Polymeric compound, liquid crystal composition using the same, and liquid crystal display element

Abstract

The present invention provides a polymerizable compound, a liquid crystal composition using the polymerizable compound, and a liquid crystal display element. The problem of the present invention is to provide a compound that can ensure storage stability when added to a liquid crystal composition and can achieve the homeotropic alignment of liquid crystal molecules even without providing a PI layer. In the present invention, the compound represented by formula (i) has a partial structure K represented by general formulas (K-1) to (K-18) i1 , and has at least one P-Sp group. Therefore, when used in a liquid crystal composition, it can be held in a state of adsorbing to the substrate sandwiching the liquid crystal composition (liquid crystal layer) and making the liquid crystal molecules uniaxially aligned in the horizontal direction, and can ensure the improvement of the stability of the alignment and the low-temperature storage stability.

Description

Technical Field

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

[0002] In conventional liquid crystal displays, in order to align liquid crystals, a polyimide alignment film (PI) layer is provided on an electrode. However, since the film formation of the PI layer requires a high cost, in recent years, methods for achieving the alignment of liquid crystal molecules while omitting the PI layer have been studied.

[0003] For example, Patent Document 1 discloses a liquid crystal medium characterized by being based on a mixture of polar compounds having negative dielectric anisotropy and containing at least one self-aligning additive, and describes that the liquid crystal medium is highly suitable for use in a display having no alignment layer at all. Moreover, in Patent Document 1, a specific compound having a hydroxyl group is used as a self-aligning additive in a vertical alignment (VA) mode liquid crystal display. In addition, Patent Document 2 discloses a specific compound having a polymerizable group as a self-aligning additive.

[0004] On the other hand, in in-plane switching (IPS) mode and fringe field switching (FFS) mode liquid crystal displays, an alignment additive that does not require an alignment film is also required. Therefore, an alignment additive that aligns liquid crystal molecules horizontally is needed.

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Patent Document 1: Japanese Patent Application Laid-Open No. 2014-524951

[0008] Patent Document 2: Japanese Patent Application Laid-Open No. 2015-168826 Summary of the Invention

[0009] Problems to be Solved by the Invention

[0010] However, according to the research by the present inventors, when the alignment additive described in Patent Document 2 is used, the alignment restraining force for horizontally aligning liquid crystal molecules is lacking, and the alignment unevenness and electro-optical characteristics are not sufficient.

[0011] Accordingly, an object of the present invention is to provide a polymerizable compound having a polar group, which has sufficient alignment restricting power when added to a liquid crystal composition, and can uniaxially align liquid crystal molecules uniformly in the horizontal direction without unevenness even without providing a PI layer. Further, another object of the present invention is to provide a liquid crystal composition capable of uniaxially aligning liquid crystal molecules in the horizontal direction without providing a PI layer, and a liquid crystal display device using the liquid crystal composition.

[0012] Method for solving the problem

[0013] The present invention provides a compound represented by the general formula (i).

[0014] [Chemical formula 1]

[0015]

[0016] (In the formula, R 1 and R 2 each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 40 carbon atoms, a haloalkyl group, or P-Sp-, and -CH2- in the alkyl group may be replaced by -CH=CH-, -C≡C-, -O-, -NH-, -OCOO-, -COO-, or -OCO-, provided that -O- is not consecutive, P represents a polymerizable group, and Sp represents a spacer group or a single bond.

[0017] A, C, and D each independently represent a divalent aromatic group, a divalent heteroaromatic group, a divalent aliphatic group, or a divalent heteroaliphatic group, and a hydrogen atom in these ring structures may be replaced by a halogen atom, or P-Sp-, and -Z 4 -K i1 substituted.

[0018] B represents a trivalent aromatic group.

[0019] Z 1 and Z 2 each independently represents a single bond, -CH=CH-, -CF=CF-, -C≡C-, -COO-, -OCO-, -OCOO-, -CF2O-, -OCF2-, -CH=CHCOO-, -OCOCH=CH-, -CH2-CH2COO-, -OCOCH2-CH2-, -CH=C(CH3)COO-, -OCOC(CH3)=CH-, -CH2-CH(CH3)COO-, -OCOCH(CH3)-CH2-, -OCH2CH2O-, or an alkylene group having 2 to 20 carbon atoms, and one or two or more non-adjacent -CH2- in the alkylene group may be replaced by -O-, -COO-, or -OCO-.

[0020] Z 31 and Z32 each independently represents a group selected from the following (Z3-1) to (Z3-5), or a single bond, provided that Z 31 and / or Z 32 at least one of which is any one of (Z3-1) to (Z3-5), and the black dots at both ends represent a connecting bond,

[0021] [Chemical formula 2]

[0022]

[0023] l, m and n each independently represent an integer of 0, 1, or 2,

[0024] Z 4 represents a single bond, -O-, -CH=CH-, -COO-, -OCO-, -OCOO-, -CH2-CH(CH3)COO-, -OCOCH(CH3)-CH2-, or a linear or branched alkylene group having 1 to 20 carbon atoms, and one or two or more non-adjacent -CH2- in the alkylene group may be substituted by -O-, -COO- or -OCO-,

[0025] K i1 represents a group selected from the general formulas (K-1) to (K-18),

[0026] [Chemical formula 3]

[0027]

[0028] W K1 represents a methylene group or a nitrogen atom, provided that the hydrogen atom in the methylene group may be substituted by a linear or branched alkyl group having 1 to 6 carbon atoms,

[0029] X K1 and Y K1 each independently represent -CH2-, an oxygen atom or a sulfur atom,

[0030] Z K1 represents an oxygen atom or a sulfur atom, U K1 、V K1 and S K1 each independently represent a methylene group or a nitrogen atom, T K1 each independently represents a group selected from the general formulas (T-1) to (T-6),

[0031] [Chemical formula 4]

[0032]

[0033] S T1represents a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms or a linear or branched alkenylene group having 2 to 18 carbon atoms, and -CH2- of the alkylene group or the alkenylene group can be substituted with -O-, -COO-, -C(=O)-, -C(=CH2)- or -OCO- in such a way that an oxygen atom is not directly adjacent, R T1 represents an alkyl group having 1 to 5 carbon atoms, and -CH2- of the alkyl group can be substituted with -O-, -COO-, -C(=O)-, -C(=CH2)- or -OCO- in such a way that an oxygen atom is not directly adjacent, R T2 and R T3 each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and the compound represented by the general formula (i) has at least one P-Sp group. Among A, C, D, Z 1 、Z 2 、Z 3 、Z 4 、K i1 、W K1 、X K1 、Y K1 、Z K1 、T K1 、U K1 、V K1 、S K1 、S T1 、R T1 、R T2 、R T3 、P and Sp, when there are a plurality of them, they can be the same or different.)

[0034] In addition, the present invention provides a liquid crystal composition containing one or two or more compounds represented by the general formula (i), and a liquid crystal display element using the liquid crystal composition.

[0035] Effects of the Invention

[0036] According to the present invention, it is possible to provide a polymerizable compound, a liquid crystal composition, and a liquid crystal display element using the liquid crystal composition that can achieve uniform horizontal alignment of liquid crystal molecules even without providing a PI layer, have no display unevenness, and have high reliability. In addition, compared with conventional compounds, there is less concern about a decrease in the voltage holding ratio (VHR). Detailed Embodiments

[0037] The polymerizable compound of the present embodiment is a compound represented by the general formula (i).

[0038] [Chemical Formula 5]

[0039]

[0040] Z in the general formula (i) 31and Z 32 each independently represents a group selected from the following (Z3-1) to (Z3-5) and a single bond, provided that Z 31 and / or Z 32 at least one of which is any one of (Z3-1) to (Z3-5), and the black dots at both ends represent a linking bond.

[0041] [Chemical Formula 6]

[0042]

[0043] The compound represented by the general formula (i) has a photo-functional group structure and a polar part represented by the general formula (Z3-1) to (Z3-5) in particular. Therefore, when used in a liquid crystal composition, it can be adsorbed on the substrate sandwiching the liquid crystal composition (liquid crystal layer), and can undergo dimerization or isomerization along the deflection direction by irradiating with deflected light, and can maintain the liquid crystal molecules in a horizontally aligned state. Therefore, in the liquid crystal composition using the polymerizable compound of the present embodiment, the liquid crystal molecules can be aligned even without providing a PI layer, and can be switched by applying a voltage. Thus, the compound represented by the general formula (i) is suitable for assisting the alignment of liquid crystal molecules in the liquid crystal composition. When the wavelength of the deflected light used is mainly 365 nm, as Z 31 and / or Z 32 , preferably (Z3-1), (Z3-3), (Z3-5), and when using a wavelength of 313 nm, preferably (Z3-1), (Z3-2), (Z3-4), and more preferably (Z3-1) and (Z3-2) from the viewpoints of alignment stability and reliability.

[0044] Furthermore, the present inventors have found that the polymerizable compound represented by the general formula (i) of the present embodiment not only aligns liquid crystal molecules, but also can improve the stability of the alignment property and ensure high reliability by having a partial structure represented by the general formula (K-1) to (K-18).

[0045] K in the general formula (i) i1 represents a group represented by the following general formula (K-1) to (K-18).

[0046] [Chemical Formula 7]

[0047]

[0048] In the formula, W K1 represents a methylene group or a nitrogen atom, provided that the hydrogen atom in the methylene group may be substituted by a linear or branched alkyl group having 1 to 6 carbon atoms, and X K1 and Y K1 each independently represents -CH2-, an oxygen atom or a sulfur atom, ZK1 represents an oxygen atom or a sulfur atom, U K1 , V K1 and S K1 each independently represents a methylene group or a nitrogen atom, T K1 each independently represents a group represented by the general formula (T-1) to (T-6),

[0049] [Chemical formula 8]

[0050]

[0051] S T1 represents a single bond, a linear or branched alkylene group having 1 to 15 carbon atoms or a linear or branched alkenylene group having 2 to 18 carbon atoms, and -CH2- of the alkylene group or the alkenylene group may be substituted with -O-, -COO-, -C(=O)-, -C(=CH2)- or -OCO- in such a way that an oxygen atom is not directly adjacent, R T1 represents an alkyl group having 1 to 5 carbon atoms, and -CH2- of the alkyl group may be substituted with -O-, -COO-, -C(=O)-, -C(=CH2)- or -OCO- in such a way that an oxygen atom is not directly adjacent, R T2 and R T3 each independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.

[0052] As a partial structure represented by the general formula (K-1) to (K-18), in the case of emphasizing the liquid crystal alignment property, the general formula (K-1), (K-2), (K-5), (K-8), (K-11), (K-13), (K-14), (K-15), (K-17) and (K-18) are preferred. In the case of emphasizing the reliability, (K-1), (K-9), (K-11), (K-13) and (K-15) are preferred. In consideration of balancing the alignment property and the reliability, (K-11), (K-13) and (K-15) are more preferred. In addition, in (K-13) to (K-18), T K1 is preferably a group represented by the general formula (T-1), (T-3) and (T-4), and particularly more preferably (T-1) and (T-3). S in the general formula (T-3) T1 preferably represents a single bond, a linear or branched alkylene group having 1 to 10 carbon atoms or a linear or branched alkenylene group having 2 to 10 carbon atoms, preferably a linear or branched alkyl group having 1 to 7 carbon atoms or a linear or branched alkenylene group having 2 to 7 carbon atoms, preferably a linear alkyl group having 1 to 3 carbon atoms, and -CH2- in the alkyl group or the alkylene group is preferably substituted with -O-, -C(=O)- or -C(=CH2)- in such a way that an oxygen atom is not directly adjacent. R in the general formula (T-3) T1represents a linear or branched alkyl group having 1 to 5 carbon atoms, and the -CH2- of the alkyl group is preferably substituted with -O-, -C(=O)-, -C(=CH2)- or -OCO- in such a way that the oxygen atom is not directly adjacent, and is preferably a linear alkyl group having 1 to 3 carbon atoms. In the general formula (T-3), it is preferred that at least two or more secondary carbon atoms contain -C(=O).

[0053] R in the general formula (T-6) T2 and R T3 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and preferably represent a hydrogen atom.

[0054] As preferred examples of the general formulas (K-13) to (K-17), from the viewpoints of orientation and reactivity, (K-1-1) to (K-1-4), (K-3-1), and (K-5-1) below are preferred, and particularly preferred are the formulas (K-1-1), (K-1-3), and (K-3-1).

[0055] [Chemical formula 9]

[0056]

[0057] (In the formula, P represents a polymerizable group, R T4 , R T5 and R T6 each independently represent hydrogen or an alkyl group having 1 to 3 carbon atoms, n T1 and n T2 each independently represent 0 or 1, n T3 each independently represent an integer of 0 to 3, and when there are multiple Rs T4 , R T5 , R T6 , n T1 , n T2 and n T3 can be the same or different.)

[0058] Z in the formula (i) 1 and Z 2Preferably, each represents a single bond, -CH=CH-, -CF=CF-, -C≡C-, -COO-, -OCO-, -CF2O-, -OCF2-, -CH=CHCOO-, -OCOCH=CH-, -OCH2CH2O-, or an alkylene group having 1 to 10 carbon atoms, or a group in which one or two or more non-adjacent -CH2- in the alkylene group are replaced by -O-, -COO- or -OCO-; more preferably, it represents a single bond, -COO-, -OCO-, -CH=CHCOO-, -OCOCH=CH-, -OCH2CH2O-, a linear or branched alkylene group having 1 to 6 carbon atoms, or a group in which one or two or more non-adjacent -CH2- in the alkylene group are replaced by -O-, -COO- or -OCO-, Z 1 and Z 2 More preferably, it is a single bond, -COO-, -OCO-, -OCH2CH2O-, or an alkylene group having 2 carbon atoms (ethylene (-CH2CH2-)) or a group in which one -CH2- in ethylene is replaced by -O- (-CH2O-, -OCH2-), or a group in which one -CH2- in ethylene is replaced by -COO- or -OCO- (-CH2-CH2COO-, -OCOCH2-CH2-). Z 4 represents a single bond, -O-, -CH=CH-, -COO-, -OCO-, -OCOO-, -CH2-CH(CH3)COO-, -OCOCH(CH3)-CH2-, or a linear or branched alkylene group having 1 to 20 carbon atoms (one or two or more non-adjacent -CH2- in the alkylene group may be replaced by -O-, -COO- or -OCO-); preferably, it is -COO-, -OCO-, -OCH2CH2O-, or an alkylene group having 2 carbon atoms (ethylene (-CH2CH2-)) or a group in which one -CH2- in ethylene is replaced by -O- (-CH2O-, -OCH2-), or a group in which one -CH2- in an alkyl group having 2 to 8 carbon atoms is replaced by -O-, -COO-, -OCO-.

[0059] R 1 and R 2 Preferably represents P-Sp-, a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, a haloalkyl group, in which -CH2- in the alkyl group may be replaced by -CH=CH-, -C≡C-, -O-, -COO-, -OCO- or -OCOO-, but -O- is not continuous; more preferably, it is P-Sp-, a linear or branched alkyl group having 1 to 18 carbon atoms, in which -CH2- in the alkyl group may be replaced by -CH=CH-, -O-, -OCO- (where -O- is not continuous). From the viewpoint of improving the reliability of the liquid crystal display element, R 1 and R2 Particularly preferably, it is P-Sp- and an alkyl group having 2 to 6 carbon atoms. P preferably each independently represents a substituent selected from the groups represented by the following general formulas (P-1) to (P-14). From the viewpoints of ease of operation and reactivity, formulas (P-1) and (P-2) are more preferred.

[0060] [Chemical formula 10]

[0061]

[0062] (In the formula, the black dot at the right end represents a connecting bond.)

[0063] In formula (i), Sp preferably represents a linear alkylene group having 1 to 18 carbon atoms or a single bond, more preferably represents a linear alkylene group having 2 to 15 carbon atoms or a single bond, and further preferably represents a linear alkylene group having 2 to 8 carbon atoms or a single bond. The -CH2- of this alkyl group can be substituted by -CH=CH-, -O-, -COO-, or -OCO-, and the hydrogen of -CH2- can be substituted by fluorine.

[0064] The compound represented by the general formula (i) has at least one P-Sp- group, but from the viewpoint of improving the orientation, it preferably has 2 or more or 3 or more P-Sp- groups. When there are 2 or more or 3 or more P-Sp- groups in the general formula (i), R is more preferably 2 represents a linear or branched alkyl group or haloalkyl group having 1 to 40 carbon atoms, and more preferably 2 or 3 or more P-Sp- groups are present at a position closer to R than the group selected from formulas (Z3-1) to (Z3-5) in the general formula (i). 1 side position.

[0065] Ring B in the general formula (i) is preferably a phenylene group or a naphthylene group, and more preferably a 1,2,4-phenylene triyl group or a 1,3,4-phenylene triyl group.

[0066] Rings A, C, and ring D are preferably divalent cyclic aromatic groups, divalent cyclic heteroaromatic groups, divalent cyclic aliphatic groups, or divalent cyclic heteroaliphatic groups, divalent cyclic aromatic groups, divalent cyclic heteroaromatic groups, divalent cyclic aliphatic groups, or divalent cyclic heteroaliphatic groups. Specifically, they are preferably 1,4-phenylene, 1,4-cyclohexylene, anthracene-2,6-diyl, phenanthrene-2,7-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, indane-2,5-diyl, chroman-3,7-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and 1,3-dioxane-2,5-diyl. This ring structure is preferably unsubstituted or substituted by L. substituted. L 1 substituted. L 1Preferably, it is an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, P-Sp- or Z 4 -K i1 , more preferably a group substituted with an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom. Ring A, C, and Ring D are more preferably an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a halogen atom, or 1,4-phenylene, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,4-cyclohexylene, or 1,3-diphenylene which may be substituted with P-Sp-. alkane-2,5-diyl. l, m and n represent integers of 0, 1 or 2, preferably 1+m+n≤1, preferably 1+m+n≤2, more preferably 1+m+n≤3.

[0067] More specific examples of the general formula (i) are represented by the following formulas (R-1) to (R-68), but the present invention is not limited thereto.

[0068] [Chemistry 11]

[0069]

[0070] [Chemistry 12]

[0071]

[0072] [Chemistry 13]

[0073]

[0074] [Chemistry 14]

[0075]

[0076] [Chemistry 15]

[0077]

[0078] [Chemistry 16]

[0079]

[0080] [Chemistry 17]

[0081]

[0082] [Chemistry 18]

[0083]

[0084] [Chemistry 19]

[0085]

[0086] [Chemical formula 20]

[0087]

[0088] [Chemical formula 21]

[0089]

[0090] [Chemical formula 22]

[0091]

[0092] (In the formula, R 1 , R 2 , Z 4 , K i1 each independently represents the same meaning as R 1 , R 2 , Z 4 , K i1 in general formula (i), respectively.)

[0093] As examples of more specific compounds of compound (i), they are represented by the following (P-1-1) to (P-1-60).

[0094] [Chemical formula 23]

[0095]

[0096] [Chemical formula 24]

[0097]

[0098] [Chemical formula 25]

[0099]

[0100] [Chemical formula 26]

[0101]

[0102] [Chemical formula 27]

[0103]

[0104] [Chemical formula 28]

[0105]

[0106] [Chemical formula 29]

[0107]

[0108] [Chemical formula 30]

[0109]

[0110] [Chemical Formula 31]

[0111]

[0112] [Chemical Formula 32]

[0113]

[0114] [Chemical Formula 33]

[0115]

[0116] [Chemical Formula 34]

[0117]

[0118] (Preparation Method 1) Preparation of the compound represented by the general formula (P-1-4)

[0119] An etherification reaction of 4'-bromo-2'-methoxy-[1,1'-biphenyl]-4-ol and benzyl chloride using potassium carbonate is carried out. Then, in an acetic acid solvent, hydrobromic acid is added and heated at 110 °C to obtain 4'-(benzyloxy)-4-bromo-[1,1'-biphenyl]-2-ol represented by (S-1). Then, it is obtained (S-2) by an etherification reaction of [1,1'-biphenyl]-4-ol and 5-(3-chloropropyl)-2,2-dimethyl-1,3-dioxane using potassium carbonate. Further, debenzylation is carried out by catalytic hydrogen reduction using a platinum catalyst to obtain (S-3). Further, (S-4) can be obtained by a Mizoroki-Heck reaction of (S-3) and tert-butyl acrylate using palladium acetate. Then, through an etherification reaction with 6-chlorohexyl methacrylate, and then a de-tert-butyl process using formic acid, and an acetalization reaction with acetone dimethyl acetal using p-toluenesulfonic acid as a catalyst, (S-5) is obtained. Further, through an esterification reaction of (S-5) and 3-(4-hydroxyphenyl)propyl methacrylate using a condensing agent, and a deacetalization reaction using a 10% hydrochloric acid solution, the target product (P-1-4) can be obtained.

[0120]

[0120] [Chemical Formula 35]

[0121]

[0122] (Preparation Method 2) Preparation of the compound represented by the general formula (P-1-6)

[0123] After introducing an aldehyde group through a formylation reaction of 4'-bromo-2'-fluoro[1,1'-biphenyl]-4-ol and paraformaldehyde, in the presence of a palladium catalyst, it is reacted with 2-butoxy-1,2- React with borane to obtain the phenol derivative shown in (S-6). Then, protect the phenol group with benzyl chloride to synthesize the alcohol compound shown in (S-7). Further, protect the hydroxyl group with a THP group using tetrahydro-2H-pyran to obtain the compound shown in the following (S-7). Further, reduce the aldehyde group to a hydroxyl group using sodium borohydride to obtain (S-8). By etherification with methanesulfonic acid = (2,2,5-trimethyl-1,3-dioxolan-5-yl) methyl ester using sodium hydride, the compound shown in (S-9) can be obtained. Then, perform debenzylation using a catalytic hydrogenation reaction. By esterification with 4-(3-(methacryloyloxy)propyl)cinnamic acid using a dehydrating condensing agent, (S-11) is obtained. After further removing the THP group with about 1% dilute hydrochloric acid, by esterification with methacrylic acid using a dehydrating condensing agent and deacetalization using 10% hydrochloric acid, the target product (P-1-6) can be obtained. By etherification with methanesulfonic acid = (2,2,5-trimethyl-1,3-dioxolan-5-yl) methyl ester using sodium hydride, the compound shown in (S-9) can be obtained. Then, perform debenzylation using a catalytic hydrogenation reaction. By esterification with 4-(3-(methacryloyloxy)propyl)cinnamic acid using a dehydrating condensing agent, (S-11) is obtained. After further removing the THP group with about 1% dilute hydrochloric acid, by esterification with methacrylic acid using a dehydrating condensing agent and deacetalization using 10% hydrochloric acid, the target product (P-1-6) can be obtained.

[0124] [Chemical formula 36]

[0125]

[0126] [Chemical formula 37]

[0127]

[0128] (Preparation method 3) Preparation of the compound shown in the general formula (P-1-11)

[0129] After performing the etherification reaction of 4-bromophenol and allyl chloride, heat and stir at 120 °C in a diethylaniline solvent to obtain 2-allyl-4-bromophenol shown in (S-12). After further protecting the hydroxyl group with a THP group using tetrahydro-2H-pyran, further perform the Mizoroki-Heck reaction with tert-butyl acrylate using palladium acetate to obtain (S-13). Then, after removing the THP group with about 1% dilute hydrochloric acid, perform the etherification reaction with 3-chloropropanol to obtain (S-14). Next, after adding the intermediate (S-14) and meta-chloroperbenzoic acid (m-CPBA), add tribromoacetic acid to react, and further add 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to obtain (S-15) in which the allyl part is carbonated. After further performing the esterification reaction with methacrylic acid using a dehydrating condensing agent, remove the tert-butyl group with formic acid to obtain the cinnamic acid derivative (S-16). Then, perform the esterification reaction with 5-pentylphenol using a dehydrating condensing agent to obtain the target product (P-1-11).

[0130] [Chemical formula 38]

[0131]

[0132] [Chemistry 39]

[0133]

[0134] (Preparation Method 4) Preparation of a Compound Represented by General Formula (P-1-20)

[0135] By sulfonic acid = (5-ethyl-2,2-dimethyl-1,3-di The compound shown in (S-17) is obtained by etherification reaction of methyl 2-butoxy-1,2-diol with 4-bromo-3-hydroxybenzaldehyde. The reaction proceeds with borane to obtain the alcohol derivative shown in (S-18). The THP group is then removed by Wittig reaction with 1% hydrochloric acid to obtain the diol compound shown in (S-19). Further esterification with methacrylic acid using a dehydrating condensation agent yields the target compound (P-1-20).

[0136] [Chemistry 40]

[0137]

[0138] (Liquid Crystal Composition)

[0139] When the compound represented by general formula (i) is added to a liquid crystal composition, one or more compounds represented by general formula (i) of the present invention can be added. In addition to the compound represented by general formula (i), it can further contain known polymerizable compounds, antioxidants, etc. used in liquid crystal compositions.

[0140] The content of compound (i) is preferably 0.01~50 mass %, and from the viewpoint of making liquid crystal molecules further appropriately oriented, its lower limit is preferably 0.01 mass %, 0.1 mass %, 0.5 mass %, 0.7 mass % or more, or 1 mass % or more, based on the total amount of liquid crystal composition. From the viewpoint of excellent response characteristics, the upper limit of the content of compound (i) is preferably 50 mass % or less, 30 mass % or less, 10 mass % or less, 7 mass % or less, 5 mass % or less, 4 mass % or less, or 3 mass % or less, based on the total amount of liquid crystal composition. The liquid crystal molecule used as the liquid crystal composition of the present invention can be a compound showing liquid crystal phase alone, or a compound showing liquid crystal phase when mixing two or more.

[0141] When using two or more types of liquid crystal molecules in combination, there can be multiple combinations. However, at least one type contains the following general formula (II). When the dielectric anisotropy of the liquid crystal composition is positive, it can further contain the following general formula (IIIa), (IIIb), or (IIIc). When the dielectric anisotropy of the liquid crystal composition is negative, it can contain a compound represented by the following general formula (IVa), (IVb), or (IVc).

[0142] The following shows the compound represented by the general formula (II).

[0143] [Chemical formula 41]

[0144] R 21 -M 21 -L 21 -M 22 -(L 22 -M 23 ) o -R 22 (II)

[0145] (In the formula, R 21 and R 22 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. One methylene group or two or more non-adjacent methylene groups present in these groups can be substituted with -O- or -S-. In addition, one or more hydrogen atoms present in these groups can be substituted with a fluorine atom or a chlorine atom,

[0146] M 21 、M 22 and M 23 each independently represent a group selected from the group consisting of the following groups:

[0147] (a) trans-1,4-cyclohexylene (one methylene group or two or more non-adjacent methylene groups present in this group can be substituted with -O- or -S-),

[0148] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= present in this group can be substituted with a nitrogen atom), 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, and

[0149] (c) 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-2,5-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, and 1,2,3,4-tetrahydronaphthalene-2,6-diyl

[0150] o represents 0, 1, or 2,

[0151] L21 and L 22 each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O-, -CH=CH-, -CH=N-N=CH- or -C≡C-. When there are multiple Ls 22 they may be the same or different. When there are multiple Ms 23 they may be the same or different.)

[0152] In the compound represented by the general formula (II), R 21 and R 22 each independently is preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms (including groups in which one methylene group or two or more non-adjacent methylene groups present in these groups are substituted with -O- or -S-, and groups in which one or two or more hydrogen atoms present in these groups are substituted with a fluorine atom or a chlorine atom). More preferably, it is an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 3 to 6 carbon atoms, and particularly preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.

[0153] M 21 、M 22 and M 23 each independently is preferably trans-1,4-cyclohexylene (including groups in which one CH2 group or two non-adjacent CH2 groups present in this group are substituted with an oxygen atom), 1,4-phenylene (including groups in which one or two or more CH groups present in this group are substituted with a nitrogen atom), 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl. More preferably, it is trans-1,4-cyclohexylene, 1,4-phenylene or 1,4-bicyclo[2.2.2]octylene, and particularly preferably trans-1,4-cyclohexylene or 1,4-phenylene. o is preferably 0, 1 or 2, and more preferably 0 or 1. L 21 and L 22 each independently is preferably a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O-, -CH=CH-, -CH=N-N=CH- or -C≡C-. More preferably, it is a single bond, -CH2CH2-, -(CH2)4-, -OCH2- or -CH2O-, and further preferably a single bond or -CH2CH2-.

[0154] In the structures formed by the combination of the above options, from the perspective of chemical stability, -CH=CH-CH=CH-, -C≡C-C≡C-, and -CH=CH-C≡C- are not preferred. In addition, the groups in which the hydrogen atoms in these structures are replaced by fluorine atoms are also not preferred. In addition, the structures in which oxygen atoms are bonded to each other, the structures in which sulfur atoms are bonded to each other, and the structures in which sulfur atoms are bonded to oxygen atoms are also not preferred. In addition, the structures in which nitrogen atoms are bonded to each other, the structures in which nitrogen atoms are bonded to oxygen atoms, and the structures in which nitrogen atoms are bonded to sulfur atoms are also not preferred.

[0155] If further elaborated, in the general formula (II), as specific structures, the compounds represented by the group consisting of the following general formulas (II-A) to (II-P) are preferred.

[0156] [Chemical formula 42]

[0157]

[0158] (In the formula, R 23 and R 24 each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 10 carbon atoms.)

[0159] R 23 and R 24 each independently are more preferably an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms, and further preferably an alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.

[0160] Among the compounds represented by the general formulas (II-A) to (II-P), the compounds represented by the general formulas (II-A), (II-B), (II-C), (II-E), (II-H), (II-I), (II-I), or (II-K) are preferred, and the compounds represented by the general formulas (II-A), (II-C), (II-E), (II-H), or (II-I) are further preferred.

[0161] In the present invention, it contains at least one compound represented by the general formula (II), preferably contains 1 to 10 kinds, particularly preferably contains 2 to 8 kinds. The lower limit value of the content rate of the compound represented by the general formula (II) is preferably 5% by mass, more preferably 10% by mass, further preferably 20% by mass, particularly preferably 30% by mass. As the upper limit value, it is preferably 80% by mass, further preferably 70% by mass, and further preferably 60% by mass.

[0162] When the dielectric anisotropy of the liquid crystal composition is positive, it is preferably further contained a compound selected from the group consisting of the compounds represented by the general formula (IIIa), the general formula (IIIb) and the general formula (IIIc).

[0163] [Chemical formula 43]

[0164]

[0165] (In the formula, R 31 , R 32 and R 33 independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and one methylene group or two or more non-adjacent methylene groups present in these groups may be substituted with -O- or -S-, and in addition, one or two or more hydrogen atoms present in these groups may be substituted with a fluorine atom or a chlorine atom.)

[0166] M 31 , M 32 , M 33 , M 34 , M 35 , M 36 , M 37 and M 38 independently represent a group selected from the group consisting of the following groups:

[0167] (d) trans-1,4-cyclohexylene (one methylene group or two or more non-adjacent methylene groups present in this group may be substituted with -O- or -S-),

[0168] (e) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with -N=), 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, and

[0169] (f) 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-2,5-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and decahydronaphthalene-2,6-diyl

[0170] The hydrogen atoms contained in the above group (d), group (e) or group (f) may each be substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a chlorine atom.)

[0171] L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 and L38 Each independently represents a single bond, -COO-, -OCO-, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-. In M 32 、M 34 、M 35 、M 37 、M 38 、L 31 、L 33 、L 35 、L 36 and / or L 38 When there are a plurality of them, they may be the same or different.

[0172] X 31 、X 32 、X 33 、X 34 、X 35 、X 36 and X 37 Each independently represents a hydrogen atom or a fluorine atom.

[0173] Y 31 、Y 32 and Y 33 Each independently represents a fluorine atom, a chlorine atom, a cyano group, a thiocyanato group, a trifluoromethoxy group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group or a difluoromethoxy group.

[0174] p, q, r, s and t each independently represent 0, 1 or 2, and q + r and s + t are 2 or less.).

[0175] In the compounds represented by General Formula (IIIa), General Formula (IIIb) and General Formula (IIIc), R 31 、R 32 and R 33 Each independently is preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, a linear alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms (including groups in which one methylene group or two or more non-adjacent methylene groups present in these groups are substituted with -O- or -S-, and groups in which one or two or more hydrogen atoms present in these groups are substituted with a fluorine atom or a chlorine atom).), more preferably a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and particularly preferably a linear alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.

[0176] M 31 、M 32 、M 33 、M 34 、M35 and M 36 and M 37 and M 38 are each independently preferably a trans - 1,4 - cyclohexylene group (including a group in which one or more non - adjacent methylene groups present in this group are substituted with - O - or - S -), 1,4 - phenylene group (including a group in which one - CH= or two or more non - adjacent - CH= present in this group are substituted with a nitrogen atom), 1,4 - cyclohexenylene group, 1,4 - bicyclo[2.2.2]octylene group, piperidine - 1,4 - diyl group, naphthalene - 2,6 - diyl group, 1,2,3,4 - tetrahydronaphthalene - 2,6 - diyl group, and decahydronaphthalene - 2,6 - diyl group (including a group in which each hydrogen atom in each group is substituted with a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, or a chlorine atom), more preferably a trans - 1,4 - cyclohexylene group, 1,4 - phenylene group, 3 - fluoro - 1,4 - phenylene group, or 3,5 - difluoro - 1,4 - phenylene group, still more preferably a trans - 1,4 - cyclohexylene group or 1,4 - phenylene group, and particularly preferably a trans - 1,4 - cyclohexylene group.

[0177] L 31 and L 32 and L 33 and L 34 and L 35 and L 36 and L 37 and L 38 are each independently preferably a single bond, - OCO -, - COO -, - CH2CH2 -, -(CH2)4 -, - OCH2 -, - CH2O -, - OCF2 -, - CF2O -, or - C≡C -, more preferably a single bond, - CH2CH2 -, -(CH2)4 -, or - C≡C -, and particularly preferably a single bond or - CH2CH2 -. It is preferred that X 31 and X 32 and X 33 and X 34 and X 35 and X 36 and X 37 each independently represent a hydrogen atom or a fluorine atom, and Y[[ID=4))] 31 and Y 32 and Y 33 each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a cyanothio group, a trifluoromethoxy group, a trifluoromethyl group, a 2,2,2 - trifluoroethyl group, a difluoromethoxy group, or an alkyl group having 1 to 12 carbon atoms, preferably represent a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethoxy group, a trifluoromethyl group, a 2,2,2 - trifluoroethyl group, or an alkyl group having 1 to 12 carbon atoms, and particularly preferably represent a fluorine atom. p, q, r, s, and t each independently represent 0, 1, or 2, and q + r and s + t represent 2 or less.

[0178] In the structures formed by the combination of the above options, from the perspective of chemical stability, -CH=CH-CH=CH-, -C≡C-C≡C-, and -CH=CH-C≡C- are not preferred. In addition, the groups in which the hydrogen atoms in these structures are replaced by fluorine atoms are also not preferred. In addition, the structures in which oxygen atoms are bonded to each other, the structures in which sulfur atoms are bonded to each other, and the structures in which sulfur atoms are bonded to oxygen atoms are also not preferred. In addition, the structures in which nitrogen atoms are bonded to each other, the structures in which nitrogen atoms are bonded to oxygen atoms, and the structures in which nitrogen atoms are bonded to sulfur atoms are also not preferred.

[0179] Specifically, the structure represented by the following general formula (IIIa-1) is preferred.

[0180] [Chemical formula 44]

[0181]

[0182] (In the formula, R 34 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, L 39 and L 40 each independently represent a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O-, or -C≡C-, M 38 represents 1,4-phenylene or trans-1,4-cyclohexylene, X 32 represents a hydrogen atom or a fluorine atom, p1 represents 0 or 1, Y 34 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxy group.)

[0183] More specifically, the structures represented by the following general formula (IIIa-2a) to general formula (IIIa-4d) are preferred,

[0184] [Chemical formula 45]

[0185]

[0186] [Chemical formula 46]

[0187]

[0188] [Chemical formula 47]

[0189]

[0190] (In the formula, R 34 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, X 31and X 32 each independently represents a hydrogen atom or a fluorine atom, and Y 31 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group or a trifluoromethoxy group.)

[0191] The following structures are also preferred.

[0192] [Chemical Formula 48]

[0193]

[0194] (In the formula, R 34 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and Y 31 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group or a trifluoromethoxy group.)

[0195] In the general formula (IIIb), as specific structures, the structures represented by the following general formulas are preferred.

[0196] [Chemical Formula 49]

[0197]

[0198] [Chemical Formula 50]

[0199]

[0200] [Chemical Formula 51]

[0201]

[0202] (In the formula, R 35 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, and Y 35 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group or a trifluoromethoxy group.)

[0203] In the general formula (IIIc), as specific structures, the structures represented by the following general formulas are preferred.

[0204] [Chemical Formula 52]

[0205]

[0206] [Chemical Formula 53]

[0207]

[0208] [Chemical Formula 54]

[0209]

[0210] (In the formula, R 36 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, and Y 36 represents a cyano group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxy group.)

[0211] The composition contains at least one compound selected from the group consisting of the compounds represented by the general formula (IIIa), the general formula (IIIb), and the general formula (IIIc), preferably contains 1 to 10 compounds, particularly preferably contains 2 to 8 compounds. The lower limit of the content rate of the group consisting of the compounds represented by the general formula (IIIa), the general formula (IIIb), and the general formula (IIIc) is preferably 5% by mass, more preferably 10% by mass, preferably 20% by mass, and the upper limit is preferably 80% by mass, preferably 70% by mass, preferably 60% by mass, and further preferably 50% by mass.

[0212] When the dielectric anisotropy of the liquid crystal composition is negative, it is further preferred to contain a compound selected from the group consisting of the compounds represented by the general formula (IVa), the general formula (IVb), and the general formula (IVc).

[0213] [Chemical formula 55]

[0214]

[0215] (In the formula, R 41 , R 42 , R 43 , R 44 , R 45 and R 46 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and one methylene group or two or more non-adjacent methylene groups present in these groups may be substituted with -O- or -S-, and in addition, one or two or more hydrogen atoms present in these groups may be substituted with a fluorine atom or a chlorine atom,

[0216] M 41 , M 42 , M 43 , M 44 , M 45 , M 46 , M 47 , M 48 and M 49 each independently represent a group selected from the group consisting of the following groups,

[0217] (g) trans-1,4-cyclohexylene (one methylene group or two or more non-adjacent methylene groups present in this group may be substituted with -O- or -S-),

[0218] (h) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= groups in this group may be substituted with nitrogen atoms) and

[0219] (i) 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octylene, piperidine-2,5-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl and decahydronaphthalene-2,6-diyl

[0220] The hydrogen atoms contained in the above group (g), group (h) or group (i) may each be substituted by a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a chlorine atom.

[0221] L 41 , L 42 , L 43 , L 44 , L 45 , L 46 , L 47 , L 48 and L 49 Each independently represents a single bond, -COO-, -OCO-, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-, in M 42 、M 43 、M 45 、M 46 、M 48 、M 49 , L 41 , L 43 , L 44 , L 46 , L 47 and / or L 49 When there are multiple, they can be the same or different.

[0222] X 41 、X 42 、X 43 、X 44 、X 45 、X 46 、X 47 and X 48 independently represent a hydrogen atom, a trifluoromethyl group, a trifluoromethoxy group or a fluorine atom, but X 41 and X 42 Any of represents a fluorine atom, X 43 、X 44 and X 45 Any of represents a fluorine atom, X 46 、X 47 and X 48Any one of them represents a fluorine atom, but X 46 and X 47 do not simultaneously represent fluorine atoms, X 46 and X 48 do not simultaneously represent fluorine atoms, G represents a methylene group or -O-,

[0223] u, v, w, x, y and z each independently represent 0, 1 or 2, and u + v, w + x and y + z are 2 or less.)

[0224] In addition, in the compounds represented by the general formula (IVa), the general formula (IVb) and the general formula (IVc), R 41 、R 42 、R 43 、R 44 、R 45 and R 46 each independently is preferably an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, a linear alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms (including groups in which one methylene group or two or more non-adjacent methylene groups present in these groups are substituted with -O- or -S-, and groups in which one or two or more hydrogen atoms present in these groups are substituted with fluorine atoms or chlorine atoms).), more preferably a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, and particularly preferably a linear alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms. M 41 、M 42 、M 43 、M 44 、M 45 、M 46 、M 47 、M 48 and M 49Preferred are independently trans-1,4-cyclohexylene (including groups in which one methylene group or two or more non-adjacent methylene groups in the group are substituted with -O- or -S-), 1,4-phenylene (including groups in which one -CH= or two or more non-adjacent -CH= in the group are substituted with -N=), 1,4-cyclohexenylene, 1,4-bicyclo[2.2.2]octanylene, piperidine-2,5-diyl, naphthalene-2,6-diyl, 1,2,3,4 -tetrahydronaphthalene-2,6-diyl and decahydronaphthalene-2,6-diyl groups (including groups in which hydrogen atoms contained in each group are substituted by cyano groups, fluorine atoms, trifluoromethyl groups, trifluoromethoxy groups or chlorine atoms.), more preferably trans-1,4-cyclohexylene, 1,4-phenylene, 3-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene, further preferably trans-1,4-cyclohexylene or 1,4-phenylene, and particularly preferably trans-1,4-cyclohexylene. L 41 , L 42 , L 43 , L 44 , L 45 , L 46 , L 47 , L 48 and L 49 Independently of each other, they are preferably a single bond, -CH2CH2-, -(CH2)4-, -OCO-, -COO-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-, more preferably a single bond, -CH2CH2-, -OCH2- or -CH2O-. 41 、X 42 、X 43 、X 44 、X 45 、X 46 and X 47 Each independently represents a hydrogen atom or a fluorine atom, G represents a methylene group or -O-, u, v, w, x, y and z each independently represent 0, 1 or 2, and u+v, w+x and y+z represent 2 or less.

[0225] Among the structures formed by combining the above options, -CH=CH-CH=CH-, -C≡CC≡C-, and -CH=CH-C≡C- are not preferred from the perspective of chemical stability. Furthermore, groups in which hydrogen atoms in these structures are replaced with fluorine atoms are also not preferred. Furthermore, structures in which oxygen atoms are bonded to one another, sulfur atoms are bonded to one another, and sulfur atoms and oxygen atoms are bonded are also not preferred. Furthermore, structures in which nitrogen atoms are bonded to one another, nitrogen atoms are bonded to oxygen atoms, and nitrogen atoms are bonded to sulfur atoms are also not preferred.

[0226] Among the compounds represented by the general formula (IVa), specifically, the structure represented by the following general formula (IVa-1) is preferred.

[0227] [Chemical formula 56]

[0228]

[0229] (In the formula, R 47 and R 48 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, and L 50 , L 51 and L 52 each independently represent a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O-, or -C≡C-, and M 50 represents 1,4-phenylene or trans-1,4-cyclohexylene, and u1 and v1 each independently represent 0 or 1.)

[0230] More specifically, the structures represented by the following general formulas (IVa-2a) to (IVa-3i) are preferred.

[0231] [Chemical formula 57]

[0232]

[0233] [Chemical formula 58]

[0234]

[0235] (In the formula, R 47 and R 48 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms.), R 47 and R 48 are each independently further preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.

[0236] Among the compounds represented by the general formula (IVb), specifically, the structure represented by the following general formula (IVb-1) is preferred.

[0237] [Chemical formula 59]

[0238]

[0239] (In the formula, R 49 and R 50 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, and L 52 、L53 and L 54 each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-, M 51 , M 52 and M 53 represent 1,4-phenylene or trans-1,4-cyclohexylene, w1 and x1 independently represent 0, 1 or 2, and w1 + x1 represents 2 or less.)

[0240] More specifically, it is preferably a structure represented by the following general formulas (IVb-2a) to (IVb-3f).

[0241] [Chemical formula 60]

[0242]

[0243] [Chemical formula 61]

[0244]

[0245] (In the formula, R 49 and R 50 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms.).

[0246] Among the compounds represented by the general formula (IVc), specifically, it preferably represents the structures represented by the following general formulas (IVc-1a) and (IVc-1b).

[0247] [Chemical formula 62]

[0248]

[0249] (In the formula, R 51 and R 52 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms or an alkenyl group having 2 to 8 carbon atoms, L 56 , L 57 and L 58 each independently represents a single bond, -CH2CH2-, -(CH2)4-, -OCH2-, -CH2O-, -OCF2-, -CF2O- or -C≡C-, M 54 , M 55 and M 56 represent 1,4-phenylene or trans-1,4-cyclohexylene, y1 and z1 independently represent 0, 1 or 2, and y1 + z1 represents 2 or less.)

[0250] More specifically, it is the following general formulas (IVc-2a) to (IVc-2g)

[0251] [Chemical Formula 63]

[0252]

[0253] (In the formula, R 51 and R 52 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms.)

[0254] The composition contains at least one compound selected from the group consisting of compounds represented by general formula (IIIa), general formula (IIIb), and general formula (IIIc), or compounds selected from the group consisting of compounds represented by general formula (IVa), general formula (IVb), and general formula (IVc) as a third component. Preferably, it contains 2 to 10 kinds, particularly preferably 2 to 8 kinds. The lower limit value of the content rate is preferably 5% by mass, more preferably 10% by mass, still more preferably 20% by mass, and the upper limit value is preferably 80% by mass, preferably 70% by mass, preferably 60% by mass, preferably 50% by mass.

[0255] In the liquid crystal composition of the present invention, Δn is preferably in the range of 0.08 to 0.25.

[0256] In the liquid crystal composition of the present invention, Δε can use a liquid crystal composition having positive or negative Δε according to the display mode of the liquid crystal display element. In a liquid crystal display element of the VA mode, a liquid crystal composition having negative Δε is used. At this time, Δε is preferably -1 or less, more preferably -2 or less.

[0257] The liquid crystal composition of the present invention has a wide liquid crystal phase temperature range (the absolute value of the difference between the lower limit temperature and the upper limit temperature of the liquid crystal phase), but the liquid crystal phase temperature range is preferably 100 °C or more, more preferably 120 °C or more. In addition, the upper limit temperature of the liquid crystal phase is preferably 70 °C or more, more preferably 80 °C or more. Further, the lower limit temperature of the liquid crystal phase is preferably -20 °C or less, more preferably -30 °C or less. The liquid crystal composition of the present invention may contain nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, etc. for STN liquid crystals in addition to the above compounds.

[0258] In the present invention, it may be only the polymerizable compound of the present invention, but in order to improve the orientation stability of the liquid crystal, a polymerizable liquid crystal compound having a mesogenic structure is preferably used in combination. The polymerizable compound may be a known polymerizable compound used in the liquid crystal composition. As an example of the polymerizable compound, preferably, it contains one kind or two or more kinds of compounds represented by general formula (P).

[0259] [Chemical Formula 64]

[0260]

[0261] (Where,

[0262] Z p1 represents a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkoxy group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkenyl group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms in which the hydrogen atom may be substituted by a halogen atom, or -Sp p2 -R p2 ,

[0263] R p1 and R p2 represents any one of the following formulas (RI) to (R-VIII):

[0264] [Chemistry 65]

[0265]

[0266] (Where,

[0267] With * and Sp p1 Combined,

[0268] R 2 ~R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms,

[0269] W represents a single bond, -O- or methylene,

[0270] T represents a single bond or -COO-,

[0271] p, t, and q each independently represent 0, 1, or 2.)

[0272] Sp p1 and Sp p2 represents a spacer group,

[0273] L p1 and L p2 Each independently represents a single bond, -O-, -S-, -CH2-, -OCH2-, -CH2O-, -CO-, -C2H4-, -COO-, -OCO-, -OCOOCH2-, -CH2OCOO-, -OCH2CH2O-, -CO-NR a -、-NR a -CO-, -SCH2-, -CH2S-, -CH=CR a -COO-, -CH=CR a -OCO-, -COO-CRa =CH-, -OCO-CR a =CH-, -COO-CR a =CH-COO-, -COO-CR a =CH-OCO-, -OCO-CR a =CH-COO-, -OCO-CR a =CH-OCO-, -(CH2) z -C(=O)-O-, -(CH2) z -O-(C=O)-, -O-(C=O)-(CH2) z -, -(C=O)-O-(CH2) z -, -CH2(CH3)C-C(=O)-O-, -CH2(CH3)C-O-(C=O)-, -O-(C=O)-C(CH3)CH2, -(C=O)-O-C(CH3)-CH2, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF2-, -CF2O-, -OCF2-, -CF2CH2-, -CH2CF2-, -CF2CF2- or -C≡C- (wherein, R a each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and z represents an integer of 1 to 4.).

[0274] M p2 represents 1,4-phenylene, 1,4-cyclohexylene, anthracene-2,6-diyl, phenanthrene-2,7-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, indane-2,5-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,3-di alkane-2,5-diyl or a single bond, M p2 is unsubstituted or may be substituted by an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or -R p1 substituted,

[0275] M p1 represents any one of the following formulas (i-11) to (ix-11):

[0276] [Chemical formula 66]

[0277]

[0278] (wherein, bonded to Sp with *, and bonded to L p1 with **, and bonded to L p1 , L p2 or Z p1Combination.)

[0279] M p1 Any hydrogen atom on can be replaced by an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or -R p1 substituted,

[0280] M p3 represents any one of the following formulas (i-13) to (ix-13):

[0281] [Chemical formula 67]

[0282]

[0283] (In the formula, combined with Z by *, p1 combined with L by ** p2 Combination.)

[0284] M p3 Any hydrogen atom on can be replaced by an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or -R p1 substituted,

[0285] m p2 ~m p4 each independently represents 0, 1, 2 or 3,

[0286] m p1 and m p5 each independently represents 1, 2 or 3,

[0287] In the case where there are multiple Z p1 they can be the same or different from each other. In the case where there are multiple R p1 they can be the same or different from each other. In the case where there are multiple R p2 they can be the same or different from each other. In the case where there are multiple Sp p1 they can be the same or different from each other. In the case where there are multiple Sp p2 they can be the same or different from each other. In the case where there are multiple L p1 they can be the same or different from each other. In the case where there are multiple M p2 they can be the same or different from each other.)

[0288] As specific examples of the polymeric liquid crystal compound represented by the general formula (P), they are represented by (P-2-1) to (P-2-25). Here, a and b represent integers from 2 to 10.

[0289] [Chemical Formula 68]

[0290]

[0291] [Chemical Formula 69]

[0292]

[0293] [Chemical Formula 70]

[0294]

[0295] In addition, the liquid crystal composition containing the polymeric compound of the invention of the present application polymerizes even in the absence of a photopolymerization initiator, but in order to promote polymerization, a photopolymerization initiator may be included. Examples of the photopolymerization initiator include benzoin ethers, benzophenones, acetophenones, benzil ketals, acylphosphine oxides, and the like.Particularly preferred are acetophenones and benzil ketals, and examples thereof include 1-hydroxycyclohexyl phenyl ketone “Omnirad 184”, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one “Omnirad 1173”, 2-methyl-1-[(methylthio)phenyl]-2-morpholinopropan-1-one “Omnirad 907”, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone “Omnirad 369”), 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholinophenyl)butan-1-one “Omnirad 379”, 2,2-dimethoxy-1,2-diphenylethane-1-one, bis(2,4,6-trimethylbenzoyl)-diphenylphosphine oxide “Omnirad TPO”, 2,4,6-trimethylbenzoyl-phenyl-phosphine oxide “Omnirad 819” (manufactured by IGM Resins Co., Ltd.), 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)], 2,2-dimethoxy-1,2-diphenylethane-1-one “Irgacure 651”, acetophenone “Irgacure OXE01”), 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetoxime) “Irgacure OXE02”, “Irgacure OXE04” (manufactured by BASF Co., Ltd.), “ADEKAARKLS NCI-831”, “ADEKAARKLS NCI-930”, “ADEKA ARKLS N-1919” (manufactured by ADEKA Corporation), a mixture of 2,4-diethylthioxanthone (manufactured by Nippon Kayaku Co., Ltd. “Kayacure DETX”) and ethyl p-dimethylaminobenzoate (manufactured by Nippon Kayaku Co., Ltd. “Kayacure EPA”), a mixture of isopropylthioxanthone (manufactured by Ward Blenkinsop Co., Ltd. “Quantacure-ITX”) and ethyl p-dimethylaminobenzoate, “Esacure ONE”, “Esacure KIP150”, “Esacure KIP160”, “Esacure1001M”, “Esacure A198”, “Esacure KIP IT”, “Esacure KTO46”, “Esacure TZT” (manufactured by lamberti Co., Ltd.), “Speedcure BMS”, “Speedcure PBZ”, “Benzophenone” (manufactured by LAMBSON Co., Ltd.), etc. Further, as the cationic photoinitiator, a photoacid generator can be used. As the photoacid generator, examples include diazodisulfone compounds, triphenylsulfonium compounds, phenylsulfone compounds, sulfonylpyridine compounds, triazine compounds, and diphenyliodonium. Compounds, etc.

[0296] In the liquid crystal composition of the present invention, a stabilizer may be added to improve its storage stability. Examples of usable stabilizers include hydroquinones, hydroquinone monoalkyl ethers, tert-butyl catechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, and hindered phenols and hindered amines such as those described below (AD-1) to (AD-11). The amount of stabilizer added when using the stabilizer is preferably in the range of 0.005 to 1% by mass relative to the liquid crystal composition, more preferably 0.02 to 0.5% by mass, and particularly preferably 0.03 to 0.1% by mass. The specific structure of the stabilizer is shown in the following (AD-1) to (AD-11).

[0297] [Chemistry 71]

[0298]

[0299] [Chemistry 72]

[0300]

[0301] (Liquid Crystal Display Element)

[0302] The liquid crystal composition of this embodiment is suitable for use in a liquid crystal display element. The liquid crystal display element may be an active matrix driven liquid crystal display element. The liquid crystal display element may be a PSA type, PSVA type, VA type, IPS type, FFS type, or ECB type liquid crystal display element, preferably an IPS (FFS) type liquid crystal display element.

[0303] In the liquid crystal display element of this embodiment, since a liquid crystal composition containing a compound represented by general formula (i) is used, it is not necessary to provide an alignment film such as a polyimide alignment film on the liquid crystal layer 4 side of the first substrate 2 and the second substrate 3. In other words, the liquid crystal display element of this embodiment can adopt a configuration in which at least one of the two substrates does not have an alignment film such as a polyimide alignment film.

[0304] Example

[0305] Hereinafter, the present invention will be described in more detail based on Examples, but the present invention is not limited to the Examples.

[0306] (Example 1)

[0307] 36 g of 4'-benzyloxy-4-bromo-[1,1'-biphenyl]-2-ol, (5-(bromomethyl)-2,2-dimethyl-1,3-diol) and (5-(bromomethyl)-2,2-dimethyl-1,3-diol) were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer. 30 g of (1 - (4 - (tert - butyl)phenyl)pentan - 5 - yl)methanol, 20 g of potassium carbonate, and 300 ml of N,N - dimethylformamide were reacted at 90 °C for 5 hours. After the reaction was completed, the mixture was cooled, 300 ml of ethyl acetate and 100 ml of tetrahydrofuran were added, and the organic layer was washed with water and saturated brine. The solvent was distilled off to obtain 32 g of the compound shown in (1).

[0308] [Chemical formula 73]

[0309]

[0310] Next, 32 g of the above - mentioned compound (1) was dissolved in 150 ml of tetrahydrofuran, 1 g of 5% platinum on carbon was added, and the mixture was placed in an autoclave, heated to 50 °C, and stirred for 5 hours for catalytic hydrogen reduction under a hydrogen pressure of 0.5 kPa. After the reaction was completed, the platinum on carbon was filtered off, and the solvent was distilled off. The concentrate was added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer. Further, 12 g of tert - butyl acrylate, 10 g of triethylamine, 0.6 g of palladium acetate, and 200 ml of dimethylformamide were added, and the reactor was heated to 100 °C under a nitrogen atmosphere for reaction. After the reaction was completed, ethyl acetate and THF were added, and the organic layer was washed with 2% aqueous hydrochloric acid solution, pure water, and saturated brine. After the solvent was distilled off, purification was carried out using an alumina column with 2 times the amount (weight ratio) to obtain 28.5 g of the compound shown in formula (2).

[0311] [Chemical formula 74]

[0312]

[0313] Furthermore, 28.5 g of the above - mentioned compound (2), 8.5 g of 3 - chloropropanol, 12.5 g of potassium carbonate, and 200 ml of N,N - dimethylformamide were added to a reaction vessel equipped with a stirrer, a cooler, and a thermometer and reacted at 90 °C for 5 hours. After the reaction was completed, the mixture was cooled, 300 ml of ethyl acetate and 100 ml of tetrahydrofuran were added, and the organic layer was washed with water and saturated brine. The solvent was distilled off to obtain 27 g of the compound shown in (3).

[0314] [Chemical formula 75]

[0315]

[0316] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 27 g of the above compound (3), 11 g of methacrylic acid, 1.4 g of dimethylaminopyridine, and 120 ml of dichloromethane were added. The reaction vessel was maintained at 5°C or lower using an ice-water bath, and 16 g of diisopropylcarbodiimide was slowly added dropwise under a nitrogen atmosphere. After the addition was complete, the reaction vessel was returned to room temperature and allowed to react for 5 hours. After filtering the reaction solution, 150 ml of dichloromethane was added to the filtrate, and it was washed with a 5% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After distilling off the solvent, purification was carried out using an alumina column with a two-fold amount (weight ratio), and 30.5 g of the compound represented by formula (4) was obtained.

[0317] [Chemical Formula 76]

[0318]

[0319] Then, in a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 30.5 g of the above compound (4) and 150 ml of dichloromethane were added, and 50 ml of formic acid was slowly added dropwise at room temperature. After the addition was complete, the reaction vessel was heated to 40°C and allowed to react for 1 hour. After the reaction was complete, the reaction solution was cooled to 10°C or lower, and 150 ml of pure water was slowly added. Further, 50 ml of dichloromethane was added, and the organic layer was washed with pure water, saturated sodium bicarbonate, and a 10% aqueous hydrochloric acid solution, further washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The concentrate was added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and 1.2 g of p-toluenesulfonic acid and 120 ml of acetonitrile were further added. Then, 6 g of 2,2-dimethoxypropane was slowly added dropwise at room temperature. After the addition was complete, it was allowed to react for 1 hour. After the reaction was complete, it was cooled, 200 ml of ethyl acetate and 50 ml of tetrahydrofuran were added, and the organic layer was washed with a saturated ammonium chloride solution, water, and saturated brine, and the solvent was distilled off, obtaining 24.5 g of the compound represented by formula (5).

[0320] [Chemical Formula 77]

[0321]

[0322] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 24.5 g of the above compound (5), 7.2 g of 4-pentylphenol, 0.6 g of dimethylaminopyridine, and 160 ml of dichloromethane were added. The reaction vessel was maintained at 5°C or lower using an ice-water bath, and 6 g of diisopropylcarbodiimide was slowly added dropwise under a nitrogen atmosphere. After the addition was completed, the reaction vessel was returned to room temperature and allowed to react for 5 hours. After filtering the reaction solution, 150 ml of dichloromethane was added to the filtrate, and it was washed with saturated brine, and the solvent was distilled off. Further, the concentrate was added to a reaction vessel equipped with a stirring device, and after adding 100 ml of tetrahydrofuran, 15 ml of 10% hydrochloric acid was slowly added dropwise, and the reaction was carried out at 40°C for 2 hours. After the reaction was completed, 200 ml of ethyl acetate and 50 ml of tetrahydrofuran were added, and the organic layer was washed with saturated water and saturated brine, the solvent was distilled off, and purification was carried out using a silica gel column with 2 times the amount (weight ratio), and 21 g of the target compound represented by the formula (P-1-61) was obtained.

[0323] [Chemical formula 78]

[0324]

[0325] (Example 2)

[0326] 10 g of the compound (P-1-61) of Example 1 and 100 ml of dichloromethane were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and cooled to 10°C or lower. Then, 2 g of ethyl chloroformate was slowly added dropwise. After the addition was completed, stirring was carried out for 30 minutes. Then, 1.9 g of triethylamine was added dropwise. After the reaction was completed, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification was carried out using a silica gel column, and 6 g of the target compound represented by the formula (P-1-62) was obtained.

[0327] [Chemical formula 79]

[0328]

[0329] (Example 3)

[0330] 21 g of 4'-bromo-3'-hydroxyacetophenone, 30 g of 2-(2-bromoethoxy)tetrahydro-2H-pyran, 20 g of potassium carbonate, and 300 ml of N,N-dimethylformamide were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and the reaction was carried out at 90°C for 5 hours. After the reaction was completed, it was cooled, 300 ml of ethyl acetate and 100 ml of tetrahydrofuran were added, and the organic layer was washed with water and saturated brine, and the solvent was distilled off, and 29 g of the compound represented by the formula (6) was obtained.

[0331] [Chemical formula 80]

[0332]

[0333] Next, 29 g of the above compound (6), 16 g of 4-(3-hydroxypropoxy)benzaldehyde, 27 g of barium hydroxide octahydrate, and 200 ml of methanol were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and the reaction was carried out at 45 °C for 6 hours. After completion of the reaction, a saturated ammonium chloride solution, 300 ml of ethyl acetate, and 100 ml of tetrahydrofuran were added, and the organic layer was washed with water and saturated brine, and the solvent was distilled off to obtain 33 g of the compound represented by the formula (7).

[0334] [Chemical formula 81]

[0335]

[0336] 33 g of the above compound (7), 18 g of 2-butoxy-1,2- borane, 13 g of potassium carbonate, 0.7 g of triethylamine, 1.2 g of palladium(II) chloride, 6.2 g of 2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl, and 100 ml of tetrahydrofuran were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and the reaction was carried out at 70 °C for 10 hours. After completion of the reaction, the reaction mixture was cooled, 200 ml of ethyl acetate was added, and the organic layer was washed with water and saturated brine. After distilling off the solvent, purification was carried out using an alumina column to obtain 21 g of the compound represented by the formula (8).

[0337] [Chemical formula 82]

[0338]

[0339] 21 g of the above compound (8), 7.4 g of methacrylic acid, 0.6 g of dimethylaminopyridine, and 160 ml of dichloromethane were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer. The reaction vessel was maintained at 5 °C or lower using an ice-water bath, and 13 g of diisopropylcarbodiimide was slowly added dropwise under a nitrogen atmosphere. After completion of the dropwise addition, the reaction vessel was returned to room temperature and allowed to react for 5 hours. After filtering the reaction solution, 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with saturated brine, and the solvent was distilled off. Further, the concentrate was added to a reaction vessel equipped with a stirring device, 100 ml of tetrahydrofuran and 10 ml of methanol were added, and then 15 ml of 1% hydrochloric acid was slowly added dropwise and allowed to react for 2 hours. After completion of the reaction, 200 ml of ethyl acetate and 50 ml of tetrahydrofuran were added, and the organic layer was washed with saturated water and saturated brine, and the solvent was distilled off. Purification was carried out using a silica gel column with a two-fold amount (weight ratio) to obtain 21 g of the target compound represented by the formula (P-1-63).

[0340] [Chemical formula 83]

[0341]

[0342] (Example 4)

[0343] 21 g of 4'-bromo-3'-hydroxyacetophenone, methanesulfonic acid = (2,2-dimethyl-1,3-diol) 25 g of methyl ester (4-(2-(2-(2-(2-(4-(2-alkyl-4-yl)methyl)propane) ester), 20 g of potassium carbonate, and 300 ml of N,N-dimethylformamide were reacted at 90°C for 5 hours. After the reaction, the mixture was cooled, 300 ml of ethyl acetate and 100 ml of tetrahydrofuran were added, the organic layer was washed with water and saturated brine, and the solvent was distilled off to obtain 29 g of the compound represented by formula (6).

[0344] [Chemistry 84]

[0345]

[0346] Next, by the same method as in Example 3, 21 g of the target compound represented by formula (P-1-64) was obtained.

[0347] [Chemistry 85]

[0348]

[0349] (Example 5)

[0350] 36 g of 4'-benzyloxy-4-bromo-[1,1'-biphenyl]-2-ol, 2,3-dimethyl-1,3-diol and 2,2,2-trimethyl-1,3-diol were added to a reaction vessel equipped with a stirrer, a cooler and a thermometer. 21 g of methyl ester (5-hydroxy-2-methyl-1-thiazolin-1-yl) ester, 20 g of potassium carbonate, and 300 ml of N,N-dimethylformamide were reacted at 90°C for 5 hours. After the reaction, the mixture was cooled, 300 ml of ethyl acetate and 100 ml of tetrahydrofuran were added, and the organic layer was washed with water and saturated brine. The solvent was distilled off to obtain 28.5 g of the compound represented by (10).

[0351] [Chemistry 86]

[0352]

[0353] Next, 28.5 g of the above compound (10) was dissolved in 150 ml of tetrahydrofuran, 1 g of 5% platinum-carbon was added, and the mixture was added to an autoclave, heated to 50 °C, stirred for 5 hours, and subjected to catalytic hydrogen reduction under a hydrogen pressure of 0.5 kPa. After the reaction was completed, the platinum-carbon was filtered off, and the solvent was distilled off. The concentrate was added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer. Further, 11 g of tert-butyl acrylate, 9 g of triethylamine, 0.6 g of palladium acetate, and 200 ml of dimethylformamide were added, and the reactor was heated to 100 °C under a nitrogen atmosphere to carry out the reaction. After the reaction was completed, ethyl acetate and THF were added, and the organic layer was washed with a 2% aqueous hydrochloric acid solution, pure water, and saturated brine. After the solvent was distilled off, purification was carried out using an alumina column with a two-fold amount (weight ratio), and 20 g of the compound represented by the formula (11) was obtained.

[0354] [Chemical formula 87]

[0355]

[0356] Further, 20 g of the above compound (11), 8.5 g of 3-chloropropanol, 12.5 g of potassium carbonate, and 200 ml of N,N-dimethylformamide were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and the reaction was carried out at 90 °C for 5 hours. After the reaction was completed, the mixture was cooled, 300 ml of ethyl acetate and 100 ml of tetrahydrofuran were added, the organic layer was washed with water and saturated brine, and the solvent was distilled off to obtain 20.5 g of the compound represented by (12).

[0357] [Chemical formula 88]

[0358]

[0359] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 20.5 g of the above compound (12), 6 g of methacrylic acid, 0.6 g of dimethylaminopyridine, and 60 ml of dichloromethane were added, and the reaction vessel was maintained at 5 °C or lower using an ice-water bath. Under a nitrogen atmosphere, 8.5 g of diisopropylcarbodiimide was slowly added dropwise. After the addition was completed, the reaction vessel was restored to room temperature and allowed to react for 5 hours. After the reaction solution was filtered, 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with a 5% aqueous hydrochloric acid solution and further washed with saturated brine. The organic layer was dried using anhydrous sodium sulfate. After the solvent was distilled off, purification was carried out using an alumina column with a two-fold amount (weight ratio), and 22 g of the compound represented by the formula (13) was obtained.

[0360] [Chemical formula 89]

[0361]

[0362] Then, in a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 22 g of the above compound (13), 120 ml of dichloromethane were added, and 50 ml of formic acid was slowly added dropwise at room temperature. After the addition was completed, the reaction vessel was heated to 40 °C and allowed to react for 1 hour. After the reaction was completed, the reaction solution was cooled to below 10 °C, and 150 ml of pure water was slowly added. Further, 50 ml of dichloromethane was added, and the organic layer was washed with pure water, saturated sodium bicarbonate, and 10% aqueous hydrochloric acid solution, and further washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The concentrate was added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and 1 g of p-toluenesulfonic acid and 120 ml of acetonitrile were further added. Then, 3 g of 2,2-dimethoxypropane was slowly added dropwise at room temperature. After the addition was completed, it was allowed to react for 1 hour. After the reaction was completed, it was cooled, 200 ml of ethyl acetate and 50 ml of tetrahydrofuran were added, and the organic layer was washed with saturated ammonium chloride solution, water, and saturated brine, and the solvent was distilled off to obtain 18.5 g of the compound represented by the formula (14).

[0363] [Chemical formula 90]

[0364]

[0365] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 18.5 g of the above compound (14), 3.3 g of 1-methoxyethanol, 0.4 g of dimethylaminopyridine, and 60 ml of dichloromethane were added. The reaction vessel was maintained at below 5 °C using an ice-water bath, and 5.3 g of diisopropylcarbodiimide was slowly added dropwise under a nitrogen atmosphere. After the addition was completed, the reaction vessel was returned to room temperature and allowed to react for 5 hours. After the reaction solution was filtered, 150 ml of dichloromethane was added to the filtrate, and it was washed with saturated brine, and the solvent was distilled off. Further, the concentrate was added to a reaction vessel equipped with a stirring device, and after adding 100 ml of tetrahydrofuran, 15 ml of 10% hydrochloric acid was slowly added dropwise, and it was allowed to react at 40 °C for 2 hours. After the reaction was completed, 200 ml of ethyl acetate and 50 ml of tetrahydrofuran were added, and the organic layer was washed with saturated water and saturated brine, and the solvent was distilled off. It was purified using a silica gel column with 2 times the amount (weight ratio), and 12 g of the target compound represented by the formula (P-1-65) was obtained.

[0366] [Chemical formula 91]

[0367]

[0368] (Example 6)

[0369] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 21 g of 2-hydroxy-5-((tetrahydrofuran-2-yl)oxy)benzaldehyde, 33 g of 4-(6-(benzyloxy)hexyloxy)benzoic acid, 1.2 g of dimethylaminopyridine, and 250 ml of dichloromethane were added. The reaction vessel was maintained at below 5 °C using an ice-water bath, and 15 g of diisopropylcarbodiimide was slowly added dropwise under a nitrogen atmosphere. After the addition was completed, the reaction vessel was returned to room temperature and allowed to react for 5 hours. After filtering the reaction solution, 200 ml of dichloromethane was added to the filtrate, and it was washed with saturated brine. The solvent was distilled off. Further purification was carried out using an alumina column with a two-fold amount (weight ratio), and 45 g of the compound shown in formula (15) was obtained.

[0370] [Chemical Formula 92]

[0371]

[0372] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 1.5 g of sodium borohydride and 20 ml of ethanol were added. While maintaining the reaction vessel at below 5 °C using an ice-water bath, 100 ml of a tetrahydrofuran solution of 45 g of the above compound (15) was slowly added dropwise. After the addition was completed, the reaction vessel was returned to room temperature and allowed to react for 1 hour. After the reaction was completed, 150 ml of saturated ammonium chloride solution was slowly added, and the organic layer was extracted with 200 ml of ethyl acetate. After washing with water and saturated brine, the solvent was distilled off, and 42 g of the compound shown in formula (16) was obtained.

[0373] [Chemical Formula 93]

[0374]

[0375] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 6 g of sodium hydride and 100 ml of N,N-dimethylformamide were added. While maintaining the reaction vessel at below 5 °C using an ice-water bath, 80 ml of a tetrahydrofuran solution of 42 g of the above compound (16) was slowly added dropwise. After the addition was completed, the reaction vessel was returned to room temperature, and 50 ml of a tetrahydrofuran solution of 24 g of methyl (2,2,2-trimethyl-1,3-dioxolan-5-yl)methanesulfonate was slowly added dropwise to allow the reaction to proceed. After the addition was completed, the reaction vessel was heated to 50 °C and further allowed to react for 3 hours. After completion, 150 ml of saturated ammonium chloride solution was slowly added, and the organic layer was extracted with 300 ml of ethyl acetate. After washing with water and saturated brine, the solvent was distilled off, and 38 g of the compound shown in formula (17) was obtained. In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 6 g of sodium hydride and 100 ml of N,N-dimethylformamide were added. While maintaining the reaction vessel at below 5 °C using an ice-water bath, 80 ml of a tetrahydrofuran solution of 42 g of the above compound (16) was slowly added dropwise. After the addition was completed, the reaction vessel was returned to room temperature, and 50 ml of a tetrahydrofuran solution of 24 g of methyl (2,2,2-trimethyl-1,3-dioxolan-5-yl)methanesulfonate was slowly added dropwise to allow the reaction to proceed. After the addition was completed, the reaction vessel was heated to 50 °C and further allowed to react for 3 hours. After completion, 150 ml of saturated ammonium chloride solution was slowly added, and the organic layer was extracted with 300 ml of ethyl acetate. After washing with water and saturated brine, the solvent was distilled off, and 38 g of the compound shown in formula (17) was obtained.

[0376] [Chemical Formula 94]

[0377]

[0378] Next, 38 g of the above compound (17) was dissolved in 150 ml of tetrahydrofuran, 2 g of 5% palladium-carbon was added, and the mixture was placed in an autoclave, heated to 50 °C, stirred for 5 hours, and subjected to catalytic hydrogen reduction under a hydrogen pressure of 0.5 kPa. After the reaction was completed, the palladium-carbon was filtered off, and the solvent was distilled off. The concentrate was added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 6.5 g of methacrylic acid, 0.6 g of dimethylaminopyridine, and 150 ml of dichloromethane were added, and the reaction vessel was maintained at 5 °C or lower using an ice-water bath. Under a nitrogen atmosphere, 9 g of diisopropylcarbodiimide was slowly added dropwise. After the addition was completed, the reaction vessel was returned to room temperature and allowed to react for 5 hours. After the reaction solution was filtered, 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, the concentrate was added to a reaction vessel equipped with a stirring device, 100 ml of tetrahydrofuran and 10 ml of methanol were added, and then 15 ml of 1% hydrochloric acid was slowly added dropwise, and the mixture was allowed to react for 2 hours. After the reaction was completed, 200 ml of ethyl acetate and 50 ml of tetrahydrofuran were added, and the organic layer was washed with saturated water and saturated brine, the solvent was distilled off, and the product was purified using an alumina column with 2 times the amount (weight ratio) of alumina to obtain 21 g of the compound shown by the formula (18).

[0379] [Chemical Formula 95]

[0380]

[0381] 21 g of the above compound (18), 11 g of (E)-3-(4-(3-methacryloyloxy)propoxy)phenyl)acrylic acid, 0.6 g of dimethylaminopyridine, and 150 ml of dichloromethane were added to a reaction vessel equipped with a stirring device, a cooler, and a thermometer, and the reaction vessel was maintained at 5 °C or lower using an ice-water bath. Under a nitrogen atmosphere, 6 g of diisopropylcarbodiimide was slowly added dropwise. After the addition was completed, the reaction vessel was returned to room temperature and allowed to react for 5 hours. After the reaction solution was filtered, 150 ml of dichloromethane was added to the filtrate, and the mixture was washed with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off, and the product was purified using an alumina column to obtain 35 g of the compound shown by the formula (19).

[0382] [Chemical Formula 96]

[0383]

[0384] 35 g of the above compound (19) was added to a reaction vessel equipped with a stirring device. After adding 150 ml of tetrahydrofuran, 15 ml of 10% hydrochloric acid was slowly added dropwise, and the reaction was carried out at 40 °C for 2 hours. After the reaction was completed, 200 ml of ethyl acetate and 50 ml of tetrahydrofuran were added, and the organic layer was washed with saturated water and saturated brine, and the solvent was distilled off. Then, the concentrate was added to a reaction vessel equipped with a stirring device, a cooler and a thermometer, 11 g of triethylamine was added, and the reaction vessel was maintained at 5 °C or lower using an ice-water bath. Under a nitrogen atmosphere, 11.4 g of methylmalonyl chloride was slowly added dropwise. After the addition was completed, the reaction vessel was returned to room temperature and the reaction was carried out for 5 hours. After filtering the reaction solution, 150 ml of dichloromethane was added to the filtrate, and it was washed with water and saturated brine, and the organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, and purification was carried out using a silica gel column with 2 times the amount (weight ratio), and 29 g of the target compound represented by the formula (P-1-66) was obtained.

[0385] [Chemical formula 97]

[0386]

[0387] (Example 7)

[0388] A composition composed of the following compounds and mixing ratios:

[0389] [Chemical formula 98]

[0390]

[0391] 0.3 parts by mass of the following polymerizable compound (P-2-8) was added to 100 parts by mass of the above liquid crystal composition LC-1 to prepare a composition (LC-1).

[0392] [Chemical formula 99]

[0393]

[0394] Furthermore, 0.6 parts by mass of the compound (P-1-61) synthesized in Example 1 was added to 100 parts by mass of (LC-1) to prepare a liquid crystal composition (LC-1M1). The storage stability of this composition was excellent, and no precipitation was observed even at -20 °C (for 48 hours). Then, the following evaluation tests were carried out on the liquid crystal composition (LC-1M1).

[0395] (Evaluation test of horizontal alignment)

[0396] A first substrate (common electrode substrate) without an alignment film having a transparent electrode layer formed of a transparent common electrode and a color filter layer, and a second substrate (pixel electrode substrate) without an alignment film having a pixel electrode layer with a transparent pixel electrode driven by an active element are fabricated. On the sides of these first and second substrates that are in contact with the liquid crystal layer, ozone treatment is performed for 30 seconds respectively. A liquid crystal composition is dropped onto the first substrate, clamped onto the second substrate, and a sealant is cured at 110 °C for 2 hours under normal pressure to obtain a liquid crystal cell with a cell gap of 3.2 μm.

[0397] Furthermore, heating is performed to bring the obtained liquid crystal cell to a temperature of 100 °C, and at this temperature, linearly polarized UV light with an illuminance of 100 m / cm when irradiated at 365 nm is irradiated for 200 seconds. 2 At this time, a high-pressure mercury lamp is used as the light source, and linearly polarized UV is irradiated through a wire grid.

[0398] A polarizing microscope is used to observe the alignment property and alignment unevenness such as drop marks at this time, and evaluation is performed using the following 5 grades.

[0399] A: Uniaxial horizontal alignment is uniformly performed over the entire surface, including the ends.

[0400] B: The level at which alignment defects are observed very rarely.

[0401] C: Alignment defects are observed, but at an acceptable level.

[0402] D: Including the ends, there are many alignment defects and it is at an unacceptable level.

[0403] E: The alignment is quite poor.

[0404] (Evaluation test of the residual monomer amount)

[0405] For the cell used in the above (evaluation test of horizontal alignment property), after further irradiating with a UV fluorescent lamp manufactured by Toshiba Lightech for 120 minutes (the illuminance at 313 nm is 1.7 mW / cm 2 ), the residual amount of the polymerizable compound (P-1-61) is quantified by HPLC to determine the residual monomer amount. Based on the residual amount of the monomer, evaluation is performed using the following 4 grades.

[0406] A: Less than 30 ppm

[0407] B: 30 ppm or more and less than 50 ppm

[0408] C: 50 ppm or more and less than 200 ppm

[0409] D: 200 ppm or more

[0410] (Evaluation test of voltage holding ratio)

[0411] For the cells fabricated by performing the same processes as those in the above (evaluation test of residual monomer amount), the voltage holding ratio (VHR) (%) at 333 K was measured under the conditions of a frequency of 0.6 Hz and an applied voltage of 1 V. The device used was LCM-2 manufactured by Tokuyo Technica Co., Ltd., and the evaluation was carried out in the following 4 grades.

[0412] A: 98.0% or more

[0413] B: 95.0% or more and less than 98.0%

[0414] C: 75.0% or more and less than 95.0%

[0415] D: 75.0% or less

[0416] The results of the evaluation test of the horizontal alignment property showed a uniform horizontal alignment (level A). In the evaluation test of the residual monomer amount, the residual amount was less than 30 ppm (level A). Further, the VHR of the cell was 97% (level B), which was a good result.

[0417] (Example 8)

[0418] To 100 parts by mass of the liquid crystal composition (LC-1), 0.6 part by mass of the compound represented by the compound (P-1-62) synthesized in Example 2 was added to prepare a liquid crystal composition (LC-1M2). The storage stability of this composition was excellent, and no precipitation was observed even at -20 °C (for 48 hours). Next, the same evaluation tests as those in Example 7 were carried out on the liquid crystal composition (LC-1M2). The results of the evaluation test of the horizontal alignment property showed a level where alignment defects were slightly observed (level B). Regarding the residual monomer amount, the residual amount was less than 30 ppm (level A). Further, the VHR of the cell was 95% (level B), which was a good result.

[0419] (Example 9) Adjustment of liquid crystal composition

[0420] With respect to 100 parts by mass of the liquid crystal composition (LC-1), 0.6 part by mass of the compound represented by the compound (P-1-63) synthesized in Example 3 was added to prepare a liquid crystal composition (LC-1M3). The storage stability of this composition was excellent, and no precipitation was observed even at -20 °C (for 48 hours). Subsequently, the same evaluation test as in Example 7 was conducted on the liquid crystal composition (LC-1M3). The results of the evaluation test for the horizontal alignment showed an acceptable level (Level C) although alignment defects were observed. Regarding the amount of residual monomer, the residual amount was less than 50 ppm (Level B). Further, the VHR of this cell was 97% (Level B), which was a good result.

[0421] (Example 10) Adjustment of Liquid Crystal Composition

[0422] With respect to 100 parts by mass of the liquid crystal composition (LC-1), 0.6 part by mass of the compound represented by the compound (P-1-64) synthesized in Example 4 was added to prepare a liquid crystal composition (LC-1M4). The storage stability of this composition was excellent, and no precipitation was observed even at -20 °C (for 48 hours). Subsequently, the same evaluation test as in Example 7 was conducted on the liquid crystal composition (LC-1M4). The results of the evaluation test for the horizontal alignment showed a level where alignment defects were slightly observed (Level B). Regarding the amount of residual monomer, the residual amount was less than 50 ppm (Level B). Further, the VHR of this cell was 96% (Level B), which was a good result.

[0423] (Example 11) Adjustment of Liquid Crystal Composition

[0424] With respect to 100 parts by mass of the liquid crystal composition (LC-1), 0.6 part by mass of the compound represented by the compound (P-1-65) synthesized in Example 5 was added to prepare a liquid crystal composition (LC-1M5). The storage stability of this composition was excellent, and no precipitation was observed even at -20 °C (for 48 hours). Subsequently, the same evaluation test as in Example 7 was conducted on the liquid crystal composition (LC-1M5). The results of the evaluation test for the horizontal alignment showed a uniform alignment (Level A). Regarding the amount of residual monomer, the residual amount was less than 50 ppm (Level B). Further, the VHR of this cell was 98% (Level A), which was a good result.

[0425] (Example 12) Adjustment of Liquid Crystal Composition

[0426] With respect to 100 parts by mass of the liquid crystal composition (LC-1), 0.6 part by mass of the compound represented by the compound (P-1-66) synthesized in Example 6 was added to prepare a liquid crystal composition (LC-1M6). The storage stability of this composition was excellent, and no precipitation was observed even at -20 °C (for 48 hours). Subsequently, the same evaluation test as in Example 7 was conducted on the liquid crystal composition (LC-1M6). The result of the evaluation test for the horizontal alignment showed a level (Level B) where alignment defects were slightly observed. Regarding the amount of residual monomers, the residual amount was less than 30 ppm (Level A). Further, the VHR of this cell was 98% (Level A), which was a good result.

[0427] (Comparative Example 1)

[0428] With respect to 100 parts by mass of the liquid crystal composition (LC-1), 0.6 part by mass of the compound represented by the following compound (P-1-67) was added to prepare a liquid crystal composition (LC-1M7). The storage stability of this composition was excellent, and precipitation was observed at -20 °C (for 48 hours). Subsequently, the same evaluation test as in Example 7 was conducted on the liquid crystal composition (LC-1M7). The result of the evaluation test for the horizontal alignment was D: extremely poor alignment (Level D). Regarding the amount of residual monomers, the residual amount was 50 ppm or more (Level C). Further, the VHR of this cell was 93% (Level C).

[0429] [Chemical Formula 100]

[0430]

Claims

1. A compound represented by the general formula (i), wherein, R 1 represents P-Sp-, R 2 represents a straight-chain or branched-chain alkyl group, a haloalkyl group, or P-Sp- having 1 to 40 carbon atoms, in which -CH2- in the alkyl group may be replaced by -CH=CH-, -C≡C-, -O-, -NH-, -OCOO-, -COO- or -OCO-, provided that -O- is not consecutive. P represents a substituent selected from the group represented by the following general formulas P-1, P-2, P-3, P-5, P-6, P-8, P-13, and P-14, The black dot at the right end represents a connecting bond, Sp represents a straight-chain alkyl group having 1 to 18 carbon atoms or a single bond, and -CH2- in the alkyl group may be substituted by -CH=CH-, -O-, -COO-, or -OCO-, and the hydrogen of -CH2- may be substituted by fluorine, A, C, and D each independently represent a ring structure selected from 1,4-phenylene, 1,4-cyclohexylene, phenanthrene-2,7-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, indane-2,5-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and 1,3-dioxane-2,5-diyl, and the ring structure represents an unsubstituted group or may be substituted by an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or a P-Sp-substituted group, wherein the ring structure represents an unsubstituted group or may be substituted by an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or a P-Sp-substituted group, B represents a phenylene group or a naphthylene group, Z 1 and Z 2 each independently represents a single bond, -COO-, -OCO-, -OCOO-, -CH2-CH2COO-, -OCOCH2-CH2-, -CH2-CH(CH3)COO-, -OCOCH(CH3)-CH2-, -OCH2CH2O- or an alkylene group having 2 to 20 carbon atoms, and one or two or more non-adjacent -CH2- in the alkylene group may be substituted with -O-, -COO- or -OCO- Z 31 and Z 32 each independently represents a group selected from the following formulas (Z3-1) to (Z3-2), or a single bond, provided that Z 31 and / or Z 32 at least one of which is any one of (Z3-1) to (Z3-2), and the black dots at both ends represent connecting bonds, l, m, and n each independently represent an integer of 0, 1, or 2, l + m + n is less than or equal to 3, and when n is 0, Z 31 is any one of (Z3 - 1) to (Z3 - 2), Z 4 represents a single bond, -O-, -COO-, -OCO-, -OCOO-, or a straight-chain or branched alkylene group having 1 to 20 carbon atoms, and one or two or more non-adjacent -CH2- groups in the alkylene group may be replaced by -O-, -COO- or -OCO- K i1 represents a selection from the general formula (K-11), X K1 and Y K1 each independently represents an oxygen atom, Z K1 represents an oxygen atom, The compound represented by the general formula (i) has at least one P-Sp group, and when there are multiple A, C, D, Z 1 , Z 2 , Z 4 , K i1 , X K1 , Y K1 , Z K1 , P and Sp, they may be the same or different.

2. A liquid crystal composition containing the compound represented by the general formula (i) according to claim 1, other polymerizable compounds different from the compound represented by the general formula (i), and a non-polymerizable liquid crystal compound.

3. A liquid crystal display element using the liquid crystal composition according to claim 2, and at least one of the two substrates does not have an alignment film.

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