Polymerizable compound, liquid crystal composition containing polymerizable compound, and liquid crystal display element using the same

Abstract

To provide a polymerizable compound, a liquid crystal composition containing the polymerizable compound, and a liquid crystal display element using the same, where the polymerizable compound can provide a liquid crystal display element excellent in voltage retention, formation of a pretilt angle, and low-temperature storage properties.SOLUTION: The invention provides: a polymerizable compound represented by general formula (i) having at least two hydroxy groups; a polymerizable compound-containing liquid crystal composition containing one or more such polymerizable compounds and one or more liquid crystal compounds; and a liquid crystal display element using the polymerizable compound-containing liquid crystal composition.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polymerizable compound, a liquid crystal composition containing the polymerizable compound, and a liquid crystal display device using the same. [Background technology]

[0002] Liquid crystal display devices are used in a variety of applications, including watches, calculators, measuring instruments, automotive panels, word processors, electronic organizers, printers, computers, televisions, clocks, and advertising displays. Typical liquid crystal display modes include TN (twisted nematic), STN (super twisted nematic), TFT (thin film transistor)-based vertical alignment (VA) and IPS (in-plane switching) modes. Liquid crystal compositions used in these display devices must be stable to external factors such as moisture, air, heat, and light. They must also exhibit a liquid crystal phase over as wide a temperature range as possible, centered around room temperature, have low viscosity, and operate at low voltages. Liquid crystal compositions are composed of several to several dozen compounds to optimize the dielectric anisotropy (Δε) and refractive index anisotropy (Δn) of each display device.

[0003] VA displays use liquid crystal compositions with negative Δε, and are widely used in LCD TVs, etc. Among them, the PSA (polymer-supported alignment) mode is a mode in which a monomer dissolved in the liquid crystal is polymerized to impart a desired pretilt angle to vertically aligned liquid crystal molecules, and is currently the mainstream in TVs because it can achieve a wider viewing angle, fast response, and high transmittance.

[0004] Furthermore, in recent years, there has been a demand for even faster response times for liquid crystal display elements, and liquid crystal compositions that require extremely high characteristics that are a departure from conventional techniques are in demand (Patent Documents 1 and 2). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2014-112192 [Patent Document 2] Japanese Patent Application Laid-Open No. 2010-285499 Summary of the Invention [Problem to be solved by the invention]

[0006] However, liquid crystal compositions are susceptible to degradation by active energy rays such as light emitted from a backlight and ultraviolet rays irradiated during the manufacturing process of liquid crystal display elements, and impurities generated by the photodegradation of the liquid crystal composition cause a decrease in the voltage holding ratio (VHR) of the liquid crystal panel. Therefore, there is a need for liquid crystal compositions that can maintain a high voltage holding ratio (VHR) even when a high-speed response is achieved.

[0007] The problem to be solved by the present invention is to provide a liquid crystal composition, a liquid crystal display device, and a polymerizable compound which have good pretilt angle formation and low-temperature storage stability while maintaining a high voltage holding ratio (VHR). [Means for solving the problem]

[0008] As a result of intensive investigations, the present inventors have found that the above-mentioned problems can be solved by a polymerizable compound-containing liquid crystal composition containing one or more polymerizable compounds represented by general formula (i) having at least two hydroxyl groups as described below and one or more liquid crystal compounds, and have thus completed the present invention.

[0009] The present invention, which solves the above problems, is configured as follows.

[0010] The polymerizable compound according to the present invention is The following general formula (i)

[0011] [ka]

[0012] (In the formula, A i1 , A i2 and A i3 each independently represents a divalent aromatic group, a divalent alicyclic group, or a divalent heterocyclic group; A i1 , A i2 and A i3 One or more hydrogen atoms in each independently represent a substituent Sr i1 may be substituted with Substituent Sr i1 is a halogen atom, an alkyl group having 1 to 40 carbon atoms, or S i3 represents one of the following: One or more -CH2- groups in the alkyl group may each independently be substituted with -O- or -NH-; one or more -CH2-CH2- groups in the alkyl group may each independently be replaced by -CH=CH-, -C≡C-, -CO-O- or -O-CO-; One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, Oxygen atoms do not bond directly to each other, Substituent Sr i1 When there are multiple S, they may be the same or different. i1 , S i2 and S i3 are each independently represented by the following formula (S i -1)~(S i -5)

[0013] [ka]

[0014] (Formula(S i -1) Medium, P i1 represents a polymerizable group, Sp i1 represents a single bond or a spacer group, * is A i1 , A i2 or Ai3 Represents a bond to .

[0015] Formula (S i -2)~(S i -4) Medium, G i1 , G i2 and G i3 each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, or an arylene group having 1 to 20 carbon atoms; one or more -CH2- in the alkylene group and arylene group may each independently be substituted with -O-; one or more -CH2-CH2- in the alkylene group and the arylene group may each independently be substituted by -O-CO- or -CO-O-; One or more hydrogen atoms in the alkylene group and arylene group may be independently substituted with a hydroxyl group, a halogen atom, or an alkyl group having 1 to 6 carbon atoms, Oxygen atoms do not bond directly to each other, R i1 is a hydrogen atom, P i1 -Sp i1 -, or an alkyl group having 1 to 20 carbon atoms, P i1 represents a polymerizable group, Sp i1 represents a single bond or a spacer group, One or more -CH2- groups in the alkyl group may each independently be replaced with -O-; One or more -CH2-CH2- groups in the alkyl group may each independently be replaced by -O-CO- or -CO-O-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom or an alkyl group having 1 to 6 carbon atoms, Oxygen atoms do not bond directly to each other, * is A i1 , A i2 or A i3 Represents a bond to .

[0016] Formula (S i -5) Medium, G i4 represents an arylene group having 1 to 20 carbon atoms, one or more -CH2- in the arylene group may each independently be replaced by -O-; one or more -CH2-CH2- in the arylene group may each independently be replaced by -O-CO- or -CO-O-; One or more hydrogen atoms in the arylene group may be independently substituted with a hydroxyl group, a halogen atom, or an alkyl group having 1 to 6 carbon atoms, Oxygen atoms do not bond directly to each other, at least one hydrogen atom in the arylene group is replaced with a second hydroxyl group; * is A i1 , A i2 or A i3 represents a bond to .) represents a group selected from the group consisting of S i1 , S i2 and S i3 At least one of the formulas (S i -1), S i1 , S i2 and S i3 At least one of the formulas (S i -2)~(S i -5), L i1 and L i2 each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, one or more hydrogen atoms in the alkylene group may each independently be substituted with a halogen atom or an alkyl group having 1 to 6 carbon atoms; n i1 represents an integer between 0 and 1.) The polymerizable compound is characterized by being represented by the following formula:

[0017] The polymerizable compound-containing liquid crystal composition according to the present invention comprises one or more of the above-mentioned polymerizable compounds, One or more liquid crystal compounds It is characterized by including at least

[0018] The liquid crystal display device according to the present invention is characterized by using the above-mentioned liquid crystal composition. [Effects of the Invention]

[0019] According to the present invention, by using a polymerizable compound-containing liquid crystal composition containing one or more polymerizable compounds represented by general formula (i) having at least two hydroxyl groups and one or more liquid crystal compounds, it is possible to provide a liquid crystal display device having good voltage holding ratio, good pretilt angle formation, and good low-temperature storage stability. [Brief explanation of the drawings]

[0020] [Figure 1] 1 is an exploded perspective view showing an example of a liquid crystal display element according to the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0021] (Polymerizable compound represented by general formula (i)) The liquid crystal composition according to the present invention contains one or more polymerizable compounds having at least two hydroxyl groups and represented by the following general formula (i):

[0022] [ka]

[0023] In general formula (i), A i1 , A i2 and A i3 each independently represents a divalent aromatic group, a divalent cycloaliphatic group, or a divalent heterocyclic group.

[0024] Examples of the divalent aromatic group include a 1,4-phenylene group, a naphthalene-2,6-diyl group, an anthracene-2,6-diyl group, a phenanthrene-2,7-diyl group, an indan-2,5-diyl group, and a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group.

[0025] Examples of the divalent cycloaliphatic group include a 1,4-cyclohexylene group, a 1,4-cyclohexenylene group, and a 1,3-dioxane-2,5-diyl group.

[0026] Examples of the divalent heterocyclic compound group include a pyridine-2,5-diyl group and a pyrimidine-2,5-diyl group.

[0027] A i1 , A i2 and A i3 One or more hydrogen atoms in each independently represent a substituent Sr i1 may be substituted with.

[0028] Substituent Sr i1 is a halogen atom, an alkyl group having 1 to 40 carbon atoms, or S i3 It represents one of the following.

[0029] One or more -CH2- groups in the alkyl group may each independently be substituted with -O- or -NH-.

[0030] Furthermore, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted with -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0031] Furthermore, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom.

[0032] However, when the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0033] Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0034] The alkyl group having 1 to 40 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0035] The alkyl group having 1 to 40 carbon atoms preferably has 2 to 24, preferably 2 to 16, and preferably 2 to 8 carbon atoms.

[0036] For example, Sr i1 can represent an alkoxy group having 1 to 39 carbon atoms by substituting one -CH2- in the alkyl group with -O-.

[0037] The alkoxy group having 1 to 39 carbon atoms is a linear, branched or cyclic alkoxy group, and is preferably a linear alkoxy group.

[0038] The alkoxy group having 1 to 39 carbon atoms preferably has 2 to 24, preferably 2 to 16, and preferably 2 to 8 carbon atoms.

[0039] Also, Sr i1 can represent an alkoxyalkyl group having 1 to 39 carbon atoms by substituting one —CH2— group in the alkyl group with —O—.

[0040] The alkoxyalkyl group having 1 to 39 carbon atoms is a linear, branched or cyclic alkoxyalkyl group, and is preferably a linear alkoxyalkyl group.

[0041] The alkoxyalkyl group having 1 to 39 carbon atoms preferably has 2 to 24, preferably 2 to 16, and preferably 2 to 8 carbon atoms.

[0042] Also, Sr i1can represent a halogenated alkyl group having 1 to 40 carbon atoms, by which one or more hydrogen atoms in the alkyl group are each independently substituted with a halogen atom.

[0043] The halogenated alkyl group having 1 to 40 carbon atoms is a linear, branched or cyclic halogenated alkyl group, and is preferably a linear halogenated alkyl group.

[0044] The halogenated alkyl group having 1 to 40 carbon atoms preferably has 2 to 24 carbon atoms, preferably 2 to 16 carbon atoms, and preferably 2 to 8 carbon atoms.

[0045] Sr i1 Specific examples of the alkyl group having 1 to 40 carbon atoms (including substituted alkyl groups) include those of the formula (Sr i1 -1)~(Sr i1 -21).

[0046] [ka]

[0047] Formula (Sr i1 -1)~(Sr i1 -21) In the middle, the black dot is A i1 , A i2 or A i3 Represents a bond to .

[0048] Substituent Sr i1 When there are a plurality of, they may be the same or different.

[0049] A i1 Substituent Sr in i1 The substitution position of the following formula (A i1 -SP-1)~(A i1 -SP-3).

[0050] [ka]

[0051] Formula (A i1 -SP-1)~(A i1 -SP-3) White spots are S i1 The black dots represent bonds in L i1 Represents a bond to .

[0052] A i2 Substituent Sr in i1 The substitution position of the following formula (A i2 -SP-1)~(A i2 -SP-2).

[0053] [ka]

[0054] Formula (A i2 -SP-1)~(A i2 -SP-2) White spots are L i1 The black dots represent bonds to L i2 Represents a bond to .

[0055] A i3 Substituent Sr in i1 The substitution position of the following formula (A i3 -SP-1)~(A i3 -SP-2).

[0056] [ka]

[0057] Formula (A i3 -SP-1)~(A i3 -SP-2) White spots are L i2 or A i3 The black dot represents a bond to A. i3 or S i2 Represents a bond to .

[0058] More specifically, A i1is expressed by the following formula (A i1 -1)~(A i1 -5) is preferred.

[0059] [ka]

[0060] Formula (A i1 -1)~(A i1 -5) Medium, white dots are S i1 The black dots represent bonds in L i1 Represents a bond to .

[0061] More specifically, A i2 is expressed by the following formula (A i2 -1)~(A i2 -13) is preferably represented by either

[0062] [ka]

[0063] Formula (A i2 -1)~(A i2 -13) Medium, white dots L i1 The black dots represent bonds to L i2 Represents a bond to .

[0064] More specifically, A i3 is expressed by the following formula (A i3 -1)~(A i3 -3) is preferred.

[0065] [ka]

[0066] Formula (A i3 -S1)~(A i3 -3) Medium, white point is L i2 or A i3 The black dot represents a bond to A. i3 or S i2Represents a bond to .

[0067] In general formula (i), S i1 , S i2 and S i3 are each independently represented by the following general formula (S i -1)~(S i -5).

[0068] [ka]

[0069] Formula (S i -1) Medium, P i1 represents a polymerizable group.

[0070] Polymerizable groups are, for example, groups suitable for chain polymerization, such as radical, cationic or anionic polymerization, and / or step-growth polymerization, such as polyaddition or polycondensation.

[0071] The polymerizable group is preferably a group containing a carbon-carbon double bond (>C=C<), a carbon-carbon triple bond (-C≡C-) and / or an n-membered ring structure (n is an integer of 3 to 7) containing an oxygen atom as a constituent member.

[0072] The polymerizable group is represented by the formula (P i1 -1)~(P i1 -8) is preferably a group selected from the group consisting of:

[0073] [ka]

[0074] Formula (P i1 -1)~(P i1 -8) Medium, S i11 , S i21 , S i31 , S i32 , S i33 and S i41each 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.

[0075] Examples of the alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, and a propyl group.

[0076] Examples of the halogenated alkyl group having 1 to 5 carbon atoms include a trifluoromethyl group and a difluoroethyl group.

[0077] S i11 , S i21 , S i31 , S i32 , S i33 and S i41 It is preferable that each independently represents a hydrogen atom, a methyl group, an ethyl group, or a propyl group.

[0078] Formula (P i1 -1)~(P i1 -8) In the middle, the black dots are Sp i1 Represents a point of attachment to

[0079] In order to ensure appropriate reactivity, P i1 is the formula (P i1 -1), formula (P i1 -2), formula (P i1 -3), formula (P i1 -4), formula (P i1 -5) or formula (P i1 -7), and is preferably of the formula (P i1 -1), formula (P i1 -2), formula (P i1 -3) or formula (P i1 -7), and is preferably of the formula (P i1 -1), and an acrylic group (formula (P i1 -1), S i11 = hydrogen atom) or methacryl group (formula (P i1 -1), S i11 = methyl group), and a methacryl group is preferred.

[0080] Also, P i1 In the case where there are multiple i1 may be the same or different.

[0081] Also, P i1 However, the same formula (P i1 -1)~(P i1 -8), the same symbols in the formula may be the same or different.

[0082] Sp i1 represents a single bond or a spacer group.

[0083] The spacer group is a flexible group.

[0084] More specifically, the spacer group represents an alkylene group having 1 to 15 carbon atoms.

[0085] One or more -CH2- in the alkylene group may each independently be substituted with -O-.

[0086] In addition, one or more -CH2-CH2- in the alkylene group may be substituted with -O-CO- or -CO-O-.

[0087] However, when the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0088] The alkylene group having 1 to 15 carbon atoms is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0089] The alkylene group having 1 to 15 carbon atoms preferably has 1 to 12, preferably 1 to 9, and preferably 1 to 6 carbon atoms.

[0090] Sp i1 Specific examples of the alkylene group having 1 to 15 carbon atoms (including substituted ones) in the formula (Spi1 -1)~(Sp i1 -5).

[0091] [ka]

[0092] Formula (Sp i1 -1)~(Sp i1 -5) In the middle, the white point is P i1 represents a bond to A, and * represents A i1 , A i2 or A i3 Represents a bond to .

[0093] Also, Sp i1 If there are multiple Sp i1 may be the same or different.

[0094] Formula (S i -1) In, * is A i1 , A i2 or A i3 Represents a bond to .

[0095] Formula (S i A specific example of formula (S i -1-1)~(S i -1-12).

[0096] [ka]

[0097] Formula (S i -1-1)~(S i -1-12) * indicates A i1 , A i2 or A i3 Represents a bond to .

[0098] Formula (S i -2)~(S i -4) Medium, G i1 , G i2 and Gi3 each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, or an arylene group having 1 to 20 carbon atoms.

[0099] One or more -CH2- in the alkylene group and arylene group may each independently be substituted with -O-.

[0100] In addition, one or more -CH2-CH2- groups in the alkylene group and arylene group may each independently be substituted with -O-CO- or -CO-O-.

[0101] Furthermore, one or more hydrogen atoms in the alkylene group and arylene group may each independently be substituted with a hydroxyl group, a halogen atom, or an alkyl group having 1 to 6 carbon atoms.

[0102] However, when the alkylene group and arylene group are substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0103] The alkylene group having 1 to 20 carbon atoms is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0104] The alkylene group having 1 to 20 carbon atoms preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms.

[0105] The arylene group having 1 to 20 carbon atoms preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms.

[0106] G i1 , G i2 and G i3 Specific examples of the alkylene group having 1 to 20 carbon atoms or the arylene group having 1 to 20 carbon atoms (including substituted groups) in the formula (G i1 / 2 / 3 -1)~(G i1 / 2 / 3 -9).

[0107] [ka]

[0108] Formula (G i1 / 2 / 3 -1)~(G i1 / 2 / 3 -9) In, * is A i1 , A i2 , A i3 A black dot represents a bond to a hydroxyl group, carbon atom (C), silicon atom (Si) or nitrogen atom (N).

[0109] Also, G i1 , G i2 and G i3 In the case where there are multiple G i1 , G i2 and G i3 may be the same or different.

[0110] Formula (S i -2)~(S i -4) Medium, R i1 is a hydrogen atom, P i1 -Sp i1 -, or an alkyl group having 1 to 20 carbon atoms.

[0111] P i1 represents a polymerizable group, and its definition and explanation are given in the formula (S i -1) in P i1 is the same as

[0112] Sp i1 represents a single bond or a spacer group, and its definition and explanation are given in the formula (S i -1) in P i1 is the same as

[0113] However, "Formula (Sp i1 -1)~(Sp i1 -4) Medium, white point is P i1 represents a bond to A, and * represents A i1 , A i2 or A i3Regarding the notation "represents a bond to the formula (Sp i1 -1)~(Sp i1 -4) Medium, white point is P i1 represents a bond to a carbon atom (C) or a silicon atom (Si)." and shall be applied mutatis mutandis.

[0114] The alkyl group having 1 to 20 carbon atoms is a linear, branched or cyclic alkyl group, and is preferably a linear alkyl group.

[0115] The alkyl group having 1 to 20 carbon atoms preferably has 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms.

[0116] One or more -CH2- groups in the alkyl group may each independently be substituted with -O-.

[0117] In addition, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted with -O-CO- or -CO-O-.

[0118] Furthermore, one or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom or an alkyl group having 1 to 6 carbon atoms.

[0119] However, when the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0120] For example, R i1 can represent an alkoxyalkoxy group having 1 to 18 carbon atoms by substituting two -CH2- in the alkyl group with -O-.

[0121] The alkoxyalkoxy group having 1 to 18 carbon atoms is a linear, branched or cyclic alkoxyalkoxy group, and is preferably a linear alkoxyalkoxy group.

[0122] The alkoxyalkoxy group having 1 to 18 carbon atoms preferably has 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms.

[0123] R i1 Specific examples of the alkyl group having 1 to 20 carbon atoms (including substituted alkyl groups) in the formula (R i1 -1)~(R i1 -2) and the like.

[0124] [ka]

[0125] Formula (R i1 -1)~(R i1 In -2), the black dots represent bonds to carbon atoms (C) or silicon atoms (Si).

[0126] Formula (S i -2)~(S i -4) In, * is A i1 , A i2 or A i3 Represents a bond to .

[0127] Formula (S i A specific example of formula (S i -2-1)~(S i -2-21).

[0128] [ka]

[0129] [ka]

[0130] [ka]

[0131] Formula (S i-2-1)~(S i -2-21) * indicates A i1 , A i2 or A i3 Represents a bond to .

[0132] Formula (S i A specific example of formula (S i -3-1)~(S i -3-13).

[0133] [ka]

[0134] [ka]

[0135] Formula (S i -2-1)~(S i -2-13) * indicates A i1 , A i2 or A i3 Represents a bond to .

[0136] Formula (S i A specific example of formula (S i -4-1)~(S i -4-4).

[0137] [ka]

[0138] Formula (S i -4-1)~(S i -4-4) * indicates A i1 , A i2 or A i3 Represents a bond to .

[0139] Formula (S i -5) Medium, G i4 represents an arylene group having 1 to 20 carbon atoms.

[0140] One or more -CH2- in the arylene group may each independently be replaced by -O-.

[0141] In addition, one or more -CH2-CH2- in the arylene group may each independently be substituted with -O-CO- or -CO-O-.

[0142] Furthermore, one or more hydrogen atoms in the arylene group may each independently be substituted with a hydroxyl group, a halogen atom, or an alkyl group having 1 to 6 carbon atoms.

[0143] However, oxygen atoms are not directly bonded to each other.

[0144] In addition, at least one hydrogen atom in the arylene group is substituted with a second hydroxyl group.

[0145] That is, the formula (S i -5) has at least two hydroxyl groups.

[0146] The arylene group having 1 to 20 carbon atoms preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms.

[0147] G i4 Specific examples of the arylene group having 1 to 20 carbon atoms (including substituted ones) in the formula (G i4 -1)~(G i4 -6).

[0148] [ka]

[0149] Formula (G i4 -1)~(G i4 -6) In, * is A i1 , A i2 or A i3 The black dots represent bonds to the hydroxyl group.

[0150] Formula (S i -5) In, * is A i1 , A i2 or A i3 Represents a bond to .

[0151] Formula (S i A specific example of formula (S i -5-1)~(S i -5-6).

[0152] [ka]

[0153] Formula (S i -5-1)~(S i -5-6) * indicates A i1 , A i2 or A i3 Represents a bond to .

[0154] However, S i1 , S i2 and S i3 At least one of the formulas (S i From the viewpoint of pretilt angle stability (IS), S i1 is the formula (S i -1) is preferred.

[0155] Also, S i1 , S i2 and S i3 At least one of the formulas (S i -2)~(S i -5).

[0156] From the viewpoint of high voltage holding ratio (VHR), i2 is the formula (S i -2) is preferred.

[0157] S i3When there are a plurality of each of them, they may be the same or different.

[0158] In general formula (i), L i1 and L i2 each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms.

[0159] One or more hydrogen atoms in the alkylene group may each independently be substituted with a halogen atom or an alkyl group having 1 to 6 carbon atoms.

[0160] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0161] The alkylene group having 1 to 20 carbon atoms is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0162] The alkylene group having 1 to 20 carbon atoms preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms.

[0163] L i1 and L i2 Specific examples of the alkylene group having 1 to 20 carbon atoms (including substituted ones) in the formula (L i1 / 2 -1)~(L i1 / 2 -2) and the like.

[0164] [ka]

[0165] Formula (L i1 / 2 -1)~(L i1 / 2 -2) Medium, white point is A i1 or A i2 The black dot represents a bond to A. i2 , A i3 or S i2 Represents a bond to .

[0166] Li1 and L i2 At least one of L is preferably a single bond. i1 and L i2 It is more preferable that both are single bonds.

[0167] In general formula (i), n i1 represents an integer of 0 to 1, and is preferably 0.

[0168] The polymerizable compound represented by general formula (i) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (i-1) to (i-14).

[0169] [ka]

[0170] [ka]

[0171] In general formulas (i-1) to (i-14), S i1 , S i2 and Sr i1 are each independently S in the above general formula (i). i1 , S i2 and Sr i1 and each mean the same thing.

[0172] Specific examples of the compound represented by general formula (i-1) include compounds represented by the following structural formulas (i-1-1) to (i-1-36).

[0173] [ka]

[0174] [ka]

[0175] [ka]

[0176] [ka]

[0177] [ka]

[0178] Specific examples of the compound represented by general formula (i-2) include compounds represented by the following structural formulas (i-2-1) to (i-2-10).

[0179] [ka]

[0180] [ka]

[0181] Specific examples of the compound represented by general formula (i-3) include compounds represented by the following structural formulas (i-3-1) to (i-3-14).

[0182] [ka]

[0183] [ka]

[0184] Specific examples of the compound represented by general formula (i-4) include compounds represented by the following structural formulas (i-4-1) to (i-4-16).

[0185] [ka]

[0186] [ka]

[0187] Specific examples of the compound represented by general formula (i-5) include compounds represented by the following structural formulas (i-5-1) to (i-5-48).

[0188] [ka]

[0189] [ka]

[0190] [ka]

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] Specific examples of the compound represented by general formula (i-6) include compounds represented by the following structural formulas (i-6-1) to (i-6-14).

[0195] [ka]

[0196] [ka]

[0197] Specific examples of the compound represented by general formula (i-7) include compounds represented by the following structural formulas (i-7-1) to (i-7-16).

[0198] [ka]

[0199] [ka]

[0200] Specific examples of the compound represented by general formula (i-8) include compounds represented by the following structural formulas (i-8-1) to (i-8-10).

[0201] [ka]

[0202] [ka]

[0203] Specific examples of the compound represented by general formula (i-9) include compounds represented by the following structural formulas (i-9-1) to (i-9-8).

[0204] [ka]

[0205] Specific examples of the compound represented by general formula (i-10) include compounds represented by the following structural formulas (i-10-1) to (i-10-12).

[0206] [ka]

[0207] [ka]

[0208] Specific examples of the compound represented by general formula (i-11) include compounds represented by the following structural formulas (i-11-1) to (i-11-4).

[0209] [ka]

[0210] Specific examples of the compound represented by general formula (i-12) include compounds represented by the following structural formulas (i-12-1) to (i-12-8).

[0211] [ka]

[0212] Specific examples of the compound represented by general formula (i-13) include compounds represented by the following structural formulas (i-13-1) to (i-13-4).

[0213] [ka]

[0214] Specific examples of the compound represented by general formula (i-14) include compounds represented by the following structural formulas (i-14-1) to (i-14-4).

[0215] [ka]

[0216] General formula (i), General formula (i-1)~(i-13), Structural formula (i-1-1)~(i-1-36), Structural formula (i-2-1)~(i-2-10), Structural formula (i-3-1)~(i-3-14), Structural formula (i-4-1)~(i-4-1) 6), Structural formula (i-5-1) ~ (i-5-48), Structural formula (i-6-1) ~ (i-6-14), Structural formula (i-7-1) ~ (i-7-16), Structural formula (i-8-1) ~ (i-8-10), Structural formula (i-9-1) ~ (i-9-8) ), structural formulas (i-10-1) to (i-10-12), structural formulas (i-11-1) to (i-11-8), structural formulas (i-12-1) to (i-12-8), structural formulas (i-13-1) to (i-13-4), or structural formulas (i-14-1) to (i-14-4), the type used in the polymerizable compound-containing liquid crystal composition is one or more types, preferably 1 to 5 types, preferably 1 to 4 types, preferably 1 to 3 types, preferably 1 or 2 types, and preferably 1 type.

[0217] General formula (i), General formula (i-1)~(i-13), Structural formula (i-1-1)~(i-1-36), Structural formula (i-2-1)~(i-2-10), Structural formula (i-3-1)~(i-3-14), Structural formula (i-4-1)~(i-4-16) , Structural formula (i-5-1)~(i-5-48), Structural formula (i-6-1)~(i-6-14), Structural formula (i-7-1)~(i-7-16), Structural formula (i-8-1)~(i-8-10), Structural formula (i-9-1)~(i-9-8), Structural formula The lower limit of the total content of the polymerizable compounds represented by structural formulae (i-10-1) to (i-10-12), structural formulae (i-11-1) to (i-11-8), structural formulae (i-12-1) to (i-12-8), structural formulae (i-13-1) to (i-13-4), or structural formulae (i-14-1) to (i-14-4) in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably 0.1% by mass or more, more preferably 0.15% by mass or more, and even more preferably 0.2% by mass or more.

[0218] General formula (i), General formula (i-1)~(i-13), Structural formula (i-1-1)~(i-1-36), Structural formula (i-2-1)~(i-2-10), Structural formula (i-3-1)~(i-3-14), Structural formula (i-4-1)~(i-4-16) ), Structural formula (i-5-1)~(i-5-48), Structural formula (i-6-1)~(i-6-14), Structural formula (i-7-1)~(i-7-16), Structural formula (i-8-1)~(i-8-10), Structural formula (i-9-1)~(i-9-8), The upper limit of the total content of the polymerizable compounds represented by structural formulae (i-10-1) to (i-10-12), structural formulae (i-11-1) to (i-11-8), structural formulae (i-12-1) to (i-12-8), structural formulae (i-13-1) to (i-13-4), or structural formulae (i-14-1) to (i-14-4) in 100% by mass of the polymerizable-compound-containing liquid crystal composition is preferably 1.0% by mass or less, more preferably 0.7% by mass or less, and even more preferably 0.5% by mass or less.

[0219] General formula (i), General formula (i-1) to (i-13), Structural formula (i-1-1) to (i-1-36), Structural formula (i-2-1) to (i-2-10), Structural formula (i-3-1) to (i-3-14), Structural formula (i-4-1) to (i-4-16), Structural formula (i- 5-1)~(i-5-48), Structural formula (i-6-1)~(i-6-14), Structural formula (i-7-1)~(i-7-16), Structural formula (i-8-1)~(i-8-10), Structural formula (i-9-1)~(i-9-8), Structural formula (i-10-1)~(i-10) From the viewpoint of achieving both a high voltage holding ratio (VHR) and low-temperature storage stability, the total content of the polymerizable compounds represented by structural formulas (i-12), structural formulas (i-11-1) to (i-11-8), structural formulas (i-12-1) to (i-12-8), structural formulas (i-13-1) to (i-13-4), or structural formulas (i-14-1) to (i-14-4) in 100% by mass of the polymerizable-compound-containing liquid crystal composition is preferably 0.1 to 1.0% by mass, more preferably 0.15 to 0.7% by mass, and even more preferably 0.2 to 0.5% by mass.

[0220] General formula (i), General formula (i-1) to (i-13), Structural formula (i-1-1) to (i-1-36), Structural formula (i-2-1) to (i-2-10), Structural formula (i-3-1) to (i-3-14), Structure Formula (i-4-1)~(i-4-16), Structural formula (i-5-1)~(i-5-48), Structural formula (i-6-1)~(i-6-14), Structural formula (i-7-1)~(i-7-16), Structural formula (i-8- The polymerizable compounds represented by structural formulae (i-1) to (i-8-10), structural formulae (i-9-1) to (i-9-8), structural formulae (i-10-1) to (i-10-12), structural formulae (i-11-1) to (i-11-8), structural formulae (i-12-1) to (i-12-8), structural formulae (i-13-1) to (i-13-4), or structural formulae (i-14-1) to (i-14-4) can be synthesized using known synthesis methods. (Polymerizable liquid crystal compound having a structure different from that of general formula (i)) The polymerizable compound-containing liquid crystal composition according to the present invention may contain one or more polymerizable compounds having a structure different from that of general formula (i).

[0221] For example, examples of polymerizable compounds having a structure different from that of general formula (i) include polymerizable compounds represented by the following general formula (ii).

[0222] [ka]

[0223] In general formula (i), R ii1 , R ii2 , R ii3 , R ii4 , R ii5 , R ii6 , R ii7 and R ii8 each independently represents an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom, or a hydrogen atom.

[0224] The alkyl group having 1 to 18 carbon atoms may be linear, branched, or cyclic, but is preferably linear from the viewpoint of obtaining good orientation.

[0225] The number of carbon atoms in the alkyl group having 1 to 18 carbon atoms is preferably 1 to 3 when importance is placed on solubility in a liquid crystal composition containing a polymerizable compound, and is preferably 10 to 18 when importance is placed on vertical alignment of the liquid crystal composition containing a polymerizable compound.

[0226] The alkoxy group having 1 to 18 carbon atoms may be linear, branched, or cyclic, with the linear type being preferred from the viewpoint of obtaining good orientation.

[0227] The number of carbon atoms in the alkoxy group having 1 to 18 carbon atoms is preferably 1 to 3 when importance is placed on solubility in a liquid crystal composition containing a polymerizable compound, and is preferably 10 to 18 when importance is placed on vertical alignment of the liquid crystal composition containing a polymerizable compound.

[0228] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0229] From the viewpoint of ensuring compatibility with liquid crystal compounds, R ii1 , R 1i2 , R ii5 , R ii6 and R ii8 At least one of the groups is preferably a halogen atom, more preferably a fluorine atom.

[0230] In general formula (ii), P ii1 and P ii2 each independently represents a polymerizable group.

[0231] Polymerizable groups are, for example, groups suitable for chain polymerization, such as radical, cationic or anionic polymerization, and / or step-growth polymerization, such as polyaddition or polycondensation.

[0232] The polymerizable group is preferably a group containing a carbon-carbon double bond (>C=C<), a carbon-carbon triple bond (-C≡C-) and / or an n-membered ring structure (n is an integer of 3 to 7) containing an oxygen atom as a constituent member.

[0233] The polymerizable group is represented by the following general formula (P ii1 / 2 -1)~(P ii1 / 2 -8) is preferably a group selected from the group consisting of:

[0234] [ka]

[0235] General formula (P ii1 / 2 -1)~(P ii1 / 2 -8) Medium, S ii11 , S ii21 , S ii31 , S ii32 , S ii33 and S ii41 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.

[0236] Examples of the alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, and a propyl group.

[0237] Examples of the halogenated alkyl group having 1 to 5 carbon atoms include a trifluoromethyl group and a difluoroethyl group.

[0238] S ii11 , S ii21 , S ii31 , S ii32 , S ii33 and S ii41 are each preferably independently a hydrogen atom, a methyl group, an ethyl group, or a propyl group.

[0239] General formula (P ii1 / 2 -1)~(P ii1 / 2 -8) * indicates Sp ii1 or Sp ii2 Represents a point of attachment to

[0240] In order to ensure appropriate reactivity, P ii1 and P ii2 are each independently expressed by the formula (P ii1 / 2 -1), formula (Pii1 / 2 -2), formula (P ii1 / 2 -3), formula (P ii1 / 2 -4), formula (P ii1 / 2 -5) or formula (P ii1 / 2 -7), and is preferably of the formula (P ii1 / 2 -1), formula (P ii1 / 2 -2), formula (P ii1 / 2 -3) or formula (P ii1 / 2 -7), and is preferably of the formula (P ii1 / 2 -1), and an acrylic group (formula (P ii1 / 2 -1), S ii11 = hydrogen atom) or methacryl group (formula (P ii1 / 2 -1), S ii11 = methyl group), and a methacryl group is preferred.

[0241] Also, P ii1 and P ii2 may be the same or different, but are preferably the same.

[0242] In addition, P ii1 and P ii2 However, the same formula (P ii1 / 2 -1)~(P ii1 / 2 -8), the same symbols in the formula may be the same or different.

[0243] In addition, from the viewpoint of compatibility with the liquid crystal compound, in the polymerizable compound represented by general formula (ii), R ii1 , R ii2 , R ii3 , R ii4 , R ii5 , R ii6 , R ii7 and R ii8 However, it does not represent a hydrogen atom at the same time, and R ii1 , R ii2 , R ii3 , R ii4 , R ii5 , R ii6 , R ii7 and R ii8At least one of these is preferably a halogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 18 carbon atoms.

[0244] In general formula (ii), Sp ii1 and Sp ii2 each independently represents a single bond or a spacer group.

[0245] The spacer group is a flexible group.

[0246] More specifically, the spacer group is an alkylene group having 1 to 15 carbon atoms.

[0247] One or more -CH2- in the alkylene group may each independently be substituted with -O-.

[0248] Furthermore, one or more -CH2-CH2- in the alkylene group may each independently be substituted with -O-CO- or -CO-O-.

[0249] However, when the alkylene group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0250] In addition, two or more Sp ii1 and Sp ii2 may be the same or different.

[0251] The alkylene group having 1 to 15 carbon atoms is a linear, branched or cyclic alkylene group, and is preferably a linear alkylene group.

[0252] The alkylene group having 1 to 15 carbon atoms preferably has 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, and preferably 2 to 3 carbon atoms.

[0253] More specifically, Sp ii1 and Sp ii2preferably each independently represents a single bond, -CH2-, -CH2-CH2-, -CH2-CH2-CH2-, -O-, -CH2-O-, -CH2-CH2-O-, or -CH2-CO-O-; Sp ii1 and Sp ii2 are preferably both single bonds.

[0254] In general formula (ii), n ii1 represents an integer of 1 to 2.

[0255] n ii1 When represents 2, there are multiple R ii5 , R ii6 , R ii7 and R ii8 may be the same or different from each other.

[0256] Suitable examples of the polymerizable compound represented by general formula (ii) include compounds represented by the following general formulae (ii-1) and (ii-2).

[0257] [ka]

[0258] In general formulas (ii-1) to (ii-2), Sp ii1 , Sp ii2 , R ii6 and R ii7 is Sp in the above general formula (ii). ii1 , Sp ii2 , R ii6 and R ii7 It has the same meaning as:

[0259] Specific examples of the polymerizable compound represented by general formula (ii-1) include polymerizable compounds represented by the following structural formulas (ii-1-1) to (ii-1-4).

[0260] [ka]

[0261] Specific examples of the polymerizable compound represented by general formula (ii-2) include polymerizable compounds represented by the following structural formulae (ii-2-1) to (ii-1-2).

[0262] [ka]

[0263] The number of types of polymerizable liquid crystal compounds represented by general formula (ii), general formulas (ii-1) to (ii-2), structural formulas (ii-1-1) to (ii-1-4), or structural formulas (ii-2-1) to (ii-2-2) contained in the liquid crystal composition of the present invention is preferably 1 to 5 types, more preferably 1 to 4 types, more preferably 1 to 3 types, more preferably 1 or 2 types, and most preferably 1 type.

[0264] The lower limit of the total content of the polymerizable compounds represented by general formula (ii), general formulas (ii-1) to (ii-2), structural formulas (ii-1-1) to (ii-1-4), or structural formulas (ii-2-1) to (ii-2-2) in 100% by mass of the polymerizable-compound-containing liquid crystal composition is preferably 0.1% by mass or more, more preferably 0.15% by mass or more, and even more preferably 0.2% by mass or more.

[0265] The upper limit of the total content of the polymerizable compounds represented by general formula (ii), general formulas (ii-1) to (ii-2), structural formulas (ii-1-1) to (ii-1-4), or structural formulas (ii-2-1) to (ii-2-2) in 100% by mass of the polymerizable-compound-containing liquid crystal composition is preferably 1.0% by mass or less, more preferably 0.7% by mass or less, and even more preferably 0.5% by mass or less.

[0266] The total content of the polymerizable compounds represented by general formula (ii), general formulas (ii-1) to (ii-2), structural formulas (ii-1-1) to (ii-1-4), or structural formulas (ii-2-1) to (ii-2-2) in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably 0.1 to 1.0% by mass, more preferably 0.15 to 0.7% by mass, and even more preferably 0.2 to 0.5% by mass. (Polymerizable compound-containing liquid crystal composition) The polymerizable compound-containing liquid crystal composition according to the present invention can be produced, for example, by mixing the polymerizable compound represented by the above-mentioned general formula (i), a liquid crystal composition used for the polymerizable compound-containing liquid crystal composition, and, if necessary, a polymerizable compound having a structure different from that of general formula (i), and additives.

[0267] The liquid crystal composition used in the polymerizable compound-containing liquid crystal composition contains one or more liquid crystal compounds.

[0268] Examples of liquid crystal compounds include those with a negative dielectric anisotropy at 20°C (Δε<-2), neutral (-2≦Δε≦2), and positive (2<Δε).

[0269] The dielectric anisotropy (Δε) of the liquid crystal compound is a value extrapolated from the measured value of the dielectric anisotropy of a composition obtained by adding the liquid crystal compound to a composition that is nearly dielectrically neutral at 20°C.

[0270] The liquid crystal compound having a negative dielectric anisotropy (Δε<-2) at 20°C is preferably a compound selected from the group consisting of liquid crystal compounds represented by any of the following general formulas (N-01) to (N-05).

[0271] [ka]

[0272] In general formulas (N-01) to (N-05), R 21 and R 22each independently represents 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, and one or more -CH2- in the group may each independently be substituted by -C≡C-, -CO-, -CO-O-, or -O-CO-.

[0273] However, when the group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0274] R 21 is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms, and even more preferably an alkyl group having 2 to 4 carbon atoms.

[0275] However, Z 1 If represents anything other than a single bond, R 21 is preferably an alkyl group having 1 to 3 carbon atoms.

[0276] R 22 is preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and more preferably an alkoxy group having 1 to 4 carbon atoms.

[0277] The alkenyl group having 2 to 8 carbon atoms includes the groups represented by the formulae (R1) to (R7), with the group represented by the formula (R1) or (R2) being preferred.

[0278] [ka]

[0279] In the formulae (R1) to (R7), the black dots represent bonds to the ring structure.

[0280] In general formulas (N-01) to (N-05), Z 1each independently represents a single bond, -CH2-CH2-, -O-CH2-, -CH2-O-, -CO-O-, -O-CO-, -O-CF2-, -CF2-O-, -CH=CH-, -CF=CF- or -C≡C-.

[0281] In the general formulae (N-01) to (N-05), each m independently represents 1 or 2.

[0282] When m is 1, Z 1 is preferably a single bond or —CH2—O—.

[0283] When m is 2, Z 1 is preferably a single bond, —CH2—CH2— or —CH2—O—.

[0284] The hydrogen atoms present on the rings of the liquid crystal compounds represented by the general formulae (N-01) to (N-05) may each be independently substituted with a fluorine atom or a chlorine atom.

[0285] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains, as the compound represented by general formula (N-01), one or more compounds selected from the group of compounds represented by general formulas (N-01-1) to (N-01-4).

[0286] [ka]

[0287] In general formulas (N-01-1) to (N-01-4), R 23 and R 24 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

[0288] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-01-1) and a liquid crystal compound represented by general formula (N-01-4).

[0289] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-01-3) and a liquid crystal compound represented by general formula (N-01-4).

[0290] Examples of the liquid crystal compound represented by the general formula (N-01-1) include liquid crystal compounds represented by the following structural formulas (N-01-1.1) to (N-01-1.2).

[0291] [ka]

[0292] Examples of the liquid crystal compound represented by general formula (N-01-2) include liquid crystal compounds represented by the following structural formulae (N-01-2.1) to (N-01-2.5).

[0293] [ka]

[0294] Examples of the liquid crystal compound represented by general formula (N-01-3) include liquid crystal compounds represented by the following structural formulas (N-01-3.1) to (N-01-3.3).

[0295] [ka]

[0296] Examples of the liquid crystal compound represented by general formula (N-01-4) include liquid crystal compounds represented by the following structural formulae (N-01-4.1) to (N-01-4.4).

[0297] [ka]

[0298] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains, as the compound represented by general formula (N-02), one or more compounds selected from the group of compounds represented by general formulas (N-02-1) to (N-02-3).

[0299] [ka]

[0300] In general formulas (N-02-1) to (N-02-3), R 24 each independently represents an alkyl group having 1 to 5 carbon atoms.

[0301] In general formulas (N-02-1) to (N-02-3), R 23 each independently represents an alkoxy group having 1 to 4 carbon atoms.

[0302] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-02-1).

[0303] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-02-1) and a liquid crystal compound represented by general formula (N-02-3).

[0304] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-02-1) and a liquid crystal compound represented by general formula (N-01-4).

[0305] Examples of the liquid crystal compound represented by general formula (N-02-1) include liquid crystal compounds represented by the following structural formula (N-02-1.1).

[0306] [ka]

[0307] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains one or more liquid crystal compounds represented by general formula (N-03-1) as the liquid crystal compound represented by general formula (N-03).

[0308] [ka]

[0309] In general formula (N-03-1), R 24 represents an alkyl group having 1 to 5 carbon atoms.

[0310] In general formula (N-03-1), R 23 represents an alkoxy group having 1 to 4 carbon atoms.

[0311] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-03-1).

[0312] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-03-1) and a liquid crystal compound represented by general formula (N-01-4).

[0313] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-03-1) and a liquid crystal compound represented by general formula (N-02-1).

[0314] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (N-03-1), a liquid crystal compound represented by general formula (N-01-4), and a liquid crystal compound represented by general formula (N-02-1).

[0315] Examples of the liquid crystal compound represented by general formula (N-03-1) include liquid crystal compounds represented by the following structural formulas (N-03-1.1) to (N-03-1.5).

[0316] [ka]

[0317] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains one or more liquid crystal compounds represented by general formula (N-04-1) as the liquid crystal compound represented by general formula (N-04).

[0318] [ka]

[0319] In general formula (N-04-1), R 24 represents an alkyl group having 1 to 5 carbon atoms.

[0320] In general formula (N-04-1), R 23 represents an alkoxy group having 1 to 4 carbon atoms.

[0321] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a compound represented by general formula (N-04-1) and a compound represented by general formula (N-01-4).

[0322] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a compound represented by general formula (N-04-1), a compound represented by general formula (N-01-4), and a compound represented by general formula (N-02-1).

[0323] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a compound represented by general formula (N-04-1), a compound represented by general formula (N-01-4), and a compound represented by general formula (N-03-1).

[0324] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a compound represented by general formula (N-04-1), a compound represented by general formula (N-02-1), and a compound represented by general formula (N-03-1).

[0325] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a compound represented by general formula (N-04-1), a compound represented by general formula (N-01-4), a compound represented by general formula (N-02-1), and a compound represented by general formula (N-03-1).

[0326] Examples of the liquid crystal compound represented by general formula (N-04-1) include liquid crystal compounds represented by the following structural formulae (N-04-1.1) to (N-04-1.2).

[0327] [ka]

[0328] The polymerizable compound-containing liquid crystal composition according to the present invention may contain, as the compound represented by general formula (N-05), a liquid crystal compound selected from the group of compounds represented by structural formulas (N-05-1) to (N-05-2).

[0329] [ka]

[0330] The polymerizable compound-containing liquid crystal composition of the present invention contains the general formulae (N-01) to (N-05), general formulae (N-01-1) to (N-01-4), general formulae (N-02-1) to (N-02-3), general formula (N-03-1), general formula (N-04-1), structural formulae (N-01-1.1) to (N-01-1.2), structural formulae (N-01-2.1) to (N-01-2.5), structural formulae (N-01-3.1) to (N-01-3.3), structural formula ( The number of types of liquid crystal compounds represented by structural formulas (N-01-4.1) to (N-01-4.4), structural formulas (N-02-1.1), structural formulas (N-03-1.1) to (N-03-1.5), structural formulas (N-04-1.1) to (N-04-1.2), or structural formulas (N-05-1) to (N-05-2) is preferably 1 to 15, more preferably 1 to 13, still more preferably 2 to 13, and still more preferably 2 to 11.

[0331] The preferred lower limit of the total content of liquid crystal compounds represented by general formula (N-01), general formulas (N-01-1) to (N-01-4), structural formulae (N-01-1.1) to (N-01-1.2), structural formulae (N-01-2.1) to (N-01-2.5), structural formulae (N-01-3.1) to (N-01-3.3), or structural formulae (N-01-4.1) to (N-01-4.4) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0% by mass, 1% by mass, 5% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, or 80% by mass.

[0332] The preferred upper limit of the total content of liquid crystal compounds represented by general formula (N-01), general formulas (N-01-1) to (N-01-4), structural formulae (N-01-1.1) to (N-01-1.2), structural formulae (N-01-2.1) to (N-01-2.5), structural formulae (N-01-3.1) to (N-01-3.3), or structural formulae (N-01-4.1) to (N-01-4.4) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, 20% by mass, 15% by mass, or 10% by mass.

[0333] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-02), general formulae (N-02-1) to (N-02-3), or structural formula (N-02-1.1) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0% by mass, 1% by mass, 5% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, or 80% by mass.

[0334] The preferred upper limit of the total content of the liquid crystal compounds represented by general formula (N-02), general formulae (N-02-1) to (N-02-3), or structural formula (N-02-1.1) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, 20% by mass, 15% by mass, or 10% by mass.

[0335] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-03), general formula (N-03-1), or structural formulae (N-03-1.1) to (N-03-1.5) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0% by mass, 1% by mass, 5% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, or 80% by mass.

[0336] The preferred upper limit of the total content of the liquid crystal compounds represented by general formula (N-03), general formula (N-03-1), or structural formulae (N-03-1.1) to (N-03-1.5) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, 20% by mass, 15% by mass, or 10% by mass.

[0337] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-04), general formula (N-04-1), or structural formulae (N-04-1.1) to (N-04-1.2) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0% by mass, 1% by mass, 5% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, or 80% by mass.

[0338] The preferred upper limit of the total content of the liquid crystal compounds represented by general formula (N-04), general formula (N-04-1), or structural formulae (N-04-1.1) to (N-04-1.2) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, 25% by mass, 20% by mass, 15% by mass, or 10% by mass.

[0339] The preferred lower limit of the total content of the liquid crystal compounds represented by general formula (N-05) or structural formulae (N-05-1) to (N-05-2) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0% by mass, 2% by mass, 5% by mass, 8% by mass, 10% by mass, 13% by mass, 15% by mass, 17% by mass, or 20% by mass.

[0340] The preferred upper limit of the total content of the liquid crystal compounds represented by general formula (N-05) or structural formulae (N-05-1) to (N-05-2) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 30% by mass, 28% by mass, 25% by mass, 23% by mass, 20% by mass, 18% by mass, 15% by mass, or 13% by mass.

[0341] The liquid crystal compound having a neutral dielectric anisotropy at 20°C (-2≦Δε≦2) is preferably a compound selected from the group consisting of liquid crystal compounds represented by any of the following general formulas (NU-01) to (NU-08).

[0342] [ka]

[0343] In general formulas (NU-01) to (NU-08), R NU11 , R NU12 , R NU21 , R NU22 , R NU31 , R NU32 , R NU41 , R NU42 , R NU51, R NU52 , R NU61 , R NU62 , R NU71 , R NU72 , R NU81 and R NU82 each independently represents 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, and one or more -CH2-CH2- in the group may each independently be substituted by -C≡C-, -CO-, -CO-O-, or -O-CO-.

[0344] However, when the group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0345] R NU11 , R NU12 , R NU21 , R NU22 , R NU31 , R NU32 , R NU41 , R NU42 , R NU51 , R NU52 , R NU61 , R NU62 , R NU71 , R NU72 , R NU81 and R NU82 As the alkyl group, an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms is preferred, and an alkyl group having 1 to 5 carbon atoms is more preferred.

[0346] In addition, when a high-speed response is desired, R NU11 is an alkenyl group having 2 to 3 carbon atoms, and R NU12 is preferably an alkyl group having 1 to 6 carbon atoms, and by including this compound in the polymerizable compound-containing liquid crystal composition according to the present invention, high-speed response can be reliably achieved. This is because the compound has low viscosity or low rotational viscosity, which greatly contributes to improving both the reliability and response properties.

[0347] More specifically, R NU11 , R NU21 , R NU31 , R NU41 , R NU51 , R NU61 , R NU71 , R NU81 is particularly preferably an alkyl group having 1 to 5 carbon atoms, and R NU12 , R NU22 , R NU32 , R NU42 , R NU52 , R NU62 , R NU72 and R NU82 is particularly preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.

[0348] Examples of the alkenyl group having 2 to 3 carbon atoms include the groups represented by formulae (R1) and (R2), with the group represented by formula (R1) or (R2) being preferred.

[0349] [ka]

[0350] In formulas (R1) to (R2), the black dots represent bonds to the ring structure.

[0351] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-01) and a liquid crystal compound represented by general formula (NU-02).

[0352] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-01) and a liquid crystal compound represented by general formula (NU-03).

[0353] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-03) and a liquid crystal compound represented by general formula (NU-04).

[0354] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-03) and a liquid crystal compound represented by general formula (NU-05).

[0355] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-01) and a liquid crystal compound represented by general formula (NU-06).

[0356] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-01) and a liquid crystal compound represented by general formula (NU-07).

[0357] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-01) and a liquid crystal compound represented by general formula (NU-08).

[0358] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-01), a liquid crystal compound represented by general formula (NU-02), and a liquid crystal compound represented by general formula (NU-04).

[0359] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-01), a liquid crystal compound represented by general formula (NU-03), and a liquid crystal compound represented by general formula (NU-05).

[0360] The polymerizable compound-containing liquid crystal composition according to the present invention preferably contains a liquid crystal compound represented by general formula (NU-01), a liquid crystal compound represented by general formula (NU-02), a liquid crystal compound represented by general formula (NU-03), and a liquid crystal compound represented by general formula (NU-05).

[0361] The polymerizable compound-containing liquid crystal composition of the present invention more preferably contains a liquid crystal compound represented by general formula (NU-01).

[0362] In the general formula (NU-01), RNU51 is particularly preferably an alkyl group having 1 to 5 carbon atoms, and R NU52 is particularly preferably an alkyl group having 1 to 5 carbon atoms.

[0363] The polymerizable compound-containing liquid crystal composition of the present invention more preferably contains a liquid crystal compound represented by general formula (NU-01) and a liquid crystal compound represented by general formula (NU-05).

[0364] In the general formula (NU-01), R NU51 is particularly preferably an alkyl group having 1 to 5 carbon atoms, and R NU52 is particularly preferably an alkyl group having 1 to 5 carbon atoms.

[0365] The polymerizable compound-containing liquid crystal composition of the present invention more preferably contains a liquid crystal compound represented by general formula (NU-01), a liquid crystal compound represented by general formula (NU-02), and a liquid crystal compound represented by general formula (NU-05).

[0366] In the general formula (NU-01), R NU51 is particularly preferably an alkyl group having 1 to 5 carbon atoms, and R NU52 is particularly preferably an alkyl group having 1 to 5 carbon atoms.

[0367] The liquid crystal composition of the present invention more preferably contains a liquid crystal compound represented by general formula (NU-01), a liquid crystal compound represented by general formula (NU-02), a liquid crystal compound represented by general formula (NU-03), and a liquid crystal compound represented by general formula (NU-05).

[0368] Examples of the liquid crystal compound represented by the general formula (NU-01) include liquid crystal compounds represented by the following structural formulas (NU-01-1) to (NU-01-6).

[0369] [ka]

[0370] Examples of the liquid crystal compound represented by the general formula (NU-02) include liquid crystal compounds represented by the following structural formulas (NU-02-1) to (NU-02-2).

[0371] [ka]

[0372] Examples of the liquid crystal compound represented by the general formula (NU-03) include liquid crystal compounds represented by the following structural formulas (NU-03-1) to (NU-03-3).

[0373] [ka]

[0374] Examples of the liquid crystal compound represented by the general formula (NU-04) include liquid crystal compounds represented by the following structural formulas (NU-04-1) to (NU-04-2).

[0375] [ka]

[0376] Examples of the liquid crystal compound represented by the general formula (NU-05) include liquid crystal compounds represented by the following structural formulas (NU-05-1) to (NU-05-3).

[0377] [ka]

[0378] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-01) or structural formulae (NU-01-1) to (NU-01-6) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 10 to 55% by mass, 15 to 50% by mass, or 20 to 45% by mass.

[0379] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-02) or structural formulae (NU-02-1) to (NU-02-2) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0 to 20% by mass, 0.5 to 15% by mass, or 1 to 10% by mass.

[0380] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-03) or structural formulae (NU-03-1) to (NU-03-3) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0 to 30% by mass, 1 to 25% by mass, or 3 to 20% by mass.

[0381] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-04) or structural formulae (NU-04-1) to (NU-04-2) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0 to 25% by mass, 0.5 to 15% by mass, or 1 to 10% by mass.

[0382] The preferred range of the total content of the liquid crystal compounds represented by general formula (NU-05) or structural formulae (NU-05-1) to (NU-05-3) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 0 to 25% by mass, 1 to 20% by mass, or 3 to 15% by mass.

[0383] The total content of the liquid crystal compounds represented by general formula (NU-06) in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably in the range of 0 to 30% by mass, more preferably 0 to 20% by mass, and even more preferably 0 to 10% by mass.

[0384] The total content of the liquid crystal compounds represented by general formula (NU-07) in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably in the range of 0 to 30% by mass, more preferably 0 to 20% by mass, and even more preferably 0 to 20% by mass.

[0385] The total content of the liquid crystal compounds represented by general formula (NU-08) in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably in the range of 0 to 30% by mass, more preferably 0 to 20% by mass, and even more preferably 0 to 10% by mass.

[0386] The liquid crystal compound having a positive dielectric anisotropy (2<Δε) at 20°C is preferably a compound selected from the group consisting of liquid crystal compounds represented by any of the following general formulas (P-01) to (P-02).

[0387] [ka]

[0388] In the general formulas (P-01) to (P-02), R P11 each independently represents 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.

[0389] R P11 As the alkyl group, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 2 to 5 carbon atoms is preferred, an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferred, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is preferred, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferred.

[0390] R if reliability is important P11 is preferably an alkyl group, and when a reduction in viscosity is important, is preferably an alkenyl group.

[0391] Also, R P11 When the ring structure to which R is bonded is a phenyl group (aromatic), it is preferably any one of 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 R P11When the ring structure to which is bonded is a saturated ring structure such as cyclohexane, pyran, and dioxane, it is preferably any one of a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, it is preferable that the total number of carbon atoms and oxygen atoms, if present, is 5 or less, and it is preferably linear.

[0392] Examples of the alkenyl group having 2 to 8 carbon atoms include groups represented by formulae (R1) to (R7), with formula (R1) or (R2) being preferred.

[0393] [ka]

[0394] In general formulas (P-01) to (P-02), ring A P11 each independently represents a 1,4-cyclohexylene group in which at least one -CH2- in the ring may be substituted with -O- or -S-, or a 1,4-phenylene group in which at least one -CH= in the ring may be substituted with -N=, and ring A P11 At least one of the hydrogen atoms therein may be substituted with a halogen.

[0395] Examples of halogen atoms include chlorine atoms, bromine atoms, and fluorine atoms.

[0396] In addition, ring A P11 When there are multiple, they may be the same or different.

[0397] Ring A P11 are each independently preferably a 1,4-phenylene group in which at least one of -CH= in the ring may be substituted with -N= when it is required to increase Δn, and are each independently preferably a 1,4-cyclohexylene group in which at least one of -CH2- in the ring may be substituted with -O- or -S- in order to improve the response speed, and are each independently preferably a 1,4-phenylene ... the P11 -1)~(AP11 It is more preferable that the structure is one of the structures represented by the formulas (1)-6).

[0398] [ka]

[0399] L P11 each independently represents a single bond, -C2H4-, -CH=CH-, -C≡C-, -COO-, -OCO-, -C2O-, -OCH2-, -CF2O-, or -OCF2-.

[0400] In addition, L P11 When there are multiple, they may be the same or different.

[0401] In general formula (P-01)~(P-02), m P11 represents an integer of 1 to 4.

[0402] In general formulas (P-01)~(P-02), Y P11 and Y P12 each independently represents a hydrogen atom or a fluorine atom.

[0403] In general formulas (P-01) to (P-02), X P11 represents any one of -F, -Cl, -CN, -NCS, -CF3, -OCF3, an alkyl group having 1 to 6 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom, and an alkoxy group having 1 to 6 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom.

[0404] Examples of halogen atoms include chlorine atoms, bromine atoms, and fluorine atoms.

[0405] As the liquid crystal compound represented by general formula (P-01), compounds represented by general formulas (P-01-1) to (P-01-28) are preferred.

[0406] [ka]

[0407] [ka]

[0408] [ka]

[0409] [ka]

[0410] [ka]

[0411] In general formulas (P-01-1) to (P-01-28), R P12 represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0412] The compound represented by general formula (P-02) is preferably a compound represented by general formulas (P-02-1) to (P-02-6).

[0413] [ka]

[0414] In general formulas (P-02-1) to (P-02-6), R P12 represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0415] The liquid crystal compounds represented by the general formulae (P-01) and (P-02) may be selected from only one of the groups, or may be selected from each group and used in combination.

[0416] When the reliability of the polymerizable compound-containing liquid crystal composition according to the present invention is important, it is preferable to use a liquid crystal compound selected from the group represented by general formulas (P-01-1) to (P-01-11), (P-01-16) to (P-01-20) and general formulas (P-02-1) to (P-02-4), and more preferably selected from the group represented by general formulas (P-01-1), (P-01-2), (P-01-4), (P-01-17) and (P-01-20).

[0417] When low viscosity of the polymerizable compound-containing liquid crystal composition according to the present invention is important, it is preferable to use a liquid crystal compound selected from the group represented by general formulas (P-01-12) to (P-01-15), (P-01-21) to (P-01-28), and (P-01-5) to (P-01-6), and more preferably selected from the group represented by formulas (P-01-12), (P-01-13), (P-01-22), (P-01-23), and (P-01-26).

[0418] When prioritizing the low viscosity of the polymerizable compound-containing liquid crystal composition according to the present invention and also prioritizing the improvement of transmittance in the FFS mode, it is preferable to use a liquid crystal compound selected from the group represented by (P-01-14), (P-01-15), (P-01-25), (P-01-27) and (P-01-28).

[0419] In order to shorten the process time for UV irradiation in the manufacturing process of the liquid crystal display element according to the present invention, it is preferable to use a liquid crystal compound selected from the group represented by general formulas (P-01-4) to (P-01-7), (P-01-20) and (P-01-4), and among these, a liquid crystal compound selected from (P-01-4) or (P-01-20) is particularly preferable. By using liquid crystal compounds from these groups, problems such as deterioration of the polymerizable compound-containing liquid crystal composition upon UV irradiation, a decrease in the voltage holding ratio of the liquid crystal display element, and image sticking can be prevented or reduced in severity.

[0420] The liquid crystal compounds represented by general formulas (P-01) to (P-02), general formulas (P-01-1) to (P-01-28), and / or general formulas (P-02-1) to (P-02-6) are appropriately selected depending on the properties required for the liquid crystal display element, and multiple types can be used in combination as needed, but it is preferable to use 1 to 12 types, it is more preferable to use 2 to 10 types, and it is particularly preferable to use 3 to 8 types.

[0421] The preferred lower limit of the total content of the liquid crystal compounds represented by general formulae (P-01) to (P-02), general formulae (P-01-1) to (P-01-28), or general formulae (P-02-1) to (P-02-6) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 1% by mass, 10% by mass, 20% by mass, 30% by mass, 40% by mass, 50% by mass, 55% by mass, 60% by mass, 65% by mass, 70% by mass, 75% by mass, or 80% by mass.

[0422] The preferred upper limit of the total content of the liquid crystal compounds represented by general formulae (P-01) to (P-02), general formulae (P-01-1) to (P-01-28), or general formulae (P-02-1) to (P-02-6) in 100% by mass of the polymerizable compound-containing liquid crystal composition is 95% by mass, 85% by mass, 75% by mass, 65% by mass, 55% by mass, 45% by mass, 35% by mass, or 25% by mass.

[0423] In the polymerizable compound-containing liquid crystal composition according to the present invention, the total content of the liquid crystal compounds represented by general formulas (P-01) to (P-02), general formulas (P-01-1) to (P-01-28), or general formulas (P-02-1) to (P-02-6) may be adjusted as appropriate depending on the required performance, such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and dielectric anisotropy.

[0424] In order to maintain a low viscosity of the polymerizable compound-containing liquid crystal composition according to the present invention and increase the response speed, it is preferable to set the above lower limit value low and the upper limit value low.

[0425] T of the polymerizable compound-containing liquid crystal composition according to the present invention NI When it is desired to maintain a high temperature and improve the temperature stability, it is preferable to set the above lower limit value lower and the upper limit value lower.

[0426] When the dielectric anisotropy is increased in order to maintain a low driving voltage of the polymerizable compound-containing liquid crystal composition according to the present invention, it is preferable to increase the above lower limit and the upper limit.

[0427] The polymerizable compound-containing liquid crystal composition according to the present invention may further contain one or more compounds selected from the group consisting of compounds represented by any one of the following general formulas (Np-07-1) to (Np-07-12), from the viewpoint of shortening the process time for UV irradiation in the process of producing a liquid crystal display element.

[0428] [ka]

[0429] [ka]

[0430] In general formulas (Np-07-1) to (Np-07-12), R i111 and R i112 each independently represents an alkyl group having 1 to 8 carbon atoms.

[0431] One or more -CH2- groups in the alkyl group may each independently be substituted with -O- or -CO-.

[0432] Furthermore, one or more -CH2-CH2- groups in the alkyl group may each independently be substituted with -CH=CH-, -C≡C-, -CO-O- or -O-CO-.

[0433] However, when the alkyl group is substituted with a specific group, the oxygen atoms are not directly bonded to each other.

[0434] The polymerizable compound-containing liquid crystal composition according to the present invention may contain, in addition to the above-mentioned liquid crystal compounds, ordinary nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, and the like.

[0435] The polymerizable compound-containing liquid crystal composition according to the present invention may contain an additive.

[0436] Examples of the additives include antioxidants, ultraviolet absorbers, light stabilizers, and infrared absorbers.

[0437] The antioxidant is preferably one represented by any one of the general formulae (H-1) to (H-4).

[0438] [ka]

[0439] The lower limit of the total content of the antioxidant in 100% by mass of the polymerizable compound-containing liquid crystal composition is preferably 10 ppm by mass, preferably 20 ppm by mass, and preferably 50 ppm by mass, and the upper limit is preferably 10,000 ppm by mass, preferably 1,000 ppm by mass, preferably 500 ppm by mass, and preferably 100 ppm by mass.

[0440] In general formula (H-1) to general formula (H-3), R H1 each independently represents an alkyl group having 3 to 7 carbon atoms.

[0441] More specifically, R in general formula (H-1) H1 represents an alkyl group having 7 carbon atoms. H1 represents an alkyl group having 3 carbon atoms. H1 represents an alkyl group having 3 carbon atoms.

[0442] In general formula (H-4), M H1represents an alkylene group having 4 to 10 carbon atoms (one or two or more non-adjacent -CH2- groups in the group may be replaced with -CO-O- or -O-CO- so that the oxygen atoms are not directly adjacent), a single bond, a 1,4-phenylene group (any hydrogen atom in the 1,4-phenylene group may be replaced with a fluorine atom), or a trans-1,4-cyclohexylene group.

[0443] The alkylene group having 4 to 10 carbon atoms preferably has 4 to 8 carbon atoms.

[0444] A polymerization initiator may be added to the polymerizable compound-containing liquid crystal composition of the present invention in order to rapidly polymerize the polymerizable compound. As the polymerization initiator, a photopolymerization initiator is preferably selected.

[0445] Examples of photopolymerization initiators include acetophenone-based initiators such as diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzil dimethyl ketal, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, 1-hydroxycyclohexyl-phenyl ketone, 2-methyl-2-morpholino(4-thiomethylphenyl)propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone, 4'-phenoxyacetophenone, and 4'-ethoxyacetophenone; benzoin-based initiators such as benzoin, benzoin isopropyl ether, benzoin isobutyl ether, benzoin methyl ether, and benzoin ethyl ether; acylphosphine oxide-based initiators such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide; and benzil , methylphenylglyoxyester-based; benzophenone-based compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4,4'-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, acrylated benzophenone, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 3,3'-dimethyl-4-methoxybenzophenone, 2,5-dimethylbenzophenone, and 3,4-dimethylbenzophenone; thioxanthone-based compounds such as 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, and 2,4-dichlorothioxanthone; aminobenzophenone-based compounds such as Michler's ketone and 4,4'-diethylaminobenzophenone; 10-butyl-2-chloroacridone, 2-ethylanthraquinone, 9,10-phenanthrenequinone, and camphorquinone.

[0446] The upper limit of the total content of the photopolymerization initiator in the polymerizable compound-containing liquid crystal composition in 100 mass% of the polymerizable compound-containing liquid crystal composition is preferably 100 mass ppm, preferably 56 mass ppm, preferably 48 mass ppm, and preferably 36 mass ppm.

[0447] The dielectric anisotropy at 20°C of the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition may be negative (Δε<-2), neutral (-2≦Δε≦2), or positive (2<Δε), but is preferably negative (Δε<-2).

[0448] When the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition has a negative dielectric anisotropy (Δε<-2) at 20°C, the nematic phase-isotropic liquid phase transition temperature (T ni ) is preferably 60 to 120°C, more preferably 65 to 120°C, and even more preferably 65 to 115°C.

[0449] When the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition has a negative dielectric anisotropy (Δε<-2) at 20°C, the refractive index anisotropy (Δn) of the liquid crystal composition at 20°C is preferably 0.08 to 0.14, more preferably 0.09 to 0.13, and even more preferably 0.09 to 0.12.

[0450] When the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition has a negative dielectric anisotropy (Δε<-2) at 20°C, the dielectric anisotropy (Δε) of the liquid crystal composition at 20°C is preferably -2.1 to -4.5, preferably -2.5 to -4.3, preferably -2.7 to -4.0, and preferably -2.6 to -3.9.

[0451] When the liquid crystal composition used in the polymerizable compound-containing liquid crystal composition has a negative dielectric anisotropy at 20°C (Δε<-2), the rotational viscosity (γ1) of the liquid crystal composition at 20°C is preferably 50 to 160 mPa·s, preferably 55 to 160 mPa·s, preferably 60 to 160 mPa·s, preferably 65 to 155 mPa·s, preferably 70 to 150 mPa·s, preferably 75 to 145 mPa·s, or preferably 80 to 140 mPa·s. (Liquid crystal display element) Next, a liquid crystal display element having two substrates and a liquid crystal layer between the two substrates containing the above-mentioned polymerizable compound-containing liquid crystal composition, in which a polymer obtained by polymerizing the polymerizable compound represented by the general formula (i) is present in the polymerizable compound-containing liquid crystal composition, will be described.

[0452] More specifically, the liquid crystal display element has two substrates and a liquid crystal layer sandwiched between the two substrates and containing the above-mentioned polymerizable compound-containing liquid crystal composition that has been polymerized, and in the polymerizable compound-containing liquid crystal composition that has been polymerized, a polymer formed by polymerizing the polymerizable compound represented by the general formula (i) is present.

[0453] In addition, when the polymerizable compound-containing composition contains a polymerizable liquid crystal compound having a structure different from that of general formula (i), a polymer obtained by polymerizing the polymerizable liquid crystal compound having a structure different from that of general formula (i) may further be present.

[0454] The polymerization treatment may be performed by ultraviolet irradiation or the like.

[0455] The two substrates are divided into a first substrate and a second substrate.

[0456] The first substrate may comprise an alignment layer and / or a pixel electrode layer having transparent pixel electrodes driven by corresponding active elements on the second substrate.

[0457] The transparent electrode layer made of a transparent common electrode may be configured as an electrode layer having a plurality of gate bus lines and data bus lines arranged in a matrix, thin film transistors provided at intersections of the gate bus lines and the data bus lines, and pixel electrodes driven by the thin film transistors for each pixel.

[0458] Furthermore, the second substrate may also be provided with a transparent electrode layer made of a transparent common electrode, a color filter layer and / or an alignment film layer, if necessary.

[0459] The liquid crystal display element according to the present invention is preferably driven by an active matrix system or a passive matrix system.

[0460] The liquid crystal display element according to the present invention is preferably a liquid crystal display element in which the dielectric constant is reversibly switched by reversibly changing the alignment direction of the liquid crystal molecules of the liquid crystal composition.

[0461] Furthermore, the liquid crystal display element of the present invention may be a PSA type, PSVA type, VA type, IPS type, FFS type, PS-IPS type, PS-FFS type, NPS type or ECB type liquid crystal display element, and is preferably a PSA type, PSVA type, IPS type or FFS type liquid crystal display element.

[0462] 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.

[0463] A more specific explanation will be given below with reference to the drawings.

[0464] FIG. 1 is a schematic diagram showing an example of the liquid crystal display element of the present invention.

[0465] The structure of the liquid crystal display element of the present invention is not limited to this example.

[0466] In addition, in FIG. 1, for the sake of convenience, the components are shown separated from one another.

[0467] The liquid crystal display element 1 shown in FIG. 1 includes a first substrate 2 and a second substrate 3 arranged opposite to each other, and a liquid crystal layer 4 provided between the first substrate 2 and the second substrate 3.

[0468] As shown in FIG. 1, the first substrate 2 has a pixel electrode layer 5 formed on the surface thereof facing the liquid crystal layer 4.

[0469] On the second substrate 3, a transparent electrode layer 6 is formed on the liquid crystal layer 4 side.

[0470] The first substrate 2 and the second substrate 3 may be sandwiched between a pair of polarizing plates 7 and 8 .

[0471] A color filter layer 9 may further be provided on the liquid crystal layer 4 side of the second substrate 3.

[0472] The liquid crystal layer 4 contains the polymerizable compound-containing liquid crystal composition according to the present invention.

[0473] In the case of a liquid crystal display element manufactured using a liquid crystal composition containing a polymerizable compound, polymers of the polymerizable compound produced by ultraviolet irradiation during the manufacturing process are unevenly distributed at the interfaces on the first substrate 2 and second substrate sides in the liquid crystal layer 4.

[0474] That is, in the case of FIG. 1, a polymer of the polymerizable compound is formed at the interfaces between the liquid crystal layer 4 and the pixel electrode layer 5 and between the liquid crystal layer 4 and the transparent electrode layer 6.

[0475] Although not shown, the liquid crystal display element of the present invention comprises a first substrate and a second substrate facing each other, and a liquid crystal layer disposed between the first substrate and the second substrate and containing the polymerizable compound-containing liquid crystal composition of the present invention, and can have a first alignment film on the surface of the first substrate facing the liquid crystal layer, and a second alignment film on the surface of the second substrate facing the liquid crystal layer.

[0476] That is, the liquid crystal display element of the present invention can be configured by stacking a first polarizing plate, a first substrate, a first alignment film, a pixel electrode layer, a liquid crystal layer, a transparent electrode layer, a color filter layer, a second alignment film, a second substrate, and a second polarizing plate in this order.

[0477] The alignment film has the function of aligning the liquid crystal molecules.

[0478] The alignment film may be a polyimide alignment film or other film that is generally used in liquid crystal display devices.

[0479] The liquid crystal display device of the present invention can be produced by a known method. [Example]

[0480] The present invention will be described in more detail below based on examples, but the present invention is not limited to these examples.

[0481] Hereinafter, in the compositions of the Examples and Comparative Examples, the compounds are represented by the following abbreviations: where "n" represents a natural number.

[0482] <Ring structure>

[0483] [ka]

[0484] <Side chain> -n -C n H 2n+1 A straight-chain alkyl group with n carbon atoms n-C n H 2n+1 - a linear alkyl group with n carbon atoms -On -OC n H 2n+1 A straight-chain alkoxy group with n carbon atoms -V -CH=CH2 -V1 -CH=CH-CH3 1V- H3C-CH=CH- 1V2- H3C-CH=CH-CH2-CH2- <Connecting group> -n- -C n H 2n - -nO- -C n H 2n -O- <Physical Properties of Liquid Crystal Composition Used in Polymerizable Compound-Containing Liquid Crystal Composition> The liquid crystal composition used in the polymerizable compound-containing liquid crystal composition was measured for the following physical properties.

[0485] T ni : Nematic-isotropic liquid phase transition temperature (℃) Δn: Refractive index anisotropy at 20°C Δε: Dielectric anisotropy at 20°C γ1: Rotational viscosity at 20°C (mPa·s) <Polymerizable compound represented by general formula (i) (polymerizable compound a)> As the polymerizable compound represented by general formula (i), the following compound was used.

[0486] [ka]

[0487] <Polymerizable liquid crystal compound (polymerizable compound b) having a structure different from that of general formula (i)> As the polymerizable liquid crystal compound having a structure different from that of general formula (i), the following compounds were used.

[0488] [ka]

[0489] <Preparation of Liquid Crystal Composition (Base Composition) Used in Polymerizable Compound-Containing Liquid Crystal Composition> Liquid crystal compositions LC-1 to LC-8 used in the polymerizable compound-containing liquid crystal composition were prepared by mixing the liquid crystal compounds in the respective ratios shown in Table 1, and their physical properties were measured. The results are shown in Table 1.

[0490] [Table 1]

[0491] (Examples 1 to 30 and Comparative Examples 1 to 11) <Preparation of Liquid Crystal Composition Containing Polymerizable Compound> Polymerizable compound a and polymerizable compound b were added in the amounts (parts by mass) shown in Tables 2 to 4 to 100 parts by mass of each of the prepared LC-1 to LC-8, to prepare polymerizable compound-containing liquid crystal compositions of Examples 1 to 30 and Comparative Examples 1 to 11. <Fabrication of Liquid Crystal Display Element> A liquid crystal composition containing a polymerizable compound was injected by vacuum injection into a liquid crystal cell with a cell gap of 3.5 μm, which included an ITO substrate coated with a polyimide alignment film that induces vertical alignment and then rubbed. Then, the liquid crystal cell into which the polymerizable compound-containing liquid crystal composition had been injected was irradiated with ultraviolet light for 90 minutes using a fluorescent UV lamp, thereby producing a liquid crystal display element. The fluorescent UV lamp had an illuminance of 3.0 mW / cm2 measured under conditions of a central wavelength of 313 nm. 2 The concentration was adjusted to be <Evaluation test> The following evaluation tests were carried out on each of the polymerizable compound-containing liquid crystal compositions of Examples and Comparative Examples. The results are shown in Tables 2 to 4. (Method for evaluating voltage holding ratio) The voltage holding ratio (VHR) of the fabricated liquid crystal display device was measured under conditions of 1 V, 0.6 Hz and 60°C.

[0492] The evaluation criteria are as follows: A: 95% or more B: Less than 95% 90% or more C: Less than 90% 80% or more D: Less than 80% (Method for evaluating pretilt formation) First, the pretilt angle of the fabricated liquid crystal display element was measured and defined as the pretilt angle (initial). Next, the liquid crystal display element was irradiated with ultraviolet light from a fluorescent UV lamp for 200 seconds while applying a voltage of 10 V at a frequency of 100 Hz, and then the pretilt angle of the liquid crystal display element was measured and defined as the pretilt angle (post-UV).

[0493] The value obtained by subtracting the pretilt angle (after UV) from the measured pretilt angle (initial) was taken as the pretilt angle change [°].

[0494] The pretilt angle was measured using an OPTIPRO manufactured by Shintech.

[0495] In addition, the fluorescent UV lamp has an illuminance of 3.0 mW / cm2 measured under the condition of a central wavelength of 313 nm. 2 The concentration was adjusted to be

[0496] The evaluation criteria are as follows: A: 2.0° or more B: Less than 2.0° and 1.5° or more C: Less than 1.5° and 1.0° or more D: Less than 1.0° (Method for evaluating low-temperature storage stability) The polymerizable compound-containing liquid crystal composition was filtered using a membrane filter (manufactured by Agilent Technologies, PTFE 13 mm-0.2 μm), and 0.5 g was weighed into a test tube. The tube was then degassed under vacuum (2.5 to 2.0 hPa) for 15 minutes, purged with nitrogen, and sealed with a rubber stopper to obtain a sample for evaluating low-temperature storage stability. The sample was stored in a freezer at -20°C and observed daily for the presence or absence of precipitation.

[0497] The evaluation criteria are as follows: ◯: No precipitation was observed even after 10 days of storage. △: Precipitation was confirmed within 6 to 9 days. ×: Precipitation occurred within 5 days, which was rated as ×.

[0498] [Table 2]

[0499] [Table 3]

[0500] [Table 4]

[0501] The liquid crystal compositions of Examples 1 to 18, which contain both polymerizable compound a and polymerizable compound b shown in Table 2, improved or maintained their voltage holding ratios and pretilt angle changes, and also had good low-temperature storage stability, demonstrating superior performance compared to the liquid crystal compositions of Comparative Examples 1 to 10, which contain polymerizable compound b but not polymerizable compound a shown in Table 4, and which have the same base composition. Comparing the liquid crystal compositions of Example 1 and Comparative Example 1, which have the same base composition, Example 1 exhibited improved voltage holding ratios and pretilt angle changes compared to Comparative Example 1. This is thought to be because the liquid crystal composition of Example 1 contains polymerizable compound a represented by general formula (i) having at least two hydroxyl groups, thereby reducing the influence of impurities present in the liquid crystal cell, as described above.

[0502] Furthermore, from a comparison between Example 12 and Example 17 and a comparison between Example 16 and Example 18, it was confirmed that even when the polymerizable compound b combined with the polymerizable compound a is a compound represented by formula (b-2), the same effect as when the polymerizable compound B is a compound represented by formula (b-1) can be obtained.

[0503] Furthermore, by comparing the liquid crystal compositions of Examples 1 to 18, in which the total content of polymerizable compound a and polymerizable compound b was 0.7% by mass, the liquid crystal compositions of Comparative Examples 1 to 10, which did not contain polymerizable compound a but contained 0.3% by mass of polymerizable compound b, and Comparative Example 11, which did not contain polymerizable compound a but contained 0.7% by mass of polymerizable compound b, it was confirmed that the improvements in the three parameters of voltage holding ratio, pretilt angle change, and low-temperature storage stability were not due to an increase in the total content of polymerizable compound a and polymerizable compound b, but were the effect of adding polymerizable compound a.

[0504] Furthermore, as can be seen from the results of the liquid crystal compositions of Examples 19 to 30 shown in Table 3, it was confirmed that by containing the polymerizable compound a, it was possible to achieve a high voltage holding ratio, a large pretilt angle change, and excellent low-temperature storage stability, even without containing the polymerizable compound b.

[0505] The synthesis of the compounds (a-1) to (a-5) will be described below.

[0506] (Synthesis Example of Polymerizable Compound Represented by General Formula (i) (Example)) (Synthesis Example of a-1 (Example)) (step-1)

[0507] [ka]

[0508] Under a nitrogen atmosphere, 4-bromophenol (15.0 g, 86.7 mmol), 5-(bromomethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methyl acetate (31.7 g, 112.7 mmol), potassium carbonate (36.0 g, 260.1 mmol), and N,N-dimethylformamide (75 mL) were mixed in a reaction vessel equipped with a stirrer, heater, and thermometer, and the mixture was reacted at 90 °C for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, and ethyl acetate and water were added and the mixture was separated. The resulting organic layer was washed with saturated brine and the solvent was evaporated. The residue was then purified by silica gel column chromatography (silica gel 33 g, mobile phase: toluene) to obtain the compound represented by (S-1) (30.7 g, yield 95%). (step-2)

[0509] [ka]

[0510] Under a nitrogen atmosphere, a reaction vessel equipped with a stirrer, heater, and thermometer was charged with compound (S-1) (21.0 g, 56.3 mmol), (4-hydroxyphenyl)boronic acid (5.4 g, 39.4 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.4 g, 0.6 mmol), and THF (105 mL), mixed, and heated to 60 °C. While heating, a 2 mol / L aqueous potassium carbonate solution (70 mL, 140 mmol) was added dropwise, and the mixture was stirred at 60 °C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and ethyl acetate and water were added, followed by separation. The resulting organic layer was washed with saturated saline, and the solvent was distilled off. Subsequently, a reaction vessel equipped with a stirrer and thermometer was charged with ethanol (40 mL) and an aqueous sodium hydroxide solution (40 mL), mixed, and stirred at room temperature for 4 hours. After the reaction was completed, a mixed solvent of hexane and ethyl acetate (hexane / ethyl acetate = 3 / 1) was added, the organic layer was washed with water and saturated saline, and the solvent was distilled off. The residue was then purified by silica gel column chromatography (silica gel 19 g, mobile phase: hexane / ethyl acetate = 4 / 1 to 2 / 1) to obtain the compound represented by (S-2) (16.9 g, yield 87%). (step-3)

[0511] [ka]

[0512] Compound (S-2) (16.9 g, 49.1 mmol), methacrylic acid (10.6 g, 122.7 mmol), DMAP (13 mg, 0.11 mmol), and dichloromethane (14 mL) were mixed in a reaction vessel equipped with a stirrer, condenser, and thermometer under atmospheric pressure. DIC (1.4 g, 11.3 mmol) was added under ice cooling and stirred overnight at room temperature. The precipitate was then filtered off, and the resulting liquid was washed with 10% hydrochloric acid, water, and saturated brine, and dried over anhydrous sodium sulfate. After filtering off the anhydrous sodium sulfate, 10 g of silica gel was added to the resulting liquid. This was purified by silica gel column chromatography (11 g of silica gel, mobile phase: dichloromethane). MEHQ was added, and the solvent was evaporated under reduced pressure in the dark. Methanol (54 mL) was added to the residue to reprecipitate, yielding compound (a-1) (15.1 g, 70% yield). [M]:440 (Synthesis Example of a-2 (Example)) (step-1)

[0513] [ka]

[0514] Under a nitrogen atmosphere, 4-bromo-3-ethylphenol (13.0 g, 65.0 mmol), 5-(bromomethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methyl acetate (23.8 g, 84.5 mmol), potassium carbonate (27.0 g, 195 mmol), and N,N-dimethylformamide (65 mL) were mixed in a reaction vessel equipped with a stirrer, heater, and thermometer, and the mixture was reacted at 90 °C for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, and ethyl acetate and water were added and the mixture was separated. The resulting organic layer was washed with saturated brine and the solvent was evaporated. The residue was then purified by silica gel column chromatography (silica gel 26 g, mobile phase: toluene) to obtain compound (S-3) (22.2 g, 85% yield). (step-2)

[0515] [ka]

[0516] Under a nitrogen atmosphere, a reaction vessel equipped with a stirrer, heater, and thermometer was charged with compound (S-3) (17.0 g, 42.4 mmol), (4-hydroxyphenyl)boronic acid (6.1 g, 44.5 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.3 g, 0.4 mmol), and THF (85 mL), mixed, and heated to 60 °C. While heating, a 2 mol / L aqueous potassium carbonate solution (53 mL, 106 mmol) was added dropwise, and the mixture was stirred at 60 °C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and ethyl acetate and water were added, followed by separation. The resulting organic layer was washed with saturated brine, and the solvent was distilled off. Subsequently, the residue, ethanol (40 mL), and aqueous sodium hydroxide solution (40 mL) were charged to a reaction vessel equipped with a stirrer and thermometer, mixed, and stirred at room temperature for 4 hours. After the reaction was completed, a mixed solvent of hexane / ethyl acetate (3 / 1) was added, the organic layer was washed with water and saturated saline, and the solvent was distilled off. The residue was then purified by silica gel column chromatography (silica gel 14 g, mobile phase: hexane / ethyl acetate = 4 / 1 to 2 / 1) to obtain the compound represented by (S-4) (12.6 g, yield 79%). (step-3)

[0517] [ka]

[0518] Compound (S-4) (6.7 g, 18.0 mmol), methacrylic acid (3.9 g, 50.0 mmol), DMAP (0.5 g, 4.1 mmol), and dichloromethane (27 mL) were mixed in a reaction vessel equipped with a stirrer, condenser, and thermometer under atmospheric pressure. DIC (5.2 g, 41.4 mmol) was added under ice cooling and stirred overnight at room temperature. The precipitate was then filtered off, and the resulting liquid was washed with 10% hydrochloric acid, water, and saturated brine, and dried over anhydrous sodium sulfate. After filtering off the anhydrous sodium sulfate, 2.4 g of silica gel was added to the resulting liquid. This was purified by silica gel column chromatography (5 g of silica gel, mobile phase: dichloromethane). MEHQ was added, and the solvent was evaporated under reduced pressure in the dark. Methanol (26 mL) was added to the residue to reprecipitate, yielding compound (a-2) (5.3 g, yield 63%). [M]:468 (Synthesis Example of a-3 (Example)) (step-1)

[0519] [ka]

[0520] Under a nitrogen atmosphere, 4-bromophenol (15.0 g, 86.7 mmol), (4-benzyloxyphenyl)boronic acid (29.1 g, 127.4 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.9 g, 1.2 mmol), and THF (75 mL) were mixed in a reaction vessel equipped with a stirrer, heater, and thermometer and heated to 60 °C. A 2 mol / L aqueous potassium carbonate solution (151 mL, 302 mmol) was added dropwise under heating, and the mixture was stirred at 60 °C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and ethyl acetate and water were added and separated. The resulting organic layer was washed with saturated brine and the solvent was evaporated. The residue was then purified by silica gel column chromatography (silica gel 37 g, mobile phase: hexane / ethyl acetate = 4 / 1 to 2 / 1) to obtain compound (S-5) (27.2 g, 81% yield). (step-2)

[0521] [ka]

[0522] Under a nitrogen atmosphere, compound (S-5) (15.4 g, 55.7 mmol), pyridine (10.9 g, 139 mmol), and dichloromethane (61.6 mL) were mixed in a reaction vessel equipped with a stirrer, a condenser, and a thermometer, and trifluoromethanesulfonic anhydride (18.9 g, 66.9 mmol) was added dropwise under ice cooling. After the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours, followed by the addition of water and dichloromethane for phase separation. Dichloromethane was added to the aqueous layer, which was then separated and combined with the organic layer containing dichloromethane. The combined organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel 24 g, mobile phase: hexane / ethyl acetate = 4 / 1 to 2 / 1) to obtain compound (S-6) (17.5 g, 42.9 mmol). (step-3)

[0523] [ka]

[0524] Under a nitrogen atmosphere, palladium(II) acetate (0.3 g, 1.4 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (1.3 g, 2.7 mmol), magnesium (1.1 g, 43.9 mmol), zinc chloride (6.0 g, 43.9 mmol), and THF (16 mL) were mixed in a reaction vessel equipped with a stirrer, heater, and thermometer and heated to 60 °C. While heating, a mixed solution of the compound represented by (S-6) (11.2 g, 27.4 mmol), 5-((benzyloxy)methyl)-5-(2 bromomethyl)-2,2-dimethyl-1,3-dioxane (12.2 g, 35.7 mmol), and THF (40 mL) was added dropwise, and the mixture was stirred at 60 °C for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and filtered through Celite. Then, ethyl acetate and water were added and the mixture was separated. The resulting organic layer was washed with saturated saline and the solvent was distilled off. The residue was then purified by silica gel chromatography (silica gel 16 g, mobile phase: dichloromethane) to obtain the compound represented by (S-7) (9.6 g, 18.4 mmol). (step-4)

[0525] [ka]

[0526] The compound represented by (S-7) (6.5 g, 12.4 mmol), palladium carbon (5 wt%, 0.7 g), and THF (39.0 mL) were mixed in a pressure-resistant reaction vessel and stirred at 40°C for 10 hours under a hydrogen pressure of 0.5 MPa. After the reaction was completed, the mixture was cooled to room temperature, and ethyl acetate and water were added for separation. The resulting organic layer was washed with saturated saline, and the solvent was distilled off. The residue was then suspended and washed in a mixed solvent of toluene and hexane (toluene / hexane = 3 / 1 to 1 / 1) to obtain the compound represented by (S-8) (3.1 g, yield 73%). (step-5)

[0527] [ka]

[0528] Compound (S-8) (3.1 g, 9.0 mmol), methacrylic acid (2.0 g, 22.7 mmol), DMAP (0.25 g, 2.1 mmol), and dichloromethane (19 mL) were mixed in a reaction vessel equipped with a stirrer, condenser, and thermometer under atmospheric pressure. DIC (2.6 g, 20.8 mmol) was added under ice cooling and the mixture was stirred overnight at room temperature. The precipitate was filtered off, and the resulting liquid was washed with 10% hydrochloric acid, water, and saturated brine, and then dried over anhydrous sodium sulfate. After filtering off the anhydrous sodium sulfate, 1.8 g of silica gel was added to the resulting liquid. This was purified by silica gel column chromatography (3 g of silica gel, mobile phase: dichloromethane). MEHQ was added, and the solvent was evaporated under reduced pressure in the dark. Methanol (11 mL) was added to the residue to reprecipitate, yielding the target compound (a-3) (3.7 g, 94% yield). [M]:438 (Synthesis Example of a-4 (Example)) (step-1)

[0529] [ka]

[0530] Under a nitrogen atmosphere, 4-bromo-2-fluorophenol (11.0 g, 57.6 mmol), 5-((2-benzoyloxy)ethoxy)-5-(bromomethyl)-2,2-dimethyl-1,3-dioxane (28.0 g, 74.9 mmol), potassium carbonate (23.9 g, 172.8 mmol), and N,N-dimethylformamide (55 mL) were mixed in a reaction vessel equipped with a stirrer, heater, and thermometer, and the mixture was reacted at 90°C for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, and ethyl acetate and water were added and the mixture was separated. The resulting organic layer was washed with saturated brine, and the solvent was distilled off. The residue was then purified by silica gel column chromatography (silica gel 27 g, mobile phase: toluene) to obtain the compound represented by (S-9) (24.5 g, yield 88%). (step-2)

[0531] [ka]

[0532] Under a nitrogen atmosphere, a reaction vessel equipped with a stirrer, heater, and thermometer was charged with compound (S-9) (10.0 g, 20.7 mmol), (4-hydroxyphenyl)boronic acid (3.0 g, 21.7 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.15 g, 0.21 mmol), and THF (63 mL). The mixture was then heated to 60 °C. A 2 mol / L aqueous potassium carbonate solution (26 mL, 52 mmol) was added dropwise under heating, and the mixture was stirred at 60 °C for 3 hours. After the reaction was completed, the mixture was cooled, and ethyl acetate and water were added. The resulting organic layer was washed with saturated brine, and the solvent was evaporated. The residue was then purified by silica gel column chromatography (silica gel 10 g, mobile phase: hexane / ethyl acetate = 4 / 1 to 2 / 1) to obtain compound (S-10) (8.5 g, 83% yield). (step-3)

[0533] [ka]

[0534] The compound represented by (S-10) (8.5 g, 17.1 mmol), palladium carbon (5 wt%, 0.9 g), and THF (51.4 mL) were mixed in a pressure-resistant reaction vessel and reacted at 40°C for 10 hours under a hydrogen pressure of 0.5 MPa. After the reaction was completed, the mixture was cooled to room temperature, and ethyl acetate and water were added for separation. The resulting organic layer was washed with saturated saline, and the solvent was distilled off. The residue was then suspended and washed in a mixed solvent of toluene and hexane (toluene / hexane = 3 / 1 to 1 / 1) to obtain the compound represented by (S-11) (6.7 g, yield 96%). (step-4)

[0535] [ka]

[0536] Compound (S-11) (2.8 g, 6.7 mmol), methacrylic acid (1.5 g, 11.0 mmol), DMAP (0.19 g, 1.6 mmol), and dichloromethane (19.6 mL) were mixed in a reaction vessel equipped with a stirrer, condenser, and thermometer under atmospheric pressure. DIC (2.0 g, 15.8 mmol) was added under ice cooling and the mixture was stirred overnight at room temperature. The precipitate was filtered off, and the resulting liquid was washed with 10% hydrochloric acid, water, and saturated brine, and then dried over anhydrous sodium sulfate. After filtering off the anhydrous sodium sulfate, 1.2 g of silica gel was added to the resulting liquid. This was purified by silica gel column chromatography (2 g of silica gel, mobile phase: dichloromethane). MEHQ was added, and the solvent was evaporated under reduced pressure in the dark. Methanol (12 mL) was added to the residue to reprecipitate, yielding compound (a-4) (2.7 g, 78% yield). [M]:502 (Synthesis Example of a-5 (Example)) (step-1)

[0537] [ka]

[0538] Under a nitrogen atmosphere, 2-(benzoyloxy)phenol (13.0 g, 65 mmol) and acetonitrile (65 mL) were mixed in a reaction vessel equipped with a stirrer, a condenser, and a thermometer and cooled to 5°C. A mixed solution of N-bromosuccinimide (11.7 g, 65.6 mmol) and acetonitrile (117 mL) was added dropwise under ice cooling, followed by stirring for 5 hours. After the reaction was completed, the mixture was returned to room temperature, and then a mixed solution of hexane and ethyl acetate (hexane / ethyl acetate = 4 / 1 to 2 / 1) and water were added and the mixture was separated. The resulting organic layer was washed with saturated saline, and the solvent was evaporated. The residue was then purified by silica gel column chromatography (silica gel 18 g, mobile phase: hexane / ethyl acetate = 4 / 1 to 2 / 1) to obtain compound (S-12) (16.3 g, yield 90%). (step-2)

[0539] [ka]

[0540] Under a nitrogen atmosphere, the compound represented by (S-12) (12.7 g, 45.5 mmol), 5-(bromomethyl)-5-ethyl-2,2-dimethyl-1,3-dioxane (14.0 g, 59.1 mmol), potassium carbonate (18.9 g, 136.5 mmol), and N,N-dimethylformamide (63.5 mL) were mixed in a reaction vessel equipped with a stirrer, heater, and thermometer, and the mixture was reacted at 90°C for 5 hours. After the reaction was completed, the mixture was cooled, and ethyl acetate and water were added for separation. The resulting organic layer was washed with saturated saline and the solvent was distilled off. The mixture was then purified by silica gel column chromatography (silica gel 18 g, mobile phase: toluene) to obtain the compound represented by (S-13) (16.6 g, 84% yield). (step-3)

[0541] [ka]

[0542] Under a nitrogen atmosphere, a reaction vessel equipped with a stirrer, heater, and thermometer was charged with compound (S-13) (6.5 g, 14.9 mmol), (4-hydroxyphenyl)boronic acid (2.2 g, 15.7 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.1 g, 0.15 mmol), and THF (31 mL). The mixture was then heated to 60 °C. A 2 mol / L aqueous potassium carbonate solution (18 mL, 36 mmol) was added dropwise under heating, and the mixture was stirred at 60 °C for 3 hours. After the reaction was completed, the mixture was cooled, and ethyl acetate and water were added for separation. The resulting organic layer was washed with saturated brine, and the solvent was evaporated. The residue was then purified by silica gel column chromatography (silica gel 8 g, mobile phase: hexane / ethyl acetate = 4 / 1 to 2 / 1) to obtain compound (S-14) (6.1 g, 91% yield). (step-4)

[0543] [ka]

[0544] A pressure-resistant reactor was charged with the compound represented by (S-14) (6.1 g, 13.6 mmol), palladium carbon (5 wt%, 0.6 g), and THF (48.4 mL), and the reaction was carried out at 40°C for 10 hours under a hydrogen pressure of 0.5 MPa. After the reaction was completed, the mixture was cooled, and ethyl acetate and water were added for separation. The resulting organic layer was washed with saturated saline, and the solvent was distilled off. The mixture was then suspended and washed in a mixed solvent of toluene and hexane (toluene / hexane = 3 / 1 to 1 / 1), yielding the compound represented by (S-15) (4.7 g, yield 97%). (step-5)

[0545] [ka]

[0546] To a mixture of compound (S-15) (3.2 g, 8.9 mmol), methacrylic acid (1.9 g, 22.3 mmol), DMAP (0.25 g, 2.1 mmol), and dichloromethane (22.4 mL) in air, DIC (2.6 g, 20.5 mmol) was added under ice cooling and stirred overnight at room temperature. The precipitate was filtered off, and the resulting liquid was washed with 10% hydrochloric acid, water, and saturated brine, and dried over anhydrous sodium sulfate. After filtering off the anhydrous sodium sulfate, 1.4 g of silica gel was added to the resulting liquid. This was purified by silica gel column chromatography (silica gel 2.6 g, mobile phase: dichloromethane). MEHQ was added, and the solvent was evaporated under reduced pressure in the dark. Methanol (13 mL) was added to the residue to reprecipitate, yielding the target compound (a-5) (3.7 g, 91% yield). [M]:454 [Industrial Applicability]

[0547] The polymerizable compound and the liquid crystal composition containing the polymerizable compound according to the present invention can be used in a liquid crystal display device. [Explanation of symbols]

[0548] 1: Liquid crystal display element 2: First substrate 3: Second board 4: Liquid crystal layer 5: Pixel electrode layer 6: Common electrode layer 7: First polarizing plate 8: Second polarizing plate 9: Color filter

Claims

1. The following general formula (i) 【Chemical 1】 (In the formula, A ｉ１ , A ｉ２ are each independently a 1,4-phenylene group, A ｉ１ , A ｉ２ One or more hydrogen atoms in each independently represent a substituent Sr ｉ１ may be substituted with Substituent Sr ｉ１ is a halogen atom, an alkyl group having 1 to 40 carbon atoms, or S ｉ３ represents one of the following: One or more —CH ２ - may be independently substituted by -O- or -NH-; One or more —CH ２ -CH ２ - may be independently replaced by -CH=CH-, -C≡C-, -CO-O- or -O-CO-; One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, Oxygen atoms do not bond directly to each other, Substituent Sr ｉ１ When there are a plurality of, they may be the same or different. S ｉ１ , Si3 are each independently represented by the formula (S ｉ -1), a group represented by S ｉ２ is the formula (S ｉ -2), 【Chemistry 2】 (Formula (S ｉ -1) Middle, P ｉ１ is the formula (P ｉ１ -1), 【Chemistry 3】 S ｉ11 represents an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms, Sp ｉ１ represents a single bond or a spacer group, * is A ｉ１ , A ｉ２ Represents a bond to . Formula (S ｉ -2) Middle, G ｉ１ , G ｉ２ and G ｉ３ each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, or an arylene group having 6 to 20 carbon atoms; One or more —CH ２ Each - may independently be substituted with -O-; One or more —CH ２ -CH ２ - may be independently replaced by -O-CO- or -CO-O-; One or more hydrogen atoms in the alkylene group and arylene group may be independently substituted with a hydroxyl group, a halogen atom, or an alkyl group having 1 to 6 carbon atoms. Oxygen atoms do not bond directly to each other, R ｉ１ Is, P ｉ１ -Sp ｉ１ -, or an alkyl group having 1 to 20 carbon atoms; P ｉ１ is the formula (P ｉ１ -1), Sp ｉ１ represents a single bond or a spacer group, One or more —CH ２ Each - may independently be substituted with -O-; One or more —CH ２ -CH ２ - may be independently replaced by -O-CO- or -CO-O-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom or an alkyl group having 1 to 6 carbon atoms. Oxygen atoms never bond directly to each other.) L ｉ１ and L ｉ２ are each independently a single bond; n ｉ１ represents 0.) and P ｉ１ and one or more polymerizable compounds having a total of two of the following: One or more liquid crystal compounds A polymerizable compound-containing liquid crystal composition comprising at least the following.

2. 2. The liquid crystal composition according to claim 1, further comprising a polymerizable compound having a structure different from that of the compound represented by formula (i).

3. The liquid crystal compound is represented by the following general formulas (NU-01) to (NU-08): 【Chemistry 4】 (In general formulas (NU-01) to (NU-08), R ＮＵ１１ , R ＮＵ１２ , R ＮＵ２１ , R ＮＵ２２ , R ＮＵ３１ , R ＮＵ３２ , R ＮＵ４１ , R ＮＵ４２ , R ＮＵ５１ , R ＮＵ５２ , R ＮＵ６１ , R ＮＵ６２ , R ＮＵ７１ , R ＮＵ７２ , R ＮＵ８１ and R ＮＵ８２ each independently represents 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; One or more —CH ２ -CH ２ - may be independently replaced by -C≡C-, -CO-, -CO-O- or -O-CO-, Oxygen atoms never bond directly to each other.) 3. The polymerizable compound-containing liquid crystal composition according to claim 1, further comprising a compound selected from the group consisting of compounds represented by any one of the following formulae:

4. Two boards and A liquid crystal display element having a liquid crystal layer between the two substrates, the liquid crystal layer containing the polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 3, A liquid crystal display element in which a polymer obtained by polymerizing the polymerizable compound represented by the general formula (i) is present.

5. The following general formula (i) 【Chemistry 5】 (In the formula, A ｉ１ , A ｉ２ are each independently a 1,4-phenylene group, A ｉ１ , A ｉ２ One or more hydrogen atoms in each independently represent a substituent Sr ｉ１ may be substituted with Substituent Sr ｉ１ is a halogen atom, an alkyl group having 1 to 40 carbon atoms, or S ｉ３ represents one of the following: One or more —CH ２ - may be independently substituted by -O- or -NH-; One or more —CH ２ -CH ２ - may be independently replaced by -CH=CH-, -C≡C-, -CO-O- or -O-CO-; One or more hydrogen atoms in the alkyl group may each independently be substituted with a halogen atom, Oxygen atoms do not bond directly to each other, Substituent Sr ｉ１ When there are a plurality of, they may be the same or different. S ｉ１ , Si3 are each independently represented by the formula (S ｉ -1), a group represented by S ｉ２ is the formula (S ｉ -2), 【Chemistry 6】 (Formula (S ｉ -1) Middle, P ｉ１ is the formula (P ｉ１ -1), 【Chemistry 7】 S ｉ11 represents an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms, Sp ｉ１ represents a single bond or a spacer group, * is A ｉ１ , A ｉ２ Represents a bond to . Formula (S ｉ -2) Middle, G ｉ１ , G ｉ２ and G ｉ３ each independently represents a single bond, an alkylene group having 1 to 20 carbon atoms, or an arylene group having 6 to 20 carbon atoms; One or more —CH ２ Each - may independently be substituted with -O-; One or more —CH ２ -CH ２ - may be independently replaced by -O-CO- or -CO-O-; One or more hydrogen atoms in the alkylene group and arylene group may be independently substituted with a hydroxyl group, a halogen atom, or an alkyl group having 1 to 6 carbon atoms. Oxygen atoms do not bond directly to each other, R ｉ１ Is, P ｉ１ -Sp ｉ１ -, or an alkyl group having 1 to 20 carbon atoms; P ｉ１ is the formula (P ｉ１ -1), Sp ｉ１ represents a single bond or a spacer group, One or more —CH ２ Each - may independently be substituted with -O-; One or more —CH ２ -CH ２ - may be independently replaced by -O-CO- or -CO-O-; One or more hydrogen atoms in the alkyl group may be independently substituted with a halogen atom or an alkyl group having 1 to 6 carbon atoms. Oxygen atoms never bond directly to each other.) L ｉ１ and L ｉ２ are each independently a single bond; n ｉ１ represents 0.) and P ｉ１ A polymerizable compound having a total of two of the above.

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