Use of a compound, use of a liquid crystal composition, and liquid crystal display element

Abstract

The present invention provides a compound, a liquid crystal composition, and a liquid crystal display element. The present invention provides a compound having at least one of the characteristics of high chemical stability, high ability to horizontally align liquid crystal molecules, high alignment property in a wide addition concentration range, appropriate reactivity, and high solubility in a liquid crystal composition. The present invention provides a compound of the following formula (1). In formula (1), a and b are independently 0, 1, or 2, the sum of a and b is 0, 1, 2, or 3, ring A 1 , ring A 2 , ring A 3 , and ring A 4 are independently, for example, 1,4-cyclohexylene, Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, etc., Sp 1 , and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, etc., P 1 , and P 2 are independently a specific polymerizable group.

Description

Technical Field

[0001] The present invention relates to a compound, a liquid crystal composition, and a liquid crystal display element. More specifically, the present invention relates to a polymerizable polar compound having a 9,10-dihydrophenanthrene condensed ring in the molecule, a liquid crystal composition containing the compound and having positive or negative dielectric anisotropy, and a liquid crystal display element containing the composition. Background Art

[0002] In liquid crystal display elements, classification based on the operation mode of liquid crystal molecules includes phase change (PC), twisted nematic (TN), super twisted nematic (STN), electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (VA), fringe field switching (FFS), field-induced photo-reactive alignment (FPA), and other modes. Classification based on the driving method of the element includes passive matrix (PM) and active matrix (AM). PM is classified into static, multiplex, etc., and AM is classified into thin film transistor (TFT), metal insulator metal (MIM), etc. TFT is classified into amorphous silicon and polycrystalline silicon. The latter is classified into high temperature type and low temperature type according to the manufacturing process. Classification based on the light source includes a reflective type using natural light, a transmissive type using a backlight, and a transflective type using both natural light and a backlight.

[0003] The liquid crystal display element contains a liquid crystal composition having a nematic phase. The composition has appropriate properties. By improving the properties of the composition, an AM element with good properties can be obtained. The correlations between the two properties are summarized in Table 1 below. The properties of the composition will be further described based on commercially available AM elements. The temperature range of the nematic phase is associated with the temperature range in which the element can be used. The preferred upper limit temperature of the nematic phase is about 70 °C or higher, and the preferred lower limit temperature of the nematic phase is about -10 °C or lower. The viscosity of the composition is associated with the response time of the element. In order to display moving images using the element, a short response time is preferred. An ideal response time is shorter than 1 millisecond. Therefore, it is preferred that the viscosity of the composition is small. More preferably, the viscosity is small at low temperatures.

[0004] Table 1. Properties of the Composition and the AM Element

[0005]

[0006] 1) The time for injecting the composition into the liquid crystal display element can be shortened

[0007] The optical anisotropy of the composition is associated with the contrast ratio of the element. Depending on the mode of the element, a large optical anisotropy or a small optical anisotropy, i.e., an appropriate optical anisotropy, is required. The product (Δn × d) of the optical anisotropy (Δn) of the composition and the cell gap (d) of the element is designed to maximize the contrast ratio. The appropriate value of the product depends on the type of operation mode. In the case of an element in a mode such as TN, the value is about 0.45 μm. In the case of an element in the VA mode, the value is in the range of about 0.30 μm to about 0.40 μm, and in the case of an element in the IPS mode or FFS mode, the value is in the range of about 0.20 μm to about 0.30 μm. In these cases, for an element with a small cell gap, a composition having a large optical anisotropy is preferred. A large dielectric anisotropy of the composition contributes to a low threshold voltage, low power consumption, and a large contrast ratio of the element. Therefore, a large positive or negative dielectric anisotropy is preferred. A large specific resistance of the composition contributes to a large voltage holding ratio and a large contrast ratio of the element. Therefore, it is preferred that the composition has a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase in the initial stage. It is preferred that the composition has a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after long-term use. The stability of the composition to ultraviolet rays and heat is associated with the life of the element. When the stability is high, the life of the element is long. Such a property is preferred for AM elements used in liquid crystal projectors, liquid crystal TVs, etc.

[0008] A composition having positive dielectric anisotropy is used in an AM element having a TN mode. A composition having negative dielectric anisotropy is used in an AM element having a VA mode. A composition having positive or negative dielectric anisotropy is used in an AM element having an IPS mode or an FFS mode.

[0009] A composition having positive or negative dielectric anisotropy is used in a polymer sustained alignment (PSA) type AM element. A liquid crystal composition containing a polymer is used in a polymer sustained alignment (PSA) type liquid crystal display element. First, a composition added with a small amount of a polymerizable compound is injected into the element. Then, while applying a voltage between the substrates of the element, ultraviolet rays are irradiated to the composition. The polymerizable compound polymerizes to form a polymer network structure in the composition. In the composition, the orientation of liquid crystal molecules can be controlled by the polymer, so the response time of the element is shortened and image burn-in is improved. Such an effect of the polymer can be expected for elements having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

[0010] The following method has been reported: Instead of an alignment film such as polyimide, a low molecular compound having a cinnamate group, a low molecular compound having a polyvinyl cinnamate or chalcone structure, a low molecular compound having an azobenzene structure, or a dendrimer is used to control the orientation of liquid crystal (Patent Document 1, Patent Document 2, or Patent Document 3). In the methods of Patent Document 1, Patent Document 2, or Patent Document 3, first, the low molecular compound or polymer is dissolved in the liquid crystal composition in the form of an additive. Then, by phase-separating the additive, a thin film containing the low molecular compound or polymer is formed on the substrate. Finally, linearly polarized light is irradiated to the substrate at a temperature higher than the upper limit temperature of the liquid crystal composition. When the low molecular compound or polymer dimerizes or isomerizes by the linearly polarized light, its molecules are aligned in a certain direction. In this method, by selecting the type of the low molecular compound or polymer, elements having a horizontal alignment mode such as IPS or FFS and elements having a vertical alignment mode such as VA can be manufactured. In this method, it is important that the low molecular compound or polymer is easily soluble at a temperature higher than the upper limit temperature of the liquid crystal composition, and when the temperature returns to room temperature, the compound is easily phase-separated from the liquid crystal composition. Among them, it is difficult to ensure the compatibility between the low molecular compound or polymer and the liquid crystal composition.

[0011] Hitherto, in liquid crystal display elements without an alignment film, as compounds capable of horizontally aligning liquid crystal molecules, compound (S-1) (Formula 2 in paragraph 0034 of the specification) is described in Patent Document 2, and compound (S-2) (Compound

[14] on P176 in the specification) is described in Patent Document 3, etc. However, the various characteristics of liquid crystal display elements made using these compounds are not sufficient, and improvement is desired.

[0012]

[0013] [Prior Art Documents]

[0014] [Patent Documents]

[0015] [Patent Document 1] International Publication No. 2015 / 146369

[0016] [Patent Document 2] International Publication No. 2017 / 057162

[0017] [Patent Document 3] International Publication No. 2017 / 102068 Summary of the Invention

[0018] [Problems to be Solved by the Invention]

[0019] The first object of the present invention is to provide a compound having at least one of the characteristics of high chemical stability, high ability to horizontally align liquid crystal molecules, high alignment property in a wide additive concentration range, appropriate reactivity, and high solubility in a liquid crystal composition, and having a large voltage holding ratio when expected to be used in a liquid crystal display element. The second object is to provide a liquid crystal composition containing the compound and satisfying at least one of the characteristics of a high upper limit temperature of the nematic phase, a low lower limit temperature of the nematic phase, low viscosity, appropriate optical anisotropy, large positive or negative dielectric anisotropy, large specific resistance, high stability to ultraviolet rays, high stability to heat, and large elastic constant. The third object is to provide a liquid crystal display element containing the composition, and when a polar compound forms a film in the element by irradiating the composition with ultraviolet rays, the film has at least one of the characteristics of appropriate hardness, low permeability of the contact component, high weather resistance, and appropriate volume resistance value, and the liquid crystal display element has at least one of the characteristics of a wide temperature range in which the element can be used, short response time, high voltage holding ratio, low threshold voltage, large contrast ratio, long life, and low AC afterimage.

[0020] [Technical Means for Solving the Problems]

[0021] The present inventors found that the compound represented by the following formula (1) can solve the above problems, and thus completed the invention.

[0022]

[0023] (The explanations of the notations in the formula will be described below.)

[0024] The present invention includes the following items and the like.

[0025] A compound represented by formula (1).

[0026]

[0027] In formula (1),

[0028] a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1, 2 or 3;

[0029] Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopentano[a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopentano[a]phenanthrene-3,17-diyl, a group represented by formula (A-1) or formula (A-2). For these Ring As 1 , Ring A 2 , Ring A 3 and Ring A 4 , at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 , and at least one hydrogen in these alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, -Sp 1 -P 1 or -Sp 2 -P 2 may be substituted by fluorine or chlorine. Among them, at least one of Ring A 1 , Ring A 2 , Ring A 3 or Ring A 4 is a group represented by formula (A-1) or formula (A-2). In formula (A-1) and formula (A-2), Q 1 and Q 2 are independently -CH2-, -O-, -N(-R8 )- or -S-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine;

[0030]

[0031] When a is 2, the two rings A 1 may be different, and when b is 2, the two rings A 4 may be different;

[0032] Z 1 、Z 2 、Z 3 、Z 4 and Z 5 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in said Z 1 、Z 2 、Z 3 、Z 4 and Z 5 , at least one -CH2- may be substituted by -O-, -S-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that at least one of Z 2 、Z 3 or Z 4 is -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -COO-, -OCO-, -CH=CH-, -CH=CHCO- or -COCH=CH-, and when a is 2, the two Z 1 may be different, and when b is 2, the two Z 5 may be different;

[0033] Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in said Sp 1 and Sp 2 , at least one -CH2- may be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 ;

[0034] In the case where there are multiple Sp 1 or Sp 2 , any two of them may be different;

[0035] P 1 and P 2 are independently a group represented by any one of Formula (1b) to Formula (1h). In the case where there are multiple P 1 or P 2 , any two of them may be different;

[0036]

[0037] In Formula (1b) to Formula (1h),

[0038] M 1 , M 2 , M 3 and M 4 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted with fluorine or chlorine; X 1 is -N(-R 9 ), -O-, or -S-. Here, R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms. In the R 9 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine;

[0039] R 2 and R 6 are independently hydrogen, fluorine, chlorine, or an alkyl group having 1 to 5 carbon atoms. In the R 2 and R 6 , at least one hydrogen may be substituted with fluorine or chlorine, and at least one -CH2- may be substituted with -O-;

[0040] R 3 , R 4 , R 5 and R 7 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms. In the R 3 , R 4 , R 5 and R 7 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 5 and R 7 are fluorine or chlorine.

[0041] A liquid crystal composition containing at least one of the above-mentioned compounds.

[0042] A liquid crystal display element containing the above-mentioned liquid crystal composition.

[0043] [Advantages of the Invention]

[0044] The first advantage of the present invention is to provide a compound having at least one of high chemical stability, high ability to horizontally align liquid crystal molecules, high alignment property in a wide additive concentration range, appropriate reactivity, and high solubility in a liquid crystal composition, and a large voltage holding ratio can be expected when used in a liquid crystal display element. The second advantage is to provide a liquid crystal composition containing the compound and satisfying at least one of the characteristics of a high upper limit temperature of the nematic phase, a low lower limit temperature of the nematic phase, low viscosity, appropriate optical anisotropy, large positive or negative dielectric anisotropy, large specific resistance, high stability to ultraviolet rays, high stability to heat, and large elastic constant. The third advantage is to provide a liquid crystal display element containing the composition. When a polar compound forms a film in the element by irradiating the composition with ultraviolet rays, the film has at least one of the characteristics of appropriate hardness, low permeability of the contact component, high weather resistance, and appropriate volume resistance value, and the liquid crystal display element has at least one of the characteristics of a wide temperature range in which the element can be used, short response time, high voltage holding ratio, low threshold voltage, large contrast ratio, long life, and low AC afterimage. By using a liquid crystal composition containing the compound of the present invention, the step of forming an alignment film is not required, and thus a liquid crystal display element with reduced manufacturing cost can be obtained. Detailed Embodiments

[0045] The usage of the terms in this specification is as described below. Sometimes, the terms "liquid crystal composition" and "liquid crystal display element" are abbreviated as "composition" and "element", respectively. "Liquid crystal display element" is a general term for a liquid crystal display panel and a liquid crystal display module. "Liquid crystalline compound" is a general term for a compound having a liquid crystal phase such as a nematic phase or a smectic phase, and a compound that does not have a liquid crystal phase but is mixed into the composition for the purpose of adjusting characteristics such as the temperature range of the nematic phase, viscosity, and dielectric anisotropy. The compound has a six-membered ring such as 1,4-cyclohexylene or 1,4-phenylene, and its molecular structure is rod-like. "Polymerizable compound" is a compound added for the purpose of generating a polymer in the composition. "Polar compound" helps the alignment of liquid crystal molecules by interacting with the substrate surface through a polar group.

[0046] A liquid crystal composition is prepared by mixing a plurality of liquid crystalline compounds. The ratio (content) of the liquid crystalline compounds is expressed as a weight percentage (wt%) based on the weight of the liquid crystal composition. Additives such as an optically active compound, an antioxidant, an ultraviolet absorber, a pigment, an antifoaming agent, a polymerizable compound, a polymerization initiator, a polymerization inhibitor, and a polar compound are added as needed to the liquid crystal composition. Similarly to the ratio of the liquid crystalline compounds, the ratio (addition amount) of the additives is expressed as a weight percentage (wt%) based on the weight of the liquid crystal composition. Sometimes parts per million by weight (ppm) is also used. The ratios of the polymerization initiator and the polymerization inhibitor are expressed based on the weight of the polymerizable compound, except in some cases.

[0047] Sometimes, the compound represented by the formula (1) is simply referred to as "compound (1)". Compound (1) refers to one compound represented by the formula (1), a mixture of two compounds, or a mixture of three or more compounds. The same rule applies to at least one compound selected from the group of compounds represented by the formula (2), etc. B surrounded by a hexagon 1 , C 1 , F and other notations respectively correspond to ring B 1 , ring C 1 , ring F, etc. The hexagon represents a six-membered ring such as a cyclohexane ring or a benzene ring, or a condensed ring such as a naphthalene ring. The slant line cutting the hexagon indicates that any hydrogen on the ring can be substituted by a group such as -Sp 1 -P 1 , etc. Subscripts such as e represent the number of substituted groups. When the subscript is 0, such substitution does not exist.

[0048] As described later, the notation of the terminal group R 11 is used for a plurality of component compounds. Among these compounds, the two groups represented by any two R 11 may be the same or different. For example, there is a case where R 11 of compound (2) is ethyl and R 11 of compound (3) is ethyl. There is also a case where R 11 of compound (2) is ethyl and R 11 of compound (3) is propyl. The same rule applies to notations of other terminal groups, rings, bonding groups, etc. In the formula (8) described later, when i is 2, there are two rings D 1 . Among the compounds, the two groups represented by the two rings D 1 may be the same or different. The same rule applies to any two rings D 1 when i is greater than 2. The same rule applies to notations of other rings, bonding groups, etc.

[0049] The expression "at least one 'A'" means that the number of 'A's is arbitrary. Regarding the expression "at least one 'A' can be replaced by 'B'", when the number of 'A's is one, the position of 'A' is arbitrary, and when the number of 'A's is two or more, the positions of these 'A's can also be selected without limitation. The said rule also applies to the expression "at least one 'A' is replaced by 'B'". The expression "at least one A can be replaced by B, C or D" means including the case where at least one A is replaced by B, the case where at least one A is replaced by C, the case where at least one A is replaced by D, and the case where multiple A's are replaced by at least two of B, C, and D. For example, in an alkyl group where at least one -CH2- (or -(CH2)2-) can be replaced by -O- (or -CH=CH-), it includes alkyl, alkenyl, alkoxy, alkoxyalkyl, alkoxyalkenyl, alkenyloxyalkyl. Furthermore, the case where two consecutive -CH2-'s are replaced by -O- to become like -O-O- is not preferred.

[0050] Halogen means fluorine, chlorine, bromine or iodine. Preferred halogens are fluorine or chlorine. Further preferred halogen is fluorine. The alkyl group is linear or branched and does not include a cyclic alkyl group. Generally, a linear alkyl group is superior to a branched alkyl group. These cases are the same for terminal groups such as alkoxy and alkenyl. Regarding the stereoconfiguration related to 1,4-cyclohexylene, in order to increase the upper limit temperature of the nematic phase, the trans configuration is superior to the cis configuration. 2-Fluoro-1,4-phenylene means the following two divalent groups. In the chemical formula, fluorine can be on the left (L) or on the right (R). The said rule also applies to an asymmetric divalent group such as tetrahydropyran-2,5-diyl formed by removing two hydrogens from the ring.

[0051]

[0052] The present invention includes the following items, etc.

[0053] Item 1 A compound represented by formula (1).

[0054]

[0055] In formula (1),

[0056] a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1, 2 or 3;

[0057] Ring A 1 、Ring A 2 、Ring A 3 and Ring A 4Independently being 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, a group represented by formula (A-1) or formula (A-2), and for these ring A 1 、ring A 2 、ring A 3 and ring A 4 in, at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 substituted, and in these alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, -Sp 1 -P 1 or -Sp 2 -P 2 in, at least one hydrogen may be substituted by fluorine or chlorine, wherein, ring A 1 、ring A 2 、ring A 3 or ring A 4 at least one of which is a group represented by formula (A-1) or formula (A-2), in formula (A-1) and formula (A-2), Q 1 and Q 2 independently being -CH2-, -O-, -N(-R 8 )- or -S-, here, R 8 being hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, but there is no case where R 8 is fluorine or chlorine;

[0058]

[0059] When a is 2, the two ring A 1 may be different, and when b is 2, the two ring A 4 may be different;

[0060] Z 1 、Z 2, Z 3 , Z 4 and Z 5 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Z 1 , Z 2 , Z 3 , Z 4 and Z 5 , at least one -CH2- may be substituted with -O-, -S-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that at least one of the Z 2 , Z 3 or Z 4 is -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -COO-, -OCO-, -CH=CH-, -CH=CHCO- or -COCH=CH-. When a is 2, the two Z 1 may be different. When b is 2, the two Z 5 may be different;

[0061] Sp 1 and Sp 2 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp 1 and Sp 2 , at least one -CH2- may be substituted with -O-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 ;

[0062] In the case where there are multiple Sp 1 or Sp 2 , any two of them may be different;

[0063] P 1 and P 2 are each independently a group represented by any one of formulas (1b) to (1h). In the case where there are multiple P 1 or P 2 , any two of them may be different;

[0064]

[0065] In formulas (1b) to (1h),

[0066] M 1 , M 2, M 3 and M 4 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted with fluorine or chlorine; X 1 is -N(-R 9 ), -O-, or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 9 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine;

[0067] R 2 and R 6 are independently hydrogen, fluorine, chlorine, or an alkyl group having 1 to 5 carbon atoms, and in said R 2 and R 6 , at least one hydrogen may be substituted with fluorine or chlorine, and at least one -CH2- may be substituted with -O-;

[0068] R 3 , R 4 , R 5 and R 7 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 3 , R 4 , R 5 and R 7 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 5 and R 7 are fluorine or chlorine.

[0069] The compound according to item 2, wherein in formula (1),

[0070] a and b are independently 0, 1, or 2, and the sum of a and b is 0, 1, or 2;

[0071] Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4Independently being 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopentano[a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopentano[a]phenanthrene-3,17-diyl, a group represented by formula (A-1) or formula (A-2), and for these ring A 1 、ring A 2 、ring A 3 and ring A 4 in, at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 substituted, and for these alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, -Sp 1 -P 1 or -Sp 2 -P 2 in, at least one hydrogen may be substituted by fluorine or chlorine, wherein, ring A 1 、ring A 2 、ring A 3 or ring A 4 at least one of which is a group represented by formula (A-1) or formula (A-2), Q 1 and Q 2 independently being -CH2-, -O-, -N(R 8 )-, or -S-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and for the said R 8 in, at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine, but there is no case where R 8 is fluorine or chlorine,

[0072]

[0073] When a is 2, the two ring A 1 may be different, and when b is 2, the two ring A 4 may be different;

[0074] Z 1 、Z 2 、Z 3, Z 4 and Z 5 are independently a single bond, -(CH2)2-, -C≡C-, -C≡C-C≡C-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CF=CF-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-; when a is 2, the two Z 1 may be different, and when b is 2, the two Z 5 may be different;

[0075] Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp 1 and Sp 2 , at least one -CH2- may be substituted with -O-, -COO- or -OCO-, at least one -(CH2)2- may be substituted with -CH=CH-, and at least one hydrogen may be substituted with fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 substituted, and in the case of the presence of a plurality of Sp 1 or Sp 2 , they may be different respectively;

[0076] P 1 and P 2 are independently a group represented by any one of Formula (1b) to Formula (1h), and in the case of the presence of a plurality of P 1 or P 2 , any two of them may be different;

[0077]

[0078] In Formula (1b) to Formula (1h),

[0079] M 1 , M 2 , M 3 and M 4 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted with fluorine or chlorine, and X 1 is -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and the R 9in which at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine;

[0080] R 2 and R 6 are hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and in said R 2 and R 6 at least one hydrogen may be replaced by fluorine or chlorine, and at least one -CH2- may be replaced by -O-;

[0081] R 3 , R 4 , R 5 and R 7 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 3 , R 4 , R 5 and R 7 at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, provided that there is no case where R 5 and R 7 is fluorine or chlorine.

[0082] The compound according to item 3, according to item 1 or item 2, is represented by any one of formulas (1-1) to (1-3).

[0083]

[0084] In formulas (1-1) to (1-3),

[0085] ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, a group represented by formula (A-1) or formula (A-2), and in these ring As 1 , ring A 2 , ring A 3 and ring A 4 at least one hydrogen may be replaced by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P2 are substituted, and at least one hydrogen in these alkyl, alkenyl, alkoxy, alkenyloxy, -Sp 1 -P 1 or -Sp 2 -P 2 can be substituted by fluorine or chlorine, wherein at least one of Ring A 1 , Ring A 2 , Ring A 3 or Ring A 4 is of formula (A-1) or formula (A-2), and Q 1 and Q 2 are independently -CH2-, -O-, -N(R 8 )-, or -S-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 8 , at least one -CH2- can be substituted by -O- or -S-, at least one -(CH2)2- can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine.

[0086]

[0087] Z 2 , Z 3 and Z 4 are independently a single bond, -(CH2)2-, -C≡C-, -C≡C-C≡C-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CF=CF-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-;

[0088] Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in said Sp 1 and Sp 2 , at least one -CH2- can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- can be substituted by -CH=CH-, and at least one hydrogen can be substituted by fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 substituted, and in the case where there are multiple Sp 1 or Sp 2 , they can be different respectively;

[0089] P1 and P 2 independently represents a group represented by any one of formulas (1b) to (1h), and in the case where there are a plurality of P 1 or P 2 any two of them may be different;

[0090]

[0091] In formulas (1b) to (1h),

[0092] M 1 、M 2 、M 3 and M 4 independently represents hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted with fluorine or chlorine; X 1 is -N(-R 9 )-, -O-, or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the R 9 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine;

[0093] R 2 and R 6 are hydrogen, fluorine, chlorine, or an alkyl group having 1 to 5 carbon atoms, and in the R 2 and R 6 , at least one hydrogen may be substituted with fluorine or chlorine, and at least one -CH2- may be substituted with -O-;

[0094] R 3 、R 4 、R 5 and R 7 independently represents hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the R 3 、R 4 、R 5 and R 7 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 5 and R 7 are fluorine or chlorine.

[0095] The compound according to item 4 according to item 3, wherein in formulas (1-1) to (1-3),

[0096] Ring A 1 、Ring A 2, Ring A 3 and Ring A 4 are independently 1,4 - cyclohexylene, 1,4 - phenylene, naphthalene - 2,6 - diyl, fluorene - 2,7 - diyl, phenanthrene - 2,7 - diyl, the group represented by formula (A - 1) or formula (A - 2). At least one hydrogen in these Ring As 1 , Ring A 2 , Ring A 3 and Ring A 4 can be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 . Among them, at least one of Ring A 1 , Ring A 2 , Ring A 3 or Ring A 4 is the group represented by formula (A - 1) or formula (A - 2). Q 1 and Q 2 are independently -CH2-, -O-, -N(R 8 )-, or -S-. Here, R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms. Among the Rs 8 , at least one -CH2- can be substituted by -O- or -S-, at least one -(CH2)2- can be substituted by -CH = CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine.

[0097]

[0098] Z 2 , Z 3 and Z 4 are independently a single bond, -(CH2)2-, -C≡C-C≡C-, -C≡C-, -COO-, -OCO-, -CH = CHCOO-, -OCOCH = CH-, -CH = CH-, -CH = CHCO-, -COCH = CH-, -COS-, -SCO-, -CH = CHCOS- or -SCOCH = CH-;

[0099] Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms. Among the Sp 1 and Sp 2 , at least one -CH2- can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- can be substituted by -CH = CH-, and at least one hydrogen can be substituted by -Sp1 -P 1 or -Sp 2 -P 2 substituted, and in the presence of multiple Sp 1 or Sp 2 they may be different respectively;

[0100] P 1 and P 2 are independently a group represented by any one of formula (1b), formula (1c), formula (1d) or formula (1e), and in the presence of multiple P 1 or P 2 any two of them may be different;

[0101]

[0102] In formula (1b) to formula (1e),

[0103] M 1 、M 2 、M 3 and M 4 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine, X 1 is -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the said R 9 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine, but there is no case where R 9 is fluorine or chlorine;

[0104] R 2 and R 6 are hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and in the said R 2 and R 6 , at least one hydrogen may be substituted by fluorine or chlorine, at least one -CH2- may be substituted by -O-;

[0105] R 3 、R 4 and R 5 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the said R 3 、R 4 and R 5 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine, but there is no case where R 5 is fluorine or chlorine.

[0106] Item 5. The compound according to item 3, wherein, in Formula (1-1) to Formula (1-3),

[0107] Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, Formula (A-1) or Formula (A-2), and at least one hydrogen in these Ring As 1 , Ring A 2 , Ring A 3 and Ring A 4 may be substituted by fluorine, chlorine, methyl or ethyl, wherein at least one of Ring A 1 , Ring A 2 , Ring A 3 or Ring A 4 is Formula (A-1) or Formula (A-2), Q 1 and Q 2 are independently -CH2-, -O-, -N(R 8 )-, or -S-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine,

[0108]

[0109] Z 2 , Z 3 and Z 4 are independently a single bond, -(CH2)2-, -C≡C-C≡C-, -C≡C-, -COO-, -OCO-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-;

[0110] Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in said Sp 1 and Sp 2 , at least one -CH2- may be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- may be substituted by -CH=CH-, and at least one hydrogen may be substituted by -Sp1 -P 1 or -Sp 2 -P 2 is replaced, and in the presence of multiple Sp 1 or Sp 2 any two of them may be different;

[0111] P 1 and P 2 are independently a group represented by formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) or formula (1e-1),

[0112]

[0113] In formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) and formula (1e-1),

[0114] X 2 、X 3 、X 4 、X 5 and X 6 are independently -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 9 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine.

[0115] The compound according to item 6, wherein, in the compounds represented by formula (1-1) to formula (1-3), any one of Z 2 , Z 3 or Z 4 is -COO- or -OCO-, Q 1 is -CH2- or -N(R 8 )-, Q 2 is -N(R 8 )-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine.

[0116] The compound according to any one of items 1 to 6, which is represented by any one of the following formulas.

[0117]

[0118]

[0119]

[0120]

[0121] In these formulas,

[0122] Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp 1 and Sp 2 , at least one -CH2- can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- can be substituted by -CH=CH-, and at least one hydrogen can be substituted by -Sp 1 -P 1 or -Sp 2 -P 2 ;

[0123] P 1 、P 2 、Sp 1 and Sp 2 In the partial structure other than, at least one hydrogen can be substituted by fluorine, chlorine, methyl or ethyl;

[0124] Q 1 is -CH2- or -N(R 8 ), Q 2 is -N(R 8 ), where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the R 8 , at least one -CH2- can be substituted by -O- or -S-, at least one -(CH2)2- can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine, but there is no case where R 8 is fluorine or chlorine,

[0125] P 1 and P 2 are independently a group represented by formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) or formula (1e-1),

[0126]

[0127] In formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) or formula (1e-1), X 2 , X 3 , X 4 , X 5 and X 6 are independently -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 9 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine.

[0128] The compound according to item 8, wherein, in the compounds represented by formula (1-1-11-1) to formula (1-1-11-2), formula (1-2-11-1) to formula (1-2-11-4), formula (1-1-12-1) to formula (1-1-12-2), formula (1-2-12-1) to formula (1-2-12-4), formula (1-1-21-1) to formula (1-1-21-2), formula (1-2-21-1) to formula (1-2-21-4), formula (1-1-22-1) to formula (1-1-22-2) or formula (1-2-22-1) to formula (1-2-22-4), Sp 1 and Sp 2 are independently an alkylene group having 1 to 10 carbon atoms, and in said Sp 1 and Sp 2 , at least one -CH2- may be substituted by -O-, and at least one hydrogen may be substituted by fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 .

[0129] Item 9 A liquid crystal composition containing at least one compound according to any one of Items 1 to 8.

[0130] Item 10 The liquid crystal composition according to Item 9, which further contains at least one compound selected from the group consisting of the compounds represented by formula (2) to formula (4).

[0131]

[0132] In formula (2) to formula (4),

[0133] R 11 and R 12 are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in the case of said R 11 and R 12 at least one -CH2- may be substituted by -O-, and at least one hydrogen may be substituted by fluorine;

[0134] Ring B 1 , Ring B 2 , Ring B 3 and Ring B 4 are independently 1,4 - cyclohexylene, 1,4 - phenylene, 2 - fluoro - 1,4 - phenylene, 2,5 - difluoro - 1,4 - phenylene or pyrimidine - 2,5 - diyl;

[0135] Z 11 , Z 12 and Z 13 are independently a single bond, -(CH2)2-, -CH=CH-, -C≡C- or -COO-.

[0136] The liquid crystal composition according to item 11 and item 9 or item 10 further contains at least one compound selected from the group consisting of the compounds represented by formula (5) to formula (7).

[0137]

[0138] In formula (5) to formula (7),

[0139] R 13 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in the case of said R 13 at least one -CH2- may be substituted by -O-, and at least one hydrogen may be substituted by fluorine;

[0140] X 11 is fluorine, chlorine, -OCF3, -OCHF2, -CF3, -CHF2, -CH2F, -OCF2CHF2 or -OCF2CHFCF3;

[0141] Ring C 1 , Ring C 2 and Ring C 3 are independently 1,4 - cyclohexylene, 1,4 - phenylene in which at least one hydrogen may be substituted by fluorine, tetrahydropyran - 2,5 - diyl, 1,3 - dioxane - 2,5 - diyl or pyrimidine - 2,5 - diyl;

[0142] Z 14 , Z 15 and Z 16Independently a single bond, -(CH2)2-, -CH=CH-, -CH=CF-, -CF=CF-, -C≡C-, -COO-, -CF2O-, -OCF2-, -CH2O-, -CH=CF-CF2O-, -CF=CF-CF2O- or -(CH2)4-;

[0143] L 11 and L 12 Independently are hydrogen or fluorine.

[0144] The liquid crystal composition according to any one of Items 9 to 11 in Item 12 further contains at least one compound selected from the group of compounds represented by Formula (8).

[0145]

[0146] In Formula (8),

[0147] R 14 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in the said R 14 at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine;

[0148] X 12 is -C≡N or -C≡C-C≡N;

[0149] Ring D 1 Independently is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

[0150] Z 17 Independently is a single bond, -(CH2)2-, -C≡C-, -COO-, -CF2O-, -OCF2- or -CH2O-;

[0151] L 13 and L 14 Independently are hydrogen or fluorine;

[0152] i is 1, 2, 3 or 4.

[0153] The liquid crystal composition according to any one of Items 9 to 12 in Item 13 further contains at least one compound selected from the group of compounds represented by Formula (9) to Formula (15), Formula (DB-1) and Formula (DB-2).

[0154]

[0155] In Formula (9) to Formula (15),

[0156] R 15and R 16 independently represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and said R 15 and R 16 wherein at least one -CH2- can be replaced by -O-, and at least one hydrogen can be replaced by fluorine;

[0157] R 17 represents hydrogen, fluorine, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and said R 17 wherein at least one -CH2- can be replaced by -O-, and at least one hydrogen can be replaced by fluorine, provided that there is no case where R 17 is fluorine;

[0158] Ring E 1 , Ring E 2 , Ring E 3 and Ring E 4 independently represents 1,4 - cyclohexylene, 1,4 - cyclohexenylene, 1,4 - phenylene in which at least one hydrogen can be replaced by fluorine, tetrahydropyran - 2,5 - diyl or decahydronaphthalene - 2,6 - diyl;

[0159] Ring E 5 and Ring E 6 independently represents 1,4 - cyclohexylene, 1,4 - cyclohexenylene, 1,4 - phenylene, tetrahydropyran - 2,5 - diyl or decahydronaphthalene - 2,6 - diyl;

[0160] Z 18 , Z 19 , Z 20 and Z 21 independently represents a single bond, -(CH2)2-, -COO-, -CH2O-, -OCF2- or -OCF2-(CH2)2-;

[0161] L 15 and L 16 independently represents fluorine or chlorine;

[0162] S 11 represents hydrogen or methyl;

[0163] X independently represents -CHF- or -CF2-;

[0164] j, k, m, n, p, q, r and s independently represent 0 or 1, the sum of k, m, n and p is 0, 1, 2 or 3, the sum of q, r and s is 0, 1, 2 or 3, and t is 1, 2 or 3;

[0165] In Formula (DB - 1) and Formula (DB - 2),

[0166] X 100 independently represents -S-, -O- or -CH2-;

[0167] a 100 and a 200 are independently 0, 1 or 2, and the sum of a 100 and a 200 is 0, 1, 2 or 3;

[0168] R 100 and R 200 are independently hydrogen, an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in the R 100 and R 200 , at least one -CH2- can be substituted by -O-, at least one hydrogen can be substituted by fluorine, but there is no case where R 100 and R 200 is fluorine;

[0169] A 100 and A 200 are independently 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentene-1,2-diyl, 1,4-cyclohexylene, 1,4-cyclohexene-1,2-diyl, 1,4-cycloheptylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-xanthene-2,6-diyl or 9H-fluorene-2,7-diyl, and in the A 100 and A 200 , at least one hydrogen can be substituted by fluorine, chlorine, -CF3, -CHF2, -CH2F, -OCF3, -OCHF2, -OCH2F or -C≡N;

[0170] Z 100 and Z 200 are independently a single bond or an alkylene group having 1 to 6 carbon atoms, and in the Z 100 and Z 200 , at least one -CH2- can be substituted by -O-, -S-, -CO-, -COO-, -OCO-, -CF2O-, -OCF2-, -(CH2)3O-, -O(CH2)3-, -CH=CH-CH2O-, -OCH2-CH=CH- or -SiH2-, at least one -(CH2)2- can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine;

[0171] L 100 and L 101 are independently fluorine, chlorine, -CF3 or -CHF2;

[0172] L 102 , L 103 , L 104 and L 105 are independently hydrogen, fluorine, chlorine, -CF3, -CHF2, -CH2F, -OCF3, -OCHF2 or -OCH2F, and L is absent. 102 , L 103 , L 104 and L 105 All hydrogen, but L 102 , L 103 , L 104 and L 105 Any one or both of may be hydrogen.

[0173] Item 14: The liquid crystal composition according to any one of Items 9 to 13, comprising at least one polymerizable compound selected from the group of compounds represented by Formula (16).

[0174]

[0175] In formula (16),

[0176] Ring F and Ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxan-2-yl, pyrimidin-2-yl or pyridin-2-yl, and in these Ring F and Ring I, at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine;

[0177] Ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and in these rings G, at least one hydrogen may be substituted with fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which at least one hydrogen is substituted with fluorine or chlorine;

[0178] Z 22 and Z 23 is independently a single bond or an alkylene group having 1 to 10 carbon atoms, wherein Z 22 and Z 23In the above, at least one -CH2- may be replaced by -O-, -CO-, -COO- or -OCO-, at least one -(CH2)2- may be replaced by -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)- or -C(CH3)=C(CH3)-, and at least one hydrogen may be replaced by fluorine or chlorine;

[0179] P 11 , P 12 and P 13 are independently polymerizable groups selected from the group of groups represented by formula (P-1) to formula (P-5);

[0180]

[0181] M 11 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, wherein M 11 In the above, at least one hydrogen may be replaced by fluorine or chlorine, and at least one -CH2- may be replaced by -O-; M 12 and M 13 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine or chlorine;

[0182] Sp 11 、Sp 12 and Sp 13 is independently a single bond or an alkylene group having 1 to 10 carbon atoms, wherein Sp 11 、Sp 12 and Sp 13 In the above, at least one -CH2- may be replaced by -O-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine;

[0183] u is 0, 1 or 2;

[0184] f, g and h are independently 0, 1, 2, 3 or 4, and the sum of f, g and h is 2 or more.

[0185] Item 15. The liquid crystal composition according to any one of Items 9 to 14, comprising at least one polymerizable compound selected from the group of compounds represented by Formula (16-1) to Formula (16-28).

[0186]

[0187]

[0188]

[0189] In formula (16-1) to formula (16-28),

[0190] Sp 11 、Sp 12 and Sp 13 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp 11 、Sp 12 and Sp 13 , at least one -CH2- may be substituted with -O-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, at least one hydrogen may be substituted with fluorine or chlorine, u is 0, 1 or 2, and g and h are each independently 0, 1, 2, 3 or 4.

[0191] Z 23 is a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Z 23 , at least one -CH2- may be substituted with -O-, -CO-, -COO- or -OCO-, at least one -(CH2)2- may be substituted with -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)- or -C(CH3)=C(CH3)-, and at least one hydrogen may be substituted with fluorine or chlorine.

[0192] P 11 、P 12 and P 13 are each independently a polymerizable group selected from the group consisting of the groups represented by formula (P-1) to formula (P-3);

[0193]

[0194] In formula (P-1) to formula (P-3),

[0195] M 11 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and in the M 11 , at least one hydrogen may be substituted with fluorine or chlorine, and at least one -CH2- may be substituted with -O-; M 12 and M 13 are each independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted with fluorine or chlorine.

[0196] The liquid crystal composition according to any one of items 9 to 15 according to item 16 further contains at least one of a polymerizable compound other than formula (1) according to item 1 and formula (16) according to item 14, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, and an antifoaming agent.

[0197] Item 17 A liquid crystal display element containing the liquid crystal composition according to any one of items 9 to 16.

[0198] The present invention also includes the following items. (a) The liquid crystal composition further contains at least two additives such as a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, and an antifoaming agent. (b) A polymerizable composition prepared by adding a polymerizable compound different from compound (1) or compound (16) to the liquid crystal composition. (c) A polymerizable composition prepared by adding compound (1) and compound (16) to the liquid crystal composition. (d) A liquid crystal complex prepared by polymerizing the polymerizable composition. (e) A polymer-stabilized alignment type element containing the liquid crystal complex. (f) A polymer-stabilized alignment type element made by using a polymerizable composition prepared by adding compound (1) and compound (16), and a polymerizable compound different from compound (1) or compound (16) to the liquid crystal composition.

[0199] The form of compound (1), the synthesis of compound (1), the liquid crystal composition, and the liquid crystal display element will be described in order.

[0200] 1. Form of Compound (1)

[0201] Compound (1) in an embodiment of the present invention is a polar compound having at least one structure represented by formula (A-1) or formula (A-2) and having a polymerizable group. Compound (1) exhibits the above effects by having a structure such as formula (A-1) or formula (A-2) in the molecule.

[0202]

[0203] One of the uses of compound (1) is an additive for a liquid crystal composition used in a liquid crystal display element. Compound (1) is added for the purpose of horizontally controlling the alignment of liquid crystal molecules. Regarding the preferred characteristics that such a compound should have, it is chemically stable under the conditions sealed in the element, has a high solubility in the liquid crystal composition, and has a large voltage holding ratio when used in a liquid crystal display element. Compound (1) satisfies such characteristics to a considerable extent.

[0204] Preferred examples of compound (1) will be described. R in compound (1) 1 , Z 1 to Z 5 , A 1 to A 4 , Sp 1 , Sp 2 , P 1 , P 2, preferred examples of a and b are also applicable to the lower formulae of compound (1). In compound (1), by appropriately combining the types of these groups, the properties can be adjusted arbitrarily. Since there are no significant differences in the properties of the compounds, compound (1) may also contain a greater amount of 2 H (deuterium), 13 carbon isotopes such as C.

[0205]

[0206] a and b are independently 0, 1, or 2, and the sum of a and b is 0, 1, 2, or 3;

[0207] Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, formula (A-1) or formula (A-2). In these rings, at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 , and at least one hydrogen in these groups may be substituted by fluorine or chlorine. Among them, at least one of Ring A 1 , Ring A 2 , Ring A 3 or Ring A 4 is a group represented by formula (A-1) or formula (A-2). In formula (A-1) and formula (A-2), Q 1 and Q 2 are independently -CH2-, -O-, -N(-R 8 )-, or -S-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms. In the said R 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine.

[0208]

[0209] When a is 2, the two rings A 1 may be different. When b is 2, the two rings A 4 may be different.

[0210] Preferred ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, perhydrocyclopentano[a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopentano[a]phenanthrene-3,17-diyl, the group represented by formula (A-1) or the group represented by formula (A-2). Preferred Q 1 and Q 2 are -CH2-, -O-, -N(-R 8 )-, or -S-. Further preferred Q 1 and Q 2 are -CH2- or -N(-R 8 )-. Here, R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms. In the R 8 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine. In these rings, at least one hydrogen may be substituted with fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, or an alkenyloxy group having 2 to 11 carbon atoms. In these groups, at least one hydrogen may be substituted with fluorine or chlorine. Further preferred are 1,4-cyclohexylene, 1,4-phenylene, perhydrocyclopentano[a]phenanthrene-3,17-diyl, or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopentano[a]phenanthrene-3,17-diyl. In these rings, at least one hydrogen may be substituted with fluorine or an alkyl group having 1 to 5 carbon atoms. Particularly preferred are 1,4-cyclohexylene, 1,4-phenylene, or perhydrocyclopentano[a]phenanthrene-3,17-diyl. In these rings, at least one hydrogen may be substituted with fluorine, methyl, or ethyl.

[0211] Z 1 , Z2 , Z 3 , Z 4 and Z 5 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in said Z 1 , Z 2 , Z 3 , Z 4 and Z 5 , at least one -CH2- may be substituted by -O-, -S-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine. Among them, Z 2 , Z 3 or Z 4 is at least one of -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -COO-, -OCO-, -CH=CH-, -CH=CHCO- or -COCH=CH-. When a is 2, the two Z 1 may be different. When b is 2, the two Z 5 may be different. Preferably, Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are independently a single bond, -(CH2)2-, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CF=CF-, -COS-, -SCO-, -CH=CHCOS-, -SCOCH=CH-, -CH=CHCO- or -COCH=CH-. Further preferably, they are a single bond, -(CH2)2-, -CH=CH-, -COO-, -OCO-, -CH=CHCO- or -COCH=CH-. Particularly preferably, they are a single bond, -COO- or -OCO-.

[0212] Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms. In said alkylene group, at least one -CH2- may be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and in these groups, at least one hydrogen may be substituted by fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 substituted.

[0213] Preferably, Sp 1 and Sp 2Independently a single bond, an alkylene group having 1 to 6 carbon atoms, or an alkylene group having 1 to 6 carbon atoms in which one -CH2- is replaced by -O-, or -OCOO-. Further preferably an alkylene group having 1 to 6 carbon atoms or -OCOO-.

[0214] P 1 and P 2 Independently is a group represented by any one of Formula (1b) to Formula (1h).

[0215] Preferred P 1 and P 2 Independently is a group represented by any one of Formula (1b), Formula (1c), Formula (1d) and Formula (1e).

[0216]

[0217] M 1 , M 2 , M 3 and M 4 Independently is hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is replaced by fluorine or chlorine. Preferred M 1 , M 2 , M 3 and M 4 Independently is hydrogen, fluorine, methyl, ethyl or trifluoromethyl. Further preferably hydrogen.

[0218] R 2 and R 6 Is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, in which at least one hydrogen may be replaced by fluorine or chlorine, and at least one -CH2- may be replaced by -O-.

[0219] Preferred R 2 and R 6 Is hydrogen, fluorine, methyl, ethyl, methoxymethyl or trifluoromethyl. Further preferably hydrogen.

[0220] R 3 , R 4 , R 5 and R 7 Independently is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 3 , R 4 , R 5 and R 7 At least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, but there is no case where R 5 and R 7 Is fluorine or chlorine.

[0221] Preferred R3 , R 4 , R 5 and R 7 are independently hydrogen, a linear alkyl group having 1 to 10 carbon atoms, a linear alkenyl group having 2 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms. Further preferably, they are hydrogen, a linear alkyl group having 2 to 6 carbon atoms, a linear alkenyl group having 2 to 6 carbon atoms, a linear alkoxy group having 1 to 5 carbon atoms, or a cyclic alkyl group having 4 to 6 carbon atoms.

[0222] X 1 is -N(-R 9 ), -O-, or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 9 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine.

[0223] Further preferred groups are the groups represented by formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2), or formula (1e-1).

[0224]

[0225] In formulas (1b) to (1h), M 1 and M 2 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine, and X 2 , X 3 , X 4 , X 5 and X 6 are independently -N(-R 9 ), -O-, or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 9 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine.

[0226] Preferred examples of compound (1) are formulas (1-1) to (1-3).

[0227]

[0228] In Formula (1-1) to Formula (1-3),

[0229] Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, a group represented by Formula (A-1) or Formula (A-2). At least one hydrogen in these Ring As 1 , Ring A 2 , Ring A 3 and Ring A 4 can be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 . At least one hydrogen in these alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, -Sp 1 -P 1 or -Sp 2 -P 2 can be substituted by fluorine or chlorine. Among them, at least one of Ring A 1 , Ring A 2 , Ring A 3 or Ring A 4 is of Formula (A-1) or Formula (A-2). Q 1 and Q 2 are independently -CH2-, -O-, -N(R 8 )-, or -S-. Here, R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms. Among the R 8 , at least one -CH2- can be substituted by -O- or -S-, at least one -(CH2)2- can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine;

[0230]

[0231] Z 2 , Z 3 and Z 4Independently a single bond, -(CH2)2-, -C≡C-, -C≡C-C≡C-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CF=CF-, -CH=CHCOO-, -OCOCH=CH-, -CH=CH-, -CH=CHCO-, -COCH=CH-, -COS-, -SCO-, -CH=CHCOS- or -SCOCH=CH-;

[0232] Sp 1 and Sp 2 Independently a single bond or an alkylene group having 1 to 10 carbon atoms, in which at least one -CH2- may be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- may be substituted by -CH=CH-, and in these groups, at least one hydrogen may be substituted by fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 substituted, and in the case where there are multiple Sp 1 or Sp 2 any two of them may be different;

[0233] P 1 and P 2 Independently a group represented by any one of Formula (1b) to Formula (1h), and in the case where there are multiple P 1 or P 2 any two of them may be different;

[0234]

[0235] In Formula (1b) to Formula (1h),

[0236] M 1 、M 2 、M 3 and M 4 Independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine; X 1 is -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the R 9 at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, but there is no case where R 9 is fluorine or chlorine;

[0237] R 2 and R6 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and said R 2 and R 6 among them, at least one hydrogen may be substituted by fluorine or chlorine, and at least one -CH2- may be substituted by -O-;

[0238] R 3 、R 4 、R 5 and R 7 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, and among said R 3 、R 4 、R 5 and R 7 among them, at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 5 and R 7 are fluorine or chlorine.

[0239] In the compound represented by formula (1-1), formula (1-2) or formula (1-3), any one of Z 2 、Z 3 or Z 4 is preferably -COO- or -OCO-.

[0240] Compound (1) is preferably a compound represented by the following formula.

[0241]

[0242]

[0243]

[0244]

[0245] In these formulas,

[0246] Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and among said Sp 1 and Sp 2 among them, at least one -CH2- may be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- may be substituted by -CH=CH-, and at least one hydrogen may be substituted by -Sp 1 -P 1 or -Sp 2 -P 2 substituted;

[0247] P 1 、P2 , Sp 1 and Sp 2 In the partial structures other than those, at least one hydrogen may be substituted with fluorine, chlorine, methyl or ethyl;

[0248] Q 1 is -CH2- or -N(-R 8 ), Q 2 is -N(-R 8 ), where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the R 8 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine.

[0249] P 1 and P 2 are independently a group represented by formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) or formula (1e-1);

[0250]

[0251] In formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) or formula (1e-1), X 2 , X 3 , X 4 , X 5 and X 6 are independently -N(-R 9 ), -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the R 9 , at least one -CH2- may be substituted with -O- or -S-, at least one -(CH2)2- may be substituted with -CH=CH- or -C≡C-, and at least one hydrogen may be substituted with fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine.

[0252] In addition, specific examples of compound (1) will be described in the examples below.

[0253] Formulas (2) to (15) show the component compounds of the liquid crystal composition. Compounds (2) to (4) have a small dielectric anisotropy. Compounds (5) to (7) have a large positive dielectric anisotropy. Compound (8) has an even larger positive dielectric anisotropy due to the presence of a cyano group. Compounds (9) to (16) have a large negative dielectric anisotropy. Specific examples of these compounds will be described below.

[0254] In compound (16), P 11 , P 12 and P 13 are each independently a polymerizable group.

[0255] Preferred P 11 , P 12 and P 13 are polymerizable groups selected from the group consisting of the groups represented by formulas (P-1) to (P-5). More preferably, P 11 , P 12 and P 13 are formula (P-1), formula (P-2) or formula (P-3). Particularly preferred formula (P-1) is -OCO-CH=CH2 or -OCO-C(CH3)=CH2. The wavy lines in formulas (P-1) to (P-5) indicate the bonding sites.

[0256]

[0257] In formulas (P-1) to (P-5), M 11 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, in which at least one hydrogen may be substituted with fluorine or chlorine, and at least one -CH2- may be substituted with -O-; M 11 and M 12 and M 13 are each independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted with fluorine or chlorine.

[0258] To improve the reactivity, preferred M 11 , M 12 and M 13 are hydrogen or methyl. More preferably, M 11 is methyl, and more preferably M 12 and M 13 are hydrogen.

[0259] Sp 11 , Sp 12 and Sp 13 are each independently a single bond or an alkylene group having 1 to 10 carbon atoms, and the Sp 11 , Sp 12 and Sp 13Among them, at least one -CH2- can be substituted by -O-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- can be substituted by -CH=CH- or -C≡C-, and at least one hydrogen can be substituted by fluorine or chlorine.

[0260] Preferred Sp 11 、Sp 12 and Sp 13 is a single bond.

[0261] Ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidin-2-yl or pyridin-2-yl. Among these rings, at least one hydrogen can be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine.

[0262] Preferred ring F and ring I are phenyl. Ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidin-2,5-diyl or pyridin-2,5-diyl. Among these rings, at least one hydrogen can be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine. Particularly preferred ring G is 1,4-phenylene or 2-fluoro-1,4-phenylene.

[0263] Z 22 and Z 23 are independently a single bond or an alkylene group having 1 to 10 carbon atoms. Among the alkylene groups, at least one -CH2- can be substituted by -O-, -CO-, -COO- or -OCO-, at least one -(CH2)2- can be substituted by -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)- or -C(CH3)=C(CH3)-, and at least one hydrogen in these groups can be substituted by fluorine or chlorine.

[0264] Preferred Z 7 and Z 8 are a single bond, -(CH2)2-, -CH2O-, -OCH2-, -COO- or -OCO-. Further preferred Z 22 and Z 23 is a single bond.

[0265] u is 0, 1 or 2.

[0266] Preferably, u is 0 or 1. f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or more. Preferably, f, g, or h is 1 or 2.

[0267] 2. Synthesis of Compound (1)

[0268] The synthesis method of compound (1) will be described. Compound (1) can be synthesized by appropriately combining methods of organic synthetic chemistry. Compounds for which the synthesis method is not described are synthesized by the methods described in books such as "Organic Syntheses" (John Wiley & Sons, Inc.), "Organic Reactions" (John Wiley & Sons, Inc.), "Comprehensive Organic Synthesis" (Pergamon Press), and "New Experimental Chemistry Course" (Maruzen).

[0269] 2-1. Linking Group Z 1 , linking group Z 2 , linking group Z 3 , linking group Z 4 and linking group Z 5 formation

[0270] Examples of methods for forming the linking group in compound (1) are as described in the following process. In the process, MSG 1 (or MSG 2 ) is a monovalent organic group having at least one ring. The monovalent organic groups represented by multiple MSG 1 (or MSG 2 ) may be the same or different. Compounds (1A) to (1L) correspond to compound (1) or an intermediate of compound (1).

[0271]

[0272]

[0273]

[0274] (I) Formation of a single bond

[0275] Compound (1A) is synthesized by reacting arylboronic acid (21) with compound (22) in the presence of a carbonate and tetrakis(triphenylphosphine)palladium catalyst. Compound (1A) can also be synthesized as follows: Compound (23) is reacted with n-butyllithium, then with zinc chloride, and then with compound (22) in the presence of dichlorobis(triphenylphosphine)palladium catalyst.

[0276] Generation of (II) -COO- and -OCO-

[0277] Compound (23) is reacted with n-butyllithium and then with carbon dioxide to obtain carboxylic acid (24). The carboxylic acid (24) is dehydrated with phenol (25) derived from compound (21) in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) to synthesize compound (1B) having -COO-. A compound having -OCO- is also synthesized by the same method.

[0278] Generation of (III) -CF2O- and -OCF2-

[0279] Compound (1B) is sulfided with Lawesson's reagent to obtain compound (26). Compound (26) is fluorinated with hydrogen fluoride pyridine complex and N-bromosuccinimide (NBS) to synthesize compound (1C) having -CF2O-. Refer to "Chem. Lett." 1992, No. 827 by M. Kuroboshi et al. Compound (1C) can also be synthesized by fluorinating compound (26) with (diethylamino)sulphurtrifluoride (DAST). Refer to "J. Org. Chem." 1990, Vol. 55, p. 768 by W.H. Bunnelle et al. A compound having -OCF2- is also synthesized by the same method.

[0280] Generation of (IV) -CH=CH-

[0281] The compound (22) is reacted with n-butyllithium and then with N,N-dimethylformamide (DMF) to obtain the aldehyde (27). The phosphonium salt (28) is reacted with potassium tert-butoxide to generate a phosphorus ylide, and the phosphorus ylide is reacted with the aldehyde (27) to synthesize the compound (1D). Since the cis-isomer is formed under the reaction conditions, the cis-isomer is isomerized to the trans-isomer using a known method as needed.

[0282] (V)-(CH2)2 formation

[0283] The compound (1D) is hydrogenated in the presence of a palladium-carbon catalyst to synthesize the compound (1E).

[0284] (VI)-C≡C formation

[0285] The compound (23) is reacted with 2-methyl-3-butyn-2-ol in the presence of a catalyst of dichloropalladium and copper iodide, and then deprotected under basic conditions to obtain the compound (29). The compound (29) is reacted with the compound (22) in the presence of a catalyst of dichlorobis(triphenylphosphine)palladium and copper halide to synthesize the compound (1F).

[0286] (VII)-CH2O- and -OCH2- formation

[0287] The compound (27) is reduced with sodium borohydride to obtain the compound (30). It is brominated with hydrobromic acid to obtain the compound (31). The compound (25) is reacted with the compound (31) in the presence of potassium carbonate to synthesize the compound (1G). Compounds having -OCH2- are also synthesized using the said method.

[0288] (VIII)-CF=CF- formation

[0289] The compound (23) is treated with n-butyllithium and then reacted with tetrafluoroethylene to obtain the compound (32). The compound (22) is treated with n-butyllithium and then reacted with the compound (32) to synthesize the compound (1H).

[0290] (IX)-CH=CHCO- and -COCH=CH- formation

[0291] The compound (1I) is synthesized by the aldol condensation reaction of the compound (40) and the compound (27) in the presence of NaOH.

[0292] (X)-CH=CHCOO- and -OCOCH=CH- formation

[0293] Compound (1J) was synthesized by dehydrating cinnamic acid (41) and compound (25) in the presence of 1,3 - dicyclohexylcarbodiimide (DCC) and 4 - dimethylaminopyridine (DMAP).

[0294] Generation of (X)-CH=CHCOS- and -SCOCH=CH-

[0295] Compound (1K) was synthesized by dehydrating cinnamic acid (41) and compound (26) in the presence of 1,3 - dicyclohexylcarbodiimide (DCC) and 4 - dimethylaminopyridine (DMAP).

[0296] Generation of (XI)-COS- and -SCO-

[0297] Compound (1L) was synthesized by dehydrating carboxylic acid (24) and compound (26) in the presence of 1,3 - dicyclohexylcarbodiimide (DCC) and 4 - dimethylaminopyridine (DMAP).

[0298] 2 - 2. Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 Generation

[0299] Regarding rings such as 1,4 - cyclohexylene, 1,4 - cyclohexenylene, 1,4 - phenylene, 2 - fluoro - 1,4 - phenylene, 2 - methyl - 1,4 - phenylene, 2 - ethyl - 1,4 - phenylene, naphthalene - 2,6 - diyl, decahydronaphthalene - 2,6 - diyl, 1,2,3,4 - tetrahydronaphthalene - 2,6 - diyl, tetrahydropyran - 2,5 - diyl, 1,3 - dioxane - 2,5 - diyl, pyrimidine - 2,5 - diyl, pyridine - 2,5 - diyl, perhydrocyclopenta[a]phenanthrene - 3,17 - diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17 - tetradehydrocyclopenta[a]phenanthrene - 3,17 - diyl, 9,10 - dihydrophenanthrene - 2,7 - diyl, 5,6 - dihydrophenanthridine - 3,8 - diyl, 6(5H) - phenanthridinone - 3,8 - diyl, etc., the starting materials are commercially available or the synthesis methods are well - known.

[0300] 2 - 3. Linking group Sp 1 or linking group Sp 2 and polymerizable group P 1 or polymerizable group P 2 Generation

[0301] Polymerizable group P 1 or polymerizable group P 2Preferred examples are acrylate (1b), maleimide (1c), itaconate (1d), vinyl ester (1e), formula (1f), oxiranyl (1g) or vinyloxy (1h).

[0302]

[0303] Synthesis of the polymerizable group bonded to the ring through the linking group Sp 1 or the linking group Sp 2 Examples of the method for synthesizing a compound in which is bonded to the ring are described below. First, the linking group Sp 1 or the linking group Sp 2 is shown as an example of a single bond.

[0304] (1) Synthesis of a compound having a single bond

[0305] Sp 1 or Sp 2 The synthesis method of a compound having a single bond is as described in the following process. In the process, MSG 1 is a monovalent organic group having at least one ring. Compounds (1S) to (1X) correspond to compound (1). When the polymerizable group is an acrylate or acrylamide derivative, it is synthesized by esterification or amidation of the corresponding acrylic acid with HO-MSG 1 or HNR 9 -MSG 1 . Vinyloxy is synthesized by etherification of HO-MSG 1 with vinyl bromide. Oxiranyl is synthesized by oxidation of the terminal double bond. Maleimide group is synthesized by reaction of an amino group with maleic anhydride. Itaconate is synthesized by esterification of the corresponding itaconic acid with HO-MSG 1 . Vinyl ester is synthesized by transesterification of vinyl acetate with HOOC-MSG 1 .

[0306]

[0307]

[0308] The synthesis method of a compound in which the linking group Sp 1 or the linking group Sp 2 is a single bond has been described above. Methods for generating other linking groups can be referred to the synthesis methods of the bonding group Z 1 , the bonding group Z 2 , the bonding group Z 3 , the bonding group Z 4 and the bonding group Z 5 to synthesize.

[0309] 2-4. Synthesis examples

[0310] Examples of the method for synthesizing compound (1) are described below. Among these compounds, MES is a mesogenic group having at least one ring. P 1 , M 1 , M 2 , Sp 1 and Sp 2 are defined as the same as described above.

[0311] Compound (51A) and compound (51B) are commercially available or can be synthesized by using a mesogenic group (MES) having an appropriate ring structure as a starting material and according to a usual organic synthesis method.

[0312] In the case of synthesizing a compound in which MES and Sp 1 are linked by an ether bond, by using compound (51A) as a starting material and using a base such as compound (52) and potassium hydroxide for etherification, compound (53A) can be obtained. In addition, in the case of synthesizing a compound in which MES and Sp 1 are linked by a single bond, by using compound (51B) as a starting material and using a metal catalyst such as compound (52), palladium and a base for a cross-coupling reaction, compound (53B) can be obtained. Compound (53A) or compound (53B) is sometimes derivatized into compound (54A) or compound (54B) in which a protecting group such as trimethylsilyl (TMS) and tetrahydropyranyl (THP) functions as needed.

[0313] Thereafter, by using compound (53A), compound (53B), compound (54A) or compound (54B) and carrying out etherification again in the presence of a base such as compound (55) and potassium hydroxide, compound (57A) or compound (57B) can be obtained.

[0314] At this time, in the case where the protecting group functions in the previous stage, the protecting group is removed by a deprotection reaction.

[0315]

[0316] P 2 For example, compound (1) which is a group represented by formula (1b-3) can be synthesized from compound (57) by the following method. By using compound (57) and carrying out an esterification reaction in the presence of compound (58), DCC and DMAP, it can be derivatized into compound (1Y).

[0317]

[0318] 3. Liquid crystal composition

[0319] The liquid crystal composition of an embodiment of the present invention contains compound (1) as component A. Compound (1) can contribute to the control of the alignment of liquid crystal molecules through non-covalent bonding interactions with the substrate of the element. The composition preferably contains compound (1) as component A and also contains liquid crystalline compounds selected from component B, component C, component D, and component E shown below. Component B is compounds (2) to (4). Component C is compounds (5) to (7). Component D is compound (8). Component E is compounds (9) to (16). The composition may also contain other liquid crystalline compounds different from compounds (2) to (16). When preparing the composition, it is preferable to select component B, component C, component D, and component E in consideration of the magnitude of positive or negative dielectric anisotropy, etc. The composition with appropriately selected components has a high upper limit temperature, a low lower limit temperature, a small viscosity, an appropriate optical anisotropy (i.e., a large optical anisotropy or a small optical anisotropy), a large positive or negative dielectric anisotropy, a large specific resistance, stability to heat or ultraviolet rays, and an appropriate elastic constant (i.e., a large elastic constant or a small elastic constant).

[0320] In order to maintain high stability to ultraviolet rays, the preferred proportion of compound (1) is usually about 0.01% by weight or more based on the weight of the liquid crystal composition. In order to dissolve in the liquid crystal composition, the preferred proportion of compound (1) is usually about 10% by weight or less. A more preferred proportion is in the range of about 0.1% by weight to about 5% by weight based on the weight of the liquid crystal composition. The most preferred proportion is in the range of about 0.5% by weight to about 3% by weight based on the weight of the liquid crystal composition.

[0321] Component B is a compound having alkyl groups or the like at both terminal groups. Preferred examples of component B include: compounds (2-1) to (2-11), compounds (3-1) to (3-19), and compounds (4-1) to (4-7). In the compounds of component B, R 11 and R 12 are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. In the alkyl group or alkenyl group, at least one -CH2- may be substituted by -O-, and at least one hydrogen may be substituted by fluorine.

[0322]

[0323] Since component B has a small absolute value of dielectric anisotropy, it is a compound close to neutral. Compound (2) is mainly effective in reducing viscosity or adjusting optical anisotropy. Compounds (3) and (4) have the effect of expanding the temperature range of the nematic phase by increasing the upper limit temperature or are effective in adjusting optical anisotropy.

[0324] As the content of Component B increases, the dielectric anisotropy of the composition decreases, but the viscosity decreases. Therefore, as long as the required value of the threshold voltage of the element is satisfied, a higher content is preferable. When preparing a composition for IPS, VA, or other modes, based on the weight of the liquid crystal composition, the content of Component B is preferably 30% by weight or more, and more preferably 40% by weight or more.

[0325] Component C is a compound (5) to compound (7) having fluorine, chlorine, or a fluorine-containing group at the right end. Preferred examples of Component C include: compound (5-1) to compound (5-16), compound (6-1) to compound (6-120), and compound (7-1) to compound (7-62). In the compounds of Component C, R 13 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. In the alkyl and alkenyl groups, at least one -CH2- may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; X 11 is fluorine, chlorine, -OCF3, -OCHF2, -CF3, -CHF2, -CH2F, -OCF2CHF2, or -OCF2CHFCF3.

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333] Since Component C has a positive dielectric anisotropy and very excellent stability against heat, light, etc., it is used in the case of preparing a composition for IPS, FFS, OCB, or other modes. Based on the weight of the liquid crystal composition, the suitable content of Component C is in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, and more preferably in the range of 40% by weight to 95% by weight. When Component C is added to a composition having a negative dielectric anisotropy, based on the weight of the liquid crystal composition, the content of Component C is preferably 30% by weight or less. By adding Component C, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

[0334] Component D is a compound (8) having a right terminal group of -C≡N or -C≡C-C≡N. Preferred examples of Component D include compounds (8-1) to compounds (8-64). Among the compounds of Component D, R 14 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. In the alkyl group and the alkenyl group, at least one -CH2- may be substituted with -O-, and at least one hydrogen may be substituted with fluorine; X 12 is -C≡N or -C≡C-C≡N.

[0335]

[0336]

[0337] Since Component D has a positive dielectric anisotropy and a large value thereof, it is mainly used for preparing compositions for TN and other modes. By adding the said Component D, the dielectric anisotropy of the composition can be increased. Component D brings about the effects of expanding the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. Component D is also useful for adjusting the voltage-transmittance curve of the element.

[0338] In the case of preparing a composition for TN and other modes, based on the weight of the liquid crystal composition, the content of Component D is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, and more preferably in the range of 40% by weight to 95% by weight. In the case of adding Component D to a composition having a negative dielectric anisotropy, based on the weight of the liquid crystal composition, the content of Component D is preferably 30% by weight or less. By adding Component D, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

[0339] Component E is compounds (9) to compounds (16). These compounds have a phenylene group in which the lateral position is substituted with two fluorines or chlorines, such as 2,3-difluoro-1,4-phenylene.

[0340] Preferred examples of Component E include: compounds (9-1) to compounds (9-8), compounds (10-1) to compounds (10-17), compound (11-1), compounds (12-1) to compounds (12-3), compounds (13-1) to compounds (13-11), compounds (14-1) to compounds (14-3), compounds (15-1) to compounds (15-3), and compounds (16-1) to compounds (16-3). Among the compounds of Component E, R 15 and R 16 are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. In the alkyl group and the alkenyl group, at least one -CH2- may be substituted with -O-, and at least one hydrogen may be substituted with fluorine; R17 is hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a fluoroalkyl group having 1 to 10 carbon atoms, 1 to 10 fluorine atoms and 1 to 10 carbon atoms, in the alkyl group and the alkenyl group, at least one —CH2— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine.

[0341]

[0342]

[0343] The dielectric anisotropy of Component E is negative and large. In the case where Component E is used to prepare a composition for IPS, VA, PSA or other modes. As the content of Component E increases, the dielectric anisotropy of the composition is negative and increases, but the viscosity increases. Therefore, as long as the required value of the threshold voltage of the device is satisfied, the content is preferably small. When considering that the dielectric anisotropy is about -5, in order to perform sufficient voltage driving, based on the weight of the liquid crystal composition, the content of Component E is preferably 40% by weight or more.

[0344] In Component E, Compound (9) is a bicyclic compound, so it is mainly effective in reducing viscosity, adjusting optical anisotropy or increasing dielectric anisotropy. Compounds (10) and (11) are tricyclic compounds, so they have the effects of increasing the upper limit temperature, increasing optical anisotropy or increasing dielectric anisotropy. Compounds (12) to (16) have the effect of increasing dielectric anisotropy.

[0345] Component F is Compound (DB-1) and Compound (DB-2). These compounds have a dibenzothiophene structure in which two lateral positions are substituted with fluorine or chlorine, such as 1,8-difluoro-2,7-dibenzothiophene, a 1,8-difluoro-2,7-dibenzofuran structure, etc. Preferred examples of Component F include Compounds (DB-1-1) to (DB-1-14) and Compounds (DB-2-1) to (DB-2-9). Further preferred examples of Component F include Compounds (DB-1-1) to (DB-1-14).

[0346] In the compounds of Component F, R 100 is independently hydrogen, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, in the R 100 at least one —CH2— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine, R 200 is independently a straight-chain alkyl group having 1 to 10 carbon atoms, a branched-chain alkyl group having 3 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, in the R 200 at least one —CH2— may be replaced by —O— or —S—, and at least one hydrogen may be replaced by fluorine.

[0347]

[0348]

[0349]

[0350] The dielectric anisotropy of Component E and Component F is negative and large. Component E and Component F can be used in the case of preparing compositions for IPS, FFS, VA, PSA and other modes. As the total content of Component E and Component F increases, the dielectric anisotropy of the composition is negative and increases, but the viscosity increases. Therefore, as long as the required value of the threshold voltage of the element is satisfied, the content is preferably small. When considering that the dielectric anisotropy is about -5, in order to perform sufficient voltage driving, based on the weight of the liquid crystal composition, the total content of Component E and Component F is preferably 40% by weight or more.

[0351] Component F has a condensed ring structure such as dibenzothiophene, dibenzofuran, and dibenzofluorene. It mainly has the effects of increasing the upper limit temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. In addition, since it has a condensed ring structure and may also have a heteroatom, it is considered to have a tendency to have a higher polarity than other liquid crystalline compounds, and thus it is inferred that the compatibility with the monomer forming the alignment control layer is relatively high. Based on the weight of the liquid crystal composition, the preferred content of Component F is in the range of 1% by weight to 20% by weight. Based on the weight of the liquid crystal composition, the more preferred content of Component F is in the range of 3% by weight to 20% by weight. Further preferably, the content of Component F is in the range of 3% by weight to 15% by weight.

[0352] In Component E, Compound (9) is a bicyclic compound, so it mainly has effects in reducing viscosity, adjusting optical anisotropy, or increasing dielectric anisotropy. Compounds (10) and (11) are tricyclic compounds, so they have the effects of increasing the upper limit temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. Compounds (12) to (15) have the effect of increasing dielectric anisotropy.

[0353] In the case of preparing compositions for IPS, VA, PSA and other modes, based on the weight of the liquid crystal composition, the total content of Component E and Component F is preferably 40% by weight or more, and more preferably in the range of 50% by weight to 95% by weight. In the case of adding Component E and Component F to a composition with positive dielectric anisotropy, based on the weight of the liquid crystal composition, the total content of Component E and Component F is preferably 30% by weight or less. By adding Component E and Component F, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

[0354] By appropriately combining the above-described Component B, Component C, Component D, and Component E, a liquid crystal composition can be prepared that satisfies at least one of the characteristics of a high upper limit temperature, a low lower limit temperature, a small viscosity, an appropriate optical anisotropy, a large positive or negative dielectric anisotropy, a large specific resistance, a high stability to ultraviolet rays, a high stability to heat, a large elastic constant, etc. If necessary, a liquid crystalline compound different from Component B, Component C, Component D, and Component E may also be added.

[0355] The liquid crystal composition can be prepared by known methods. For example, the component compounds are mixed and then dissolved in each other by heating. Additives can also be added to the composition according to the use. Examples of additives are polymerizable compounds other than those of formula (1) and formula (16), polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, defoaming agents, etc. Such additives are well known to those of ordinary skill in the art and are described in the literature.

[0356] The polymerizable compound is added for the purpose of generating a polymer in the liquid crystal composition. Ultraviolet rays are irradiated in a state where a voltage is applied between the counter electrodes, and the polymerizable compound and Compound (1) are copolymerized, thereby generating a polymer in the liquid crystal composition. At this time, Compound (1) is fixed in a state of interacting with the surface of the glass (or metal oxide) substrate by non-covalent bonding in the polar group. Thereby, the ability to control the orientation of the liquid crystal molecules is further improved, and at the same time, Compound (1) does not leak into the liquid crystal composition. In addition, an appropriate pretilt can also be obtained on the surface of the glass (or metal oxide) substrate, so that a liquid crystal display element with a shortened response time and a large voltage holding ratio can be obtained.

[0357] Preferred examples of the polymerizable compound are acrylate, methacrylate, vinyl compound, vinyloxy compound, allyl ether, epoxy compound (oxirane, oxetane), and vinyl ketone. Further preferred examples are compounds having at least one acryloyloxy group and compounds having at least one methacryloyloxy group. Further preferred examples also include compounds having both acryloyloxy and methacryloyloxy groups.

[0358] Further preferred examples of the polymerizable compound are Compound (M-1) to Compound (M-17). In Compound (M-1) to Compound (M-17), R 25 to R 31 are independently hydrogen or methyl; s, v, and x are independently 0 or 1; t and u are independently integers from 1 to 10; L 21 to L 26 are independently hydrogen or fluorine, and L 27 and L 28 are independently hydrogen, fluorine, or methyl.

[0359]

[0360] Polymerizable compounds can be rapidly polymerized by adding a polymerization initiator. By optimizing the reaction temperature, the amount of residual polymerizable compounds can be reduced. Examples of photo radical polymerization initiators are TPO, 1173, and 4265 in the Darocure series of BASF; 184, 369, 500, 651, 784, 819, 907, 1300, 1700, 1800, 1850, and 2959 in the Irgacure series.

[0361] Additional examples of photo radical polymerization initiators are 4-methoxyphenyl-2,4-bis(trichloromethyl)-s-triazine, 2-(4-butoxystyryl)-5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-benzophenazine, benzophenone / michler's ketone mixture, hexaarylbiimidazole / mercaptobenzimidazole mixture, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, benzyl dimethyl ketal, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2,4-diethylxanthone / methyl 4-dimethylaminobenzoate mixture, benzophenone / methyltriethanolamine mixture.

[0362] By adding a photo radical polymerization initiator to the liquid crystal composition and then irradiating ultraviolet light in a state where an electric field is applied, polymerization can be carried out. However, unreacted polymerization initiators or decomposition products of the polymerization initiator may cause display defects such as image burn-in in the device. To prevent such a situation, photo polymerization can also be carried out without adding a polymerization initiator. The preferred wavelength range of the irradiated light is from 150 nm to 500 nm. A more preferred wavelength range is from 250 nm to 450 nm, and the most preferred wavelength range is from 300 nm to 400 nm.

[0363] When a compound (1) having an ester (-COO-, -OCO-) as a bonding group is mixed into the composition, the main effects brought by the compound (1) as component A to the properties of the composition are as follows. When the compound (1) undergoes Fries rearrangement or photodimerization by polarization, it aligns in a certain direction at the molecular level. Therefore, a thin film prepared from a polar compound aligns liquid crystal molecules in the same way as an alignment film such as polyimide.

[0364] In the case of a compound (1) having an aromatic ester and a polymerizable group, the aromatic ester moiety undergoes photodecomposition by irradiating ultraviolet light, thereby forming radicals and causing a photo Fries rearrangement.

[0365] In the photo-Fries rearrangement, photolysis of the aromatic ester moiety occurs when the polarization direction of polarized ultraviolet light is the same as the major axis direction of the aromatic ester moiety. After photolysis, re-bonding takes place and a hydroxyl group is generated within the molecule through tautomerization. It is considered that the interaction at the substrate interface is generated by the hydroxyl group, and the polar compound has anisotropy and is likely to be adsorbed on the substrate interface side. In addition, since it has a polymerizable group, the compound (1) that reacts by polymerization in the direction of polarization does not lose its directionality and is fixed. The above properties can be utilized to prepare a film capable of aligning liquid crystal molecules. For preparing the film, the ultraviolet light to be irradiated is preferably linearly polarized light. First, the compound (1) as a polar compound is added to the liquid crystal composition in the range of 0.1 wt% to 10 wt%, and the composition is heated to dissolve the polar compound. The composition is injected into a cell without an alignment film. Subsequently, while heating the cell, linearly polarized light is irradiated, whereby the polar compound undergoes photo-Fries rearrangement and polymerization.

[0366] The polar compound subjected to photo-Fries rearrangement is aligned in a certain direction, and the film formed after polymerization has the function of a liquid crystal alignment film.

[0367] When storing the polymerizable compound, a polymerization inhibitor may be added to prevent polymerization. The polymerizable compound is usually added to the composition without removing the polymerization inhibitor. Examples of the polymerization inhibitor are hydroquinone derivatives such as hydroquinone and methyl hydroquinone, 4-tert-butylcatechol, 4-methoxyphenol, phenothiazine, etc.

[0368] The optically active compound brings the effect of preventing reverse twist by inducing a helical structure in the liquid crystal molecules to give the required twist angle. By adding the optically active compound, the helical pitch can be adjusted. For the purpose of adjusting the temperature dependence of the helical pitch, two or more optically active compounds may also be added. Preferred examples of the optically active compound include the following compound (Op-1) to compound (Op-18). In compound (Op-18), ring J is 1,4-cyclohexylene or 1,4-phenylene, and R 28 is an alkyl group having 1 to 10 carbon atoms.

[0369]

[0370] To maintain a large voltage retention rate, antioxidants are effective. Preferred examples of antioxidants include the following compounds (AO-1) and compound (AO-2); Irganox 415, Irganox 565, Irganox 1010, Irganox 1035, Irganox 3114, and Irganox 1098 (trade names: BASF Corporation). To prevent a decrease in the upper limit temperature, ultraviolet absorbers are effective. Preferred examples of ultraviolet absorbers are benzophenone derivatives, benzoate derivatives, triazole derivatives, etc. As specific examples, the following compounds (AO-3) and compound (AO-4) can be cited; Tinuvin 329, Tinuvin P, Tinuvin 326, Tinuvin 234, Tinuvin 213, Tinuvin 400, Tinuvin 328, and Tinuvin 99-2 (trade names: BASF Corporation); and 1,4-diazabicyclo[2.2.2]octane (1,4-Diazabicyclo[2.2.2]octane, DABCO).

[0371] To maintain a large voltage retention rate, light stabilizers such as sterically hindered amines are preferred. Preferred examples of light stabilizers include the following compounds (AO-5) and compound (AO-6); Tinuvin 144, Tinuvin 765, and Tinuvin 770DF (trade names: BASF Corporation). To maintain a large voltage retention rate, heat stabilizers are also effective. Preferred examples include Irgafos 168 (trade name: BASF Corporation). To prevent foaming, antifoaming agents are effective. Preferred examples of antifoaming agents are dimethyl silicone oil, methylphenyl silicone oil, etc.

[0372]

[0373] In compound (AO-1), R 40 is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, -COOR 41 or -CH2CH2COOR 41 , where R 41 is an alkyl group having 1 to 20 carbon atoms. In compound (AO-2) and compound (AO-5), R 42 is an alkyl group having 1 to 20 carbon atoms. In compound (AO-5), R 43 is hydrogen, methyl, or O· (Oxygen free radicals), ring G is 1,4-cyclohexylene or 1,4-phenylene, and z is 1, 2 or 3.

[0374] 4. Liquid crystal display element

[0375] The liquid crystal composition can be used in liquid crystal display elements that operate in modes such as PC, TN, STN, OCB, PSA, etc. and are driven in an active matrix manner. The composition can also be used in liquid crystal display elements that operate in modes such as PC, TN, STN, OCB, VA, IPS, etc. and are driven in a passive matrix manner. These elements can also be applied to any type of reflective, transmissive, or transflective type.

[0376] The composition can also be used in nematic curvilinear aligned phase (NCAP) elements made by microencapsulating nematic liquid crystals, polymer dispersed liquid crystal display (PDLCD) elements made by forming three-dimensional network polymers in liquid crystals, and polymer network liquid crystal display (PNLCD) elements. When the addition amount of the polymerizable compound is about 10% by weight or less based on the weight of the liquid crystal composition, a liquid crystal display element in PSA mode can be fabricated. Based on the weight of the liquid crystal composition, the preferred proportion of the polymerizable compound is in the range of about 0.1% by weight to about 2% by weight. Further preferably, the proportion is in the range of about 0.2% by weight to about 1.0% by weight based on the weight of the liquid crystal composition. The elements in PSA mode can be driven by driving methods such as active matrix and passive matrix. Such elements can also be applied to any type of reflective, transmissive, or transflective type. By increasing the addition amount of the polymerizable compound, polymer dispersed mode elements can also be fabricated.

[0377] In polymer-stabilized alignment type elements, the polymer contained in the composition aligns liquid crystal molecules. The compound (1) as a polar compound helps to align liquid crystal molecules. That is, the compound (1) can be used in place of the alignment film. An example of the method for manufacturing such elements is described below.

[0378] Prepare an element having two substrates called an array substrate and a color filter substrate. The substrates do not have an alignment film. At least one of the substrates has an electrode layer. Mix liquid crystalline compounds to prepare a liquid crystal composition. Add a polymerizable compound and compound (1) as a polar compound to the composition. Additives may also be added as needed. Inject the composition into the element. Irradiate the element with light. Preferably ultraviolet light. Polymerize the polymerizable compound by light irradiation. By this polymerization, a composition containing a polymer is generated, and thus an element having a PSA mode can be fabricated.

[0379] Describe a method for manufacturing an element. The first step is to add compound (1) as a polar compound to the liquid crystal composition and heat the composition at a temperature higher than the upper limit temperature to dissolve it. The second step is to inject the composition into a liquid crystal display element. The third step is to irradiate polarized ultraviolet light while heating the liquid crystal composition to a temperature higher than the upper limit temperature. Compound (1) as a polar compound undergoes a photo Fries rearrangement or photodimerization by linearly polarized light and also polymerizes. The polymer of compound (1) forms a film on the substrate and is fixed. The polymer is aligned in a certain direction at the molecular level, so the film has the function of a liquid crystal alignment film. A liquid crystal display element without an alignment film such as polyimide can be manufactured by this method.

[0380] In the procedure, compound (1) as a polar compound is biased to exist on the substrate due to the interaction between the polar group and the substrate surface. The compound (1) orients liquid crystal molecules by irradiation with polarized ultraviolet light, and at the same time the polymerizable compound polymerizes by ultraviolet light, so a polymer that maintains the orientation is generated. Due to the effect of the polymer, the orientation of liquid crystal molecules is additionally stabilized, so the response time of the element is shortened. Image burn-in is due to poor operation of liquid crystal molecules, so it is also improved by the effect of the polymer. In particular, compound (1) in the embodiment of the present invention is a polymerizable polar compound, so it orients liquid crystal molecules and copolymerizes with other polymerizable compounds. Thus, the polar compound does not leak into the liquid crystal composition, and a liquid crystal display element with a large voltage holding ratio can be obtained.

[0381] [Examples]

[0382] The present invention will be further described in detail by examples (including synthesis examples and usage examples of elements). The present invention is not limited by these examples. The present invention includes a mixture of the composition of usage example 1 and the composition of usage example 2. The present invention also includes mixtures prepared by mixing at least two of the compositions of the usage examples.

[0383] 1. Examples of compound (1)

[0384] Compound (1) was synthesized by the procedures shown in Example 1 and the like. Unless otherwise specified, the reaction was carried out under a nitrogen atmosphere. The synthesized compound was identified by methods such as Nuclear Magnetic Resonance (NMR) analysis. The properties of compound (1), the liquid crystalline compound, the composition, and the device were measured by the following methods.

[0385] NMR analysis: When measuring, a DRX-500 manufactured by Bruker BioSpin was used. 1 In the measurement of 1H-NMR, the sample was dissolved in a deuterated solvent such as CDCl3, and the measurement was carried out at room temperature under the conditions of 500 MHz and 16 cumulative times. Tetramethylsilane was used as an internal standard. 19 In the measurement of 19F-NMR, CFCl3 was used as an internal standard, and the measurement was carried out with 24 cumulative times. In the description of the nuclear magnetic resonance spectrum, s means singlet, d means doublet, t means triplet, q means quartet, quin means quintet, sex means sextet, m means multiplet, and br means broad peak.

[0386] Gas chromatography analysis: When measuring, a GC-2010 type gas chromatograph manufactured by Shimadzu Corporation was used. The column used was a capillary column DB-1 (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc. Helium (1 ml / min) was used as the carrier gas. The temperature of the sample vaporization chamber was set to 300 °C, and the temperature of the detector (flame ionization detector (FID)) part was set to 300 °C. The sample was dissolved in acetone and prepared as a 1 wt% solution, and 1 μl of the obtained solution was injected into the sample vaporization chamber. The recorder used was a GC Solution system etc. manufactured by Shimadzu Corporation.

[0387] High Performance Liquid Chromatography (HPLC) analysis: During the determination, Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation was used. The column used was YMC-Pack ODS-A (length 150 mm, inner diameter 4.6 mm, particle size 5 μm) manufactured by YMC. The eluent was prepared by appropriately mixing acetonitrile and water. As the detector, an Ultraviolet (UV) detector, a Reflective Index (RI) detector, a CORONA detector, etc. were appropriately used. When using the UV detector, the detection wavelength was set to 254 nm. The sample was dissolved in acetonitrile and prepared as a 0.1 wt% solution, and 1 μL of the solution was introduced into the sample chamber. As the recorder, C-R7A plus manufactured by Shimadzu Corporation was used.

[0388] Ultraviolet-visible spectroscopic analysis: During the determination, PharmaSpec UV-1700 manufactured by Shimadzu Corporation was used. The detection wavelength was set to 190 nm to 700 nm. The sample was dissolved in acetonitrile and prepared as a 0.01 mmol / L solution, and placed in a quartz cell (optical path length 1 cm) for determination.

[0389] Sample for determination: When determining the phase structure and transition temperature (clear point, melting point, polymerization initiation temperature, etc.), the compound itself was used as the sample.

[0390] Determination method: The determination of the properties was carried out by the following methods. Most of these methods are the methods described in the JEITA standard (JEITA·ED-2521B) deliberated and formulated by the Japan Electronics and Information Technology Industries Association (JEITA), or the methods modified therefrom. In the TN element used for determination, no thin film transistor (TFT) was installed.

[0391] (1) Phase structure

[0392] The sample was placed on the heating plate (FP-52 type hot stage of Mettler company) of a melting point determination device including a polarizing microscope. The phase state and its changes of the sample were observed using the polarizing microscope while heating the sample at a rate of 3 °C / min, and the type of phase was determined.

[0393] (2) Transition temperature (°C)

[0394] When measuring, a scanning calorimeter manufactured by Perkin Elmer, a Diamond Differential Scanning Calorimeter (DSC) system, or a high-sensitivity differential scanning calorimeter X-DSC7000 manufactured by SSI Nanotechnology is used. The temperature of the sample is raised and lowered at a rate of 3 °C / min, and the starting point of the endothermic peak or exothermic peak accompanying the phase change of the sample is obtained by extrapolation to determine the transition temperature. The melting point and polymerization starting temperature of the compound are also measured using the said apparatus. Sometimes the temperature at which a compound changes from a solid to a smectic phase, a nematic phase or other liquid crystal phases is simply referred to as the "lower limit temperature of the liquid crystal phase". Sometimes the temperature at which a compound changes from a liquid crystal phase to a liquid is simply referred to as the "clear point".

[0395] Crystals are represented as C. When differentiating the types of crystals, they are represented as C1, C2, etc. respectively. The smectic phase is represented as S, and the nematic phase is represented as N. In the smectic phase, when differentiating the smectic A phase, smectic B phase, smectic C phase or smectic F phase, they are represented as S A 、S B 、S C or S F respectively. Liquids (isotropic) are represented as I. The transition temperature is expressed, for example, as "C 50.0 N 100.0 I". It means that the temperature at which the crystal changes to the nematic phase is 50.0 °C, and the temperature at which the nematic phase changes to the liquid is 100.0 °C.

[0396] (3) Upper limit temperature of the nematic phase (T NI or NI; °C)

[0397] The sample is placed on the heating plate of a melting point measuring device including a polarizing microscope and heated at a rate of 1 °C / min. The temperature at which a part of the sample changes from the nematic phase to an isotropic liquid is measured. Sometimes the upper limit temperature of the nematic phase is simply referred to as the "upper limit temperature". When the sample is a mixture of compound (1) and a host liquid crystal, it is represented by the notation T NI . When the sample is a mixture of compound (1) and compounds such as component B, component C, component D, etc., it is represented by the notation NI.

[0398] (4) Lower limit temperature of the nematic phase (T C ; °C)

[0399] A sample with a nematic phase was stored in a freezer at 0 °C, -10 °C, -20 °C, -30 °C, and -40 °C for 10 days, and then the liquid crystal phase was observed. For example, when the sample maintained the nematic phase at -20 °C and changed to a crystalline or smectic phase at -30 °C, T C is recorded as ≤ -20 °C. Sometimes the lower limit temperature of the nematic phase is simply referred to as the "lower limit temperature".

[0400] (5) Viscosity (bulk viscosity; η; measured at 20 °C; mPa·s)

[0401] During the measurement, an E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd. was used.

[0402] (6) Optical anisotropy (refractive index anisotropy; measured at 25 °C; Δn)

[0403] Using light with a wavelength of 589 nm, the measurement was carried out with an Abbe refractometer equipped with a polarizing plate on the eyepiece. After rubbing the surface of the main prism in one direction, the sample was dropped onto the main prism. The refractive index (n∥) was measured when the direction of polarization was parallel to the direction of rubbing. The refractive index (n⊥) was measured when the direction of polarization was perpendicular to the direction of rubbing. The value of the optical anisotropy (Δn) was calculated from the formula Δn = n∥ - n⊥.

[0404] (7) Specific resistance (ρ; measured at 25 °C; Ωcm)

[0405] 1.0 mL of the sample was injected into a container including electrodes. A DC voltage (10 V) was applied to the container, and the DC current after 10 seconds was measured. The specific resistance was calculated from the following formula. (Specific resistance) = {(voltage) × (capacitance of the container)} / {(DC current) × (dielectric constant of vacuum)}.

[0406] For samples with positive dielectric anisotropy and samples with negative dielectric anisotropy, sometimes the measurement methods of the properties are different. The measurement methods for positive dielectric anisotropy are described in items (8a) to (12a). In the case of negative dielectric anisotropy, they are described in items (8b) to (12b).

[0407] (8a) Viscosity (rotational viscosity; γ1; measured at 25 °C; mPa·s)

[0408] Positive dielectric anisotropy: The measurement is based on the method described in "Molecular Crystals and Liquid Crystals" (Vol. 259, 37 (1995)) by M. Imai et al. A sample is placed in a TN element with a twist angle of 0 degrees and a gap (cell gap) of 5 μm between two glass substrates. The voltage is applied to the element stepwise in units of 0.5 V in the range of 16 V to 19.5 V. After 0.2 seconds without applying voltage, the voltage is applied repeatedly under the conditions of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of the transient current generated by the application are measured. The value of the rotational viscosity is obtained from these measured values and the calculation formula (8) on page 40 of the paper by M. Imai et al. The value of the dielectric anisotropy required for the calculation is obtained using the element for which the rotational viscosity has been measured and the method described below.

[0409] (8b) Viscosity (rotational viscosity; γ1; measured at 25 °C; mPa·s)

[0410] Negative dielectric anisotropy: The measurement is based on the method described in "Molecular Crystals and Liquid Crystals" (Vol. 259, 37 (1995)) by M. Imai et al. A sample is placed in a VA element with a gap (cell gap) of 20 μm between two glass substrates. The voltage is applied to the element stepwise in units of 1 V in the range of 39 V to 50 V. After 0.2 seconds without applying voltage, the voltage is applied repeatedly under the conditions of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current and peak time of the transient current generated by the application are measured. The value of the rotational viscosity is obtained from these measured values and the calculation formula (8) on page 40 of the paper by M. Imai et al. The dielectric anisotropy required for the calculation is the value measured in the following item of dielectric anisotropy.

[0411] (9a) Dielectric anisotropy (Δε; measured at 25 °C)

[0412] Positive dielectric anisotropy: A sample is placed in a TN element with a cell gap (spacing between two glass substrates) of 9 μm and a twist angle of 80 degrees. A sine wave (10 V, 1 kHz) is applied to the element, and after 2 seconds, the dielectric constant (ε∥) in the long axis direction of the liquid crystal molecules is measured. A sine wave (0.5 V, 1 kHz) is applied to the element, and after 2 seconds, the dielectric constant (ε⊥) in the short axis direction of the liquid crystal molecules is measured. The value of the dielectric anisotropy is calculated by the formula Δε = ε∥ - ε⊥.

[0413] (9b) Dielectric anisotropy (Δε; measured at 25 °C)

[0414] Negative dielectric anisotropy: The value of the dielectric anisotropy is calculated by the formula Δε = ε∥ - ε⊥. The dielectric constants (ε∥ and ε⊥) are measured as follows.

[0415] 1) Measurement of dielectric constant (ε∥): A solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) is coated on a glass substrate that has been thoroughly cleaned. After the glass substrate is rotated using a spinner, it is heated at 150 °C for 1 hour. A sample is placed in a VA element with a cell gap (spacing between two glass substrates) of 4 μm, and the element is sealed with an adhesive that is cured using ultraviolet light. A sine wave (0.5 V, 1 kHz) is applied to the element, and after 2 seconds, the dielectric constant (ε∥) in the long axis direction of the liquid crystal molecules is measured.

[0416] 2) Measurement of dielectric constant (ε⊥): A polyimide solution is coated on a glass substrate that has been thoroughly cleaned. After the glass substrate is calcined, the obtained alignment film is subjected to a rubbing treatment. A sample is placed in a TN element with a cell gap (spacing between two glass substrates) of 9 μm and a twist angle of 80 degrees. A sine wave (0.5 V, 1 kHz) is applied to the element, and after 2 seconds, the dielectric constant (ε⊥) in the short axis direction of the liquid crystal molecules is measured.

[0417] (10a) Elastic constant (K; measured at 25 °C; pN)

[0418] Positive dielectric anisotropy: An HP4284A type LCR meter manufactured by Yokogawa-Hewlett Packard Co., Ltd. is used for the measurement. A sample is placed in a horizontally aligned element with a cell gap (spacing between two glass substrates) of 20 μm. A charge from 0 volts to 20 volts is applied to the element, and the electrostatic capacitance and the applied voltage are measured. The measured values of the electrostatic capacitance (C) and the applied voltage (V) are fitted using equations (2.98) and (2.101) on page 75 of the "Liquid Crystal Device Handbook" (Nikkankogyo Shimbun), and K is obtained from equation (2.99) 11 and K 33value. Subsequently, in Equation (3.18) on page 171, the previously obtained K 11 and K 33 values are used to calculate K 22 . The elastic constant K is represented by the average value of K 11 , K 22 and K 33 obtained as described above.

[0419] (10b) Elastic constant (K 11 and K 33 ; measured at 25 °C; pN)

[0420] Negative dielectric anisotropy: When measuring, use an EC-1 type elastic constant measuring instrument manufactured by TOYO Technica Co., Ltd. Place the sample in a vertically aligned element with a cell gap of 20 μm between two glass substrates. Apply a charge from 20 V to 0 V to the element, and measure the electrostatic capacitance and the applied voltage. Use Equations (2.98) and (2.101) on page 75 of the "Liquid Crystal Device Handbook" (Nikkankogyo Shimbun) to fit the values of the electrostatic capacitance (C) and the applied voltage (V), and obtain the value of the elastic constant from Equation (2.100).

[0421] (11a) Threshold voltage (Vth; measured at 25 °C; V)

[0422] Positive dielectric anisotropy: When measuring, use an LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. The light source is a halogen lamp. Place the sample in a normally white mode TN element with a cell gap of 0.45 / Δn (μm) and a twist angle of 80 degrees between two glass substrates. The voltage (32 Hz, rectangular wave) applied to the element is increased stepwise from 0 V in units of 0.02 V to 10 V. At this time, irradiate the element with light from the vertical direction and measure the amount of light transmitted through the element. Make a voltage-transmittance curve where the transmittance is 100% when the amount of light is maximum and the transmittance is 0% when the amount of light is minimum. The threshold voltage is represented by the voltage when the transmittance becomes 90%.

[0423] (11b) Threshold voltage (Vth; measured at 25 °C; V)

[0424] Negative dielectric anisotropy: When measuring, an LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was a halogen lamp. In a VA element in a normally black mode with a cell gap of 4 μm between two glass substrates and anti-parallel rubbing directions, a sample was placed, and the element was sealed using an adhesive cured by ultraviolet light. The voltage (60 Hz, rectangular wave) applied to the element was gradually increased from 0 V in 0.02 V increments up to 20 V. At this time, light was irradiated onto the element from the vertical direction, and the amount of light transmitted through the element was measured. A voltage-transmittance curve was created such that when the amount of light was maximum, the transmittance was 100%, and when the amount of light was minimum, the transmittance was 0%. The threshold voltage was expressed as the voltage when the transmittance became 10%.

[0425] (12a) Response time (τ; measured at 25 °C; ms)

[0426] Positive dielectric anisotropy: When measuring, an LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. In a TN element in a normally white mode with a cell gap of 5.0 μm between two glass substrates and a twist angle of 80 degrees, a sample was placed. A rectangular wave (60 Hz, 5 V, 0.5 s) was applied to the element. At this time, light was irradiated onto the element from the vertical direction, and the amount of light transmitted through the element was measured. When the amount of light was maximum, it was regarded as a transmittance of 100%, and when the amount of light was minimum, it was regarded as a transmittance of 0%. The rise time (τr: rise time; milliseconds) was the time required for the transmittance to change from 90% to 10%. The fall time (τf: fall time; milliseconds) was the time required for the transmittance to change from 10% to 90%. The response time was expressed as the sum of the rise time and the fall time obtained as described above.

[0427] (12b) Response time (τ; measured at 25 °C; ms)

[0428] Negative dielectric anisotropy: When measuring, an LCD5100 type luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was a halogen lamp. The low-pass filter was set to 5 kHz. In a PVA element in a normally black mode with a cell gap of 3.2 μm between two glass substrates and anti-parallel rubbing directions, a sample was placed. The element was sealed using an adhesive cured by ultraviolet light. A voltage slightly exceeding the threshold voltage was applied to the element for 1 minute, and then, while applying a voltage of 5.6 V, light of 23.5 mW / cm 2Ultraviolet rays for 8 minutes. A rectangular wave (60 Hz, 10 V, 0.5 seconds) is applied to the element. At this time, light is irradiated on the element from the vertical direction, and the amount of light transmitted through the element is measured. When the amount of light reaches the maximum, it is regarded as a transmittance of 100%, and when the amount of light is the minimum, it is regarded as a transmittance of 0%. The response time is expressed as the time (fall time; milliseconds) required for the transmittance to change from 90% to 10%.

[0429] (13) AC afterimage (brightness change rate)

[0430] The brightness-voltage characteristics (B-V characteristics) of the liquid crystal display element described below are measured. Let it be the brightness-voltage characteristics before stress application: B(before). In addition, the voltage at which the maximum brightness can be obtained as measured here is set as Vmax. Subsequently, an alternating current of 120 Hz is applied to the element at Vmax for 20 minutes, short-circuited for 1 second, and the brightness-voltage characteristics (B-V characteristics) are measured again. Let it be the brightness-voltage characteristics after stress application: B(after). Based on these values, the following formula is used to estimate the brightness change rate ΔB (%).

[0431] ΔB (%) = [B(after) - B(before)] / B(before) (Formula 1)

[0432] These measurements are carried out with reference to International Publication No. 2000 / 43833. In the present invention, it can be said that the smaller the value of ΔB (%) at the voltage where the relative brightness becomes 21.6%, the more the generation of AC afterimage can be prevented.

[0433] Raw materials

[0434] Solmix (registered trademark) A-11 is a mixture of ethanol (85.5%), methanol (13.4%), and isopropyl alcohol (1.1%), and is obtained from Nippon Alcohol Sales Co., Ltd.

[0435] [Synthesis Example 1]

[0436] Synthesis of Compound (No. 2)

[0437]

[0438] The first process

[0439] Compound (T-1) (12.6 g), potassium carbonate (9.5 g), compound (T-2) (11.5 g) and DMF (100 ml) were placed in a reactor and stirred at 60 °C for 2 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, ethyl acetate:toluene = 1:9) to obtain compound (T-3) (12.0 g; 65%). Furthermore, compound (T-1) is a known substance and compound (T-2) is a commercially available product.

[0440] Second step

[0441] Compound (T-3) (12.0 g) and tetrahydrofuran (THF) (150 ml) were placed in a reactor and cooled to below -60 °C. While maintaining below -60 °C, n-butyllithium (n-BuLi) (1.6 M hexane solution) (20.5 ml) was added dropwise thereto, and then stirred for 1 hour. CO2 gas was blown into it until the temperature did not rise. After stirring for 30 minutes, it was returned to room temperature and further stirred for 1 hour. The reaction mixture was poured into water, the pH was adjusted to between 6 and 5 with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure and washed with a toluene / heptane mixed solvent to obtain compound (T-4) (6.5 g; 59%).

[0442] Third step

[0443] Compound (T-4) (1.89 g), compound (T-5) (1.5 g), DMAP (0.13 g) and dichloromethane (100 ml) were placed in a reactor and cooled to 0 °C. DCC (1.08 g) was added thereto, and the temperature was returned to room temperature and stirred for 12 hours. The insoluble matter was filtered off, and then the reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, the residue was purified by silica gel chromatography (volume ratio, ethyl acetate:toluene = 1:9), and reprecipitated with heptane to obtain compound (T-6) (3.7 g; 112%). Furthermore, those with ordinary knowledge in the technical field can easily synthesize compound (T-5).

[0444] Fourth step

[0445] Compound (T-6) (3.7 g), pyridinium p-toluenesulfonate (PPTS) (2.2 g), THF (50 ml) and methanol (50 ml) were placed in a reactor and stirred at 50 °C for 2 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with toluene. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, ethyl acetate:toluene = 1:4) to obtain compound (T-7) (3.24 g; 100%).

[0446] The fifth step

[0447] Compound (T-7) (3.24 g), compound (T-8) (0.78 g), DMAP (0.14 g) and dichloromethane (100 ml) were placed in a reactor and cooled to 0 °C. DCC (1.08 g) was added thereto, and the mixture was returned to room temperature and stirred for 12 hours. The insoluble matter was separated by filtration, and then the reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, the residue was purified by silica gel chromatography (volume ratio, ethyl acetate:toluene = 1:9), and reprecipitated with heptane to obtain compound (No.2) (2.83 g; 77%).

[0448] The NMR analysis values of the obtained compound (No.2) are as follows.

[0449] 1 1H-NMR: Chemical shift δ (ppm; CDCl3): 8.11 (dd, 1H), 8.04 (s, 1H), 7.77 (d, 1H), 7.74 (d, 1H), 7.02 (d, 1H), 6.89 (dd, 1H), 6.83 (d, 1H), 6.79 (d, 1H), 6.76 (dd, 1H), 6.09 (s, 1H), 5.72 (dd, 1H), 5.54 (d, 1H), 5.36 (dd, 1H), 4.61 (t, 2H), 4.29 (t, 3H), 4.15 (t, 2H), 3.94 (t, 2H), 2.95 - 2.86 (m, 4H), 2.19 (s, 2H), 1.94 (s, 3H), 1.79 (quint, 2H), 1.70 (quint, 2H), 1.55 (quint, 2H), 1.49 (quint, 2H).

[0450] The physical properties of compound (No.2) are as follows.

[0451] Transition temperature (°C): C 63.9 I Polymerization temperature (°C): 118.8

[0452] [Synthesis Example 2]

[0453] Synthesis of Compound (No. 5)

[0454] Replace the compound (T-1) in Synthesis Example 1 with compound (T-9) and perform the same operations to synthesize Compound (No. 5).

[0455]

[0456] The NMR analysis values of the obtained Compound (No. 5) are as follows.

[0457] 1 H-NMR: Chemical shift δ (ppm; CDCl3): 8.15 (dd, 1H), 8.09 (s, 1H), 7.88 (d, 1H), 7.87 (d, 1H), 7.59 (d, 2H), 7.54 (dd, 1H), 7.47 (s, 1H), 7.04 (d, 1H), 7.01 (d, 2H), 6.81 (d, 1H), 6.77 (dd, 1H), 6.11 (s, 1H), 5.73 (dd, 1H), 5.54 (d, 1H), 5.37 (dd, 1H), 4.62 (t, 2H), 4.30 (t, 2H), 4.16 (t, 2H), 3.96 (t, 2H), 3.02 - 2.96 (m, 4H), 1.79 (quint, 2H), 1.70 (quint, 2H), 1.55 (quint, 2H), 1.49 (quint, 2H).

[0458] The physical properties of Compound (No. 5) are as follows.

[0459] Transition temperature (°C): C 79.49 I Polymerization temperature (°C): 145.6

[0460] Synthesis of Compound (T-9)

[0461]

[0462] Dissolve compound (T-10) (7.1 g) and 4-iodophenol (20 g) in toluene (100 ml), add water (100 ml), ethanol (100 ml), Pd(PPh3)4 (0.54 g), tetrabutylammonium bromide (TBAB) (0.76 g), and potassium carbonate (9.72 g), and reflux for 6 hours. After the reaction is completed, extract with ethyl acetate, wash with water, then dry with anhydrous magnesium sulfate, and concentrate under reduced pressure to obtain a light brown solid. Dissolve the solid in a solution, perform silica gel column chromatography (volume ratio, ethyl acetate:toluene = 9:1) and recrystallization (methanol) to obtain compound (T-9) (3.7 g; 45%). Furthermore, compound (T-10) is a known substance.

[0463] [Synthesis Example 3]

[0464] Synthesis of Compound (No. 3)

[0465] Replace compound (T-5) in Synthesis Example 1 with compound (T-11) and perform the same operations to synthesize compound (No. 3).

[0466]

[0467] The NMR analysis values of the obtained compound (No. 3) are as follows.

[0468] 1 1H-NMR: Chemical shift δ (ppm; CDCl3): 8.15 (dd, 1H), 8.08 (s, 1H), 7.80 (d, 1H), 7.76 (d, 1H), 7.51 (d, 2H), 7.45 (s, 1H), 7.42 (dd, 1H), 7.18 (d, 1H), 6.96 (d, 2H), 6.90 (dd, 1H), 6.85 (d, 1H), 6.11 (s, 1H), 5.78 (dd, 1H), 5.55 (d, 1H), 5.37 (dd, 1H), 4.62 (t, 2H), 4.31 (t, 2H), 4.17 (t, 2H), 4.01 (t, 2H), 2.98 - 2.89 (m, 4H), 2.30 (s, 3H), 1.95 (s, 3H), 1.83 (quint, 2H), 1.73 (quint, 2H), 1.55 (quint, 2H), 1.49 (quint, 2H).

[0469] The physical properties of compound (No. 3) are as follows.

[0470] Transition temperature (°C): C 76.2I Polymerization temperature (°C): 110.7

[0471] Synthesis of compound (T-11)

[0472]

[0473] First step

[0474] Dissolve compound (T-12) (18 g) and 4-iodophenol (16.7 g) in toluene (150 ml), add water (70 ml), ethanol (70 ml), Pd(PPh3)4 (0.88 g), TBAB (2.5 g) and potassium carbonate (21 g), and reflux under heating for 6 hours. After completion of the reaction, extract with ethyl acetate, wash with water, then dry with anhydrous magnesium sulfate, and concentrate under reduced pressure to obtain a light brown solid. Heat and wash the solid with toluene to obtain compound (T-13) (13 g; 60%). Furthermore, compound (T-12) is a known substance.

[0475] Second step

[0476] Put compound (T-13) (5 g), potassium carbonate (4.9 g), compound (T-14) (5.26 g) and DMF (100 ml) into a reactor, and stir at 60 °C for 2 hours. Inject the reaction mixture into water, and extract the aqueous layer with ethyl acetate. Wash the organic layer with water, and dry with anhydrous magnesium sulfate. Concentrate the solution under reduced pressure, and purify the residue by silica gel chromatography (volume ratio, ethyl acetate: toluene = 1:9) to obtain compound (T-15) (7.5 g; 94%). Furthermore, compound (T-14) is a known substance.

[0477] Third step

[0478] Put compound (T-15) (7.5 g), pyridinium p-toluenesulfonate (PPTS) (6.2 g), THF (50 ml) and methanol (50 ml) into a reactor, and stir at 50 °C for 2 hours. Inject the reaction mixture into water, and extract the aqueous layer with ethyl acetate. Wash the organic layer with water, and dry with anhydrous magnesium sulfate. Concentrate the solution under reduced pressure, and purify the residue by silica gel chromatography (volume ratio, ethyl acetate: toluene = 1:9) to obtain compound (T-11) (5.6 g; 92%).

[0479] [Synthesis Example 4]

[0480] Synthesis of compound (No. 46)

[0481] Replace the compound (T-5) in Synthesis Example 1 with the compound (T-16), and perform the same operations. Thus, the compound (No. 46) can be synthesized.

[0482]

[0483] The NMR analysis values of the obtained compound (No. 46) are as described below.

[0484] 1 1H-NMR: Chemical shift δ (ppm; CDCl3): 8.14 (dd, 1H), 8.08 (s, 1H), 7.80 (d, 1H), 7.76 (d, 1H), 7.50 (d, 2H), 7.45 (s, 1H), 7.42 (dd, 1H), 7.18 (d, 1H), 6.96 (d, 2H), 6.90 (dd, 1H), 6.84 (d, 1H), 6.10 (s, 1H), 5.73 (dd, 1H), 5.55 (d, 1H), 5.37 (dd, 1H), 4.62 (t, 2H), 4.31 (t, 2H), 4.03 (t, 2H), 3.97 (d, 2H), 3.48 (t, 2H), 3.25 (d, 2H), 2.98 - 2.89 (m, 4H), 2.30 (s, 3H), 1.95 - 1.5 (m, 10H), 1.1 - 0.9 (m, 4H)

[0485] The physical properties of the compound (No. 46) are as described below.

[0486] Transition temperature (°C): C 115.5 I Polymerization temperature (°C): 147.9

[0487] Synthesis of the compound (T-16)

[0488] In the synthesis of the compound (T-11), use the compound (T-17) instead of the compound (T-14). Thus, the compound (T-16) is synthesized.

[0489]

[0490] [Synthesis Example 5]

[0491] Synthesis of the compound (No. 47)

[0492] Replace the compound (T-5) in Synthesis Example 1 with the compound (T-18), and perform the same operations. Thus, the compound (No. 47) can be synthesized. Furthermore, for those with ordinary knowledge in this technical field, the compound (T-18) can be easily synthesized using 2,7-dihydro-2,7-phenanthrenediol, which is a known substance.

[0493]

[0494] The NMR analysis values of the obtained compound (No. 47) are as described below.

[0495] 1 1H-NMR: Chemical shift δ (ppm; CDCl3): 8.11 (dd, 1H), 8.05 (s, 1H), 7.78 (d, 1H), 7.76 (d, 1H), 7.71 (d, 2H), 7.65 (d, 1H), 7.12 (dd, 1H), 7.09 (s, 1H), 6.90 (dd, 2H), 6.83 (s, 1H), 6.82 (dd, 1H), 6.78 (s, 1H), 6.10 (s, 1H), 5.73 (dd, 1H), 5.55 (d, 1H), 5.37 (dd, 1H), 4.62 (t, 2H), 4.30 (t, 2H), 4.17 (t, 2H), 4.00 (t, 2H), 2.98 - 2.85 (m, 8H), 1.81 (quint, 2H), 1.73 (quint, 2H), 1.55 (quint, 2H), 1.49 (quint, 2H).

[0496] The physical properties of the compound (No. 47) are as described below.

[0497] Transition temperature (°C): C 105.2 I Polymerization temperature (°C): 146.8

[0498] The following compounds (No. 1) to compound (No. 47) can be synthesized according to the synthesis methods described in the synthesis examples as specific examples of compound (1).

[0499]

[0500]

[0501]

[0502]

[0503]

[0504]

[0505] 2. Usage examples of the component

[0506] The compounds in the usage examples are represented by notations based on the definitions 1) to 5) in Table 2 below. In Table 2, the stereoconfiguration related to 1,4-cyclohexylene is the trans configuration. The numbers in the parentheses after the notations correspond to the compound numbers. The notation (-) means other liquid crystalline compounds. The ratio (percentage) of the liquid crystalline compound is the weight percentage (wt%) based on the weight of the liquid crystal composition. Finally, the characteristic values of the composition are summarized.

[0507] Table 2: Notation method for compounds: R-(A1)-Z……Zn-(An)-R’

[0508]

[0509]

[0510]

[0511]

[0512] 1. Raw materials

[0513] A composition added with a polar compound is injected into an element without an alignment film. After linearly polarized light is irradiated, the alignment of liquid crystal molecules in the element is confirmed. First, the raw materials are described. The raw materials are appropriately selected from compositions such as composition (M1) to composition (M8) and compounds such as compound (No.1) to compound (No.47) (1). The compositions are as follows.

[0514] [Composition (M1)]

[0515]

[0516] NI = 80.8 °C; Tc < -20 °C; Δn = 0.108; Δε = -3.8; Vth = 2.02 V; η = 19.8 mPa·s; γ1 = 115.0 mPa·s.

[0517] [Composition (M2)]

[0518]

[0519] NI = 85.1 °C; Tc < -20 °C; Δn = 0.109; Δε = 5.3; Vth = 1.83 V; η = 20.1 mPa·s; γ1 = 82.4 mPa·s.

[0520] [Composition (M3)]

[0521]

[0522] NI = 78.4 °C; Tc < -20 °C; Δn = 0.108; Δε = 10.4; Vth = 1.35 V; η = 17.8 mPa·s; γ1 = 79.9 mPa·s.

[0523] [Composition (M4)]

[0524]

[0525] NI = 77.4 °C; Tc < -20 °C; Δn = 0.108; Δε = 10.2; Vth = 1.35 V; η = 13.2 mPa·s; γ1 = 69.0 mPa·s.

[0526] [Composition (M5)]

[0527]

[0528]

[0529] NI = 89.1 °C; Tc < -20 °C; Δn = 0.107; Δε = -3.7; Vth = 2.32 V; γ1 = 129.7 mPa·s.

[0530] [Composition (M6)]

[0531]

[0532] NI = 85.7 °C; Tc < -20 °C; Δn = 0.104; Δε = -3.5; Vth = 2.12 V; γ1 = 102 mPa·s.

[0533] [Composition (M7)]

[0534]

[0535] NI = 81.3 °C; Δn = 0.091; Δε = -3.4; Vth = 2.25 V.

[0536] [Composition (M8)]

[0537]

[0538]

[0539] NI = 83.4 °C; Δn = 0.104; Δε = -3.4; Vth = 2.26 V.

[0540] 2. Alignment of Liquid Crystal Molecules

[0541] Examples of Use 1 to Examples of Use 7

[0542] (Preparation of Specimens)

[0543] In composition (M1), compound (No. 2) as compound (1) is added at ratios of 0.1 wt%, 0.3 wt%, 0.5 wt%, 1.0 wt%, 3.0 wt%, 5.0 wt%, and 10.0 wt% as a compound capable of horizontally aligning liquid crystal molecules, and R as an antioxidant is added at a ratio of 150 ppm. 40 Compound (AO-1) with a normal heptyl group. Heating and stirring are carried out at 100 °C, and then, after returning to room temperature and leaving it for one week, no crystallization or the like precipitates from these mixtures and they are completely dissolved.

[0544] (Fabrication of Elements)

[0545] These mixtures are injected into an IPS element without an alignment film at 90 °C. These mixtures show an isotropic phase at 90 °C, so these mixtures are injected at a temperature above the upper limit temperature of the nematic phase. While heating the IPS element at 90 °C, polarized ultraviolet light having peaks at wavelengths of 313 nm, 335 nm, and 365 nm is irradiated to the element from the normal direction for a certain period of time, thereby performing an alignment treatment, and the irradiation is continued until the alignment becomes good.

[0546] (Irradiation Conditions of Polarized Ultraviolet Light)

[0547] · The illuminance at a wavelength of 313 nm is 3 mW / cm 2 . Measured using UIT-150 and UVD-S313 manufactured by Ushio Electric Co., Ltd.

[0548] · The ultraviolet irradiation lamp used is USH-250BY manufactured by Ushio Electric Co., Ltd.

[0549] · The exposure machine unit used is ML-251A / B manufactured by Ushio Electric Co., Ltd.

[0550] · The polarized ultraviolet light is formed using a wire grid polarizing element (ProFluxUVT260A manufactured by Polatechno Co., Ltd.).

[0551] (Method for Confirming Alignment)

[0552] The element is made parallel to the polarization axis of linearly polarized light and placed on a polarizing microscope in which the polarizer and the analyzer are orthogonally arranged, and light is irradiated to the element from below to observe whether there is light leakage. When the light does not pass through the element, it is judged that the alignment is "good". When the light passing through the element is observed, it is judged that the alignment is "bad" and the irradiation is insufficient.

[0553] (AC afterimage)

[0554] Use the said unit to measure the AC afterimage and summarize it in Table 3 below.

[0555] Use Examples 8 to 42

[0556] Use Composition (M1), add R as an antioxidant at a ratio of 150 ppm 40 Compound (AO-1) with a normal heptyl group, and mix Compound (1) shown in the following Table 3 as a compound that can horizontally align liquid crystal molecules. In addition, operate in the same manner as in Use Example 1. Measure the AC afterimage using the same method as in Use Example 1. Summarize the results in Table 3 below. The mixtures of Use Examples 8 to 14 also show an isotropic phase at 90°C. Furthermore, hereinafter, the compound that can horizontally align liquid crystal molecules may sometimes be referred to as a "compound for horizontal alignment", etc.

[0557] Table 3

[0558]

[0559] Change the composition M1 used in Use Examples 1 to 42 to M2 to M8, and perform the same operations respectively. As a result, in any case, there is no significant change in the AC afterimage.

[0560] Properly select from the compositions from Composition (M1) to Composition (M8) and the compounds (1) of Compounds (No.1) to (No.45), and perform the same operations. As a result, in any case, the AC afterimage is 15% or less.

[0561] Comparative Examples 1 to 14

[0562] Mix Compound (S-1) described in Patent Document 3 and Compound (S-2) described in Patent Document 2 as compounds that can horizontally align liquid crystal molecules in Composition (M1) at the ratios shown in Table 4 below, and evaluate the AC afterimage by the same operations as in the use examples. The mixtures of Comparative Examples 1 to 21 also show an isotropic phase at 90°C.

[0563] As a result, compared with the compounds of the embodiments of the present invention, in any compound, the value of the AC afterimage in the use examples is 20% or more. In addition, perform the same evaluation using Composition (M2) to Composition (M8), and the results all show the same tendency as in the case of using Composition (M1).

[0564]

[0565] Table 4

[0566]

[0567] Regarding the irradiation time, it was 10 minutes to 30 minutes in the use examples and 30 minutes to 60 minutes in the comparative examples, and the sensitivity in the use examples was basically good.

[0568] In the use examples, although the types and amounts of the composition or the polar compound, i.e., compound (1) which is a compound capable of horizontally aligning liquid crystal molecules, were changed, there was no dissolution residue or precipitation, and the value of the AC afterimage did not change significantly. On the other hand, in the comparative examples, the value of the AC afterimage was 20% or more. Therefore, it can be understood that: as long as compound (1) of the embodiment of the present invention is used, the AC afterimage can be suppressed to a low level, and a horizontally aligned liquid crystal display element with excellent reliability can be obtained. In addition, as long as the liquid crystal composition of the embodiment of the present invention is used, a liquid crystal display element having at least one of the characteristics of a wide temperature range in which the element can be used, a short response time, a high voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifespan can be obtained. Furthermore, a liquid crystal display element having the following liquid crystal composition can be obtained, and the liquid crystal composition satisfies at least one of the characteristics such as a high upper limit temperature of the nematic phase, a low lower limit temperature of the nematic phase, a small viscosity, an appropriate optical anisotropy, a large negative dielectric anisotropy, a large specific resistance, a high stability to ultraviolet rays, and a high stability to heat.

[0569] [Industrial Applicability]

[0570] The liquid crystal composition of the embodiment of the present invention can be used in liquid crystal monitors, liquid crystal televisions, etc.

Claims

1. Use of a compound represented by formula (1) for a liquid crystal display element without an alignment film; In formula (1), a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1, 2 or 3; Ring A 1 and Ring A 2 and Ring A 3 and Ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, the group represented by formula (A-1) or the group represented by formula (A-2). These Ring As 1 and Ring A 2 and Ring A 3 and Ring A 4 may have at least one hydrogen substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 and these alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, -Sp 1 -P 1 or -Sp 2 -P 2 may have at least one hydrogen substituted by fluorine or chlorine. Among them, Ring A 1 、Ring A 2 、Ring A 3 or Ring A 4 is at least one of the group represented by formula (A-1) or the group represented by formula (A-2). In formula (A-1) and formula (A-2), Q 1 and Q 2 are independently -CH2-, -O-, -N(-R 8 ), or -S-. Here, R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms. In said R 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine; When a is 2, the two rings A 1 can be different. When b is 2, the two rings A 4 can be different; Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are independently a single bond, -(CH2)2-, -C≡C-, -C≡CC≡C-, -COO- or -OCO-, but Z 2 , Z 3 or Z 4 At least one of them is -COO- or -OCO-; when a is 2, the two Z 1 But different, when b is 2, the two Z 5 Can be different; Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in said Sp 1 and Sp 2 at least one -CH2- may be substituted by -O-, -CO-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 substituted; In the presence of multiple Sp 1 or Sp 2 any two of them may be different; P 1 and P 2 independently represents a group represented by any one of formulas (1b) to (1h), and in the case where there are multiple P 1 or P 2 any two of them may be different; In formulas (1b) to (1h), M 1 、M 2 、M 3 and M 4 X is independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine or chlorine; 1 For -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, wherein R 9 In the above, at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, but there is no R 9 In the case of fluorine or chlorine; R 2 and R 6 are independently hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and at least one hydrogen in said R 2 and R 6 may be substituted by fluorine or chlorine, and at least one -CH2- may be substituted by -O-; R 3 , R 4 , R 5 and R 7 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, wherein R 3 , R 4 , R 5 and R 7 In the above, at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, but there is no R 5 and R 7 In the case of fluorine or chlorine.

2. Use of the compound according to claim 1, wherein, In formula (1), a and b are independently 0, 1 or 2, and the sum of a and b is 0, 1 or 2; Ring A 1 、Ring A 2 、Ring A 3 and Ring A 4 are each independently 1,4 - cyclohexylene, 1,4 - cyclohexenylene, 1,4 - phenylene, naphthalene - 2,6 - diyl, decahydronaphthalene - 2,6 - diyl, 1,2,3,4 - tetrahydronaphthalene - 2,6 - diyl, tetrahydropyran - 2,5 - diyl, 1,3 - dioxane - 2,5 - diyl, pyrimidine - 2,5 - diyl, pyridine - 2,5 - diyl, fluorene - 2,7 - diyl, phenanthrene - 2,7 - diyl, anthracene - 2,6 - diyl, perhydrocyclopenta[a]phenanthrene - 3,17 - diyl, 2,3,4,7,8,9,10,11,12,13,14,15,16,17 - tetradecahydrocyclopenta[a]phenanthrene - 3,17 - diyl, the group represented by formula (A - 1) or the group represented by formula (A - 2). These Ring A 1 、Ring A 2 、Ring A 3 and Ring A 4 may each have at least one hydrogen substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 . These alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, -Sp 1 -P 1 or -Sp 2 -P 2 may each have at least one hydrogen substituted by fluorine or chlorine. Among them, at least one of Ring A 1 、Ring A 2 、Ring A 3 or Ring A 4 is the group represented by formula (A - 1) or the group represented by formula (A - 2). Q 1 and Q 2 are each independently -CH2-, -O-, -N(R 8 ), or -S-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms. Among the R 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH = CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine. When a is 2, the two rings A 1 can be different. When b is 2, the two rings A 4 can be different; Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are independently a single bond, -(CH2)2-, -C≡C-, -C≡CC≡C-, -COO- or -OCO-, but Z 2 , Z 3 or Z 4 At least one of them is -COO- or -OCO-; when a is 2, the two Z 1 But different, when b is 2, the two Z 5 Can be different; Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp 1 and Sp 2 , at least one -CH2- may be substituted by -O-, -COO- or -OCO-, at least one -(CH2)2- may be substituted by -CH=CH-, and at least one hydrogen may be substituted by fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 substituted. In the case where there are multiple Sp 1 or Sp 2 , any two of them may be different; P 1 and P 2 independently represents a group represented by any one of formulas (1b) to (1h), and in the case where there are multiple P 1 or P 2 any two of them may be different; In formulas (1b) to (1h), M 1 、M 2 、M 3 and M 4 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine or chlorine, X 1 For -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, wherein R 9 In the above, at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, but there is no R 9 In the case of fluorine or chlorine; R 2 and R 6 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and in said R 2 and R 6 at least one hydrogen may be substituted by fluorine or chlorine, and at least one -CH2- may be substituted by -O-; R 3 、R 4 、R 5 and R 7 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms. Among the said R 3 、R 4 、R 5 and R 7 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 5 and R 7 are fluorine or chlorine.

3. Use of the compound according to claim 1 or 2, wherein, The compound is represented by any one of formulas (1-1) to (1-3); In formulas (1-1) to (1-3), Ring A 1 and Ring A 2 and Ring A 3 and Ring A 4 are each independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, a group represented by formula (A-1) or formula (A-2). In these Ring As 1 and Ring A 2 and Ring A 3 and Ring A 4 at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 and in these alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, -Sp 1 -P 1 or -Sp 2 -P 2 at least one hydrogen may be substituted by fluorine or chlorine. Among them, at least one of Ring A 1 and Ring A 2 and Ring A 3 or Ring A 4 is formula (A-1) or formula (A-2). Q 1 and Q 2 are each independently -CH2-, -O-, -N(R 8 )-, or -S-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms. In the said R 8 at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine; Z 2 , Z 3 and Z 4 are independently a single bond, -(CH2)2-, -C≡C-, -C≡CC≡C-, -COO- or -OCO-, but Z 2 , Z 3 or Z 4 At least one of is -COO- or -OCO-; Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and the Sp 1 and Sp 2 in, at least one -CH2- may be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- may be substituted by -CH=CH-, at least one hydrogen may be substituted by fluorine, chlorine or -Sp 1 -P 1 or -Sp 2 -P 2 substituted, in the presence of multiple Sp 1 or Sp 2 cases, any two may be different; P 1 and P 2 independently is a group represented by any one of formula (1b) to formula (1h), and in the case where there are multiple P 1 or P 2 any two of them may be different; In formulas (1b) to (1h), M 1 、M 2 、M 3 and M 4 X is independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine or chlorine; 1 For -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, wherein R 9 In the above, at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, but there is no R 9 In the case of fluorine or chlorine; R 2 and R 6 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and in said R 2 and R 6 at least one hydrogen may be substituted by fluorine or chlorine, and at least one -CH2- may be substituted by -O-; R 3 , R 4 , R 5 and R 7 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, wherein R 3 , R 4 , R 5 and R 7 In the above, at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, but there is no R 5 and R 7 In the case of fluorine or chlorine.

4. Use of the compound according to claim 3, wherein, In formulas (1-1) to (1-3), Ring A 1 and Ring A 2 and Ring A 3 and Ring A 4 are independently 1,4 - cyclohexylene, 1,4 - phenylene, naphthalene - 2,6 - diyl, fluorene - 2,7 - diyl, phenanthrene - 2,7 - diyl, a group represented by formula (A - 1) or a group represented by formula (A - 2). Among these Ring As 1 and Ring A 2 and Ring A 3 and Ring A 4 , at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 11 carbon atoms, an alkenyloxy group having 2 to 11 carbon atoms, -Sp 1 -P 1 or -Sp 2 -P 2 . Among them, at least one of Ring A 1 and Ring A 2 and Ring A 3 or Ring A 4 is a group represented by formula (A - 1) or a group represented by formula (A - 2). Q 1 and Q 2 are independently -CH2-, -O-, -N(R 8 )-, or -S-. Here, R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms. Among the said Rs 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine. Z 2 , Z 3 , and Z 4 are independently a single bond, -(CH2)2-, -C≡C-C≡C-, -C≡C-, -COO-, or -OCO-, provided that at least one of Z 2 , Z 3 , or Z 4 is -COO- or -OCO-; Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, wherein the Sp 1 and Sp 2 in, at least one -CH2- can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- can be substituted by -CH=CH-, at least one hydrogen can be substituted by -Sp 1 -P 1 or -Sp 2 -P 2 substituted, in the presence of multiple Sp 1 or Sp 2 cases, any two can be different; P 1 and P 2 independently is a group represented by any one of formula (1b), formula (1c), formula (1d) or formula (1e), and in the case where there are multiple P 1 or P 2 any two of them may be different; In formulas (1b) to (1e), M 1 、M 2 、M 3 and M 4 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is replaced by fluorine or chlorine, X 1 For -N(-R 9 )-, -O- or -S-, where R 9 are independently hydrogen or an alkyl group having 1 to 15 carbon atoms, wherein R 9 In the above, at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, but there is no R 9 In the case of fluorine or chlorine; R 2 and R 6 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and in said R 2 and R 6 at least one hydrogen may be substituted by fluorine or chlorine, and at least one -CH2- may be substituted by -O-; R 3 、R 4 and R 5 are each independently hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 3 、R 4 and R 5 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 5 is fluorine or chlorine.

5. Use of the compound according to claim 3, wherein, In formulas (1-1) to (1-3), Ring A 1 and Ring A 2 and Ring A 3 and Ring A 4 are independently 1,4 - cyclohexylene, 1,4 - phenylene, naphthalene - 2,6 - diyl, fluorene - 2,7 - diyl, phenanthrene - 2,7 - diyl, formula (A - 1) or formula (A - 2), and for these Ring As 1 and Ring A 2 and Ring A 3 and Ring A 4 at least one hydrogen can be substituted by fluorine, chlorine, methyl or ethyl, wherein for Ring A 1 and Ring A 2 and Ring A 3 or Ring A 4 at least one is formula (A - 1) or formula (A - 2), Q 1 and Q 2 are independently -CH2-, -O-, -N(R 8 )-, or -S-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and for said R 8 at least one -CH2- can be substituted by -O- or -S-, at least one -(CH2)2- can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine Z 2 , Z 3 and Z 4 are independently a single bond, -(CH2)2-, -C≡CC≡C-, -C≡C-, -COO- or -OCO-, but Z 2 , Z 3 or Z 4 At least one of is -COO- or -OCO-; Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms. In the Sp 1 and Sp 2 , at least one -CH2- can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- can be substituted by -CH=CH-, and at least one hydrogen can be substituted by -Sp 1 -P 1 or -Sp 2 -P 2 . In the case where there are multiple Sp 1 or Sp 2 , any two of them can be different; P 1 and P 2 independently represents a group represented by formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) or formula (1e-1). In formulas (1b-1), (1b-2), (1b-3), (1b-4), (1b-5), (1c-1), (1d-1), (1d-2) and (1e-1), X 2 , X 3 , X 4 , X 5 and X 6 are independently -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, wherein R 9 In the above, at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, at least one hydrogen may be replaced by fluorine or chlorine, but there is no R 9 In the case of fluorine or chlorine.

6. Use of the compound according to claim 3, wherein, Among the compounds represented by Formula (1-1) to Formula (1-3), Z 2 , Z 3 or Z 4 is any one of -COO- or -OCO-, Q 1 is -CH2- or -N(R 8 ), Q 2 is -N(R 8 ), where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in the said R 8 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine.

7. Use of the compound according to claim 1 or 2, wherein, The compound is represented by any one of formulas (1-1-11-1) to (1-1-11-2), (1-2-11-1) to (1-2-11-4), (1-1-12-1) to (1-1-12-2), (1-2-12-1) to (1-2-12-4), (1-1-21-1) to (1-1-21-2), (1-2-21-1) to (1-2-21-4), (1-1-22-1) to (1-1-22-2) and (1-2-22-1) to (1-2-22-4); In these formulas, Sp 1 and Sp 2 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in the Sp 1 and Sp 2 , at least one -CH2- can be substituted by -O-, -COO-, -OCOO- or -OCO-, at least one -(CH2)2- can be substituted by -CH=CH-, and at least one hydrogen can be substituted by -Sp 1 -P 1 or -Sp 2 -P 2 ; P 1 , P 2 、Sp 1 and Sp 2 In the partial structure other than , at least one hydrogen may be replaced by fluorine, chlorine, methyl or ethyl; Q 1 is -CH2- or -N(-R 8 )-, Q 2 is -N(-R 8 )-, where R 8 is hydrogen or an alkyl group having 1 to 15 carbon atoms, and in said R 8 , at least one -CH2- may be replaced by -O- or -S-, at least one -(CH2)2- may be replaced by -CH=CH- or -C≡C-, and at least one hydrogen may be replaced by fluorine or chlorine, provided that there is no case where R 8 is fluorine or chlorine. P 1 and P 2 independently represents a group represented by formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) or formula (1e-1), In formula (1b-1), formula (1b-2), formula (1b-3), formula (1b-4), formula (1b-5), formula (1c-1), formula (1d-1), formula (1d-2) or formula (1e-1), X 2 , X 3 , X 4 , X 5 and X 6 are independently -N(-R 9 )-, -O- or -S-, where R 9 is hydrogen or an alkyl group having 1 to 15 carbon atoms, in the R 9 , at least one -CH2- may be substituted by -O- or -S-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine, provided that there is no case where R 9 is fluorine or chlorine.

8. Use of the compound according to claim 7, wherein, In the compounds represented by Formula (1-1-11-1) to Formula (1-1-11-2), Formula (1-2-11-1) to Formula (1-2-11-4), Formula (1-1-12-1) to Formula (1-1-12-2), Formula (1-2-12-1) to Formula (1-2-12-4), Formula (1-1-21-1) to Formula (1-1-21-2), Formula (1-2-21-1) to Formula (1-2-21-4), Formula (1-1-22-1) to Formula (1-1-22-2), or Formula (1-2-22-1) to Formula (1-2-22-4), Sp 1 and Sp 2 are independently alkylene groups having 1 to 10 carbon atoms, and in the Sp 1 and Sp 2 , at least one -CH2- may be substituted with -O-, and at least one hydrogen may be substituted with fluorine, chlorine, or -Sp 1 -P 1 or -Sp 2 -P 2 .

9. Use of a liquid crystal composition containing at least one compound according to any one of claims 1 to 8 for a liquid crystal display element without an alignment film.

10. Use of the liquid crystal composition according to claim 9, wherein, The liquid crystal composition further contains at least one compound selected from the group consisting of compounds represented by formulas (2) to (4); In formulas (2) to (4), R 11 and R 12 are independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R 11 and R 12 at least one -CH2- may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; Ring B 1 , Ring B 2 , Ring B 3 and Ring B 4 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or pyrimidine-2,5-diyl; Z 11 、Z 12 and Z 13 are independently a single bond, -(CH2)2-, -CH=CH-, -C≡C- or -COO-.

11. Use of the liquid crystal composition according to claim 9 or 10, wherein, The liquid crystal composition further contains at least one compound selected from the group consisting of compounds represented by formulas (5) to (7); In formulas (5) to (7), R 13 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R 13 at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine; X 11 is fluorine, chlorine, -OCF3, -OCHF2, -CF3, -CHF2, -CH2F, -OCF2CHF2 or -OCF2CHFCF3; Ring C 1 and Ring C 2 and Ring C 3 independently is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be substituted by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z 14 、Z 15 and Z 16 are each independently a single bond, -(CH2)2-, -CH=CH-, -CH=CF-, -CF=CF-, -C≡C-, -COO-, -CF2O-, -OCF2-, -CH2O-, -CH=CF-CF2O-, -CF=CF-CF2O- or -(CH2)4-; L 11 and L 12 are independently hydrogen or fluorine.

12. Use of the liquid crystal composition according to claim 9 or 10, wherein, The liquid crystal composition further contains at least one compound selected from the group consisting of compounds represented by formula (8); In formula (8), R 14 is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in said R 14 at least one -CH2- may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; X 12 is -C≡N or -C≡C-C≡N; Ring D 1 independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z 17 independently a single bond, -(CH2)2-, -C≡C-, -COO-, -CF2O-, -OCF2- or -CH2O-; L 13 and L 14 are independently hydrogen or fluorine; i is 1, 2, 3 or 4.

13. Use of the liquid crystal composition according to claim 9 or 10, wherein, The liquid crystal composition further contains at least one compound selected from the group consisting of compounds represented by formulas (9) to (15), (DB-1) and (DB-2); In formulas (9) to (15), R 15 and R 16 independently is an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in the said R 15 and R 16 at least one -CH2- may be substituted by -O-, and at least one hydrogen may be substituted by fluorine; R 17 is hydrogen, an alkyl group having 1 to 10 carbon atoms, a fluoroalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a fluoroalkenyl group having 2 to 10 carbon atoms, provided that in said R 17 at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine, provided that there is no case where R 17 is fluorine; Ring E 1 and Ring E 2 and Ring E 3 and Ring E 4 independently is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one hydrogen may be substituted by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl; Ring E 5 and Ring E 6 independently is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl; Z 18 , Z 19 , Z 20 and Z 21 are independently a single bond, -(CH2)2-, -COO-, -CH2O-, -OCF2- or -OCF2-(CH2)2-; L 15 and L 16 are independently fluorine or chlorine; S 11 is hydrogen or methyl; X is independently -CHF- or -CF2-; j, k, m, n, p, q, r and s are independently 0 or 1, the sum of k, m, n and p is 0, 1, 2 or 3, the sum of q, r and s is 0, 1, 2 or 3, and t is 1, 2 or 3; In formulas (DB-1) and (DB-2), X 100 independently -S-, -O- or -CH2-; a 100 and a 200 are independently 0, 1 or 2, and the sum of a 100 and a 200 is 0, 1, 2 or 3; R 100 and R 200 are independently hydrogen, an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and in the case of said R 100 and R 200 at least one -CH2- may be replaced by -O-, and at least one hydrogen may be replaced by fluorine, provided that there is no case where R 100 and R 200 is fluorine; A 100 and A 200 independently is 1,2-cyclopropylidene, 1,3-cyclobutylidene, 1,3-cyclopentylidene, 1,3-cyclopentenylidene, 1,4-cyclohexylidene, 1,4-cyclohexenylidene, 1,4-cycloheptylidene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, dihydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-xanthene-2,6-diyl or 9H-fluorene-2,7-diyl, and at least one hydrogen in the A 100 and A 200 may be substituted by fluorine, chlorine, -CF3, -CHF2, -CH2F, -OCF3, -OCHF2, -OCH2F or -C≡N; Z 100 and Z 200 independently is a single bond or an alkylene group having 1 to 6 carbon atoms, and the Z 100 and Z 200 in, at least one -CH2- may be substituted by -O-, -S-, -CO-, -COO-, -OCO-, -CF2O-, -OCF2-, -(CH2)3O-, -O(CH2)3-, -CH=CH-CH2O-, -OCH2-CH=CH- or -SiH2-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; L 100 and L 101 are independently fluorine, chlorine, -CF3 or -CHF2; L 102 , L 103 , L 104 and L 105 are independently hydrogen, fluorine, chlorine, -CF3, -CHF2, -CH2F, -OCF3, -OCHF2 or -OCH2F, and L is absent. 102 , L 103 , L 104 and L 105 All hydrogen, but L 102 , L 103 , L 104 and L 105 Any one or both of may be hydrogen.

14. Use of the liquid crystal composition according to claim 9 or 10, wherein, The liquid crystal composition contains at least one polymerizable compound selected from the group consisting of compounds represented by formula (16); In formula (16), Ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidin-2-yl or pyridin-2-yl. In these rings F and I, at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine; Ring G is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidin-2,5-diyl or pyridin-2,5-diyl. In these rings G, at least one hydrogen may be substituted by fluorine, chlorine, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine; Z 22 and Z 23 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and said Z 22 and Z 23 in, at least one -CH2- may be substituted by -O-, -CO-, -COO- or -OCO-, at least one -(CH2)2- may be substituted by -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)- or -C(CH3)=C(CH3)-, and at least one hydrogen may be substituted by fluorine or chlorine; Sp 11 、Sp 12 and Sp 13 are independently a single bond or an alkylene group having 1 to 10 carbon atoms, and in said Sp 11 、Sp 12 and Sp 13 at least one -CH2- may be substituted by -O-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine; u is 0, 1 or 2; f, g and h are independently 0, 1, 2, 3 or 4, and the sum of f, g and h is 2 or more, P 11 、P 12 and P 13 are each independently a polymerizable group selected from the group consisting of the groups represented by formula (P-1) to formula (P-5); In formula (P-1) to formula (P-5), M 11 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, and in said M 11 , at least one hydrogen may be substituted by fluorine or chlorine, and at least one -CH2- may be substituted by -O-; M 12 and M 13 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine.

15. Use of the liquid crystal composition according to claim 9 or 10, wherein, The liquid crystal composition contains at least one polymerizable compound selected from the group consisting of compounds represented by formula (16-1) to formula (16-28); In formula (16-1) to formula (16-28), Sp 11 、Sp 12 and Sp 13 are independently a single bond or an alkylene group having 1 to 10 carbon atoms. In the Sp 11 、Sp 12 and Sp 13 , at least one -CH2- can be substituted by -O-, -COO-, -OCO- or -OCOO-, at least one -(CH2)2- can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine, u is 0, 1 or 2, and g and h are independently 0, 1, 2, 3 or 4. Z 23 is independently a single bond or an alkylene group having 1 to 10 carbon atoms, and the Z 23 in which at least one -CH2- may be substituted by -O-, -CO-, -COO- or -OCO-, at least one -(CH2)2- may be substituted by -CH=CH-, -C(CH3)=CH-, -CH=C(CH3)- or -C(CH3)=C(CH3)-, and at least one hydrogen may be substituted by fluorine or chlorine P 11 、P 12 and P 13 are each independently a polymerizable group selected from the group consisting of the groups represented by formula (P-1) to formula (P-3); In formula (P-1) to formula (P-3), M 11 is hydrogen, fluorine, chlorine or an alkyl group having 1 to 5 carbon atoms, in which at least one hydrogen may be substituted by fluorine or chlorine, and at least one -CH2- may be substituted by -O-; M 11 and M 12 and M 13 are independently hydrogen, fluorine, chlorine, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen is substituted by fluorine or chlorine.

16. Use of the liquid crystal composition according to claim 9 or 10, wherein, The liquid crystal composition further contains at least one of a polymerizable compound other than formula (1) according to claim 1 and formula (16) according to claim 14, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer and an antifoaming agent.

17. A liquid crystal display element containing the liquid crystal composition according to any one of claims 9 to 16 and not having an alignment film.

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