, 17 g of 4-bromo-1-benzyloxy-2-propylbenzene, 60 ml of a 2 mol / l potassium carbonate aqueous solution, 0.8 g of tetrakistriphenylphosphine palladium, and 60 ml of ethanol were charged. , Stirred at 50 ° C. 20 ml of a THF solution of 9 g of 4-hydroxyphenylboronic acid was slowly added dropwise. The reaction was carried out at 50 ° C. for 6 hours. After completion of the reaction, the mixture is cooled, 100 ml of ethyl acetate is added, the organic layer is washed with water and saturated brine, the solvent is distilled off, purification with a silica gel column and crystallization with hexane are performed, and the mixture is represented by the following chemical formula. 13 g of the target compound was obtained.

To the autoclave, 12 g of the previously synthesized compound, 0.6 g of 5% palladium carbon and 80 ml of THF were added, and the mixture was stirred at 50 ° C. for 4 hours under a hydrogen pressure of 0.5 MPa. After the reaction, the filtrate was filtered through cellulose and washed with THF, and the filtrate was concentrated and purified by a silica gel column to obtain 11 g of the target compound represented by the following chemical formula.

Further, in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 10 g (43 mmol) of the previously synthesized compound, 7.7 g (90 mmol) of methacrylic acid, 0.2 g of dimethylaminopyridine and 100 ml of dichloromethane were charged, and ice was added. The reaction vessel was kept at 5 ° C. or lower in a cold bath, and 50 ml of THF in which 11.6 g (91 mmol) of diisopropylcarbodiimide was dissolved was slowly added dropwise. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 10 hours. After filtering the reaction solution, 100 ml of dichloromethane 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 performed by column chromatography using amino silica gel, and further dispersion washing with methanol was performed. After allowing to stand at −20 ° C., filtration and vacuum drying were carried out to obtain 11 g of the target compound represented by the formula (RM-7).

The physical property values ( ¹ H-NMR, ¹³ C-NMR and melting point) of the obtained compound are as follows. Physical characteristics: ¹ H-NMR (solvent: deuterated chloroform): δ7.70-7.58 (m, 4H), 7.34 (d, 1H), 7.18 (d, 2H), 6.55 (D, 2H), 6.15 (d, 2H), 2.46 (t, 2H), 2.18 (s, 6H), 1.66 (m, 2H), 0.96 ( t, 3H)
¹³ C-NMR (solvent: deuterated chloroform): δ166.2, 166.1, 150.2, 146.9, 138.0, 137.6, 136.0, 135.7, 132.5, 128.0 , 128.0, 127.8, 127.8, 122.1, 121.9, 121.8, 120.7, 120.6, 32.6, 24.1, 18.1, 18.0, 12 .8
Melting point: 119 ° C
(Synthesis Example 4)
"Method of synthesizing RM-18"
Under a nitrogen atmosphere, in a reaction vessel equipped with a stirrer, cooler and thermometer, 30 g of 1-benzyloxy-2,6-dibromobenzene, 10 g of triethylamine, 25 g of 1-trimethylsilyl-1-propine, and N, N-dimethyl. After charging 300 ml of formamide and adding 2 g of tetrakistriphenylphosphine palladium as a catalyst at room temperature, the reaction vessel was heated to 70 ° C. and stirred for 8 hours. After allowing to cool, water and toluene were added to separate the liquids, toluene was added to the aqueous layer for extraction, and the combined organic layer was washed with water and saturated brine. After adding anhydrous sodium sulfate and drying, the organic solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 20 g of the target compound.

20 g of the previously synthesized compound, 0.6 g of 5% palladium carbon and 100 ml of THF were added to the autoclave, and the mixture was stirred at 50 ° C. for 5 hours under a hydrogen pressure of 0.5 MPa. After the reaction, the filtrate was filtered through cellulose and washed with THF, and the filtrate was concentrated and purified by a silica gel column to obtain 18 g of the target compound represented by the following chemical formula.

16 g of 1-benzyloxy-2,6-dipropylbenzene and 100 ml of acetonitrile were charged in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 12 g of N-bromosuccinimide was added at 0 ° C., and the mixture was stirred at room temperature for 6 hours. did. The reaction mixture was concentrated under reduced pressure, hexane was added, and the precipitate was filtered. The filtrate was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to obtain 18 g of the target compound represented by the following chemical formula.

In a reaction vessel equipped with a stirrer, a cooler, and a dropping funnel, 16 g of 4-bromo-1-benzyloxy-3,5-dipropylbenzene, 60 ml of a 2 mol / l potassium carbonate aqueous solution, 1.0 g of tetrakistriphenylphosphine palladium, and ethanol. 50 ml was charged and stirred at 50 ° C. 30 ml of a THF solution of 12 g of 4-hydroxyphenylboronic acid was slowly added dropwise. The reaction was carried out at 60 ° C. for 10 hours. After completion of the reaction, the mixture is cooled, 100 ml of ethyl acetate is added, the organic layer is washed with water and saturated brine, the solvent is distilled off, purification with a silica gel column and crystallization with hexane are performed, and the mixture is represented by the following chemical formula. 12 g of the target compound was obtained.

11 g of the previously synthesized compound, 0.6 g of 5% palladium carbon and 50 ml of THF were added to the autoclave, and the mixture was stirred at 50 ° C. for 5 hours under a hydrogen pressure of 0.5 MPa. After the reaction, the filtrate was filtered through cellulose and washed with THF, and the filtrate was concentrated and purified by a silica gel column to obtain 7.5 g of the target compound represented by the following chemical formula.

Further, in a reaction vessel equipped with a stirrer, a cooler and a thermometer, 7 g (25 mmol) of the compound represented above, 4.7 g (54 mmol) of methacrylic acid, 0.2 g of dimethylaminopyridine and 100 ml of dichloromethane were charged. The reaction vessel was kept at 5 ° C. or lower in an ice-cooled bath, and 50 ml of THF in which 7 g (55 mmol) of diisopropylcarbodiimide was dissolved was slowly added dropwise. After completion of the dropping, the reaction vessel was returned to room temperature and reacted for 15 hours. After filtering the reaction solution, 100 ml of dichloromethane 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 performed by column chromatography using amino silica gel, and further dispersion washing with methanol was performed. After precipitation at −20 ° C., filtration and vacuum drying were carried out to obtain 8 g of the target compound represented by the following formula (RM-18).

The physical property values ( ¹ H-NMR, ¹³ C-NMR and melting point) of the obtained compound are as follows. Physical characteristics: ( ^{1 1} H-NMR (solvent: deuterated chloroform): δ7.64-7.54 (m, 4H), 7.26 (s, 2H), 6.75 (d, 2H), 6 .15 (dq, 2H), 2.48-2.46 (t, 4H), 2.23 (s, 6H), 1.64 (m, 4H), 0.96 (t, 6H)
¹³ C-NMR (solvent: deuterated chloroform): δ166.4, 166.0, 150.2, 146.8, 138.4, 137.6, 136.0, 135.8, 132.5, 132.5 , 128.0, 128.0, 127.8, 127.8, 122.1, 121.9, 120.7, 120.6, 32.8, 32.8, 24.3, 24.2, 17 9.9, 17.9, 12.8, 12.8
Melting point: 125 ° C
In the examples, the measured characteristics are as follows.

T _ni : Nematic phase-isotropic liquid phase transition temperature (° C)
Δn: Refractive index anisotropy at 20 ° C. η: Viscosity at 20 ° C. (mPa · s)
γ ₁ : Rotational viscosity at 20 ° C (mPa · s)
Δε: Dielectric constant anisotropy at 20 ° C K ₃₃ : Elastic modulus at 20 ° C K ₃₃ (pN)
<Ring structure>

<Side chain structure>

(However, n in the table is a natural number.)
<Connected structure>

(However, n in the table is a natural number.)
The evaluation of "low temperature storage", "vertical orientation", "pre-tilt angle formation" and "response characteristics" in this example and comparative example was performed by the following method.

(Evaluation test for low temperature storage)
The liquid crystal composition was filtered through a membrane filter (PTFE 13m-0.2μm manufactured by Agilent Technologies) and allowed to stand for 15 minutes under vacuum reduced pressure conditions to remove dissolved air. This was washed with acetone, weighed 0.5 g in a sufficiently dried vial, and allowed to stand in an environment of -25 ° C for 10 days. Then, the presence or absence of precipitation was visually observed, and the determination was made in the following two stages.

A: Precipitation cannot be confirmed.

B: Precipitate after 1 week.

D: Precipitation can be confirmed.

(Vertical orientation evaluation test)
It is driven by a first substrate (common electrode substrate) having a transparent electrode layer composed of transparent common electrodes patterned on an insulating layer and having no alignment film provided with a color filter layer, and an active element. A second substrate (pixel electrode substrate) having no alignment film having a pixel electrode layer having a transparent pixel electrode was prepared. The liquid crystal composition was dropped onto the first substrate, sandwiched on the second substrate, and the sealing material was cured at normal pressure at 110 ° C. for 2 hours to obtain a liquid crystal cell having a cell gap of 3.2 μm. At this time, the vertical orientation and the uneven orientation such as dripping marks were observed using a polarizing microscope and evaluated in the following four stages.

A: Uniform vertical alignment over the entire surface B: Level that is acceptable even if there is a slight alignment defect C: Level that is unacceptable due to alignment defect D: Orientation defect is considerably poor (evaluation test of pretilt angle formation)
The pretilt angle of the liquid crystal cell used in the above (evaluation test of vertical orientation) in the initial state was measured using OPTIPRO manufactured by Shintech.

(Evaluation test of response characteristics)
The cell with a cell gap of 3.2 μm used in the above (evaluation test for pretilt angle formation) was further irradiated with a UV fluorescent lamp manufactured by Toshiba Lighting & Technology Corporation for 60 minutes (illuminance 1.7 mW / cm ² at 313 nm). The response speed was measured for the cells thus obtained. The response speed was measured by Voff at 6 V under a temperature condition of 25 ° C. using DMS703 of AUTRONIC-MELCHERS.

(Preparation and evaluation results of liquid crystal composition)
A liquid crystal composition was prepared in a mixed ratio with the compound obtained in the above synthetic example or the compound as shown below, and the composition was designated as LC-1. The composition of the liquid crystal composition and the results of its physical property values are shown below.

LC-1 has a nematic phase-isotropic liquid phase transition temperature ( _TNI ) of 75 ° C, a solid phase-nematic phase transition temperature ( _TCN ) of -33 ° C, and a refractive index anisotropy (Δn) of 0.11. The dielectric anisotropy (Δε) was -2.8, and the rotational viscosity (γ ₁ ) was 98 mPa · s. The refractive index anisotropy (Δn), the dielectric anisotropy (Δε), and the rotational viscosity (γ1) are all measurement results at 25 ° C. (hereinafter, the same applies).

(Comparative Examples 1 to 4)
When LC-1 is 100 parts by mass, 1.0 part by mass of the following spontaneously oriented monomer (P-1) and 0.3 parts by mass of the compound represented by the formula (RM-R1) are added. A liquid crystal composition containing a sex compound was designated as Comparative Example 1.

Polymerization of the liquid crystal composition LC-1 by adding 1.0 part by mass of the spontaneously oriented monomer (P-1) and 0.3 part by mass of the compound represented by the formula (RM-R2) to 100 parts by mass. A liquid crystal composition containing a sex compound was designated as Comparative Example 2.

Polymerization of the liquid crystal composition LC-1 by adding 1.0 part by mass of the spontaneously oriented monomer (P-1) and 0.6 parts by mass of the compound represented by the formula (RM-R2) to 100 parts by mass. A liquid crystal composition containing a sex compound was designated as Comparative Example 3.

Polymerization of the liquid crystal composition LC-1 by adding 1.0 part by mass of the spontaneously oriented monomer (P-1) and 0.9 parts by mass of the compound represented by the formula (RM-R2) to 100 parts by mass. The liquid crystal composition containing a sex compound was designated as Comparative Example 4.

Table 2 shows the results of the vertical orientation test of the polymerizable compound after irradiation with ultraviolet rays of Comparative Examples 1 to 4.

(Examples 1 to 111)
Other than the addition of spontaneously oriented monomers (P-2) to (P-35) and polymerizable monomers (RM-1) to (RM-15) shown below to LC-1 in the amounts shown in Table 3 below, respectively. Prepared a liquid crystal composition in the same manner as in Comparative Example 1.

Regarding the low temperature storage stability of Examples 1 to 111, precipitation begins to occur in the polymerizable monomer having a long-chain alkyl group after about 1 week. In addition, the short-chain alkyl or alkoxy group-containing polymerizable compound had good solubility and good low-temperature storage stability. In addition, a cell in which a liquid crystal composition containing a vertical alignment aid and a polymerizable monomer was enclosed in the cell was set in a polarizing microscope in which a polarizing element and an analyzer were arranged orthogonally, and transmitted light was observed. If the liquid crystal molecules are vertically oriented, light cannot be transmitted due to the action of the polarizing plate, and the cells are displayed in black. When the above samples were evaluated by this test method, it was confirmed that all the samples showed no uneven orientation and showed uniform vertical orientation. The evaluation results of a typical orientation test are shown in FIGS. 1 and 2. FIG. 1 is a photograph of Comparative Example 2 and FIG. 2 is a photograph of a cell injected with a liquid crystal display of Example 40 under cross Nicol. The portion that looks white in the peripheral portion of the cell in FIG. 1 is not vertically oriented but diagonally or horizontally oriented, and shows uneven orientation. In FIG. 1, many white areas are seen, and many areas are not vertically oriented. Also, you can see a domain that looks like it is divided into four in the cell. This is dripping unevenness, which is an unevenness formed when the liquid crystal composition is dropped and spreads, and the compositions intersect with each other, and the liquid crystal composition is not uniformly mixed. This is also a kind of defect. However, in FIG. 2, almost no white line is seen, and black is uniformly shown. In FIGS. 1 and 2, the partially visible white straight line is not an uneven orientation but a physical scratch on the glass, and is not a poor orientation. Therefore, this indicates that the liquid crystal is vertically oriented on one side, and it is confirmed that the liquid crystal molecules are vertically oriented by appropriately combining the above-mentioned vertical alignment aid (spontaneous orientation monomer) and the polymerizable monomer. Was done.

Moreover, when the pre-tilt angle caused by the polymerization by ultraviolet light irradiation was evaluated, it was confirmed that an appropriate tilt angle was given to all the samples. It was confirmed that the liquid crystal display element using these has a sufficiently high-speed response because a sufficient pretilt angle is given.

Further, when the liquid crystal cell was produced from the composition containing RM-2 to RM-4 used as the polymerizable monomer in Examples 2 to 4, the expandability (wetting and spreading) was good.

(Examples 112 to 129)
The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-1) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 112 was a liquid crystal composition containing a polymerizable monomer to which 0.5 part by mass of the compound represented by RM-1) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-1) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 113 was a liquid crystal composition containing a polymerizable monomer to which 1.0 part by mass of the compound represented by RM-2) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-5) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 114 was a liquid crystal composition containing a polymerizable monomer to which 0.3 parts by mass of the compound represented by RM-3) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-5) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 115 was a liquid crystal composition containing a polymerizable monomer to which 0.6 parts by mass of the compound represented by RM-3) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-6) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 116 was a liquid crystal composition containing a polymerizable monomer to which 0.5 part by mass of the compound represented by RM-3) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-6) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 117 was a liquid crystal composition containing a polymerizable monomer to which 1.0 part by mass of the compound represented by RM-3) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-6) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 118 was a liquid crystal composition containing a polymerizable monomer to which 0.3 parts by mass of the compound represented by RM-4) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-6) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 119 was a liquid crystal composition containing a polymerizable monomer to which 0.6 parts by mass of the compound represented by RM-4) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-13) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 120 was a liquid crystal composition containing a polymerizable monomer to which 0.3 parts by mass of the compound represented by RM-7) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-13) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 121 was a liquid crystal composition containing a polymerizable monomer to which 0.6 parts by mass of the compound represented by RM-7) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-14) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 122 was a liquid crystal composition containing a polymerizable monomer to which 0.5 part by mass of the compound represented by RM-8) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-14) is 1.0 part by mass, the compound represented by the formula (RM-R2) is 0.3 part by mass and the formula ( Example 123 was a liquid crystal composition containing a polymerizable monomer to which 1.0 part by mass of the compound represented by RM-8) was added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-1) is 0.5 parts by mass, the spontaneously oriented monomer (P-5) is 1.0 part by mass, and the formula (RM-) is used. Example 124 was a liquid crystal composition containing a polymerizable monomer obtained by adding 0.3 parts by mass of the compound represented by R2) and 0.3 parts by mass of the compound represented by the formula (RM-4).

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-5) is 0.5 parts by mass, the spontaneously oriented monomer (P-6) is 1.2 parts by mass, and the formula (RM-) is used. Example 125 was a liquid crystal composition containing a polymerizable monomer in which 0.3 parts by mass of the compound represented by R2) and 1.0 part by mass of the compound represented by the formula (RM-3) were added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-5) is 1.0 part by mass, the spontaneously oriented monomer (P-8) is 0.5 part by mass, and the formula (RM-) is used. Example 126 was a liquid crystal composition containing a polymerizable monomer in which 0.3 parts by mass of the compound represented by R2) and 0.5 parts by mass of the compound represented by the formula (RM-4) were added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-5) is 0.8 parts by mass, the spontaneously oriented monomer (P-17) is 0.2 parts by mass, and the formula (RM-) is used. Example 127 was a liquid crystal composition containing a polymerizable monomer obtained by adding 0.3 parts by mass of the compound represented by R2) and 1.0 part by mass of the compound represented by the formula (RM-4).

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-6) is 1.2 parts by mass, the spontaneously oriented monomer (P-13) is 0.3 parts by mass, and the formula (RM-) is used. Example 128 was a liquid crystal composition containing a polymerizable monomer in which 0.3 parts by mass of the compound represented by R2) and 0.5 parts by mass of the compound represented by the formula (RM-3) were added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-6) is 1.0 part by mass, the spontaneously oriented monomer (P-19) is 0.5 part by mass, and the formula (RM-) is used. Example 129 was a liquid crystal composition containing a polymerizable monomer obtained by adding 0.3 parts by mass of the compound represented by R2) and 0.6 parts by mass of the compound represented by the formula (RM-3).

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-6) is 1.0 part by mass, the spontaneously oriented monomer (P-26) is 0.3 parts by mass, and the formula (RM-) is used. Example 130 was a liquid crystal composition containing a polymerizable monomer in which 0.3 parts by mass of the compound represented by R2) and 0.5 parts by mass of the compound represented by the formula (RM-4) were added.

The liquid crystal composition LC-1 is 100 parts by mass, the spontaneously oriented monomer (P-6) is 1.0 part by mass, the spontaneously oriented monomer (P-32) is 0.5 part by mass, and the formula (RM-) is used. Example 131 was a liquid crystal composition containing a polymerizable monomer obtained by adding 0.3 parts by mass of the compound represented by R2) and 0.3 parts by mass of the compound represented by the formula (RM-4).

In Examples 112 to 123, when one kind of spontaneous orientation aid and two kinds of polymerizable compounds (or polymerizable monomers) were used, the low temperature storage stability and vertical orientation were evaluated, and the polymerization used in the comparative example was evaluated. It was confirmed that even if a sex compound was used, the low temperature storage property and the vertical orientation were improved by adding a new polymerizable compound. When the solubility of the spontaneously oriented monomer in the liquid crystal display is low, the concentration of one component can be lowered, and a different spontaneously oriented monomer can be added to improve the vertical orientation. It was confirmed that the low temperature storage stability and the vertical orientation were improved by mixing two kinds of spontaneously oriented monomers and two kinds of polymerizable compounds in Examples 124 to 131.

Further, when the liquid crystal cell was produced from the composition containing RM-2 to RM-4 used as the polymerizable monomer in Examples 113 to 118 and the like, the expandability (wetting and spreading) was good.

(Examples 132 to 140)
Further, instead of the composition LC-1, a composition composed of the compounds and a mixing ratio as shown below was prepared, and the prepared liquid crystal composition was changed from LC-2 to LC-8.

Spontaneous orientation monomers (P-5, P-6, PJ-23, PK-5, PK-6, P-28 or P-35) and the polymerizable monomer (RM-2, RM-3 or RM-4) were mixed at an appropriate concentration, and the orientation test was evaluated in the same manner as above. It was confirmed that the sex was improved.

Claims (11)

General formula (I):

(In the above general formula (I),
R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁸ , R ¹⁰⁹ and R ¹¹⁰ are independently P ¹¹ -S ^11- and have 1 to 18 carbon atoms. Represents an alkyl group, an alkoxy group having 1 to 18 carbon atoms, a halogen atom or a hydrogen atom.
P ¹¹ represents a methacrylic acid group and represents
S ¹¹ represents a single bond or an alkylene group having 1 to 15 carbon atoms.
One or more -CH _2- in the alkylene group may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other.
n ¹¹ represents 0 or 1 and represents
A ¹¹ is the following group (a), group (b) and group (c):
(A) 1,4-Cyclohexylene group (one -CH _2- or two or more non-adjacent -CH ₂ -existing in this group may be replaced with -O-).
(B) 1,4-Phenylene group (one -CH = existing in this group or two or more non-adjacent -CH = 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-A single -CH = present in a diyl group or two or more non-adjacent -CH = may be replaced with -N =).
Represents a group selected from the group consisting of
The above groups (a), groups (b) and groups (c) are independently alkyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 12 carbon atoms, halogens, cyano groups and nitro groups. Alternatively, it may be replaced with P ¹¹ -S ^11- .
L ¹⁰ and L ¹¹ are independently single-bonded, -OCH _2- , -CH ₂ O-, -C ₂ H _4- , -OC ₂ H ₄ O-, -COO-, -OCO-,-, respectively. CH = CR ^a -COO-, -CH = CR ^a -OCO-, -COO-CR ^a = CH-, -OCO-CR ^a = CH-,-(CH ₂ ) _z -COO-,-(CH ₂ ) _z -OCO-, -OCO- (CH ₂ ) _z- , -COO- (CH ₂ ) _z- , -CH = CH-, -CF ₂ O-, -OCF _2- or -C≡C- (in the formula) , Ra independently represent ^a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and z in the above formula independently represent an integer of 1 to 4).
It has at least two or more P ¹¹ -S ¹¹ -in one molecule of the above general formula (I), and has.
It has an alkyl group having 1 to 18 carbon atoms in one molecule of the above general formula (I).
One or two or more non-adjacent _—CH2- in the alkyl group may be independently substituted with —O—.
When a plurality of P ¹¹ , S ¹¹ , L ¹¹ and A ¹¹ exist, they may be the same or different from each other. )
The polymerizable monomer represented by
It has a chemical structure different from that of the polymerizable monomer represented by the general formula (I), and contains at least one polar group , a mesogen group, and a spontaneously oriented monomer having at least one polymerizable group. ,
The polar group has the following formula (K-1-1).
A liquid crystal composition in which the mesogen group is represented by the following formula (me-1) .
・ Polar group

(In the above formula (K-1-1),
W ^K1 represents a methine group or ≡C-CH ₃ . )
・ Mesogen group

(In the formula (me-1),
The hydrogen atom in the 1,4-phenylene group may be substituted with a methyl group, an ethyl group, a halogen atom, or P11-S11- ^, and the ^polar group.
P ¹¹ represents a methacrylic acid group and represents
S ¹¹ represents a single bond or an alkylene group having 1 to 15 carbon atoms.
One or more -CH _2- in the alkylene group may be substituted with -O-, -OCO- or -COO- so that oxygen atoms are not directly adjacent to each other.
The leftmost black dot and the rightmost black dot represent a bond. ) The liquid crystal composition according to claim 1, wherein the polar group and the polymerization group in the spontaneously oriented monomer are adjacent to each other. The liquid crystal composition according to claim 1 or 2 , wherein each of the compounds represented by the general formula (I) has the same or different two P ¹¹ -S ¹¹ -in one molecule. The liquid crystal composition according to any one of claims 1 to 3 , wherein L ¹⁰ and L ¹¹ are single bonds in the general formula (I). General formulas (N-1), (N-2) and (N-3)

(During the ceremony,
^RN11 , ^RN12 , ^RN21 , ^RN22 , ^RN31 and ^RN32 each independently represent an alkyl group having 1 to 8 carbon atoms.
One or two or more non-adjacent -CH _2- in the alkyl group are independently -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO. May be replaced by-
^{AN11, AN12, AN21, AN22, AN31 and AN32 are independently ( a )} 1,4-cyclohexylene groups (one -CH _2- or adjacent to each other present in this group). Two or more -CH _2- that are not used 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 = present 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.
The above groups (a), group (b), group (c) and group (d) may be independently substituted with a cyano group, a fluorine atom or a chlorine atom, respectively.
Z ^N11 , Z ^N12 , Z ^N21 , Z ^N22 , Z ^N31 and Z ^N32 are independently single-bonded, -CH ₂ CH ₂ -,-(CH ₂ ) _4- , -OCH _2- , -CH ₂ respectively. 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 an oxygen atom and represents
Although n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3,
n ^N11 + n ^N12 , n ^N21 + n ^N22 and n ^N31 + n ^N32 are independently 1, 2 or 3, respectively.
When there are a plurality of ^{AN11 to AN32 and Z N11 to Z N32 , they} may be the same or different. )
The liquid crystal composition according to any one of claims 1 to 4 , which contains one kind or two or more kinds of compounds selected from the compounds represented by. General formula (L)

(During the ceremony,
^RL1 and ^RL2 each independently represent an alkyl group having 1 to 8 carbon atoms.
One or two or more non-adjacent -CH _2- in the alkyl group are independently -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO. May be replaced by-
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 non-adjacent-CH ₂ ). -May be replaced with -O-.)
(B) 1,4-Phenylene group (one -CH = existing in this group or two or more non-adjacent -CH = 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-A single -CH = present in a diyl group or two or more non-adjacent -CH = may be replaced with -N =).
Represents 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, respectively.
Z ^L1 and Z ^L2 are independently single-bonded, -CH ₂ CH ₂ -,-(CH ₂ ) _4- , -OCH _2- , -CH ₂ O-, -COO-, -OCO-,-. It represents OCF _2- , -CF ₂ O-, -CH = NN = CH-, -CH = CH-, -CF = CF- or -C≡C-.
When n ^L1 is 2 or 3 and there are a plurality of A ^L2 , they may be the same or different.
When n ^L1 is 2 or 3 and there are a plurality of Z ^L2s , they may be the same or different.
The compounds represented by the general formula (N-1), the general formula (N-2) and the general formula (N-3) are excluded. )
The liquid crystal composition according to any one of claims 1 to 5 , which contains one kind or two or more kinds of compounds selected from the compounds represented by. The liquid crystal composition according to any one of claims 1 to 6 , which is used for a liquid crystal display element having no alignment film on the surface of at least one of the pair of substrates. A liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 7 . A liquid crystal display element for driving an active matrix using the liquid crystal composition according to any one of claims 1 to 7 . A liquid crystal display element for PSA mode, PSVA mode, PS-IPS mode, or PS-FSS mode using the liquid crystal composition according to any one of claims 1 to 7 . The first board and the second board arranged opposite to each other,
A liquid crystal layer filled between the first substrate and the second substrate,
A plurality of gate bus lines and data bus lines arranged in a matrix on the first substrate, a thin film transistor provided at an intersection of the gate bus line and the data bus line, and a pixel electrode driven by the thin film transistor. With an electrode layer that has each pixel
With a common electrode formed on the first substrate or the second substrate,
The liquid crystal layer is composed of the liquid crystal composition according to any one of claims 1 to 7 .
A liquid crystal display element that does not have an alignment film on the surface of at least one of the substrates.

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