Polymeric compound and liquid crystal composition using the same

Abstract

The present invention provides a polymerizable compound and a liquid crystal composition using the same. The problem to be solved by the present invention is to provide a polymerizable compound having a sufficiently fast polymerization rate and capable of forming a pretilt angle within a shorter ultraviolet irradiation time. In addition, the problem to be solved by the present invention is to provide a polymerizable compound for manufacturing a PS type or PSVA type liquid crystal display element having little or no display defect caused by a change in the pretilt angle, having a sufficient pretilt angle, and excellent response performance, and to provide a liquid crystal composition containing the polymerizable compound. The present invention provides a compound having a structure represented by the general formula (Y), and provides a liquid crystal composition containing the compound and an element using the liquid crystal composition. [Chemical formula 1]

Description

Technical Field

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

[0002] Regarding liquid crystal display elements using a liquid crystal composition having a negative dielectric anisotropy Δη, PSA and PSVA type liquid crystal TVs, liquid crystal monitors, etc. have become widespread. As liquid crystal compositions suitable for such liquid crystal display elements, Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, Patent Document 5, etc. have disclosed various polymerizable compounds and liquid crystal compositions containing the same.

[0003] However, in terms of the characteristics of the conventional liquid crystal compositions containing polymerizable compounds, they are insufficient for high-definition liquid crystal TVs such as 4K and 8K. Specifically, 4K and 8K liquid crystal display elements require high-definition pixels, and a considerable amount of UV light is filtered out by increasing the area of wirings and light-shielding portions. Therefore, in the UV irradiation process in the manufacture of PSA and PSVA type liquid crystal display elements, the polymerizable compounds are not sufficiently polymerized, and a large amount of polymerizable compounds remain. As a result, the following situations have been confirmed: the formation of tilt angles becomes insufficient, deterioration of the response speed and deterioration of the alignment property lead to afterimages, and in addition, the remaining polymerizable compounds slowly polymerize during driving and the tilt angle changes, resulting in display defects such as image sticking (IS).

[0004] In view of the above circumstances, for PSA or PSVA type liquid crystal display elements such as high-definition liquid crystal TVs and liquid crystal monitors, extremely high characteristics that are significantly different from the prior art are required, and a liquid crystal composition that can be stably manufactured with weaker or less UV light than in the past is required.

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2016-216747

[0008] Patent Document 2: Japanese Patent No. 4803320

[0009] Patent Document 3: Japanese Patent No. 6008065

[0010] Patent Document 4: Japanese Patent No. 6233550

[0011] Patent Document 5: Japanese Patent No. 5743132 Summary of the Invention

[0012] Problems to be Solved by the Invention

[0013] The problem to be solved by the present invention is to provide a polymerizable compound with a sufficiently fast polymerization rate and capable of forming a pretilt angle within a shorter ultraviolet irradiation time. In addition, the problem to be solved by the present invention is to provide a polymerizable compound for manufacturing a PS-type or PSVA-type liquid crystal display element with little or no display defect caused by the change of the pretilt angle, having a sufficient pretilt angle and excellent response performance, and to provide a liquid crystal composition containing the polymerizable compound.

[0014] Means for solving the problem

[0015] The inventors of the present application have conducted intensive research to solve the above problems, and as a result, the present application invention has been completed.

[0016] That is, the present invention provides a compound represented by the general formula (Y), and also provides a liquid crystal composition and a display element containing the compound.

[0017] [Chemical formula 1]

[0018]

[0019] (In the formula,

[0020] R y1 and R y2 each independently represents a linear or branched alkyl group having 1 to 30 carbon atoms, in which a hydrogen atom of the alkyl group may be substituted with a halogen atom, a cyano group or a nitro group, and -CH 2 - in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent continuously.

[0021] S y1 and S y2 each independently represents a single bond or an alkylene group having 1 to 12 carbon atoms, in which a hydrogen atom of the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and -CH 2 - in the alkylene group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent continuously.

[0022] Z y1 and Z y2 each independently represents a single bond, -C 2 H 4 -, -C 4 H 8 -, -C 3 H 6 -, -OCH 2 -, -CH 2O-, -CO-, -COO-, -OCO-, -OCOOCH 2 -, -CH 2 OCOO-, -OCH 2 CH 2 O-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COO-CRa=CH-COO-, -COO-CRa=CH-OCO-, -OCO-CRa=CH-COO-, -OCO-CRa=CH-OCO-, -COOC 2 H 4 -, -OCOC 2 H 4 -, -C 2 H 4 OCO-, -CH 2 OCO-, -COOCH 2 -, -OCOCH 2 -, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF 2 O-, -OCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - or -C≡C- (wherein, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),

[0023] M y1 and M y2 each independently represents a divalent aromatic group, a divalent cycloaliphatic group, a divalent heterocyclic compound group, a divalent condensed ring or a divalent condensed polycycle, and the hydrogen atoms in these ring structures may be substituted by L y1 substituted, L y1 represents a halogen atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 30 carbon atoms, and the hydrogen atoms in the alkyl group may be substituted by a halogen atom, a cyano group or a nitro group, and the -CH 2 - in the alkyl group may be substituted by -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be consecutive and adjacent, and m and n independently represent integers from 0 to 3, where the sum of m + n is 1 to 6,

[0024] P y1 and P y2 represent a polymerizable group.)

[0025] Effects of the Invention

[0026] Regarding the polymerizable compound of the present invention, the polymerization rate of the polymerizable compound and the formation of the pretilt angle are sufficiently fast, the compatibility with the liquid crystal composition is high, the storage stability and long-term reliability of the liquid crystal composition are not impaired, and it can be easily manufactured. If a liquid crystal composition using the polymerizable compound of the present invention is used, a liquid crystal display element that exhibits excellent display quality for a long time can be provided. Detailed Description of the Invention

[0027] The polymerizable initiator compound represented by the general formula (Y) in the present invention is characterized by having a polymerizable group and a β-dicarbonyl skeleton. Here, in this specification, an initiator compound having a polymerizable group in the initiator compound is referred to as a "polymerizable initiator compound", and an initiator compound not having a polymerizable group is referred to as a "non-polymerizable initiator compound" for distinction. In addition, an initiator compound having a β-dicarbonyl skeleton in the molecular structure of the initiator compound is referred to as a "β-dicarbonyl-based initiator compound", and an initiator compound not having a β-dicarbonyl skeleton is referred to as a "non-β-dicarbonyl-based initiator compound" for distinction. That is, the polymerizable initiator compound represented by the general formula (Y) in the present invention has both a polymerizable group and a β-dicarbonyl skeleton, and thus can be referred to as a "polymerizable β-dicarbonyl-based initiator compound".

[0028] It should be noted that the polymerizable initiator compound including the polymerizable initiator compound represented by the general formula (Y) is not included in the polymerizable compound described later.

[0029] In recent years, high-precision pixels have been required in PSA-type liquid crystal display elements such as 4K and 8K. Therefore, the areas of the wiring and the light-shielding portion are increased, and a considerable amount of UV light is filtered out, resulting in the following problems: in the same UV irradiation process as in the past, the formation of the tilt angle becomes insufficient, the polymerizable compound does not polymerize sufficiently, and a large amount of the polymerizable compound remains. In addition, it has been confirmed that due to the deterioration of the response speed and the deterioration of the orientation, afterimages occur, and in addition, the remaining polymerizable compound polymerizes slowly during driving, the tilt angle changes, and display defects such as image sticking (IS) occur.

[0030] The polymerizable initiator compound according to the present invention can achieve a moderately fast polymerization rate and can impart a target pretilt angle within a short UV irradiation time. Further, if the polymerization rate is moderately fast, the residual amount of the polymerizable compound can be reduced. Therefore, the production efficiency of manufacturing a PSA type liquid crystal display element can be improved. Here, in the polymerizable initiator compound represented by the general formula (Y), the β-dicarbonyl structure functions as a polymerization initiation site, and since it has a liquid crystal precursor structure, it has high solubility and excellent compatibility with the liquid crystal compound. Therefore, the polymerizable initiator compound represented by the general formula (Y) can exhibit the same effect as the conventional non-polymerizable initiator compound with a small content. In addition, since it is difficult to precipitate from the liquid crystal composition, a larger amount can be added compared to the conventional initiator compound, and rapid and sufficient polymerization can be achieved.

[0031] In addition, in the liquid crystal composition according to the present invention, by containing the polymerizable initiator compound represented by the general formula (Y), sufficient polymerization can be achieved at a moderately fast rate, and the UV irradiation time can be shortened. Therefore, deterioration of the liquid crystal composition and a decrease in the voltage holding ratio (VHR) due to UV irradiation can be suppressed. Specifically, the initiator compounds commonly used in conventional liquid crystal compositions do not have a polymerization function (i.e., a polymerizable group), but such non-polymerizable initiator compounds have the effect of accelerating the polymerization rate. On the other hand, the residual portion of the compound is dispersed (diffused) in the liquid crystal layer, so it becomes an ion conduction source and causes a decrease in VHR. On the other hand, since the polymerizable compound represented by the above general formula (Y) has a polymerization portion (polymerizable group), the polymerizable compound represented by the general formula (Y) can form a polymer by ultraviolet irradiation and can fix the main polymer to the substrate interface after UV treatment. Thus, even when the panel is driven, the polymer of the polymerizable compound represented by the general formula (Y) is fixed to the substrate. Accordingly, the polymerizable initiator compound represented by the general formula (Y) itself does not become an ion conduction source, and the VHR can be improved.

[0032] The above effects can be significantly exerted in the case of containing a polymerizable compound. When manufacturing a liquid crystal display element using a polymer stabilization technique, the following steps are included: irradiating ultraviolet rays to a liquid crystal composition containing a polymerizable compound to polymerize the polymerizable compound, and forming a polymer layer composed of a polymer of the polymerizable compound at the substrate interface of the element. When the liquid crystal composition of the present invention contains a polymerizable compound, the β-dicarbonyl structure of the polymerizable compound represented by the general formula (Y) functions as a polymerization initiator in the above steps, so that the polymerization in the liquid crystal composition proceeds at a moderately fast rate, and thus a pretilt angle can be formed within a short UV irradiation time. Further, it is presumed that the polymerizable group of the polymerizable initiator compound represented by the general formula (Y) reacts with a part of the polymerizable compound, and as a result, the polymerizable initiator compound represented by the general formula (Y) enters into the polymer layer formed by the polymerization of the polymerizable compound. It is presumed that the polymerizable initiator compound represented by the general formula (Y) thus entering the polymer layer is fixed in the polymer layer and thus does not function as an ion conduction source, and therefore, compared with the case of using a non-polymerizable initiator compound, the reduction of VHR can be more effectively suppressed.

[0033] Preferably, the compound is as follows:

[0034] In the general formula (Y), R y1 and R y2 each independently represent a linear or branched alkyl group having 1 to 30 carbon atoms, in which a hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group or a nitro group, and -CH 2 - in the alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent continuously.

[0035] S y1 and S y2 each independently represent a single bond or an alkylene group having 1 to 12 carbon atoms, in which a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and -CH 2 - in the alkylene group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent continuously.

[0036] Z y1 and Z y2 each independently represent a single bond, -C 2 H 4 -, -C 4 H 8 -, -C 3 H 6-, -OCH 2 -, -CH 2 O-, -CO-, -COO-, -OCO-, -OCOOCH 2 -, -CH 2 OCOO-, -OCH 2 CH 2 O-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COO-CRa=CH-COO-, -COO-CRa=CH-OCO-, -OCO-CRa=CH-COO-, -OCO-CRa=CH-OCO-, -COOC 2 H 4 -, -OCOC 2 H 4 -, -C 2 H 4 OCO-, -CH 2 OCO-, -COOCH 2 -, -OCOCH 2 -, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF 2 O-, -OCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - or -C≡C- (wherein, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),

[0037] M y1 and M y2 each independently represents a divalent aromatic group, a divalent cycloaliphatic group, a divalent heterocyclic compound group, a divalent condensed ring or a divalent condensed polycycle, and the hydrogen atoms in these ring structures may be substituted by L y1 substituted, L y1 represents a halogen atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 30 carbon atoms, and the hydrogen atoms in the alkyl group may be substituted by a halogen atom, a cyano group or a nitro group, and -CH 2 - in the alkyl group may be substituted by -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent continuously, and m and n each independently represent an integer of 0 to 3, and the sum of m + n here is 1 to 6,

[0038] P y1 and Py2 Represents an aggregating group.

[0039] R y1 and R y2 Preferably each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms, wherein the hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom or a cyano group, and -CH 2 - in the alkyl group may be substituted by -CH=CH-, -C≡C-, -CO-, -COO- or -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent continuously, more preferably each independently represents a linear or branched alkyl group having 1 to 6 carbon atoms, wherein the hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom or a cyano group, and -CH 2 - in the alkyl group may be substituted by -CH=CH-, -C≡C-, -CO-, -COO- or -OCO-, -OCOO- or -O-, but two or more -O- will not be adjacent continuously, further preferably each independently represents a linear or branched alkyl group having 1 to 6 carbon atoms.

[0040] S y1 and S y2 Preferably each independently represents a single bond or an alkylene group having 1 to 6 carbon atoms, wherein the hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom or a cyano group, and -CH 2 - in the alkylene group may be substituted by -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent continuously, more preferably each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, wherein the hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom or a cyano group, and -CH 2 - in the alkylene group may be substituted by -CH=CH-, -CO-, -O-, -COO- or -OCO-, but two or more -O- will not be adjacent continuously, further preferably each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, and -CH 2 - in the alkylene group may be substituted by -CH=CH-, -O-, -CO-, -COO- or -OCO-, but two or more -O- will not be adjacent continuously, particularly preferably a single bond, -CH 2 CH 2 -,-CH 2 O-,-OCH 2 -,-COO- or -OCO-.

[0041] Z y1 and Z y2 Preferably each independently represents a single bond, -C 2 H 4 -,-C4 H 8 -, -C 3 H 6 -, -OCH 2 -, -CH 2 O-, -CO-, -COO-, -OCO-, -OCOOCH 2 -, -CH 2 OCOO-, -OCH 2 CH 2 O-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COO-CRa=CH-COO-, -COO-CRa=CH-OCO-, -OCO-CRa=CH-COO-, -OCO-CRa=CH-OCO-, -COOC 2 H 4 -, -OCOC 2 H 4 -, -C 2 H 4 OCO-, -CH 2 OCO-, -COOCH 2 -, -OCOCH 2 -, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF 2 O-, -OCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - or -C≡C- (wherein, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), more preferably a single bond, -C 2 H 4 -, -C 4 H 8 -, -OCH 2 -, -CH 2 O-, -COO-, -OCO-, -OCOOCH 2 -, -CH 2 OCOO-, -OCH 2 CH 2O−, −CH=CRa−COO−, −CH=CRa−OCO−, −COO−CRa=CH−, −OCO−CRa=CH−, −COO−CRa=CH−COO−, −COO−CRa=CH−OCO−, −OCO−CRa=CH−COO−, −OCO−CRa=CH−OCO−, −COOC 2 H 4 −, −OCOC 2 H 4 −, −C 2 H 4 OCO−, −CH=CH−, −CF=CF−, −CF=CH−, −CH=CF−, −CF 2 O−, −OCF 2 −, −CF 2 CH 2 −, −CH 2 CF 2 −, −CF 2 CF 2 − or −C≡C− (wherein, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), more preferably a single bond, −C 2 H 4 −, −C 4 H 8 −, −OCH 2 −, −CH 2 O−, −COO−, −OCO−, −OCH 2 CH 2 O−, −CH=CRa−COO−, −CH=CRa−OCO−, −COO−CRa=CH−, −OCO−CRa=CH−, −COOC 2 H 4 −, −OCOC 2 H 4 −, −C 2 H 4 OCO−, −CH=CH−, −CF=CF−, −CF 2 O−, −OCF 2 −, −CF 2 CF 2 − or −C≡C− (wherein, Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), particularly preferably a single bond, −C 2 H 4 −, −C 4 H 8 −, −OCH 2 −, −CH 2 O−, −COO−, −OCO−, −OCH 2 CH2 O-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH- or -C≡C-.

[0042] M y1 and M y2 each independently represents a divalent aromatic group, a divalent cycloaliphatic group, a divalent heterocyclic compound group, a divalent condensed ring or a divalent condensed polycyclic ring, preferably a group selected from the group consisting of the following groups:

[0043] (a) 1,4-cyclohexylene (one -CH 2 - or two or more non-adjacent -CH 2 - in this group may be substituted with -O-.)

[0044] (b) 1,4-phenylene, 1,3-phenylene (one -CH= or two or more non-adjacent -CH= in this group may be substituted with -N=.) and

[0045] (c) naphthalene-1,4-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be substituted with -N=.)

[0046] In addition, the above groups (a), (b) and (c) are also preferably substituted with L y1 substituted.

[0047] In addition, M y1 and M y2 are more preferably 1,4-cyclohexylene, 1,4-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl among the above groups (a), (b) and (c), and these groups are also preferably substituted with L y1 substituted.

[0048] L y1 represents a halogen atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 30 carbon atoms, a hydrogen atom in this alkyl group may be substituted with a halogen atom, a cyano group or a nitro group, and -CH 2 - in this alkyl group may be substituted with -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent to cause continuity, preferably represents a fluorine atom, a cyano group, a linear or branched alkyl group having 1 to 6 carbon atoms, a hydrogen atom in this alkyl group may be substituted with a fluorine atom, and -CH 2- It may be substituted by -CH=CH-, -C≡C-, -CO-, -COO-, -OCO- or -O-, but two or more -O- will not be adjacent continuously. More preferably, it represents a fluorine atom, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, and the hydrogen atom in the alkyl group may be substituted by a fluorine atom. The -CH 2 - It may be substituted by -COO-, -OCO- or -O-, but two or more -O- will not be adjacent continuously. Further preferably, it represents a fluorine atom, a straight-chain alkyl group or an alkoxy group having 1 to 4 carbon atoms.

[0049] P y1 and P y2 Preferably, they each independently represent a substituent selected from the group represented by the following general formula (P-1) to general formula (P-14),

[0050] [Chemical formula 2]

[0051]

[0052] (In the formula, the black dot represents the bonding key to Z y1 or Z y2 .) More preferably, it represents (P-1), (P-2), (P-4), (P-5), (P-7), (P-9), (P-11), (P-12), and (P-13). Further preferably, it represents (P-1), (P-2), (P-7), (P-12), and (P-13). Particularly preferably, it is (P-1) and (P-2).

[0053] m and n each independently preferably represent an integer of 0 to 2, further preferably an integer of 1 to 2. The total of m + n is preferably 1 to 6, more preferably 1 to 4, and particularly preferably 2 to 4.

[0054] As the structure represented by the general formula (Y), the following formula (Y-A) can be preferably exemplified.

[0055] [Chemical formula 3]

[0056]

[0057] (In the formula, R y1a and R y2a each independently represent a straight-chain or branched alkyl group having 1 to 12 carbon atoms, and the hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom or a cyano group. The -CH 2 - may be substituted by -CH=CH-, -C≡C-, -CO-, -COO- or -OCO-, -OCOO-, -O-, -NH- or -S-, but two or more -O- will not be adjacent continuously.

[0058] S y1a and Sy2a Each independently represents a single bond or an alkylene group having 1 to 6 carbon atoms, in which the hydrogen atoms in the alkylene group may be substituted by fluorine atoms, chlorine atoms or cyano groups, and -CH in the alkylene group 2 - may be substituted by -CH=CH-, -C≡C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH- or -S-, provided that two or more -O- do not adjoin each other

[0059] Z y1a and Z y2a Each independently represents a single bond, -C 2 H 4 -, -C 4 H 8 -, -OCH 2 -, -CH 2 O-, -COO-, -OCO-, -OCH 2 CH 2 O-, -CH=CRa-COO-, -CH=CRa-OCO-, -COO-CRa=CH-, -OCO-CRa=CH-, -COOC 2 H 4 -, -OCOC 2 H 4 -, -C 2 H 4 OCO-, -CH=CH-, -CF=CF-, -CF 2 O-, -OCF 2 -, -CF 2 CF 2 -, or -C≡C- (wherein, each Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),

[0060] M y1a and M y2a Each independently is a group selected from the group consisting of the following groups

[0061] (a) 1,4-cyclohexylene (one -CH in the group 2 - or two or more non-adjacent -CH 2 - may be substituted by -O-.)

[0062] (b) 1,4-phenylene, 1,3-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted by -N=), and

[0063] (c) naphthalene-1,4-diyl, naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl or decahydronaphthalene-2,6-diyl (one -CH= or two or more non-adjacent -CH= in naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl may be replaced by -N=).

[0064] The hydrogen atoms in these ring structures may be replaced by L y1a substituted, and L y1a represents a fluorine atom, a cyano group, a linear or branched alkyl group having 1 to 6 carbon atoms, the hydrogen atoms in the alkyl group may be replaced by fluorine atoms, and -CH 2 - in the alkyl group may be replaced by -CH=CH-, -C≡C-, -CO-, -COO-, -OCO- or -O-, but two or more -O- will not be consecutive to cause adjacency.

[0065] ma and na each independently represent an integer from 0 to 3, where the sum of m + n is 1 to 4.

[0066] P y1a and P y2a represent the groups represented by the above general formulas (P-1) to (P-14).)

[0067] In addition, as the structure represented by the general formula (Y), the structures represented by the following formulas (Y-A1) to (Y-A8) are also preferred.

[0068] [Chemical formula 4]

[0069]

[0070] [Chemical formula 5]

[0071]

[0072] [Chemical formula 6]

[0073]

[0074] (In the formula, R yi1 and R yi2 each represent the same meaning as R y1 and R y2 in the general formula (Y), S yi1 and S yi2 each represent the same meaning as S y1 and S y2 in the general formula (Y), Z yi1 and Z yi2 each represent the same meaning as Z y1 and Z y2 in the general formula (Y), M yi1 and Myi2 respectively represent the same meanings as M in the general formula (Y) y1 and M y2 respectively represent the same meanings as P in the general formula (Y) yi1 and P yi2 mi and ni respectively represent the same meanings as m and n in the general formula (Y).) y1 and P y2 respectively represent the same meanings as P in the general formula (Y)

[0075] As the polymerizable compound represented by the general formula (Y) involved in the present invention, specifically, compounds represented by the general formula (Y-1-1) to the general formula (Y-16-33) are preferred.

[0076] [Chemical formula 7]

[0077]

[0078] [Chemical formula 8]

[0079]

[0080] [Chemical formula 9]

[0081]

[0082] [Chemical formula 10]

[0083]

[0084] [Chemical formula 11]

[0085]

[0086] [Chemical formula 12]

[0087]

[0088] [Chemical formula 13]

[0089]

[0090] [Chemical formula 14]

[0091]

[0092] [Chemical formula 15]

[0093]

[0094] [Chemical formula 16]

[0095]

[0096] [Chemical formula 17]

[0097]

[0098] [Chemical Formula 18]

[0099]

[0100] [Chemical Formula 19]

[0101]

[0102] [Chemical Formula 20]

[0103]

[0104] [Chemical Formula 21]

[0105]

[0106] [Chemical Formula 22]

[0107]

[0108] [Chemical Formula 23]

[0109]

[0110] [Chemical Formula 24]

[0111]

[0112] [Chemical Formula 25]

[0113]

[0114] [Chemical Formula 26]

[0115]

[0116] [Chemical Formula 27]

[0117]

[0118] [Chemical Formula 28]

[0119]

[0120] [Chemical Formula 29]

[0121]

[0122] [Chemical Formula 30]

[0123]

[0124] [Chemical Formula 31]

[0125]

[0126] [Chemical formula 32]

[0127]

[0128] [Chemical formula 33]

[0129]

[0130] [Chemical formula 34]

[0131]

[0132] [Chemical formula 35]

[0133]

[0134] [Chemical formula 36]

[0135]

[0136] [Chemical formula 37]

[0137]

[0138] [Chemical formula 38]

[0139]

[0140] A composition containing one or two or more compounds represented by the general formula (Y) preferably has a liquid crystal phase at room temperature. Regarding the compound represented by the general formula (Y), as a lower limit value in the composition, it is preferably contained in an amount of 0.005% or more, preferably 0.01% or more, preferably 0.02% or more, preferably 0.03% or more, preferably 0.05% or more, preferably 0.07% or more, preferably 0.1% or more, preferably 0.15% or more, preferably 0.2% or more, preferably 0.25% or more, preferably 0.3% or more, preferably 0.5% or more, preferably 1% or more. In addition, as an upper limit value, it is preferably contained in an amount of 5% or less, preferably 3% or less, preferably 1% or less, preferably 0.5% or less, preferably 0.45% or less, preferably 0.4% or less, preferably 0.35% or less, preferably 0.3% or less, preferably 0.25% or less, preferably 0.2% or less, preferably 0.15% or less, preferably 0.1% or less, preferably 0.07% or less, preferably 0.05% or less, preferably 0.03% or less.

[0141] More specifically, it preferably contains 0.01 to 5% by mass, more preferably 0.01 to 0.3% by mass, still more preferably 0.02 to 0.3% by mass, and particularly preferably 0.05 to 0.25% by mass. More specifically in detail, when emphasis is placed on suppressing precipitation at low temperatures, its content is preferably 0.01 to 0.1% by mass.

[0142] In the composition containing the compound represented by the general formula (Y), in addition to the compound represented by the general formula (Y), it may further contain a compound having a liquid crystal phase, or may contain a compound not having a liquid crystal phase.

[0143] In the present invention, the compound represented by the general formula (Y) can be produced as follows. Of course, the gist and scope of application of the present invention are not limited by these production examples.

[0144] (Manufacturing method of compound - 1)

[0145] [Chemical formula 39]

[0146]

[0147] In the formula, R i1 and R i2 respectively represent the same meanings as R y1 and R y2 in the general formula (Y), S i1 and S i2 respectively represent the same meanings as S y1 and S y2 in the general formula (Y), Z i1 and Z i2 respectively represent the same meanings as Z y1 and Z y2 in the general formula (Y), M i1 and M i2 respectively represent the same meanings as M y1 and M y2 in the general formula (Y), and mx and nx respectively represent the same meanings as m and n in the general formula (Y).)

[0148] By the transesterification reaction of the hydroxyl group of the compound represented by the general formula (S - 1) with ethyl methacrylate using a tin catalyst, the compound of the general formula (Y) - 1 having a methacryloyl group as a polymerizable group can be obtained.

[0149] (Manufacturing method of compound - 2)

[0150] [Chemical formula 40]

[0151]

[0152] (In the formula, Ri1 and R i2 respectively represent the same meanings as R in the general formula (Y) y1 and R y2 respectively represent the same meanings as S in the general formula (Y) i1 and S i2 respectively represent the same meanings as S in the general formula (Y) y1 and S y2 respectively represent the same meanings as Z in the general formula (Y) i1 and Z i2 respectively represent the same meanings as Z in the general formula (Y) y1 and Z y2 respectively represent the same meanings as M in the general formula (Y) i1 and M i2 respectively represent the same meanings as M in the general formula (Y) y1 and M y2 respectively represent the same meanings as m and n in the general formula (Y), mx and nx respectively represent the same meanings as m and n in the general formula (Y), R s1 represents an alkyl group having 1 to 6 carbon atoms, and -OPg represents a hydroxyl group protected by a protecting group Pg.)

[0153] By reducing the compound represented by the general formula (S-2), the compound represented by the general formula (S-3) can be obtained. Examples of the reducing agent include diisobutylaluminum hydride and the like. Alternatively, by reducing the compound represented by the general formula (S-2) to form an alcohol and then oxidizing it to form an aldehyde, the compound represented by the general formula (S-3) can also be obtained. In this case, examples of the reducing agent include lithium aluminum hydride, diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, etc. In addition, examples of the oxidizing agent include pyridinium chlorochromate, oxalyl chloride, etc. The compound represented by the general formula (S-6) can be obtained by reacting the compound represented by the general formula (S-3) with the compounds represented by the general formulas (S-4) and (S-5) (wherein X represents chlorine, bromine or iodine). As a reaction example, for example, a Wittig reaction can be cited in which a base is reacted with the compounds represented by the general formulas (S-4) and (S-5) to form a phosphonium ylide and then reacted with the compound represented by the general formula (S-3). At this time, examples of the base include potassium tert-butoxide and the like. Further, when Pg is benzyl, by catalytic hydrogen reduction in the presence of 5% palladium-carbon, a hydroxyl group-containing compound represented by the general formula (S-7) can be obtained. Next, a deacetalization reaction is carried out under acidic conditions using dilute hydrochloric acid or the like, whereby the compound represented by (S-8) can be obtained. Next, by transesterification of the generated hydroxyl group with ethyl acrylate using a tin catalyst, the target general formula (Y)-2 having an acryloyl group as a polymerizable group can be obtained.

[0154] (Method for manufacturing a compound - 3)

[0155] [Chemical formula 41]

[0156]

[0157] (wherein, R i1 and R i2 respectively represent the same meanings as R y1 and R y2 in the general formula (Y), S i1 and S i2 respectively represent the same meanings as S y1 and S y2 in the general formula (Y), Z i1 and Z i2 respectively represent the same meanings as Z y1 and Z y2 in the general formula (Y), M i1 and M i2 respectively represent the same meanings as M y1 and M y2 in the general formula (Y), mx and nx respectively represent the same meanings as m and n in the general formula (Y), -OPg represents a hydroxyl group protected by a protecting group Pg.)

[0158] By reacting the compound represented by the general formula (S-9) with the compounds represented by the general formulas (S-10) and (S-11), the compound of the general formula (S-12) can be obtained. As reaction examples, for example, the Williamson reaction in which p-toluenesulfonyl chloride, methylsulfonyl chloride, etc. react with the hydroxyl group of the general formula (S-9) to form a leaving group and then react with (S-10) and (S-11) in the presence of a base can be cited. As the base, for example, potassium carbonate, cesium carbonate, etc. can be cited. In addition, the Mitsunobu reaction in which the hydroxyl group is activated with an azocarboxylic acid ester and triphenylphosphine and then reacts with an alcohol can be cited. As the azocarboxylic acid ester, for example, diethyl azodicarboxylate, diisopropyl azodicarboxylate, etc. can be cited. Further, when Pg is a benzyl group, the hydroxyl group-containing compound represented by the general formula (S-13) can be obtained by carrying out catalytic hydrogen reduction in the presence of 5% palladium-carbon. Next, the target compound of the general formula (Y)-3 having a methacryloyl group as a polymerizable group can be obtained by the transesterification reaction of the generated hydroxyl group with ethyl methacrylate using a tin catalyst.)

[0159] (Method for manufacturing a compound - 4)

[0160] [Chemical formula 42]

[0161]

[0162] (wherein, R i1 and R i2 respectively represent the same meanings as R y1 and R y2 in the general formula (Y), Si1 and S i2 respectively represent the same meanings as S in the general formula (Y) y1 and S y2 respectively represent the same meanings as Z in the general formula (Y) i1 and Z i2 respectively represent the same meanings as Z in the general formula (Y) y1 and Z y2 respectively represent the same meanings as M in the general formula (Y) i1 and M i2 respectively represent the same meanings as M in the general formula (Y) y1 and M y2 respectively represent the same meanings as mx and nx in the general formula (Y) respectively represent the same meanings as m and n in the general formula (Y), and -OPg represents a hydroxyl group protected by a protecting group Pg.)

[0163] By reacting the compound represented by the general formula (S-14) with the compounds represented by the general formulas (S-10) and (S-11), the compound represented by the general formula (S-15) can be obtained. As a reaction example, for example, after making a halogenating agent act on the carboxyl group of the general formula (S-14) to prepare an acyl halide, it is reacted with the compounds represented by the general formulas (S-10) and (S-11) to obtain the compound represented by (S-15). As the halogenating agent, for example, thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfonyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus tribromide, etc. can be cited. In addition, an esterification reaction of a carboxyl group and an alcohol using a dehydrating condensing agent such as dicyclohexylcarbodiimide can also be cited. Further, when Pg is benzyl, the same operation as in Production Method 3 is carried out, and catalytic hydrogen reduction is carried out to obtain the hydroxyl group-containing compound represented by the general formula (S-16). Next, through the transesterification reaction of the generated hydroxyl group with ethyl methacrylate using a tin catalyst, the target compound of the general formula (Y)-4 having a methacryloyl group as a polymerizable group can be obtained.

[0164] (Method for manufacturing a compound - 5)

[0165] [Chemical formula 43]

[0166]

[0167] (In the formula, R i1 and R i2 respectively represent the same meanings as R in the general formula (Y) y1 and R y2 respectively represent the same meanings as S in the general formula (Y) i1 and S i2 respectively represent the same meanings as S in the general formula (Y) y1 and S y2 respectively represent the same meanings as Z in the general formula (Y) i1 and Z i2 respectively represent the same meanings as Z in the general formula (Y) y1 and Z y2The same meaning, M i1 and M i2 respectively represent the same meaning as M in the general formula (Y) y1 and M y2 (The same meaning, mx and nx respectively represent the same meaning as m and n in the general formula (Y), and -OPg represents a hydroxyl group protected by the protecting group Pg.)

[0168] By reacting the compound represented by the general formula (S-17) with the compounds represented by the general formulas (S-18) and (S-19), the compound represented by the general formula (S-20) can be obtained. As a reaction example, for example, after making an enolate by removing the hydrogen of the compound represented by the general formula (S-17) with a base, a Michael addition reaction in which it reacts with the compounds of the general formulas (S-18) and (S-19) can obtain the general formula (S-20). As the base, for example, triethylamine, diazabicycloundecene, etc. can be cited. Further, when Pg is benzyl, the same operation as in Production Method 3 is carried out, and catalytic hydrogenation is carried out to obtain the hydroxyl group-containing compound represented by the general formula (S-21). Next, by the transesterification reaction of the generated hydroxyl group with ethyl methacrylate using a tin catalyst, the target general formula (Y)-5 having a methacryloyl group as a polymerizable group can be obtained.

[0169] (Method for manufacturing a compound - 6)

[0170] [Chemical formula 44]

[0171]

[0172] (In the formula, R i1 and R i2 respectively represent the same meaning as R in the general formula (Y) y1 and R y2 the same meaning, S i1 and S i2 respectively represent the same meaning as S in the general formula (Y) y1 and S y2 the same meaning, Z i1 and Z i2 respectively represent the same meaning as Z in the general formula (Y) y1 and Z y2 the same meaning, M i1 and M i2 respectively represent the same meaning as M in the general formula (Y) y1 and M y2 the same meaning, mx and nx respectively represent the same meaning as m and n in the general formula (Y), R s1 represents an alkyl group having 1 to 6 carbon atoms, and -OPg represents a hydroxyl group protected by the protecting group Pg.)

[0173] Operating in the same manner as in Production Method 2, the compound represented by the general formula (S-22) is reduced to obtain the compound represented by the general formula (S-23). Alternatively, operating in the same manner as in Production Method 2, the compound represented by the general formula (S-22) is reduced to form an alcohol, which is then oxidized to form an aldehyde, thereby also obtaining the compound represented by the general formula (S-23). Regarding the compound represented by the general formula (S-24), it can be obtained by reacting the compound represented by the general formula (S-23) with the compound represented by the general formula (S-4) by operating in the same manner as in Production Method 2 (wherein X represents chlorine, bromine, or iodine). Further, when Pg is benzyl, by performing catalytic hydrogenation in the same manner as in Production Method 2, a hydroxyl group-containing compound represented by the general formula (S-25) can be obtained. Next, by transesterification of the resulting hydroxyl group with ethyl methacrylate using a tin catalyst, the compound represented by the general formula (S-26) can be obtained. For the compound represented by the general formula (S-26), by operating in the same manner as in Production Method 5 and reacting it with the compound represented by the general formula (S-19), the compound represented by the general formula (S-27) can be obtained. Further, when Pg is tetrahydropyranyl, by performing a deacetalization reaction under acidic conditions using dilute hydrochloric acid or the like, the compound represented by (S-28) can be obtained. Next, by transesterification of the resulting hydroxyl group with ethyl acrylate using a tin catalyst, the target general formula (Y)-6 can be obtained.

[0174] (Method for Producing Compound - 7)

[0175] [Chemical Formula 45]

[0176]

[0177] (In the formula, R i1 and R i2 each represent the same meaning as R y1 and R y2 in the general formula (Y), S i1 and S i2 each represent the same meaning as S y1 and S y2 in the general formula (Y), Z i1 and Z i2 each represent the same meaning as Z y1 and Z y2 in the general formula (Y), M i1 and M i2 each represent the same meaning as M y1 and M y2The same meanings, mx and nx respectively represent the same meanings as m and n in the general formula (Y), and -OPg represents a hydroxyl group protected by the protecting group Pg.) Operating in the same manner as in Production Method 3, reacting the compound represented by the general formula (S-29) with the compound represented by the general formula (S-10) enables the production of the compound of the general formula (S-30). Further, when Pg is benzyl, operating in the same manner as in Production Method 3 and performing catalytic hydrogenation enables the production of the hydroxyl group-containing compound represented by the general formula (S-31). Next, through the transesterification reaction of the generated hydroxyl group with ethyl methacrylate using a tin catalyst, the compound represented by the general formula (S-32) can be obtained. For the compound represented by the general formula (S-32), operating in the same manner as in Production Method 5 and reacting it with the compound represented by the general formula (S-19) enables the production of the compound represented by the general formula (S-33). Further, when Pg is tetrahydropyranyl, by performing a deacetalization reaction under acidic conditions using dilute hydrochloric acid or the like, the compound represented by (S-34) can be obtained. Next, through the transesterification reaction of the generated hydroxyl group with ethyl acrylate using a tin catalyst, the target general formula (Y)-7 can be obtained.

[0178] (Method for manufacturing compound - 8)

[0179] [Chemical formula 46]

[0180]

[0181] (In the formula, R i1 and R i2 respectively represent the same meanings as R y1 and R y2 in the general formula (Y), S i1 and S i2 respectively represent the same meanings as S y1 and S y2 in the general formula (Y), Z i1 and Z i2 respectively represent the same meanings as Z y1 and Z y2 in the general formula (Y), M i1 and M i2 respectively represent the same meanings as M y1 and M y2 in the general formula (Y), mx and nx respectively represent the same meanings as m and n in the general formula (Y), and -OPg represents a hydroxyl group protected by the protecting group Pg.)

[0182] Operating in the same manner as in Production Method 4, the compound represented by the general formula (S-35) is reacted with the compound represented by the general formula (S-10), whereby the compound represented by the general formula (S-36) can be obtained. Further, when Pg is benzyl, operating in the same manner as in Production Method 3, catalytic hydrogenation is carried out, whereby the hydroxy group-containing compound represented by the general formula (S-37) can be obtained. Next, by the transesterification reaction of the generated hydroxy group with ethyl methacrylate using a tin catalyst, the compound represented by the general formula (S-38) can be obtained. For the compound represented by the general formula (S-38), operating in the same manner as in Production Method 5, it is reacted with the compound represented by the general formula (S-19), whereby the compound represented by the general formula (S-39) can be obtained. Further, when Pg is tetrahydropyranyl, by carrying out a deacetalization reaction under acidic conditions using dilute hydrochloric acid or the like, the compound represented by (S-40) can be obtained. Next, by the transesterification reaction of the generated hydroxy group with ethyl acrylate using a tin catalyst, the target general formula (Y)-8 can be obtained.

[0183] (Method for manufacturing compound - 9)

[0184] [Chemical formula 47]

[0185]

[0186] (In the formula, R i1 and R i2 each represent the same meaning as R y1 and R y2 in the general formula (Y), S i1 and S i2 each represent the same meaning as S y1 and S y2 in the general formula (Y), Z i1 and Z i2 each represent the same meaning as Z y1 and Z y2 in the general formula (Y), M i1 and M i2 each represent the same meaning as M y1 and M y2 in the general formula (Y), mx and nx each represent the same meaning as m and n in the general formula (Y), and -OPg represents a hydroxy group protected by the protecting group Pg.)

[0187] For the compound represented by the general formula (S-25), by operating in the same manner as in Production Method 5 to react it with the compound represented by the general formula (S-19), the compound represented by the general formula (S-41) can be obtained. Next, through the transesterification reaction of the generated hydroxyl group with ethyl acrylate using a tin catalyst, the compound represented by the general formula (S-42) can be obtained. Further, when Pg is a tetrahydropyranyl group, by performing a deacetalization reaction under acidic conditions using dilute hydrochloric acid or the like, the compound represented by (S-43) can be obtained. Next, through the transesterification reaction of the generated hydroxyl group with ethyl methacrylate using a tin catalyst, the target general formula (Y)-9 can be obtained.

[0188] (Method for manufacturing compound - 10)

[0189] [Chemical formula 48]

[0190]

[0191] (In the formula, R i1 and R i2 respectively represent the same meanings as R y1 and R y2 in the general formula (Y), S i1 and S i2 respectively represent the same meanings as S y1 and S y2 in the general formula (Y), Z i1 and Z i2 respectively represent the same meanings as Z y1 and Z y2 in the general formula (Y), M i1 and M i2 respectively represent the same meanings as M y1 and M y2 in the general formula (Y), mx and nx respectively represent the same meanings as m and n in the general formula (Y), and -OPg represents a hydroxyl group protected by the protecting group Pg.)

[0192] For the compound represented by the general formula (S-31), by operating in the same manner as in Production Method 5 to react it with the compound represented by the general formula (S-19), the compound represented by the general formula (S-44) can be obtained. Next, through the transesterification reaction of the generated hydroxyl group with ethyl acrylate using a tin catalyst, the compound represented by the general formula (S-45) can be obtained. Further, when Pg is a tetrahydropyranyl group, by performing a deacetalization reaction under acidic conditions using dilute hydrochloric acid or the like, the compound represented by (S-46) can be obtained. Next, through the transesterification reaction of the generated hydroxyl group with ethyl methacrylate using a tin catalyst, the target general formula (Y)-10 can be obtained.

[0193] (Method for Manufacturing Compound - 11)

[0194] [Chemical Formula 49]

[0195]

[0196] (In the formula, R i1 and R i2 respectively represent the same meanings as R y1 and R y2 in the general formula (Y), S i1 and S i2 respectively represent the same meanings as S y1 and S y2 in the general formula (Y), Z i1 and Z i2 respectively represent the same meanings as Z y1 and Z y2 in the general formula (Y), M i1 and M i2 respectively represent the same meanings as M y1 and M y2 in the general formula (Y), mx and nx respectively represent the same meanings as m and n in the general formula (Y), -OPg represents a hydroxyl group protected by the protecting group Pg.)

[0197] For the compound represented by the general formula (S - 37), by operating in the same manner as in Preparation Method 5 to react it with the compound represented by the general formula (S - 19), the compound represented by the general formula (S - 47) can be obtained. Next, through the transesterification reaction of the generated hydroxyl group with ethyl acrylate using a tin catalyst, the compound represented by the general formula (S - 48) can be obtained. Further, when Pg is a tetrahydropyranyl group, by performing a deacetalization reaction under acidic conditions using dilute hydrochloric acid or the like, the compound represented by (S - 49) can be obtained. Next, through the transesterification reaction of the generated hydroxyl group with ethyl methacrylate using a tin catalyst, the target general formula (Y) - 11 can be obtained.

[0198] As reaction conditions other than those described in the foregoing respective steps, examples thereof include reaction conditions described in literature such as Experimental Chemistry Course (edited by The Chemical Society of Japan, published by Maruzen Co., Ltd.), Organic Syntheses (A John Wiley & Sons, Inc., Publication), Beilstein Handbook of Organic Chemistry (Beilstein-Institut fuer Literatur der Organischen Chemie, Springer-Verlag Berlin and Heidelberg GmbH & Co. K), Fiesers’ Reagents for Organic Synthesis (John Wiley & Sons, Inc.), etc., or reaction conditions described in databases such as SciFinder (Chemical Abstracts Service, American Chemical Society), Reaxys (Elsevier Ltd.), etc.

[0199] In addition, a reaction solvent can be appropriately used in each step. Specific examples of the solvent include ethanol, tetrahydrofuran, toluene, dichloromethane, water, etc. When carrying out a reaction in a two-phase system of an organic solvent and water, a phase transfer catalyst can also be added. Specific examples of the phase transfer catalyst include benzyltrimethylammonium bromide, tetrabutylammonium bromide, etc.

[0200] In addition, purification can be carried out as needed in each step. As purification methods, examples thereof include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, liquid separation treatment, etc. Specific examples of the purification agent include silica gel, NH 2 silica gel, alumina, activated carbon, etc.

[0201] (Liquid crystal composition)

[0202] The compound represented by the general formula (Y) can be added to the liquid crystal composition. One or two or more kinds of the compounds represented by the general formula (Y) of the present invention can be added to the liquid crystal composition, or in addition to the compounds represented by the general formula (Y), known polymerizable compounds, antioxidants, etc. used in the liquid crystal composition can further be contained.

[0203] When two or more kinds of liquid crystal molecules are used in combination, there can be various combinations, but at least one kind contains the following general formula (II). When the dielectric anisotropy of the liquid crystal composition is positive, the following general formula (IIIa), (IIIb) or (IIIc) can be further contained. When the dielectric anisotropy of the liquid crystal composition is negative, a compound represented by the following general formula (IVa), (IVb) or (IVc) can be further contained.

[0204] The compound represented by the general formula (II) is shown below.

[0205] [Chemical formula 50]

[0206] R 21 -M 21 -L 21 -M 22 -(L 22 -M 23 ) o -R 22 (II)

[0207] (In the formula, R 21 and R 22 independently of each other 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 may be substituted with -O- or -S-. In addition, one or two or more hydrogen atoms present in these groups may be substituted with a fluorine atom or a chlorine atom.

[0208] M 21 、M 22 and M 23 independently of each other represent a group selected from the group consisting of the following groups.

[0209] (a) 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-),

[0210] (b) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with a nitrogen atom), 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene and

[0211] (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.

[0212] o represents 0, 1 or 2.

[0213] L21 and L 22 each independently represents a single bond, -CH 2 CH 2 -, -(CH 2 ) 4 -, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 O-, -CH=CH-, -CH=N-N=CH- or -C≡C-, and when there are multiple Ls 22 they may be the same or different, and when there are multiple Ms 23 they may be the same or different.)

[0214] In the compound represented by the general formula (II), R 21 and R 22 are preferably each independently 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 also including 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 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.

[0215] M 21 , M 22 and M 23 are preferably each independently trans-1,4-cyclohexylene (including groups in which one CH 2 group or two non-adjacent CH 2 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 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, more preferably 0 or 1. L 21 and L 22 are preferably each independently a single bond, -CH 2 CH 2 -, -(CH 2 )4 -, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 O-, -CH=CH-, -CH=N-N=CH- or -C≡C-, more preferably a single bond, -CH 2 CH 2 -, -(CH 2 ) 4 -, -OCH 2 - or -CH 2 O-, further preferably a single bond or -CH 2 CH 2 -.

[0216] Among the structures formed by the combination of the above options, -CH=CH-CH=CH-, -C≡C-C≡C- and -CH=CH-C≡C- are not preferred from the perspective of chemical stability. In addition, groups in which hydrogen atoms in these structures are replaced by fluorine atoms are also not preferred. In addition, structures in which oxygen atoms are connected to each other, structures in which sulfur atoms are connected to each other, and structures in which a sulfur atom is connected to an oxygen atom are also not preferred. In addition, structures in which nitrogen atoms are connected to each other, structures in which a nitrogen atom is connected to an oxygen atom, and structures in which a nitrogen atom is connected to a sulfur atom are also not preferred.

[0217] More specifically, regarding the general formula (II), as specific structures, compounds represented by the group consisting of the following general formulas (II-A) to (II-P) are preferred.

[0218] [Chemical formula 51]

[0219]

[0220] (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.)

[0221] R 23 and R 24 More preferably, each independently is 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. In addition, from the perspective of improving the response speed, an alkenyl group having 1 to 5 carbon atoms is preferred.

[0222] Among the compounds represented by General Formula (II-A) to General Formula (II-P), compounds represented by General Formula (II-A), General Formula (II-B), General Formula (II-C), General Formula (II-E), General Formula (II-H), General Formula (II-I), General Formula (II-J) or General Formula (II-K) are preferred, and compounds represented by General Formula (II-A), General Formula (II-C), General Formula (II-E), General Formula (II-H) or General Formula (II-I) are more preferred.

[0223] In the present invention, the composition contains at least one compound represented by General Formula (II), preferably contains 1 to 10 kinds, particularly preferably contains 2 to 8 kinds. The lower limit of the content rate of the compound represented by 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, 80% by mass is preferred, further 70% by mass is preferred, and further 60% by mass is preferred.

[0224] 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 General Formula (IIIa), General Formula (IIIb) and General Formula (IIIc).

[0225] [Chemical Formula 52]

[0226]

[0227] (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. One methylene group or two or more non-adjacent methylene groups present in these groups may be substituted with -O- or -S-. In addition, one or two or more hydrogen atoms present in these groups may be substituted with a fluorine atom or a chlorine atom.

[0228] 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.

[0229] (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-),

[0230] (e) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= in the group may be substituted with -N=), 3-fluoro-1,4-phenylene, 3,5-difluoro-1,4-phenylene, and

[0231] (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,

[0232] The hydrogen atoms contained in the above group (d), group (e) or group (f) may be substituted by a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a chlorine atom, respectively.

[0233] L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 and L 38 Independently represent a single bond, -COO-, -OCO-, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-OCF 2 -、-CF 2 O- or -C≡C-, there are multiple M 32 、M 34 、M 35 、M 37 、M 38 , L 31 , L 33 , L 35 , L 36 and / or L 38 They can be the same or different.

[0234] X 31 , X 32 , X 33 , X 34 , X 35 , X 36 and X 37 independently represent a hydrogen atom or a fluorine atom,

[0235] Y 31 , Y 32 and Y 33independently represent 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,

[0236] p, q, r, s and t independently represent 0, 1 or 2, and q + r and s + t are 2 or less.)

[0237] In the compounds represented by the general formula (IIIa), the general formula (IIIb) and the general formula (IIIc), R 31 , R 32 and R 33 are preferably independently 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 a group in which one methylene group or two or more non-adjacent methylene groups present in these groups are substituted with -O- or -S-, and also including a group 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.

[0238] M 31 , M 32 , M 33 , M 34 , M 35 , M 36 , M 37 and M 38 are preferably independently a trans-1,4-cyclohexylene group (including a group in which one methylene group or two or more non-adjacent methylene groups present in this group are substituted with -O- or -S-), a 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), a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group and a decahydronaphthalene-2,6-diyl group (each group also includes a group in which a hydrogen atom 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, a 1,4-phenylene group, a 3-fluoro-1,4-phenylene group or a 3,5-difluoro-1,4-phenylene group, further preferably a trans-1,4-cyclohexylene group or a 1,4-phenylene group, and particularly preferably a trans-1,4-cyclohexylene group.

[0239] L 31 , L 32 , L 33 , L 34 , L35 , L 36 , L 37 and L 38 are preferably, independently of one another, a single bond, -OCO-, -COO-, -CH 2 CH 2 -, -(CH 2 ) 4 -, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 O- or -C≡C-, more preferably a single bond, -CH 2 CH 2 (CH 2 ) 4 - or -C≡C-, particularly preferably a single bond or -CH 2 CH 2 -. X 31 , X 32 , X 33 , X 34 , X 35 , X 36 and X 37 independently of one another represent a hydrogen atom or a fluorine atom, Y 31 , Y 32 and Y 33 are preferably, independently of one another, a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a thiocyano 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 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, particularly preferably a fluorine atom. p, q, r, s and t independently of one another represent 0, 1 or 2, and q + r and s + t represent 2 or less.

[0240] In the structures formed by combinations of the above options, -CH=CH-CH=CH-, -C≡C-C≡C- and -CH=CH-C≡C- are not preferred from the viewpoint of chemical stability. In addition, structures in which the hydrogen atoms in these structures are replaced by fluorine atoms are also not preferred. In addition, structures in which oxygen atoms are connected to each other, structures in which sulfur atoms are connected to each other, and structures in which a sulfur atom is connected to an oxygen atom are also not preferred. In addition, structures in which nitrogen atoms are connected to each other, structures in which a nitrogen atom is connected to an oxygen atom, and structures in which a nitrogen atom is connected to a sulfur atom are also not preferred.

[0241] Specifically, it preferably represents a structure represented by the following general formula (IIIa-1).

[0242] [Chemical formula 53]

[0243]

[0244] (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, -CH 2 CH 2 -, -(CH 2 ) 4 -, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 O-, or -C≡C-, M 38 represents 1,4-phenylene or trans-1,4-cyclohexylene, X 32 represents a hydrogen atom or a fluorine atom, p 1 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.)

[0245] More specifically, the structures represented by the following general formulas (IIIa-2a) to (IIIa-4d) are preferably used,

[0246] [Chemical formula 54]

[0247]

[0248] [Chemical formula 55]

[0249]

[0250] [Chemical formula 56]

[0251]

[0252] (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 31 and X 32 each independently represent a hydrogen atom or a fluorine atom, 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.)

[0253] The structure represented as follows is also preferred.

[0254] [Chemical formula 57]

[0255]

[0256] (In the formula, R34 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, 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.)

[0257] Regarding the general formula (IIIb), as a specific structure, the structure represented by the following general formula is preferred,

[0258] [Chemical formula 58]

[0259]

[0260] [Chemical formula 59]

[0261]

[0262] [Chemical formula 60]

[0263]

[0264] (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, 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.)

[0265] Regarding the general formula (IIIc), as a specific structure, the structure represented by the following general formula is preferred.

[0266] [Chemical formula 61]

[0267]

[0268] [Chemical formula 62]

[0269]

[0270] [Chemical formula 63]

[0271]

[0272] (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, 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.)

[0273] Containing at least one compound selected from the group consisting of the compounds represented by general formula (IIIa), general formula (IIIb) and general formula (IIIc), preferably containing 1 to 10 kinds, particularly preferably containing 2 to 8 kinds, the lower limit of the content ratio of the group consisting of the compounds represented by general formula (IIIa), general formula (IIIb) and 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.

[0274] When the dielectric anisotropy of the liquid crystal composition is negative, it is preferably further contained a compound selected from the group consisting of the compounds represented by general formula (IVa), general formula (IVb) and general formula (IVc).

[0275] [Chemical formula 64]

[0276]

[0277] (In the formula, R 41 , R 42 , R 43 , R 44 , R 45 and R 46 independently of one another 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.

[0278] M 41 , M 42 , M 43 , M 44 , M 45 , M 46 , M 47 , M 48 and M 49 independently of one another represent a group selected from the group consisting of the following groups.

[0279] (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-),

[0280] (h) 1,4-phenylene (one -CH= or two or more non-adjacent -CH= present in this group may be substituted with a nitrogen atom), and

[0281] (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, wherein the hydrogen atoms contained in the above group (g), group (h) or group (i) may be substituted by a cyano group, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group or a chlorine atom,

[0282] L 41 , L 42 , L 43 , L 44 , L 45 , L 46 , L 47 , L 48 and L 49 Independently represent a single bond, -COO-, -OCO-, -CH 2 CH 2 -、-(CH 2 ) 4 -、-OCH 2 -、-CH 2 O-、-OCF 2 -、-CF 2 O- or -C≡C-, there are multiple 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 They can be the same or different.

[0283] 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, 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 48 Any of represents a fluorine atom, but X 46 and X47 do not simultaneously represent a fluorine atom, X 46 and X 48 do not simultaneously represent a fluorine atom, G represents a methylene group or -O-,

[0284] 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.)

[0285] 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 are preferably each independently 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 (also including a group in which one methylene group or two or more non-adjacent methylene groups present in these groups are substituted with -O- or -S-, and also including a group 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, 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 49 are preferably each independently a trans-1,4-cyclohexylene group (also including a group in which one methylene group or two or more non-adjacent methylene groups present in this group are substituted with -O- or -S.), a 1,4-phenylene group (also including a group in which one -CH= or two or more non-adjacent -CH= present in this group are substituted with -N=), a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-2,5-diyl group, a naphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group and a decahydronaphthalene-2,6-diyl group (also including a group in which the hydrogen atoms contained in each group are 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, a 1,4-phenylene group, a 3-fluoro-1,4-phenylene group or a 2,3-difluoro-1,4-phenylene group, further preferably a trans-1,4-cyclohexylene group or a 1,4-phenylene group, particularly preferably a trans-1,4-cyclohexylene group. L 41 , L42 , L 43 , L 44 , L 45 , L 46 , L 47 , L 48 and L 49 are preferably, independently of one another, a single bond, -CH 2 CH 2 -, -(CH 2 ) 4 -, -OCO-, -COO-, -OCH 2 ( 2 O-, -OCF 2 ( 2 O- or -C≡C-, more preferably a single bond, -CH 2 CH 2 ( 2 O-, -OCH 2 ( 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-, and u, v, w, x, y and z each independently represent 0, 1 or 2, with u + v, w + x and y + z being 2 or less.

[0286] In the structures formed by combinations of the above options, -CH=CH-CH=CH-, -C≡C-C≡C- and -CH=CH-C≡C- are not preferred from the viewpoint of chemical stability. Also, the case where the hydrogen atoms in these structures are replaced by fluorine atoms is not preferred. Also, the formation of structures in which oxygen atoms are connected to each other, sulfur atoms are connected to each other, and sulfur atoms are connected to oxygen atoms is not preferred. Also, the formation of structures in which nitrogen atoms are connected to each other, nitrogen atoms are connected to oxygen atoms, and nitrogen atoms are connected to sulfur atoms is not preferred.

[0287] Among the compounds represented by the general formula (IVa), specifically, the structure represented by the following general formula (IVa-1) is preferred.

[0288] [Chemical formula 65]

[0289]

[0290] (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, L 50 , L51 and L 52 each independently represents a single bond, -CH 2 CH 2 -, -(CH 2 ) 4 -, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 O- or -C≡C-, M 50 represents 1,4-phenylene or trans-1,4-cyclohexylene, u 1 and v 1 each independently represents 0 or 1.)

[0291] More specifically, the structures represented by the following general formula (IVa-2a) to general formula (IVa-3i) are preferably used,

[0292] [Chemical formula 66]

[0293]

[0294] [Chemical formula 67]

[0295]

[0296] (In the formula, R 47 and R 48 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.) R 47 and R 48 each independently is further preferably an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)

[0297] Among the compounds represented by the general formula (IVb), specifically, the structure represented by the following general formula (IVb-1) is preferably used.)

[0298] [Chemical formula 68]

[0299]

[0300] (In the formula, R 49 and R 50 independently of each other 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 52 , L 53 and L 54 each independently represents a single bond, -CH 2 CH 2 -, -(CH 2 ) 4 -, -OCH 2-, -CH 2 O-, -OCF 2 -, -CF 2 O- or -C≡C-, M 51 , M 52 and M 53 represents 1,4-phenylene or trans-1,4-cyclohexylene, w1 and x1 independently represent 0, 1 or 2, and w1 + x1 represents 2 or less.)

[0301] More specifically, the structures represented by the following general formulas (IVb-2a) to (IVb-3f) are preferred.

[0302] [Chemical formula 69]

[0303]

[0304] [Chemical formula 70]

[0305]

[0306] (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.)

[0307] Among the compounds represented by the general formula (IVc), specifically, the structures represented by the following general formulas (IVc-1a) and (IVc-1b) are preferred.

[0308] [Chemical formula 71]

[0309]

[0310] (In the formula, R 51 and R 52 independently of each other 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 represent a single bond, -CH 2 CH 2 -, -(CH 2 ) 4 -, -OCH 2 -, -CH 2 O-, -OCF 2 -, -CF 2 O- or -C≡C-, M 54 , M 55 and M 56represents 1,4-phenylene or trans-1,4-cyclohexylene, y1 and z1 independently represent 0, 1 or 2, and y1 + z1 represents 2 or less.)

[0311] More specifically, they are the following general formulas (IVc-2a) to (IVc-2g).

[0312] [Chemical formula 72]

[0313]

[0314] (In the formula, R 51 and R 52 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.)

[0315] contains at least one compound selected from the group consisting of the compounds represented by general formula (IIIa), general formula (IIIb), and general formula (IIIc) used as the third component or the compounds selected from the group consisting of the compounds represented by general formula (IVa), general formula (IVb), and general formula (IVc), preferably contains 2 to 10 kinds, particularly preferably contains 2 to 8 kinds, the lower limit value of the content rate is preferably 5% by mass, more preferably 10% by mass, 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.

[0316] In the liquid crystal composition containing a polymerizable compound of the present invention, Δn is preferably in the range of 0.08 to 0.25.

[0317] In the liquid crystal composition containing a polymerizable compound of the present invention, regarding Δε, depending on the display mode of the liquid crystal display element, a liquid crystal composition having positive or negative Δε can be used. In a liquid crystal display element in the VA mode, a liquid crystal composition having negative Δε is used. In this case, Δε is preferably -1 or less, more preferably -2 or less.

[0318] The liquid crystal composition containing a polymerizable compound 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), and 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. In the liquid crystal composition of the present invention, in addition to the above compounds, nematic liquid crystals, smectic liquid crystals, cholesteric liquid crystals, etc. for STN liquid crystals can also be contained.

[0319] In the present invention, it may be only the polymerizable initiator compound of the present invention, but in order to improve the alignment stability of the liquid crystal, it is preferable to further use in combination a polymerizable compound having a liquid crystal precursor structure. The polymerizable compound may be a known polymerizable compound used in a liquid crystal composition. As an example of the polymerizable compound, it is preferable to contain one or two or more compounds represented by the general formula (P).

[0320] [Chemical formula 73]

[0321]

[0322] (In the above general formula (P), R p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or -Sp p2 -P p2 , one or two or more non-adjacent -CH 2 -s in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO-, and one or two or more hydrogen atoms in the alkyl group may be independently substituted by a cyano group, a fluorine atom or a chlorine atom,

[0323] P p1 and P p2 each independently represent any one of the general formula (P p1 -1) to formula (P p1 -9).

[0324] [Chemical formula 74]

[0325]

[0326] (In the formula, R p11 and R p12 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms, W p11 represents a single bond, -O-, -COO-, an alkylene group having 1 to 5 carbon atoms, t p11 represents 0, 1 or 2. When there are multiple R p11 , R p12 , W p11 and / or t p11 in the molecule, they may be the same or different.)

[0327] Sp p1 and Sp p2 each independently represent a single bond or a spacer group,

[0328] Z p1 and Z p2 each independently represent a single bond, -O-, -S-, -CH 2 -, -OCH2 -, -CH 2 O-, -CO-, -C 2 H 4 -,-COO-,-OCO-,-OCOOCH 2 -,-CH 2 OCOO-,-OCH 2 CH 2 O-,-CO-NR ZP1 -,-NR ZP1 -CO-,-SCH 2 -,-CH 2 S-,-CH=CR ZP1 -COO-,-CH=CR ZP1 -OCO-,-COO-CR ZP1 =CH-,-OCO-CR ZP1 =CH-,-COO-CR ZP1 =CH-COO-,-COO-CR ZP1 =CH-OCO-,-OCO-CR ZP1 =CH-COO-,-OCO-CR ZP1 =CH-OCO-,-(CH 2 ) z -COO-,-(CH 2 ) z -OCO-,-OCO-(CH 2 ) z -,-(C=O)-O-(CH 2 ) z -,-CH=CH-,-CF=CF-,-CF=CH-,-CH=CF-,-CF 2 -,-CF 2 O-,-OCF 2 -,-CF 2 CH 2 -,-CH 2 CF 2 -,-CF 2 CF 2 - or -C≡C- (wherein, z independently represents an integer from 1 to 4, and R ZP1 independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. When there are multiple Rs in the molecule, they may be the same or different. It should be noted that the * in the formula represents the connection point with Sp ZP1 or Sp p1 .) p2 .)

[0329] A p1 and A p2Each independently represents a group selected from the group consisting of the following groups:

[0330] (a p ) 1,4-cyclohexylene (one -CH 2 - or two or more non - adjacent -CH 2 - in this group may be substituted with -O-.)

[0331] (b p ) 1,4-phenylene (one -CH= or two or more non - adjacent -CH= in this group may be substituted with -N=.) and

[0332] (c p ) naphthalenediyl, 1,2,3,4 - tetrahydronaphthalenediyl, decahydronaphthalenediyl, phenanthrene - 2,7 - diyl or anthracene - 2,6 - diyl (one -CH= or two or more non - adjacent -CH= in these groups may be substituted with -N=.)

[0333] A p3 represents a group selected from the group consisting of the above group (a p ), group (b p ), group (c p ) and a single bond,

[0334] In the above group (a p ), group (b p ), and group (c p ), the hydrogen atoms in this group may each independently be substituted with a cyano group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms or -Sp p2 -P p2 .

[0335] m p1 represents 0, 1, 2 or 3. When there are multiple Z p1 , A p2 , Sp p2 and / or P p2 in the molecule, they may be the same or different.

[0336] m p1 is 0 and A p1 is a group other than naphthalenediyl, phenanthrene - 2,7 - diyl or anthracene - 2,6 - diyl, A p3 represents a group other than a single bond.)

[0337] Specific examples of the polymerizable liquid crystal compound represented by the general formula (P) are shown in (P - 2 - 1) to (P - 2 - 25). Here, a and b represent integers from 2 to 10.

[0338] [Chemical 75]

[0339]

[0340] [Chemical 76]

[0341]

[0342] [Chemical 77]

[0343]

[0344] In addition, the liquid crystal composition containing a polymerizable compound of the present invention can polymerize even in the absence of a photoinitiator, but a photoinitiator may also be contained to promote polymerization. Examples of the photoinitiator include benzoin ethers, benzophenones, acetophenones, benzil ketals, acylphosphine oxides, and the like.Particularly preferred are acetophenones and benzil ketals. For example, 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)butan-1-one “Omnirad 369”, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholinophenyl)butan-1-one “Omnirad 379”, 2,2-dimethoxy-1,2-diphenylethan-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-benzoyl oxime)], 2,2-dimethoxy-1,2-diphenylethan-1-one “Irgacure 651”, 1,2-octanedione, 1-[4-(phenylthio)phenyl], 2-(O-benzoyl oxime) “Irgacure OXE01”, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyl oxime) “Irgacure OXE02”, “Irgacure OXE04” (manufactured by BASF Co., Ltd.), “ADEKA ARKLS NCI-831”, “ADEKA ARKLS 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”, “Esacure 1001M”, “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 photo cationic initiator, a photo acid generator can be used.Examples of the photoacid generator include diazobissulfone compounds, triphenylsulfonium compounds, phenylsulfone compounds, sulfonylpyridine compounds, triazine compounds, and diphenyliodonium salt compounds.

[0345] In the liquid crystal composition containing polymerizable compounds of the present invention, other stabilizers may be further added to improve its storage stability. As usable stabilizers, for example, hydroquinones, hydroquinone monoalkyl ethers, tert-butyl catechols, pyrogallols, thiophenols, nitro compounds, β-naphthylamines, β-naphthols, nitroso compounds, hindered phenols such as (AD-1) to (AD-11), and hindered amines other than the present invention can be cited. The addition amount of the stabilizer when used 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 (AD-1) to (AD-11) below.

[0346] [Chemistry 78]

[0347]

[0348] [Chemistry 79]

[0349]

[0350] (Liquid crystal display element)

[0351] The liquid crystal composition of this embodiment is suitable for 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 a PSA type or PSVA type liquid crystal display element.

[0352] Example

[0353] The present invention is further described below with reference to examples, but the present invention is not limited to these examples. The "%" in the compositions of the following examples and comparative examples means "mass %". The purity of the compounds was analyzed by GC or UPLC. The abbreviations of the compounds and the reaction solvents are as follows: tetrahydrofuran (THF), N,N-dimethylformamide (DMF), diazabicycloundecene (DBU), potassium carbonate (K 2 CO 3 ), triethylamine (NEt3), 4,4-dimethylamino-pyridine (DMAP), dibutyltin oxide (Bu2SnO), tetrakistriphenylphosphine palladium (Pd(PPh3)4), 5% palladium on carbon (Pd / C), and diisopropylcarbodiimide (DIC).

[0354] (Example 1) Preparation of Compound (RM-1)

[0355] In a reaction vessel equipped with a stirring device, a cooler, and a thermometer, 20 g of acrylic acid (4'-((tetrahydro-2H-pyran-2-yl)oxy)-[1,1'-biphenyl]-4-yl) ester, 5.9 g of acetylacetone, 4.5 g of DBU, and 200 mL of THF were added, and the mixture was reacted at room temperature for 3 hours. After the reaction was completed, it was cooled, 300 ml of ethyl acetate was added, and the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification was carried out using an alumina column. After distilling off the solvent, it was dissolved in 100 ml of tetrahydrofuran, and 20 ml of 2N hydrochloric acid was added at room temperature, and the mixture was stirred for 6 hours. After the reaction was completed, 200 ml of ethyl acetate was added, and it was washed with water and saturated brine, and the solvent was distilled off. Then, it was dispersed and washed in toluene, and then purified using a silica gel column to obtain 27.1 g of Compound (1).

[0356] [Chemical Formula 80]

[0357]

[0358] Under a nitrogen atmosphere, in a reaction vessel equipped with a stirring device, a thermometer, a condenser, and a Dean-Stark tube, 10 g of the above Compound (1), 5 g of ethyl methacrylate, 200 mg of dibutyltin oxide, and 150 mL of THF were added, and the mixture was heated to reflux for 4 hours to carry out a transesterification reaction. After the reaction was completed, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, it was dispersed and washed in toluene, and then purified using an amino silica gel column to obtain 8.7 g of the target compound (RM-1).

[0359] [Chemical Formula 81]

[0360]

[0361] GC-MS: m / z 717

[0362] Melting point: 144 °C

[0363] 1 H-NMR (solvent: deuterated chloroform): δ: 2.04 - 2.07 (m, 6H), 2.22 (s, 6H), 2.37 - 2.54 (m, 8H), 5.75 - 5.77 (m, 2H), 6.34 - 6.37 (m, 2H), 7.13 - 7.27 (m, 8H), 7.53 - 7.56 (m, 8H)

[0364] (Example 2) Preparation of Compound (RM-2)

[0365] In a reaction vessel equipped with a stirring device, a cooler and a thermometer, 10 g of the above compound (1), 4.3 g of triethylamine, 4.5 g of acryloyl chloride and 100 mL of dichloromethane were added, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed, the organic layer was washed with saturated ammonium chloride solution, water and saturated brine, the solvent was distilled off, and the concentrate was purified by an alumina column to obtain 9.1 g of the target compound (RM-2).

[0366] [Chemical formula 82]

[0367]

[0368] GC-MS: m / z 689

[0369] Melting point: 144 °C

[0370] 1 H-NMR (solvent: deuterated chloroform): δ: 2.21 (s, 6H), 2.38 - 2.52 (m, 8H), 6.00 (m, 1H), 6.03 (m, 1H), 6.30 - 6.40 (m, 2H), 6.59 (m, 1H), 6.64 (m, 1H), 7.12 - 7.22 (m, 8H), 7.50 - 7.59 (m, 8H)

[0371] The same reaction as in Example 1 and a method based on a known method as needed were used to produce Examples 3 to 9 through the following synthetic route.

[0372] (Example 3) Production of compound (RM-3)

[0373] [Chemical formula 83]

[0374]

[0375] GC-MS: m / z 772

[0376] (Example 4) Production of compound (RM-4)

[0377] [Chemical formula 84]

[0378]

[0379] GC-MS: m / z 804

[0380] (Example 5) Production of compound (RM-5)

[0381] [Chemical formula 85]

[0382]

[0383] GC-MS: m / z 632

[0384] (Example 6) Preparation of Compound (RM-6)

[0385] [Chemical Formula 86]

[0386]

[0387] GC-MS: m / z 420

[0388] (Example 7) Preparation of Compound (RM-7)

[0389] [Chemical Formula 87]

[0390]

[0391] GC-MS: m / z 572

[0392] (Example 8) Preparation of Compound (RM-8)

[0393] [Chemical Formula 88]

[0394]

[0395] GC-MS: m / z 750

[0396] (Example 9) Preparation of Compound (RM-9)

[0397] [Chemical Formula 89]

[0398]

[0399] GC-MS: m / z 750

[0400] <Preparation and Evaluation of Liquid Crystal Composition>

[0401] For the description of the compounds in the following examples, the following abbreviations are used.

[0402] (Side chain)

[0403] -n -C n H 2n+1 Straight-chain alkyl group with n carbon atoms

[0404] n- C n H 2n+1 - Straight-chain alkyl group with n carbon atoms

[0405] -On -OC n H 2n+1 Straight-chain alkoxy group with n carbon atoms

[0406] nO- C n H 2n+1A linear alkoxy group having n carbon atoms in the O-atom chain

[0407] -V -CH=CH 2

[0408] V- CH 2 =CH-

[0409] -V1 -CH=CH-CH 3

[0410] 1V- CH 3 -CH=CH-

[0411] -F -F

[0412] -OCF3 -OCF 3

[0413] (Linking group)

[0414] -1O- -CH 2 -O-

[0415] -O1- -O-CH 2 -

[0416] -2- -CH 2 -CH 2 -

[0417] -COO- -COO-

[0418] -OCO- -OCO-

[0419] - Single bond

[0420] (Ring structure)

[0421] [Chemical formula 90]

[0422]

[0423] In the examples, the measured properties are as follows.

[0424] T ni : Nematic-isotropic liquid phase transition temperature (°C)

[0425] Δn: Refractive index anisotropy at 20°C

[0426] η: Viscosity at 20°C (mPa·s)

[0427] γ 1 : Rotational viscosity at 20°C (mPa·s)

[0428] Δε: Dielectric constant anisotropy at 20°C

[0429] K33 : Elastic constant K at 20 °C 33 (pN)

[0430] (Method for manufacturing liquid crystal display element)

[0431] First, a liquid crystal composition containing a polymerizable compound is injected into a liquid crystal cell including a substrate with ITO and having a cell gap of 3.5 μm by a vacuum injection method. The substrate with ITO is coated with a polyimide alignment film that induces vertical alignment and is subjected to rubbing treatment.

[0432] Then, the liquid crystal cell injected with the liquid crystal composition containing the polymerizable compound is irradiated with ultraviolet rays for 90 minutes using a fluorescent UV lamp to obtain a liquid crystal display element. At this time, the fluorescent UV lamp is adjusted so that the illuminance measured under the condition of a central wavelength of 313 nm becomes 3 mW / cm 2 .

[0433] (Evaluation method for residual amount of polymerizable compound)

[0434] The residual amount [ppm] of the polymerizable compound in the liquid crystal display element after irradiating with ultraviolet rays for 150 seconds under the above irradiation conditions is measured. The measurement method of the residual amount of the polymerizable compound is described. First, the decomposed liquid crystal display element and acetonitrile are placed in a test tube, shaken and filtered to obtain an acetonitrile solution containing the eluted components of the liquid crystal composition, polymer, and unreacted polymerizable compound. It is analyzed by high performance liquid chromatography, and the peak areas of each component are calculated. Based on the ratio of the peak area of the liquid crystal compound used as an index to the peak area of the unreacted polymerizable compound and the amount of the polymerizable compound initially added, the residual amount of the polymerizable compound is determined. It should be noted that the detection limit of the residual amount of the polymerizable compound is 100 ppm.

[0435] (Evaluation method for pretilt angle)

[0436] First, the pretilt angle of the liquid crystal cell injected with the liquid crystal composition containing the polymerizable compound is measured as the pretilt angle (before ultraviolet irradiation). A voltage of 10 V is applied to this liquid crystal cell at a frequency of 100 Hz, and at the same time, it is irradiated with ultraviolet rays for 150 seconds under the above irradiation conditions. Then, the pretilt angle is measured as the pretilt angle (after ultraviolet irradiation). The value obtained by subtracting the pretilt angle (after ultraviolet irradiation) from the measured pretilt angle (before ultraviolet irradiation) is used as the pretilt angle change amount [°] caused by ultraviolet irradiation. The pretilt angle is measured using OPTIPRO manufactured by Shintec.

[0437] (Evaluation method for VHR)

[0438] For a liquid crystal cell injected with a liquid crystal composition containing a polymerizable compound, ultraviolet rays are irradiated for 60 minutes under the above irradiation conditions, and the VHR is measured under the conditions of 1 V, 0.6 Hz, and 60 °C. When the value is 95% or more, it is denoted as A; when it is less than 95% and 90% or more, it is denoted as B; when it is less than 90% and 80% or more, it is denoted as C; and when it is less than 80%, it is denoted as D.

[0439] (Modulation and evaluation results of liquid crystal compositions)

[0440] Liquid crystal compositions of LC-001 to LC-008 were prepared, and their physical property values were measured. The compositions of the liquid crystal compositions and the results of their physical property values are shown in Table 1.

[0441] [Table 1]

[0442] LC-001 LC-002 LC-003 LC-004 LC-005 LC-006 LC-007 LC-008 3-Cy-Cy-2 18 20 20 18.5 20 3-Cy-Cy-4 8 4 4 3-Cy-Cy-5 6.75 7 3-Cy-Cy-V 29 23 29 3-Cy-Cy-V1 10 10.25 3-Cy-Ph-O1 6 4 3 3-Ph-Ph-1 13 17 12 10 9 3-Cy-Cy-Ph-1 6 7 7 3-Cy-Cy-Ph-3 4 4 3-Cy-Ph-Ph-1 7 5 5 3-Cy-Ph-Ph-2 6 4 5 5-Cy-Ph-Ph-2 4 1V2-Ph-Ph-1 3.75 3-Cy-Ph5-O2 11.5 3-Ph-Ph5-O2 12 5 12 10 10 3-Cy-Cy-Ph5-1 2.5 3-Cy-Cy-Ph5-O1 12 3-Cy-Cy-Ph5-O2 15 15 3-Cy-Cy-Ph5-O4 15 15 4-Cy-Cy-Ph5-O2 10 13 3-Cy-1O-Ph5-O1 6 3-Cy-1O-Ph5-O2 7 6 9 5 1V-Cy-1O-Ph5-O2 6 2-Cy-Cy-1O-Ph5-O2 14 12 3-Cy-Cy-1O-Ph5-O2 3 15 10 12 12 V-Cy-Cy-1O-Ph5-O2 4 1V-Cy-Cy-1O-Ph5-O2 5 5 5 6 2-Cy-Ph-Ph5-O2 7 10 6 5 5 3-Cy-Ph-Ph5-O2 8 10 5 10.75 4 2 3-Cy-Ph-Ph5-O3 6 3-Cy-Ph-Ph5-O4 7 9 4-Cy-Ph-Ph5-O3 8 3-Ph-Ph5-Ph-2 5 2-Ph-2-Ph-Ph5-O2 5 3-Ph-2-Ph-Ph5-O2 5 5 8 Total (wt%) 100 100 100 100 100 100 100 100 Tni [℃] 73.8 74.4 76.7 76.2 72.8 74.7 111.2 110.2 Δn 0.111 0.112 0.118 0.128 0.114 0.103 0.098 0.098 Δε -3.2 -2.8 -3.3 -3.4 -3.3 -3.1 -3.1 -3.1 Y1 [mPa·s] 125 105 132 134 104 99 154 135

[0443] (Comparative Examples 1 to 12)

[0444] As Comparative Examples 1 and 2, 3000 ppm of the polymerizable compound (RM-R1) was added to the liquid crystal compositions (LC-001) and (LC-002), respectively, to prepare liquid crystal compositions. In addition, as Comparative Examples 3 to 10, 2700 ppm of the polymerizable compound (RM-R1) and 300 ppm of the initiator compound (R-1) were added to the liquid crystal compositions (LC-001) to (LC-008), respectively, to prepare liquid crystal compositions. In addition, as Comparative Examples 11 and 12, 2700 ppm of the polymerizable compound (RM-R1) and 300 ppm of the polymerizable initiator compound (R-2) were added to the liquid crystal compositions (LC-001) and (LC-002), respectively, to prepare liquid crystal compositions. These liquid crystal compositions were respectively injected into liquid crystal cells, and the above various evaluations were carried out. The evaluation results of Comparative Examples 1 to 12 are shown in Table 2.

[0445] [Chemical Formula 91]

[0446]

[0447] (Examples 10 to 37)

[0448] As Examples 10 to 18, with respect to the liquid crystal composition (LC-001), 2700 ppm of the above polymerizable compound (RM-R1) was added, and further 300 ppm of the polymerizable initiator compounds (RM-1) to (RM-9) obtained in Examples 1 to 9 were respectively added to prepare a liquid crystal composition. In addition, as Examples 19 to 27, with respect to the liquid crystal composition (LC-002), 2700 ppm of the above polymerizable compound (RM-R1) was added, and further 300 ppm of the above polymerizable initiator compounds (RM-1) to (RM-9) were respectively added to prepare a liquid crystal composition. In addition, as Examples 28 to 33, with respect to the liquid crystal compositions (LC-003) to (LC-008), 2700 ppm of the above polymerizable compound (RM-R1) and 300 ppm of the above polymerizable initiator compound (RM-1) were added to prepare a liquid crystal composition. In addition, as Examples 34 to 37, with respect to the liquid crystal compositions (LC-001) and (LC-002), 3000 ppm of the above polymerizable compound (RM-R1) and 1000 ppm of the above polymerizable initiator compound (RM-1) or (RM-2) were added to prepare a liquid crystal composition. In addition, as Examples 38 to 41, with respect to the liquid crystal compositions (LC-001) and (LC-002), 2700 ppm of the above polymerizable compound (RM-R2) or (RM-R3) and 300 ppm of the above polymerizable initiator compound (RM-1) were added to prepare a liquid crystal composition. These liquid crystal compositions were respectively injected into liquid crystal cells, and the above various evaluations were carried out. The evaluation results of Examples 10 to 41 are shown in Table 2.

[0449] [Table 2]

[0450]

[0451] Among Examples 10 to 41 of the liquid crystal composition containing the polymerizable initiator compound of the present invention, the residual amount of the polymerizable compound after ultraviolet irradiation was less than that of Comparative Examples 1 to 12, and it was found that the polymerization rate of the polymerizable compound was sufficiently fast. In addition, the amount of change in the pretilt angle caused by ultraviolet irradiation was shown to be greater than that of Comparative Examples 1 to 12, and it was found that the pretilt angle could be formed in a short time. In addition, it was confirmed that the VHR after ultraviolet irradiation was sufficiently high.

[0452] From this result, it can be seen that the compound of the present application invention has the following effects: without impairing the reliability of the liquid crystal composition, the polymerization rate is sufficiently fast, and in addition, the pretilt angle can be formed in a shorter ultraviolet irradiation time.

Claims

1. A compound, characterized in that it is selected from one of the compounds represented by Formula RM-1 to Formula RM-9:

2. A liquid crystal composition containing one or more of the compounds described in claim 1.

3. The liquid crystal composition according to claim 2, containing one or more polymerizable compounds A having a structure different from that of the compound described in claim 1.

4. The liquid crystal composition according to claim 3, containing one or more polymerizable compounds represented by the general formula (P) as the polymerizable compound A, [Chemical formula 3] In the above general formula (P), R p1 represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or -Sp p2 -P p2 , one or two or more non-adjacent -CH 2 - in the alkyl group may be independently substituted by -CH=CH-, -C≡C-, -O-, -CO-, -COO- or -OCO- respectively, and one or two or more hydrogen atoms in the alkyl group may be independently substituted by a cyano group, a fluorine atom or a chlorine atom. P p1 and P p2 each independently represents any one of the general formulas (P p1 -1) to formula (P p1 -9). [Chemical formula 4] In the formula, R p11 and R p12 each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogenated alkyl group having 1 to 5 carbon atoms, W p11 represents a single bond, -O-, -COO-, an alkylene group having 1 to 5 carbon atoms, t p11 represents 0, 1 or 2. When there are a plurality of R p11 , R p12 , W p11 and / or t p11 in the molecule, they may be the same or different. Sp p1 and Sp p2 each independently represents a single bond or a spacer group, Z p1 and Z p2 each independently represents a single bond, -O-, -S-, -CH 2 -, -OCH 2 -, -CH 2 O-, -CO-, -C 2 H 4 -, -COO-, -OCO-, -OCOOCH 2 -, -CH 2 OCOO-, -OCH 2 CH 2 O-, -CO-NR ZP1 -, -NR ZP1 -CO-, -SCH 2 -, -CH 2 S-, -CH=CR ZP1 -COO-, -CH=CR ZP1 -OCO-, -COO-CR ZP1 =CH-, -OCO-CR ZP1 =CH-, -COO-CR ZP1 =CH-COO-, -COO-CR ZP1 =CH-OCO-, -OCO-CR ZP1 =CH-COO-, -OCO-CR ZP1 =CH-OCO-, -(CH 2 ) z -COO-, -(CH 2 ) z -OCO-, -OCO-(CH 2 ) z -, -(C=O)-O-(CH 2 ) z -, -CH=CH-, -CF=CF-, -CF=CH-, -CH=CF-, -CF 2 -, -CF 2 O-, -OCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 - or -C≡C-, where z each independently represents an integer from 1 to 4, and R ZP1 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. When there are multiple Rs in the molecule, they can be the same or different, ZP1 ​ wherein The * in the formula represents the connection point with Sp p1 or Sp p2 , A p1 and A p2 each independently represents a group selected from the group consisting of the following groups, (a p ) 1,4 - cyclohexylene, one -CH 2 - or two or more non - adjacent -CH 2 - may be substituted with -O-; (b p )1,4-phenylene, in which one -CH= or two or more non-adjacent -CH= present in the group may be replaced by -N=; and (c p ) a naphthalenediyl, 1,2,3,4-tetrahydronaphthalenediyl, decahydronaphthalenediyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl, and one —CH═ or two or more non-adjacent —CH═ present in these groups may be substituted with —N═, A p3 represents a group selected from the group consisting of the above-mentioned group (a p ), group (b p ), and group (c p ), and a single bond The above-mentioned group (a p ), group (b p ), and group (c p ), the hydrogen atoms present in the group are each independently capable of being substituted by a cyano group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, or -Sp p2 -P p2 substituted, m p1 represents 0, 1, 2 or 3, and there are multiple Zs in the molecule p1 , A p2 , Sp p2 and / or P p2 when they are present, they may be the same or different m p1 is 0 and A p1 is a group other than a naphthalene diyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl group, A p3 represents a group other than a single bond.

5. A liquid crystal display element using the liquid crystal composition according to any one of claims 2 to 4.

6. An active matrix drive liquid crystal display element using the liquid crystal composition according to any one of claims 2 to 4.

7. A liquid crystal display element for PSA mode, PSVA mode, PS-IPS mode or PS-FFS mode, using the liquid crystal composition according to any one of claims 2 to 4.

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