JP2020196827A - Liquid crystal composition and liquid crystal display element - Google Patents

Abstract

To provide a liquid crystal composition that less likely causes changes in a pretilt angle and reduction in a voltage retention rate when a display element using no alignment film layers is fabricated, and to provide a display element using the liquid crystal composition.SOLUTION: The liquid crystal composition of the present invention comprises a compound (A) having a hydroxyl group and an ester structure in the molecular structure, and a compound (B) having a group selected from a hydroxyl group, an amino group and a mercapto group, and a dioxane structure in the molecular structure, in which the compound (A) and the compound (B) have different molecular structures from each other.SELECTED DRAWING: None

Description

The present invention relates to a liquid crystal composition and a liquid crystal display element.

Liquid crystal displays typified by the VA type, PSA type, and PSVA type exhibit a black display associated with vertical orientation when no voltage is applied, while a white display associated with horizontally tilted uniformly when a voltage is applied. is there. In a conventional liquid crystal display, in order to stably switch between these black display and white display in a pixel, it is currently essential to provide a special layer called a polyimide alignment film layer on the electrode. However, in recent years, panel makers have merits such as cost reduction for forming the alignment film layer, environmental consideration, and narrowing of the frame, so that the alignment of the liquid crystal molecules can be realized while omitting the alignment film layer. Various methods have been studied.

For example, Patent Document 1 discloses a liquid crystal medium based on a mixture of polar compounds having a negative dielectric anisotropy and containing at least one kind of spontaneous orientation additive, and the liquid crystal medium is described. It is described that it is suitable for use in a display element that does not contain any alignment layer. Then, in Patent Document 1, a compound having an alcohol structure is used as the spontaneous orientation additive. Examples of spontaneously oriented additives into which a polymerizable group is further introduced in order to further stabilize the vertical orientation of the liquid crystal molecules have been reported (Patent Documents 2 to 4). Then, in these documents, a compound having an alcohol structure and a (meth) acrylic group in the molecule is used as a spontaneous orientation additive. However, these compounds having an alcohol structure and a (meth) acrylic group in the molecule have a problem that they easily cause an intramolecular transesterification reaction between the (meth) acrylic group and the alcohol moiety. The intramolecular transesterification reaction is more likely to proceed in a fluid medium such as a liquid crystal composition. Further, when these compounds having an alcohol structure and a (meth) acrylic group in the molecule are added to the liquid crystal composition to prepare a display element, an intramolecular transesterification reaction occurs due to the influence of ambient temperature and ultraviolet rays. It will progress further. In particular, there is a problem that the reaction is catalyzed by a trace amount of metal component eluted from other members in contact with the liquid crystal composition in the display element, and the intramolecular transesterification is accelerated. When such an intramolecular transesterification reaction occurs in a display element, there is a problem that the pretilt angle of the liquid crystal molecule changes with time, and the voltage retention rate decreases due to impurities generated by the side reaction. there were. When such a liquid crystal display element is used, there is a problem that the quality of the product is deteriorated due to changes in color, viewing angle, seizure, etc. due to long-term use. Therefore, there has been a demand for the development of a liquid crystal composition that can solve such a problem.

Special Table 2014-524951 JP-A-2015-168826 Special Table 2018-534380 JP-A-2018-090569

An object to be solved by the present invention is to provide a liquid crystal composition in which a change in a pretilt angle and a decrease in a voltage retention rate are unlikely to occur when a display element that does not use an alignment film layer is manufactured. Another object of the present invention is to provide a display element using the liquid crystal composition.

As a result of diligent research to solve the above problems, the present inventors have developed the following liquid crystal composition. That is, the present invention comprises a compound (A) having a hydroxyl group and an ester structure in its molecular structure, and a compound (B) having a group selected from a hydroxyl group, an amino group, a mercapto group and a carboxyl group and a dioxane structure in its molecular structure. A liquid crystal composition containing the above, wherein the compound (A) and the compound (B) have different molecular structures, and a display element using the liquid crystal composition is also provided.

The liquid crystal composition of the present invention is useful as a material for a liquid crystal display element that does not use an alignment film layer because changes in the pretilt angle and a decrease in the voltage holding ratio are unlikely to occur.

The present invention contains a compound (A) having a hydroxyl group and an ester structure in its molecular structure, and a compound (B) having a group selected from a hydroxyl group, an amino group, a mercapto group and a carboxyl group and a dioxane structure in its molecular structure. Here, a liquid crystal composition having a different molecular structure between the compound (A) and the compound (B) is provided, and a display element using the liquid crystal composition is also provided.

<Compound (A)>
The compound (A) has a hydroxyl group. The hydroxyl group in the compound (A) is a member (electrode (for example, ITO), substrate (for example, glass substrate, acrylic substrate, transparent substrate, flexible) that directly contacts the liquid crystal layer containing the liquid crystal composition in the display element. It interacts with (eg, substrate, etc.), resin layer (eg, color filter, alignment film, overcoat layer, etc.), insulating film (eg, inorganic material film, SiNx, etc.), and as a result, the above compound (A) It has a function of inducing homeotropic orientation or homogeneous orientation of liquid crystal molecules contained in the liquid crystal layer.

In the compound (A), the ester structure is preferably derived from a group polymerized by radical polymerization, cationic polymerization or anionic polymerization, and the following formulas (P-1) to (P-7) are used.

(In the formula, the broken line represents the bond position.) It is more preferable that the group is selected from. When a liquid crystal composition containing a compound having such a polymerization functional group is used, the homeotropic orientation or homogenius orientation of the liquid crystal molecules in the display element is induced, and then the polymerization reaction is carried out to polymerize the liquid crystal composition. The orientation of the liquid crystal is stabilized.

The compound (A) has the following general formula (I).

(Wherein, ^{R a} is the following formula (Ra)

(In the formula, the broken line represents the bond position.)
R ¹ is hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino. A group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one or more -CH _2- are independently -O-, -S-, -CO-, -COO-, -OCO-. , -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-,- Linear or linear with 1 to 20 carbon atoms which may be substituted by COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- Although it represents a branched alkyl group, any hydrogen atom in the alkyl group may be substituted with a fluorine atom.
A ¹ , A ² and A ³ are independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine-2,5, respectively. - diyl group, pyrimidine-2,5-diyl group, represent a tetrahydropyran-2,5-diyl group or 1,3-dioxane-2,5-diyl group, the same those ^{if a 1} there are multiple It may be present or different, and A ¹ may be unsubstituted or substituted with one or more substituents L ¹ .
Z ¹ and Z ² are independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, -OCO-, -CO. -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH- COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _2- , -CH ₂ CH ₂ -COO-, -CH ₂ CH _2- OCO-, -COO-CH _2- , -OCO-CH _2- , -CH _2- COO-, -CH ₂ -OCO-, -CH = CH-, -N = N -, - CH = N - , - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, ^{if Z 1} there are a plurality of They can be the same or different,
L ¹ , L ² , L ³ and L ⁴ are independently fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group and mercapto group. , Methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyanogroup, or one or more -CH _2- independently -O-, -S-,- CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO- , -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- may be substituted carbon Although the atoms 1 represents a linear or branched alkyl group of 20, any hydrogen atom in the alkyl group may be substituted by fluorine atoms, they if L ¹ there are a plurality had the same be different even better, if L ² there are a plurality thereof may be the same or different and they if L ³ there are a plurality may be the same or different and L ⁴ When there are a plurality of them, they may be the same or different, and L ⁴ may represent a hydrogen atom or a group represented by −Sp ⁷ −OH.
P ¹ , P ² and P ³ each independently represent a group selected from the above formulas (P-1) to (P-7), but if there are a plurality of P ^1, they may be the same. may be different, if the P ² there are a plurality thereof may be the same or different and they if P ³ there are a plurality may be the same or different and
Sp ¹ , Sp ² , Sp ³ , Sp ⁴ , Sp ⁶ and Sp ⁷ each independently represent a spacer group or a single bond, but if there are multiple Sp ^1, they may be the same or different. , If there are a plurality of Sp ^2, they may be the same or different, if there are a plurality of Sp ^3, they may be the same or different, and if there are a plurality of Sp ⁷ , they may be different. It can be the same or different
Sp ⁵ represents a tetravalent group and represents
m1 represents 0, 1, 2 or 3
k1 and k2 independently represent integers from 0 to 4, respectively.
r1 and r2 each independently represent an integer from 0 to 4, but k1 + r1 represents an integer from 0 to 4, and k2 + r2 represents an integer from 0 to 4.
k3 represents 0, 1 or 2,
r3 represents 0, 1 or 2, while k3 + r3 represents 2, but k1 + k2 + k3 represents an integer from 1 to 6. ) Is preferable.

In the general formula (I), R ¹ is hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino. A group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one or more -CH ₂ − independently of -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH The number of carbon atoms which may be substituted by = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- 1 Represents a linear or branched alkyl group from 20 to 20, but any hydrogen atom in the alkyl group may be substituted with a fluorine atom. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystal properties, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, R ¹ is a hydrogen atom, a fluorine atom, a chlorine atom, A pentafluorosulfanyl group, a nitro group, a cyano group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or any hydrogen atom in the group may be substituted with a fluorine atom, and one or more atoms may be substituted. -CH _2- independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-,- CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-,- CF = CF- or preferably represents a linear or branched alkyl group having from good 1 -C be replaced 20 by -C≡C-, R ¹ is a hydrogen atom, a fluorine atom, a chlorine atom, Any hydrogen atom in the group may be replaced with a fluorine atom, and one or more −CH ₂ −s are independently −O−, −CO−, −COO−, −OCO−, −CO−. NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = It is more preferable to represent a linear or branched alkyl group having 1 to 18 carbon atoms which may be substituted by CF- or −C≡C−, and in R ¹ , any hydrogen atom in the group is a fluorine atom. may be substituted with one or more -CH ₂ - are each independently -O -, - CO -, - COO- or which may have been the good 1 to 18 carbon atoms substituted by -OCO- More preferably, it represents a linear or branched alkyl group, where R ¹ is a carbon in which one or more −CH ₂ −s may be independently substituted with −O−, −COO− or −OCO−, respectively. It is even more preferable to represent a linear or branched alkyl group having 1 to 8 atoms, and R ¹ is a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms. Is particularly preferable.

In the general formula (I), A ¹ , A ² and A ³ are independently 1,4-phenylene group, 1,4-cyclohexylene group and bicyclo [2.2.2] octane-1,4-diyl, respectively. group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, represent a tetrahydropyran-2,5-diyl group or 1,3-dioxane-2,5-diyl group, ^{a 1} is more If present, they may be the same or different, and A ¹ may be unsubstituted or substituted with one or more substituents L. Ease of synthesis, availability of raw materials ease, liquid, storage stability, in terms of stability and voltage holding ratio of the pre-tilt angle of the case of manufacturing a display device, A ¹ is them if there are multiple was in the same It is different at best, unsubstituted or substituted with one or more substituents L may be substituted by ¹ 1,4-phenylene group, 1,4-cyclohexylene group, tetrahydropyran-2,5 - preferably represents an diyl group or 1,3-dioxane-2,5-diyl group, a ¹ is them if there are a plurality may be the same or different and the following formula (a-1) Formula (A-11)

(In the equation, the broken line represents the bonding position, and when a plurality of L ^1s are present, they may be the same or different.) It is more preferable to represent a group selected from the above, and when a plurality of A ^1s are present. They may be the same or different, more preferably they represent a group selected from formulas (A-1) to (A-7), and if there are more than ^one A1, they are the same. may be the or different, even more preferably represents a group selected from the formulas (a-1) from the formula (a-4), they if a ¹ is more present or not be the same or different It is particularly preferable to represent a group selected from the formulas (A-1) and (A-2). In addition, A ² and A ³ independently form a 1,4-phenylene group, a 1,4-cyclohexylene group, a tetrahydropyran-2,5-diyl group, or a 1,3-dioxane-2,5-diyl group, respectively. It is preferable to represent, and A ² and A ³ each independently represent a group selected from the above formulas (A-1), formula (A-2), formula (A-8) and formula (A-9). It is even more preferable that A ² and A ³ each independently represent a group selected from the formulas (A-1) and (A-2), and A ² is the formula (A-1) and. represents a group selected from the formulas (a-2), a ³ is particularly preferably represents a group represented by the formula (a-1).

In the general formula (I), Z ¹ and Z ² are independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, respectively. , -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-,- NH-CO-NH-, -NH-O-, -O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF ₂ -, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH ₂ -, -CH ₂ CH _2- COO-, -CH ₂ CH _2- OCO-, -COO-CH _2- , -OCO-CH _2- , -CH ₂ -COO-, -CH _2- OCO-, -CH = CH-, -N = N-, -CH = N-, -N = CH-, -CH = N-N = CH-, -CF = CF-, -C≡C- or a single bond, If Z ¹ there are a plurality thereof may be different even in the same. From the viewpoints of ease of synthesis, ease of obtaining raw materials, liquidity, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, Z ¹ and Z ² have a plurality of Z ^1. If they are the same or different, they are independently -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -COO-, -OCO-, -CO-NH-, -NH-CO-, -CF ₂ O-, -OCF _2- , -CH = CH-COO-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _{2- , -CH 2 CH 2 -COO -,} - CH 2 CH 2 -OCO -, - CH = CH -, - CF = CF -, - C≡C- or preferably a single bond, ^{Z 1} and ^{Z 2} If there are multiple Z ^1, they may be the same or different, and they are independently -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -COO-, -OCO-. _{, -CF 2 O -, - OCF} 2 -, - COO-CH 2 CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO- or a single bond more preferably represents an, ^{Z 1} and ^{Z 2} may be the be the same or different they ^{if Z 1} there are a plurality, each independently _{-OCH 2 -, - CH 2 O} -, - CH _{2 CH 2 -, - COO -} , - OCO -, - CF 2 O -, - OCF 2 - or more preferably a single bond, ^{Z 1} and ^{Z 2} are the same those cases ^{where Z 1} there are a plurality of It may be present or different, and it is even more important to independently represent -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CF ₂ O-, -OCF _2- or a single bond. preferably, Z ¹ and Z ² are those when the Z ¹ there are a plurality may be the same or different and are particularly preferably a single bond.

The polymerizable group of the compound represented by the general formula (I) is preferably polymerized by light irradiation. Therefore, it is preferable that the compound represented by the general formula (I) has an absorption spectrum corresponding to the wavelength of the lamp used, or is used in combination with another component having a sensitizing effect. When the light resistance of the display element is particularly important, it is preferable that the compound represented by the general formula (I) has the above absorption spectrum and the long wavelength end of the absorption spectrum is as short as possible. For that purpose, it is preferable to have a minimum degree of conjugation having an absorption spectrum corresponding to the wavelength of the lamp used. For example, a preferred structure of the mesogen moiety of the compound represented by the general formula (I) is a terphenyl structure in which one or more aliphatic rings may be further bonded, and one or more aliphatic rings are further bonded. Examples thereof include a biphenyl structure which may be used and a phenyl structure in which one or more aliphatic rings may be further bonded.

In the general formula (I), L ¹ , L ² , L ³ and L ⁴ are independently fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group and amino. Group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one or more -CH _2- each independently -O -, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, By -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- It represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and a plurality of L ^1s are present. may they have be the same or different when you, they if L ² there are a plurality may be the same or different and they if L ³ there are a plurality be the same or different even if well, when L ⁴ is plurality of them may be the same or different and also, L ⁴ may represent a group represented by hydrogen or -Sp 7 ^-OH. Ease of synthesis, availability of raw materials ease, liquid, storage stability, in terms of stability and voltage holding ratio of the pre-tilt angle of the case of manufacturing a display device, L ^1, L ² and L ³ has L ¹ If there are a plurality of them, they may be the same or different, if there are a plurality of L ^2, they may be the same or different, and if there are a plurality of L ^3, they may be the same. Can be different, each independently of a fluorine atom, a chlorine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or any of the groups. The hydrogen atom may be replaced with a fluorine atom, and one or more −CH ₂ −s are independently −O−, −S−, −CO−, −COO−, −OCO−, −CO−S. -, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH A linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted with −, −OCO−CH = CH−, −CH = CH−, −CF = CF− or −C≡C−. preferably representing, L ^1, L ² and L ³ may be different even if the same they If L ¹ there are a plurality, they if L ² there are a plurality or different may be the same at best, if the L ³ there are a plurality thereof may be the same or different and each independently a fluorine atom, a chlorine atom, or have any hydrogen atom in the group is substituted by fluorine atoms One or more −CH ₂₋ may be independently −O−, −CO−, −COO−, −OCO−, −CO-NH−, −NH—CO−, −CH = CH−. Even if substituted by COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- It is more preferable to represent a good linear or branched alkyl group having 1 to 20 carbon atoms, and L ¹ , L ² and L ³ may be the same or different when a plurality of L ^1s are present. well, if L ² there are a plurality thereof may be different even in the same, L ³ is those when there are a plurality of which may be the same or different and each independently a fluorine atom, or , Any hydrogen atom in the group may be replaced with a fluorine atom, and one or more −CH ₂₋ are independent of each other. It is more preferable to represent a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted with −O−, −CO−, −COO− or −OCO−, and L ¹ , L ² and L ³ may be the same or different when a plurality of L ^1s are present, they may be the same or different when a plurality of L ^2s are present, and they may be the same or different when a plurality of L ^3s are present. They may be the same or different, and each independently represents a fluorine atom, a linear alkyl group having 1 to 8 carbon atoms or a linear alkoxy group having 1 to 7 carbon atoms. more preferably, L ^1, L ² and L ³ may be different even if the same they If L ¹ there are a plurality, even those cases where L ² there are a plurality optionally be the same or different well, if L ³ there are a plurality thereof may be the same or different and each independently a fluorine atom, a methyl group, an ethyl group, a propyl group, and particularly preferably a methoxy group or an ethoxy group. Further, L ⁴ is them if there are a plurality may be the same or different and hydrogen atom, a fluorine atom, a chlorine atom, pentafluorosulfanyl group, a nitro group, a cyano group, methylamino group, dimethylamino group, A diethylamino group, a diisopropylamino group, or any hydrogen atom in the group may be substituted with a fluorine atom, and one or more -CH ₂ -are independently -O-, -S-, and -CO. -, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, Carbon atoms that may be substituted by −CH = CH-OCO−, −COO−CH = CH−, −OCO−CH = CH−, −CH = CH−, −CF = CF− or −C≡C− linear or branched alkyl group containing from 1 to 20, or preferably represents a group represented by -Sp 7 ^-OH, L ⁴ is them if there are a plurality may be different even in the same , Hydrogen atom, fluorine atom, chlorine atom, or any hydrogen atom in the group may be replaced with fluorine atom, and one or more -CH ₂ − are independently -O-, -CO-, respectively. , -COO-, -OCO-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = A linear or branched alkyl group having 1 to 20 carbon atoms, which may be substituted by CH-, -CH = CH-, -CF = CF- or -C≡C-, or -Sp ^7- OH. it is more preferably a group represented, L ⁴ is them if there are a plurality may be the same or different and hydrogen atom, a fluorine atom, or, in any hydrogen atom fluorine atom in the group It may be substituted, and one or more −CH ₂₋ may be independently substituted by −O−, −CO−, −COO− or −OCO−, respectively, directly having 1 to 12 carbon atoms. more preferably represent a linear or branched alkyl group, or a group represented by -Sp 7 ^-OH, L ⁴ is them if there are a plurality may be the same or different and hydrogen atom, or A linear or branched alkyl group having 1 to 10 carbon atoms, or −, in which one or more −CH ₂₋ may be independently substituted with −O−, −COO− or −OCO−, respectively. It is even more preferable to represent a group represented by Sp ^7- OH, and if there are a plurality of L ^4, they are the same. It may be different, and it is particularly preferable to represent a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a group represented by −Sp ⁷ −OH.

In general formula ^(I), from P 1, ^{P 2} and ^{P 3} are each independently the above formula (P-1) represents a group selected from the formulas (P-7), ^{if P 1} there are a plurality of they may be the same or different and they if P ² there are a plurality may be the same or different and they if P ³ there are a plurality optionally be the same or different Is also good. Ease of synthesis, availability of raw materials ease, liquid, storage stability, in terms of stability and voltage holding ratio of the pre-tilt angle of the case of manufacturing a display device, P ^1, P ² and P ³ is P ¹ they If there are multiple may be the same or different and may be different even if the same they If P ² there are a plurality, there they are identical if P ³ there are multiple It is preferable that each group independently represents a group selected from the formula (P-1) to the formula (P-4), and P ¹ , P ² and P ³ are cases where a plurality of P ¹ are present. they may be the same or different and they if P ² there are a plurality may be the same or different and they if P ³ there are a plurality optionally be the same or different It is also preferable that each of them independently represents a group selected from the formula (P-1) to the formula (P-3), and P ¹ , P ² and P ³ are the same when a plurality of P ¹ are present. may be different even if the P ² there are a plurality thereof may be the same or different and they if P ³ there are a plurality may be the same or different and It is particularly preferable to independently represent a group selected from the formula (P-1) and the formula (P-2).

In the general formula ^{(I), Sp 1, Sp} 2, Sp 3, Sp 4, Sp 6 and Sp ⁷ each represents each independently a spacer group or a single bond, they if Sp ¹ there are a plurality had the same If there are a plurality of Sp ^2, they may be the same or different, and if there are a plurality of Sp ^3, they may be the same or different, and Sp ⁷ If there are a plurality of them, they may be the same or different. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystal properties, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, Sp ¹ , Sp ² , Sp ³ , Sp ⁴ , Sp ⁴ , sp ⁶ and sp ⁷ may be different even if the same those if sp ¹ there are a plurality, they if sp ² there are a plurality may be different even in the same, sp ³ multiple when present they may be the same or different and may be those if Sp ⁷ there are a plurality have the same or different and are any of a hydrogen atom in the group is substituted by fluorine atoms may be, one or more -CH ₂ - are each independently -O -, - S -, - CO -, - COO -, - OCO -, - CO-S -, - S-CO -, - Directs with 1 to 20 carbon atoms that may be replaced by O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-, -CF = CF- or -C≡C- It preferably represents a chain or branched alkylene group or a single bond, and Sp ¹ , Sp ² , Sp ³ , Sp ⁴ , Sp ⁶ and Sp ⁷ are different even if they are the same when there are a plurality of Sp ^1. If there are a plurality of Sp ^2, they may be the same or different, and if there are a plurality of Sp ^3, they may be the same or different, and there are a plurality of Sp ^7. If they may be the same or different, one or more −CH ₂ −s are independently replaced by −O−, −COO−, −OCO−, −O−CO−O−. It is more preferable to represent a linear or branched alkylene group or a single bond having 1 to 10 carbon atoms, and Sp ¹ , Sp ² , Sp ³ , Sp ⁴ , Sp ⁶ and Sp ⁷ have a plurality of Sp ^1. If they are, they may be the same or different, if there are multiple Sp ^2, they may be the same or different, and if there are multiple Sp ^3, they may be the same or different. even if well, if the Sp ⁷ there are a plurality thereof may be the same or different and one or more -CH ₂ - are each independently -O -, - COO -, - OCO- in It is more preferable to represent a linear or branched alkylene group or a single bond having 1 to 10 carbon atoms which may be replaced, and Sp ¹ , Sp ² , Sp ³ , Sp ⁴ , Sp ⁶ and Sp ⁷ are Sp ^1. If there are multiple, they are the same They may be present or different, and if there are a plurality of Sp ^2, they may be the same or different, and if there are a plurality of Sp ^3, they may be the same or different, Sp. ^{When a} plurality of ^7's are present, they may be the same or different, and one or more −CH ₂₋ may be replaced with −O− a linear alkylene group having 1 to 8 carbon atoms or It is even more preferable to represent a single bond, and Sp ¹ , Sp ² , Sp ³ , Sp ⁴ , Sp ^6, and Sp ⁷ may be the same or different if there are multiple Sp ¹ , and Sp ² When there are a plurality of Sp ⁷ , they may be the same or different, when there are a plurality of Sp ^3, they may be the same or different, and when there are a plurality of Sp ^7, they are the same. It may be different, and it is particularly preferable to represent a linear alkylene group or a single bond having 1 to 5 carbon atoms in which one or more −CH ₂₋ may be replaced with −O−.

In general formula (I), Sp ⁵ represents a tetravalent group. Sp ⁵ may represent a carbon atom or a silicon atom from the viewpoints of ease of synthesis, availability of raw materials, liquid crystallinity, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate. Preferably, Sp ⁵ particularly preferably represents a carbon atom.

In the general formula (I), m1 represents 0, 1, 2 or 3. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystallinity, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, m1 preferably represents 0, 1 or 2. , M1 more preferably represents 1 or 2, and m1 particularly preferably represents 2.

In general formula (I), k1 and k2 each independently represent an integer from 0 to 4, r1 and r2 each independently represent an integer from 0 to 4, but k1 + r1 represent an integer from 0 to 4. k2 + r2 represents an integer from 0 to 4. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystallinity, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, k1 represents 0, 1, 2 or 3. r1 preferably represents 0, 1, 2 or 3, k1 more preferably represents 0, 1 or 2, r1 more preferably represents 0, 1 or 2, k1 represents 0 or 1, r1 represents 0. Or 1, it is more preferable that k1 represents 0, and r1 particularly preferably represents 0 or 1. Further, k2 preferably represents 0, 1, 2 or 3, r2 preferably represents 0, 1, 2 or 3, k2 represents 0, 1 or 2, and r2 represents 0, 1 or 2. More preferably, k2 represents 1 or 2, r2 more preferably 0 or 1, k2 represents 1 or 2, and r2 particularly preferably represents 0.

In the general formula (I), k3 represents 0, 1 or 2, r3 represents 0, 1 or 2, but k3 + r3 represents 2. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystallinity, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, k3 represents 0 or 1, and r3 represents 1 or It is preferable that 2 represents, k3 represents 0, and r3 represents 2.

The compound represented by the general formula (I) is easy to synthesize, easy to obtain raw materials, liquid crystal property, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate. The following general formula (Ii)

(In the ^{formula, R a1} is of the following formula (Ra1)

(In the formula, the broken line represents the bond position.)
In R ^11, a hydrogen atom, a fluorine atom, a chlorine atom, or any hydrogen atom in the group may be replaced with a fluorine atom, and one or more −CH ₂₋ are independently −O− and −CO−. , -COO-, -OCO-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = Represents a linear or branched alkyl group having 1 to 18 carbon atoms which may be substituted by CH-, -CH = CH-, -CF = CF- or -C≡C-.
A ¹¹ is from the following formula (A1-1) to formula (A1-11).

(Wherein the dashed line represents a bond position, they if L ¹¹ there are a plurality may be the same or different.) Represents a group selected from the same case those A ¹¹ there are multiple Can be different
A ²¹ and A ³¹ each independently represent a group selected from the above formulas (A1-1), formula (A1-2), formula (A1-8) and formula (A1-9).
Z ¹¹ and Z ²¹ are independently -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -COO-, -OCO-, -CF ₂ O-, -OCF _2- , -COO- _{CH 2 CH 2 -, - OCO} -CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO- or represents a single ^bond, the same those ^{if Z 11} there are a plurality of It can be different or different
L ¹¹ , L ²¹ and L ³¹ may each independently have a fluorine atom, a chlorine atom, or any hydrogen atom in the group substituted with a fluorine atom, and one or more −CH ₂ − are independent of each other. Then -O-, -CO-, -COO-, -OCO-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH Linear or branched alkyl with 1 to 20 carbon atoms which may be substituted by = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- represents a group, they if L ¹¹ there are a plurality may be the same or different and they if L ²¹ there are a plurality may be the same or different and L ³¹ is plurality of If they do, they may be the same or different,
In L ^41, a hydrogen atom, a fluorine atom, a chlorine atom, or any hydrogen atom in the group may be substituted with a fluorine atom, and one or more −CH ₂₋ are independently −O−, −. CO-, -COO-, -OCO-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO- CH = CH -, - CH = CH -, - CF = CF- or a linear or branched alkyl group from a good 1 -C be substituted for 20 by -C≡C- or ^{-Sp 71,} - It represents a group represented by OH, but when there are a plurality of L ^41s, they may be the same or different.
P ¹¹ , P ²¹ and P ³¹ each independently represent a group selected from the formula (P-1) to the formula (P-4), but when there are a plurality of P ¹¹ , they are different even if they are the same. at best, if the P ²¹ there are a plurality thereof may be the same or different and they if P ³¹ there are a plurality may be the same or different and
Sp ¹¹ , Sp ²¹ , Sp ³¹ , Sp ⁴¹ , Sp ⁶¹ and Sp ⁷¹ have one or more -CH _2- independently -O-, -COO-, -OCO-, -O-CO-O-, respectively. represents a linear or branched alkylene group or a single bond may one to ten carbon atoms be replaced with, they if Sp ¹¹ there are a plurality may be different even in the same, Sp ²¹ If there are a plurality of Sp ⁷¹ , they may be the same or different, if there are a plurality of Sp ^31, they may be the same or different, and if there are a plurality of Sp ^71, they may be the same. Can be different
m11 represents 0, 1 or 2,
k11 represents 0, 1, 2 or 3, r11 represents 0, 1, 2 or 3, while k11 + r11 represents an integer from 0 to 4.
k21 represents 0, 1, 2 or 3, r21 represents 0, 1, 2 or 3, while k21 + r21 represents an integer from 0 to 4.
k31 represents 0 or 1, r31 represents 1 or 2, while k31 + r31 represents 2.
k11 + k21 + k31 represent an integer from 1 to 6. ) Is preferable, and the following general formula (I-ii)

(In the ^{formula, R a2} is of the following formula (Ra2)

(In the formula, the broken line represents the bond position.)
R ¹² comprises a linear or branched alkyl group having 1 to 8 carbon atoms in which one or more −CH ₂₋ may be independently substituted with −O−, −COO− or −OCO−. Represent,
A ¹² formula from the following formula (A2-1) (A2-4)

(In the equation, the broken line represents the bonding position, and if there are a plurality of L ^12s, they may be the same or different.) However, if there are a plurality of A ^12s, they are the same. Can be different,
A ²² and A ³² independently represent groups selected from the above formulas (A2-1) and (A2-2), respectively.
Z ¹² and Z ²² independently represent -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CF ₂ O-, -OCF _2- or single bond, but there are multiple Z ^12s. If they do, they may be the same or different,
L ¹² , L ²² and L ³² independently represent a fluorine atom, a linear alkyl group having 1 to 8 carbon atoms or a linear alkoxy group having 1 to 7 carbon atoms, but there are a plurality of L ^12s. If they are, they may be the same or different, if there are multiple L ^22s, they may be the same or different, and if there are multiple L ^32s, they may be the same or different. May be
L ⁴² may be a hydrogen atom or a linear or linear carbon atom having 1 to 10 carbon atoms in which one or more −CH ₂₋ may be independently substituted with −O−, −COO− or −OCO−, respectively. It represents a branched alkyl group or a group represented by -Sp ^72- OH, but when a plurality of L ^42s are present, they may be the same or different.
P ¹² , P ²² and P ³² each independently represent a group selected from the formulas (P-1) to (P-3), but when there are a plurality of P ^12, they are the same but different. If there are a plurality of P ^22s, they may be the same or different.
Sp ¹² , Sp ²² , Sp ³² , Sp ⁴² , Sp ⁶² and Sp ⁷² may be a linear alkylene group having 1 to 8 carbon atoms or a single bond in which one or more -CH _2- may be replaced with -O-. It represents a bond, but when there are a plurality of Sp ^12s, they may be the same or different, and when there are a plurality of Sp ^22s, they may be the same or different, and there are a plurality of Sp ^72s. If they do, they may be the same or different,
m12 represents 1 or 2
k12 represents 0, 1 or 2, r12 represents 0, 1 or 2, while k12 + r12 represents an integer from 0 to 4.
k22 represents 0, 1 or 2, r22 represents 0, 1 or 2, while k22 + r22 represents an integer from 0 to 4.
k32 represents 0 or 1, r32 represents 1 or 2, while k32 + r32 represents 2.
k12 + k22 + k32 represent an integer from 1 to 6. ) Is more preferable, and the following general formula (I-iii)

^{(Wherein, R a3} is the following formula (Ra3)

(In the formula, the broken line represents the bond position.)
R ¹³ represents a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms.
A ¹³¹ and A ¹³² are independently represented by the following equations (A3-1) and (A3-2), respectively.

(In the formula, the broken line represents the bond position.) Represents the group selected from
L ²³ represents a fluorine atom, a methyl group, an ethyl group, a propyl group, a methoxy group or an ethoxy group.
L ⁴³¹ and L ⁴³² independently represent a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a group represented by -Sp ^73- OH.
P ²³ each represents a group selected from the formula (P-1) and formula (P-2), those cases where P ²³ there are a plurality may be the same or different and
Sp ²³ , Sp ⁴³ , Sp ⁶³ and Sp ⁷³ represent a linear alkylene group or single bond having 1 to 5 carbon atoms in which one or more -CH ₂ -may be replaced with -O-, while Sp ^When there are a plurality of ^23, they may be the same or different, and when there are a plurality of Sp ^73, they may be the same or different.
r13 represents 0 or 1 and represents
k23 represents 1 or 2. ) Is more preferable.

Specifically, as the compound represented by the general formula (I), the following formulas (I-1) to (I-25)

Examples thereof include compounds represented by.

The amount of the compound (A) contained in the liquid crystal composition is preferably about 0.2 to 4% by mass, more preferably about 0.4 to 3% by mass, and 0.5 to 2% by mass. It is more preferably about%, and particularly preferably about 0.5 to 1% by mass. The liquid crystal composition containing the alignment aid in such an amount has a small change in the pretilt angle before and after light irradiation in the manufacturing process of the display element. In addition, the voltage retention rate after light irradiation in the manufacturing process of the display element is excellent.

<Compound (B)>
The compound (B) has a group selected from a hydroxyl group, an amino group, a mercapto group and a carboxyl group. These groups in the compound (A) are a member (electrode (for example, ITO), a substrate (for example, a glass substrate, an acrylic substrate, a transparent substrate), which is in direct contact with the liquid crystal layer containing the liquid crystal composition in the display element. (Flexible substrate, etc.), resin layer (for example, color filter, alignment film, overcoat layer, etc.), insulating film (for example, inorganic material film, SiNx, etc.)), and as a result, the above compound (B) Can be attracted to or bonded to a member that comes into direct contact with the liquid crystal layer containing the liquid crystal composition. Further, the compound (B) has a dioxane structure, and interacts with a metal or a metal ion eluted in a small amount from a member that directly contacts the liquid crystal layer containing the liquid crystal composition in the display element. Can be coordinated. As a result of the above interaction, the compound (B) can capture the metal or metal ion on the member that is in direct contact with the liquid crystal layer containing the liquid crystal composition, and can prevent elution into the liquid crystal composition. Here, the metal or the metal ion catalyzes and accelerates the transesterification reaction that occurs between the hydroxyl group and the ester structure in the structure of the compound (A), so that the compound (B) is a metal or a metal ion. By capturing the compound (A), the transesterification reaction in the structure of the compound (A) is prevented, and thus the amount of change in the pretilt angle of the display element before and after light irradiation is reduced and the voltage retention rate after light irradiation is prevented from decreasing. effective.

Further, it is preferable that the compound (B) is a compound having a dioxane structure and a hindered phenol structure. When the compound (B) has such a structure, the hindered phenol structure interacts with the above-mentioned member in the display element and also acts as an antioxidant, thereby further increasing the voltage retention after light irradiation. Can be enhanced.

The compound (B) has the following general formula (II).

(In the formula, R ² is hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethyl. Amino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one or more -CH _2- each independently -O-, -S-, -CO-, -COO- , -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH- OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- may be substituted with 1 to 20 carbon atoms. Representing a linear or branched alkyl group, any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or R ² is the following formula (R2T).

(In the formula, the broken line represents the bond position.)
R ^b , R ^c , R ^d and ^Re each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms.
A ⁵ is the formula from the following formula (A5-1) (A5-3)

(In the formula, the broken line represents the bond position, and R ^f , R ^g , R ^h , R ⁱ , R ^j and R ^k are independently hydrogen atoms or linear or branched alkyl having 1 to 10 carbon atoms. Represents a group.) Represents a group selected from
A ⁴ and ^{A 6} are each independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine-2,5-diyl group , Pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, tetrahydro represents a-2,5-diyl group or 1,3-dioxane-2,5-diyl group may be substituted by or one or more substituents L ⁵ or these groups are unsubstituted , if a ⁴ there are a plurality thereof may be the same or different and they if a ⁶ there are a plurality may be the same or different and
L ⁵ is a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropyl. Amino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one or more -CH _2- are independently -O-, -S-, -CO-, -COO-, -OCO-, -CO. -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH Linear or branched alkyl with 1 to 20 carbon atoms which may be substituted with = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- represents a group, any hydrogen atom in the alkyl group may be substituted by fluorine atoms, they if which L ⁵ presence of a plurality may have the same or different and
Z ³ , Z ⁴ , Z ⁵ and Z ⁶ are independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, respectively. -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH -CO-NH-, -NH-O-, -O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _{2- , -CH 2 CH 2 -COO -,} - CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH = Represents CH-, -N = N-, -CH = N-, -N = CH-, -CH = N-N = CH-, -CF = CF-, -C≡C- or a single bond, but Z ³ they if there exist a plurality may be the same or different and they if Z ⁴ there are a plurality may be the same or different and
m2 and m3 independently represent 0, 1, 2 or 3, respectively. ) Is preferable.

In general formula (II), R ² is hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino. A group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one or more -CH ₂ − independently of -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH The number of carbon atoms which may be substituted by = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- 1 Represents a linear or branched alkyl group from 20 to 20, any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or R ² is a group represented by the formula (R2T). Represent. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystal properties, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, R ² is a hydrogen atom, a fluorine atom, a chlorine atom, A pentafluorosulfanyl group, a nitro group, a cyano group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or any hydrogen atom in the group may be substituted with a fluorine atom, and one or more atoms may be substituted. -CH _2- independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-,- CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-,- preferably representing the CF = CF- or -C≡C- group represented by linear or branched alkyl group or the formula 20 from a good 1 -C be substituted (R2T) by, R ² Can be a hydrogen atom, a fluorine atom, a chlorine atom, or any hydrogen atom in the group may be replaced with a fluorine atom, and one or more −CH ₂₋ are independently −O−, −CO−, −. COO-, -OCO-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH- , -CH = CH-, -CF = CF- or -C≡C- may be substituted with a linear or branched alkyl group having 1 to 18 carbon atoms or a group represented by the formula (R2T). In R ² , any hydrogen atom in the group may be replaced with a fluorine atom, and one or more −CH ₂₋ are independently −O−, −CO−, −. more preferably represents a group represented by COO- or -OCO- linear or branched alkyl radical or formula from a good 1 -C be replaced 18 by (R2T), R ² is one The above −CH ₂₋ may be independently substituted with −O−, −COO− or −OCO−, respectively, with a linear or branched alkyl group having 1 to 8 carbon atoms or formula (R2T). even more preferably represent a group represented by, R ² is a group represented by the straight-chain alkoxy group or formula 4 from a linear alkyl group or a carbon atom number of 1 to 5 carbon atoms (R2T) Is particularly preferable.

In the general formula (II), R ^b , R ^c , R ^d and ^Re each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystal properties, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, R ^b , R ^c , R ^d and ^Re are It is preferable that each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms, and R ^b , R ^c , R ^d and ^Re each independently represent a linear or branched alkyl group having 1 to 6 carbon atoms. It is more preferable to represent a linear or branched alkyl group, and it is further preferable that R ^b , R ^c , R ^d and ^Re each independently represent a linear or branched alkyl group having 2 to 5 carbon atoms. , R ^b , R ^c , R ^d and ^Re each independently represent a branched alkyl group having 3 to 5 carbon atoms, and R ^b , R ^c , R ^d and ^Re are tert-. It is particularly preferred to represent a butyl group.

In the general formula (II), A ⁵ represents a group selected from the formula (A5-1) to the formula (A5-3), and R ^f , R ^g , R ^h , R ⁱ , R ^j and R ^f , R ^g , R ^h , R ⁱ , and R ^j in these groups. R ^k independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystal properties, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, R ^f , R ^g , R ^h , ^Ri , R ^j and R ^k preferably each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms, and R ^f , R ^g , R ^h , R ⁱ , R ^j and R, respectively. It is more preferable that ^k independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, and R ^f , R ^g , R ^h , R ⁱ , R ^j and R ^k are respectively. It is more preferable to independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms, and R ^f , R ^g , R ^h , R ⁱ , R ^j and R ^k are independent of each other. It is even more preferable to represent a hydrogen atom or a linear alkyl group having 1 to 3 carbon atoms, and R ^f , R ^g , R ^h , ^Ri , R ^j and R ^k each independently represent a hydrogen atom. Is particularly preferable. Further, it is particularly preferable that A ⁵ represents a group selected from the formula (A5-1) and the formula (A5-3).

In formula (II), ^{A 4} and ^{A 6} are each independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine -2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2 , 6-diyl group, represent a tetrahydropyran-2,5-diyl group or 1,3-dioxane-2,5-diyl group, or these groups are unsubstituted or one or more substituents ^{L 5} may be substituted by, if a ⁴ there are a plurality thereof may be different even in the same, a ⁶ may be those when there are multiple different be the same. Ease of synthesis, availability of raw materials ease, liquid, storage stability, in terms of stability and voltage holding ratio of the pre-tilt angle of the case of manufacturing a display device, they if A ⁴ and A ⁶ there are a plurality of It may be the same or different and each independently may be substituted by or is one or more substituents L ⁵ an unsubstituted 1,4-phenylene group, 1,4-cyclohexylene group , naphthalene-2,6-diyl group, tetrahydropyran-2,5-diyl group, preferably represents a 1,3-dioxane-2,5-diyl group, they ^{if a 4} and ^{a 6} there are a plurality of It may be the same or different, and each of them independently has the following equations (A-12) to (A-22).

(Wherein the dashed line represents a bonding position, L ⁵ may be those when there are multiple different be the same.) It is more preferable to represent a group selected from, A ⁴ and A ⁶ are more when present they may be the same or different and more preferably each from independently formula (a-12) represents a group selected from the formula (a-18), a ⁴ and a ⁶ are they If there are multiple may be the same or different and is even more preferably represent a group selected from each independently formula (a-12) from the equation (a-15), a ⁴ and a ^When a plurality of 6s are present, they may be the same or different, and it is particularly preferable that 6 represents a group independently selected from the formulas (A-12) and (A-13).

In formula (II), L ⁵ is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, pentafluorosulfanyl group, a nitro group, a cyano group, isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, dimethyl Amino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one or more -CH _2- each independently -O-, -S-, -CO-, -COO- , -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH- OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- may be substituted with 1 to 20 carbon atoms. represents a linear or branched alkyl group, any hydrogen atom in the alkyl group may be substituted by fluorine atoms, even those cases where which L ⁵ presence of a plurality optionally be the same or different good. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystal properties, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, L ⁵ is a fluorine atom, a chlorine atom, and a pentafluorosulfanyl. A group, a nitro group, a cyano group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or any hydrogen atom in the group may be substituted with a fluorine atom, and one or more -CH ₂ -Independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH -, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF - or preferably represents a linear or branched alkyl group having from good 1 -C be replaced 20 by -C≡C-, L ⁵ is a fluorine atom, a chlorine atom, or any of groups The hydrogen atom may be replaced with a fluorine atom, and one or more -CH ₂ −s are independently −O−, −CO−, −COO−, −OCO−, −CO-NH−, −. NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or- more preferably represents a linear or branched alkyl group having from good 1 -C be replaced 20 by C≡C-, L ⁵ is fluorine atom, or, any hydrogen atom in the group fluorine It may be substituted with an atom, and one or more -CH _2- may be independently substituted with -O-, -CO-, -COO- or -OCO-, and the number of carbon atoms is 1 to 12. It is more preferable to represent a linear or branched alkyl group of, and L ⁵ represents a fluorine atom, a linear alkyl group having 1 to 8 carbon atoms, or a linear alkoxy group having 1 to 7 carbon atoms. Is even more preferable, and it is particularly preferable that L ⁵ represents a fluorine atom, a methyl group, an ethyl group, a propyl group, a methoxy group or an ethoxy group.

In the general formula (II), Z ³ , Z ⁴ , Z ⁵ and Z ⁶ are independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH ₂ -,-, respectively. CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-,- NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH ₂ -,- OCO-CH ₂ CH _2- , -CH ₂ CH _2- COO-, -CH ₂ CH _2- OCO-, -COO-CH _2- , -OCO-CH _2- , -CH _2- COO-, -CH ₂ -OCO-, -CH = CH-, -N = N-, -CH = N-, -N = CH-, -CH = N-N = CH-, -CF = CF-, -C≡C- or It represents a single bond, they if Z ³ there are a plurality may be different even in the same, Z ⁴ is they may be the same or different when there are multiple. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystal properties, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, Z ³ , Z ⁴ , Z ⁵ and Z ⁶ are -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -COO-, -OCO-, -CO-NH-, -NH-CO-, -CF ₂ O-, -OCF, respectively. _2- , -CH = CH-COO-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _2- , -CH ₂ CH _2- COO-, -CH ₂ CH _{2 -OCO -, - CH = CH} -, - CF = CF -, - C≡C- or preferably a single ^{bond, Z 3, Z 4, Z} 5 and ^{Z 6} are -OCH ₂ each independently -, -CH ₂ O-, -CH ₂ CH _2- , -COO-, -OCO-, -CF ₂ O-, -OCF _2- , -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _{2 -, - CH 2 CH 2 -COO} -, - CH 2 CH 2 -OCO- or more preferably a single ^{bond, Z 3, Z 4, Z} 5 and ^{Z 6} are each independently -OCH ₂ -, _{-CH 2 O -, - CH 2} CH 2 -, - COO -, - OCO -, - CF 2 O -, - OCF 2 - or more preferably a single ^{bond, Z 3, Z 4, Z} 5 and It is even more preferred that Z ⁶ independently represents −OCH ₂ −, −CH ₂ O−, −CH ₂ CH ₂₋ , −CF ₂ O−, −OCF _2- or single bond, respectively, Z ³ and Z. It is particularly preferred that ⁴ , Z ⁵ and Z ⁶ represent a single bond.

In the general formula (II), m2 and m3 independently represent 0, 1, 2 or 3, respectively. From the viewpoints of ease of synthesis, availability of raw materials, liquid crystallinity, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate, m2 and m3 are independently 0, 1, or 0, respectively. It is preferable that 2 is represented, m2 and m3 are more preferably 0 or 1 respectively, and m2 and m3 are particularly preferably 0.

The compound represented by the general formula (II) is easy to synthesize, easy to obtain raw materials, liquid crystal property, storage stability, stability of pretilt angle when a display element is manufactured, and voltage retention rate. The following general formula (II-i)

(Wherein, R ²¹ represents a hydrogen atom, a fluorine atom, a chlorine atom, any hydrogen atom in the group may be substituted by a fluorine atom, one or more -CH 2 _- are each independently -O- , -CO-, -COO-, -OCO-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-,- A linear or branched alkyl group having 1 to 18 carbon atoms which may be substituted by OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- or the following formula. (R2T1)

(In the formula, the broken line represents the bond position.)
R ^b1 , R ^c1 , R ^d1 and R ^e1 each independently represent a linear or branched alkyl group having 2 to 5 carbon atoms.
A ⁵¹ is a formula (A51-3) from the following formula (A51-1).

(In the formula, the broken line represents the bond position, and R ^f1 , R ^g1 , R ^h1 , R ⁱ¹ , R ^j1 and R ^k1 are independently hydrogen atoms or linear or branched alkyl having 1 to 6 carbon atoms, respectively. Represents a group.) Represents a group selected from
A ⁴¹ and A ⁶¹ are independently expressed by the following equations (A1-12) to (A1-22).

(In the equation, the broken line represents the bonding position, and when there are a plurality of L ^51s, they may be the same or different.)
In L ^51, a fluorine atom, a chlorine atom, or an arbitrary hydrogen atom in the group may be replaced with a fluorine atom, and one or more -CH ₂ − are independently -O-, -CO-, respectively. -COO-, -OCO-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH -, - CH = CH -, - CF = CF- or -C≡C- represents a linear or branched alkyl group having 20 good 1 -C be substituted ^{by, L 51} is plurality of If they do, they may be the same or different,
Z ³¹ , Z ⁴¹ , Z ⁵¹ and Z ⁶¹ are independently -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -COO-, -OCO-, -CF ₂ O-, -OCF, respectively. _{2 -, - COO-CH 2} CH 2 -, - OCO-CH 2 CH 2 -, - CH 2 CH 2 -COO -, - CH 2 CH 2 -OCO- or a single bond,
m21 and m31 independently represent 0 or 1, respectively. ) Is preferable, and the following general formula (II-ii)

(In the formula, R ²² is a linear or branched carbon atom number 1 to 8 in which one or more −CH ₂₋ may be independently substituted with −O−, −COO− or −OCO−. Alkyl group or the following formula (R2T2)

(In the formula, the broken line represents the bond position.)
R ^b2 , R ^c2 , R ^d2 and R ^e2 each independently represent a branched alkyl group having 3 to 5 carbon atoms.
A ⁵² is from the following formula (A52-1) to formula (A52-3).

(In the formula, the broken line represents the bond position, and R ^f2 , R ^g2 , R ^h2 , R ⁱ² , R ^j2 and R ^k2 are independently hydrogen atoms or linear or branched alkyl having 1 to 3 carbon atoms. Represents a group.) Represents a group selected from
A ⁴² is from the following formula (A2-12) to formula (A2-15).

(In the formula, the broken line represents the bond position.) Represents the group selected from
L ⁵² represents a fluorine atom, a linear alkyl group having 1 to 8 carbon atoms, or a linear alkoxy group having 1 to 7 carbon atoms.
Z ³² , Z ⁵² and Z ⁶² independently represent -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CF ₂ O-, -OCF _2- or single bond, respectively.
m22 represents 0 or 1. ) Is more preferable, and the following general formula (II-iii)

(In the formula, R ²³ is a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms, or the following formula (R2T3).

(In the formula, the broken line represents the bond position.)
A ⁵³ is the following equation (A53-1) and equation (A53-3).

(In the formula, the broken line represents the bond position, and R ^f3 represents a hydrogen atom, a methyl group, an ethyl group, or a propyl group.)
Z ³³ represents −CH ₂ CH _2- or single bond
m23 represents 0 or 1. ) Is more preferable.

Specifically, the compound represented by the general formula (II) is represented by the following formulas (II-1) to (II-25).

Examples thereof include compounds represented by.

The amount of the compound (B) contained in the liquid crystal composition is preferably about 0.01 to 2% by mass, more preferably about 0.01 to 1% by mass, and 0.02 to 0. It is more preferably about 5% by mass, and particularly preferably about 0.02 to 0.1% by mass. The liquid crystal composition containing the alignment aid in such an amount has a small change in the pretilt angle before and after light irradiation in the manufacturing process of the display element. In addition, the voltage retention rate after light irradiation in the manufacturing process of the display element is excellent.

In the present invention, the ring structure contained in the 1,4-cyclohexylene group, the decahydronaphthalene-2,6-diyl group, the tetrahydropyran-2,5-diyl group and the 1,3-dioxane-2,5-diyl group. Can be either a trans form or a cis form, respectively, or may be a mixture of a trans form and a cis form. From the viewpoint of liquid crystallinity, the content of each trans body is preferably higher than that of the cis body, and the content of the trans body in the ring structure is more preferably 95% or more, and the content of the trans body in the ring structure is more preferable. The content is more preferably 98% or more, the content of the trans in the ring structure is even more preferably 99% or more, and the content of the trans in the ring structure is 99.9% or more. Is particularly preferable. Further, in the present invention, the following notation (CY-1)

(In the formula, * represents a bond) means a trans form and / or a cis form of a 1,4-cyclohexylene group, and the following notation (CY-1-t) and notation (CY-1-c). )

(In the formula, * represents a bond) means a trans form and a cis form of 1,4-cyclohexylene groups, respectively. The following notation (DX-1) and notation (DX-2)

(In the formula, * represents a bond) means a trans form and / or a cis form of a 1,3-dioxane-2,5-diyl group, and the following notation (DX-1-t) and notation ( DX-2-t)

(In the formula, * represents a bond) means a trans form of 1,3-dioxane-2,5-diyl group, respectively, and the following notation (DX-1-c) and notation (DX-2-). c)

(In the formula, * represents a bond) means a cis form of a 1,3-dioxane-2,5-diyl group, respectively. However, in the specific example of the compound using these, it means that a trace amount of cis-form and trans-form may be contained in addition to the trans-form and cis-form, respectively. Specifically, for example, the content of the cis form contained in the trans form is preferably 10% or less, more preferably 5% or less, further preferably 2% or less, and 1% or less. It is even more preferably present, and particularly preferably 0.1% or less.

Further, in the present invention, each element may be replaced with an isotope of the same element.

The liquid crystal composition of the present invention has the following general formula (III).

(In the formula, R ³ and R ⁴ are independently alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 7 carbon atoms, alkenyl groups having 2 to 8 carbon atoms, or carbon atoms 2 to 7 respectively. Represents the alkenyloxy group of
B ¹ and B ² are independently expressed from the following equations (B-1) to (B-10).

(Wherein the dashed line represents. A binding position) represents a group selected from, if the B ² there is a plurality thereof may be the same or different and
m4 represents an integer from 1 to 4. ) Is preferably contained. Liquid crystal phase temperature range of liquid crystal composition, refractive index anisotropy, dielectric constant anisotropy, rotational viscosity and elastic modulus, mixed with a compound represented by the general formula (I) and a compound represented by the general formula (II). From the viewpoint of reliability in the case of the above, the compound represented by the general formula (III) is the following general formula (III-i).

(In the formula, R ³¹ and R ⁴² are independently alkyl groups having 1 to 5 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkenyl groups having 2 to 5 carbon atoms, or 2 to 4 carbon atoms. Represents the alkenyloxy group of
B ¹¹ and B ⁴¹ are independently expressed by the following equations (B1-1) to (B1-4).

(In the formula, the broken line represents the bonding position.) However, when there are a plurality of B ^41s, they may be the same or different.
m41 represents 1 or 2. ) Is more preferable, and the compound represented by the general formula (III) is the following general formula (III-ii).

(In the formula, R ³² and R ⁴² independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.
B ¹² and B ²² are independently represented by the following equations (B2-1) and (B2-2), respectively.

(In the formula, the broken line represents the bonding position.) However, when there are a plurality of B ^22s, they may be the same or different.
m42 represents 1 or 2. ) Is more preferable, and the compound represented by the general formula (III) is from the following general formula (III-iii-1) to the general formula (III-iii-11).

(In the formula, R ³³ and R ⁴³ independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms). It is particularly preferable that the compound is a compound.

When the liquid crystal composition contains a compound represented by the general formula (III), it may contain one compound represented by the general formula (III), and a plurality of compounds represented by the general formula (III). May be contained. When the liquid crystal composition of the present invention contains a compound represented by the general formula (III), the total content of the compounds represented by the general formula (III) in the liquid crystal composition is 5% by mass or more, 95 It is preferably 8% by mass or more, more preferably 55% by mass or less, further preferably 10% by mass or more and 50% by mass or less, and 15% by mass or more and 45% by mass or less. Even more preferably, it is 20% by mass or more, and particularly preferably 40% by mass or less. Here, "the total content of the compounds represented by the general formula (III)" is expressed in the general formula (III) when the liquid crystal composition contains one compound represented by the general formula (III). It means the content of the compound represented, and when the liquid crystal composition contains a plurality of compounds represented by the general formula (III), the total content of the plurality of compounds represented by the general formula (III) is summed up. means.

When the dielectric anisotropy (Δε) of the liquid crystal composition is negative, the dielectric anisotropy (Δε) is preferably −5.0 or more and −1.0 or less. From the viewpoint of the liquid crystal phase temperature range, driving voltage, rotational viscosity and elastic modulus of the liquid crystal composition, the dielectric anisotropy (Δε) is preferably -4.9 or more, preferably -1.5 or less, and -4. It is more preferably 8.8 or more and -2.0 or less, further preferably -4.7 or more and -2.5 or less, and -4.6 or more and -2.7 or less. It is even more preferable, and it is particularly preferable that it is −4.5 or more and −3.0 or less.

When the dielectric anisotropy (Δε) of the liquid crystal composition is negative, the liquid crystal composition has the following general formula (IV).

(In the formula, R ⁵ and R ⁶ are independently alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 7 carbon atoms, alkenyl groups having 2 to 8 carbon atoms, or carbon atoms 2 to 7 respectively. Represents the alkenyloxy group of
B ³ and B ⁴ are independently expressed by the following equations (B-11) to (B-19).

(Wherein the dashed line represents. A binding position) represents a group selected from, if B ³ there are a plurality of them may be the same or different and the same case those B ⁴ there are a plurality of Can be different
Z ⁷ and Z ⁸ are independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, -OCO-, -CO. -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH- COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _2- , -CH ₂ CH ₂ -COO-, -CH ₂ CH _2- OCO-, -COO-CH _2- , -OCO-CH _2- , -CH _2- COO-, -CH ₂ -OCO-, -CH = CH-, -N = N -, - CH = N - , - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, ^{if Z 7} there are a plurality of they may be the same or different and they if Z ⁸ there are a plurality may be the same or different and
m5 and m6 independently represent integers from 0 to 3, while m5 + m6 represent integers from 1 to 3. ) Is preferably contained. From the viewpoint of the liquid crystal phase temperature range, refractive index anisotropy, dielectric anisotropy, rotational viscosity and elastic modulus of the liquid crystal composition, the compound represented by the general formula (IV) is represented by the following general formula (IV-i).

(In the formula, R ⁵¹ and R ⁶¹ are independently alkyl groups having 1 to 5 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkenyl groups having 2 to 5 carbon atoms, or 2 to 4 carbon atoms. Represents the alkenyloxy group of
B ³¹ and B ⁴¹ are independently expressed by the following equations (B1-11) to (B1-16).

(Wherein the dashed line represents. A binding position) represents a group selected from, if the B ³¹ there are a plurality of them may be the same or different and the same case those B ⁴¹ there are a plurality of Can be different,
Z ⁷¹ and Z ⁸¹ independently form -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -COO-, -OCO-, -CF ₂ O-, -OCF _2- or single bond, respectively. As represented, when there are a plurality of Z ^71s, they may be the same or different, and when there are a plurality of Z ^81s, they may be the same or different.
m51 and m61 independently represent 0, 1 or 2, while m51 + m61 represent 1 or 2. ) Is more preferable, and the compound represented by the general formula (IV) is represented by the following general formula (IV-ii).

(In the formula, R ⁵² and R ⁶² each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms.
B ³² and B ⁴² are independently represented by the following equations (B2-11) and (B2-12), respectively.

(In the formula, the broken line represents the bonding position.) However, when there are a plurality of B ^32s, they may be the same or different, and when there are a plurality of B ^42s, they are the same. Can be different,
Z ⁷² and Z ⁸² independently represent -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- or a single bond, but if there are multiple Z ^72s, they are the same but different. If there are a plurality of Z ^82s, they may be the same or different.
m52 and m92 independently represent 0, 1 or 2, while m52 + m62 represent 1 or 2. ) Is more preferable, and the compound represented by the general formula (IV) is from the following general formula (IV-iii-1) to the general formula (IV-iii-8).

(In the formula, R ⁵³ and R ⁶³ independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms). It is particularly preferable that the compound is a compound.

The liquid crystal composition of the present invention has the following general formula (V) in order to promote the polymerization reaction of the self-oriented additive.

(Wherein, ^{P 4} and ^{P 5} each independently formula from the formula (P-8) below (P-17)

(In the formula, the broken line represents the bond position.) Represents the group selected from
Sp ⁷ and Sp ⁸ each independently represent a spacer group or a single bond.
B ⁵ and B ⁶ are independently derived from the following equations (B-20) to (B-28).

(In the formula, the broken line represents the bond position, L ⁵ is a halogen atom, a cyano group, a nitro group, a pentafluorosulfanyl group, an amino group which may be substituted, a silyl group which may be substituted, or an arbitrary hydrogen atom. May be replaced with a fluorine atom, and one or more -CH ₂ −s are independently −O−, −S−, −CO−, −COO−, −OCO−, −CO−S−, − S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-,- OCO-CH = CH -, - CH = CH -, - CF = CF- or -C≡C- alkyl group having 20 good 1 -C be replaced by, ^or, P L -Sp ^L - Table with groups (wherein, P ^L is a radical polymerization, a group of polymerization by cationic polymerization or anionic polymerization, Sp ^L represents. a spacer group or a single bond) represents a, they if which L ⁵ there are multiple represents a group selected from the same or different from.), if the B ⁶ there are a plurality of them may be the same or different and
Z ⁹ is -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, -OCO-, -CO-S-, -S- CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-,- O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH-COO-, -CH = CH -OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _2- , -CH ₂ CH _2- COO-, -CH ₂ CH _2- OCO-, -COO-CH _2- , -OCO-CH _2- , -CH _2- COO-, -CH _2- OCO-, -CH = CH-, -N = N-, -CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, even they are the same ^{if Z 9} there are a plurality of May be different
m7 represents an integer from 1 to 4. ) Is preferably contained. From the viewpoint of voltage retention, tilt angle stability, and compatibility with the liquid crystal composition, the compound represented by the general formula (V) is represented by the following general formula (Vi).

(In the formula, P ⁴¹ and P ⁵¹ are independently derived from the following formulas (P1-8) to formulas (P1-11).

(In the formula, the broken line represents the bond position.) Represents the group selected from
Sp ⁷¹ and Sp ⁸¹ are carbon atoms in which one or more -CH ₂ -may be independently substituted with -O-, -COO-, -OCO- or -O-CO-O-, respectively. Represents a linear or branched alkylene group or single bond of numbers 2-12.
B ⁵¹ and B ⁶¹ are independently derived from the following equations (B1-20) to (B1-26).

(In the formula, the broken line represents the bond position, L ⁵¹ may be replaced with a fluorine atom, and any hydrogen atom may be replaced with a fluorine atom, and one or more −CH ₂ −s are independently substituted with −O−. It represents an alkyl group having 1 to 5 carbon atoms which may be used, and when a plurality of L ^51s are present, they may be the same or different), but there are a plurality of B ^61s. If they do, they may be the same or different,
Z ⁹¹ represents -CH = CH-COO-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or a single bond, but if there are multiple Z ^91s, they are the same. May be different,
m71 represents 1 or 2. ) Is more preferably contained, and the compound represented by the general formula (V) is described in the following general formulas (V-ii-1) to (V-ii-3).

(In the formula, P ⁴² and P ⁵² are independently the following formulas (P2-8) and (P2-9), respectively.

(In the formula, the broken line represents the bond position.) Represents the group selected from
Sp ⁷² and Sp ⁸² each independently represent a linear alkylene group or a single bond having 2 to 5 carbon atoms.
B ⁵² , B ⁶²¹ and B ⁶²² are independently expressed by the following equations (B2-20) to (B2-26).

(In the formula, the broken line represents the bond position, L ⁵² represents a fluorine atom, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, but they are the same when a plurality of L ^52s are present. It may be different or different.) Represents a group selected from. ) Is more preferably contained, and the compound represented by the general formula (V) is from the following general formula (V-iii-1) to the general formula (V-iii-7).

(In the formula, P ⁴³ and P ⁵³ are independently the following formulas (P3-8) and (P3-9), respectively.

(In the formula, the broken line represents the bond position.), And Sp ⁷³ and Sp ⁸³ independently represent a linear alkylene group or a single bond having 2 to 5 carbon atoms. ) Is particularly preferably contained.

By adding the compound represented by the general formula (V) to the liquid crystal composition of the present invention, it is possible to promote the polymerization of the compound represented by the general formula (I) and improve the crosslink density, and tilt the display element. Stability can be increased. When the rate of polymerization is particularly important, the absorption wavelength is preferably a long wavelength, the compound represented by the general formula (V) has a terphenyl structure or a biphenyl structure at the mesogen moiety, and a polymerizable group is present at the mesogen moiety. Is preferably bonded directly or via a relatively short spacer, and is particularly preferably having a terphenyl structure and a polymerizable group directly bonded to the mesogen site. Further, when the high crosslink density is particularly emphasized, it is compared whether the compound represented by the general formula (V) has a terphenyl structure or a biphenyl structure at the mesogen moiety and a polymerizable group is directly bonded to the mesogen moiety. It is preferable that the compound is bonded via a short spacer, and it is particularly preferable that the compound represented by the general formula (V) has a biphenyl structure at the mesogen moiety and a polymerizable group is directly attached to the mesogen moiety. Further, when the balance of both is emphasized, the compound represented by the general formula (V) has a terphenyl structure at the mesogen moiety, and is bonded via a polymerizable group directly bonded to the mesogen moiety and a relatively short spacer. It is particularly preferred to have both polymerizable groups.

Specifically, as the compound represented by the general formula (V), the following formulas (V-1) to formulas (V-25)

Examples thereof include compounds represented by.

The amount of the compound (V) contained in the liquid crystal composition is preferably about 0.05 to 2% by mass, more preferably about 0.1 to 1.5% by mass, and more preferably 0.1 to 1% by mass. It is more preferably about 1% by mass, and particularly preferably about 0.2 to 0.5% by mass. The liquid crystal composition containing the alignment aid in such an amount has a small change in the pretilt angle before and after light irradiation in the manufacturing process of the display element. In addition, the voltage retention rate after light irradiation in the manufacturing process of the display element is excellent.

Hereinafter, the present invention will be further described with reference to examples, but the present invention is not limited to these examples. In addition, "%" in the compositions of the following Examples and Comparative Examples means "mass%". When handling substances that are unstable to oxygen and / or moisture in each step, it is preferable to work in an inert gas such as nitrogen gas or argon gas. The purity of each compound is UPLC (Waters ACQUITY UPLC BEH C ₁₈ , 2.1 × 100 mm, 1.7 μm, acetonitrile / water or acetonitrile / water containing 0.1% formic acid, PDA, column temperature 40 ° C.), GC (Agient 6890A). , J & W DB-1, 30m / 0.25mm / 0.25μm, carrier gas He, FID, 100 ° C (1 minute) → temperature rise 10 ° C / min → 300 ° C (12 minutes)) or ¹ H NMR (JEOL, 400 MHz).
(Examples 1 to 50, Comparative Examples 1 to 20)
The following notation is used for the description of the compound. n represents an integer of 1 or more.
(Side chain)
−N − (CH ₂ ) _n-1 −CH ₃
n-CH _3- (CH ₂ ) _n-1-
-On-O- (CH ₂ ) _n-1 -CH ₃
nO-CH _3- (CH ₂ ) _n-1- O-
−V −CH = CH ₂
V-CH ₂ = CH-
−V1 −CH = CH-CH ₃
1V-CH _3- CH = CH-
-2V- (CH ₂ ) ₂ -CH = CH ₂
V2-CH ₂ = CH- (CH ₂ ) _2-
-2V1- (CH ₂ ) ₂ -CH = CH-CH ₃
1V2-CH _3- CH = CH- (CH ₂ ) _2-
(Ring structure)

Maternal liquid crystals N1 to N10 composed of the following compounds were prepared.

A compound having an alcohol structure and an ester structure at the content shown in the table below, a compound having a dioxane structure and a group selected from a hydroxyl group, an amino group, a mercapto group and a carboxyl group, and a monomer as an optional component are added to the parent liquid crystal. , A liquid crystal composition (M-50) was prepared from the liquid crystal composition (M-1) to be evaluated. In addition, a compound having a dioxane structure and a group selected from a hydroxyl group, an amino group, a mercapto group and a carboxyl group is not added, or instead of the compound, the following formula (R-II-1) is used.

A liquid crystal composition (RM-20) was prepared from the liquid crystal composition (RM-1) to be compared by adding the compound represented by.

A 4 cm square first substrate (common electrode substrate) having no alignment film provided with a transparent electrode layer composed of transparent common electrodes and a color filter layer, and a transparent pixel electrode driven by a corresponding active element. A second substrate (pixel electrode substrate) having no alignment film and having a pixel electrode layer having the above was prepared. A sealing material is drawn on the periphery of the first substrate, each liquid crystal composition to be evaluated and each liquid crystal composition to be compared are dropped, and the sealing material is always held by laminating with the second substrate under vacuum. A liquid crystal cell having a cell gap of 3.2 μm was prepared by curing at a pressure of 110 ° C. for 1 hour. While applying a rectangular AC wave of 10 V and 100 Hz to each of the obtained liquid crystal cells, a high-pressure mercury lamp is used to irradiate UV light having an illuminance of 100 m / cm2 at 365 nm for 200 seconds to display the evaluation target. An element and a display element to be compared were manufactured.

While applying a rectangular voltage of 30 V at a frequency of 100 Hz to each of the obtained liquid crystal cells, light was continuously irradiated from the backlight for 10 hours. The amount of change in the pretilt angle before and after light irradiation (absolute value (°) of the difference in pretilt angle before and after light irradiation) and the voltage retention rate after light irradiation were measured. The pre-tilt angle was measured using a pre-tilt angle measuring system (“OPTIPRO” manufactured by Shintech Co., Ltd.). The voltage holding ratio was measured at a frequency of 60 Hz and an applied voltage of 1 V and 333 K. The results are shown in the table below.

It can be seen that the display element manufactured by using the liquid crystal composition of the present invention has a small amount of change in the pretilt angle before and after light irradiation and a high voltage holding ratio after light irradiation. From the above results, the liquid crystal composition of the present invention is useful as a material for a liquid crystal display element that does not use an alignment film layer because changes in the pretilt angle and a decrease in the voltage retention rate are unlikely to occur.

Claims (12)

Liquid crystal composition containing a compound (A) having a hydroxyl group and an ester structure in its molecular structure, and a compound (B) having a group selected from a hydroxyl group, an amino group, a mercapto group and a carboxyl group and a dioxane structure in its molecular structure. A liquid crystal composition which is a substance, wherein the compound (A) and the compound (B) have different molecular structures. The liquid crystal composition according to claim 1, wherein the ester structure of the compound (A) is derived from a group polymerized by radical polymerization, cationic polymerization or anionic polymerization. The groups polymerized by radical polymerization, cationic polymerization or anionic polymerization in the compound (A) are represented by the following formulas (P-1) to (P-7).

The liquid crystal composition according to claim 2, which is a group selected from (in the formula, the broken line represents the bonding position). The liquid crystal composition according to any one of claims 1 to 3, wherein the compound (B) is a compound having a dioxane structure and a hindered phenol structure. The compound (A) has the following general formula (I).

(Wherein, ^{R a} is the following formula (Ra)

(In the formula, the broken line represents the bond position.)
R ¹ is hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino. A group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or one or more -CH _2- are independently -O-, -S-, -CO-, -COO-, -OCO-. , -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-,- Linear or linear with 1 to 20 carbon atoms which may be substituted by COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- Although it represents a branched alkyl group, any hydrogen atom in the alkyl group may be substituted with a fluorine atom.
A ¹ , A ² and A ³ are independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine-2,5, respectively. - diyl group, pyrimidine-2,5-diyl group, represent a tetrahydropyran-2,5-diyl group or 1,3-dioxane-2,5-diyl group, the same those ^{if a 1} there are multiple It may be present or different, and A ¹ may be unsubstituted or substituted with one or more substituents L ¹ .
Z ¹ and Z ² are independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, -OCO-, -CO. -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH- COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _2- , -CH ₂ CH ₂ -COO-, -CH ₂ CH _2- OCO-, -COO-CH _2- , -OCO-CH _2- , -CH _2- COO-, -CH ₂ -OCO-, -CH = CH-, -N = N -, - CH = N - , - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, ^{if Z 1} there are a plurality of They can be the same or different,
L ¹ , L ² , L ³ and L ⁴ are independently fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group and mercapto group. , Methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyanogroup, or one or more -CH _2- independently -O-, -S-,- CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO- , -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- may be substituted carbon Although the atoms 1 represents a linear or branched alkyl group of 20, any hydrogen atom in the alkyl group may be substituted by fluorine atoms, they if L ¹ there are a plurality had the same be different even better, if L ² there are a plurality thereof may be the same or different and they if L ³ there are a plurality may be the same or different and L ⁴ When there are a plurality of them, they may be the same or different, and L ⁴ may represent a hydrogen atom or a group represented by −Sp ⁷ −OH.
P ^1, P ² and is P ³ represents a group, each selected from the formulas from independently Formula (P-1) (P- 7), those cases where P ¹ there are a plurality of independently identical or different even if well, if the P ² there are a plurality thereof may be the same or different and they if P ³ there are a plurality may be the same or different and
Sp ¹ , Sp ² , Sp ³ , Sp ⁴ , Sp ⁶ and Sp ⁷ each independently represent a spacer group or a single bond, but if there are multiple Sp ^1, they may be the same or different. , If there are a plurality of Sp ^2, they may be the same or different, if there are a plurality of Sp ^3, they may be the same or different, and if there are a plurality of Sp ⁷ , they may be different. It can be the same or different
Sp ⁵ represents a tetravalent group and represents
m1 represents 0, 1, 2 or 3
k1 and k2 independently represent integers from 0 to 4, respectively.
r1 and r2 each independently represent an integer from 0 to 4, but k1 + r1 represents an integer from 0 to 4, and k2 + r2 represents an integer from 0 to 4.
k3 represents 0, 1 or 2,
r3 represents 0, 1 or 2, while k3 + r3 represents 2, but k1 + k2 + k3 represents an integer from 1 to 6. The liquid crystal composition according to any one of claims 1 to 4, which is a compound represented by). The compound (A) has the following general formula (I-iii).

^{(Wherein, R a3} is the following formula (Ra3)

(In the formula, the broken line represents the bond position.)
R ¹³ represents a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms.
A ¹³¹ and A ¹³² are independently represented by the following equations (A3-1) and (A3-2), respectively.

(In the formula, the broken line represents the bond position.) Represents the group selected from
L ²³ represents a fluorine atom, a methyl group, an ethyl group, a propyl group, a methoxy group or an ethoxy group.
L ⁴³¹ and L ⁴³² independently represent a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms, or a group represented by -Sp ^73- OH.
P ²³ each represents a group selected from the formulas (P-1) and formula (P-2), those cases where P ²³ there are a plurality may be the same or different and
Sp ²³ , Sp ⁴³ , Sp ⁶³ and Sp ⁷³ represent a linear alkylene group or single bond having 1 to 5 carbon atoms in which one or more -CH ₂ -may be replaced with -O-, while Sp ^When there are a plurality of ^23, they may be the same or different, and when there are a plurality of Sp ^73, they may be the same or different.
r13 represents 0 or 1 and represents
k23 represents 1 or 2. The liquid crystal composition according to any one of claims 1 to 5, which is a compound represented by). The compound (B) has the following general formula (II).

(In the formula, R ² is hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethyl. Amino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one or more -CH _2- each independently -O-, -S-, -CO-, -COO- , -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH- OCO-, -COO-CH = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- may be substituted with 1 to 20 carbon atoms. Representing a linear or branched alkyl group, any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or R ² is the following formula (R2T).

(In the formula, the broken line represents the bond position.)
R ^b , R ^c , R ^d and ^Re each independently represent a linear or branched alkyl group having 1 to 10 carbon atoms.
A ⁵ is the formula from the following formula (A5-1) (A5-3)

(In the formula, the broken line represents the bond position, and R ^f , R ^g , R ^h , R ⁱ , R ^j and R ^k are independently hydrogen atoms or linear or branched alkyl having 1 to 10 carbon atoms. Represents a group.) Represents a group selected from
A ⁴ and ^{A 6} are each independently 1,4-phenylene group, 1,4-cyclohexylene group, bicyclo [2.2.2] octane-1,4-diyl group, pyridine-2,5-diyl group , Pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, tetrahydro represents a-2,5-diyl group or 1,3-dioxane-2,5-diyl group may be substituted by or one or more substituents L ⁵ or these groups are unsubstituted , if a ⁴ there are a plurality thereof may be the same or different and they if a ⁶ there are a plurality may be the same or different and
L ⁵ is a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfanyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropyl. Amino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or one or more -CH _2- are independently -O-, -S-, -CO-, -COO-, -OCO-, -CO. -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH Linear or branched alkyl with 1 to 20 carbon atoms which may be substituted with = CH-, -OCO-CH = CH-, -CH = CH-, -CF = CF- or -C≡C- represents a group, any hydrogen atom in the alkyl group may be substituted by fluorine atoms, they if which L ⁵ presence of a plurality may have the same or different and
Z ³ , Z ⁴ , Z ⁵ and Z ⁶ are independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, respectively. -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH -CO-NH-, -NH-O-, -O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _{2- , -CH 2 CH 2 -COO -,} - CH 2 CH 2 -OCO -, - COO-CH 2 -, - OCO-CH 2 -, - CH 2 -COO -, - CH 2 -OCO -, - CH = Represents CH-, -N = N-, -CH = N-, -N = CH-, -CH = N-N = CH-, -CF = CF-, -C≡C- or a single bond, but Z ³ they if there exist a plurality may be the same or different and they if Z ⁴ there are a plurality may be the same or different and
m2 and m3 independently represent 0, 1, 2 or 3, respectively. The liquid crystal composition according to any one of claims 1 to 6, which is a compound represented by). The compound (B) has the following general formula (II-iii).

(In the formula, R ²³ is a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms, or the following formula (R2T3).

(In the formula, the broken line represents the bond position.)
A ⁵³ is the following equation (A53-1) and equation (A53-3).

(In the formula, the broken line represents the bond position, and R ^f3 represents a hydrogen atom, a methyl group, an ethyl group, or a propyl group.)
Z ³³ represents −CH ₂ CH _2- or single bond
m23 represents 0 or 1. The liquid crystal composition according to any one of claims 1 to 7, which is a compound represented by). The following general formula (III)

(In the formula, R ³ and R ⁴ are independently alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 7 carbon atoms, alkenyl groups having 2 to 8 carbon atoms, or carbon atoms 2 to 7 respectively. Represents the alkenyloxy group of
B ¹ and B ² are independently expressed from the following equations (B-1) to (B-10).

(Wherein the dashed line represents. A binding position) represents a group selected from, if the B ² there is a plurality thereof may be the same or different and
m4 represents an integer from 1 to 4. The liquid crystal composition according to any one of claims 1 to 8, which contains the compound represented by). The following general formula (IV)

(In the formula, R ⁵ and R ⁶ are independently alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 7 carbon atoms, alkenyl groups having 2 to 8 carbon atoms, or carbon atoms 2 to 7 respectively. Represents the alkenyloxy group of
B ³ and B ⁴ are independently expressed by the following equations (B-11) to (B-19).

(Wherein the dashed line represents. A binding position) represents a group selected from, if B ³ there are a plurality of them may be the same or different and the same case those B ⁴ there are a plurality of Can be different
Z ⁷ and Z ⁸ are independently -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, -OCO-, -CO. -S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH- COO-, -CH = CH-OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _2- , -CH ₂ CH ₂ -COO-, -CH ₂ CH _2- OCO-, -COO-CH _2- , -OCO-CH _2- , -CH _2- COO-, -CH ₂ -OCO-, -CH = CH-, -N = N -, - CH = N - , - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, ^{if Z 7} there are a plurality of they may be the same or different and they if Z ⁸ there are a plurality may be the same or different and
m5 and m6 independently represent integers from 0 to 3, while m5 + m6 represent integers from 1 to 3. The liquid crystal composition according to any one of claims 1 to 9, which contains the compound represented by). The following general formula (V)

(Wherein, ^{P 4} and ^{P 5} each independently formula from the formula (P-8) below (P-17)

(In the formula, the broken line represents the bond position.) Represents the group selected from
Sp ⁷ and Sp ⁸ each independently represent a spacer group or a single bond.
B ⁵ and B ⁶ are independently derived from the following equations (B-20) to (B-28).

(In the formula, the broken line represents the bond position, L ⁵ is a halogen atom, a cyano group, a nitro group, a pentafluorosulfanyl group, an amino group which may be substituted, a silyl group which may be substituted, or an arbitrary hydrogen atom. May be replaced with a fluorine atom, and one or more -CH ₂ −s are independently −O−, −S−, −CO−, −COO−, −OCO−, −CO−S−, − S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH = CH-,- OCO-CH = CH -, - CH = CH -, - CF = CF- or -C≡C- alkyl group having 20 good 1 -C be replaced by, ^or, P L -Sp ^L - Table with groups (wherein, P ^L is a radical polymerization, a group of polymerization by cationic polymerization or anionic polymerization, Sp ^L represents. a spacer group or a single bond) represents a, they if which L ⁵ there are multiple represents a group selected from the same or different from.), if the B ⁶ there are a plurality of them may be the same or different and
Z ⁹ is -O-, -S-, -OCH _2- , -CH ₂ O-, -CH ₂ CH _2- , -CO-, -COO-, -OCO-, -CO-S-, -S- CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-,- O-NH-, -SCH _2- , -CH ₂ S-, -CF ₂ O-, -OCF _2- , -CF ₂ S-, -SCF _2- , -CH = CH-COO-, -CH = CH -OCO-, -COO-CH = CH-, -OCO-CH = CH-, -COO-CH ₂ CH _2- , -OCO-CH ₂ CH _2- , -CH ₂ CH _2- COO-, -CH ₂ CH _2- OCO-, -COO-CH _2- , -OCO-CH _2- , -CH _2- COO-, -CH _2- OCO-, -CH = CH-, -N = N-, -CH = N -, - N = CH -, - CH = N-N = CH -, - CF = CF -, - C≡C- or represents a single bond, even they are the same ^{if Z 9} there are a plurality of May be different
m7 represents an integer from 1 to 4. The liquid crystal composition according to any one of claims 1 to 10, which contains the compound represented by). A liquid crystal display device manufactured by using the liquid crystal composition according to any one of claims 1 to 11.