JP2020002065A - Polymerizable compound and liquid crystal composition and liquid crystal element using the same - Google Patents

Abstract

To provide a compound that ensures storage property when added to a liquid crystal composition and allows vertical alignment of liquid crystal molecules without disposing a PI layer.SOLUTION: A compound represented by formula (i) is provided, which includes two partial structures Krepresented by general formulae (K-1) to (K-17) and at least one P-Sp-. When the compound is used for a liquid crystal composition, the compound adsorbs to substrates interposing the liquid crystal composition (a liquid crystal layer) and can hold liquid crystal molecules as aligned in a perpendicular direction, and ensures higher stability of aligning property and solubility with a liquid crystal.SELECTED DRAWING: None

Description

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

  2. Description of the Related Art Conventionally, in a VA (Vertical Alignment) type liquid crystal display, a polyimide alignment film (PI) layer is formed on an electrode to induce vertical alignment of liquid crystal molecules when no voltage is applied and to realize horizontal alignment of liquid crystal molecules when a voltage is applied. Is provided. However, since a large cost is required for forming the PI layer, a method for realizing alignment of liquid crystal molecules while omitting the PI layer has been studied in recent years.

  For example, Patent Documents 1 and 2 disclose a liquid crystal medium characterized by containing at least one kind of spontaneous alignment compound, and this liquid crystal medium is highly suitable for use in a display containing no alignment layer. Is described. In Patent Literature 1 and Patent Literature 2, a specific compound having a hydroxyl group is used as a spontaneous alignment compound.

International Publication No. 2017/209161 JP-T-2016-501938

  However, according to studies by the present inventors, when the self-aligning compounds described in Patent Documents 1 and 2 are used, electro-optical properties such as alignment regulating force and alignment stability for vertically aligning liquid crystal molecules are obtained. However, it was found that there was still room for improvement in the solubility of the spontaneous alignment compound in the liquid crystal composition.

  Therefore, an object of the present invention is to have a polar structure-containing group capable of ensuring the solubility when added to a liquid crystal composition and enabling the alignment of liquid crystal molecules without providing a PI layer, and further having a polymerizable functional group. An object of the present invention is to provide a spontaneous alignment compound having excellent alignment stability by having a group. Another object of the present invention is to provide a liquid crystal composition having excellent solubility and capable of vertically aligning liquid crystal molecules without providing a PI layer, and a liquid crystal display device using the liquid crystal composition. .

  The present invention provides a compound represented by the general formula (i).

(Where
MES represents a mesogen group having one or more ring structures,
Z ⁱ¹ represents a (n ⁱ¹ +1) ^-valent organic group or a single bond;
Z ⁱ² represents a (n ⁱ² +1) ^-valent organic group or a single bond, wherein Z ⁱ¹ and Z ⁱ² are bonded on the same ring in the MES;
^Ki1 and ^Ki2 each independently represent a polar structure-containing group;
n ⁱ¹ and n ⁱ² each independently represent an integer from 1 to 3,
Here, MES, Z ^i1, Z ^i2, at least one or more groups selected from K ⁱ¹ and K ⁱ² is 1 or more P ⁱ¹ -Sp ⁱ¹ - is substituted with, here P ⁱ¹ polymerization functional group And Sp ⁱ¹ represents a single bond or a divalent linking group,
If K ^i1, K ^i2, P ⁱ¹ or Sp ⁱ¹ is more present in the formula, it may be be the same or different. )
The present invention also provides a liquid crystal composition containing one or more compounds having a partial structure represented by the general formula (i).

  According to the present invention, a spontaneous alignment compound, a liquid crystal composition, and a liquid crystal composition, which have excellent solubility, enable uniform vertical alignment of liquid crystal molecules without providing a PI layer, and have a stable tilt angle and high reliability A liquid crystal display device using the composition can be provided.

  The spontaneous alignment compound of the present embodiment is a compound represented by the general formula (i).

The compound represented by the general formula (i) has a mesogen group MES in the structure, and has at least two polar structure-containing groups ^Ki1 and ^Ki2 . Therefore, when used in a liquid crystal composition, the polar structure-containing group and the substrate sandwiching the liquid crystal composition (liquid crystal layer) interact and adhere to each other, and the mesogen group rises vertically from the substrate. Therefore, the liquid crystal molecules can be held in a state of being aligned in the vertical direction. Therefore, according to the liquid crystal composition using the spontaneous alignment compound of this embodiment, the liquid crystal molecules are aligned without providing the PI layer (the liquid crystal molecules are vertically aligned when no voltage is applied, and the liquid crystal molecules are aligned when the voltage is applied). Is realized). In addition, the present inventors have found that since the compound represented by the general formula (i) has a polymerizable functional group on its structure, the compound is polymerized after liquid crystal alignment, so that the alignment state once achieved can be achieved. It has been found that stable maintenance can be achieved. As described above, the compound represented by the general formula (i) is suitably used for assisting vertical alignment of liquid crystal molecules in a liquid crystal composition.

<Spontaneous alignment compound>
The spontaneous alignment compound according to the present invention is mainly used by being added to a liquid crystal composition, and a member (an electrode (for example, ITO), a substrate (for example, a glass substrate, an acrylic resin, etc.) which directly contacts a liquid crystal layer containing the liquid crystal composition. Substrate, a transparent substrate, a flexible substrate, etc.), a resin layer (eg, a color filter, an alignment film, an overcoat layer, etc.), an insulating film (eg, an inorganic material film, SiNx, etc.), and a liquid crystal layer. It has a function of inducing homeotropic alignment or homogeneous alignment of liquid crystal molecules.

Spontaneous alignment compound represented by Formula (i), P ⁱ¹ -Sp ⁱ¹ as a polymerizable group for polymerizing - and groups represented by the mesogenic group MES similar to liquid crystal molecules, direct a liquid crystal layer It has two or more polar structure-containing groups represented by K ⁱ¹ and K ⁱ² that can interact with the contacting member.

  Hereinafter, * at the left end and * at the right end in the chemical formula represent a bond.

`` Polymerizable group ''
P ⁱ¹ -Sp ⁱ¹ in the general formula (i) - polymerizable group represented ^by, P ^{AP1 -Sp} AP1 - is preferably represented by.

P ^AP1 is preferably a group selected from the group represented by the following general formulas (AP-1) to (AP-9).

(Wherein, R ^AP1 and R ^AP2 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 10 carbon atoms, and one of the alkyl groups or Two or more —CH ₂ — may be substituted with —O— or —CO—, and one or more hydrogen atoms in the alkyl group are each independently substituted with a halogen atom or a hydroxyl group. W ^AP1 represents a single bond, —O—, —COO— or —CH ₂ —, and t ^AP1 represents 0, 1, or 2.)
P ^AP1 is preferably a group represented by general formulas (AP-1) to (AP-7), and a group represented by general formula (AP-1) or (AP-2). And preferably represented by the general formula (AP-1).

Sp ^AP1 preferably represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, and represents a single bond or a linear alkylene group having 1 to 20 carbon atoms. And more preferably a single bond or a linear alkylene group having 2 to 10 carbon atoms. In Sp ^AP1 , one or two or more non-adjacent —CH ₂ — in the alkylene group are each independently —CH ＝ CH—, —C≡C—, —O—, —CO -, -COO- or -OCO- may be substituted.

In spontaneous orientation compounds according to the present invention, the polymerizable group ^{(P AP1 -Sp} AP1 -) number of, preferably 1 to 5 or less, more preferably 1 to 4, 2 to 4 Is more preferably 2 or 3, more preferably 2.

A hydrogen atom in P ^AP1 —Sp ^AP1 — may be substituted with a polymerizable group and / or a polar structure-containing group.

Further, the spontaneous alignment compound according to the present invention, the polymerizable group (P ^{AP1 -Sp AP1 -)} is preferred over the binding to the mesogenic group or polar structure-containing group.

Incidentally, P ^AP1 and / or Sp ^AP1 in the molecule ^- when there are a plurality, may each also being the same or different.

"Mesogen group (MES)"
MES in the general formula (i) represents a mesogen group having one or more ring structures, and is preferably composed of a skeleton having one or more ring structures and an orientation inducing group bonded to the ring structures. The mesogen group refers to a group having a rigid portion, for example, a group having one or more cyclic groups, preferably having 2 to 4 cyclic groups, and having 3 to 4 cyclic groups. More preferably, the cyclic group may be linked by a linking group, if necessary. The mesogen group preferably has a skeleton similar to the liquid crystal compound used for the liquid crystal layer.

  In the present specification, “cyclic group” refers to an atomic group in which constituent atoms are cyclically bonded, and includes a carbocyclic ring, a heterocyclic ring, a saturated or unsaturated cyclic structure, a monocyclic structure, a bicyclic structure, and a polycyclic structure. Formulas include aromatic, non-aromatic, and the like. Further, the cyclic group may contain at least one hetero atom, and may be further substituted with at least one substituent (halogeno group, polymerizable group, organic group (alkyl, alkoxy, aryl, etc.)). When the formula group has a single ring, the mesogen group preferably contains two or more single rings.

  The MES in the general formula (i) is preferably represented, for example, by the general formula (AL).

^{(Wherein, Z AL1} is a single bond, -CH = CH -, - CF = CF -, - C≡C -, - COO -, - OCO -, - OCOO -, - 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 1 to 20 carbon atoms. one or not adjacent two or more -CH ₂ - is -O -, - COO- or -OCO- may be substituted with,
A ^AL1 represents a divalent cyclic group,
A ^AL2 represents a trivalent cyclic group,
Z ^{AL1, A AL1} and one or more hydrogen atoms in ^{A AL2} are each independently, a halogeno group, the polar structure-containing ^group, P al ^{-Sp al} - optionally substituted with or a monovalent organic group Well,
When a plurality of ^ZAL1 and ^AAL1 are present in a molecule, they may be the same or different from each other,
m ^AL1 represents an integer of 1 to 5. )
In the general formula (AL), Z ^AL1 is preferably a single bond or an alkylene group having 2 to 20 carbon atoms, more preferably a single bond or an alkylene group having 2 to 10 carbon atoms, and a single bond,-(CH ₂ ) ₂ - or - _{(CH 2) 4} - are preferred. One or two or more non-adjacent —CH ₂ — in the alkylene group may be substituted with —O—, —COO—, or —OCO—. Furthermore, when the linearity of the rod-shaped molecule is intended, a single bond in which rings are directly connected to each other or an even number of atoms directly connecting rings to each other is preferable. For _example, in the case of -CH ₂ -CH 2 COO-, the number of atoms connecting the ring and the ring directly is four.

In the general formula (AL), A ^AL1 represents a divalent cyclic group, and examples of the divalent cyclic group include a 1,4-phenylene group, a 1,4-cyclohexylene group, and a 1,4-cyclohexenyl. Group, tetrahydropyran-2,5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydrothiopyran-2,5-diyl group, thiophene-2,5-diyl group, 1,4-bicyclo (2,2,2) octylene group, decahydronaphthalene-2,6-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, thiophene- 2,5-diyl group-, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 2,6-naphthylene group, phenanthrene-2,7-diyl group, 9,10-dihydrophenanthrene-2 , 7-diyl group, 1,2,3,4,4a, 9,10a-octahydrophenanthrene-2,7-diyl group, 1,4-naphthylene group, benzo [1,2-b: 4,5-b '] dithiophene-2 , 6-diyl group, benzo [1,2-b: 4,5-b ′] diselenophen-2,6-diyl group, [1] benzothieno [3,2-b] thiophene-2,7-diyl group, [1] It preferably represents one type of structure selected from the group consisting of a benzoselenopheno [3,2-b] selenophene-2,7-diyl group and a fluorene-2,7-diyl group, and these structures are preferred. May be unsubstituted or substituted, more preferably 1,4-phenylene group, 1,4-cyclohexylene group, 2,6-naphthylene group or phenanthrene-2,7-diyl group, and 1,4-phenylene Group or 1,4-cyclohexyl Group is preferred. As the substituent, a fluorine atom or an alkyl group having 1 to 8 carbon atoms is preferable, and the alkyl group may be substituted with a fluorine atom or a hydroxyl group.

In the general formula (AL), ^AAL2 represents a trivalent cyclic group. As the trivalent cyclic group, 1,3,4-phenylene group, 1,3,5-phenylene group, 1,3 1,4-cyclohexylene group, 1,3,5-cyclohexylene group, 1,3,4-cyclohexenyl group, 1,3,5-cyclohexenyl group, tetrahydropyran-2,4,5-toluyl group, tetrahydro Pyran-2,4,6-toluyl group, tetrahydrothiopyran-2,4,5-toluyl group, tetrahydrothiopyran-2,4,6-toluyl group, decahydronaphthalene-2,5,6-toluyl group, Decahydronaphthalene-2,5,7-toluyl group, decahydronaphthalene-2,6,7-toluyl group, pyridine-2,4,6-toluyl group, pyridine-2,4,5-toluyl group, 2, 5,6-naphthylene group, 2,5,7-naphthylene And preferably represents one kind of structure selected from the group consisting of 2,6,7-naphthylene group, and these structures may be unsubstituted or substituted, and include 1,3,4-phenylene group, , 3,5-phenylene group, 1,3,4-cyclohexylene group, 1,3,5-cyclohexylene group, 1,3,4-cyclohexenyl group, 1,3,5-cyclohexenyl group, 2, A 5,6-naphthylene group, a 2,5,7-naphthylene group and a 2,6,7-naphthylene group are more preferred, and a 1,3,4-phenylene group or a 1,3,5-phenylene group is preferred. As the substituent, a fluorine atom or an alkyl group having 1 to 8 carbon atoms is preferable, and the alkyl group may be substituted with a fluorine atom or a hydroxyl group.

Also, one or more hydrogen atoms are halogeno groups in the cyclic group, the polar structure-containing group, P ^{AL1 -Sp} AL1 ^- or which may be substituted with a monovalent organic group.

In the general formula (AL), the monovalent organic group is a group having a chemical structure formed by converting an organic compound into a monovalent group, and is obtained by removing one hydrogen atom from the organic compound. Means an atomic group, for example, an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkenyloxy group having 2 to 15 carbon atoms, etc. And an alkyl group having 1 to 15 carbon atoms or an alkoxy group having 1 to 14 carbon atoms is preferable. An alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms is preferable. Preferred is an alkyl group having 5 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 2 carbon atoms, and an alkyl group having 1 or 2 carbon atoms or Charcoal Alkoxy groups having the number of atoms of 1 is preferable. One or two or more non-adjacent —CH ₂ — in the above-mentioned alkyl group, alkenyl group, alkoxy group and alkenyloxy group may be substituted with —O—, —COO— or —OCO—. Further, the monovalent organic group may have a role as an orientation inducing group described later.

In the general formula (AL), m ^AL1 is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, and preferably 2 or 3.

Preferable forms of the skeleton having one or more ring structures, that is, the structural part in which A ^AL1 , Z ^AL1 and A ^{AL2 in} the general formula (AL) are linked are represented by the following formulas (me-1) to (me) -44).

(The general formula (AL) is a structure in which three hydrogen atoms in these structures are eliminated.)
These formulas (me-1) ~ (me -44) in the cyclohexane ring, one of the hydrogen atoms of the benzene ring or a naphthalene ring or two or more independently halogeno ^group, P AP1 ^{-Sp AP1} -, It may be substituted by a monovalent organic group (for example, an alkyl group having 1 to 15 carbon atoms or an alkoxy group having 1 to 14 carbon atoms) or a polar structure-containing group. )
Preferred forms of the mesogen groups are formulas (me-8) to (me-44), and more preferably formulas (me-8) to (me-10) and formulas (me-12) to (me-12). -18), Formulas (me-22) to (me-24), Formulas (me-26) to (me-27), and Formulas (me-29) to (me-44), and more preferably the formula (Me-12), (me-15) to (me-16), (me-22) to (me-24), (me-29), (me-34), (me-36) to (me) -37) and (me-42) to (me-44).

The orientation inducing group R ^AK1 in the general formula (AL) represents a linear or branched alkyl group having 1 to 20 carbon atoms, and one or two or more —CH ₂ — in the alkyl group are The oxygen atoms may be independently substituted without being directly bonded to each other by -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, One or more hydrogen atoms in the alkyl group may be independently substituted with a halogeno group.

R ^AK1 preferably represents a linear or branched alkyl group having 1 to 20 carbon atoms, more preferably a linear alkyl group having 1 to 20 carbon atoms, More preferably, it represents an alkyl group having 1 to 8 carbon atoms. Also, one or non-adjacent two or more -CH ₂ in the alkyl group - are each independently, -CH = CH -, - C≡C -, - O -, - CO -, - It may be substituted by COO- or -OCO-. A hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom, or may be substituted with a fluorine atom. )
A particularly preferred embodiment of the mesogen group is represented by the following formula (AL-1) or (AL-2), and the formula (AL-1) is more preferred.

(In the ^{formula, X AL102 ~X AL118, X AL201} ~X AL214 are each independently a hydrogen atom, a halogeno group, an alkyl group, an alkoxy group, an alkenyl ^group, P APL ^{-Sp APL} - represents or polar structure-containing group , ring a ^AL11, a ^AL12 and ring a ^AL21 each independently represent cyclohexane ring or benzene ring,
Any two or more of X ^{AL102 to} X ^AL118 and X ^{AL201 to} X ^AL214 are substituted with a group containing a polar structure-containing group,
Polar structure-containing group ^P AP1 ^{-Sp AP1} - may be substituted with,
Compounds having formula (AL-1) or general formula (AL-2) as mesogenic group (i) are ^P AP1l ^{-Sp APl} in its molecule - has one or more. )
In formula (AL-1), R ^AK1 is preferably an alkyl group, an alkoxy group, or an alkenyl group.

In the general formula (AL-1), at least two of ^XAL109 , ^XAL110, and ^XAL111 are preferably groups containing a polar structure-containing group, and both ^XAL109 and ^XAL110 are groups containing a polar structure-containing group. It is preferable that both ^XAL109 and ^XAL111 are groups containing a polar structure-containing group.

In formula ^(AL-1), at least one of ^{X AL106,} X ^AL107 and ^{X AL108} is ^P AP1 ^{-Sp AP1} - or is, preferably has a polymerizable possible sites within the structure of the polar structure-containing group , both or one of ^{X AL106} and ^{X AL107} is ^P AP1 ^{-Sp AP1} - is preferably.

In the general formula (AL-1), one or two of X ^{AL104 to} X ^AL108 and X ^{AL112 to} X ^AL116 are each independently an alkyl group having 1 to 5 carbon atoms and an alkoxy group having 1 to 5 carbon atoms. Or a halogeno group, preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom, and X ^AL113 , X ^AL114 or X ^AL115 is an alkyl group having 1 to 3 carbon atoms or a fluorine atom. Preferably, there is.

In Formula (AL-2), R ^AK1 is preferably an alkyl group, an alkoxy group, or an alkenyl group.

In the general formula (AL-2), at least two of ^XAL207 , ^XAL208, and ^XAL209 are preferably groups containing a polar structure-containing group, and both ^XAL207 and ^XAL208 are groups containing a polar structure-containing group. It is ^preferable that both ^XAL207 and ^XAL209 are groups containing a polar structure-containing group.

In formula ^(AL-2), at least one of ^{X AL204,} X ^AL205 and ^{X AL206} is ^P AP1 ^{-Sp AP1} - or is, preferably has a polymerizable possible sites within the structure of the polar structure-containing group , both or one of ^{X AL204} and ^{X AL205} is ^P AP1 ^{-Sp AP1} - is preferably.

In the general formula (AL-2), one or two of X ^{AL202 to} X ^AL206 and X ^{AL210 to} X ^AL214 are each independently an alkyl group having 1 to 5 carbon atoms and an alkoxy group having 1 to 5 carbon atoms. Or a halogeno group, preferably an alkyl group having 1 to 3 carbon atoms or a fluorine atom, and X ^AL210 , X ^AL211 or X ^AL212 is an alkyl group having 1 to 3 carbon atoms or a fluorine atom. Preferably, there is.

`` Polar structure-containing group ''
The polar structure-containing groups represented by K ⁱ¹ and K ⁱ² in the general formula (i) are groups having a role of adsorbing an adsorbent such as a substrate, a film, or an electrode, which is a layer in contact with the liquid crystal composition. Adsorption is generally classified into chemisorption in which a chemical bond (covalent bond, ionic bond, or metal bond) is created to adsorb between the adsorbent and the adsorbate, or physical adsorption other than the chemisorption. The book may be adsorbed by chemical adsorption or physical adsorption, but is preferably adsorbed to the adsorbent by physical adsorption. Therefore, the polar structure-containing group according to the present invention is preferably a group that can physically adsorb to the adsorbent, and it is more preferable that the polar structure-containing group be bonded to the adsorbent by an intermolecular force. Examples of the mode of binding to the adsorbent by the intermolecular force include a bond to the adsorbent by an interaction such as permanent dipole, permanent quadrupole, dispersion force, charge transfer force, or hydrogen bond. Preferred examples of the polar structure-containing group according to the present invention include a form capable of bonding to an adsorbent by hydrogen bonding. In this case, the polar structure-containing group according to the present invention may serve as a donor or an acceptor of a proton via a hydrogen bond, or may serve as both.

  The polar structure-containing group according to the present invention is a group including a polar element having an atomic group in which a carbon atom and a hetero atom are linked. As used herein, the term “polar element” refers to an atomic group in which a carbon atom and a hetero atom are directly connected. The hetero atom is preferably at least one selected from the group consisting of N, O, S, P, B and Si, and is at least one selected from the group consisting of N, O and S. Is preferably at least one selected from the group consisting of N and O, and O is preferable.

  Further, in the spontaneous alignment compound according to the present invention, the valence of the polar element according to the present invention is not particularly limited to monovalent, divalent, trivalent, and the number of polar elements in the polar structure-containing group is also particularly limited. There is no restriction.

  In the spontaneous alignment compound according to the present invention, the number of the polar structure-containing group is preferably 2 to 6, more preferably 2 to 4, and further preferably 4 in one molecule.

The polarity structure-containing group of the present invention, excluding the polymerizable group, a hydrogen atom in a polar structure-containing group ^P AP1 ^{-Sp AP1} - substituted structures and ^P AP1 ^{-Sp AP1} - hydrogen atoms in Is a polar structure-containing group.

  The polar structure-containing group according to the present invention contains one or more polar elements, and the polar structure-containing group is roughly classified into a cyclic base type and a chain base type. The cyclic base type is a form including a cyclic group having a cyclic structure including a polar element in its structure, and the chain base form includes a cyclic group having a cyclic structure including a polar element in its structure. There is no form. The chain group is a form having a polar element in a linear or branched chain group, and a part thereof may have a cyclic structure containing no polar element.

  The form in which the polar structure-containing group according to the present invention contains a cyclic group means a form in which at least one polar element is included in a cyclic atomic arrangement. In addition, the cyclic group in this specification is as described above. Therefore, in the case where the polar structure-containing group according to the present invention has a form containing a cyclic group, the polar structure-containing group may contain even a cyclic group containing a polar element. There may be.

  The form in which the polar structure-containing group according to the present invention is a chain type group means that there is no cyclic atomic arrangement containing a polar element in the molecule, and at least one polar element is a linear atomic arrangement (may be branched). Means the form contained within. In addition, a chain group in the present specification refers to an atomic group in which the constituent atoms have no cyclic atomic arrangement in a structural formula and are constituted by linearly (may be branched) atoms, and refers to an acyclic group. . In other words, it refers to a linear or branched aliphatic group, which may contain either a saturated or unsaturated bond, for example, including alkyl, alkenyl, alkoxy, ester, ether or ketone, and at least one of A substituent may be substituted by a reactive functional group (such as a vinyl group, an acryl group, or a methacryl group) or a chain organic group (such as an alkyl group or a cyano group). It may be either a chain or a branch.

  When the polar structure-containing group according to the present invention is a cyclic group, a heteroaromatic group having 3 to 20 carbon atoms (including a condensed ring) or a heteroaliphatic group having 3 to 20 carbon atoms (including a condensed ring) Is more preferable, and a heteroaromatic group having 3 to 12 carbon atoms (including a condensed ring) or a heteroaliphatic group having 3 to 12 carbon atoms (including a condensed ring) is still more preferable, and 5-membered It is even more preferable to represent a ring heteroaromatic group, a 5-membered heteroaliphatic group, a 6-membered heteroaromatic group or a 6-membered heteroaliphatic group, and a hydrogen atom in these ring structures is a halogeno group, a carbon atom It may be substituted by a linear or branched alkyl group or alkyloxy group having 1 to 5 atoms.

If polar structure-containing group of the present invention is a chain groups, straight-chain or branched having 1 to 20 carbon atoms or hydrogen atoms in the alkyl group and -CH 2 _- that is substituted with a polar component Is preferably one or two or more non-adjacent —CH ₂ — in the alkyl group is —CH ＝ CH—, —C≡C—, —O—, —CO—, —COO— or — It may be substituted by OCO-. Further, when the polar structure-containing group according to the present invention is a chain-type group, it is preferable that a polar element is contained at the end or two or more polar elements are contained.

  The hydrogen atom of the polar structure-containing group according to the present invention may be substituted with a polymerizable group.

  The types of the polar element according to the present invention include, specifically, a polar element containing an oxygen atom (hereinafter referred to as an oxygen-containing polar element), a polar element containing a nitrogen atom (hereinafter referred to as a nitrogen-containing polar element), and a polarity containing a phosphorus atom. Element (hereinafter referred to as a phosphorus-containing polar element), a polar element containing a boron atom (hereinafter referred to as a boron-containing polar element), a polar element containing a silicon atom (hereinafter referred to as a silicon-containing polar element), or a polar element containing a sulfur atom (hereinafter referred to as a polar element). (Sulfur polar element), from the viewpoint of adsorption ability, a nitrogen-containing polar element, a nitrogen-containing polar element or an oxygen-containing polar element is more preferable, and an oxygen-containing polar element is further preferable.

  Examples of the oxygen-containing polar element include a hydroxyl group, an alkylol group, an alkoxy group, a formyl group, a carboxyl group, an ether group, a carbonyl group, a carbonate group, and an ester group. It is preferably a group linked to a carbon atom.

  As the nitrogen-containing polar element, at least one group selected from the group consisting of a cyano group, a primary amino group, a secondary amino group, a tertiary amino group, a pyridyl group, a carbamoyl group, and a ureido group, or the group is It is preferably a group linked to a carbon atom.

  The phosphorus-containing polar element is preferably at least one group selected from the group consisting of a phosphinyl group and a phosphate group, or a group in which the group is linked to a carbon atom.

  Therefore, the polar structure-containing group according to the present invention includes a group in which a cyclic group has an oxygen-containing polar element (hereinafter, referred to as an oxygen-containing cyclic group) and a group in which the cyclic group has a nitrogen atom polar element (hereinafter, referred to as a group containing a polar element). A nitrogen-containing cyclic group), a group in which the chain group has an oxygen-containing polar element (hereinafter, an oxygen-containing chain group) and a group in which the chain group has a nitrogen-atom polar element (hereinafter, a nitrogen-containing chain group), It is preferable that one or two or more groups selected from the group consisting of or a group containing the same are included, and from the viewpoint of adsorption ability, an oxygen-containing cyclic group, a sulfur-containing cyclic group, an oxygen-containing chain group, and a nitrogen-containing group. More preferably, it contains one or more kinds of groups selected from the group consisting of linear groups.

  The oxygen-containing cyclic group preferably has an ether group or a carbonyl group in the ring, and the ether group preferably includes the following groups.

  The carbonyl group, carbonate group and ester group preferably include any of the following groups.

  The nitrogen-containing cyclic group preferably contains any of the following groups.

  The oxygen-containing chain group preferably contains any of the following groups.

(In the above general formula, R ^at1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. In the above general formula, Z ^at1 is a single bond, a linear or branched group having 1 to 15 carbon atoms. Jo alkylene group or 2 to 18 carbon atoms in a linear or branched alkenylene groups, -CH 2 of the alkylene group or the alkenylene group _- is such that oxygen atoms are not directly adjacent -O-, —COO—, —C (＝ O) —, or ^—OCO— may be substituted, and X ^at1 represents an alkyl group having 1 to 15 carbon atoms, and —CH ₂ — of the alkyl group has an oxygen atom. (It may be substituted with -O-, -COO-, -C (= O)-, -OCO- so as not to be directly adjacent.)
The nitrogen-containing chain-type group preferably includes the following groups.

(In the above formula, R ^at , R ^bt , R ^ct and R ^dt each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.)
As the polar structure-containing group according to the present invention, a group represented by the following general formula (AT) is preferable.

(In the formula, Sp ^AT1 represents a single bond, a linear or branched alkylene group having 1 to 25 carbon atoms, and a hydrogen atom in the alkylene group is -OH, -CN, -W ^AT1 -Z ^AT1 or ^P AP1 ^{-Sp AP1} - may be substituted by, -CH ₂ in the alkylene group - the cyclic group such that oxygen atoms are not linked directly, -O -, - COO -, - C (= O )-, -OCO-, -CH = CH-,
W ^AT1 represents a single bond or the formula (WAT1) or (WAT2),

(In the formula, Sp ^WAT1 and Sp ^WAT2 each independently represent a single bond, a linear or branched alkylene group having 1 to 25 carbon atoms, and a hydrogen atom in the alkylene group is -OH,- ^CN, -Sp ^AT1 -W ^{AT1 -Z AT1} or ^P AP1 ^{-S AP1} - may be substituted by, -CH ₂ in the alkylene group - so does not bind the oxygen atom directly cyclic group, -O- , -COO-, -C (= O)-, -OCO-, -CH = CH-.)
Z ^AT1 represents a monovalent group containing a polar ^component, a hydrogen atom in ^{Z AT1} is ^{-OH, -CN, -Sp AT1 -W AT1} -Z AT1 or ^P AP1 ^{-S AP1} - may be substituted by . )
Sp ^AT1 , Sp ^WAT1 and Sp ^WAT2 each independently preferably represent a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, and a single bond or a linear carbon atom More preferably, it represents 1 to 20 alkylene groups, more preferably a single bond or a linear alkylene group having 2 to 10 carbon atoms. In Sp ^AT1 , Sp ^WAT1 and Sp ^WAT2 , one or two or more non-adjacent —CH ₂ — in the alkylene group are each independently —CH ^が so that an oxygen atom is not directly bonded. CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- may be substituted.

The ^hydrogen atoms in ^{Sp AT1} and ^{Sp WAT1} each ^{independently,} -Sp ^AT1 -W ^{AT1 -Z AT1} or ^P AP1 ^{-S AP1} - may be substituted for.

Z ^AT1 may represent a monovalent group containing a polar element is preferably a group represented by the general formula (ZAT1-1) or (ZAT1-2).

(In the formula, Sp ^ZAT11 and Sp ^ZAT12 each independently represent a linear or branched alkylene group having 1 to 25 carbon atoms, and hydrogen atoms in the alkylene group are -OH, -CN,- sp ^AT1 -W ^AT1 -Z ^AT1 or ^P AP1 ^{-S AP1} - may be substituted by, -CH ₂ in the alkylene group - as is not adjacent the oxygen atom directly cyclic group, -O -, - COO -, -C (= O)-, -OCO-, -CH = CH-,
Z ^ZAT11 represents a group containing a polar element, the structure represented by the ring containing Z ^ZAT12 in the general formula (ZAT1-2) represents a 5- to 7-membered ring, and the hydrogen atom of Z ^ZAT11 and Z ^ZAT12 is ^{-OH, -CN, -Sp AT1 -W AT1} -Z AT1 or ^P AP1 ^{-S AP1} - it may be substituted by,
R ^ZAT11 and R ^ZAT12 each independently represent a linear or branched alkyl group having 1 to 8 carbon atoms, wherein hydrogen atoms in the alkyl group are -OH, -CN, -Sp ^AT1 -W ^AT1 -Z ^AT1 or ^P AP1 ^{-S AP1} - may be substituted by, -CH ₂ in the alkyl group - is a cyclic group such that oxygen atoms are not linked directly, -O -, - COO -, - C (= O)-, -OCO-, and -CH = CH-. )
As the group represented by formula (ZAT1-1), groups represented by formulas (ZAT1-1-1) to (ZAT1-1-30) are preferable.

(Wherein a hydrogen atom bound to a carbon ^{atom, -OH, -CN, -Sp AT1 -W} AT1 -Z AT1 or ^P AP1 ^{-S AP1} - it may be substituted by,
Sp ^ZAT11 represents a linear or branched alkylene group of 1 to 25 carbon atoms, hydrogen atoms in the alkylene group ^{-OH, -CN, -Sp AT1 -W AT1} -Z AT1 or ^{P AP1} -S ^AP1 - may be substituted by, -CH ₂ in the alkylene group - the cyclic group such that oxygen atoms are not directly adjacent, -O -, - COO -, - C (= O) -, - OCO-, -CH = CH- may be substituted,
R ^ZAT11 represents a linear or branched alkyl group having 1 to 8 carbon atoms, hydrogen atoms in the alkyl group ^{-OH, -CN, -Sp AT1 -W AT1} -Z AT1 or ^{P AP1} -S ^AP1 - may be substituted by, -CH ₂ in the alkyl group - so does not bind the oxygen atom directly cyclic group, -O -, - COO -, - C (= O) -, - OCO- and -CH = CH- may be substituted. )
As the group represented by formula (ZAT1-2), groups represented by formulas (ZAT1-2-1) to (ZAT1-2-9) are preferable.

(Wherein a hydrogen atom bound to a carbon atom, a halogen ^{atom, -OH, -CN, -Sp AT1 -W} AT1 -Z AT1 or ^P AP1 ^{-S AP1} - it may be substituted by,
Sp ^ZAT11 represents a linear or branched alkylene group of 1 to 25 carbon atoms, hydrogen atoms in the alkylene group ^{-OH, -CN, -Sp AT1 -W AT1} -Z AT1 or ^{P AP1} -S ^AP1 - may be substituted by, -CH ₂ in the alkylene group - the cyclic group such that oxygen atoms are not directly adjacent, -O -, - COO -, - C (= O) -, - OCO- and -CH = CH- may be substituted. )
Examples of the group represented by the general formula (ZAT1-1) include the following groups.

(In the ^{formula, R tc} represents a hydrogen atom, a carbon atom number of 1 to 20 alkyl group or a polymerizable group ^P al ^{-Sp al} - represents, a hydrogen atom in the alkyl group -OH, -CN, - sp ^AT1 -W ^AT1 -Z ^AT1 or ^P AP1 ^{-S AP1} - may be substituted by, -CH ₂ in the alkyl group - as is not adjacent the oxygen atom directly cyclic group, -O -, - COO -, - C (= O) -, - OCO -, - CH = CH- may be substituted by a hydrogen atom in the molecule of the polymerizable group ^P al ^{-Sp al} - may be substituted by, * Represents a bond.)
In the spontaneous alignment compound according to the present invention, a mode in which a polar element contained in a polar structure-containing group or a polar element contained in a polymerizable group is localized is preferable. The polar structure-containing group is an important structure for vertically aligning the liquid crystal composition.Because the polar structure-containing group and the polymerizable group are adjacent to each other, better alignment can be obtained. Shows good solubility in Specifically, a form having a polymerizable group and a polar structure-containing group on the same ring of the mesogen group is preferred. In this case, the form in which one or more polymerizable groups and two or more polar structure-containing groups are respectively bonded on the same ring, and at least one of the one or more polymerizable groups or at least two or more polar structure-containing groups One of which is bonded to the other and has a polymerizable group and a polar structure-containing group on the same ring. In this case, the hydrogen atom of the spacer group of the polymerizable group may be substituted with a polar structure-containing group, and further, a form in which the hydrogen atom of the molecule of the polar structure-containing group is bonded to the spacer group of the polymerizable group. Including.
Further, as a preferable structure as the polar structure-containing group, partial structures represented by the following general formulas (K-1) to (K-17) can also be mentioned.

In the formula, P ⁱ¹ and Sp ⁱ¹ have the same meaning as in general formula (i), and X ^K1 and Y ^K1 are preferably —CH ₂ —, an oxygen atom or a sulfur atom, and an oxygen atom is particularly preferred. . Z ^K1 is preferably an oxygen atom or a sulfur atom, and particularly preferably an oxygen atom. W ^K1 , U ^K1 , V ^K1 and S ^K1 are preferably a methine group or a nitrogen atom. R ^K1 is preferably a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, and particularly preferably a hydrogen atom or a methyl group.
T ^K1 is each independently represented by the general formulas (T-1) to (T-6)

It preferably represents a group represented by ^ST1 is preferably a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms or a linear or branched alkenylene group having 2 to 18 carbon atoms. group or the alkenylene group -CH ₂ - such that oxygen atoms are not directly adjacent are -O -, - COO -, - C (= O) -, - C (= CH 2) - or -OCO- is substituted with Is preferred. R ^T1 is preferably an alkyl group having 1 to 5 carbon atoms, -CH ₂ of the alkyl groups - such that oxygen atoms are not directly adjacent are -O -, - COO -, - C (= O) _{-, - C (= CH 2} ) - or -OCO- be substituted, a particularly preferred from the viewpoint of the orientation property improving. Preferably, R ^T2 and R ^T3 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
Preferably the general formula (i) n ⁱ¹ and n ⁱ² in are each 1 to 3, more preferably 1 or 2, more preferably 2.

In the general formula (i), K ⁱ¹ and K ⁱ² is a polar structure-containing group is attached to the MES via respective Z ⁱ¹ and Z ^i2. Z ⁱ¹ and Z ⁱ² are preferably a single bond, -O-, -CH = CH-, -COO-, -OCO-, -OCOO-, -OOCO-, -CH = CHCOO-, -OCOCH = CH-, _{-CH = C (CH 3) COO} -, - OCOC (CH 3) = CH -, - CH 2 -CH (CH 3) COO -, - OCOCH (CH 3) -CH 2 -, or the number of carbon atoms 1 linear alkylene group having 20 represents a branched alkylene group having 1 to 20 carbon atoms, one or non-adjacent two or more -CH ₂ in the alkylene group - is -O -, - COO- or -OCO- in represents the substituted group, more preferably, -COO -, - OCO -, - OCH 2 CH 2 O-, or a linear or branched alkylene groups having 1 to 6 carbon atoms, or in ethylene group of -CH ₂ - 1 pieces are replaced with -O- in The group _{(-CH 2 O -, - OCH} 2 -), or -CH ₂ in the ethylene group - one is -COO -, - OCO- it has been substituted with _{(-CH 2} -CH 2 COO- , —OCOCH ₂ —CH ₂ —).

Further, Z ⁱ¹ and Z ^{i2 are, -Z i31 -S i1 - (Z} i31 - is -O -, - COO -, - OCO- or an alkylene group having 1 to 6 carbon atoms, in the alkylene radical one or not adjacent two or more -CH ₂ - is -O -, - COO- or -OCO- may be substituted ^{with, S i1} not represent a represents an alkyl group having 1 to 6 carbon atoms). Is preferred.

  The general formula (i) is preferably represented by the general formula (i-1).

(Where
Z ⁱ¹ , Z ⁱ² , K ⁱ¹ , K ⁱ² , n ⁱ¹ , n ⁱ² , P ^i1, and S ^p1 have the same meaning as in equation (i);
R ⁱ¹ represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a halogenated alkyl group, wherein —CH ₂ — in the alkyl group is —CH ＝ CH—, —C≡C— , -O -, - NH -, - COO- or may be substituted with -OCO-, but two adjacent -CH ₂ - is not to be replaced by -O- simultaneously,
A ⁱ¹ and A ⁱ² each independently represent an aromatic group, a heteroaromatic group, a cycloaliphatic group, or a ^{cycloheteroaliphatic} group, and a hydrogen atom in these groups is R ⁱ¹ , a halogen atom, or P ⁱ¹ − Sp ^i1- may be substituted;
Z ⁱ³ represents a divalent organic group,
m ⁱ¹ represents an integer of 0 to 4,
When a plurality of A ⁱ¹ , A ⁱ² or Z ⁱ³ are present in the formula, they may be the same or different;
^{Here, A i1, A i2, Z} i1, Z i2, Z i3, at least one or more groups selected from K ⁱ¹ and K ⁱ² is 1 or more P ⁱ¹ -Sp ⁱ¹ - substituted with. )
K ⁱ¹ and K ⁱ² in the general formula (i1) preferably has a partial structure represented by the above general formula (K-1) ~ (K -17). Among them, when the orientation of the liquid crystal is regarded as important, the general formulas (K-1), (K-3), (K-11), (K-12), and (K-13) are preferable. When importance is given to the general formulas (K-11), (K-12), (K-13), and (K-17) are preferable, and when importance is attached to the solubility in the liquid crystal compound, the general formula (K-11) K-8), (K-15) and (K-16) are preferred. X ^K1 and Y ^K1 are preferably oxygen atoms from the viewpoint of improving the alignment of the liquid crystal. Z ^K1 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom from the viewpoint of improving the voltage holding ratio (VHR). W ^K1 represents a methine group or a nitrogen atom, and preferably represents a methine group. U ^K1 , V ^K1 and Z ^K1 represent a methine group or a nitrogen atom, and a nitrogen atom is preferable from the viewpoint of improving the orientation of the liquid crystal.

^TK1 is preferably a group represented by the above-mentioned general formulas (T-1) to (T-6).
Among them, groups represented by formulas (T-1), (T-3) and (T-4) are preferable. S ^T1 in formula (T-3) is a single bond, -C 1-10 linear or branched alkylene group or a C2-10 straight-chain or branched alkenylene It preferably represents a linear or branched alkyl group having 1 to 7 carbon atoms or a linear or branched alkenylene group having 2 to 7 carbon atoms, and preferably has 1 to 3 carbon atoms. preferably a linear alkyl group, -CH ₂ in the alkyl group or alkylene group - such that oxygen atoms are not directly adjacent are -O -, - C (= O ) - or -C (= CH ₂₎ - in It is preferably substituted. R ^T1 in the general formula (T-3) represents a linear or branched alkyl group having 1 to 5 carbon atoms, and -CH _{2-of the} alkyl group is-so that an oxygen atom is not directly adjacent. O -, - C (= O ) -, - C (= CH 2) - or is preferably substituted on -OCO-, preferably a linear alkyl group having 1 to 3 carbon atoms. In the general formula (T-3), at least two or more secondary carbon atoms preferably include -C (= O).

R ^T2 and R ^T3 in the general formula (T-6) each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, but preferably a hydrogen atom or a methyl group.

  Preferred examples of the general formulas (K-1) to (K-17) include the following (K-1-1) to (K-16-3). From the viewpoints of orientation and orientation stability, Formulas (K-1-1), (K-1-3), (K-3-1), (K-11-1), (K-12-1), (K-13-1), K-13-3), (K-15-1) and (K-15-3) are preferred, and particularly preferred are formulas (K-1-1), (K-11-1) and (K-13-). 1) and (K-13-3).

In the formula, P ⁱ¹ represents the same meaning as P ^{i1 in} formula (i-1), and R ^T4 , R ^T5, and R ^T6 are each independently preferably an alkyl group having 1 to 3 carbon atoms. , N ^T1 and n ^T2 are preferably each independently 0 or 1, and n ^T2 is preferably each independently an integer of 1 to 3.

Z ⁱ¹ , Z ⁱ² and Z ⁱ³ in the general formula (i-1) are preferably a single bond, -O-, -CH = CH-, -COO-, -OCO-, -OCOO-, -OOCO-, _{-CH = CHCOO -, - OCOCH =} CH -, - CH = C (CH 3) COO -, - OCOC (CH 3) = CH -, - CH 2 -CH (CH 3) COO -, - OCOCH (CH 3 ) -CH ₂ -, or straight-chain alkylene group having 1 to 20 carbon atoms, represents a branched alkylene group having 1 to 20 carbon atoms, not one or adjacent in the alkylene group two or more -CH ₂ - is -O -, - COO- or a substituted radicals in -OCO-, more preferably, -COO -, - OCO -, - OCH 2 CH 2 O-, or straight-chain having 1 to 6 carbon atoms Or branched alkylene group or -C in ethylene group ₂ - the one has been group _(-CH 2 O -, - _OCH 2 -) substituted by -O-, or -CH ₂ in the ethylene group - one is -COO -, - OCO- substituted with groups _{(-CH 2 -CH 2 COO -,} - OCOCH 2 -CH 2 -) a.

Further, Z ^i1, Z ⁱ² and Z ^{i3 is, -Z i31 -S i1 - (Z} i31 - is -O -, - COO -, - OCO- or an alkylene group having 1 to 6 carbon atoms, said alkylene two or more -CH ₂ without one or adjacent in groups - is -O -, - COO- or -OCO- may be substituted ^{with, S i1} represents an alkyl group having 1 to 6 carbon atoms). It is preferable to represent
R ⁱ¹ represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a halogenated alkyl group, wherein —CH ₂ — in the alkyl group is —CH ＝ CH—, —C≡C— , -O -, - NH -, - COO- or -OCO- may be substituted, but with, adjacent two -CH ₂ - may not be substituted -O- simultaneously, more preferably, carbon linear or branched alkyl group having the number of atoms of 1 to 18, -CH ₂ in the alkyl group - is, -CH = CH -, - O -, - substituted (provided that -O- in OCO- is not a continuous ) May be. From the viewpoint of improving the orientation of the liquid crystal compound, the number of carbon atoms in R ⁱ¹ is preferably 3 or more, more preferably 4 or more, and preferably 5 or more.

A ⁱ¹ in the general formula (i-1) is the same or different and is preferably an aromatic group, a heteroaromatic group, a cycloaliphatic group, or a cycloheteroaliphatic group; , 4-Cyclohexylene group, anthracene-2,6-diyl group, phenanthrene-2,7-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl A ring structure selected from a group, an indane-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group and a 1,3-dioxane-2,5-diyl group Are preferred, and a 1,4-phenylene group, a 2,6-naphthalene group or a 1,4-cyclohexyl group is more preferred. Also, if R ⁱ¹ ring structure is ^{unsubstituted,} halogen atom, a cyano group, a nitro group, or P ⁱ¹ -Sp ⁱ¹ - preferably substituted with, inter alia an alkyl group having 1 to 12 carbon atoms, a carbon halogenated alkyl group of atoms from 1 to 12, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom or a P ⁱ¹ -Sp ⁱ¹ - be substituted with preferably And a group which is unsubstituted or substituted by an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a halogen atom.
A ⁱ² in the general formula (i-1) represents a 1,3,4-phenylene group, a 1,3,5-phenylene group, a 1,3,4-cyclohexylene group, a 1,3,5-cyclohexylene group And a ring structure selected from pyridine-2,4,5-diyl group, pyridine-2,4,6-diyl group, pyrimidine-2,4,5-diyl group, pyrimidine-2,4,6-diyl group And more preferably a 1,3,4-phenylene group or a 1,3,5-phenylene group. Also, if R ⁱ¹ ring structure is ^{unsubstituted,} halogen atom, a cyano group, a nitro group, or P ⁱ¹ -Sp ⁱ¹ - preferably substituted with, inter alia an alkyl group having 1 to 12 carbon atoms, a carbon halogenated alkyl group of atoms from 1 to 12, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom or a P ⁱ¹ -Sp ⁱ¹ - be substituted with preferably And a group which is unsubstituted or substituted by an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a halogen atom.
^Mi 1 in the general formula (i-1) is preferably an integer of 0 to 4, and is preferably 1 to 3 in order to increase the solubility in the liquid crystal composition. Is preferably 2 to 4.

At least one group is selected from A ⁱ¹ in the general formula ^{(i1), A i2, Z} i1, Z i2, Z i3, K i1, K i2, 1 or more P ⁱ¹ -Sp ⁱ¹ - in Has been replaced. Thereby, the spontaneous alignment compound according to the present invention can be polymerized after being adsorbed on the substrate, and the alignment of the liquid crystal is stably maintained even when the device is used thereafter.
P ⁱ¹ in the general formula (i-1) represents a polymerization functional group, and each independently represents a substituent selected from the group represented by the following general formulas (P-1) to (P-14). It is preferred to represent. Formulas (P-1) and (P-2) are more preferable from the viewpoint of simplicity of handling and reactivity.

(In the formula, the rightmost black dot represents a bond.)
Sp ⁱ¹ in the general formula (i-1) represents a single bond or a divalent linking group, preferably a single bond, —O—, —CH ＝ CH—, —COO—, —OCO—, —OCOO—, _{-OOCO -, - CH = CHCOO -} , - OCOCH = CH -, - CH = C (CH 3) COO -, - OCOC (CH 3) = CH -, - CH 2 -CH (CH 3) COO -, - OCOCH (CH ₃ ) —CH ₂ — or a linear alkylene group having 1 to 20 carbon atoms, a branched alkylene group having 1 to 20 carbon atoms, and one or two or more non-adjacent ones in the alkylene group -CH ₂ - is -O -, - COO- or -OCO- represents a substituted group, the more preferably, -COO -, - OCO -, - OCH 2 CH 2 O-, or number of carbon atoms 1 6 linear or branched alkylene groups, or ethylene A group in which one of —CH ₂ — in the propylene group is substituted with —O— (—CH ₂ O—, —OCH ₂ —), or one of —CH ₂ — in the propylene group is —COO—, It has been substituted with _{-OCO- (-CH 2 -CH 2 COO -} , - OCOCH 2 -CH 2 -) a. Among them, a single bond, a linear or branched alkylene group having 1 to 6 carbon atoms, and a linear or branched alkyleneoxy group having 1 to 6 carbon atoms are particularly preferable.

  It is particularly preferable that the general formula (i-1) represents the general formula (i-1-a) or the general formula (i-1-b).

(Where
R ^i1a represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, and —CH ₂ — in the alkyl group may be substituted with —O—, —COO—, or —OCO—. (Two adjacent —CH ₂ — are not simultaneously substituted with —O—),
Z ^i1a , Z ^i2a , Z ^i3a and Z ^i3b each independently represent a single bond, a linear alkylene group having 1 to 4 carbon atoms, wherein -CH _2- in the alkyl group is -O-, -COO — Or —OCO— (two adjacent —CH ₂ — are not simultaneously replaced by —O—),
^Ki1a and ^Ki2a are represented by the formulas (K-1-1a), (K-3-1a), (K-13-1a) or (K-13-3a),

(Wherein black dots represents a bond, Tk is a hydrogen atom, a methyl group, an ethyl group, or P ⁱ¹ -Sp ⁱ¹ - represents a.)
m ^i1a and m ^i1b represent an integer of 0 to 2, wherein mi1a + mib1 is 2 or 3,
n ^i1a and n ^i1b each represent 1,
Hydrogen atom in the phenyl group in the formula R ^i1, halogen atom, or a P ⁱ¹ -Sp ⁱ¹ - may be substituted with,
Wherein the phenyl group in the ^{formula, Z i1a, Z i2a, K} i1a at least one or more groups selected from and K ^i2a 1 or more P ⁱ¹ -Sp ⁱ¹ - is substituted with,
P ⁱ¹ is represented by the formula (P-1) or (P-2),
Sp ⁱ¹ represents a single bond, a linear or branched alkylene group having 1 to 6 carbon atoms, or a linear or branched alkyleneoxy group having 1 to 6 carbon atoms, and -CH in the alkyl group ₂ - is -O -, - COO- or -OCO- also may be substituted with (two -CH adjacent ₂ - is not to be replaced by -O- simultaneously). )
In addition, the present inventors have found that the polymerizable compound represented by the general formula (i) of this embodiment has at least two partial structures represented by the general formulas (K-1) to (K-17); It has been found that, by having a P ⁱ¹ -Spi ¹ -group, not only alignment of liquid crystal molecules but also improvement in stability of alignment and solubility in a liquid crystal composition can be ensured.

From the above viewpoints, the polymerizable compound of the present embodiment has at least two partial structures represented by general formulas (K-1) to (K-17) at the terminal of the molecule, preferably at the terminal of the main chain of the molecule. And a chemical structure having a P ⁱ¹ -Spi ¹ -group, and other chemical structures are not particularly limited as long as the functions of the liquid crystal composition are not impaired.

  More specific examples of the general formula (i-1) are represented by the following formulas (R-1-1) to (R-1-10), but are not limited thereto.

(Wherein R ⁱ¹ , P ⁱ¹ and Sp ⁱ¹ each independently represent the same meaning as R ⁱ¹ , P ⁱ¹ and Sp ⁱ¹ in the general formula (i-1), and the phenyl group in the formula further represents It may be substituted with a P ⁱ¹ -Spi ¹ -group.)
In the general formula (i-1), the formulas (R-1-1) to (R-1-10) and the like, preferred groups for each symbol are the same as those in the general formula (i-1).

  When added for a liquid crystal composition, one or more compounds represented by the general formula (i) of the present invention may be added, and in addition to the compound represented by the general formula (i), It may further contain a known polymerizable compound, an antioxidant and the like used in the liquid crystal composition. Specific examples of the compound (i) include the following (P-1) to (P-30).

(Production Method 1) Production of Compound Represented by General Formula (P-1) A Suzuki coupling reaction between a compound (P-1-S1) having the following structure and 4-bromocatechol using a palladium catalyst was carried out (P-1). -1-S2) is obtained. Next, (P-1-S4) is obtained by a Williamson reaction with (P-1-S3), and (P-1-S5) is obtained by a subsequent esterification reaction with methacrylic acid. Further, after the acetal is deprotected to give (P-1-S6), the desired product (P-1) can be obtained by cyclocarbonation. In addition, (P-1-S6) which passed through as an intermediate can also be mentioned as an example of the specific compound of the compound (i) in the present invention.

(Production Method 2) Production of Compound Represented by General Formula (P-4) A compound (P-4-S1) having the following structure and 4-bromoresorcinol were subjected to a Suzuki coupling reaction using a palladium catalyst to produce a compound (P-4). -4-S2) is obtained. Next, (P-4-S4) is obtained by a Williamson reaction with (P-4-S3), and then (P-4-S6) is obtained by deprotection of a benzyl group and an esterification reaction with methacrylic acid. Further, the target product (P-4) can be obtained by deprotection of the acetal to give (P-4-S7), followed by cyclocarbonation. In addition, (P-4-S7) which passed through as an intermediate can also be mentioned as a specific example of the compound (i) in the present invention.

(Production Method 3) Production of Compound Represented by General Formula (P-13) A compound (P-13-S1) having the following structure and 4-bromocatechol are subjected to a Suzuki coupling reaction using a palladium catalyst to give (P-13) -13-S2) is obtained. Next, (P-13-S4) is obtained by a Williamson reaction with (P-13-S3), and then (P-13-S6) is obtained by deprotection of an acetyl group and an esterification reaction with methacrylic acid. Further, the target compound (P-13) can be obtained by deprotection of the acetal.

(Production Method 4) Production of Compound Represented by General Formula (P-21) A compound (P-21-S1) having the following structure and 4-bromoresorcinol were subjected to a Suzuki coupling reaction using a palladium catalyst to give (P 21-S2) is obtained. Next, (P-21-S4) is obtained by a Williamson reaction with (P-21-S3), and (P-21-S5) is obtained by a subsequent esterification reaction with methacrylic acid. Furthermore, after deprotection of acetal to (P-21-S6), the target product (P-21) can be obtained by oxalic acid esterification. In addition, (P-21-S6) which passed through as an intermediate can also be mentioned as an example of the specific compound of the compound (i) in the present invention.

(Production method 2) Production of compound represented by general formula (P-28) A compound (P-28-S1) having the following structure and 4-bromoresorcinol were subjected to a Suzuki coupling reaction using a palladium catalyst to give (P-28-S1). -28-S2). Next, (P-28-S4) is obtained by a Williamson reaction with (P-28-S3), and (P-28-S5) is obtained by a subsequent esterification reaction with methacrylic acid. Further, after the acetal is deprotected to give (P-28-S6), the desired product (P-28) can be obtained by malonic acid esterification. In addition, (P-28-S6) which passed through as an intermediate can also be mentioned as a specific example of the compound (i) in the present invention.

(Liquid crystal composition)
The liquid crystal composition of the present embodiment contains one or more compounds having a partial structure represented by the general formula (i). This liquid crystal composition preferably has a negative dielectric anisotropy (Δε). The compound having a partial structure represented by the general formula (i) contained in the liquid crystal composition includes the compound (i) including the compounds represented by the formulas (R-1) to (R-30). ), The description is omitted here.

  The content of the compound (i) is preferably 0.01 to 50% by mass, and the lower limit is preferably based on the total amount of the liquid crystal composition, from the viewpoint of more appropriately aligning the liquid crystal molecules. It is 0.01% by mass or more, 0.1% by mass or more, 0.5% by mass or more, 0.7% by mass or more, or 1% by mass or more. The upper limit of the content of the compound (i) is preferably 50% by mass or less, 30% by mass or less, 10% by mass or less, and 7% by mass, based on the total amount of the liquid crystal composition, from the viewpoint of excellent response characteristics. Below, 5% by mass or less, 4% by mass or less, or 3% by mass or less.

  The liquid crystal composition has a general formula (N-1), (N-2) and (N-3) as a non-polymerizable liquid crystal compound:

Or a compound selected from the group of compounds represented by any of the above.

In the formulas (N-1), (N-2) and (N-3),
^RN11 , ^RN12 , ^RN21 , ^RN22 , ^RN31 and ^RN32 each independently represent an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent alkyl groups in the alkyl group -CH ₂ -may be each independently substituted by -CH = CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-,
A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 each independently represent
(A) 1,4-cyclohexylene group, (this is present in the group one -CH ₂ - - or nonadjacent two or more -CH ₂ may be replaced by -O-.)
(B) 1,4-phenylene group (one -CH = or two or more non-adjacent -CH = present in this group may be substituted 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 = or two or more non-adjacent -CH = present in the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted by -N =. ) And (d) represents a group selected from the group consisting of 1,4-cyclohexenylene groups, wherein the groups (a), (b), (c) and (d) are each independently May be substituted with a cyano group, a fluorine atom or a chlorine atom,
^{Z N11, Z N12, Z N21} , Z N22, Z N31 and ^{Z N32} are each independently a single _{bond, -CH 2 CH 2 -, -} (CH 2) 4 -, - OCH 2 -, - CH 2 _{O -, - COO -, -} OCO -, - OCF 2 -, - CF 2 O -, - CH = N-N = CH -, - CH = CH -, - CF = CF- or -C≡C- the Represent
X ^N21 represents a hydrogen atom or a fluorine atom,
T ^N31 is, -CH ₂ - represents an or an oxygen atom,
n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31 and n ^N32 each independently represent an integer of 0 to 3, but n ^N11 + n ^N12 , n ^N21 + n ^N22 and n ^N31 + n ^N32 each independently represent an integer. 1, 2, or 3,
When a plurality of A ^{N11 to} A ^N32 and a plurality of Z ^{N11 to} Z ^N32 are present, they may be the same or different from each other.

  The compound represented by any of the general formulas (N-1), (N-2) and (N-3) is preferably a compound 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 each independently have 1 to 8 carbon atoms. Alkyl group, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, and an alkyl group having 1 to 5 carbon atoms, An alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferable. More preferably, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is further preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable.

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

  The alkenyl group is preferably selected from groups represented by any of formulas (R1) to (R5) (in each formula, a black dot represents a bond).

A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31 and A ^N32 are each preferably aromatic when it is required to increase Δn independently. And a trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5 -Difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1 , 4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl Preferred, the following structure:

And more preferably a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group, or a 1,4-phenylene group.

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

^XN21 is preferably a fluorine atom.

T ^N31 is preferably an oxygen atom.

n ^N11 + n ^N12 , n ^N21 + n ^N22 and n ^N31 + n ^N32 are preferably 1 or 2, a combination in which n ^N11 is 1 and n ^N12 is 0, a combination in which n ^N11 is 2 and n ^N12 is 0, n ^A combination in which ^N11 is 1 and n ^N12 is 1, a combination in which n ^N11 is 2 and n ^N12 is 1, a combination in which n ^N21 is 1 and n ^N22 is 0, a combination in which n ^N21 is 2 and n ^N22 are A combination in which n ^N31 is 1 and n ^N32 is 0, and a combination in which n ^N31 is 2 and n ^N32 is 0 are preferable.

  The lower limit of the preferable content of the compound represented by the formula (N-1) based on the total amount of the composition of the present embodiment is 1% by mass or more, 10% by mass or more, and 20% by mass or more. 30% by mass or more, 40% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, 65% by mass or more, 70% by mass or more Yes, 75% by mass or more, and 80% by mass or more. The upper limit of the preferred content is 95% by mass or less, 85% by mass or less, 75% by mass or less, 65% by mass or less, 55% by mass or less, 45% by mass or less, 35% by mass or less, 25% by mass or less, and 20% by mass or less.

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

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

  When a composition having a high response speed is required while keeping the viscosity of the composition of the present embodiment low, it is preferable that the lower limit is lower and the upper limit is lower. Further, when a composition having good temperature stability is required while keeping the composition of the present embodiment at a high Tni, it is preferable that the lower limit is lower and the upper limit is lower. When it is desired to increase the dielectric anisotropy in order to keep the drive voltage low, it is preferable that the lower limit is set higher and the upper limit is set higher.

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

^{(Wherein, R N11} and ^{R N12} are as defined ^{R N11} and ^{R N12} in the general formula ^{(N-1), n Na11} represents 0 or ^{1, n NB11} represents 0 or ^{1, n NC11} is represents 0 or ^{1, n Nd11} represents 0 or ^{1, n NE11} is 1 or ^{2, n Nf11} is 1 or ^{2, n NG11} is 1 or ^{2, a NE11} is trans-1,4 ^{Represents a} cyclohexylene group or a 1,4-phenylene group, and A ^Ng11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group, or a 1,4-phenylene group, but at least one of them represents Represents a 1,4-cyclohexenylene group, ^{ZNe 11} represents a single bond or ethylene, but at least one represents ethylene.)
More specifically, the compound represented by the general formula (N-1) is a compound selected from the group of compounds represented by the general formulas (N-1-1) to (N-1-21). Is preferred.

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

^{(Wherein, R N111} and ^{R N112} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
^RN111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably a propyl group, a pentyl group or a vinyl group. ^RN112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group or a butoxy group.

^{(Wherein, R N121} and ^{R N122} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N131} and ^{R N132} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

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

(In the formula, R ^N151 and R ^N152 each independently represent the same meaning as R ^N11 and R ^N12 in General Formula (N-1).)
The compound represented by formula (N-1-10) is as follows.

^{(Wherein, R N1101} and ^{R N1102} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1111} and ^{R N1112} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1121} and ^{R N1122} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1131} and ^{R N1132} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1141} and ^{R N1142} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1151} and ^{R N1152} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1161} and ^{R N1162} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1171} and ^{R N1172} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1181} and ^{R N1182} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1201} and ^{R N1202} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)

^{(Wherein, R N1211} and ^{R N1212} independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
The compounds represented by the general formulas (N-1) to (N-3) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in an appropriate combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind in one embodiment, two kinds, three kinds, four kinds, five kinds or more.

When the improvement of Δε is emphasized, it is preferable to set the content higher. When the solubility at a low temperature is emphasized, setting the content higher is more effective. When the T _NI is emphasized, the content is higher. The effect is high if is set to a small value. Further, in order to improve dripping marks and seizure characteristics, it is preferable to set the content range in the middle.

  The lower limit of the preferred content of the compounds represented by formulas (N-1) to (N-3) based on the total amount of the composition of the present embodiment is 5% by mass or more, and 10% by mass. % Or more, 13% by mass or more, 15% by mass or more, 17% by mass or more, 20% by mass or more, 23% by mass or more, 25% by mass or more, 27% by mass Not less than 30% by mass, not less than 33% by mass, and not less than 35% by mass. The upper limit of the preferable content is 50% by mass or less, 40% by mass or less, 38% by mass or less, 35% by mass or less, and 33% by mass or less based on the total amount of the composition of the present embodiment. % Or less, 30% by mass or less, 28% by mass or less, 25% by mass or less, 23% by mass or less, 20% by mass or less, 18% by mass or less, 15% by mass 13% by mass or less, 10% by mass or less, 8% by mass or less, 7% by mass or less, 6% by mass or less, 5% by mass or less, 3% by mass or less It is.

  Further, the compound represented by the general formula (N-1-1) is a compound selected from the group of compounds represented by the formulas (N-1-1.1) to (N-1-1.23). It is preferable that they are compounds represented by the formulas (N-1-1.1) to (N-1-1.4), and the compounds represented by the formulas (N-1-1.1) and (N-1.1) Compounds represented by 1-1.3) are preferred.

  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 embodiment The lower limit of the preferred content of these compounds alone or with respect to the total amount is 5% by mass or more, and the upper limit is 50% by mass or less based on the total amount of the composition of the present embodiment.

  Further, the liquid crystal composition may contain a so-called non-polar liquid crystal compound having a dielectric anisotropy of about 0 as a non-polymerizable liquid crystal compound. Examples of the non-polar liquid crystal compound include a compound represented by the following general formula (LC6).

( ^Wherein , R ^LC61 and R ^LC62 each independently represent an alkyl group having 1 to 15 carbon atoms, and one or more —CH ₂ — in the alkyl group is not directly adjacent to an oxygen atom. As described above, -O-, -CH = CH-, -CO-, -OCO-, -COO- or -C≡C- may be substituted, and one or more hydrogen atoms in the alkyl group may be substituted. ^May be arbitrarily substituted with halogen, and A ^{LC61 to} A ^LC63 are each independently

(In the structure, one or more of —CH ₂ CH ₂ — in the cyclohexylene group may be substituted with —CH ＝ CH—, —CF ₂ O—, —OCF ₂ —, and 1,4 And one or more CH groups in the phenylene group may be substituted with a nitrogen atom.), ^ZLC61 and ^ZLC62 each independently represent a single bond, -CH = CH-, —C≡C—, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —COO—, —OCH ₂ —, —CH ₂ O—, —OCF ₂ — or —CF ₂ O—, m ^Lc6 represents 0 to 3. However, the compounds represented by the general formulas (LC1) to (LC5) and the general formula (i) are excluded. )
R ^LC61 and R ^LC62 are each independently preferably an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, and an alkenyl group having 2 to 7 carbon atoms, and the alkenyl group has the following structure: Most preferably,

(In the formula, the ring structure is bonded at the right end.)
^{ALC61 to ALC63} each independently preferably has the following structure,

Z ^LC61 and ^{Z LC62} each independently represent a single _{bond, -CH 2 CH 2 -, -} COO -, - OCH 2 -, - CH 2 O -, - OCF 2 - or _-CF 2 O-are preferred.

  The general formula (LC6) is obtained by converting the general formula (LC6-a) to the general formula (LC6-m)

( ^Wherein , R ^LC61 and R ^LC62 each independently represent an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms or 2 to 7 carbon atoms. And more preferably one or more compounds selected from the group consisting of compounds represented by the following formulae:

  Further, the liquid crystal composition of the present invention may further contain another polymerizable compound different from the compound represented by the general formula (i). The polymerizable compound may be a known polymerizable compound used in a liquid crystal composition. Examples of the polymerizable compound include a compound represented by the general formula (P):

The compound represented by is mentioned.

In the formula (P),
Z ^p1 is a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms in which a hydrogen atom may be substituted with a halogen atom, or a carbon atom in which a hydrogen atom may be substituted with a halogen atom. An alkoxy group having 1 to 15 carbon atoms, an alkenyl group having 1 to 15 carbon atoms where a hydrogen atom may be substituted with a halogen atom, an alkenyloxy having 1 to 15 carbon atoms optionally having a hydrogen atom substituted with a halogen atom A group or —Sp ^p2 —R ^p2 ;
R ^p1 and R ^p2 are represented by the following formulas ( ^RI ) to (R-VIII):

(Where
* Binds to Sp ^p1 ,
R ^{2 to} R ⁶ each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms,
W represents a single bond, -O- or a methylene group,
T represents a single bond or -COO-,
p, t and q each independently represent 0, 1 or 2. )
Represents one of
Sp ^p1 and Sp ^p2 represent a spacer group,
L ^p1 and L ^p2 each independently represent a single bond, —O—, —S—, —CH ₂ —, —OCH ₂ —, —CH ₂ O—, —CO—, —C ₂ H ₄ —, _{-COO -, - OCO -, -} OCOOCH 2 -, - CH 2 OCOO -, - OCH 2 CH 2 O -, - CO-NR a -, - NR a -CO -, - SCH 2 -, - CH 2 S ^{-, - CH = CR a -COO} -, - CH = CR a -OCO -, - COO-CR a = CH -, - OCO-CR a = CH -, - COO-CR a = CH-COO -, - ^{COO-CR a = CH-OCO} -, - OCO-CR a = CH-COO -, - OCO-CR a = CH-OCO -, - (CH 2) z -C (= O) -O -, - ( _{CH 2) z -O- (C =} O) -, - O- (C = O) - (CH 2) z -, - (C = O _{-O- (CH 2) z -,} - CH = CH -, - CF = CF -, - CF = CH -, - CH = CF -, - CF 2 -, - CF 2 O -, - OCF 2 -, —CF ₂ CH ₂ —, —CH ₂ CF ₂ —, —CF ₂ CF ₂ — or —C≡C— (wherein ^Ra is each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. And z represents an integer of 1 to 4.)
^Mp2 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, an anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2, 5-diyl group, naphthalene-2,6-diyl group, indane-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, 1,3-dioxane-2,5 Represents a diyl group or a single bond, wherein M ^p2 is unsubstituted or 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 ^May be substituted with a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or -R ^p1 ,
M ^p1 is ^{calculated according} to the following formulas (i-11) to (ix-11):

(In the formula, * binds to Sp ^p1 and ** binds to L ^p1 , L ^p2 or Z ^p1 .)
Represents one of
Any hydrogen atom on M ^p1 may be 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, or a halogenation having 1 to 12 carbon atoms. ^May be substituted with an alkoxy group, a halogen atom, a cyano group, a nitro group or -R ^p1 ,
M ^p3 is ^{calculated according} to the following formulas (i-13) to (ix-13):

(In the formula, * binds to Z ^p1 and ** binds to L ^p2 .)
Represents one of
Any hydrogen atom on M ^p3 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, halogenation having 1 to 12 carbon atoms. ^May be substituted with an alkoxy group, a halogen atom, a cyano group, a nitro group or -R ^p1 ,
m ^p2 ~m ^p4 are each independently 0, 1, 2 or 3,
^mp1 and ^mp5 each independently represent 1, 2 or 3,
Z ^p1 is or different even they are identical to each other when there are a plurality, in the case where R ^p1 there are a plurality or different even they are identical to each other, R ^p2 is more if present may be different even they are identical to each other, when Sp ^p1 there are a plurality or different even they are identical to each other, when Sp ^p2 there are multiple ^May be the same or different from each other, and when plural L ^p1 are present, they may be the same or different from each other, and when plural M ^p2 are present, they are mutually different. They may be the same or different.

  When the liquid crystal composition of the present embodiment further contains the polymerizable compound represented by the general formula (P) in addition to the compound (i), the pretilt angle of liquid crystal molecules can be suitably formed. Specific examples of the polymerizable compound represented by the general formula (P) are shown in (P-2-1) to (P-2-20).

(Liquid crystal display device)
The liquid crystal composition of the present embodiment is applied to a liquid crystal display device. The liquid crystal display element may be an active matrix driving liquid crystal display element. The liquid crystal display element may be a PSA type, PSVA type, VA type, IPS type, FFS type or ECB type liquid crystal display element, and is preferably a PSA type liquid crystal display element.

  In the liquid crystal display element of the present embodiment, since the liquid crystal composition containing the compound represented by the general formula (i) is used, the polyimide alignment film is provided on the first substrate 2 and the second substrate 3 on the liquid crystal layer 4 side. It is not necessary to provide an alignment film such as That is, the liquid crystal display element of the present embodiment can have a configuration in which at least one of the two substrates does not have an alignment film such as a polyimide alignment film.

Hereinafter, the present invention will be described more specifically based on examples, but the present invention is not limited to the examples.
Example 1 Production of Compound (P-21)

(1-1) Under dry nitrogen, 4- (4-pentylcyclohexyl) -2-fluorophenylboric acid (127 g, 434 mmol), 2-ethyl-4-propyloxybromobenzene (96 g, 395 mmol), PdCl2 (amphos) 2 (2.8 g, 4 mmol), potassium carbonate (82 g, 592 mmol), THF (1 L) and H2O (330 mL) were mixed and reacted under reflux for 5 hours. After ethyl acetate was added to the reaction solution, the layers were separated, and the organic layer was washed with saturated saline (500 mL). After drying by adding anhydrous sodium sulfate, sodium sulfate was removed by filtration, and the organic solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain compound (1-1) (160 g) as a colorless liquid.

(1-2) Compound (1-1) (68 g, 166 mmol) and methylene chloride (480 mL) were mixed under dry nitrogen, and boron tribromide (50 g, 200 mmol) was added dropwise under ice cooling. After the addition, the reaction was carried out at room temperature for 1 hour. The reaction solution was ice-cooled, and water (300 mL) was added dropwise. Methylene chloride (200 mL) was added to the reaction solution, and the mixture was separated. The organic layer was washed with saturated saline (500 mL). After drying by adding anhydrous sodium sulfate, sodium sulfate was removed by filtration, and the organic solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain Compound (1-2) (68 g) as a colorless solid.

(1-3) Compound (1-2) (68 g, 166 mmol), pyridine (26 g, 333 mmol) and methylene chloride (340 mL) were mixed under dry nitrogen, and trifluoromethanesulfonic anhydride (56 g) was mixed under ice cooling. , 200 mmol) was added dropwise. The reaction solution was ice-cooled, and water (100 mL) was added dropwise. Methylene chloride (100 mL) was added to the reaction solution, and the mixture was separated. The organic layer was washed with a 10% aqueous hydrochloric acid solution (100 mL) and a saturated saline solution (400 mL) in this order. After drying by adding anhydrous sodium sulfate, sodium sulfate was removed by filtration, and the organic solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain Compound (1-3) (82 g) as a colorless liquid.

(1-4) Compound (1-3) (82 g, 164 mmol), bispinacolatodiborane (44 g, 171 mmol), PdCl2 (dppf) (4 g, 4.9 mmol), potassium acetate (48 g, 490 mmol) under dry nitrogen And DMF (410 mL) was mixed and reacted at 80 degrees for 5 hours. The reaction solution was cooled to room temperature, water (200 mL) and ethyl acetate (600 mL) were added, and the mixture was separated, and the organic layer was washed with saturated saline (900 mL). After drying by adding anhydrous sodium sulfate, sodium sulfate was removed by filtration, and the organic solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography, and recrystallized from hexane to obtain Compound (1-4) (62 g) as a colorless solid.

(1-5) Under dry nitrogen, compound (1-5) (12 g, 25 mmol), 3-bromoresorcinol (4.3 g, 23 mmol), PdCl2 (amphos) 2 (27 mg, 0.04 mmol), sodium carbonate ( (3.7 g, 35 mmol), CPME (43 mL) and water (8 mL) were mixed and reacted under reflux for 7 hours. After water (26 mL) and ethyl acetate (50 mL) were added to the reaction solution, the layers were separated, and the organic layer was washed with saturated saline (100 mL). After drying by adding anhydrous sodium sulfate, sodium sulfate was removed by filtration, and the organic solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain compound (1-5) (10 g) as a colorless liquid.

(1-6) Compound (1-5) (10 g, 21.7 mmol), 5- (bromomethyl) -2,2-dimethyl-1,3-dioxan-5-yl) methanol (16 g, 65 mmol) under dry nitrogen ), Potassium phosphate (14 g, 65 mmol) and DMF (100 mL) were mixed and reacted at 70 ° C. for 5 hours. The reaction solution was cooled to room temperature, water (100 mL) and ethyl acetate (200 mL) were added, the layers were separated, and the organic layer was washed with saturated saline (300 mL). After drying by adding anhydrous sodium sulfate, sodium sulfate was removed by filtration, and the organic solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain compound (1-6) (11 g) as a colorless liquid.

(1-7) Compound (1-6) (11 g, 14 mmol), methacrylic acid (4 g, 43 mmol), DMAP (0.2 g, 1.4 mmol) and methylene chloride (110 mL) were mixed under dry nitrogen, and the mixture was iced. Under cooling, diisopropylcarbodiimide (5.5 g, 43 mmol) was added dropwise, and the mixture was heated to room temperature and reacted for 12 hours. The reaction solution was filtered, and the organic solvent was distilled off under reduced pressure to obtain a crude product of compound (1-7). THF (125 mL) and a 10% aqueous hydrochloric acid solution (25 mL) were added to the crude product of the compound (1-7), and the mixture was reacted for 6 hours. After water (50 mL) and ethyl acetate (250 mL) were added to the reaction solution, the layers were separated, and the organic layer was washed with saturated saline (200 mL). After drying by adding anhydrous sodium sulfate, sodium sulfate was removed by filtration, and the organic solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain compound (1-8) (15 g) as a colorless liquid.

(P-21) Under dry nitrogen, compound (1-8) (5 g, 6 mmol), diisopropylethylamine (4 g, 30 mmol) and methylene chloride (50 mL) were mixed, and under ice-cooling, methyl chloroglyoxylate (4 g, 30 mmol). ) Was added dropwise, and the mixture was heated to room temperature and reacted for 12 hours. After water (10 mL) and methylene chloride (150 mL) were added to the reaction solution, the layers were separated, and the organic layer was washed with saturated saline (100 mL). After drying by adding anhydrous sodium sulfate, sodium sulfate was removed by filtration, and the organic solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain compound (P-21) (4 g) as a colorless solid.
Compounds (P-1) to (P-20) and (P-22) to (P-30) were synthesized using the same reaction as that for compound (P-21) or the method described in the above production method. .

(Example 31) Preparation of liquid crystal composition Composition composed of the following compounds and mixing ratio:

A composition obtained by adding 0.3 parts by mass of the following polymerizable compound (P-2-8) to 100 parts by mass of the liquid crystal composition LC-1 was defined as (LC-1).

  Further, 0.6 part by mass of the compound (P-1-27) synthesized in Example 1 was added to 100 parts by mass of (LC-1) to prepare a liquid crystal composition (LC-1M1).

The following evaluation test was performed about the liquid crystal composition (LC-1M1).
(Liquid crystal solubility test)
After storage at room temperature (25 ° C.) for one day, the presence or absence of precipitation was visually determined.

A: Uniformly dissolved state is maintained. B: Slight precipitation is observed. C: A large amount of crystals are precipitated (evaluation test of vertical orientation).
An alignment having a first substrate (common electrode substrate) having no alignment film including a transparent electrode layer composed of a transparent common electrode and a color filter layer, and a pixel electrode layer having a transparent pixel electrode driven by an active element A second substrate (pixel electrode substrate) having no film was manufactured. The liquid crystal composition was dropped on the first substrate, sandwiched on the second substrate, and cured at 120 ° C. for 1 hour under normal pressure to obtain a liquid crystal cell having a cell gap of 3.2 μm. At this time, the alignment unevenness such as vertical alignment and drop marks was observed using a polarizing microscope, and evaluated by the following four steps.

A: Vertical alignment uniformly over the entire surface including the end portions B: Acceptable level with very slight alignment defects C: Unacceptable level with many alignment defects including end portions D: Poorly poor alignment (Test for evaluating stability of pretilt angle)
Using a high-pressure mercury lamp, UV light having an illuminance of 100 m / cm ² at 365 nm was applied for 200 seconds using a high-pressure mercury lamp while applying a rectangular alternating wave of 10 V and 100 Hz to the liquid crystal cell used in the above (test for evaluating vertical alignment). Irradiated. Thereafter, the stability of white display was evaluated by applying a physical external force to the cell while applying a rectangular AC wave of 10 V and 100 Hz, allowing the cell to stand for a few minutes, and then observing the cell in a crossed Nicol state. did.

A: Vertical alignment uniformly over the entire surface including the end portions B: Acceptable level with very slight alignment defects C: Unacceptable level with many alignment defects including end portions D: Poorly poor alignment The liquid crystal composition (LC-1M1) had no problem with liquid crystal solubility (Level A). As a result of the evaluation test of the vertical orientation, uniform vertical orientation was shown (level A). Further, as a result of the pretilt angle stability evaluation test, uniform orientation was observed (level A).

  Similarly, 0.6 parts by mass of the compounds synthesized in Examples 2 to 30 were added to 100 parts by mass of the liquid crystal composition (LC-1) to prepare a liquid crystal composition.

(Comparative Example 1)
0.6 part by mass of a compound represented by the following formula (C-1) was added to 100 parts by mass of the liquid crystal composition (LC-1) to prepare a liquid crystal composition (LC-1C1).

The same evaluation test as in Example 31 was performed for the liquid crystal composition (LC-1C1). There was no problem in liquid crystal solubility (level A). As a result of the evaluation test of the vertical orientation, vertical orientation was shown (Level B). Further, as a result of the pretilt angle stability evaluation test, poor orientation was considerably poor (level D).
(Comparative Example 2)
0.6 part by mass of a compound represented by the following formula (C-2) was added to 100 parts by mass of the liquid crystal composition (LC-1) to prepare a liquid crystal composition (LC-1C2).

The same evaluation test as in Example 31 was performed for the liquid crystal composition (LC-1C2). There was no problem in liquid crystal solubility (level A). As a result of the evaluation test of the vertical orientation, vertical orientation was shown (Level B). As a result of the pretilt angle stability evaluation test, it was defective and at an unacceptable level (level C).
(Comparative Example 3)
0.6 parts by mass of a compound represented by the following formula (C-3) was added to 100 parts by mass of the liquid crystal composition (LC-1) to prepare a liquid crystal composition (LC-1C3). It was deposited and could not be evaluated.

(Comparative Example 4)
0.6 part by mass of the compound represented by the following formula (C-4) was added to 100 parts by mass of the liquid crystal composition (LC-1) to prepare a liquid crystal composition (LC-1C4).

The same evaluation test as in Example 31 was performed for the liquid crystal composition (LC-1C4). The liquid crystal solubility was slightly precipitated (level B). As a result of the evaluation test of the vertical orientation, vertical orientation was shown (Level B). Further, as a result of the evaluation test for forming the pretilt angle, a slight defect was observed (level B).
(Comparative Example 5)
0.6 part by mass of a compound represented by the following formula (C-5) was added to 100 parts by mass of the liquid crystal composition (LC-1) to prepare a liquid crystal composition (LC-1C5).

  An evaluation test similar to that of Example 31 was performed on the liquid crystal composition (LC-1C5). The liquid crystal solubility was slightly precipitated (level B). As a result of the evaluation test of the vertical alignment property, uniform vertical alignment was shown (level A). Further, as a result of the pretilt angle stability evaluation test, poor orientation was considerably poor (level D).

  As described above, the compound of the present invention has both alignment properties and pretilt stability, and can provide a liquid crystal composition having excellent storage stability.

Claims (10)

A polymerizable compound represented by the formula (i).

(Where
MES represents a mesogen group having one or more ring structures,
Z ⁱ¹ represents a (n ⁱ¹ +1) ^-valent organic group or a single bond;
Z ⁱ² represents a (n ⁱ² +1) ^-valent organic group or a single bond, wherein Z ⁱ¹ and Z ⁱ² are bonded on the same ring in the MES;
^Ki1 and ^Ki2 each independently represent a polar structure-containing group;
n ⁱ¹ and n ⁱ² each independently represent an integer from 1 to 3,
Here, MES, Z ^i1, Z ^i2, at least one or more groups selected from K ⁱ¹ and K ⁱ² is 1 or more P ⁱ¹ -Sp ⁱ¹ - is substituted with, here P ⁱ¹ polymerization functional group And Sp ⁱ¹ represents a single bond or a divalent linking group,
If K ^i1, K ^i2, P ⁱ¹ or Sp ⁱ¹ is more present in the formula, it may be be the same or different. ) The polymerizable compound according to claim 1, wherein the compound represented by the formula (i) is represented by the formula (i-1).

(Where
Z ⁱ¹ , Z ⁱ² , K ⁱ¹ , K ⁱ² , n ⁱ¹ , n ⁱ² , P ^i1, and S ^p1 have the same meaning as in equation (i);
R ⁱ¹ represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a halogenated alkyl group, wherein —CH ₂ — in the alkyl group is —CH ＝ CH—, —C≡C— , -O -, - NH -, - COO- or may be substituted with -OCO-, but two adjacent -CH ₂ - is not to be replaced by -O- simultaneously,
A ⁱ¹ and A ⁱ² each independently represent an aromatic group, a heteroaromatic group, a cycloaliphatic group, or a ^{cycloheteroaliphatic} group, and a hydrogen atom in these groups is R ⁱ¹ , a halogen atom, or P ⁱ¹ − Sp ^i1- may be substituted;
Z ⁱ³ represents a divalent organic group,
m ⁱ¹ represents an integer of 0 to 4,
When a plurality of A ⁱ¹ , A ⁱ² or Z ⁱ³ are present in the formula, they may be the same or different;
^{Here, A i1, A i2, Z} i1, Z i2, Z i3, at least one or more groups selected from K ⁱ¹ and K ⁱ² is 1 or more P ⁱ¹ -Sp ⁱ¹ - substituted with. ) The polymerizable compound according to claim 1, wherein K ⁱ¹ and K ⁱ² in formula (i) or (i-1) are represented by formulas (K-1) to (K-17). 4.

( ^Wherein P ⁱ¹ and Sp ⁱ¹ have the same meanings as in general formula (i), X ^K1 and Y ^K1 each independently represent —CH ₂ —, an oxygen atom or a sulfur atom, and Z ^K1 represents , Represents an oxygen atom or a sulfur atom, W ^K1 , U ^K1 , V ^K1 and S ^K1 each independently represent a methine group or a nitrogen atom, and R ^K1 is a hydrogen atom, a straight-chain having 1 to 6 carbon atoms. Represents a chain or branched alkyl group, and ^TK1 is each independently a group represented by any of the general formulas (T-1) to (T-6)

Represents a group represented by
^ST1 represents a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms or a linear or branched alkenylene group having 2 to 18 carbon atoms, and the alkylene group or the alkylene group -CH ₂ alkenylene groups - so that oxygen atoms are not directly adjacent are -O -, - COO -, - C (= O) -, - C (= CH 2) - or -OCO- may be substituted by , R ^T1 represents an alkyl group having 1 to 5 carbon atoms, and -CH _{2-of the} alkyl group is -O-, -COO-, -C (= O)-, such that an oxygen atom is not directly adjacent. -C (= CH ₂₎ - or -OCO- may be substituted ^{by, R T2} and ^{R T3} each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. ) A ⁱ¹ in the general formula (i-1) is a 1,4-phenylene group, a 1,4-cyclohexylene group, an anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, a pyridine-2, 5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, indan-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group and Represents a ring structure selected from 1,3-dioxane-2,5-diyl groups, wherein the ring structure is unsubstituted or an alkyl group having 1 to 12 carbon atoms, and a halogenated group having 1 to 12 carbon atoms. It represents a group which may be substituted by - an alkyl group, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or a P ⁱ¹ -Sp ⁱ¹ ,
A ⁱ² in the general formula (I-1) is a 1,3,4-phenylene group, a 1,3,5-phenylene group, a 1,3,4-cyclohexylene group, a 1,3,5-cyclohexylene group And a ring structure selected from pyridine-2,4,5-diyl group, pyridine-2,4,6-diyl group, pyrimidine-2,4,5-diyl group, pyrimidine-2,4,6-diyl group Wherein the ring structure is unsubstituted or 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, 1 to 1 carbon atoms. 12 halogenated alkoxy group, a halogen atom, a cyano group, a nitro group or a P ⁱ¹ -Sp ⁱ¹ - represents a group which may be substituted with, a compound according to claim 2 or 3. Z ⁱ¹ , Z ⁱ² and Z ^{i3 in the} general formula (i-1) each represent a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms or a linear chain having 2 to 18 carbon atoms. It represents Jo or branched alkenylene group, the alkylene group or the Arukeren -CH group ₂ - so that oxygen atoms are not directly adjacent are -O -, - COO -, - C (= O) -, - C ( = CH ₂₎ - or -OCO- may be replaced with a compound according to any one of claims 2-4. ^{6. Pi1} in the general formula (i-1) represents a substituent selected from the group represented by the following general formulas (P-1) to (P-14). The compound according to the above.

Formula (i) K ⁱ¹ and K ⁱ² according the general formula (K-1), (K -3), (K-11), according to claim 1 which is (K-15) or (K-17) 7. The compound according to any one of claims 6 to 6.   The compound represented by the general formula (i) according to any one of claims 1 to 7, and another polymerizable compound and a non-polymerizable liquid crystal compound different from the compound represented by the general formula (I). A liquid crystal composition containing As the polymerizable compound, general formula (P):

(Where
Z ^p1 is a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms in which a hydrogen atom may be substituted with a halogen atom, or a carbon atom in which a hydrogen atom may be substituted with a halogen atom. An alkoxy group having 1 to 15 carbon atoms, an alkenyl group having 1 to 15 carbon atoms where a hydrogen atom may be substituted with a halogen atom, an alkenyloxy having 1 to 15 carbon atoms optionally having a hydrogen atom substituted with a halogen atom A group or —Sp ^p2 —R ^p2 ;
R ^p1 and R ^p2 are represented by the following formulas ( ^RI ) to (R-VIII):

(Where
* Binds to Sp ^p1 ,
R ^{2 to} R ⁶ each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms,
W represents a single bond, -O- or a methylene group,
T represents a single bond or -COO-,
p, t and q each independently represent 0, 1 or 2. )
Represents one of
Sp ^p1 and Sp ^p2 represent a spacer group,
L ^p1 and L ^p2 each independently represent a single bond, —O—, —S—, —CH ₂ —, —OCH ₂ —, —CH ₂ O—, —CO—, —C ₂ H ₄ —, _{-COO -, - OCO -, -} OCOOCH 2 -, - CH 2 OCOO -, - OCH 2 CH 2 O -, - CO-NR a -, - NR a -CO -, - SCH 2 -, - CH 2 S ^{-, - CH = CR a -COO} -, - CH = CR a -OCO -, - COO-CR a = CH -, - OCO-CR a = CH -, - COO-CR a = CH-COO -, - ^{COO-CR a = CH-OCO} -, - OCO-CR a = CH-COO -, - OCO-CR a = CH-OCO -, - (CH 2) z -C (= O) -O -, - ( _{CH 2) z -O- (C =} O) -, - O- (C = O) - (CH 2) z -, - (C = O _{-O- (CH 2) z -,} - CH 2 (CH 3) C-C (= O) -O -, - CH 2 (CH 3) C-O- (C = O) -, - O- ( _{C = O) -C (CH 3} ) CH 2, - (C = O) -O-C (CH 3) -CH 2, -CH = CH -, - CF = CF -, - CF = CH -, - CH = CF—, —CF ₂ —, —CF ₂ O—, —OCF ₂ —, —CF ₂ CH ₂ —, —CH ₂ CF ₂ —, —CF ₂ CF ₂ — or —C≡C— , ^{R a} represents hydrogen atom or an alkyl group having a carbon number of 1 to 4 independently, z represents represents.) an integer of 1-4 ^{M p2} is 1,4-phenylene group, 1,4 -Cyclohexylene group, anthracene-2,6
-Diyl group, phenanthrene-2,7-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, indan-2,5-diyl group, 1 , 2,3,4-tetrahydronaphthalene-2,6-diyl group, 1,3-dioxane-
Represents a 2,5-diyl group or a single bond, and M ^p2 is unsubstituted or has 1 to 12 carbon atoms.
Alkyl group, halogenated alkyl group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, halogenated alkoxy group having 1 to 12 carbon atoms, halogen atom, cyano group, nitro group or -R ^p1 May be replaced by
M ^p1 is ^{calculated according} to the following formulas (i-11) to (ix-11):

(In the formula, * binds to Sp ^p1 and ** binds to L ^p1 , L ^p2 or Z ^p1 .)
Represents one of
M ^p3 is ^{calculated according} to the following formulas (i-13) to (ix-13):

(In the formula, * binds to Z ^p1 and ** binds to L ^p2 .)
Represents one of
m ^p2 ~m ^p4 are each independently 0, 1, 2 or 3,
^mp1 and ^mp5 each independently represent 1, 2 or 3,
Z ^p1 is or different even they are identical to each other when there are a plurality, in the case where R ^p1 there are a plurality or different even they are identical to each other, R ^p2 is more if present may be different even they are identical to each other, when Sp ^p1 there are a plurality or different even they are identical to each other, when Sp ^p2 there are multiple ^May be the same or different from each other, and when plural L ^p1 are present, they may be the same or different from each other. When plural M ^p2 are present, they are mutually different. They may be the same or different. )
The liquid crystal composition according to claim 8, comprising one or more compounds represented by the formula:   A liquid crystal display device in which at least one of the two substrates using the liquid crystal composition according to claim 8 has no alignment film.