Polymerizable liquid crystal composition, liquid crystal display element, and compound

Abstract

The subject of the present invention is to provide a polymerizable liquid crystal composition, which can achieve uniform vertical orientation of liquid crystal compounds even without a PI layer, can suppress the generation of drip marks and uneven orientation, has high stability of vertical orientation and pretilt angle, and excellent compatibility; and to provide a liquid crystal display element using the liquid crystal composition. In addition, another subject of the present invention is to provide a compound for making the above-mentioned liquid crystal composition possible. The present invention provides a polymerizable liquid crystal composition containing one or more compounds represented by general formula (i), a liquid crystal display element using the polymerizable liquid crystal composition, and a compound represented by general formula (i).

Description

Technical Field

[0001] The present invention relates to a polymerizable liquid crystal composition, a liquid crystal display element, and a compound. Background Art

[0002] Liquid crystal display elements represented by VA type, PSA type, and PSVA type are in the following manner: when no voltage is applied, a black display with vertical orientation is displayed, and on the other hand, a white display with uniformly tilted horizontal orientation is displayed when voltage is applied. In previous liquid crystal displays, in order to stably switch these black and white displays in pixels, it is currently necessary to set a special layer called a polyimide alignment film (hereinafter referred to as a PI layer) on the electrode. However, in recent years, panel manufacturers have studied various methods for achieving the orientation of liquid crystal molecules while omitting the PI layer due to the advantages of reducing the cost of film making of the PI layer, environmental considerations, and narrow frames.

[0003] As the above-mentioned method, there is a method of adding a spontaneous orientation additive to a liquid crystal composition. For example, Patent Document 1 discloses a liquid crystal medium having negative or positive dielectric constant anisotropy, comprising liquid crystal molecules and other components constituting the liquid crystal composition, i.e., low molecular weight components, and polymerizable components of self-orienting polymerizable mesogens (spontaneous orientation additives) having polar anchor groups. According to Patent Document 1, it is disclosed that: by containing the self-orienting polymerizable mesogens, the above-mentioned liquid crystal medium can achieve a homeotropic orientation of the LC medium on the surface or cell wall of a liquid crystal display (LC display), and an LC display having a homeotropic orientation of the LC medium without an orientation film can be obtained.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent Application Publication No. 2015-168826 Summary of the invention

[0007] Problems to be solved by the invention

[0008] In recent years, due to the pursuit of higher and finer visual recognition, large area, etc., the panel structure and various components have become complicated, and the vertical orientation of the liquid crystal composition has also been higher than before. Therefore, it is necessary to have a liquid crystal composition with high stability of vertical orientation in which drip marks and uneven orientation are suppressed compared with the past. In addition, in the process of forming a pre-tilt angle, when a voltage is applied, it is necessary to make the monomer in the polymerizable liquid crystal composition undergo polymerization reaction, but if the stability of the pre-tilt angle formed is low, afterimages will be generated when the panel is formed. Therefore, a liquid crystal composition with high stability of the pre-tilt angle is required.

[0009] However, the inventors have conducted in-depth research and found that the stability of the vertical orientation of the liquid crystal molecules and the stability of the pretilt angle deteriorate according to the number of polymerizable groups and polar groups of the spontaneous orientation additive added to the liquid crystal composition and the position of these groups in the molecular structure. In addition, the spontaneous orientation additive has a problem of reduced compatibility with hydrophobic liquid crystal molecules and easy precipitation from the polymerizable liquid crystal composition according to its structure.

[0010] Therefore, the object of the present invention is to provide a polymerizable liquid crystal composition, which can achieve uniform vertical alignment of liquid crystal compounds even without a PI layer, is not prone to drip marks and uneven orientation, has high long-term stability of vertical alignment and pretilt angle, and excellent compatibility; and to provide a liquid crystal display element using the liquid crystal composition. In addition, another subject of the present invention is to provide a compound for making the above-mentioned liquid crystal composition possible.

[0011] Methods for solving problems

[0012] As a result of intensive studies, the present inventors have found that a liquid crystal composition containing a compound represented by the general formula (i) having a desired structure as a spontaneous alignment additive can solve the above-mentioned problems, thereby completing the present invention.

[0013] That is, the present invention provides a polymerizable liquid crystal composition containing one or more compounds represented by general formula (i).

[0014] [Chemistry 1]

[0015]

[0016] (In general formula (i),

[0017] R i1 represents a hydrogen atom, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a straight-chain or branched alkyl halide group having 1 to 20 carbon atoms, wherein the -CH2- in the alkyl group or the alkyl halide group may be substituted by -CH=CH-, -C≡C- or -O-, but two or more -O- groups are not adjacent,

[0018] A i1 and A i2 Each independently represents a divalent aromatic group, a divalent cycloaliphatic group, a divalent heterocyclic compound group, a divalent condensed ring, or a divalent condensed polycyclic ring, and the hydrogen atoms in these ring structures may be replaced by L i1 Replacement, L i1represents a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkyl halide group having 1 to 20 carbon atoms, or a halogen atom, wherein the -CH2- in the alkyl group or alkyl halide group may be substituted by -CH=CH-, -C≡C-, or -O-, but two or more -O- groups are not adjacent,

[0019] Z i1 and Z i2 each independently represents a single bond, -O-, -CH=CH-, -CF=CF-, -C≡C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF2O-, -OCF2-, -CH=CHCOO-, -OCOCH=CH-, -CH=C(CH3)COO-, -OCOC(CH3)=CH-, -CH2-CH(CH3)COO-, -OCOCH(CH3)-CH2-, -OCH2CH2O-, or an alkylene group having 1 to 10 carbon atoms, in which one or two or more non-adjacent -CH2- groups in the alkylene group may be substituted with -O-, -COO- or -OCO-,

[0020] R i2 , R i3 and R i4 each independently represents a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched halogenated alkyl group having 1 to 20 carbon atoms, or X i4 The -CH2- in the alkyl or alkyl halide may be substituted by -CH=CH-, -C≡C- or -O-, but two or more -O- are not adjacent.

[0021] X i1 , X i2 , X i3 and X i4 Represented independently -Sp i1 -P i1 or -Sp i2 -K i1 ,

[0022] K i1 Each independently represents the general formula (K-1) or (K-2),

[0023] [Chemistry 2]

[0024]

[0025] (where black dots represent bonding bonds),

[0026] T k1 Each independently represents a group represented by general formula (T-1) to (T-7),

[0027] [Chemistry 3]

[0028]

[0029] S T1 each independently 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, wherein the -CH2- of the alkylene group or the alkenylene group may be substituted by -O-, -COO-, -C(=O)-, or -OCO- in a manner that the oxygen atom is not directly adjacent thereto,

[0030] R T1 Each independently represents an alkyl group having 1 to 5 carbon atoms, wherein the -CH2- of the alkyl group may be substituted by -O-, -COO-, -C(=O)- or -OCO- in a manner that the oxygen atom is not directly adjacent thereto,

[0031] R T2 and R T3 Each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R k1 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, wherein one or two or more non-adjacent -CH2- groups in the alkyl group may be substituted with -O-,

[0032] T k2 Each independently represents a group represented by general formula (T-8) to (T-17),

[0033] [Chemistry 4]

[0034]

[0035] (where black dots represent bonding bonds),

[0036] X K1 and Y K1 each independently represents -CH2-, an oxygen atom or a sulfur atom,

[0037] Z K1 each independently represents an oxygen atom or a sulfur atom,

[0038] W K1 , U K1 、V K1 and S K1 Each independently represents a methine or a nitrogen atom. Here, the hydrogen atom in the group represented by the general formula (T-8) to (T-17) may be replaced by -Sp i5 -P i3 replace,

[0039] Sp i1 、Sp i2 、Sp i3 、Sp i4and Sp i5 Each independently represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, or a linear or branched alkylene group having 1 to 20 carbon atoms, wherein two -O- in the alkylene group or alkylene group may be substituted with -CH=CH-, -C≡C- or -O- in a non-adjacent manner,

[0040] P i1 , P i2 and P i3 are independently represented by general formulas (P-1) to (P-16),

[0041] [Chemistry 5]

[0042]

[0043] (where black dots represent bonding bonds),

[0044] In the presence of multiple P i1 , P i2 , P i3 、Sp i1 、Sp i2 、Sp i3 、Sp i4 、Sp i5 , A i1 , A i2 , Z i1 , Z i2 , X i1 , X i4 , K i1 , T k1 , T k2 , R k1 , ni1, ki1, ki2, ki3, they may be the same or different, mi1 and mi2 each independently represent an integer of 1 to 4,

[0045] ni1 represents an integer from 0 to 2. When ni1 represents an integer of 1 or 2, A i2 One or two hydrogen atoms in the ring structure are replaced by X i1 replace,

[0046] ki1, ki2 and ki3 each independently represent an integer from 0 to 3, wherein the total of ki1, ki2 and ki3 is 3.

[0047] Here, in the general formula (i), one or more selected from P i1 , P i2 and P i3 The group consisting of, and containing one or more selected from T k1 and T k2 The bases in the group consisting of, and, are selected from P i1, P i2 , P i3 , T k1 and T k2 The total number of bases in the composed groups is 5 or more).

[0048] The present invention also provides a liquid crystal display element comprising two substrates and a resin component formed by curing the compound represented by the general formula (i) in the polymerizable liquid crystal composition between the two substrates.

[0049] In addition, the present invention provides a compound represented by the above general formula (i).

[0050] Effects of the Invention

[0051] The polymerizable liquid crystal composition of the present invention has the following effects: even without providing a PI layer, the liquid crystal compound can be uniformly vertically aligned, drip marks and uneven alignment are unlikely to occur, the vertical alignment and pretilt angle have high long-term stability, and the compatibility is excellent.

[0052] In addition, the liquid crystal display element of the present invention has the following effects: the liquid crystal molecules can be uniformly oriented vertically without drip marks or uneven orientation, or drip marks and uneven orientation can be reduced to an acceptable level, screen burn-in is unlikely to occur, and the element has excellent long-term display characteristics.

[0053] Furthermore, the compound of the present invention has a desired structure represented by the general formula (i), and thus has the effect of having good compatibility with a liquid crystal composition, and can uniformly align liquid crystal molecules in the liquid crystal composition vertically and impart a stable pretilt angle. BRIEF DESCRIPTION OF THE DRAWINGS

[0054] Figure 1 It is a figure explaining the dropping position in the vertical orientation evaluation test. DETAILED DESCRIPTION

[0055] I. Polymerizable Liquid Crystal Composition

[0056] The polymerizable liquid crystal composition of one embodiment of the present invention (hereinafter referred to as the polymerizable liquid crystal composition of the present invention) contains one or more compounds represented by general formula (i). In addition, the compound represented by general formula (i) is sometimes referred to as compound (i) or compound of formula (i).

[0057] [Chemistry 6]

[0058]

[0059] (In general formula (i),

[0060] R i1represents a hydrogen atom, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a straight-chain or branched alkyl halide group having 1 to 20 carbon atoms, wherein the -CH2- in the alkyl group or alkyl halide group may be substituted by -CH=CH-, -C≡C- or -O-, but two or more -O- groups are not adjacent,

[0061] A i1 and A i2 Each independently represents a divalent aromatic group, a divalent cycloaliphatic group, a divalent heterocyclic compound group, a divalent condensed ring, or a divalent condensed polycyclic ring, and the hydrogen atoms in these ring structures may be replaced by L i1 Replacement, L i1 represents a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkyl halide group having 1 to 20 carbon atoms, or a halogen atom, wherein the -CH2- in the alkyl group or alkyl halide group may be substituted by -CH=CH-, -C≡C-, or -O-, but two or more -O- groups are not adjacent,

[0062] Z i1 and Z i2 each independently represents a single bond, -O-, -CH=CH-, -CF=CF-, -C≡C-, -COO-, -OCO-, -OCOO-, -OOCO-, -CF2O-, -OCF2-, -CH=CHCOO-, -OCOCH=CH-, -CH=C(CH3)COO-, -OCOC(CH3)=CH-, -CH2-CH(CH3)COO-, -OCOCH(CH3)-CH2-, -OCH2CH2O-, or an alkylene group having 1 to 10 carbon atoms, in which one or two or more non-adjacent -CH2- groups in the alkylene group may be substituted with -O-, -COO- or -OCO-,

[0063] R i2 , R i3 and R i4 each independently represents a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched halogenated alkyl group having 1 to 20 carbon atoms, or X i4 The -CH2- in the alkyl or alkyl halide may be substituted by -CH=CH-, -C≡C- or -O-, but two or more -O- are not adjacent.

[0064] X i1 , X i2 , X i3 and X i4 Represented independently -Sp i1 -P i1 or -Sp i2 -K i1 ,

[0065] Ki1 Each independently represents the general formula (K-1) or (K-2),

[0066] [Chemistry 7]

[0067]

[0068] (where black dots represent bonding bonds),

[0069] T k1 Each independently represents a group represented by general formula (T-1) to (T-7),

[0070] [Chemistry 8]

[0071]

[0072] S T1 each independently 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, wherein the -CH2- of the alkylene group or the alkenylene group may be substituted by -O-, -COO-, -C(=O)-, or -OCO- in a manner that the oxygen atom is not directly adjacent thereto,

[0073] R T1 Each independently represents an alkyl group having 1 to 5 carbon atoms, wherein the -CH2- of the alkyl group may be substituted by -O-, -COO-, -C(=O)- or -OCO- in a manner that the oxygen atom is not directly adjacent thereto,

[0074] R T2 and R T3 Each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R k1 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, wherein one or two or more non-adjacent -CH2- groups in the alkyl group may be substituted with -O-,

[0075] T k2 Each independently represents a group represented by general formula (T-8) to (T-17),

[0076] [Chemistry 9]

[0077]

[0078] (where black dots represent bonding bonds),

[0079] X K1 and Y K1 each independently represents -CH2-, an oxygen atom or a sulfur atom,

[0080] Z K1 each independently represents an oxygen atom or a sulfur atom,

[0081] W K1 , U K1 、V K1 and S K1 Each independently represents a methine or a nitrogen atom. Here, the hydrogen atom in the group represented by the general formula (T-8) to (T-17) may be replaced by -Sp i5 -P i3 replace,

[0082] Sp i1 、Sp i2 、Sp i3 、Sp i4 and Sp i5 Each independently represents a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, or a linear or branched alkylene group having 1 to 20 carbon atoms, wherein two -O- in the alkylene group or alkylene group may be substituted with -CH=CH-, -C≡C- or -O- in a non-adjacent manner,

[0083] P i1 , P i2 and P i3 are independently represented by general formulas (P-1) to (P-16),

[0084] [Chemistry 10]

[0085]

[0086] (where black dots represent bonding bonds),

[0087] In the presence of multiple P i1 , P i2 , P i3 、Sp i1 、Sp i2 、Sp i3 、Sp i4 、Sp i5 , A i1 , A i2 , Z i1 , Z i2 , X i1 , X i4 , K i1 , T k1 , T k2 , R k1 , ni1, ki1, ki2, ki3, they may be the same or different, mi1 and mi2 each independently represent an integer of 1 to 4,

[0088] ni1 represents an integer from 0 to 2. When ni1 represents an integer of 1 or 2, A i2 One or two hydrogen atoms in the ring structure are replaced by Xi1 replace,

[0089] ki1, ki2 and ki3 each independently represent an integer from 0 to 3, wherein the total of ki1, ki2 and ki3 is 3.

[0090] Here, in the general formula (i), one or more selected from P i1 , P i2 and P i3 The group consisting of: and containing one or more selected from T k1 and T k2 The bases in the group consisting of, and, selected from P i1 , P i2 , P i3 , T k1 and T k2 The total number of bases in the composed groups is 5 or more).

[0091] Here, in this specification, a polymerizable liquid crystal composition refers to: a composition containing one or more polymerizable compounds having a polymerizable group, and a liquid crystal composition, wherein the liquid crystal composition contains one or more non-polymerizable liquid crystal compounds (liquid crystal materials). In the polymerizable liquid crystal composition of the present invention, the compound represented by the general formula (i) is equivalent to a polymerizable compound because it has a polymerizable group. In addition, the compound represented by the general formula (i) has a mesogen skeleton composed of a plurality of ring structures, and the mesogen skeleton has a polymerizable group and a polar group separated by a spacer, and functions as a spontaneous orientation additive.

[0092] The polymerizable liquid crystal composition of the present invention is characterized in that: the compound represented by the general formula (i) contains one or more selected from P i1 , P i2 and P i3 The group consisting of, and containing one or more selected from T k1 and T k2 The bases in the group consisting of, and, selected from P i1 , P i2 , P i3 , T k1 and T k2 The total number of bases in the composed groups is 5 or more.

[0093] Here, choose P i1 , P i2 and P i3 The group consisting of represents a polymerizable group, and has the function of causing the polymer to be formed preferentially at the interface in the liquid crystal display element by external stimulation such as heat or light. k1 and T k2The group consisting of is a polar group, which imparts vertical alignment to the liquid crystal molecules by adsorbing on the substrate interface in a liquid crystal display element. The compound represented by general formula (i) is selected from P i1 , P i2 , P i3 , T k1 and T k2 The total number of bases in the composed group (hereinafter, sometimes referred to as the total number of polymerizable groups and polar groups) is 5 or more. Compared with the case of 4 or less, when the polymerizable liquid crystal composition is sealed in the panel, the probability of being initially adsorbed by the substrate increases dramatically, and good vertical orientation can be maintained. Among them, as in compound (i), when the polar groups in other molecules are asymmetrically adjacent on one side of the molecule, other polar groups can be adsorbed with the substrate in more places through thermal motion, so the result can maintain good vertical orientation. It should be noted here that in compound (i), although the polymerizable group is not as strong as the polar group, it functions as an auxiliary to orientation.

[0094] In addition, the polymerizable liquid crystal composition of the present invention is characterized in that the compound represented by the general formula (i) has a compound selected from P at a desired position in the general formula (i). i1 , P i2 , P i3 , T k1 and T k2 In particular, the compound represented by general formula (i) has at least X on one side of the long axis of the molecule (in detail, on the endmost benzene ring on one side of the long axis) in its molecular structure. i2 and X i3 Here, X i2 and X i3 Because it contains P i1 , P i2 and P i3 and T k1 and T k2 The partial structure represented by the general formula (i) has polarity, so as mentioned above, it can be adsorbed on the substrate in multiple places. Therefore, it can be inferred that in the liquid crystal display element using the polymerizable liquid crystal composition of the present invention, the compound represented by the general formula (i) can be adsorbed on the substrate holding the liquid crystal composition (liquid crystal layer) with appropriate strength. In addition, it is believed that the compound represented by the general formula (i) has T at the end. k1 and T k2The partial structure represented by the general formula (i) can therefore be maintained in a state where the liquid crystal molecules are oriented in a vertical direction. Therefore, by the polymerizable liquid crystal composition of the present invention, even if the PI layer is not provided, the liquid crystal molecules can be uniformly and vertically oriented (when no voltage is applied, the vertical orientation of the liquid crystal molecules is induced, and when a voltage is applied, the horizontal orientation of the liquid crystal molecules is achieved). Thus, the compound represented by the general formula (i) has the function of helping the vertical orientation of the liquid crystal molecules in the liquid crystal composition.

[0095] In addition, the inventors found that the compound represented by the general formula (i) has the above-mentioned characteristic structure, and the polymerizable liquid crystal composition of the present invention has high compatibility with the compound represented by the general formula (i) and the liquid crystal composition, and can ensure low temperature stability. The reason is uncertain, but it is speculated that the bending of the entire molecule is relatively improved by combining the polymerizable group and the alkyl group from the linear direction and the side direction of the mesogen, thereby playing a role in hindering the crystallization coating.

[0096] Therefore, the polymerizable liquid crystal composition of the present invention contains a compound represented by general formula (i), and even without setting a PI layer, the liquid crystal compound can be uniformly vertically oriented, and it is not easy to produce drip marks and uneven orientation. The long-term stability of the vertical orientation and pretilt angle is high, and it shows excellent solubility.

[0097] Hereinafter, the compound contained in the polymerizable liquid crystal composition of the present invention will be described in detail.

[0098] A. Compounds represented by general formula (i)

[0099] In the present invention, the compound represented by the general formula (i) is a polymerizable compound and is a compound having a function of spontaneously aligning liquid crystal molecules (spontaneous aligning additive).

[0100] From the above viewpoints, the compound represented by the general formula (i) is selected from the group consisting of P i1 , P i2 , P i3 , T k1 and T k2 The total number of groups in the group is 5 or more, and one end of the molecular structure in the long axis direction, preferably one end of the molecular main chain, has P i1 , P i2 and P i3 and T k1 and T k2 Any partial structure represented by any one of the above may be used, and the chemical structure of the binding partner to which the partial structure is bound is not particularly limited as long as it does not inhibit the function of the liquid crystal composition.

[0101] In the general formula (i), selected from P i1 , P i2 , Pi3 , T k1 and T k2 The total number of the groups of the composed groups may be 5 or more, but the more the number of polymerizable groups and polar groups is, the better the orientation and pretilt angle stability are, so it is preferably 5 or more, or 6 or more. On the other hand, from the viewpoint of synthesis cost and ensuring crystallinity, the total number of the above groups is preferably 8 or less, or 7 or less.

[0102] In the general formula (i), P i1 , P i2 and P i3 The number of groups in the group is 1 or more, preferably 3 or more, and particularly preferably 4 or more. In addition, the number of the above groups is preferably 6 or less, more preferably 5 or less. The reason is that: by making the selected group P i1 , P i2 and P i3 When the number of bases in the composed group is within the above range, the pretilt angle stability (IS) becomes good.

[0103] In the general formula (i), selected from T k1 and T k2 The number of groups in the group is 1 or more, preferably 3 or more, and particularly preferably 4 or more. In addition, the number of the above groups is preferably 7 or less, and more preferably 6 or less. This is because: by making the selected group T k1 and T k2 When the number of groups in the composed group is within the above range, the vertical alignment of the liquid crystal molecules can be improved.

[0104] R in the general formula (i) i1 Preferably, it is a linear or branched alkyl group having 1 to 18 carbon atoms, and more preferably a linear or branched alkyl group having 3 to 18 carbon atoms. The -CH2- in the alkyl group may be substituted by -CH=CH-, -C≡C- or -O-. However, two or more -O- are not adjacent. From the viewpoint of improving the orientation of the liquid crystal compound, R i1 The number of carbon atoms in is preferably 3 or more, preferably 4 or more, and preferably 5 or more. i1 The polymerizable group is not included.

[0105] Z in the general formula (i) i1 and Z i2Each of them independently preferably represents a single bond, -CH=CH-, -CF=CF-, -C≡C-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH=CHCOO-, -OCOCH=CH-, -OCH2CH2O-, or an alkylene group having 1 to 10 carbon atoms, or a group in which one or two or more non-adjacent -CH2- in the alkylene group are substituted with -O-, -COO- or -OCO-. More preferably, Z i1 and Z i2 Each independently represents a single bond, -COO-, -OCO-, -CH=CHCOO-, -OCOCH=CH-, -OCH2CH2O-, a linear or branched alkylene group having 1 to 6 carbon atoms, or a group in which one or two or more non-adjacent -CH2- groups in the alkylene group are substituted with -O-, -COO- or -OCO-. More preferably, Z i1 and Z i2 Each independently represents a single bond, -COO-, -OCO-, -OCH2CH2O-, an alkylene group having 2 carbon atoms (ethylene (-CH2CH2-)), a group in which one -CH2- in an ethylene group is substituted by -O- (-CH2O-, -OCH2-), or a group in which one -CH2- in an ethylene group is substituted by -COO- or -OCO-.

[0106] A in the general formula (i) i1 and A i2 Each independently is preferably a divalent cyclic aromatic group, a divalent cyclic heteroaromatic group, a divalent cyclic aliphatic group, or a divalent cyclic heteroaliphatic group, and more preferably a divalent 6-membered cyclic aromatic group, a divalent 6-membered cyclic heteroaromatic group, a divalent 6-membered cyclic aliphatic group, a divalent 6-membered cyclic heteroaliphatic group, a divalent 5-membered cyclic aromatic group, a divalent 5-membered cyclic heteroaromatic group, a divalent 5-membered cyclic aliphatic group, or a divalent 5-membered cyclic heteroaliphatic group. In addition, the hydrogen atoms in these ring structures may be replaced by L i1 replace.

[0107] Specifically, A i1 and A i2 Preferably, it is 1,4-phenylene, 1,4-cyclohexylene, anthracene-2,6-diyl, phenanthrene-2,7-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, indane-2,5-diyl, chroman-3,7-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or 1,3-dioxane-2,5-diyl, and the ring structure in these groups is preferably unsubstituted or the hydrogen atoms are replaced by L i1 replace.

[0108] L i1Preferably, it is an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, or a halogen atom, and more preferably, it is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom. Examples of the halogen atom include a fluorine atom and a chlorine atom, among which a fluorine atom is preferred. The alkyl group, the halogenated alkyl group, and the alkoxy group may be linear or branched.

[0109] Preferably A i1 represents a divalent unsubstituted 6-membered aromatic group, a divalent unsubstituted 6-membered aliphatic group, or a group in which the hydrogen atoms in these ring structures are substituted by an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, or a halogen atom. More preferably, A i1 It means that the hydrogen atoms in the ring structure may be substituted by an alkyl group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom in a 1,4-phenylene group, a 2,6-naphthyl group, or a 1,4-cyclohexylene group. The halogen atom is preferably a fluorine atom.

[0110] A i2 Preferably, it represents 1,4-phenylene.

[0111] A i2 At least one hydrogen atom in the ring structure may also be replaced by X i1 Replace. X i1 The number of ni1, that is, ni1 in the general formula (i) represents an integer of 0 to 2, and is preferably an integer of 1 to 2, and more preferably 1, from the perspective of low-temperature storage stability and orientation. i2 The hydrogen atoms in the ring structure are not i1 When n1 represents an integer of 1 or 2, A i2 One or two hydrogen atoms in the ring structure are replaced by X i1 Replace. i2 The multiple hydrogen atoms in the ring structure are replaced by X i1 When replacing, multiple X i1 Can be the same or different.

[0112] In A i2 At least one hydrogen atom in the ring structure is replaced by X i1 When replacing, in A i2 In the ring structure of i1 The position of is not particularly limited, wherein A in the above case i2 Preferably, the following formula (A i2 -1) to (A i2 -4) is indicated by any one of the following.

[0113] [Chemistry 11]

[0114]

[0115] (The above formula (A i2 -1) to (A i2 -4), a black dot indicates the i1 The two black dots represent the bond with Z i2 The combination key, 2 X i1 can be the same or different).

[0116] R in the general formula (i) i2 , R i3 and R i4 Each of X is independently preferably a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, or i4 , more preferably a hydrogen atom, a halogen atom, a linear or branched alkyl group having 3 to 18 carbon atoms, or X i4 The -CH2- in the alkyl group may be substituted by -CH=CH-, -C≡C- or -O-, wherein two or more -O- are not adjacent.

[0117] R i2 , R i3 and R i4 When each of R and R is independently an alkyl group, from the viewpoint of improving the alignment of the liquid crystal compound, i2 , R i3 and R i4 The number of carbon atoms in is preferably 3 or more, preferably 4 or more, and preferably 5 or more.

[0118] X in the general formula (i) i1 , X i2 , X i3 and X i4 Represented independently -Sp i1 -P i1 or -Sp i2 -K i1 In addition, K i1 Each of the above general formula (K-1) or (K-2) is independently represented by the above general formula (K-1) or (K-2). i1 and X i4 They may be the same or different.

[0119] X i2 and X i3 , and R i2 , R i3 and R i4 is a group that replaces a hydrogen atom in the ring structure of a benzene ring. i2 and X i3, and R i2 , R i3 and R i4 The position of is not particularly limited, for example, it can be the following formula (A i3 -1) to (A i3 -6) is the position of any one of the above.

[0120] [Chemistry 12]

[0121]

[0122] (* in the formula indicates that Z i2 binding site).

[0123] In addition, in R i4 Represents X i4 When, that is, at R i4 Indicates - Sp i1 -P i1 or -Sp i2 -K i1 When X i2 , X i3 and X i4 , and R i2 and R i2 The position of is not particularly limited, but is preferably the following formula (A i3 -1-1) or (A i3 -3-1) indicates.

[0124] [Chemistry 13]

[0125]

[0126] (* in the formula indicates that Z i2 binding site).

[0127] T in the general formula (K-1) k1 Each independently represents a group represented by the above-mentioned general formulae (T-1) to (T-7), and among them, a group represented by general formula (T-1), (T-3), (T-4) or (T-7) is preferred.

[0128] S in the general formula (T-3) and (T-7) T1 Each independently preferably represents a single bond, a linear or branched alkylene group having 1 to 10 carbon atoms, or a linear or branched alkenylene group having 2 to 10 carbon atoms, preferably a linear or branched alkylene group having 1 to 7 carbon atoms, or a linear or branched alkenylene group having 2 to 7 carbon atoms, and preferably a linear alkylene group having 1 to 3 carbon atoms. In addition, -CH2- in the alkylene group or alkenylene group may be substituted by -O-, -COO-, -C(=O)-, or -OCO- in a manner that the oxygen atom is not directly adjacent.

[0129] R in the general formula (T-3) T1 Each independently represents an alkyl group having 1 to 5 carbon atoms. The alkyl group is linear or branched. The -CH2- of the alkyl group may be substituted by -O-, -COO-, -C(=O)- or -OCO- in a manner that the oxygen atom is not directly adjacent. T1 It is preferably a linear alkyl group having 1 to 3 carbon atoms. In the general formula (T-3), it is preferred that at least two or more secondary carbon atoms contain -C(=O).

[0130] R in the general formula (T-6) T2 and R T3 Each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and among them, preferably represents a hydrogen atom.

[0131] In the general formula (K-1), R k1 Each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, wherein one or two or more non-adjacent -CH2- groups in the alkyl group may be substituted by -O-, and is more preferably a hydrogen atom or a linear alkyl group having 1 to 3 carbon atoms.

[0132] In the general formula (K-1), ki1, ki2 and ki3 each independently represent an integer of 0 to 3, wherein the total of ki1, ki2 and ki3 is 3. From the viewpoint of improving the orientation of the liquid crystal and the solubility of the liquid crystal compound, ki1 is preferably an integer representing 1 or 2. ki2 is preferably an integer representing 1 or 2, and from the viewpoint of improving the orientation, it is more preferably an integer representing 1. ki3 is preferably an integer representing 0 or 1.

[0133] Such combinations of ki1, ki2 and ki3 can be appropriately selected. Preferred combinations include, for example, combination A in which ki1 represents an integer of 1, ki2 represents an integer of 2, and ki3 represents an integer of 0, combination B in which ki1 represents an integer of 2, ki2 represents an integer of 1, and ki3 represents an integer of 0, combination C in which ki1 represents an integer of 2, ki2 represents an integer of 0, and ki3 represents an integer of 1, and the like.

[0134] Here, in the partial structure represented by the general formula (K-1), the polar group T k1 With P as a polymerizing group i2 Therefore, regarding the combination of ki1, ki2 and ki3, when the orientation of the liquid crystal is emphasized, the combination A is preferred, and on the other hand, when the solubility in the liquid crystal composition is emphasized, the combination C is preferred.

[0135] Preferred examples of the general formula (K-1) include the following general formulas (K-1-1) to (K-1-5). Among them, general formula (K-1-1), (K-1-3) or (K-1-4) is more preferred.

[0136] [Chemistry 14]

[0137]

[0138] (In the above general formulas (K-1-1) to (K-1-5), a plurality of T K1 Can be the same or different)

[0139] More specifically, the following general formulae (K-1-1A) to (K-1-4G) are exemplified as general formula (K-1-1A).

[0140] [Chemistry 15]

[0141]

[0142] [Chemistry 16]

[0143]

[0144] [Chemistry 17]

[0145]

[0146] [Chemistry 18]

[0147]

[0148] (In the above general formulas (K-1-1A) to (K-1-4G), R T4 , R T5 and R T6 Each independently represents an alkyl group having 1 to 3 carbon atoms, n T1 and n T2 Each independently represents 0 or 1, n T2 Each independently represents an integer of 1 to 3, and a plurality of R T4 , R T5 , R T6 、n T1 、n T2 and n T3 They can be the same or different)

[0149] T in the general formula (K-2) k2Each independently represents a group represented by the above-mentioned general formulae (T-8) to (T-17). Preferred examples of general formulae (T-8) to (T-17) include the following formulae (T-8-1) to (T-17-1). Among them, from the perspective of orientation and reactivity, preferred are formulae (T-8-1), (T-8-3), (T-10-1), (T-13-1), (T-15-1) and (T-18-1), and particularly preferred are formulae (T-8-1), (T-10-1) and (T-13-1).

[0150] [Chemistry 19]

[0151]

[0152] (In the formula, the black dots represent bonding bonds).

[0153] In the general formula (i), Sp i1 、Sp i2 、Sp i3 、Sp i4 and Sp i5 Preferably, it represents a linear or branched alkylene group having 1 to 20 carbon atoms or a linear or branched alkylene group having 1 to 20 carbon atoms, wherein two non-adjacent -O- in the -CH2- may be replaced by -CH=CH-, -C≡C- or -O-. Among them, Sp is preferably i1 、Sp i2 、Sp i3 、Sp i4 and Sp i5 At least one of the alkylene groups is an alkylene group having 1 to 18 carbon atoms, more preferably an alkylene group having 2 to 15 carbon atoms, and even more preferably an alkylene group having 2 to 8 carbon atoms. i1 and Sp i2 The reason for this is that the solubility in the liquid crystal composition is improved.

[0154] Due to K i1 When any of the above general formulas (K-1-3), (K-1-4) or (K-1-5) is represented, the crystallinity of the compound and the formation of a pretilt angle when forming a liquid crystal display element are improved, so Sp i1 、Sp i2 、Sp i3 、Sp i4 and Sp i5 At least one of may also represent a single bond.

[0155] In the general formula (i), P i1 , P i2 and P i3Each independently represents a group selected from the group represented by the above general formula (P-1) to the general formula (P-16), among which P is preferably i1 , P i2 and P i3 Preferably, each independently is a methacrylate group or an acrylate group, and specifically, a group represented by the general formula (P-1) or (P-2) is particularly preferred.

[0156] In the general formula (i), mi1 and mi2 each independently represent an integer of 1 to 4, preferably an integer of 1 to 2, and more preferably an integer of 1. In detail, from the viewpoint of the balance between the orientation and the low-temperature solution stability, mi1 is preferably an integer of 1 to 3, further preferably an integer of 1 to 2, and more preferably an integer of 1. On the other hand, from the viewpoint of the balance between the orientation and the pretilt angle stability, mi2 is preferably an integer of 1 to 2, and particularly preferably an integer of 1.

[0157] The compound represented by the general formula (i) is preferably a compound represented by the following general formula (i-A).

[0158] [Chemistry 20]

[0159]

[0160] (In the general formula (i-A), R i1 , A i1 , A i2 , Z i1 , Z i2 , X i1 , X i2 , X i3 , X i4 , mi1, mi2 and ni1 respectively represent the R i1 , A i1 , A i2 , Z i1 , Z i2 , X i1 , X i2 , X i3 , X i4 , mi1, mi2 and ni1 have the same meaning).

[0161] In the general formula (i-A), R i2 and R i3 Each of them independently preferably represents a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a linear or branched alkyl halide having 1 to 20 carbon atoms. In addition, the -CH2- in the alkyl group or alkyl halide may be substituted by -CH=CH-, -C≡C- or -O-, but two or more -O- are not adjacent.

[0162] The compound represented by the general formula (i-A) must have a hydrogen atom at a specific position in the ring structure on one side in the long axis direction (specifically, in the benzene ring located on one side in the long axis direction) in its molecular structure represented by -Sp i1 -P i1 or -Sp i2 -K i1 The basis (i.e. X i2 , X i3 and X i4 Thus, by having a characteristic structure in which the polar group and / or the polymerizable group is biased on one side of the long axis direction, the effect of the polymerizable liquid crystal composition containing the compound represented by the general formula (i) can be further easily exerted.

[0163] X in the general formula (i-A) i2 , X i3 and X i4 They may be the same or different.

[0164] Examples of the compound represented by the general formula (i-A) include compounds represented by any one of the following general formulae (i-A-1) to (i-A-4).

[0165] [Chemistry 21]

[0166]

[0167] (In the above, R i1 , A i1 , A i2 , Z i1 , Z i2 、mi1、Sp i3 and Sp i4 Respectively represent R in the general formula (i) i1 , A i1 , A i2 , Z i1 , Z i2 、mi1、Sp i3 and Sp i4 Same meaning).

[0168] As more specific examples of the compound represented by the general formula (i), compounds represented by the following formulae (i-1) to (i-660) are listed below, but the specific examples of the compound represented by the general formula (i) are not limited thereto.

[0169] [Chemistry 22]

[0170]

[0171] [Chemistry 23]

[0172]

[0173] [Chemistry 24]

[0174]

[0175] [Chemistry 25]

[0176]

[0177] [Chemistry 26]

[0178]

[0179] [Chemistry 27]

[0180]

[0181] [Chemistry 28]

[0182]

[0183] [Chemistry 29]

[0184]

[0185] [Chemistry 30]

[0186]

[0187] [Chemistry 31]

[0188]

[0189] [Chemistry 32]

[0190]

[0191] [Chemistry 33]

[0192]

[0193] [Chemistry 34]

[0194]

[0195] [Chemistry 35]

[0196]

[0197] [Chemistry 36]

[0198]

[0199] [Chemistry 37]

[0200]

[0201] [Chemistry 38]

[0202]

[0203] [Chemistry 39]

[0204]

[0205] [Chemistry 40]

[0206]

[0207] [Chemistry 41]

[0208]

[0209] [Chemistry 42]

[0210]

[0211] [Chemistry 43]

[0212]

[0213] [Chemistry 44]

[0214]

[0215] [Chemistry 45]

[0216]

[0217] [Chemistry 46]

[0218]

[0219] [Chemistry 47]

[0220]

[0221] [Chemistry 48]

[0222]

[0223] [Chemistry 49]

[0224]

[0225] [Chemistry 50]

[0226]

[0227] [Chemistry 51]

[0228]

[0229] [Chemistry 52]

[0230]

[0231] [Chemistry 53]

[0232]

[0233] [Chemistry 54]

[0234]

[0235] [Chemistry 55]

[0236]

[0237] [Chemistry 56]

[0238]

[0239] [Chemistry 57]

[0240]

[0241] [Chemistry 58]

[0242]

[0243] [Chemistry 59]

[0244]

[0245] [Chemistry 60]

[0246]

[0247] [Chemistry 61]

[0248]

[0249] [Chemistry 62]

[0250]

[0251] [Chemistry 63]

[0252]

[0253] [Chemistry 64]

[0254]

[0255] [Chemistry 65]

[0256]

[0257] [Chemistry 66]

[0258]

[0259] [Chemistry 67]

[0260]

[0261] [Chemistry 68]

[0262]

[0263] [Chemistry 69]

[0264]

[0265] [Chemistry 70]

[0266]

[0267] [Chemistry 71]

[0268]

[0269] [Chemistry 72]

[0270]

[0271] [Chemistry 73]

[0272]

[0273] [Chemistry 74]

[0274]

[0275] [Chemistry 75]

[0276]

[0277] [Chemistry 76]

[0278]

[0279] [Chemistry 77]

[0280]

[0281] [Chemistry 78]

[0282]

[0283] [Chemistry 79]

[0284]

[0285] [Chemistry 80]

[0286]

[0287] [Chemistry 81]

[0288]

[0289] [Chemistry 82]

[0290]

[0291] [Chemistry 83]

[0292]

[0293] [Chemistry 84]

[0294]

[0295] [Chemistry 85]

[0296]

[0297] [Chemistry 86]

[0298]

[0299] [Chemistry 87]

[0300]

[0301] The content of the compound represented by the general formula (i) in the polymerizable liquid crystal composition of the present invention is preferably 0.01 to 50% by mass, and from the viewpoint of more appropriately aligning the liquid crystal molecules, its lower limit is preferably 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 based on the total amount of the polymerizable liquid crystal composition. From the viewpoint of excellent response characteristics, the upper limit of the content of compound (i) is preferably 50% by mass or less, 30% by mass or less, 10% by mass or less, 7% by mass or less, 5% by mass or less, 4% by mass or less, or 3% by mass or less based on the total amount of the polymerizable liquid crystal composition.

[0302] B. Liquid Crystal Composition

[0303] The polymerizable liquid crystal composition of the present invention contains a liquid crystal composition in addition to the compound represented by the general formula (i). The liquid crystal composition contains one or more non-polymerizable liquid crystal compounds (liquid crystal molecules) in its composition. That is, the polymerizable liquid crystal composition of the present invention contains a non-polymerizable liquid crystal compound in addition to the compound represented by the general formula (i). The liquid crystal composition and the polymerizable liquid crystal composition of the present invention containing the liquid crystal composition preferably have a negative dielectric anisotropy (Δε). Negative dielectric anisotropy (Δε) means that the sign of Δε is negative and its absolute value is greater than 2. The polymerizable liquid crystal composition of the present invention preferably has a Δε in the range of -4.0 to -2.0 at 20°C, further preferably in the range of -3.5 to -2.3, and particularly preferably in the range of -3.3 to -2.5.

[0304] The liquid crystal composition may contain a compound selected from the group consisting of compounds represented by any one of General Formulae (N-1), (N-2) and (N-3) as a non-polymerizable liquid crystal compound.

[0305] [Chemistry 88]

[0306]

[0307] (In the general formulas (N-1), (N-2) and (N-3), R N11 , R N12 , R N21 , R N22 , R N31 and R N32 Each independently represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent -CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-,

[0308] A N11 , A N12 , A N21 , A N22 , A N31 and A N32 each independently represents a group selected from the group consisting of the radical (a), the radical (b), the radical (c) and the radical (d),

[0309] (a) 1,4-cyclohexylene (one -CH2- or two or more non-adjacent -CH2- in the group may be substituted by -O-),

[0310] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in the group may be substituted with -N=),

[0311] (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=), and

[0312] (d) 1,4-cyclohexenylene;

[0313] The above-mentioned groups (a), (b), (c) and (d) may be substituted by cyano groups, fluorine atoms or chlorine atoms, respectively and independently.

[0314] Z N11 , Z N12 , Z N21 , Z N22 , Z N31 and Z N32 Each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -COO-, -OCO-, -OCF2-, -CF2O-, -CH=N-N=CH-, -CH=CH-, -CF=CF- or -C≡C-,

[0315] X N21 represents a hydrogen atom or a fluorine atom,

[0316] T N31 represents -CH2- or oxygen atom,

[0317] n N11 、n N12 、n N21 、n N22 、n N31 and n N32 Each independently represents an integer from 0 to 3, and n N11 +n N12 、n N21 +n N22 and n N31 +n N32 are independently 1, 2 or 3,

[0318] In the presence of multiple A N11 ~A N32 , Z N11 ~Z N32 , they may be the same as or different from each other).

[0319] The compound represented by any one of the general formulae (N-1), (N-2) and (N-3) is preferably a compound having a negative Δε and an absolute value greater than 3.

[0320] In the general formulas (N-1), (N-2) and (N-3), RN11 , R N12 , R N21 , R N22 , R N31 and R N32 Each independently preferably is an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms; preferably is 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; more preferably is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms; further preferably is an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms; and particularly preferably is an alkenyl group having 3 carbon atoms (propenyl).

[0321] In addition, R N11 , R N12 , R N21 , R N22 , R N31 and R N32 When the ring structure to which they are bound is a phenyl (aromatic), preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms, and when the ring structure to which they are bound is a saturated ring structure such as cyclohexane, pyran, and dioxane, preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, the total number of carbon atoms and oxygen atoms when present is preferably 5 or less, and preferably linear.

[0322] The alkenyl group is preferably a group represented by any one selected from the group consisting of Formula (R1) to Formula (R5) (a black dot in each formula represents a bond).

[0323] [Chemistry 89]

[0324]

[0325] A N11 , A N12 , A N21 , A N22 , A N31 and A N32When Δn needs to be increased, each independently is preferably aromatic, and in order to improve the response speed, is preferably aliphatic, and preferably represents trans-1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and more preferably represents the following structure.

[0326] [Chemistry 90]

[0327]

[0328] More preferably, it represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group, or a 1,4-phenylene group.

[0329] Z N11 , Z N12 , Z N21 , Z N22 , Z N31 and Z N32 Each independently preferably represents -CH2O-, -CF2O-, -CH2CH2-, -CF2CF2- or a single bond, more preferably -CH2O-, -CH2CH2- or a single bond, and particularly preferably -CH2O- or a single bond.

[0330] X N21 Preferred is a fluorine atom.

[0331] T N31 Preferred is an oxygen atom.

[0332] n N11 +n N12 、n N21 +n N22 and n N31 +n N32 Preferably 1 or 2, preferably n N11 is 1 and n N12 The combination of 0, n N11 is 2 and n N12 The combination of 0, n N11 is 1 and n N12 The combination of 1, n N11 is 2 and n N12 The combination of 1, n N21 is 1 and n N22 The combination of 0, n N21 is 2 and n N22 The combination of 0, n N31 is 1 and nN32 The combination of 0, n N31 is 2 and n N32 A combination of 0.

[0333] The preferred lower limit of the content of the compound represented by formula (N-1) relative to the total amount of the liquid crystal composition is 1% by mass or more, 10% by mass or more, 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, 75% by mass or more, 80% by mass or more. The preferred upper limit of the 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, 20% by mass or less.

[0334] The preferred lower limit of the content of the compound represented by formula (N-2) relative to the total amount of the liquid crystal composition is 1% by mass or more, 10% by mass or more, 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, 75% by mass or more, 80% by mass or more. The preferred upper limit of the 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, 20% by mass or less.

[0335] The preferred lower limit of the content of the compound represented by formula (N-3) relative to the total amount of the liquid crystal composition is 1% by mass or more, 10% by mass or more, 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, 75% by mass or more, 80% by mass or more. The preferred upper limit of the 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, 20% by mass or less.

[0336] When viscosity needs to be maintained at a relatively low, fast response liquid crystal composition, the lower limit of the above-mentioned content is preferably low and the upper limit is low. When Tni needs to be maintained at a relatively high, good temperature stability liquid crystal composition, the lower limit of the above-mentioned content is preferably low and the upper limit is low. In addition, in order to maintain the driving voltage at a relatively low level, when the dielectric anisotropy of the liquid crystal composition is relatively large, the lower limit of the above-mentioned content is preferably high and the upper limit is high.

[0337] Examples of the compound represented by the general formula (N-1) include the compound group represented by the following general formulae (N-1a) to (N-1g).

[0338] [Chemistry 91]

[0339]

[0340] (Where R N11 and R N12 Indicates that R in the general formula (N-1) N11 and R N12 Same meaning,

[0341] n Na11 Indicates 0 or 1, n Nb11 Indicates 0 or 1, n Nc11 Indicates 0 or 1, n Nd11 Indicates 0 or 1, n Ne11 Indicates 1 or 2, n Nf11 Indicates 1 or 2, n Ng11 Indicates 1 or 2,

[0342] A Ne11 represents trans-1,4-cyclohexylene or 1,4-phenylene,

[0343] A Ng11 represents trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-phenylene, at least one of which represents 1,4-cyclohexenylene,

[0344] Z Ne11 represents a single bond or an ethylene group, but at least one represents an ethylene group).

[0345] More specifically, the compound represented by the general formula (N-1) is preferably a compound selected from the group consisting of compounds represented by general formulae (N-1-1) to (N-1-22).

[0346] The compound represented by the general formula (N-1-1) is the following compound.

[0347] [Chemistry 92]

[0348]

[0349] (Where R N111 and R N112 Each independently represents R in the general formula (N) N11 and R N12 Same meaning).

[0350] R N111 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and is preferably a propyl group, a pentyl group or a vinyl group. N112It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and is preferably an ethoxy group or a butoxy group.

[0351] The compound represented by the general formula (N-1-1) can be used alone or in combination of two or more compounds. The types of the compounds that can be combined are not particularly limited, and they can be used in appropriate combinations according to the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used, for example, as an embodiment, are 1, 2, 3, 4, 5 or more.

[0352] When the compound represented by the general formula (N-1-1) is emphasized on the improvement of Δε, it is preferred to set the content to a higher value. When the solubility at low temperature is emphasized, the effect is higher when the content is set to a larger value. When Tni is emphasized, the effect is higher when the content is set to a smaller value. Furthermore, when the compound represented by the general formula (N-1-1) is used to improve drip marks and screen burn-in characteristics, it is preferred to set the content range to an intermediate value.

[0353] The lower limit of the preferred content of the compound represented by formula (N-1-1) relative to the total amount of the liquid crystal composition is 5% by mass or more, 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 or more, 30% by mass or more, 33% by mass or more, or 35% by mass or more. The upper limit of the preferred content is 50% by mass or less, 40% by mass or less, 38% by mass or less, 35% by mass or less, 33% by mass 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 or less, 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, or 3% by mass or less, relative to the total amount of the liquid crystal composition.

[0354] The compound represented by general formula (N-1-1) is preferably a compound selected from the group consisting of compounds represented by formulae (N-1-1.1) to (N-1-1.23), preferably a compound represented by formulae (N-1-1.1) to (N-1-1.4), and preferably a compound represented by formulae (N-1-1.1) and (N-1-1.3).

[0355] [Chemistry 93]

[0356]

[0357] The compounds represented by formulae (N-1-1.1) to (N-1-1.22) may be used alone or in combination, and the preferred lower limit of the content of each of these compounds is 5% by mass or more relative to the total amount of the liquid crystal composition, and the upper limit is 50% by mass or less relative to the total amount of the composition of this embodiment.

[0358] The compound represented by the general formula (N-1-2) is the following compound.

[0359] [Chemistry 94]

[0360]

[0361] In the formula, R N121 and R N122 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0362] R N121 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group, a butyl group or a pentyl group.

[0363] R N122 It 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 a methyl group, a propyl group, a methoxy group, an ethoxy group, or a propoxy group.

[0364] The compound represented by the general formula (N-1-2) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0365] The amount of the compound represented by the general formula (N-1-2) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass%, 37 mass%, 40 mass%, 42 mass%. On the other hand, the preferred upper limit is 50 mass%, 48 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%.

[0366] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-2) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a smaller value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-2) is set to the middle of the above range.

[0367] The compound represented by the general formula (N-1-2) is preferably a compound represented by the following formula (N-1-2.1) to (N-1-2.7), formula (N-1-2.10) to (N-1-2.13) or formula (N-1-2.20) to (N-1-2.22), and more preferably a compound represented by formula (N-1-2.3) to (N-1-2.7), formula (N-1-2.10), formula (N-1-2.11), formula (N-1-2.13) or formula (N-1-2.20).

[0368] When emphasis is placed on the improvement of Δε, compounds represented by formulas (N-1-2.3) to (N-1-2.7) are preferred. When emphasis is placed on the improvement of Tni, compounds represented by formulas (N-1-2.10), (N-1-2.11) or (N-1-2.13) are preferred. In addition, when emphasis is placed on the improvement of the response speed, compounds represented by formula (N-1-2.20) are preferred.

[0369] [Chemistry 95]

[0370]

[0371] The compound represented by the general formula (N-1-3) is the following compound.

[0372] [Chemistry 96]

[0373]

[0374] In the formula, R N131 and R N132 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0375] R N131 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0376] R N132 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably a 1-propenyl group, an ethoxy group, a propoxy group, or a butoxy group.

[0377] The compound represented by the general formula (N-1-3) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0378] The amount of the compound represented by the general formula (N-1-3) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0379] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-3) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-3) is set to the middle of the above range.

[0380] The compound represented by the general formula (N-1-3) is preferably a compound represented by the following formula (N-1-3.1) to (N-1-3.7), formula (N-1-3.10), formula (N-1-3.11), formula (N-1-3.20) or formula (N-1-3.21), more preferably a compound represented by formula (N-1-3.1) to (N-1-3.7) or formula (N-1-3.21), and further preferably a compound represented by formula (N-1-3.1) to (N-1-3.4) or formula (N-1-3.6).

[0381] [Chemistry 97]

[0382]

[0383] The compounds represented by formula (N-1-3.1) to (N-1-3.4), formula (N-1-3.6) or formula (N-1-3.21) may be used alone or in combination of two or more. Among them, a combination of a compound represented by formula (N-1-3.1) and a compound represented by formula (N-1-3.2), or a combination of two or three selected from the group consisting of a compound represented by formula (N-1-3.3), a compound represented by formula (N-1-3.4) and a compound represented by formula (N-1-3.6) is preferred.

[0384] The compound represented by the general formula (N-1-4) is the following compound.

[0385] [Chemistry 98]

[0386]

[0387] In the formula, R N141 and R N142 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0388] R N141 and R N142 Each independently 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 a methyl group, a propyl group, an ethoxy group, or a butoxy group.

[0389] The compound represented by the general formula (N-1-4) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0390] The amount of the compound represented by the general formula (N-1-4) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 11 mass%, 10 mass%, 8 mass%.

[0391] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-4) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a smaller value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-4) is set to the middle of the above range.

[0392] The compound represented by the general formula (N-1-4) is preferably a compound represented by the following formula (N-1-4.1) to (N-1-4.4) or formula (N-1-4.11) to (N-1-4.14), more preferably a compound represented by formula (N-1-4.1) to (N-1-4.4), and further preferably a compound represented by formula (N-1-4.1), formula (N-1-4.2) or formula (N-1-4.4).

[0393] [Chemistry 99]

[0394]

[0395] The compound represented by the general formula (N-1-5) is the following compound.

[0396] [Chemical 100]

[0397]

[0398] In the formula, R N151 and R N152 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0399] R N151 and R N152 Each independently 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 ethyl group, a propyl group, or a butyl group.

[0400] The compound represented by the general formula (N-1-5) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and may be appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0401] The amount of the compound represented by the general formula (N-1-5) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 8 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0402] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-5) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a smaller value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-5) is set to the middle of the above range.

[0403] The compound represented by the general formula (N-1-5) is preferably a compound represented by the following formula (N-1-5.1) to (N-1-5.6), and more preferably a compound represented by the formula (N-1-5.1), the formula (N-1-5.2) or the formula (N-1-5.4).

[0404] [Chemistry 101]

[0405]

[0406] The compound represented by the general formula (N-1-10) is the following compound.

[0407] [Chemistry 102]

[0408]

[0409] In the formula, R N1101 and R N1102 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0410] R N1101 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.

[0411] R N1102 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0412] The compound represented by the general formula (N-1-10) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0413] The amount of the compound represented by the general formula (N-1-10) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0414] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-10) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a higher value, and when Tni is emphasized, the effect is higher when the amount is set to a higher value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-10) is set to the middle of the above range.

[0415] The compound represented by the general formula (N-1-10) is preferably a compound represented by the following formulas (N-1-10.1) to (N-1-10.5) or (N-1-10.11) to (N-1-10.14), more preferably a compound represented by formulas (N-1-10.1) to (N-1-10.5), and even more preferably a compound represented by formula (N-1-10.1) or (N-1-10.2).

[0416] [Chemistry 103]

[0417]

[0418] The compound represented by the general formula (N-1-11) is the following compound.

[0419] [Chemistry 104]

[0420]

[0421] In the formula, R N1111 and R N1112 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0422] R N1111 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group.

[0423] R N1112 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0424] The compound represented by the general formula (N-1-11) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0425] The amount of the compound represented by the general formula (N-1-11) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0426] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-11) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a lower value, and when Tni is emphasized, the effect is higher when the amount is set to a higher value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-11) is set to the middle of the above range.

[0427] The compound represented by the general formula (N-1-11) is preferably a compound represented by the following formula (N-1-11.1) to (N-1-11.5) or formula (N-1-11.11) to (N-1-11.14), more preferably a compound represented by formula (N-1-11.1) to (N-1-11.5), and further preferably a compound represented by formula (N-1-11.2) or formula (N-1-11.4).

[0428] [Chemistry 105]

[0429]

[0430] The compound represented by the general formula (N-1-12) is the following compound.

[0431] [Chemistry 106]

[0432]

[0433] In the formula, R N1121 and R N1122 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0434] R N1121 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0435] R N1122 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0436] The compound represented by the general formula (N-1-12) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0437] The amount of the compound represented by the general formula (N-1-12) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0438] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-12) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-12) is set to the middle of the above range.

[0439] The compound represented by the general formula (N-1-13) is the following compound.

[0440] [Chemistry 107]

[0441]

[0442] In the formula, R N1131 and R N1132 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0443] R N1131 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0444] R N1132 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0445] The compound represented by the general formula (N-1-13) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0446] The amount of the compound represented by the general formula (N-1-13) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0447] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-13) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-13) is set to the middle of the above range.

[0448] The compound represented by the general formula (N-1-14) is the following compound.

[0449] [Chemistry 108]

[0450]

[0451] In the formula, R N1141 and R N1142 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0452] R N1141 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0453] R N1142 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0454] The compound represented by the general formula (N-1-14) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0455] The amount of the compound represented by the general formula (N-1-14) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0456] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-14) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-14) is set to the middle of the above range.

[0457] The compound represented by the general formula (N-1-15) is the following compound.

[0458] [Chemistry 109]

[0459]

[0460] In the formula, R N1151 and R N1152 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0461] R N1151 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0462] R N1152 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0463] The compound represented by the general formula (N-1-15) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0464] The amount of the compound represented by the general formula (N-1-15) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0465] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-15) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-15) is set to the middle of the above range.

[0466] The compound represented by the general formula (N-1-16) is the following compound.

[0467] [Chemistry 110]

[0468]

[0469] In the formula, R N1161 and R N1162 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0470] R N1161 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0471] R N1162 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0472] The compound represented by the general formula (N-1-16) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0473] The amount of the compound represented by the general formula (N-1-16) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0474] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-16) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-16) is set to the middle of the above range.

[0475] The compound represented by the general formula (N-1-17) is the following compound.

[0476] [Chemistry 111]

[0477]

[0478] In the formula, R N1171 and R N1172 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0479] R N1171 It is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0480] R N1172 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0481] The compound represented by the general formula (N-1-17) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0482] The amount of the compound represented by the general formula (N-1-17) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0483] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-17) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-17) is set to the middle of the above range.

[0484] The compound represented by the general formula (N-1-18) is the following compound.

[0485] [Chemistry 112]

[0486]

[0487] In the formula, R N1181 and R N1182 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0488] R N1181 It 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 methyl group, an ethyl group, a propyl group or a butyl group.

[0489] R N1182 It is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and more preferably an ethoxy group, a propoxy group, or a butoxy group.

[0490] The compound represented by the general formula (N-1-18) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0491] The amount of the compound represented by the general formula (N-1-18) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0492] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-18) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-18) is set to the middle of the above range.

[0493] The compound represented by the general formula (N-1-18) is preferably a compound represented by the following formula (N-1-18.1) to (N-1-18.5), more preferably a compound represented by formula (N-1-18.1) to (N-1-18.3), and further preferably a compound represented by formula (N-1-18.2) or formula (N-1-18.3).

[0494] [Chemistry 113]

[0495]

[0496] The compound represented by the general formula (N-1-20) is the following compound.

[0497] [Chemistry 114]

[0498]

[0499] In the formula, R N1201 and R N1202 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0500] R N1201 and R N1202 Each independently is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0501] The compound represented by the general formula (N-1-20) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0502] The amount of the compound represented by the general formula (N-1-20) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0503] When the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-20) is set to a higher value. When the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value. When Tni is emphasized, it is preferred that the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, the amount of the compound represented by the general formula (N-1-20) is set to the middle of the above range.

[0504] The compound represented by the general formula (N-1-21) is the following compound.

[0505] [Chemistry 115]

[0506]

[0507] R N1211 and R N1212 Each independently is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0508] The compound represented by the general formula (N-1-21) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0509] The amount of the compound represented by the general formula (N-1-21) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%. On the other hand, the preferred upper limit is 35 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0510] When the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-21) is set to a higher value. When the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value. When Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-21) is set to the middle of the above range.

[0511] The compound represented by the general formula (N-1-22) is the following compound.

[0512] [Chemistry 116]

[0513]

[0514] In the formula, R N1221 and R N1222 Respectively represent R in the general formula (N-1) N11 and R N12 Same meaning.

[0515] R N1221 and R N1222 Each independently is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and more preferably an ethyl group, a propyl group or a butyl group.

[0516] The compound represented by the general formula (N-1-22) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0517] The amount of the compound represented by the general formula (N-1-22) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass %, 5 mass %, 10 mass %, 13 mass %, 15 mass %, 17 mass %, 20 mass %. On the other hand, the preferred upper limit is 35 mass %, 30 mass %, 28 mass %, 25 mass %, 23 mass %, 20 mass %, 18 mass %, 15 mass %, 13 mass %, 10 mass %, 5 mass %.

[0518] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-1-22) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a larger value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-1-21) is set to the middle of the above range.

[0519] The compound represented by the general formula (N-1-22) is preferably a compound represented by the following formula (N-1-22.1) to (N-1-22.6), formula (N-1-22.11) or (N-1-22.12), more preferably a compound represented by formula (N-1-22.1) to (N-1-22.5), and even more preferably a compound represented by formula (N-1-22.1) to (N-1-22.4).

[0520] [Chemistry 117]

[0521]

[0522] The compound represented by the general formula (N-3) is preferably a compound represented by the following general formula (N-3-2).

[0523] [Chemistry 118]

[0524]

[0525] In the formula, R N321 and R N322 Respectively represent the R N31 and R N32 Same meaning.

[0526] R N321 and R N322 It 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 or a pentyl group.

[0527] The compound represented by the general formula (N-3-2) may be used alone or in combination of two or more. The type of the compound to be combined is not particularly limited and is appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used may be, for example, one, two, three, four, or five or more.

[0528] The amount of the compound represented by the general formula (N-3-2) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 3 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass%. On the other hand, the preferred upper limit is 50 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%, 28 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%.

[0529] Furthermore, when the improvement of Δε is emphasized, it is preferred that the amount of the compound represented by the general formula (N-3-2) is set to a higher value, when the solubility at low temperature is emphasized, the effect is higher when the amount is set to a larger value, and when Tni is emphasized, the effect is higher when the amount is set to a smaller value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred that the amount of the compound represented by the general formula (N-3-2) is set to the middle of the above range.

[0530] The compound represented by the general formula (N-3-2) is preferably a compound represented by the following formulas (N-3-2.1) to (N-3-2.3).

[0531] [Chemistry 119]

[0532]

[0533] The liquid crystal composition may further contain at least one compound selected from compounds represented by the following general formula (L) as a non-polymerizable liquid crystal compound (liquid crystal molecule).

[0534] [Chemistry 120]

[0535]

[0536] (In the above general formula (L),

[0537] R L1 and R L2 Each independently represents an alkyl group having 1 to 8 carbon atoms, and any one or two or more non-adjacent -CH2- groups in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-.

[0538] n L1 represents 0, 1, 2 or 3,

[0539] A L1 , A L2 and A L3 each independently represents a group selected from the group consisting of the radical (a), the radical (b), and the radical (c),

[0540] (a) 1,4-cyclohexylene (any one or two or more non-adjacent -CH2- groups in the group may be substituted with -O-),

[0541] (b) 1,4-phenylene (any one or two or more non-adjacent -CH= groups in the group may be substituted with -N=), and

[0542] (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (any one or two or more non-adjacent -CH= groups in the group may be substituted with -N=),

[0543] The above-mentioned group (a), group (b) and group (c) may be substituted by a cyano group, a fluorine atom or a chlorine atom, respectively and independently.

[0544] Z L1 and Z L2 Each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -COO-, -OCO-, -OCF2-, -CF2O-, -CH=N-N=CH-, -CH=CH-, -CF=CF- or -C≡C-,

[0545] In n L1 There are multiple A's for 2 or 3 L2 They can be the same or different.

[0546] In n L1 There are multiple Zs for 2 or 3 L2 They may be the same or different.

[0547] However, compounds represented by general formula (N-1), (N-2) and (N-3) are not included).

[0548] The compound represented by the general formula (L) corresponds to a dielectrically almost neutral compound (Δε value is -2 to 2). Therefore, by adding the compound to a liquid crystal composition, various properties of the liquid crystal composition can be adjusted.

[0549] The compound represented by the general formula (L) may be used alone or in combination of two or more. The types of the compounds that can be used in combination are not particularly limited and are appropriately selected according to the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The type of compound used, for example, is one in one embodiment of the present invention. Alternatively, the type of compound used in another embodiment of the present invention is 2, 3, 4, 5, 6, 7, 8, 9, 10 or more.

[0550] The amount of the compound represented by the general formula (L) contained in the liquid crystal composition is appropriately adjusted according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, drip marks, screen burn-in, dielectric constant anisotropy, etc. The preferred lower limit is 1 mass%, 10 mass%, 20 mass%, 30 mass%, 40 mass%, 50 mass%, 55 mass%, 60 mass%, 65 mass%, 70 mass%, 75 mass%, 80 mass%. On the other hand, the preferred upper limit is 95 mass%, 85 mass%, 75 mass%, 65 mass%, 55 mass%, 45 mass%, 35 mass%, 25 mass%.

[0551] When the viscosity of the liquid crystal composition is kept at a low level and the response speed needs to be increased, it is preferred that the lower limit of the amount of the compound represented by the general formula (L) is high and the upper limit is also high. Further, when the Tni of the liquid crystal composition is kept at a high level and the temperature stability needs to be improved, it is preferred that the above lower limit is high and the upper limit is also high. In addition, when the driving voltage of the liquid crystal composition is kept at a low level and the dielectric anisotropy is to be increased, it is preferred that the above lower limit is low and the upper limit is also low. When reliability is important, it is preferred that R L1 and R L2 Both are alkyl groups. When reducing volatility is important, R L1 and R L2 Both are alkoxy groups. When the importance is placed on reducing the viscosity of the liquid crystal composition, R L1 and R L2 At least one of them is an alkenyl group. The number of halogen atoms present in the molecule is preferably 0, 1, 2 or 3, more preferably 0 or 1, and further preferably 1 when compatibility with other liquid crystal molecules is important.

[0552] R L1 and R L2 When they are combined with a ring structure that is a benzene ring (aromatic ring), they are preferably linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, or alkenyl groups having 4 to 5 carbon atoms. When they are combined with a saturated ring structure such as a cyclohexane ring, a pyran ring, or a dioxane ring, they are preferably linear alkyl groups having 1 to 5 carbon atoms, linear alkoxy groups having 1 to 4 carbon atoms, or alkenyl groups having 2 to 5 carbon atoms. In order to stabilize the nematic phase, the number of carbon atoms (when oxygen atoms are contained, the total number of carbon atoms and oxygen atoms) is preferably 5 or less, and linear is also preferred.

[0553] The alkenyl group is preferably a group represented by any one selected from the following formulae (R1) to (R5).

[0554] [Chemistry 121]

[0555]

[0556] (The black dots in the formulas represent carbon atoms in the ring structure).

[0557] n L1 When the response speed is important, it is preferably 0, and in order to improve the upper limit temperature of the nematic phase, it is preferably 2 or 3. In order to achieve a balance between these, it is preferably 1. In addition, in order to satisfy the characteristics required as a liquid crystal composition, it is preferred to use n L1 The compound is represented by a plurality of general formula (L) having different values.

[0558] A L1 , A L2 and A L3 When Δn needs to be increased, the aromatic group is preferred, and in order to improve the response speed, the aliphatic group is preferred. L1 , A L2 and A L3 Each independently preferably is a trans-1,4-cyclohexylene group, a 1,4-phenylene group, a 2-fluoro-1,4-phenylene group, a 3-fluoro-1,4-phenylene group, a 3,5-difluoro-1,4-phenylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, more preferably any of the following groups, and still more preferably a trans-1,4-cyclohexylene group or a 1,4-phenylene group.

[0559] [Chemistry 122]

[0560]

[0561] When response speed is important, Z L1 and Z L2 Preferred is a single bond.

[0562] The number of halogen atoms present in the molecule of the compound represented by the general formula (L) is preferably 0 or 1.

[0563] More specifically, the compound represented by the general formula (L) is preferably selected from compounds represented by the following general formulae (L-1) to (L-6).

[0564] The compound represented by the general formula (L-1) is the following compound.

[0565] [Chemistry 123]

[0566]

[0567] (Where R L11 and R L12 Each independently represents R in the general formula (L)L1 and R L2 Same meaning).

[0568] R L11 and R L12 Preferably, each of them is independently a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0569] The compound represented by the general formula (L-1) may be used alone or in combination of two or more. The types of the compounds that can be used in combination are not particularly limited and are appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used, for example, in one embodiment of the present invention are 1, 2, 3, 4, 5 or more.

[0570] The amount of the compound represented by the general formula (L-1) contained in the liquid crystal composition is set as follows. That is, the preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 15 mass%, 20 mass%, 25 mass%, 30 mass%, 35 mass%, 40 mass%, 45 mass%, 50 mass%, 55 mass%. On the other hand, the preferred upper limit is 95 mass%, 90 mass%, 85 mass%, 80 mass%, 75 mass%, 70 mass%, 65 mass%, 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%. When the viscosity of the liquid crystal composition is kept at a low level and the response speed needs to be increased, it is preferred that the lower limit is high and the upper limit is high. Further, when the Tni of the liquid crystal composition is kept at a high level and the temperature stability needs to be improved, it is preferred that the lower limit is in the middle and the upper limit is in the middle. When the driving voltage of the liquid crystal composition is to be kept low and the dielectric anisotropy thereof is to be increased, it is preferred that the lower limit value is low and the upper limit value is also low.

[0571] The compound represented by the general formula (L-1) is preferably selected from compounds represented by the general formula (L-1-1).

[0572] [Chemistry 124]

[0573]

[0574] (Where R L12 Indicates that R in the general formula (L-1) L12 Same meaning).

[0575] The compound represented by general formula (L-1-1) is preferably a compound selected from formulae (L-1-1.1) to (L-1-1.3), more preferably a compound selected from formulae (L-1-1.2) and (L-1-1.3), and even more preferably a compound represented by formula (L-1-1.3).

[0576] [Chemistry 125]

[0577]

[0578] The amount of the compound represented by formula (L-1-1.3) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%. On the other hand, the preferred upper limit is 20 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass%.

[0579] The compound represented by the general formula (L-1) is preferably selected from compounds represented by the general formula (L-1-2).

[0580] [Chemistry 126]

[0581]

[0582] (Where R L12 Indicates that R in the general formula (L-1) L12 Same meaning).

[0583] The amount of the compound represented by the general formula (L-1-2) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 5 mass%, 10 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass%. On the other hand, the preferred upper limit is 60 mass%, 55 mass%, 50 mass%, 45 mass%, 42 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%.

[0584] Furthermore, the compound represented by the general formula (L-1-2) is preferably a compound selected from the group consisting of the compounds represented by the formulae (L-1-2.1) to (L-1-2.4), and more preferably a compound selected from the group consisting of the compounds represented by the formulae (L-1-2.2) to (L-1-2.4).

[0585] [Chemistry 127]

[0586]

[0587] In particular, the compound represented by formula (L-1-2.2) can particularly improve the response speed of the liquid crystal composition and is therefore preferred. In addition, when a high Tni is required rather than a response speed, it is preferred to use a compound represented by formula (L-1-2.3) or formula (L-1-2.4). Furthermore, in order to achieve good solubility at low temperatures, it is not preferred that the total amount of the compound represented by formula (L-1-2.3) and the compound represented by formula (L-1-2.4) contained in the liquid crystal composition is more than 30% by mass.

[0588] The amount of the compound represented by formula (L-1-2.2) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 10 mass%, 15 mass%, 18 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 33 mass%, 35 mass%, 38 mass%, 40 mass%. On the other hand, the preferred upper limit is 60 mass%, 55 mass%, 50 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 32 mass%, 30 mass%, 27 mass%, 25 mass%, 22 mass%.

[0589] The total amount of the compound represented by formula (L-1-1.3) and the compound represented by formula (L-1-2.2) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 10 mass%, 15 mass%, 20 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass%, 40 mass%. On the other hand, the preferred upper limit is 60 mass%, 55 mass%, 50 mass%, 45 mass%, 43 mass%, 40 mass%, 38 mass%, 35 mass%, 32 mass%, 30 mass%, 27 mass%, 25 mass%, 22 mass%.

[0590] The compound represented by the general formula (L-1) is preferably selected from compounds represented by the general formula (L-1-3).

[0591] [Chemistry 128]

[0592]

[0593] (Where R L13 and R L14 Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms).

[0594] R L13 and R L14 Preferably, each of them is independently a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0595] The amount of the compound represented by formula (L-1-3) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 5 mass%, 10 mass%, 13 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 30 mass%. On the other hand, the preferred upper limit is 60 mass%, 55 mass%, 50 mass%, 45 mass%, 40 mass%, 37 mass%, 35 mass%, 33 mass%, 30 mass%, 27 mass%, 25 mass%, 23 mass%, 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass%.

[0596] Furthermore, the compound represented by general formula (L-1-3) is preferably a compound selected from the group consisting of compounds represented by formulae (L-1-3.1) to (L-1-3.13), and more preferably a compound selected from the group consisting of compounds represented by formulae (L-1-3.1), (L-1-3.3) and (L-1-3.4).

[0597] [Chemistry 129]

[0598]

[0599] In particular, the compound represented by formula (L-1-3.1) can particularly improve the response speed of the liquid crystal composition and is therefore preferred. In addition, when a high Tni is required rather than a response speed, it is preferred to use a compound represented by formula (L-1-3.3), formula (L-1-3.4), formula (L-1-3.11) or formula (L-1-3.12). Furthermore, in order to achieve good solubility at low temperatures, it is not preferred that the total amount of the compound represented by formula (L-1-3.3), the compound represented by formula (L-1-3.4), the compound represented by formula (L-1-3.11), and the compound represented by formula (L-1-3.13) contained in the liquid crystal composition is greater than 20% by mass.

[0600] The amount of the compound represented by formula (L-1-3.1) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 13 mass%, 15 mass%, 18 mass%, 20 mass%. On the other hand, the preferred upper limit is 20 mass%, 17 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%.

[0601] The compound represented by the general formula (L-1) is preferably a compound selected from the group consisting of compounds represented by the general formula (L-1-4) and the general formula (L-1-5).

[0602] [Chemistry 130]

[0603]

[0604] (Where R L15 and R L16 Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms).

[0605] R L15 and R L16 Preferably, each of them is independently a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.

[0606] The amount of the compound represented by formula (L-1-4) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass %, 5 mass %, 10 mass %, 13 mass %, 15 mass %, 17 mass %, 20 mass %. On the other hand, the preferred upper limit is 25 mass %, 23 mass %, 20 mass %, 17 mass %, 15 mass %, 13 mass %, 10 mass %.

[0607] The amount of the compound represented by formula (L-1-5) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass %, 5 mass %, 10 mass %, 13 mass %, 15 mass %, 17 mass %, 20 mass %. On the other hand, the preferred upper limit is 25 mass %, 23 mass %, 20 mass %, 17 mass %, 15 mass %, 13 mass %, 10 mass %.

[0608] The compound represented by the general formula (L-1) is preferably selected from compounds represented by the general formula (L-1-6).

[0609] [Chemistry 131]

[0610]

[0611] (Where R L17 and R L18 each independently represents a methyl group or a hydrogen atom).

[0612] The amount of the compound represented by the general formula (L-1-6) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 5 mass%, 10 mass%, 15 mass%, 17 mass%, 20 mass%, 23 mass%, 25 mass%, 27 mass%, 30 mass%, 35 mass%. On the other hand, the preferred upper limit is 60 mass%, 55 mass%, 50 mass%, 45 mass%, 42 mass%, 40 mass%, 38 mass%, 35 mass%, 33 mass%, 30 mass%.

[0613] The compound represented by the general formula (L-2) is the following compound.

[0614] [Chemistry 132]

[0615]

[0616] (Where R L21 and R L22 Each independently represents R in the general formula (L) L1 and R L2 Same meaning).

[0617] R L21 An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferred.

[0618] R L22 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 is preferred.

[0619] The compound represented by the general formula (L-2) may be used alone or in combination of two or more. The types of the compounds that can be used in combination are not particularly limited and are appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used, for example, in one embodiment of the present invention are 1, 2, 3, 4, 5 or more.

[0620] The amount of the compound represented by the general formula (L-2) contained in the liquid crystal composition, when the solubility at low temperature is emphasized, the effect is higher if it is set to a higher value, and conversely, when the response speed is emphasized, the effect is higher if it is set to a lower value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred to set the range of its amount in the middle. The preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%. On the other hand, the preferred upper limit is 20 mass%, 15 mass%, 13 mass%, 10% mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass%.

[0621] Furthermore, the compound represented by general formula (L-2) is preferably a compound selected from the group consisting of compounds represented by formulae (L-2.1) to (L-2.6), and more preferably a compound selected from the group consisting of formulae (L-2.1), (L-2.3), (L-2.4) and (L-2.6).

[0622] [Chemistry 133]

[0623]

[0624] The compound represented by the general formula (L-3) is the following compound.

[0625] [Chemistry 134]

[0626]

[0627] (Where R L31 and R L32 Each independently represents R in the general formula (L) L1 and R L2 Same meaning).

[0628] R L31 and R L32 Preferably, each of them is independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

[0629] The compound represented by the general formula (L-3) may be used alone or in combination of two or more. The types of the compounds that can be used in combination are not particularly limited and are appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used, for example, in one embodiment of the present invention are 1, 2, 3, 4, 5 or more.

[0630] The amount of the compound represented by the general formula (L-3) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%. On the other hand, the preferred upper limit is 20 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%, 7 mass%, 6 mass%, 5 mass%, 3 mass%. The amount of the compound represented by the general formula (L-3) contained in the liquid crystal composition is set to a higher value when a high birefringence is obtained, and conversely, when a high Tni is emphasized, the effect is higher when it is set to a lower value. Furthermore, when improving drip marks and screen burn-in characteristics, it is preferred to set the range of its amount in the middle.

[0631] Furthermore, the compound represented by the general formula (L-3) is preferably a compound selected from the group consisting of compounds represented by formulae (L-3.1) to (L-3.7), and more preferably a compound selected from the group consisting of compounds represented by formulae (L-3.2) to (L-3.5).

[0632] [Chemistry 135]

[0633]

[0634] The compound represented by the general formula (L-4) is the following compound.

[0635] [Chemistry 136]

[0636]

[0637] (Where R L41 and R L42Each independently represents R in the general formula (L) L1 and R L2 Same meaning).

[0638] R L41 An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferred.

[0639] R L42 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 is preferred.

[0640] The compound represented by the general formula (L-4) may be used alone or in combination of two or more. The types of the compounds that can be used in combination are not particularly limited and are appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used, for example, in one embodiment of the present invention are 1, 2, 3, 4, 5 or more.

[0641] The amount of the compound represented by the general formula (L-4) contained in the liquid crystal composition is appropriately adjusted according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, drip marks, screen burn-in, dielectric anisotropy, etc. The preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass%. On the other hand, the preferred upper limit is 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%.

[0642] Furthermore, the compound represented by the general formula (L-4) is preferably a compound selected from the group consisting of compounds represented by formulae (L-4.1) to (L-4.3).

[0643] [Chemistry 137]

[0644]

[0645] The liquid crystal composition may contain a compound represented by formula (L-4.1), a compound represented by formula (L-4.2), both a compound represented by formula (L-4.1) and a compound represented by formula (L-4.2), or all of the compounds represented by formulas (L-4.1) to (L-4.3), depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, and birefringence.

[0646] The amount of the compound represented by formula (L-4.1) or formula (L-4.2) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 3 mass%, 5 mass%, 7 mass%, 9 mass%, 11 mass%, 12 mass%, 13 mass%, 18 mass%, 21 mass%. On the other hand, the preferred upper limit is 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%.

[0647] When the liquid crystal composition contains both the compound represented by formula (L-4.1) and the compound represented by formula (L-4.2), the total amount of these compounds contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 15 mass%, 19 mass%, 24 mass%, 30 mass%. On the other hand, the preferred upper limit is 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0648] The compound represented by the general formula (L-4) is preferably a compound selected from the group consisting of compounds represented by formulae (L-4.4) to (L-4.6), and more preferably a compound selected from the group consisting of compounds represented by formula (L-4.4).

[0649] [Chemistry 138]

[0650]

[0651] The liquid crystal composition may contain a compound represented by formula (L-4.4), a compound represented by formula (L-4.5), or both a compound represented by formula (L-4.4) and a compound represented by formula (L-4.5), depending on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, and birefringence.

[0652] The amount of the compound represented by formula (L-4.4) or formula (L-4.5) in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 3 mass%, 5 mass%, 7 mass%, 9 mass%, 11 mass%, 12 mass%, 13 mass%, 18 mass%, 21 mass%. On the other hand, the preferred upper limit is 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%, 10 mass%, 8 mass%.

[0653] When the liquid crystal composition contains both the compound represented by formula (L-4.4) and the compound represented by formula (L-4.5), the total amount of these compounds contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 15 mass%, 19 mass%, 24 mass%, 30 mass%. On the other hand, the preferred upper limit is 45 mass%, 40 mass%, 35 mass%, 30 mass%, 25 mass%, 23 mass%, 20 mass%, 18 mass%, 15 mass%, 13 mass%.

[0654] The compound represented by the general formula (L-4) is preferably a compound selected from the group consisting of compounds represented by formulae (L-4.7) to (L-4.10), and is particularly preferably a compound represented by formula (L-4.9).

[0655] [Chemistry 139]

[0656]

[0657] The compound represented by the general formula (L-5) is the following compound.

[0658] [Chemistry 140]

[0659]

[0660] (Where R L51 and R L52 Each independently represents R in the general formula (L) L1 and R L2 Same meaning).

[0661] R L51 An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferred.

[0662] R L52 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 is preferred.

[0663] The compound represented by the general formula (L-5) may be used alone or in combination of two or more. The types of the compounds that can be used in combination are not particularly limited and are appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used, for example, in one embodiment of the present invention are 1, 2, 3, 4, 5 or more.

[0664] The amount of the compound represented by the general formula (L-5) contained in the liquid crystal composition is appropriately adjusted according to the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, drip marks, screen burn-in, dielectric anisotropy, etc. The preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass%. On the other hand, the preferred upper limit is 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%.

[0665] Furthermore, the compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2), and is particularly preferably a compound represented by the formula (L-5.1). The amount of each compound contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, and 7 mass%. On the other hand, the preferred upper limit is 20 mass%, 15 mass%, 13 mass%, 10 mass%, and 9 mass%.

[0666] [Chemistry 141]

[0667]

[0668] In addition, the compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4). The amount of each compound contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%. On the other hand, the preferred upper limit is 20 mass%, 15 mass%, 13 mass%, 10 mass%, 9 mass%.

[0669] [Chemistry 142]

[0670]

[0671] In addition, the compound represented by the general formula (L-5) is preferably a compound selected from the compounds represented by formulas (L-5.5) to (L-5.7), and is particularly preferably a compound represented by formula (L-5.7). The amount of each compound contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1% by mass, 2% by mass, 3% by mass, 5% by mass, and 7% by mass. On the other hand, the preferred upper limit is 20% by mass, 15% by mass, 13% by mass, 10% by mass, and 9% by mass.

[0672] [Chemistry 143]

[0673]

[0674] The compound represented by the general formula (L-6) is the following compound.

[0675] [Chemistry 144]

[0676]

[0677] (Where R L61 and R L62 Each independently represents R in the general formula (L) L1 and R L2 Same meaning, X L61 and X L62 each independently represents a hydrogen atom or a fluorine atom).

[0678] R L61 and R L62 Preferably, each of them is independently an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms.

[0679] Preferred X L61 and X L62 One of them is a fluorine atom and the other is a hydrogen atom.

[0680] The compound represented by the general formula (L-6) may be used alone or in combination of two or more. The types of the compounds that can be used in combination are not particularly limited and are appropriately selected based on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. The types of compounds used, for example, in one embodiment of the present invention are 1, 2, 3, 4, 5 or more.

[0681] The amount of the compound represented by the general formula (L-6) contained in the liquid crystal composition is preferably as follows. That is, the preferred lower limit is 1 mass%, 2 mass%, 3 mass%, 5 mass%, 7 mass%, 10 mass%, 14 mass%, 16 mass%, 20 mass%, 23 mass%, 26 mass%, 30 mass%, 35 mass%, 40 mass%. On the other hand, the preferred upper limit is 50 mass%, 40 mass%, 35 mass%, 30 mass%, 20 mass%, 15 mass%, 10 mass%, 5 mass%. Furthermore, the amount of the compound represented by the general formula (L-6) is preferably set to more when the focus is on increasing Δn, and is preferably set to less when the focus is on precipitation at low temperature.

[0682] Furthermore, the compound represented by the general formula (L-6) is preferably a compound selected from the group consisting of compounds represented by formulae (L-6.1) to (L-6.9).

[0683] [Chemistry 145]

[0684]

[0685] The types of compounds that can be used in combination are not particularly limited, but preferably 1 to 3 compounds are selected from the compounds represented by formula (L-6.1) to (L-6.9), and more preferably 1 to 4 compounds are selected. In addition, a wide molecular weight distribution of the compound used in combination also contributes to solubility. Therefore, for example, it is preferred to select one compound represented by formula (L-6.1) and formula (L-6.2), one compound represented by formula (L-6.4) and formula (L-6.5), one compound represented by formula (L-6.6) and formula (L-6.7), and one compound represented by formula (L-6.8) and formula (L-6.9), and appropriately combine them. Among them, it is preferred to contain compounds represented by formula (L-6.1), formula (L-6.3), formula (L-6.4), formula (L-6.6), and formula (L-6.9).

[0686] The compound represented by the general formula (L-6) is preferably a compound selected from the group consisting of compounds represented by formulae (L-6.10) to (L-6.17), and more preferably a compound represented by formula (L-6.11).

[0687] [Chemistry 146]

[0688]

[0689] The amount of each compound contained in the liquid crystal composition is preferably as follows. That is, its preferred lower limit is 1 mass %, 2 mass %, 3 mass %, 5 mass %, 7 mass %. On the other hand, its preferred upper limit is 20 mass %, 15 mass %, 13 mass %, 10 mass %, 9 mass %.

[0690] The liquid crystal composition preferably does not contain a compound having a structure in which oxygen atoms such as a peroxide (-CO-OO-) structure are bonded to each other in the molecule. When the reliability and long-term stability of the liquid crystal composition are emphasized, it is preferred that the amount of the compound having a carbonyl group contained in the liquid crystal composition is set to 5% by mass or less, more preferably to 3% by mass or less, and further preferably to 1% by mass or less. It is most preferred to be set to substantially 0 (zero) mass%.

[0691] In addition, when emphasis is placed on stability under UV irradiation, the content of the compound substituted with chlorine atoms in the liquid crystal composition is preferably set to 15 mass % or less, more preferably to 10 mass % or less, further preferably to 8 mass % or less, further preferably to 5 mass % or less, particularly preferably to 3 mass % or less, and most preferably to substantially 0 (zero) mass %.

[0692] In addition, it is preferred that the amount of compounds whose ring structures in the molecules are all six-membered rings contained in the liquid crystal composition is relatively large. Specifically, it is preferably set to 80 mass% or more, more preferably to 90 mass% or more, further preferably to 95 mass% or more, and most preferably to substantially 100 mass%.

[0693] In order to prevent or inhibit deterioration caused by oxidation of the liquid crystal composition, it is preferred to reduce the amount of the compound having a cyclohexene ring as a ring structure contained in the liquid crystal composition. Specifically, it is preferably set to 10% by mass or less, more preferably to 8% or less, further preferably to 5% or less, particularly preferably to 3% or less, and most preferably to substantially 0 (zero)% by mass.

[0694] Furthermore, in order to prevent or inhibit degradation caused by oxidation of the liquid crystal composition, it is preferred to reduce the amount of the compound having -CH=CH- as a linking group contained in the liquid crystal composition. Specifically, it is preferably set to 10% by mass or less, more preferably to 5% or less, and further preferably to substantially 0 (zero)% by mass.

[0695] When emphasis is placed on improving the viscosity (η) of the liquid crystal composition and improving the nematic-isotropic liquid phase transition temperature (Tni), it is preferred to reduce the amount of the compound having a 2-methylbenzene-1,4-diyl group in the molecule in which a hydrogen atom can be replaced by a halogen contained in the liquid crystal composition. Specifically, it is preferably set to 10% by mass or less, more preferably to 5% or less, and even more preferably to substantially 0 (zero)% by mass.

[0696] When the compound (liquid crystal molecule, etc.) contained in the liquid crystal composition has a cyclohexylene group having an alkenyl group bonded as a side chain, the number of carbon atoms of the alkenyl group is preferably 2 to 5. In addition, when the compound contained in the liquid crystal composition has a phenylene group having an alkenyl group bonded as a side chain, the number of carbon atoms of the alkenyl group is preferably 4 to 5, and it is preferred that the unsaturated bond of the alkenyl group is not directly bonded to the phenylene group.

[0697] In addition, when the stability of the liquid crystal composition is emphasized, it is preferred to reduce the amount of the compound having an alkenyl group as a side chain and a 2,3-difluorophenyl-1,4-diyl group contained in the liquid crystal composition. Specifically, it is preferably set to 10 mass % or less, more preferably to 5 mass % or less, and further preferably to substantially 0 (zero) mass %.

[0698] In addition to the above-mentioned liquid crystal molecules, the liquid crystal composition may contain other compounds (molecules) such as common nematic liquid crystals, smectic liquid crystals, cholesterol liquid crystals, antioxidants, ultraviolet absorbers, chiral agents, etc., depending on the application. Among them, when the chemical stability of the liquid crystal composition is required, the above-mentioned other compounds are preferably free of chlorine atoms in their structures. In addition, when the stability of the liquid crystal composition to light such as ultraviolet rays is required, the above-mentioned other compounds are preferably free of condensed rings such as naphthalene rings, which have a long conjugation length and an absorption peak in the ultraviolet region, etc.

[0699] C. Other polymeric compounds

[0700] The polymerizable liquid crystal composition of the present invention may further contain one or more polymerizable compounds having a structure different from that of the general formula (i) (hereinafter sometimes referred to as other polymerizable compounds). Other polymerizable compounds may be known polymerizable compounds generally used in liquid crystal compositions.

[0701] Examples of polymerizable compounds having a structure different from that of the general formula (i) include compounds represented by the following general formula (P) (but excluding compounds represented by the general formula (i)).

[0702] [Chemistry 147]

[0703]

[0704] In the above general formula (P), Z p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkoxy group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkenyl group having 2 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkenyloxy group having 2 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, or -Sp p2 -R p2 .

[0705] In the above general formula (P), R p1 and R p2 Each independently represents any one of the following formula (R-I) to formula (R-VIII).

[0706] [Chemistry 148]

[0707]

[0708] (In formula (R-I) to formula (R-VIII),

[0709] In * and Sp p1 Combined,

[0710] R 2 ~R6 each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms,

[0711] W p represents a single bond, -O- or methylene,

[0712] T p represents a single bond or -COO-,

[0713] p, t and q each independently represent 0, 1 or 2).

[0714] In the above general formula (P), Sp p1 and Sp p2 Each independently represents a spacer.

[0715] In the above general formula (P), L p1 and L p2 Each independently represents a single bond, -O-, -S-, -CH2-, -OCH2-, -CH2O-, -CO-, -C2H4-, -COO-, -OCO-, -OCOOCH2-, -CH2OCOO-, -OCH2CH2O-, -CO-NR a -, -NR a -CO-, -SCH2-, -CH2S-, -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-, -(CH2) z -C(=O)-O-, -(CH2) z -O-(C=O)-, -O-(C=O)-(CH2) z -, -(C=O)-O-(CH2) z -, -CH2(CH3)C-C(=O)-O-, -CH2(CH3)C-O-(C=O)-, -O-(C=O)-C(CH3)CH2, -(C=O)-O-C(CH3)-CH2, -CH= CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2-, -CF2O-, -OCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2- or -C≡C- (where, R aEach independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z represents an integer of 1 to 4).

[0716] In the above general formula (P), M p2 M represents 1,4-phenylene, 1,4-cyclohexylene, anthracene-2,6-diyl, phenanthrene-2,7-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-1,4-diyl, naphthalene-2,6-diyl, indan-2,5-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or 1,3-dioxane-2,5-diyl. p2 unsubstituted or may be substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or -R p1 replace.

[0717] In the above general formula (P), M p1 It represents any one of the following formulae (i-11) to (ix-11).

[0718] [Chemistry 149]

[0719]

[0720] (In formulas (i-11) to (ix-11), * and Sp p1 or M p1 Combined with L p1 , L p2 , Z p1 or M p1 combined).

[0721] In the above general formula (P), M p3 It represents any one of the following formulae (i-13) to (ix-13).

[0722] [Chemistry 150]

[0723]

[0724] (In formulas (i-13) to (ix-13), between * and Z p1 or L p2 Combined with L p2 combined).

[0725] In the above general formula (P), m p2 ~m p4 Each independently represents 0, 1, 2 or 3, m p1 and m p5 Each independently represents 1, 2 or 3.

[0726] In the above general formula (P), when there are multiple Z p1 When there are multiple R p1 When there are multiple R p2 When there are multiple Sp p1 When there are multiple Sp p2 When there are multiple L p1 When there are multiple M p2 When , they may be the same as or different from each other.

[0727] Preferably, Z present in the molecule p1 and Z p2 Only one of them is -OCH2-, -CH2O-, -C2H4-, -COO-, -OCO-, -COOC2H4-, -OCOC2H4-, -C2H4OCO-, -C2H4COO-, -CH=CH-, -(CH2)2-COO-, -(CH2)2-OCO-, -OCO-(CH2)2-, -CH=CH-COO-, -COO-CH=CH-, -OCOCH=CH-, -COO-(CH2)2- or -C≡C-, and the others are single bonds, and Z present in the molecule is more preferably p1 and Z p2 Only one of them is -OCH2-, -CH2O-, -C2H4-, -COO- or -OCO-, and the others are single bonds. It is more preferred that Z present in the molecule p1 and Z p2 In addition, Z present in the molecule is preferably p1 and Z p2 Only one of them is a linking group selected from the group consisting of -CH=CH-COO-, -COO-CH=CH-, -(CH2)2-COO-, -(CH2)2-OCO-, -O-CO-(CH2)2-, and -COO-(CH2)2-, and the others are single bonds.

[0728] Sp p1 and Sp p2 Each independently represents a spacer. p1 and Sp p2 The spacer represented by is preferably a single bond or an alkylene group having 1 to 30 carbon atoms. The -CH2- in the alkylene group may be substituted by -O-, -CO-, -COO-, -OCO-, -CH=CH- or -C≡C- as long as the oxygen atoms are not directly bonded to each other. The hydrogen atoms in the alkylene group may be substituted by halogen atoms. Among them, Sp is preferred.p1 and Sp p2 Each independently represents a linear alkylene group having 1 to 10 carbon atoms or a single bond.

[0729] A p1 , A p2 and A p3 Each independently preferably is a 1,4-phenylene group or a 1,4-cyclohexylene group, and more preferably is a 1,4-phenylene group.

[0730] In order to improve the compatibility with liquid crystal molecules (liquid crystal compounds), the 1,4-phenylene group is preferably substituted with one fluorine atom, one methyl group or one methoxy group.

[0731] The polymerizable liquid crystal composition of the present invention contains a polymerizable compound represented by the general formula (P) in addition to the compound represented by the general formula (i), and thereby can appropriately form a pretilt angle of the liquid crystal molecules.

[0732] Specific examples of the polymerizable compound represented by the general formula (P) include compounds represented by the following formulae (P-2-1) to (P-2-20).

[0733] [Chemistry 151]

[0734]

[0735] [Chemistry 152]

[0736]

[0737] The total content of the compounds represented by the general formula (P) is preferably 0.05 to 10 mass % relative to the polymerizable liquid crystal composition, more preferably 0.1 to 8 mass %, further preferably 0.1 to 5 mass %, further preferably 0.1 to 3 mass %, further preferably 0.2 to 2 mass %, further preferably 0.2 to 1.3 mass %, particularly preferably 0.2 to 1 mass %, and most preferably 0.2 to 0.56 mass %.

[0738] The preferred lower limit of the total content of the compounds represented by the general formula (P) is 0.01 mass%, 0.03 mass%, 0.05 mass%, 0.08 mass%, 0.1 mass%, 0.15 mass%, 0.2 mass%, 0.25 mass%, 0.3 mass% relative to the polymerizable liquid crystal composition. The preferred upper limit of the total content of the compounds represented by the general formula (P) is 10 mass%, 8 mass%, 5 mass%, 3 mass%, 1.5 mass%, 1.2 mass%, 1 mass%, 0.8 mass%, 0.5 mass% relative to the polymerizable liquid crystal composition.

[0739] If the content of the compound represented by the general formula (P) is small, it is difficult to show the effect of adding the compound to the liquid crystal composition. For example, there are situations where the orientation control force of the liquid crystal molecules is weak, or the orientation control force of the liquid crystal molecules weakens over time, etc., depending on the type of liquid crystal molecules and orientation aids. On the other hand, if the content of the compound represented by the general formula (P) is too much, for example, according to the illumination of the active energy line, there are situations where the amount of the compound remaining after curing becomes more, the curing is time-consuming, and the reliability of the liquid crystal composition is reduced. Therefore, it is preferred to set its content in consideration of these balances.

[0740] Furthermore, the polymerizable liquid crystal composition of the present invention may further contain a known spontaneous alignment aid for liquid crystal compositions in addition to the compound represented by the general formula (i).

[0741] D. Others

[0742] The lower limit of the total content of the compound represented by the general formula (i), the compound represented by the general formula (L), and the compound represented by the general formula (N) relative to the total amount of the composition used in the liquid crystal layer of the liquid crystal display element of the present invention is preferably 80%, 85%, 88%, 90%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 100%. In addition, the upper limit of the above content is preferably 100%, 99%, 98%, 95%.

[0743] The lower limit of the total content of the compound represented by the general formula (i), the compound represented by the general formulae (L-1) to (L-6), and the compound represented by the general formulae (N-1) to (N-3) relative to the total amount of the composition used in the liquid crystal layer of the liquid crystal display element of the present invention is preferably 80%, 85%, 88%, 90%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 100%. In addition, the upper limit of the above content is preferably 100%, 99%, 98%, 95%.

[0744] II. Liquid crystal display element

[0745] A liquid crystal display element according to one embodiment of the present invention (hereinafter referred to as the liquid crystal display element of the present invention) comprises: two substrates, and a resin component formed by curing the compound represented by the general formula (i) in the polymerizable liquid crystal composition described in the above-mentioned “I. Polymerizable liquid crystal composition” between the two substrates.

[0746] The so-called resin component formed by curing the compound represented by the general formula (i) may be referred to as a polymer of the compound represented by the general formula (i). Therefore, the liquid crystal display element of the present invention comprises: a first substrate, a second substrate, and a liquid crystal layer disposed between the first substrate and the second substrate and containing at least a liquid crystal composition and a polymer of the compound represented by the general formula (i). The liquid crystal layer may also contain unpolymerized compounds represented by the general formula (i).

[0747] According to the liquid crystal display element of the present invention, the liquid crystal layer contains a polymer and a liquid crystal composition of a compound represented by the general formula (i), and the liquid crystal molecules contained in the liquid crystal composition can be spontaneously oriented by the interaction between the polymer of the compound represented by the general formula (i) and the non-polymerizable liquid crystal molecules. Therefore, the liquid crystal molecules in the liquid crystal composition sandwiched between two substrates can be uniformly and vertically oriented to the substrate even if an alignment film (PI layer) is not provided, and good orientation stability can be displayed. In addition, the polymer of the compound represented by the general formula (i) is firmly biased in the substrate that clamps the liquid crystal composition, thereby improving the stability of the pretilt angle through the above-mentioned resin component. Thus, the liquid crystal display element of the present invention has no drip marks, uneven orientation, or the drip marks and uneven orientation are reduced to an acceptable level, and can have excellent long-term display characteristics that afterimages are difficult to generate.

[0748] Since the liquid crystal display element of the present invention has a resin component formed by curing the compound represented by general formula (i) between the two substrates (the first substrate and the second substrate), it is not necessary to provide an alignment film such as a PI layer on the liquid crystal layer side of the first substrate and the second substrate. That is, the liquid crystal display element of the present invention can be formed into a configuration in which at least one of the two substrates does not have an alignment film, or both substrates do not have an alignment film.

[0749] The liquid crystal display element of the present invention may be an active matrix driven liquid crystal display element. In addition, the liquid crystal display element of the present embodiment may be a PSA type, PSVA type, VA type, IPS type, FFS type or ECB type liquid crystal display element, preferably a PSA type or PSVA type liquid crystal display element. The VA type liquid crystal display element may be a general VA type, a TN-VA type, or a chiral VA type having a liquid crystal layer further containing a chiral agent.

[0750] As a specific form of the liquid crystal display element of the present invention, for example, the following forms can be cited, namely, having: a first substrate and a second substrate arranged opposite to each other; a liquid crystal layer filled between the first substrate and the second substrate; an electrode layer on the first substrate, which has a plurality of gate bus lines and data bus lines arranged in a matrix in each pixel, a thin film transistor arranged at the intersection of the gate bus line and the data bus line, and a pixel electrode driven by the thin film transistor; a common electrode formed on the first substrate or the second substrate; a resin component located between the first substrate and the second substrate and cured by at least the compound represented by the general formula (i). The liquid crystal display element of this form may not have an orientation film on at least one substrate surface, or may not have an orientation film on both substrate surfaces of the first substrate and the second substrate.

[0751] In the liquid crystal display element of the present invention, there is a first resin component formed by curing the compound represented by the general formula (i) between the first substrate and the second substrate. In addition to the first resin component, there may also be a second resin component formed by curing the compound represented by the general formula (P) (a polymer of the polymerizable compound represented by the general formula (P)).

[0752] III. Compounds

[0753] The compound according to one embodiment of the present invention (hereinafter referred to as the compound of the present invention) is represented by the general formula (i).

[0754] According to the compound of the present invention, since it has a desired structure represented by the general formula (i), it has good compatibility with a liquid crystal composition, and can uniformly align liquid crystal molecules in the liquid crystal composition vertically and impart a stable pretilt angle.

[0755] The details and specific examples of the compounds represented by general formula (i) are the same as those described in the above-mentioned section “I. Polymerizable liquid crystal composition A. Compounds represented by general formula (i)”, and therefore the description here is omitted.

[0756] The following is a production example of the compound represented by general formula (i). In the following description, "compound X" or "compound of formula (X)" means "compound represented by formula (X)".

[0757] (Preparation Method 1) Preparation of a Compound Represented by General Formula (i-a)

[0758] In N,N-dimethylformamide, (5-(bromomethyl)2-,2-dimethyl-1,3-dioxane-5-yl)methanol is reacted with benzyl bromide in the presence of potassium carbonate to obtain compound (S-1). Then, in dichloromethane, in the presence of triethylamine, methyl oxalyl chloride is reacted with compound (S-1) to obtain compound (S-2). Next, in N,N-dimethylformamide, in the presence of potassium carbonate, compound (S-2) is reacted with 4-chloro-2,6-bis(hydroxypropyl)phenol to obtain compound (S-3). Furthermore, in tetrahydrofuran, in the presence of palladium carbon, under a hydrogen atmosphere, compound (S-4) is obtained. Then, in a dichloromethane solvent, in the presence of triethylamine, the compound (S-4) is subjected to an esterification reaction using methacrylic acid chloride to obtain a compound (S-5). Finally, in tetrahydrofuran, in the presence of potassium carbonate and tetrakis(triphenylphosphine)palladium(0), the compound (S-5) is reacted with a boron compound to obtain the target compound (i-a).

[0759] [Chemistry 153]

[0760]

[0761] (In the above formula, S pi3 , S pi4 , R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 It represents the same as S in the general formula (i) pi3 , S pi4 , R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 Same meaning).

[0762] (Preparation Method 2) Preparation of a Compound Represented by General Formula (i-b)

[0763] Compound (S-1) obtained by Preparation Method 1 is reacted with methyl malonate chloride in dichloromethane in the presence of triethylamine to obtain compound (S-6). In addition, a boron compound is reacted with 4-chloro-2,6-bis(hydroxypropyl)phenol in tetrahydrofuran in the presence of potassium carbonate and tetrakis(triphenylphosphine)palladium(0) to obtain compound (S-7). Next, compound (S-7) is reacted with compound (S-6) in N,N-dimethylformamide in the presence of potassium carbonate to obtain compound (S-8). Furthermore, compound (S-8) is reacted in tetrahydrofuran in the presence of palladium on carbon under a hydrogen environment to obtain compound (S-9). Finally, compound (S-9) is subjected to an esterification reaction using methacryloyl chloride in a dichloromethane solvent in the presence of triethylamine to obtain the target compound (i-b).

[0764] [Chemistry 154]

[0765]

[0766] (In the above formula, S pi3 , S pi4 , R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 It represents the same as S in the general formula (i) pi3 , S pi4 , R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 Same meaning).

[0767] (Preparation Method 3) Preparation of a Compound Represented by General Formula (i-c)

[0768] In toluene, pentaerythritol and triethyl orthoacetate are reacted in the presence of p-toluenesulfonic acid monohydrate to obtain compound (S-10). Next, in a dichloromethane solvent, in the presence of triethylamine, methanesulfonyl chloride is reacted with compound (S-10) to obtain compound (S-11). Then, in N,N-dimethylformamide, in the presence of potassium carbonate, compound (S-11) is reacted with compound (S-7) obtained in Preparation Method 2 to obtain compound (S-12). Furthermore, in a dichloromethane solvent, in the presence of triethylamine, compound (S-12) is subjected to an esterification reaction using methacryloyl chloride to obtain compound (S-13). Finally, compound (S-13) is reacted in a mixed solvent of tetrahydrofuran and water in the presence of concentrated hydrochloric acid to obtain the target compound (i-c).

[0769] [Chemistry 155]

[0770]

[0771] (In the above formula, R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 Respectively represent R in the general formula (i) i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 Same meaning).

[0772] (Preparation Method 4) Preparation of a Compound Represented by General Formula (i-d)

[0773] Compound (S-7) obtained in Preparation Method 2 is reacted with benzyl bromide in N,N-dimethylformamide in the presence of potassium carbonate to obtain compound (S-14). Next, compound (S-14) is reacted with 4-dihydro-2H-pyran in a dichloromethane solvent in the presence of pyridinium p-toluenesulfonate to obtain compound (S-15). Then, compound (S-15) is reacted in tetrahydrofuran in the presence of palladium carbon under a hydrogen environment to obtain compound (S-16). Furthermore, compound (S-17) is reacted with compound (S-16) in N,N-dimethylformamide in the presence of potassium carbonate to obtain compound (S-18). Next, methyl chlorooxalyl ester is reacted with compound (S-18) in dichloromethane in the presence of triethylamine to obtain compound (S-19). Then, compound (S-19) is reacted in a mixed solvent of tetrahydrofuran and water in the presence of concentrated hydrochloric acid to obtain compound (S-20). Finally, compound (S-20) is subjected to an esterification reaction using methacryloyl chloride in the presence of triethylamine in a dichloromethane solvent to obtain the target compound (i-d).

[0774] [Chemistry 156]

[0775]

[0776] (In the above formula, S pi4 , R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 It represents the same as S in the general formula (i) pi4 , R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 Same meaning).

[0777] (Preparation Method 5) Preparation of a Compound Represented by General Formula (i-e)

[0778] Compound (S-21) is obtained by reacting 4-bromo-5-ethyl-2-(3-hydroxypropyl)phenol in ethyl acetate in the presence of p-toluenesulfonic acid monohydrate. Compound (S-21) is then reacted with a boron compound in tetrahydrofuran in the presence of potassium carbonate and tetrakis(triphenylphosphine)palladium(0) to obtain compound (S-22). Compound (S-22) is then reacted with trifluoromethanesulfonic anhydride in dichloromethane in the presence of pyridine to obtain compound (S-23). ​​Compound (S-23) is then reacted with bis(pinacolato)diboron in N,N-dimethylformamide in the presence of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and potassium acetate to obtain compound (S-24). Next, compound (S-24) is reacted with 4-bromo-2-(3-hydroxypropyl)phenol in tetrahydrofuran in the presence of potassium carbonate and tetrakis(triphenylphosphine)palladium(0) to obtain compound (S-25). Next, compound (S-25) is hydrolyzed in a mixed solvent of tetrahydrofuran and water in the presence of sodium hydroxide to obtain compound (S-26). Then, compound (S-26) is reacted with compound (S-6) in N,N-dimethylformamide in the presence of potassium carbonate to obtain compound (S-27). Furthermore, compound (S-27) is reacted in tetrahydrofuran in the presence of palladium carbon under a hydrogen atmosphere to obtain compound (S-28). Finally, compound (S-28) is subjected to an esterification reaction using methacryloyl chloride in a dichloromethane solvent in the presence of triethylamine to obtain the target compound (i-e).

[0779] [Chemistry 157]

[0780]

[0781] (In the above formula, S pi3 , S pi4 , R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 It represents the same as S in the general formula (i) pi3 , S pi4 , R i1 、m i1 , A i1 , Z i1 , A i2 and Z i2 Same meaning).

[0782] Example

[0783] Hereinafter, the present invention will be described in further detail based on examples, but the present invention is not limited to the examples. In the following examples and comparative examples, "%" means "mass %".

[0784] (Compound Labeling)

[0785] The following abbreviations are used for the ring structures in the compounds.

[0786] [Chemistry 158]

[0787]

[0788] The following abbreviations are used for the side chain structures in the compounds. n in the table is a natural number.

[0789] [Table 1]

[0790] Aliases Chemical structure -n <![CDATA[-C n H 2n+1 ]]> n- <![CDATA[C n H 2n+1 -]]> -On <![CDATA[-oC n H 2n+1 ]]> nO- <![CDATA[C n H 2n+1 O-]]> -V <![CDATA[-CH=CH2]]> V- <![CDATA[CH2=CH-]]> -Vl <![CDATA[-CH=CH-CH3]]> 1V- <![CDATA[CH3-CH=CH-]]> -2V <![CDATA[-CH2-CH2-CH=CH2]]> V2- <![CDATA[CH2=CH-CH2CH z -]]> -2V1 <![CDATA[-CH2-CH2-CH=CH-CH3]]> 1V2- <![CDATA[CH3-CH=CH-CH2-CH2-]]>

[0791] The following abbreviations are used for the connection structures in the compounds. n in the table is a natural number.

[0792] [Table 2]

[0793] Aliases Chemical structure -n- <![CDATA[-C n H 2n -]]> -nO- <![CDATA[-C n H 2n O-]]> -On- <![CDATA[-OC n H 2n -]]> -COO- -C(=O)-O- -OCO- -OC(=O)- -V- -CH=CH- -nV- <![CDATA[-C n H 2n -CH=CH-]]> -Vn- <![CDATA[-CH=CH-C n H 2n -]]> -T- -C≡C- -CF2O- <![CDATA[-CF2-O-]]> -OCF2- <![CDATA[-O-CF2-]]>

[0794] (physical properties)

[0795] The physical properties measured in Examples and Comparative Examples are shown below.

[0796] Tni: Nematic-isotropic liquid phase transition temperature (°C)

[0797] Δn: refractive index anisotropy at 20°C

[0798] η: Viscosity at 20°C (mPa·s)

[0799] γ1: Rotational viscosity at 20°C (mPa·s)

[0800] Δε: Dielectric anisotropy at 20°C

[0801] K 33 : Elastic constant K at 20°C 33 (pN)

[0802] (Evaluation Test)

[0803] Hereinafter, the details of the evaluation tests carried out in Examples and Comparative Examples will be described.

[0804] (1) Evaluation test of low temperature stability

[0805] The polymerizable liquid crystal composition was filtered using a membrane filter (manufactured by Agilent Technologies, PTFE 13 mm-0.2 μm) and allowed to stand for 15 minutes under vacuum decompression conditions to remove dissolved air. It was washed with acetone, and 0.5 g was weighed in a well-dried vial and allowed to stand at a low temperature of -25°C. Then, the presence or absence of precipitation was visually observed and judged in the following 4 stages.

[0806] A: After standing for 14 days, no precipitation was observed.

[0807] B: After leaving the mixture to stand for 7 days, precipitation was observed.

[0808] C: After standing for 3 days, precipitation was confirmed.

[0809] D: After standing for 1 day, precipitation was confirmed.

[0810] (2) Vertical orientation evaluation test

[0811] A first substrate (common electrode substrate) of 4 cm square having a transparent electrode layer and a color filter layer composed of a transparent common electrode but without an orientation film, and a corresponding second substrate (pixel electrode substrate) having a pixel electrode layer with a transparent pixel electrode driven by an active element but without an orientation film are prepared.

[0812] The sealing material is drawn on the periphery of the first substrate, and the polymerizable liquid crystal composition is further dripped, and the second substrate is laminated and clamped under vacuum, and the sealing material is cured at 110°C for 1 hour at normal pressure to obtain a liquid crystal cell with a cell gap of 3.2 μm. The dripping pattern at this time is a mandatory test in the orientation test, such as Figure 1 As shown, 1 point is set to 4.2 μL and 5 points are dripped. The uniformity of the vertical alignment and the presence or absence of drop marks in the liquid crystal cell prepared in the above manner are observed using a polarizing microscope and evaluated in the following 5 stages. In addition, in this evaluation, the surface treatment time in the previous production of our company was reduced, and the orientation test was emphasized for evaluation.

[0813] S: No drip marks or uneven orientation, including at the ends, and excellent vertical orientation over the entire surface

[0814] A: There are no drip marks or uneven orientation on the entire surface, including the edges, and uniform vertical orientation is confirmed over the entire surface

[0815] B: There are very slight drip marks and uneven orientation, but the degree is acceptable.

[0816] C: There are many drip marks including the ends, and the orientation is uneven, which is unacceptable

[0817] D: Drip marks, uneven orientation, poor orientation before evaluation, very severe

[0818] (3) Evaluation test of pretilt angle formation

[0819] While applying a rectangular AC wave of 10 V and 100 Hz to the liquid crystal cell used in the above "(2) Evaluation Test of Vertical Alignment"), the liquid crystal cell was irradiated with an illuminance of 100 m / cm at 365 nm using a high pressure mercury lamp. 2 Then, a physical external force was applied to the cell while applying a 10V, 100Hz rectangular AC wave, and after standing for several minutes, the cell was observed under crossed Nicol prisms, and the stability of the white display was evaluated in the following four stages.

[0820] A: Uniform vertical orientation is confirmed over the entire surface including the edges

[0821] B: There are very slight orientation defects, but the degree is acceptable.

[0822] C: There are many orientation defects including the end, which is unacceptable

[0823] D: Very bad orientation

[0824] (4) Evaluation test of residual monomer amount

[0825] The cell used in the above (pretilt angle formation evaluation test) was further irradiated with a UV fluorescent lamp manufactured by Toshiba Lighting Technology Co., Ltd. for 60 minutes (illuminance at 313 nm: 1.7 mW / cm 2 ) and then the amount of the remaining monomers was quantified by HPLC to determine the amount of the remaining monomers. The following four levels were used for evaluation based on the amount of the remaining monomers.

[0826] A: Less than 300ppm

[0827] B: 300ppm or more and less than 500ppm

[0828] C: 500ppm or more and less than 1500ppm

[0829] D: 1500ppm or more

[0830] (5) Evaluation test of pretilt angle stability

[0831] For the obtained liquid crystal unit, the pretilt angle of the liquid crystal molecules was measured using a pretilt angle measurement system (manufactured by Shintech, "OPTIPRO"). This pretilt angle was set as the initial value. Next, a rectangular voltage of 30V was applied to the liquid crystal unit at a frequency of 100Hz, and light was continuously irradiated from the backlight for 10 hours. Then, the pretilt angle was measured again and set as the pretilt angle (value after the test). Furthermore, the voltage of 30V is several times larger than the usual driving voltage, and it is an accelerated test. The value of the measured pretilt angle (initial value) minus the pretilt angle (value after the test) is taken as the pretilt angle change (= absolute value of the pretilt angle change) [°], and evaluated according to the following criteria. Furthermore, the closer the pretilt angle change is to 0 [°], the lower the possibility of display defects caused by the change in the pretilt angle.

[0832] S: Change within 0.05° (almost no display failure)

[0833] A: Change greater than 0.05° but within 0.1° (hard to cause display failure)

[0834] B: Change greater than 0.1° but within 0.3° (resulting in considerable display failure)

[0835] C: Change greater than 0.3° (display failure occurs, which is an unacceptable level)

[0836] D: Change greater than 0.5° (indicating serious defects, which are completely unacceptable)

[0837] 1. Synthesis of compound of formula (i)

[0838] (Example 1)

[0839] In a reaction container equipped with a stirrer, a cooler, and a thermometer, 42 g of 3-fluoro-4-(4-pentyl(cyclohexyl))phenylboronic acid, 32 g of 4-chloro-2,6-bis(hydroxypropyl)phenol, 27 g of potassium carbonate, 1.5 g of tetrakistriphenylphosphine palladium, and 300 ml of ethanol were added, and the mixture was reacted at 70° C. for 5 hours. After the reaction was completed, the mixture was cooled, 300 ml of ethyl acetate was added, the organic layer was washed with water and saturated saline, the solvent was distilled off, and then recrystallization was performed using toluene to obtain 50 g of the compound represented by formula (1-1).

[0840] [Chemistry 159]

[0841]

[0842] Next, 50 g of the above compound (1-1), 23 g of benzyl bromide, 23 g of potassium carbonate, and 200 ml of acetone were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the mixture was reacted at 50° C. for 24 hours. After the reaction was completed, the mixture was cooled, 250 ml of 10% hydrochloric acid and 300 ml of ethyl acetate were added, the organic layer was washed with water and saturated saline, and the solvent was distilled off. Then, the mixture was purified using a silica gel column to obtain 51 g of the compound represented by formula (1-2).

[0843] [Chemistry 160]

[0844]

[0845] Next, 51 g of the above compound (1-2), 24 g of 3,4-dihydro-2H-pyran, 2 g of pyridinium p-toluenesulfonate, and 280 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the mixture was reacted at room temperature for 2 hours. After the reaction was completed, the mixture was cooled, 200 ml of water was added, the organic layer was washed with a saturated sodium bicarbonate aqueous solution and a saturated saline solution, and the solvent was distilled off. Then, the mixture was purified using a silica gel column to obtain 65 g of the compound represented by formula (1-3).

[0846] [Chemistry 161]

[0847]

[0848] Next, 65 g of the above compound (1-3), 340 ml of tetrahydrofuran (hereinafter referred to as THF), and 6.7 g of palladium carbon were added to a pressure-resistant reaction vessel, and the mixture was reacted for 10 hours under a hydrogen environment (0.5 MPa). After the reaction was completed, the mixture was cooled and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, the mixture was purified using a silica gel column to obtain 54 g of the compound represented by formula (1-4).

[0849] [Chemistry 162]

[0850]

[0851] Next, 54 g of the above compound (1-4), 52 g of 2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol, 36 g of potassium carbonate, and 540 ml of N,N-dimethylformamide were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and reacted at 90°C for 24 hours. After the reaction was completed, the mixture was cooled, 600 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 58 g of the compound represented by formula (1-5).

[0852] [Chemistry 163]

[0853]

[0854] Next, in a reaction container equipped with a stirring device, a cooler, and a thermometer, 58 g of the above compound (1-5), 28 g of triethylamine, and 900 ml of dichloromethane were added, and the reaction container was cooled to below 10°C. Then, 32 g of methyl chlorooxalyl was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 3 hours. After the reaction was completed, it was cooled and 260 ml of water was slowly added dropwise. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 47 g of the compound represented by formula (1-6).

[0855] [Chemistry 164]

[0856]

[0857] Next, in a reaction vessel equipped with a stirring device and a thermometer, 47 g of the above compound (1-6), 470 ml of THF, 47 ml of concentrated hydrochloric acid, and 470 ml of water were added, and the mixture was reacted at 60° C. for 3 hours. After the reaction was completed, the mixture was cooled and 400 ml of a saturated aqueous sodium bicarbonate solution was added. The target product was then extracted using ethyl acetate. The organic layer was washed with water and saturated saline, and the solvent was distilled off. Then, the mixture was purified using a silica gel column to obtain 38 g of the compound represented by formula (1-7).

[0858] [Chemistry 165]

[0859]

[0860] Next, 38 g of the above compound (1-7), 11 g of triethylamine, and 200 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 11 g of methacryloyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, 200 ml of water was slowly added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification using a silica gel column was performed to obtain 35 g of the target compound represented by formula (i-256).

[0861] [Chemistry 166]

[0862]

[0863] (Physical property values ​​of the compound of formula (i-256))

[0864] LC-MS: 969.5 (MS+H); Appearance: oily

[0865] (Example 2)

[0866] In a reaction container equipped with a stirrer, a cooler, and a thermometer, 34 g of pentaerythritol, 41 g of triethyl orthoacetate, 0.2 g of p-toluenesulfonic acid monohydrate, and 25 ml of toluene were added and heated at 80°C. After removing all the generated ethanol, the temperature was raised to distill off the toluene. Then, purification was performed using a silica gel column to obtain 36 g of the compound represented by formula (2-1).

[0867] [Chemistry 167]

[0868]

[0869] Next, 36 g of compound (2-1), 27 g of triethylamine, and 270 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 31 g of methanesulfonyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, it was cooled, 270 ml of water was added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification using a silica gel column was performed to obtain 53 g of the compound represented by formula (2-2).

[0870] [Chemistry 168]

[0871]

[0872] Next, 50 g of compound (1-1), 31 g of compound (2-2), 23 g of potassium carbonate, and 500 ml of N,N-dimethylformamide were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and reacted at 90°C for 24 hours. After the reaction was completed, the mixture was cooled, 600 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, the mixture was purified by a silica gel column to obtain 59 g of the compound represented by formula (2-3).

[0873] [Chemistry 169]

[0874]

[0875] Next, 59 g of the above compound (2-3), 22 g of triethylamine, and 330 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 23 g of methacryloyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, 330 ml of water was slowly added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification using a silica gel column was performed to obtain 65 g of the compound represented by formula (2-4).

[0876] [Chemistry 170]

[0877]

[0878] Next, in a reaction vessel equipped with a stirring device and a thermometer, 65 g of the above compound (2-4), 650 ml of THF, 65 ml of concentrated hydrochloric acid, and 650 ml of water were added, and the mixture was reacted at 60° C. for 3 hours. After the reaction was completed, the mixture was cooled and 650 ml of saturated sodium bicarbonate aqueous solution was added. Then, the target compound was extracted using ethyl acetate. The organic layer was washed with water and saturated saline, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 57 g of the target compound represented by formula (i-6).

[0879] [Chemistry 171]

[0880]

[0881] (Physical property values ​​of the compound of formula (i-6))

[0882] LC-MS: 711.2 (MS+H); Appearance: oily

[0883] (Example 3)

[0884] In a reaction vessel equipped with a stirrer, a cooler, and a thermometer, 30 g of (5-(bromomethyl)2-,2-dimethyl-1,3-dioxane-5-yl)methanol, 24 g of benzyl bromide, 26 g of potassium carbonate, and 150 ml of N,N-dimethylformamide were added, and the mixture was reacted at 50°C for 6 hours. After the reaction was completed, the mixture was cooled, 300 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Next, the extract and 300 ml of THF were added to a reaction vessel equipped with a stirrer and a thermometer, and 30 ml of 10% hydrochloric acid was slowly added dropwise. After the reaction was completed, the mixture was cooled, and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, the mixture was purified using a silica gel column to obtain 32 g of the compound represented by formula (3-1).

[0885] [Chemistry 172]

[0886]

[0887] Next, 32 g of the above compound (3-1), 25 g of triethylamine, and 320 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 32 g of methyl malonyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, water was slowly added, and the mixture was washed with 100 ml of dichloromethane, water, and saturated brine, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 43 g of the compound represented by formula (3-2).

[0888] [Chemistry 173]

[0889]

[0890] Next, 43 g of compound (3-2), 22 g of 4-chloro-2,6-bis(hydroxypropyl)phenol, 24 g of potassium carbonate, and 215 ml of N,N-dimethylformamide were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and reacted at 90°C for 8 hours. After the reaction was completed, the mixture was cooled, 300 ml of ethyl acetate was added, the organic layer was washed with water and saturated saline, and the solvent was distilled off. Then, dispersion washing with toluene and purification with a silica gel column were performed to obtain 42 g of compound represented by formula (3-3).

[0891] [Chemistry 174]

[0892]

[0893] Next, 42 g of the above compound (2-4), 210 ml of THF, and 4.2 g of palladium carbon were added to a pressure-resistant reaction vessel, and the mixture was reacted for 10 hours under a hydrogen environment (0.5 MPa). After the reaction was completed, the mixture was cooled and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, the mixture was purified with a silica gel column to obtain 35 g of the compound represented by formula (3-4).

[0894] [Chemistry 175]

[0895]

[0896] Next, 35 g of the above compound (3-4), 23 g of triethylamine, and 350 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 21 g of methacryloyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, water was slowly added, and the mixture was washed with 100 ml of dichloromethane, water, and saturated brine, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 42 g of the compound represented by formula (3-5).

[0897] [Chemistry 176]

[0898]

[0899] Next, in a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 42 g of the above compound (3-5), 18 g of 3-fluoro-4-(4-pentyl(cyclohexyl))phenylboronic acid, 23 g of potassium carbonate, 3 g of tetrakistriphenylphosphine palladium, 420 ml of THF, and 84 ml of water were added, and the mixture was reacted at 50° C. for 9 hours. After the reaction was completed, the mixture was cooled, 500 ml of ethyl acetate was added, the organic layer was washed with water and saturated saline, the solvent was distilled off, and the mixture was purified by a silica gel column to obtain 21 g of the target compound represented by formula (i-201). This target compound can also be synthesized by the preparation method 2 described in the above “III. Compounds”.

[0900] [Chemistry 177]

[0901]

[0902] (Physical property values ​​of the compound of formula (i-201))

[0903] LC-MS: 979.3 (MS+H); Properties: solid

[0904] (Example 4)

[0905] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 29 g of 2-(benzyloxy)ethanol, 7 g of sodium hydride, and 50 ml of N,N-dimethylformamide were added, and the mixture was reacted at room temperature for 1 hour. Then, 50 g of 2,2-bis(bromomethyl)propane-1,3-diol was slowly added, and the mixture was reacted at 50°C for 10 hours. After the reaction was completed, the mixture was cooled, 100 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, the mixture was purified by a silica gel column to obtain 25 g of the compound represented by formula (4-1).

[0906] [Chemistry 178]

[0907]

[0908] Next, 25 g of the above compound (4-1), 18 g of triethylamine, and 250 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 20 g of methyl chlorooxalyl was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, water was slowly added, and the mixture was washed with 50 ml of dichloromethane, water, and saturated brine, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 28 g of the compound represented by formula (4-2).

[0909] [Chemistry 179]

[0910]

[0911] Next, 28 g of compound (4-2), 14 g of 4-chloro-2,6-bis(hydroxypropyl)phenol, 15 g of potassium carbonate, and 140 ml of N,N-dimethylformamide were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and reacted at 90°C for 8 hours. After the reaction was completed, the mixture was cooled, 200 ml of ethyl acetate was added, the organic layer was washed with water and saturated saline, and the solvent was distilled off. Then, dispersion washing with toluene and purification with a silica gel column were performed to obtain 32 g of the compound represented by formula (4-3).

[0912] [Chemistry 180]

[0913]

[0914] Next, 32 g of the above compound (4-3), 160 ml of THF, and 3.2 g of palladium carbon were added to a pressure-resistant reaction vessel, and the mixture was reacted for 10 hours under a hydrogen environment (0.5 MPa). After the reaction was completed, the mixture was cooled and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, the mixture was purified with a silica gel column to obtain 27 g of the compound represented by formula (4-4).

[0915] [Chemistry 181]

[0916]

[0917] Next, 27 g of the above compound (4-4), 17 g of triethylamine, and 270 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 16 g of methacryloyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, water was slowly added, and the mixture was washed with 80 ml of dichloromethane, water, and saturated brine, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 31 g of the compound represented by compound (4-5).

[0918] [Chemistry 182]

[0919]

[0920] Next, 31 g of the above compound (4-5), 13 g of 3-fluoro-4-(4-pentyl(cyclohexyl))phenylboronic acid, 11 g of potassium carbonate, 2 g of tetrakistriphenylphosphine palladium, 310 ml of THF, and 62 ml of water were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the mixture was reacted at 50° C. for 9 hours. After the reaction was completed, the mixture was cooled, 400 ml of ethyl acetate was added, the organic layer was washed with water and saturated saline, the solvent was distilled off, and the mixture was purified by silica gel column to obtain 23 g of the target compound represented by formula (i-621).

[0921] [Chemistry 183]

[0922]

[0923] (Physical property values ​​of the compound of formula (i-621))

[0924] LC-MS: 995.7 (MS+H); Appearance: oily

[0925] (Example 5)

[0926] In a reaction container equipped with a stirring device, a cooler, and a thermometer, 30 g of 1-bromo-2-ethyl-4-methoxybenzene, 45 g of 3-fluoro-4-(4-pentyl(cyclohexyl))phenylboronic acid, 39 g of potassium carbonate, 8 g of tetrakistriphenylphosphine palladium, 300 ml of THF, and 60 ml of water were added, and the mixture was reacted at 50° C. for 9 hours. After the reaction was completed, the mixture was cooled, 400 ml of ethyl acetate was added, the organic layer was washed with water and saturated saline, the solvent was distilled off, and the mixture was purified by silica gel column to obtain 45 g of the compound represented by formula (5-1).

[0927] [Chemistry 184]

[0928]

[0929] Next, 45 g of the above compound (5-1) and 320 ml of dichloromethane were added, and 44 g of boron tribromide was slowly added dropwise, and the mixture was allowed to react for 8 hours. After the reaction was completed, the mixture was cooled, 250 mL of 5° C. water was added dropwise, the organic layer was washed with water and saturated saline, and the solvent was distilled off. Then, the mixture was purified using a silica gel column to obtain 41 g of the compound represented by formula (5-2).

[0930] [Chemistry 185]

[0931]

[0932] Next, 41 g of the above compound (5-2), 210 ml of dichloromethane, and 18 g of pyridine were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. 38 g of trifluoromethanesulfonic anhydride was slowly added dropwise and allowed to react for 5 hours. After the reaction was completed, the mixture was cooled, 250 mL of 5°C water was added dropwise, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 50 g of the compound represented by formula (5-3).

[0933] [Chemistry 186]

[0934]

[0935] Next, 50 g of the compound (5-3), 26 g of bis-pinacolato diborane, 15 g of potassium acetate, 4 g of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and 250 ml of N,N-dimethylformamide were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the mixture was reacted at 50° C. for 15 hours. After the reaction was completed, the mixture was cooled, 500 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, the solvent was distilled off, and the mixture was purified by silica gel column to obtain 30 g of the compound represented by formula (5-4).

[0936] [Chemistry 187]

[0937]

[0938] Next, 46 g of the compound represented by the formula (5-5) was obtained in the same manner as in the above-mentioned compound (3-5).

[0939] [Chemistry 188]

[0940]

[0941] Next, 30 g of the above compound (5-4), 46 g of the above compound (5-5), 17 g of potassium carbonate, 4 g of tetrakistriphenylphosphine palladium, 150 ml of THF, and 30 ml of water were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the mixture was reacted at 60° C. for 20 hours. After the reaction was completed, the mixture was cooled, 300 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, the solvent was distilled off, and the mixture was purified by silica gel column to obtain 23 g of the target compound represented by formula (i-277).

[0942] [Chemistry 189]

[0943]

[0944] (Physical property values ​​of the compound of formula (i-277))

[0945] LC-MS: 1055.4 (MS+H); Properties: solid; 1 H-NMR (solvent: deuterated chloroform): δ: 0.90 (t, 3H), 1.02-1.15 (m, 5H), 1.21-1.37 (m, 9H), 1.43-1.53 ​​(m, 2H), 1.87-2.07 (m, 17H), 2.49-2.62 (m, 3H), 2.75 (t, 4H), 3.92 (s, 6H), 3.98 (s, 2H), 4.17 (t, 4H) ,4.44(s,2H),4.59(s,4H),5.54(s,2H),5.65(s,1H),6.07(s,2H),6.14(s,1H),6.98-7.05 (m,2H),7.15-7.19(m,1H),7.22-7.25(m,1H),7.30(s,2H),7.36-7.38(m,1H),7.44(s,1H)

[0946] (Example 6)

[0947] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 21 g of 2-chloroethanol, 40 g of triethyl methanetricarboxylate, 36 g of potassium carbonate, and 400 ml of THF were added, and the mixture was reacted at 50° C. for 24 hours. After the reaction was completed, the mixture was cooled, 200 ml of water was added dropwise, and 500 ml of ethyl acetate was added. The organic layer was washed with water and saturated brine, the solvent was distilled off, and purification was performed using a silica gel column to obtain 45 g of the compound represented by formula (6-1).

[0948] [Chemistry 190]

[0949]

[0950] Next, 45 g of compound (6-1), 25 g of triethylamine, and 450 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 21 g of methanesulfonyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, it was cooled, 450 ml of water was added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification using a silica gel column was performed to obtain 49 g of the compound represented by formula (6-2).

[0951] [Chemistry 191]

[0952]

[0953] Separately, in a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 20 g of 4-bromo-2-ethylphenol, 30 g of 4-(4-pentyl(cyclohexyl))phenylboronic acid, 82 g of potassium carbonate, 11 g of tetrakistriphenylphosphine palladium, 300 ml of THF, and 60 ml of water were added, and the mixture was reacted at 50° C. for 9 hours. After the reaction was completed, the mixture was cooled, 400 ml of ethyl acetate was added, the organic layer was washed with water and saturated saline, the solvent was distilled off, and the mixture was purified by silica gel column to obtain 57 g of the compound represented by formula (6-3).

[0954] [Chemistry 192]

[0955]

[0956] Next, 67 g of the compound represented by the formula (6-4) was obtained by the same method as the above-mentioned compound (5-3).

[0957] [Chemistry 193]

[0958]

[0959] Next, 50 g of the compound represented by the formula (6-5) was obtained by the same method as that of the above compound (5-4).

[0960] [Chemistry 194]

[0961]

[0962] Next, 44 g of the compound represented by the formula (6-6) was obtained by the same method as that of the above compound (1-1).

[0963] [Chemistry 195]

[0964]

[0965] Next, 53 g of a compound represented by the formula (6-7) was obtained from the compound (6-2) and the compound (6-6) in the same manner as for the above compound (2-3).

[0966] [Chemistry 196]

[0967]

[0968] Next, 13 g of lithium aluminum hydride and 530 ml of THF were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and the mixture was allowed to react for 8 hours under reflux. After the reaction was completed, the mixture was cooled, 700 ml of ethyl acetate was added, the organic layer was washed with water and saturated saline, and the solvent was distilled off. Purification was performed using a silica gel column to obtain 33 g of the compound represented by formula (6-8).

[0969] [Chemistry 197]

[0970]

[0971] Next, by the same method as the above-mentioned compound (2-1), 17g of compound represented by formula (6-9) was obtained.

[0972] [Chemistry 198]

[0973]

[0974] Next, 18 g of a compound represented by the formula (6-10) was obtained by the same method as for the above compound (2-4).

[0975] [Chemistry 199]

[0976]

[0977] Next, 10 g of the target compound represented by formula (i-576) was obtained by the same method as for the above compound (2-4).

[0978] [Chemistry 200]

[0979]

[0980] (Physical property values ​​of the compound of formula (i-576))

[0981] LC-MS: 811.7 (MS+H); Appearance: oily

[0982] (Example 7)

[0983] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 30 g of (chloromethoxymethyl)benzene, 30 g of diethyl malonate, 7 g of sodium hydride, and 300 ml of THF were added, and the mixture was reacted at 50° C. for 24 hours. After the reaction was completed, the mixture was cooled, 200 ml of water was added dropwise, and 300 ml of ethyl acetate was added. The organic layer was washed with water and saturated brine, the solvent was distilled off, and purification was performed using a silica gel column to obtain 26 g of the compound represented by formula (7-1).

[0984] [Chemistry 201]

[0985]

[0986] Next, 26 g of compound (7-1), 29 g of 2-(2-bromoethoxy)tetrahydro-2H-pyran, 26 g of potassium carbonate, and 260 ml of THF were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and reacted at 50° C. for 24 hours. After the reaction was completed, the mixture was cooled, 150 ml of water was added dropwise, and 300 ml of ethyl acetate was added. The organic layer was washed with water and saturated brine, the solvent was distilled off, and purification was performed using a silica gel column to obtain 36 g of the compound represented by formula (7-2).

[0987] [Chemistry 202]

[0988]

[0989] Next, 23 g of a compound represented by the formula (7-3) was obtained by the same method as for the above compound (6-8).

[0990] [Chemistry 203]

[0991]

[0992] Next, 29 g of the compound represented by the formula (7-4) was obtained by the same method as for the above-mentioned compound (4-2).

[0993] [Chemistry 204]

[0994]

[0995] Next, 23 g of a compound represented by the formula (7-5) was obtained by the same method as for the above compound (1-7).

[0996] [Chemistry 205]

[0997]

[0998] Next, 25 g of the compound represented by the formula (7-6) was obtained by the same method as for the above compound (6-2).

[0999] [Chemistry 206]

[1000]

[1001] Next, 30 g of a compound represented by formula (7-7) was obtained from compound (1-1) and compound (7-6) in the same manner as for compound (2-3).

[1002] [Chemistry 207]

[1003]

[1004] Next, 26 g of the compound represented by the formula (7-8) was obtained by the same method as that of the above compound (4-4).

[1005] [Chemistry 208]

[1006]

[1007] Next, 16 g of the target compound represented by formula (i-581) was obtained by the same method as for the above compound (3-5).

[1008] [Chemistry 209]

[1009]

[1010] (Physical property values ​​of the compound of formula (i-581))

[1011] LC-MS: 965.5 (MS+H); Properties: oily

[1012] (Example 8)

[1013] 43 g of the compound represented by the formula (8-1) was obtained from the compound (7-2) in the same manner as for the compound (1-7).

[1014] [Chemistry 210]

[1015]

[1016] Next, 50 g of the compound represented by formula (8-2) was obtained by the same method as that for the above compound (6-2).

[1017] [Chemistry 211]

[1018]

[1019] Next, by the same method as for the above-mentioned compound (2-3), 84 g of a compound represented by the formula (8-3) was obtained from the compound (6-6) and the compound (8-2).

[1020] [Chemistry 212]

[1021]

[1022] Next, 58g of the compound represented by the formula (8-4) was obtained by the same method as the above-mentioned compound (6-8).

[1023] [Chemistry 213]

[1024]

[1025] Next, 50 g of the compound represented by the formula (8-5) was obtained by the same method as that for the above compound (4-4).

[1026] [Chemistry 214]

[1027]

[1028] Next, 50 g of the above compound (8-5), 23 g of triethylamine, and 500 ml of dichloromethane were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and the reaction container was cooled to below 10°C. Then, 23 g of methacryloyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, 500 ml of water was slowly added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification using a silica gel column was performed to obtain 9 g of the target compound represented by formula (i-571).

[1029] [Chemistry 215]

[1030]

[1031] (Physical property values ​​of the compound of formula (i-571))

[1032] LC-MS: 879.5 (MS+H); Appearance: oily

[1033] (Example 9)

[1034] In a reaction container equipped with a stirring device, a cooler, and a thermometer, 50 g of 2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol, 89 g of triethylamine, and 500 ml of dichloromethane were added, and the reaction container was cooled to below 10°C. Then, 75 g of acryloyl chloride was slowly added dropwise. After the addition was completed, the reaction container was returned to room temperature and allowed to react for 6 hours. After the reaction was completed, 500 ml of water was slowly added, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification using a silica gel column was performed to obtain 82 g of the compound represented by formula (9-1).

[1035] [Chemistry 216]

[1036]

[1037] Next, 31 g of polyoxymethylene, 51 g of 1,4-diazabicyclo[2,2,2]octane, and 450 ml of water were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and stirred at room temperature for 15 minutes. 82 g of the above compound (9-1) dissolved in 1000 ml of THF was slowly added dropwise thereto. After the addition was completed, the mixture was reacted for 72 hours. After the reaction was completed, water was slowly added, and extraction was performed using ethyl acetate, and the solvent was distilled off. Then, purification was performed using a silica gel column to obtain 15 g of the compound represented by formula (9-2).

[1038] [Chemistry 217]

[1039]

[1040] Next, by the same method as the above-mentioned compound (1-3), 21 g of the compound represented by the formula (9-3) was obtained.

[1041] [Chemistry 218]

[1042]

[1043] Next, by the same method as for the above-mentioned compound (3-3), 22 g of a compound represented by the formula (9-4) was obtained from 21 g of the compound (9-3) and 7 g of 4-chloro-2,6-bis(hydroxypropyl)phenol.

[1044] [Chemistry 219]

[1045]

[1046] Next, 20 g of the compound represented by the formula (9-5) was obtained by the same method as that for the above-mentioned compound (3-5).

[1047] [Chemistry 220]

[1048]

[1049] Next, the same method as for the above-mentioned compound (1-7) was used to obtain 13g of the compound represented by the formula (9-6).

[1050] [Chemistry 221]

[1051]

[1052] In addition, 30 g of 1-bromo-4-pentylbenzene, 18 g of 1-ethynyl-4-methoxybenzene, 8 g of tetrakistriphenylphosphine palladium, 2 g of copper iodide, and 300 ml of triethylamine were added to a reaction container equipped with a stirring device, a cooler, and a thermometer, and reacted at 50° C. for 24 hours. After the reaction was completed, 500 ml of water was slowly added, the organic layer was washed with water and saturated saline, and the solvent was distilled off. Then, purification using a silica gel column was performed to obtain 29 g of the compound represented by formula (9-7).

[1053] [Chemistry 222]

[1054]

[1055] Next, 27 g of the compound represented by the formula (9-8) was obtained by the same method as that for the above-mentioned compound (1-4).

[1056] [Chemistry 223]

[1057]

[1058] Next, 24 g of a compound represented by the formula (9-9) was obtained by the same method as for the above compound (5-2).

[1059] [Chemistry 224]

[1060]

[1061] Next, 33 g of a compound represented by the formula (9-10) was obtained by the same method as for the above compound (5-3).

[1062] [Chemistry 225]

[1063]

[1064] Next, 25 g of the compound represented by the formula (9-11) was obtained by the same method as that for the above compound (5-4).

[1065] [Chemistry 226]

[1066]

[1067] Next, the same method as that for the above-mentioned compound (i-621) was used to obtain compound 7g represented by formula (i-646).

[1068] [Chemistry 227]

[1069]

[1070] (Physical property values ​​of the compound of formula (i-646))

[1071] LC-MS: 967.4 (MS+H); Properties: oily

[1072] (Examples 10-11)

[1073] By referring to the above methods, the target compounds represented by formula (i-51) and formula (i-651) were obtained respectively.

[1074] [Chemistry 228]

[1075]

[1076] (Example 12)

[1077] From the above compound (1-1) and the above compound (8-2), 26 g of the compound represented by the formula (12-1) can be obtained by the same method as that for the above compound (2-3).

[1078] [Chemistry 229]

[1079]

[1080] Next, the same method as that for the above-mentioned compound (6-8) was used to obtain 18g of the compound represented by the formula (12-2).

[1081] [Chemistry 230]

[1082]

[1083] Next, by the same method as the above-mentioned compound (4-4), 15 g of the compound represented by the formula (12-3) was obtained.

[1084] [Chemistry 231]

[1085]

[1086] Next, 4 g of the target compound represented by formula (i-561) was obtained by the same method as that for the above compound (i-571).

[1087] [Chemistry 232]

[1088]

[1089] (Physical property values ​​of the compound of formula (i-561))

[1090] LC-MS: 793.5 (MS+H); Appearance: oily

[1091] The following is a list of the compounds of formula (i) obtained in Examples 1 to 12. i1 , Pi2 and P i3 The number of (polymerizable groups), T k1 and T k2 The number of polar groups and P i1 , P i2 , P i3 , T k1 and T k2 The total amount is shown in Table 3 below.

[1092] [Chemistry 233]

[1093]

[1094] [Table 3]

[1095]

[1096] 2. Preparation of polymerizable liquid crystal composition

[1097] (Example C1)

[1098] When 100 parts by mass of a liquid crystal composition HLC-1 having the compounds and mixing ratios shown in Table 4 below was added, 0.3 parts by mass of the following polymerizable compound (R-1-0) was added and dissolved by heating to obtain a base composition LC-1.

[1099] [Table 4]

[1100]

[1101] [Chemistry 234]

[1102]

[1103] Next, 0.3 parts by mass of the compound (i-571) synthesized in Example 8 was added to 100 parts by mass of LC-1 and dissolved by heating to prepare a polymerizable liquid crystal composition. The above-mentioned evaluation tests were performed on the obtained polymerizable liquid crystal composition. The results are shown in Table 6.

[1104] (Examples C2 to C24)

[1105] The compounds of formula (i) synthesized in Examples 1 to 12 were added to 100 parts by mass of LC-1 in the amounts shown in Table 5 below, and dissolved by heating to prepare polymerizable liquid crystal compositions of Examples C2 to C24. The above-mentioned evaluation tests were performed on the obtained polymerizable liquid crystal compositions. The results are shown in Table 6.

[1106] [Table 5]

[1107]

[1108] [Table 6]

[1109]

[1110] (Examples C25 to C84)

[1111] Liquid crystal compositions HLC-2 to HLC-8 composed of the compounds and mixing ratios shown in Table 7 below were prepared.

[1112] [Table 7]

[1113]

[1114] When each of the liquid crystal compositions HLC-2 to HLC-8 was 100 parts by mass, a base composition to which 0.3 parts by mass of the polymerizable compound (R-1-0) was added was prepared by heating and dissolving, and these compositions were designated as LC-2 to LC-8, respectively.

[1115] Furthermore, when each of the liquid crystal compositions HLC-1 to HLC-8 was 100 parts by mass, a base composition to which 0.3 parts by mass of the following polymerizable compound (R-1-1) was added by heating and dissolving was prepared, and these base compositions were designated as LC-9 to LC-16.

[1116] [Chemistry 235]

[1117]

[1118] Using any one of LC-2 to LC-16 as a base composition, the compound of formula (i) synthesized in Examples 1 to 12 was added in the amounts shown in Tables 8 and 10 below to 100 parts by mass of the base composition, and the mixture was heated and dissolved, thereby preparing polymerizable liquid crystal compositions of Examples C25 to C84, respectively. The above-mentioned evaluation tests were performed on each of the obtained polymerizable liquid crystal compositions. The results are shown in Tables 9 and 11.

[1119] [Table 8]

[1120]

[1121] [Table 9]

[1122]

[1123] [Table 10]

[1124]

[1125] [Table 11]

[1126]

[1127] As in the above-mentioned Examples C25 to C84, the compounds of formula (i) synthesized in the above-mentioned Examples 1 to 12 were added to the base compositions LC-2 to LC-16 at appropriate concentrations different from the addition amounts in the above-mentioned table relative to 100 parts by mass of the base composition, and the mixture was heated and dissolved, thereby preparing polymerizable liquid crystal compositions respectively. For these polymerizable liquid crystal compositions, the orientation test was evaluated in the same manner as above, and the results, as in the other examples, showed excellent vertical orientation, especially without drip marks and uneven orientation, and excellent pretilt angle stability.

[1128] (Comparative Example RC1)

[1129] A polymerizable liquid crystal composition (ie, basic composition LC-1) was prepared in the same manner as in Example C1 except that the compound of formula (i-571) was not added.

[1130] (Comparative Examples RC2 to RC28)

[1131] A polymerizable liquid crystal composition was prepared in the same manner as in Example C1 except that any one of the following compounds Ref-1 to Ref-6 was added to any one of the base compositions LC-1 to LC-16 in an amount shown in Table 13 below to replace the compound of formula (i-571) relative to 100 parts by mass of the base composition. i1 , P i2 and P i3 The number of (polymerizable groups), T k1 and T k2 The number of polar groups and P i1 , P i2 , P i3 , T k1 and T k2 The total quantity is shown in Table 12 below.

[1132] [Chemistry 236]

[1133]

[1134] [Table 12]

[1135]

[1136] [Table 13]

[1137]

[1138] [Table 14]

[1139]

[1140] As shown above, it was confirmed that, compared with the comparative example composition not containing the compound represented by the general formula (i), the polymerizable liquid crystal composition of the embodiment containing the compound represented by the general formula (i) showed excellent vertical alignment, especially without drip marks and uneven orientation, and excellent pretilt angle stability; it was shown that the display element without an alignment film on at least one side was excellent. In particular, it was shown that T in the general formula (i) k1 and T k2 When the number of (polar groups at specific positions) is large, the orientation is excellent. On the other hand, when the number of P in the general formula (i) is large, the orientation is excellent. i1 , P i2 and P i3 When the number of (polymerizable groups at specific positions) is large, the pretilt angle stability is excellent. In addition, since the amount of residual monomers in the polymerizable liquid crystal composition of the embodiment is small, it can be confirmed that the compound represented by general formula (i) has good low-temperature storage properties and good compatibility with the liquid crystal composition.

Claims

1. A polymerizable liquid crystal composition comprising one or more compounds represented by formula (i-6), (i-51), (i-201), (i-256), (i-277), (i-561), (i-571), (i-576), (i-581), (i-621), (i-646), (i-651), 2 . The polymerizable liquid crystal composition according to claim 1 , comprising a non-polymerizable liquid crystal compound.

3. The polymerizable liquid crystal composition according to claim 2 further contains one or more polymerizable compounds having structures different from those of the formulas (i-6), (i-51), (i-201), (i-256), (i-277), (i-561), (i-571), (i-576), (i-581), (i-621), (i-646), and (i-651).

4. The polymerizable liquid crystal composition according to claim 3, comprising one or more compounds represented by the general formula (P) as polymerizable compounds having a structure different from that of the formulas (i-6), (i-51), (i-201), (i-256), (i-277), (i-561), (i-571), (i-576), (i-581), (i-621), (i-646), and (i-651), [Chemistry 6] In the general formula (P), Z p1 represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkoxy group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkenyl group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, or -Sp p2 -R p2 , R p1 and R p2 Each independently represents any one of the following formula (R-I) to formula (R-VIII), [Chemistry 7] In the formula, In * and Sp p1 Combined, R 2 ~R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, W p represents a single bond, -O- or methylene, T p represents a single bond or -COO-, p, t and q each independently represent 0, 1 or 2, Sp p1 and Sp p2 Each independently represents a spacer, L p1 and L p2 Each independently represents a single bond, -O-, -S-, -CH2-, -OCH2-, -CH2O-, -CO-, -C2H4-, -COO-, -OCO-, -OCOOCH2-, -CH2OCOO-, -OCH2CH2O-, -CO-NR a -, -NR a -CO-, -SCH2-, -CH2S-, -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-, -(CH2) z -C(=O)-O-, -(CH2) z -O-(C=O)-, -O-(C=O)-(CH2) z -, -(C=O)-O-(CH2) z -, -CH2(CH3)C-C(=O)-O-, -CH2(CH3)C-O-(C=O)-, -O-(C=O)-C(CH3)CH2, -(C=O)-O-C(CH3)-CH2, -CH= CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2-, -CF2O-, -OCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2- or -C≡C-, where, R a Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z represents an integer of 1 to 4, M p2 represents 1,4-phenylene, 1,4-cyclohexylene, anthracene-2,6-diyl, phenanthrene-2,7-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-1,4-diyl, naphthalene-2,6-diyl, indane-2,5-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or 1,3-dioxane-2,5-diyl; M p2 unsubstituted or may be substituted with an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or -R p1 replace, M p1 represents any one of the following formulae (i-11) to (ix-11), [Chemistry 8] In the formula, * and Sp p1 or M p1 Combined with L p1 , L p2 , Z p1 or M p1 Combined, M p3 represents any one of the following formulae (i-13) to (ix-13), [Chemistry 9] In the formula, * and Z p1 or L p2 Combined with L p2 Combined, m p2 ~m p4 Each independently represents 0, 1, 2 or 3, m p1 and m p5 Each independently represents 1, 2 or 3, In the presence of multiple Z p1 When there are multiple R p1 When there are multiple R p2 When there are multiple Sp p1 When there are multiple Sp p2 When there are multiple L p1 When there are multiple M p2 When the above-mentioned compounds are used, they may be the same as or different from each other, but do not include the compound represented by claim 1. The polymerizable liquid crystal composition according to claim 4 , wherein the value of dielectric anisotropy Δε is negative.

6. The polymerizable liquid crystal composition according to claim 5, further comprising a compound selected from the group consisting of compounds represented by any one of the general formulae (N-1), (N-2) and (N-3), [Chemistry 10] In the formula, R N11 , R N12 , R N21 , R N22 , R N31 and R N32 Each independently represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent -CH2- in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, A N11 , A N12 , A N21 , A N22 , A N31 and A N32 each independently represents a group selected from the group consisting of the radical (a), the radical (b), the radical (c) and the radical (d), (a) 1,4-cyclohexylene, in which one -CH2- or two or more non-adjacent -CH2- groups may be replaced by -O-, (b) 1,4-phenylene, in which one -CH= or two or more non-adjacent -CH= groups may be substituted with -N=, (c) naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl, in which one -CH= or two or more non-adjacent -CH= groups in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=, and (d) 1,4-cyclohexenylene; The group (a), group (b), group (c) and group (d) may be substituted by a cyano group, a fluorine atom or a chlorine atom, respectively. Z N11 , Z N12 , Z N21 , Z N22 , Z N31 and Z N32 Each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -COO-, -OCO-, -OCF2-, -CF2O-, -CH=N-N=CH-, -CH=CH-, -CF=CF- or -C≡C-, X N21 represents a hydrogen atom or a fluorine atom, T N31 represents -CH2- or oxygen atom, n N11 、n N12 、n N21 、n N22 、n N31 and n N32 Each independently represents an integer from 0 to 3, and n N11 +n N12 、n N21 +n N22 and n N31 +n N32 are independently 1, 2 or 3, In the presence of multiple A N11 ~A N32 , Z N11 ~Z N32 When , they may be the same as or different from each other.

7. A liquid crystal display element comprising: two substrates, and a resin component formed by curing the compounds represented by formula (i-6), (i-51), (i-201), (i-256), (i-277), (i-561), (i-571), (i-576), (i-581), (i-621), (i-646), and (i-651) in the polymerizable liquid crystal composition described in any one of claims 1 to 6 between the two substrates. 8 . The liquid crystal display element according to claim 7 , wherein at least one of the two substrates does not have an alignment film.

9. The liquid crystal display element according to claim 8, comprising: A first substrate and a second substrate are arranged opposite to each other, a liquid crystal layer filled between the first substrate and the second substrate, The electrode layer on the first substrate has, in each pixel, a plurality of gate bus lines and data bus lines arranged in a matrix, a thin film transistor disposed at the intersection of the gate bus lines and the data bus lines, and a pixel electrode driven by the thin film transistor. a common electrode formed on the first substrate or the second substrate, and A resin component located between the first substrate and the second substrate and formed by curing the compound represented by at least the formula (i-6), (i-51), (i-201), (i-256), (i-277), (i-561), (i-571), (i-576), (i-581), (i-621), (i-646), (i-651), No alignment film is provided on at least one substrate surface. 10 . The liquid crystal display element according to claim 7 , which is a PSA type, PSVA type, VA type, IPS type, FFS type or ECB type.

11. A compound represented by formula (i-6), (i-51), (i-201), (i-256), (i-277), (i-561), (i-571), (i-576), (i-581), (i-621), (i-646), (i-651),

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