WO2018198793A1

WO2018198793A1 - Composition and method for composition storage

Info

Publication number: WO2018198793A1
Application number: PCT/JP2018/015356
Authority: WO
Inventors: 宏之伊藤; 彰宏小磯; 礼貴細野; 直美幡野; 淳子山本
Original assignee: Dic株式会社
Priority date: 2017-04-25
Filing date: 2018-04-12
Publication date: 2018-11-01
Also published as: JPWO2018198793A1

Abstract

The present invention is a composition held in an airtight container and containing substantially one type of liquid crystal compound and an additive that prevents deterioration of the liquid crystal compound, and the present invention provides a liquid crystal composition that uses a liquid crystal compound obtained by this production method. The present invention is also a simple recrystallization method that yields a liquid crystal compound having high specific resistance. According to the present invention, substantially one type of liquid crystal compound can be subjected to long-term storage while maintaining a high purity level. By mixing the liquid crystal compound according to the present invention with another liquid crystal compound, a highly stable liquid crystal composition is obtained and a liquid crystal display element having an excellent reliability is also obtained.

Description

Composition and method for storing composition

The present invention relates to a liquid crystal compound for long-term storage and a storage method.

Liquid crystal display elements have come to be widely used from consumer applications such as LCD TVs, mobile phones and personal computers to industrial applications. These products have a relatively long product life of several years to several tens of years, and operate normally during this period. Therefore, liquid crystal materials used for these products are required to have high stability. A specific stability index of a liquid crystal material is a specific resistance value. In order for the liquid crystal display element to operate normally, the specific resistance value of the liquid crystal material used for the liquid crystal display element must be sufficiently high, and deterioration over time must be suppressed.

On the other hand, there are various requirements for liquid crystal materials such as high-speed response and high contrast. These physical properties cannot be achieved by a single compound, and a plurality of liquid crystal compounds are mixed to meet the demand as a liquid crystal composition. At that time, it is important that each liquid crystal compound is accurately weighed and its mixing ratio is adjusted to the target value. This is because if an error occurs in the mixing ratio, the physical properties change, and a liquid crystal composition that satisfies the requirements cannot be prepared.

In order to improve the stability of the liquid crystal composition, it is known that an additive such as an antioxidant or a light stabilizer is added to the specific liquid crystal composition to suppress deterioration of the liquid crystal composition and improve reliability. (See Patent Document 1, Patent Document 2, and Patent Document 3).

In order to obtain a liquid crystal composition having a high specific resistance value, each liquid crystal compound constituting the liquid crystal composition must also have a high specific resistance value. In order to improve the stability of a liquid crystal compound, it has been conventionally studied to increase the purity of the compound (see Patent Document 4). Therefore, there has been no application of a directional method in which another substance is added to a liquid crystal compound that requires a very high purity to lower the purity. Further, it is considered that when an additive is added to a compound, there is a demerit that it is difficult to control the amount of the additive present together with the compound when preparing a composition by preparing a plurality of compounds.

By the way, the storage stability of the liquid crystal compound in the state of one kind of compound, which is a pre-stage adjusted to the liquid crystal composition, is also important. The liquid crystal compound is usually subjected to transportation and long-term storage after production, and therefore it may be placed under high temperature conditions. Therefore, some liquid crystal compounds have a problem that they deteriorate during storage of the liquid crystal compounds. In recent years, liquid crystal display devices have been required to have higher stability, but no specific means for storing them for a long period of time while maintaining a high level of purity of the compound has been reported.

JP 2002-256267 A Special table 2014-505745 Special table 2014-505746 Special table 2011-121909

The problem to be solved by the present invention is to provide a composition that can be stored for a long period of time while maintaining a high level of purity of substantially one kind of liquid crystal compound, and substantially one kind of liquid crystal compound. Is to be stored while maintaining a high level of purity.

As a result of intensive investigations in view of the above-described circumstances, the inventors of the present invention have added an additive for preventing the liquid crystal compound from being altered to form a composition, which is contained in an airtight container as described above. The present inventors have found that the problem can be solved and have completed the present invention.

That is, the present invention provides a composition that contains substantially one type of liquid crystal compound and an additive that prevents alteration of the liquid crystal compound and is contained in an airtight container.

The liquid crystal composition of the present invention can store one type of liquid crystal compound for a long period of time while maintaining a high level of purity. Therefore, by preparing a liquid crystal composition in which a plurality of liquid crystal compounds are mixed using the liquid crystal composition of the present invention, a liquid crystal for producing a liquid crystal display element having higher stability and usable for a long period of time. A composition can be obtained.

In the present invention, “substantially one type of liquid crystal compound” is composed of one type of liquid crystal compound, but in one type of liquid crystal compound, impurities inevitably mixed when the liquid crystal compound is produced. It may mean that it may contain. In general, liquid crystal compounds are manufactured through a purification process, but it is difficult to completely eliminate impurities even after the purification process. Contains a little. Thus, even if it is manufactured as one type of liquid crystal compound, it inevitably contains impurities, so it is referred to as “substantially one type of liquid crystal compound”.

The liquid crystal compound is preferably a compound represented by the general formula (I).

(In the formula, R ^I1 is an aldehyde group, amino group, carboxyl group, tosyl group, mesyl group, triflate group, hydroxy group, hydroxymethyl group, nitro group, sulfo group, cyano group, acid chloride group, chlorine atom, bromine. Represents an atom, an iodine atom, or an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —CH═CH—, — Optionally substituted by C≡C—, —O—, —CO—, —COO— or —OCO—,
A ^I1 and ^{A I2} are each independently (a) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - is -O (It may be replaced with-.)
(B) a 1,4-phenylene group (one —CH═ present in the group or two or more non-adjacent —CH═ may be replaced by —N═) and (c) 1,4-cyclohexenylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group (naphthalene-2 , 6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, one —CH═ or two or more non-adjacent —CH═ is —N═ The hydrogen atom present in these groups may be substituted with a fluorine atom.
The group (a), the group (b) and the group (c) are each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^I1 is a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —OCF ₂ —, —CF ₂ O— -CH = NN-CH-, -CH = CH-, -CF = CF- or -C≡C-
R ^I2 is an aldehyde group, amino group, carboxyl group, tosyl group, mesyl group, triflate group, hydroxy group, hydroxymethyl group, nitro group, sulfo group, acid chloride group, bromine atom, iodine atom, or hydrogen atom, Represents a fluorine atom, a chlorine atom, a cyano group or an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —CH═CH— , —C≡C—, —O—, —CO—, —COO— or —OCO—, and one or more hydrogen atoms in the alkyl group may be substituted with fluorine atoms May have been
m ^I1 represents an 1, 2, 3 or ^4, if ^{m I1} is representative of the 2, 3 or 4, ^{A I1} and ^{Z I1} existing in plural numbers may be different, even the same. )
In general formula (I), any one or more of R ^I1 and R ^I2 preferably have a —CH═CH— or —C≡C— structure in the group. Since a compound having such a structure is easily deteriorated and deteriorated, the effect of improving stability by storing it together with an additive for preventing deterioration of the liquid crystal compound is great.

Further, it is preferable that the general formula (I) is a compound exhibiting liquid crystallinity near room temperature. A compound that exhibits liquid crystallinity near room temperature tends to deteriorate and deteriorate compared to a compound that does not exhibit liquid crystallinity near room temperature, so stability by storing it with an additive that prevents the liquid crystal compound from deteriorating. Great improvement effect. For example, when the general formula (I) represents a skeleton of “-1,4-cyclohexylene group-1,4-phenylene group-1,4-phenylene group—” as shown below, the liquid crystallinity near room temperature It is easy to show.

^{(Wherein, R I1} and ^{R I2} are respectively a general formula (I) ^{R I1} and ^{R I2} in the same meaning.)
Moreover, it is preferable that the general formula (I) is a compound having a highly reactive benzyl position. Since a compound having a benzyl position is likely to be deteriorated and deteriorated, the effect of improving stability by storing together with an additive for preventing deterioration of the liquid crystal compound is great.

Moreover, it is preferable that general formula (I) is a compound which is easy to contain "the trace impurities which are easy to change and deteriorate. Even for compounds that are likely to contain the “trace impurities that easily deteriorate due to alteration”, the effect of improving stability is great by storing them together with additives that prevent alteration. As a trace impurity, it is effective for a trace impurity having a structure of an alkenyl group or an alkenyloxy group.
<First embodiment of compound represented by formula (I)>
The compound represented by the general formula (I) is preferably a compound selected from the compounds represented by the following general formulas (N-1), (N-2) and (N-3). These compounds correspond to dielectrically negative compounds (the sign of Δε is negative and the absolute value is greater than 2).

(In the formula, R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31 and R ^N32 are each independently an aldehyde group, amino group, carboxyl group, tosyl group, mesyl group, triflate group, hydroxy group, hydroxymethyl group. , A nitro group, a sulfo group, a cyano group, an acid chloride group, a chlorine atom, a bromine atom, an iodine atom, or an alkyl group having 1 to 8 carbon atoms, one in the alkyl group or two or more adjacent to each other Each of —CH ₂ — may be independently substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—,
A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31, and A ^N32 are each independently (a) a 1,4-cyclohexylene group (one —CH ₂ — or adjacent to each other in this group). Two or more —CH ₂ — that are not present may be replaced by —O—.)
(B) a 1,4-phenylene group (one —CH═ present in the group or two or more non-adjacent —CH═ may be replaced by —N═) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, one —CH═ or two or more non-adjacent —CH═ may be replaced by —N═.
(D) represents a group selected from the group consisting of 1,4-cyclohexenylene groups, and the groups (a), (b), (c) and (d) are each independently a cyano group, It may be substituted with a fluorine atom or a chlorine atom,
Z ^N11 , Z ^N12 , Z ^N21 , Z ^N22 , Z ^N31 and Z ^N32 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—. , —COO—, —OCO—, —OCF ₂ —, —CF ₂ O—, —CH═N—N═CH—, —CH═CH—, —CF═CF— or —C≡C—,
^XN21 represents a hydrogen atom or a fluorine atom,
T ^N31 represents —CH ₂ — or an oxygen atom,
n ^N11 , n ^N12 , n ^N21 , n ^N22 , n ^N31, and n ^N32 each independently represent an integer of 0 to 3, but n ^N11 + n ^N12 , n ^N21 + n ^N22, and n ^N31 + n ^N32 are each independently When there are a plurality of A ^N11 to A ^N32 and Z ^N11 to Z ^N32 , they may be the same or different. )
The compounds represented by the general formulas (N-1), (N-2) and (N-3) are preferably compounds having a negative Δε and an absolute value larger than 3.

In the general formulas (N-1), (N-2) and (N-3), R ^N11 , R ^N12 , R ^N21 , R ^N22 , R ^N31 and R ^N32 each independently represent 1 to 8 carbon atoms. An alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, An alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is preferable. More preferably, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms (propenyl group) is particularly preferable. From the viewpoint of the effect of improving stability by storing together with the additive, any one or more of R ^N11 and R ^N12 are preferably an alkenyl group or an alkenyloxy group, and any one of R ^N21 and R ^N22 One or more are preferably an alkenyl group or an alkenyloxy group, and one or more of R ^N31 and R ^N32 are preferably an alkenyl group or an alkenyloxy group.

Further, when the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and carbon An alkenyl group having 4 to 5 atoms is preferable, and when the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a straight chain A straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear. From the viewpoint of the effect of improving stability by storing together with the additive, any one or more of R ^N11 and R ^N12 are preferably an alkenyl group or an alkenyloxy group, and any one of R ^N21 and R ^N22 One or more are preferably an alkenyl group or an alkenyloxy group, and one or more of R ^N31 and R ^N32 are preferably an alkenyl group or an alkenyloxy group.

The alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dots in each formula represent carbon atoms in the ring structure.)

A ^N11 , A ^N12 , A ^N21 , A ^N22 , A ^N31, and A ^N32 are preferably aromatic when it is required to increase Δn independently, and in order to improve the response speed, fat Preferably a trans-1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5 -Difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1 , 4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group Preferred, it is more preferable that represents the following structures,

More preferably, it represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group.

^{^{^{^{Z N11, Z N12, Z N21}}}} , Z N22, Z N31 and ^{Z N32} _-CH 2 each _{independently} _{O -, - CF 2 O -} , - CH 2 CH 2 -, - CF 2 CF 2 - or a single bond preferably represents _{_{an, -CH 2 O -, - CH}} 2 CH 2 - or a single bond is more preferable, _-CH 2 O-or a single bond is particularly preferred.

^XN21 is preferably a fluorine atom.

T ^N31 is preferably an oxygen atom.

n ^N11 + n ^N12 , n ^N21 + n ^N22 and n ^N31 + n ^N32 are preferably 1 or 2, a combination in which n ^N11 is 1 and n ^N12 is 0, a combination in which n ^N11 is 2 and n ^N12 is 0, n ^A combination in which ^N11 is 1 and n ^N12 is 1, a combination in which n ^N11 is 2 and n ^N12 is 1, a combination in which n ^N21 is 1 and n ^N22 is 0, n ^N21 is 2 and n ^N22 is n A combination in which n ^N31 is 1 and n ^N32 is 0, and a combination in which n ^N31 is 2 and n ^N32 is 0 are preferable.

Examples of the compound represented by the general formula (N-1) include compounds represented by the following general formulas (N-1a) to (N-1g).

^{(Wherein, R N11} and ^{R N12} are as defined ^{R N11} and ^{R N12} in the general formula ^{(N-1), n Na11} represents 0 or ^{1, n NB11} represents 0 or ^{1, n NC11} is ^Represents 0 or 1, n ^Nd11 represents 0 or 1, n ^Ne11 represents 1 or 2, n ^Nf11 represents 1 or 2, n ^Ng11 represents 1 or 2, A ^Ne11 represents trans-1,4 ^{-Represents a} cyclohexylene group or a 1,4-phenylene group, and A ^Ng11 represents a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group, but at least one Represents a 1,4-cyclohexenylene group, and Z ^Ne ¹¹ represents a single bond or ethylene, but at least one represents ethylene.)
More specifically, the compound represented by the general formula (N-1) is a compound selected from the group of compounds represented by the general formulas (N-1-1) to (N-1-21). preferable.

The compound represented by the general formula (N-1-1) is the following compound.

( ^Wherein , R ^N111 and R ^N112 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
R ^N111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a propyl group, a pentyl group or a vinyl group. ^RN112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group or a butoxy group.

Further, the compound represented by the general formula (N-1-1) is a compound selected from the group of compounds represented by the formula (N-1-1.1) to the formula (N-1-1.23). Preferably, it is a compound represented by the formulas (N-1-1.1) to (N-1-1.4), and the formula (N-1-1.1) and the formula (N The compound represented by -1-1.3) is preferable.

The compound represented by the general formula (N-1-2) is the following compound.

(In the formula, R ^N121 and R ^N122 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
^RN121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, a butyl group or a pentyl group. ^RN122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and includes a methyl group, a propyl group, a methoxy group, an ethoxy group, or a propoxy group. preferable.

Further, the compound represented by the general formula (N-1-2) is a compound selected from the group of compounds represented by the formula (N-1-2.1) to the formula (N-1-2.22). It is preferable that the formula (N-1-2.3) to the formula (N-1-2.7), the formula (N-1-2.10), the formula (N-1-2.11), the formula A compound represented by formula (N-1-2.13) and formula (N-1-2.20) is preferred. When importance is attached to the improvement of Δε, formula (N-1-2.3) is preferably a compound represented by the formula (N-1-2.7) _from when emphasizing improvements in _{T NI} formula (N-1-2.10), formula (N-1-2.11) And a compound represented by the formula (N-1-2.13), and when emphasizing improvement in response speed, the compound represented by the formula (N-1-2.20) Is preferred.

The compound represented by the general formula (N-1-3) is the following compound.

( ^Wherein , R ^N131 and R ^N132 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
R ^N131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. R ^N132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably a 1-propenyl group, an ethoxy group, a propoxy group or a butoxy group. .

Since the compound represented by the general formula (N-1-3) is a compound that is relatively likely to contain “a small amount of impurities that are easily deteriorated and deteriorated”, it can be stabilized by storing it with an additive that prevents deterioration. Greatly improves the performance. By storing together with the additive, alteration of trace impurities can be suppressed, so that deterioration of the entire composition including the compound represented by the general formula (N-1-3) can be suppressed.

Further, the compound represented by the general formula (N-1-3) is a compound selected from the group of compounds represented by the formula (N-1-3.1) to the formula (N-1-3.21). It is preferably a compound represented by the formulas (N-1-3.1) to (N-1-3.7) and the formula (N-1-3.21). -1-3.1), formula (N-1-3.2), formula (N-1-3.3), formula (N-1-3.4) and formula (N-1-3.6) ) Is preferred.

The compound represented by the general formula (N-1-4) is the following compound.

^{(Wherein, R N141} and ^{R N142} each independently represents the same meaning as ^{R N11} and ^{R N12} in the general formula (N-1).)
R ^N141 and ^{R N142} are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group or an alkoxy group having 1 to 4 carbon atoms carbon atoms 4-5 preferably a methyl group, a propyl group, an ethoxy Group or butoxy group is preferred.

When the compound represented by the general formula (N-1-4) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (N-1-4) is a compound selected from the group of compounds represented by the formula (N-1-4.1) to the formula (N-1-4.14). Preferably, it is a compound represented by the formulas (N-1-4.1) to (N-1-4.4), and the formula (N-1-4.1) and the formula (N -1-4.2) and compounds represented by formula (N-1-4.4) are preferred.

The compound represented by the general formula (N-1-5) is the following compound.

(In the formula, R ^N151 and R ^N152 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1).)
R ^N151 and R ^N152 are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group. Is preferred.

In the case where the compound represented by the general formula (N-1-5) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (N-1-5) is a compound selected from the group of compounds represented by the formula (N-1-5.1) to the formula (N-1-5.6). It is preferable that the compound represented by formula (N-1-5.1), formula (N-1-5.2) and formula (N-1-5.4) is preferable.

The compound represented by the general formula (N-1-10) is the following compound.

(In the formula, R ^N1101 and R ^N1102 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1).)
R ^N1101 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. R ^N1102 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

Further, the compound represented by the general formula (N-1-10) is a compound selected from the group of compounds represented by the formula (N-1-10.1) to the formula (N-1-10.21). It is preferable that they are represented by formulas (N-1-10.1) to (N-1-10.5), formula (N-1-10.20) and formula (N-1-10.21). The compound is preferably a compound of formula (N-1-10.1), formula (N-1-10.2), formula (N-1-10.20) and formula (N-1-10.21). The compound represented by these is preferable.

The compound represented by the general formula (N-1-11) is the following compound.

(In the formula, R ^N1111 and R ^N1112 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1).)
R ^N1111 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. R ^N1112 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

Further, the compound represented by the general formula (N-1-11) is a compound selected from the group of compounds represented by the formula (N-1-11.1) to the formula (N-1-11.15). Preferably, it is a compound represented by the formulas (N-1-11.1) to (N-1-11.15), and is preferably a compound represented by the formula (N-1-11.2) or the formula (N-- The compound represented by 1-11.4) is preferable.

The compound represented by the general formula (N-1-12) is the following compound.

( ^Wherein , R ^N1121 and R ^N1122 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
^RN1121 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. ^RN1122 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-13) is the following compound.

( ^Wherein , R ^N1131 and R ^N1132 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
R ^N1131 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. R ^N1132 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-14) is the following compound.

( ^Wherein , R ^N1141 and R ^N1142 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
R ^N1141 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. R ^N1142 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

In the case where the compound represented by the general formula (N-1-14) represents a compound having a benzyl position, the effect of improving the stability is great by storing together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

The compound represented by the general formula (N-1-15) is the following compound.

( ^Wherein , R ^N1151 and R ^N1152 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
^RN1151 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. R ^N1152 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-16) is the following compound.

(In the formula, R ^N1161 and R ^N1162 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1).)
R ^N1161 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. R ^N1162 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

In the case where the compound represented by the general formula (N-1-16) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

The compound represented by the general formula (N-1-17) is the following compound.

( ^Wherein , R ^N1171 and R ^N1172 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
^RN1171 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group. R ^N1172 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

The compound represented by the general formula (N-1-18) is the following compound.

( ^Wherein , R ^N1181 and R ^N1182 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
^RN1181 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a methyl group, an ethyl group, a propyl group or a butyl group. R ^N1182 is preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group, or a butoxy group.

In the case where the compound represented by the general formula (N-1-18) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (N-1-18) is a compound selected from the group of compounds represented by the formula (N-18.1) to the formula (N-1-18.5). Preferably, it is a compound represented by the formulas (N-18.1. 1) to (N-1-11.3), and is preferably a compound represented by the formula (N-1-18.2) or the formula (N- The compound represented by 1-18.3) is preferred.

The compound represented by the general formula (N-1-20) is the following compound.

(In the formula, R ^N1201 and R ^N1202 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1).)
R ^N1201 and R ^N1202 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.

The compound represented by the general formula (N-1-21) is the following compound.

(In the formula, R ^N1211 and R ^N1212 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1).)
R ^N1211 and R ^N1212 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.

The compound represented by the general formula (N-1-22) is the following compound.

( ^Wherein , R ^N1221 and R ^N1222 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-1)).
R ^N1221 and R ^N1222 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group, or a butyl group.

Further, the compound represented by the general formula (N-1-22) is a compound selected from the group of compounds represented by the formula (N-1-22.1) to the formula (N-1-22.12). Preferably, it is a compound represented by formulas (N-1-22.1) to (N-1-22.5), and preferably represented by formulas (N-1-22.1) to (N- The compound represented by 1-22.4) is preferred.

The compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formula (N-3-2).

(In the formula, R ^N321 and R ^N322 each independently represent the same meaning as R ^N11 and R ^N12 in formula (N-3).)
R ^N321 and R ^N322 are preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group or a pentyl group.

Further, the compound represented by the general formula (N-3-2) is a compound selected from the group of compounds represented by the formula (N-3-2.1) to the formula (N-3-2.3). Preferably there is.

<Second embodiment of compound represented by formula (I)>
The compound represented by the general formula (I) is preferably a compound represented by the general formula (J). These compounds correspond to dielectrically positive compounds (Δε is greater than 2).

(In the formula, R ^J1 is an aldehyde group, amino group, carboxyl group, tosyl group, mesyl group, triflate group, hydroxy group, hydroxymethyl group, nitro group, sulfo group, cyano group, acid chloride group, chlorine atom, bromine atom. Represents an iodine atom or an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —CH═CH—, —C≡. Optionally substituted by C—, —O—, —CO—, —COO— or —OCO—,
n ^J1 represents 0, 1, 2, 3 or 4;
A ^J1 , A ^J2 and A ^J3 are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O-.)
(B) a 1,4-phenylene group (one —CH═ present in the group or two or more non-adjacent —CH═ may be replaced by —N═) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, one —CH═ or two or more non-adjacent —CH═ may be replaced by —N═.
The group (a), the group (b) and the group (c) are each independently selected from the group consisting of cyano group, fluorine atom, chlorine atom, methyl group, trifluoromethyl group or trifluoro May be substituted with a methoxy group,
Z ^J1 and Z ^J2 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O—, Represents —COO—, —OCO— or —C≡C—,
When n ^J1 is 2, 3 or 4 and a plurality of A ^J2 are present, they may be the same or different, and n ^J1 is 2, 3 or 4 and a plurality of Z ^J1 is present. If they are the same or different,
X ^J1 is an aldehyde group, amino group, carboxyl group, tosyl group, mesyl group, triflate group, hydroxy group, hydroxymethyl group, nitro group, sulfo group, acid chloride group, bromine atom, iodine atom, or hydrogen atom, fluorine An atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, or a 2,2,2-trifluoroethyl group is represented. )
In general formula (J), R ^J1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or alkenyloxy having 2 to 8 carbon atoms. A group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable. An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferable, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms. (Propenyl group) is particularly preferred.

R ^J1 is preferably an alkyl group when emphasizing reliability, and is preferably an alkenyl group when emphasizing a decrease in viscosity. From the viewpoint of the effect of improving the stability by storing together with the additive, R ^J1 is preferably an alkenyl group or an alkenyloxy group.

Further, when the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and carbon An alkenyl group having 4 to 5 atoms is preferable, and when the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a straight chain A straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear.

The alkenyl group is preferably selected from groups represented by any of the formulas (R1) to (R5). (The black dot in each formula represents the carbon atom in the ring structure to which the alkenyl group is bonded.)

A ^J1 , A ^J2 and A ^J3 are preferably aromatic when it is required to independently increase Δn, and are preferably aliphatic to improve the response speed. 1,4-cyclohexylene group, 1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene -2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, preferably substituted by a fluorine atom It is more preferable to represent the following structure,

It is more preferable to represent the following structure.

Z ^J1 and Z ^J2 each independently preferably represent —CH ₂ O—, —OCH ₂ —, —CF ₂ O—, —CH ₂ CH ₂ —, —CF ₂ CF ₂ — or a single bond, OCH ₂ —, —CF ₂ O—, —CH ₂ CH ₂ — or a single bond is more preferred, and —OCH ₂ —, —CF ₂ O— or a single bond is particularly preferred.

X ^J1 is preferably a fluorine atom or a trifluoromethoxy group, and more preferably a fluorine atom.

n ^J1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, preferably 0 or 1 when emphasizing the improvement of Δε, and preferably 1 or 2 when emphasizing Tni .

The compound represented by the general formula (J) is preferably a compound represented by the general formula (M). The compound represented by the general formula (M) corresponds to a dielectrically positive compound (Δε is greater than 2).

(Wherein R ^M1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —CH═CH—, — Optionally substituted by C≡C—, —O—, —CO—, —COO— or —OCO—,
n ^M1 represents 0, 1, 2, 3 or 4;
A ^M1 and A ^M2 are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O- or -S- And (b) a 1,4-phenylene group (one —CH═ present in this group or two or more non-adjacent —CH═ may be replaced by —N═).
A hydrogen atom on the group (a) and the group (b) may be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^M1 and Z ^M2 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O—, Represents —COO—, —OCO— or —C≡C—,
When n ^M1 is 2, 3 or 4 and a plurality of A ^M2 are present, they may be the same or different, and n ^M1 is 2, 3 or 4 and a plurality of Z ^M1 is present If they are the same or different,
X ^M1 and X ^M3 each independently represent a hydrogen atom, a chlorine atom or a fluorine atom,
X ^M2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, or a 2,2,2-trifluoroethyl group.

In the general formula (M), R ^M1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or an alkenyloxy having 2 to 8 carbon atoms. A group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable. An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferable, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms. (Propenyl group) is particularly preferred.

R ^M1 is preferably an alkyl group when emphasizing reliability, and is preferably an alkenyl group when emphasizing a decrease in viscosity.

A ^M1 and A ^M2 are preferably aromatic when it is required to independently increase Δn, and are preferably aliphatic for improving the response speed, and trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2, 3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It preferably represents a diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably represents the following structure:

It is more preferable to represent the following structure.

Z ^M1 and ^{Z M2} each _{independently} _{-CH 2 O -, - CF 2} O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, _-CF 2 O-, —CH ₂ CH ₂ — or a single bond is more preferable, and —CF ₂ O— or a single bond is particularly preferable.

n ^M1 is preferably 0, 1, 2, or 3, preferably 0, 1 or 2, preferably 0 or 1 when emphasizing the improvement of Δε, and preferably 1 or 2 when emphasizing Tni .

The compound represented by the general formula (M) is preferably, for example, a compound selected from the group of compounds represented by the general formula (M-1).

(Wherein R ^M11 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^M11 to X ^M15 each independently represents hydrogen. represents an atom or a fluorine ^{atom, Y M11} represents a fluorine atom or OCF _3.)
When the compound represented by the general formula (M-1) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (M-1) is specifically preferably a compound represented by the formula (M-1.1) to the formula (M-1.4). A compound represented by M-1.1) or formula (M-1.2) is preferred, and a compound represented by formula (M-1.2) is more preferred. It is also preferred to use the compounds represented by formula (M-1.1) or formula (M-1.2) at the same time.

Furthermore, the compound represented by the general formula (M) is preferably a compound selected from the group of compounds represented by the general formula (M-2), for example.

(Wherein R ^M21 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^M21 and X ^M22 each independently represent hydrogen represents an atom or a fluorine ^{atom, Y M21} represents a fluorine atom, a chlorine atom or OCF _3.)
Further, the compound represented by the general formula (M-2) is preferably a compound represented by the formula (M-2.1) to the formula (M-2.5). 3) or / and a compound represented by the formula (M-2.5) is preferable.

The compound represented by the general formula (M) used in the composition of the present invention is preferably a compound represented by the general formula (M-3).

(Wherein R ^M31 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^M31 to X ^M36 are each independently hydrogen. represents an atom or a fluorine ^{atom, Y M31} represents a fluorine atom, a chlorine atom or OCF _3.)
Furthermore, the compound represented by the general formula (M-3) used in the composition of the present invention is specifically represented by the formula (M-3.1) to the formula (M-3.8). A compound is preferable, and among them, a compound represented by Formula (M-3.1) and / or Formula (M-3.2) is preferably contained.

Furthermore, the compound represented by the general formula (M) is preferably a compound selected from the group represented by the general formula (M-4).

(Wherein R ^M41 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^M41 to X ^M48 are each independently fluorine. Represents an atom or a hydrogen atom, and Y ^M41 represents a fluorine atom, a chlorine atom or OCF _3. )
When the compound represented by the general formula (M-4) represents a compound having a benzyl position, the effect of improving the stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Furthermore, the compound represented by the general formula (M-4) used in the composition of the present invention is specifically represented by the formula (M-4.1) to the formula (M-4.4). Preferably, it is a compound, and among them, it is preferable to contain a compound represented by the formula (M-4.2) to the formula (M-4.4), and a compound represented by the formula (M-4.2) It is more preferable to contain.

Furthermore, the compound represented by the general formula (M) is preferably a compound represented by the general formula (M-5).

(Wherein R ^M51 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^M51 and X ^M52 are each independently hydrogen. represents an atom or a fluorine ^{atom, Y M51} represents a fluorine atom, a chlorine atom or OCF _3.)
Further, the compound represented by the general formula (M-5) is preferably a compound represented by the formula (M-5.1) to the formula (M-5.4), and the formula (M-5. A compound represented by formula (M-5.4) is preferable.

Further, the compound represented by the general formula (M-5) is preferably a compound represented by the formula (M-5.11) to the formula (M-5.17), and the formula (M-5. 11), a compound represented by formula (M-5.13) and formula (M-5.17) is preferable.

Further, the compound represented by the general formula (M-5) is preferably a compound represented by the formula (M-5.21) to the formula (M-5.28), and the formula (M-5. 21), a compound represented by formula (M-5.22), formula (M-5.23) and formula (M-5.25).

Furthermore, the compound represented by the general formula (M) is preferably a compound represented by the general formula (M-6).

(Wherein R ^M61 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^M61 to X ^M64 are each independently fluorine. Represents an atom or a hydrogen atom, and Y ^M61 represents a fluorine atom, a chlorine atom or OCF ₃ )
Further, the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.1) to the formula (M-6.4). It is preferable to contain a compound represented by M-6.2) and formula (M-6.4).

Further, the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.11) to the formula (M-6.14). It is preferable to contain a compound represented by M-6.12) and formula (M-6.14).

Further, the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.21) to the formula (M-6.24). It is preferable to contain a compound represented by formula (M-6.21), formula (M-6.22) and formula (M-6.24).

Furthermore, the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.31) to the formula (M-6.34). Among them, it is preferable to contain a compound represented by the formula (M-6.31) and the formula (M-6.32).

Further, the compound represented by the general formula (M-6) is specifically preferably a compound represented by the formula (M-6.41) to the formula (M-6.44). It is preferable to contain a compound represented by M-6.42).

Furthermore, the compound represented by the general formula (M) is preferably a compound selected from the group of compounds represented by the general formula (M-7).

(Wherein, X ^M71 to X ^M76 each independently represents a fluorine atom or a hydrogen atom, and R ^M71 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or 1 to 4 represents an alkoxy group, and Y ^M71 represents a fluorine atom or OCF _3. )
In the case where the compound represented by the general formula (M-7) represents a compound having a benzyl position, the effect of improving the stability is great by storing together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (M-7) is preferably a compound represented by the formula (M-7.1) to the formula (M-7.4), and the formula (M-7. It is preferable that it is a compound represented by 2).

Furthermore, the compound represented by the general formula (M-7) is preferably a compound represented by the formula (M-7.11) to the formula (M-7.14), and the formula (M-7. 11) and a compound represented by the formula (M-7.12) are preferable.

Further, the compound represented by the general formula (M-7) is preferably a compound represented by the formula (M-7.21) to the formula (M-7.24). 21) and a compound represented by the formula (M-7.22) are preferable.

Furthermore, the compound represented by the general formula (M) is preferably a compound represented by the general formula (M-8).

( ^Wherein , X ^M81 to X ^M84 each independently represents a fluorine atom or a hydrogen atom, Y ^M81 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M81 represents an alkyl group having 1 to 5 carbon atoms, Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and A ^M81 and A ^M82 are each independently 1,4-cyclohexylene group, 1,4-phenylene group or

However, the hydrogen atom on the 1,4-phenylene group may be substituted with a fluorine atom. )
When the compound represented by the general formula (M-8) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Furthermore, the compound represented by the general formula (M-8) used in the composition of the present invention is specifically represented by the formula (M-8.1) to the formula (M-8.4). Preferably, it is a compound, and among them, it is preferable to contain a compound represented by formula (M-8.1) or formula (M-8.2).

Furthermore, the compound represented by the general formula (M-8) used in the composition of the present invention is specifically represented by the formula (M-8.11) to the formula (M-8.14). A compound is preferable, and among them, a compound represented by the formula (M-8.12) is preferably included.

Furthermore, the compound represented by the general formula (M-8) used in the composition of the present invention is specifically represented by the formula (M-8.21) to the formula (M-8.24). A compound is preferable, and among them, a compound represented by the formula (M-8.22) is preferably contained.

Furthermore, the compound represented by the general formula (M-8) used in the composition of the present invention is specifically represented by the formula (M-8.31) to the formula (M-8.34). A compound is preferable, and among them, a compound represented by the formula (M-8.32) is preferably contained.

Furthermore, the compound represented by formula (M-8) used in the composition of the present invention is specifically represented by formula (M-8.41) to formula (M-8.44). A compound is preferable, and among them, a compound represented by the formula (M-8.42) is preferably included.

Furthermore, the compound represented by the general formula (M-8) used in the composition of the present invention is specifically represented by the formula (M-8.51) to the formula (M-8.54). A compound is preferable, and among them, a compound represented by the formula (M-8.52) is preferably included.

Furthermore, the compound represented by the general formula (M) may have the following partial structure in its structure.

(The black spot in the formula represents a carbon atom in the ring structure to which the partial structure is bonded.)
The compound having the partial structure is preferably a compound represented by general formulas (M-10) to (M-18).

The compound represented by the general formula (M-10) is as follows.

( ^Wherein , X ^M101 and X ^M102 each independently represent a fluorine atom or a hydrogen atom, Y ^M101 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M101 represents an alkyl group having 1 to 5 carbon atoms, Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and W ^M101 and W ^M102 each independently represent —CH ₂ — or —O—.
Further, the compound represented by formula (M-10) used in the composition of the present invention is specifically represented by formula (M-10.1) to formula (M-10.12). A compound is preferable, and among them, a compound represented by formula (M-10. 5) to formula (M-10.12) is preferably contained.

The compound represented by the general formula (M-11) is as follows.

( ^Wherein , X ^M111 to X ^M114 each independently represents a fluorine atom or a hydrogen atom, Y ^M111 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M111 represents an alkyl group having 1 to 5 carbon atoms, Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.)
When the compound represented by the general formula (M-11) represents a compound having a benzyl position, the effect of improving the stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Furthermore, the compound represented by the general formula (M-11) used in the composition of the present invention is specifically represented by the formula (M-11.1) to the formula (M-11.8). A compound is preferable, and among them, a compound represented by formula (M-11.1) to formula (M-11.4) is preferably contained.

The compound represented by the general formula (M-12) is as follows.

( ^Wherein , X ^M121 and X ^M122 each independently represent a fluorine atom or a hydrogen atom, Y ^M121 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M121 represents an alkyl group having 1 to 5 carbon atoms, Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and W ^M121 and W ^M122 each independently represent —CH ₂ — or —O—.
Furthermore, the compound represented by the general formula (M-12) used in the composition of the present invention is specifically represented by the formula (M-12.1) to the formula (M-12.12). A compound is preferable, and among them, a compound represented by formula (M-12.5) to formula (M-12.8) is preferably contained.

The compound represented by the general formula (M-13) is as follows.

( ^Wherein , X ^M131 to X ^M134 each independently represents a fluorine atom or a hydrogen atom, Y ^M131 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M131 represents an alkyl group having 1 to 5 carbon atoms, ^Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and W ^M131 and W ^M132 each independently represent —CH ₂ — or —O—.
Furthermore, the compound represented by the general formula (M-13) used in the composition of the present invention is specifically represented by the formula (M-13.1) to the formula (M-13.28). It is preferable that the compound is a compound, and among them, from the formulas (M-13.1) to (M-13.4), (M-13.11) to (M-13.14), (M-13.25) to ( It is preferable to contain a compound represented by M-13.28).

The compound represented by the general formula (M-14) is as follows.

( ^Wherein X ^M141 to X ^M144 each independently represents a fluorine atom or a hydrogen atom, Y ^M141 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M141 represents an alkyl group having 1 to 5 carbon atoms, ^Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and W ^M141 and W ^M142 each independently represent —CH ₂ — or —O—.
In the case where the compound represented by the general formula (M-14) represents a compound having a benzyl position, the effect of improving the stability is great by storing together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Furthermore, the compound represented by the general formula (M-14) used in the composition of the present invention is specifically represented by the formula (M-14.1) to the formula (M-14.8). A compound is preferable, and among them, a compound represented by formula (M-14.5) and formula (M-14.8) is preferably contained.

The compound represented by the general formula (M-15) is as follows.

( ^Wherein X ^M151 and X ^M152 each independently represent a fluorine atom or a hydrogen atom, Y ^M151 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M151 represents an alkyl group having 1 to 5 carbon atoms, Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and W ^M151 and W ^M152 each independently represent —CH ₂ — or —O—.
Furthermore, the compound represented by the general formula (M-15) used in the composition of the present invention is specifically represented by the formulas (M-15.1) to (M-15.14). Preferably, the compound contains a compound represented by formula (M-15.5) to formula (M-15.8) or formula (M-15.11) to formula (M-15.14). It is preferable to do.

The compound represented by the general formula (M-16) is as follows.

( ^Wherein X ^M161 to X ^M164 each independently represents a fluorine atom or a hydrogen atom, Y ^M161 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M161 represents an alkyl group having 1 to 5 carbon atoms, Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.)
Furthermore, the compound represented by the general formula (M-16) used in the composition of the present invention is specifically represented by the formula (M-16.1) to the formula (M-16.8). A compound is preferable, and among them, it is preferable to include a compound represented by Formula (M-16.1) to Formula (M-16.4).

The compound represented by the general formula (M-17) is as follows.

^(Wherein, ^X M171 ^~ X ^M174 are each independently a fluorine atom or a hydrogen ^{atom, Y M171} fluorine atom, a chlorine atom or -OCF ^{_3, R M171} is an alkyl group having 1 to 5 carbon atoms, ^Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and W ^M171 and W ^M172 each independently represent —CH ₂ — or —O—.
Further, the compound represented by the general formula (M-17) used in the composition of the present invention is specifically represented by the formula (M-17.1) to the formula (M-17.52). Preferably, the compound is a compound (M-17.9) to (M-17.12), (M-17.21) to (M-17.28), (M-17. 45) to a compound represented by the formula (M-17.48) is preferably contained.

The compound represented by the general formula (M-18) is as follows.

( ^Wherein X ^M181 to X ^M186 each independently represents a fluorine atom or a hydrogen atom, Y ^M181 represents a fluorine atom, a chlorine atom or —OCF ₃ , R ^M181 represents an alkyl group having 1 to 5 carbon atoms, Represents an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.)
Furthermore, the compound represented by the general formula (M-18) used in the composition of the present invention is specifically represented by the formula (M-18.1) to the formula (M-18.12). A compound is preferable, and among them, it is preferable to include a compound represented by Formula (M-18.5) to Formula (M-18.8).

As the compound represented by the general formula (J), a compound represented by the general formula (K) is preferable. These compounds correspond to dielectrically positive compounds (Δε is greater than 2).

(Wherein R ^K1 represents an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —CH═CH—, — Optionally substituted by C≡C—, —O—, —CO—, —COO— or —OCO—,
n ^K1 represents 0, 1, 2, 3 or 4;
A ^K1 and A ^K2 are each independently
(A) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - may be replaced by -O- or -S- And (b) a 1,4-phenylene group (one —CH═ present in this group or two or more non-adjacent —CH═ may be replaced by —N═).
A hydrogen atom on the group (a) and the group (b) may be independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^K1 and Z ^K2 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, —CF ₂ O—, Represents —COO—, —OCO— or —C≡C—,
When n ^K1 is 2, 3 or 4 and a plurality of A ^K2 are present, they may be the same or different, and n ^K1 is 2, 3 or 4 and a plurality of Z ^K1 is present If they are the same or different,
X ^K1 and X ^K3 each independently represent a hydrogen atom, a chlorine atom or a fluorine atom,
X ^K2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, or a 2,2,2-trifluoroethyl group. )
In general formula (K), R ^K1 represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, or alkenyloxy having 2 to 8 carbon atoms. A group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms is preferable. An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms is more preferable, an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms is more preferable, and an alkenyl group having 3 carbon atoms. (Propenyl group) is particularly preferred.

^RK1 is preferably an alkyl group when importance is placed on reliability, and an alkenyl group is preferred when importance is placed on lowering viscosity.

Further, when the ring structure to which it is bonded is a phenyl group (aromatic), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and carbon An alkenyl group having 4 to 5 atoms is preferable, and when the ring structure to which the alkenyl group is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a linear alkyl group having 1 to 5 carbon atoms, a straight chain A straight-chain alkoxy group having 1 to 4 carbon atoms and a straight-chain alkenyl group having 2 to 5 carbon atoms are preferred. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear. From the viewpoint of the effect of improving the stability by storing together with the additive, R ^K1 is preferably an alkenyl group or an alkenyloxy group.

A ^K1 and A ^K2 are preferably aromatic when it is required to independently increase Δn, and are preferably aliphatic for improving the response speed, and trans-1,4 -Cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group, 2, 3-difluoro-1,4-phenylene group, 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6- It preferably represents a diyl group, decahydronaphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably represents the following structure:

It is more preferable to represent the following structure.

Z ^K1 and ^{Z K2} are each _{independently} _{-CH 2 O -, - CF 2} O -, - CH 2 CH 2 -, - CF 2 CF 2 - or preferably a single bond, _-CF 2 O-, —CH ₂ CH ₂ — or a single bond is more preferable, and —CF ₂ O— or a single bond is particularly preferable.

n ^K1 is preferably 0, 1, 2 or 3, preferably 0, 1 or 2, preferably 0 or 1 when emphasizing the improvement of Δε, and preferably 1 or 2 when emphasizing Tni. .

The compound represented by the general formula (K) is preferably a compound selected from the group of compounds represented by the general formula (K-1), for example.

(Wherein R ^K11 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^K11 to X ^K14 are each independently hydrogen. represents an atom or a fluorine ^{atom, Y K11} represents a fluorine atom or OCF _3.)
Further, the compound represented by the general formula (K-1) is specifically preferably a compound represented by the formula (K-1.1) to the formula (K-1.4). A compound represented by formula (K-1.2) is preferred, and a compound represented by formula (K-1.2) is more preferred. It is also preferred to use the compounds represented by formula (K-1.1) or formula (K-1.2) at the same time.

The compound represented by General Formula (K) is preferably a compound selected from the group of compounds represented by General Formula (K-2), for example.

(Wherein R ^K21 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^K21 to X ^K24 are each independently hydrogen. represents an atom or a fluorine ^{atom, Y K21} represents a fluorine atom or OCF _3.)
Further, the compound represented by the general formula (K-2) is specifically preferably a compound represented by the formula (K-2.1) to the formula (K-2.6). A compound represented by formula (K-2.5) or formula (K-2.6) is preferred, and a compound represented by formula (K-2.6) is more preferred. It is also preferred to use the compounds represented by formula (K-2.5) or formula (K-2.6) at the same time.

The compound represented by General Formula (K) is preferably a compound selected from the group of compounds represented by General Formula (K-3), for example.

(Wherein R ^K31 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^K31 to X ^K36 are each independently hydrogen. Represents an atom or a fluorine atom, and Y ^K31 represents a fluorine atom or OCF _3. )
When a composition having a low viscosity and a high response speed is required, it is preferable to lower the lower limit value and lower the upper limit value. Furthermore, when the composition of the present invention keeps Tni high and a composition having good temperature stability is required, it is preferable to lower the lower limit and lower the upper limit. Further, when it is desired to increase the dielectric anisotropy in order to keep the driving voltage low, it is preferable to increase the upper limit value while increasing the lower limit value.

In the case where the compound represented by the general formula (K-3) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (K-3) is preferably a compound represented by the formula (K-3.1) to the formula (K-3.4). A compound represented by K-3.1) or formula (K-3.2) is more preferable. It is also preferred to use the compounds represented by formula (K-3.1) and formula (K-3.2) at the same time.

The compound represented by the general formula (K) is preferably, for example, a compound selected from the group of compounds represented by the general formula (K-4).

(Wherein R ^K41 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^K41 to X ^K46 are each independently hydrogen. An atom or a fluorine atom, Y ^K41 represents a fluorine atom or OCF ₃ , and Z ^K41 represents —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, or —CF ₂ O—.
Further, the compound represented by the general formula (K-4) is preferably a compound represented by the formula (K-4.1) to the formula (K-4.18). More preferred are compounds represented by (K-4.1), formula (K-4.2), formula (K-4.11), and (K-4.12). It is also preferred to use compounds represented by formula (K-4.1), formula (K-4.2), formula (K-4.11), and (K-4.12) at the same time.

The compound represented by the general formula (K) is preferably a compound selected from, for example, a compound group represented by the general formula (K-5).

(Wherein R ^K51 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^K51 to X ^K56 are each independently hydrogen. An atom or a fluorine atom, Y ^K51 represents a fluorine atom or OCF ₃ , and Z ^K51 represents —OCH ₂ —, —CH ₂ O—, —OCF ₂ —, or —CF ₂ O—.
When the compound represented by the general formula (K-5) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (K-5) is preferably a compound represented by the formula (K-5.1) to the formula (K-5.18). A compound represented by the formula (K-5.14) to the compound represented by the formula (K-5.14) is preferable, and a compound represented by the formula (K-5.12) is more preferable.

The compound represented by General Formula (K) is preferably a compound selected from the group of compounds represented by General Formula (K-6), for example.

( ^Wherein R ^K61 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and X ^K61 to X ^K68 are each independently hydrogen. represents an atom or a fluorine ^{atom, Y K61} represents a fluorine atom or OCF ^{_3, Z K61} is _{_{-OCH 2 -, - CH 2 O}} -, - OCF 2 - or an _-CF 2 O-).
In the case where the compound represented by the general formula (K-6) represents a compound having a benzyl position, the effect of improving the stability is great by storing together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (K-6) is preferably a compound represented by the formula (K-6.1) to the formula (K-6.18). Compounds represented by formula (K-6.18) to formula (K-6.18) are preferred, and compounds represented by formula (K-6.16) and formula (K-6.17) are more preferred.

<Third embodiment of the compound represented by the general formula (I)>
The compound represented by the general formula (I) is preferably a compound selected from the compounds represented by the following general formula (L). The compound corresponds to a dielectrically neutral compound (Δε value is −2 to 2).

(Wherein R ^L1 and R ^L2 are each independently an aldehyde group, amino group, carboxyl group, tosyl group, mesyl group, triflate group, hydroxy group, hydroxymethyl group, nitro group, sulfo group, cyano group, acid chloride) Group, a chlorine atom, a bromine atom, an iodine atom, or an alkyl group having 1 to 8 carbon atoms, and one or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —CH _2. ═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO— may be substituted,
n ^L1 represents 0, 1, 2 or 3,
A ^L1 , A ^L2 and A ^L3 each independently represent (a) a 1,4-cyclohexylene group (one —CH ₂ — present in the group or two or more —CH ₂ — not adjacent to each other). May be replaced by -O-.)
(B) a 1,4-phenylene group (one —CH═ present in the group or two or more non-adjacent —CH═ may be replaced by —N═) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, one —CH═ or two or more non-adjacent —CH═ may be replaced by —N═.
The group (a), the group (b) and the group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z ^L1 and Z ^L2 are each independently a single bond, —CH ₂ CH ₂ —, — (CH ₂ ) ₄ —, —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —OCF ₂ -, -CF ₂ O-, -CH = NN-CH-, -CH = CH-, -CF = CF- or -C≡C-
When n ^L1 is 2 or 3, and a plurality of A ^L2 are present, they may be the same or different, and when n ^L1 is 2 or 3, and a plurality of Z ^L2 are present, May be the same or different. )
When importance is attached to reliability, R ^L1 and R ^L2 are preferably both alkyl groups, and when importance is placed on reducing the volatility of the compound, it is preferably an alkoxy group, and importance is placed on viscosity reduction. In this case, at least one is preferably an alkenyl group.

The number of halogen atoms present in the molecule is preferably 0, 1, 2 or 3, preferably 0 or 1, and 1 is preferred when importance is attached to compatibility with other liquid crystal molecules.

R ^L1 and R ^L2 are each a linear alkyl group having 1 to 5 carbon atoms or a linear alkyl group having 1 to 4 carbon atoms when the ring structure to which R ^L1 is bonded is a phenyl group (aromatic). When the ring structure to which it is bonded is a saturated ring structure such as cyclohexane, pyran and dioxane, a straight-chain C 1-5 carbon atom is preferred. Alkyl groups, linear alkoxy groups having 1 to 4 carbon atoms and linear alkenyl groups having 2 to 5 carbon atoms are preferred. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms, if present, is preferably 5 or less, and is preferably linear. From the viewpoint of the effect of improving the stability by storing together with the additive, any one or more of R ^L1 and R ^L2 are preferably an alkenyl group or an alkenyloxy group.

n ^L1 is preferably 0 when importance is attached to the response speed, 2 or 3 is preferred for improving the upper limit temperature of the nematic phase, and 1 is preferred for balancing these. In order to satisfy the properties required for the composition, it is preferable to combine compounds having different values.

A ^L1 , A ^L2, and A ^L3 are preferably aromatic when it is required to increase Δn, and are preferably aliphatic for improving the response speed, and are each independently trans- 1,4-cyclohexylene group, 1,4-phenylene group, 2-fluoro-1,4-phenylene group, 3-fluoro-1,4-phenylene group, 3,5-difluoro-1,4-phenylene group 1,4-cyclohexenylene group, 1,4-bicyclo [2.2.2] octylene group, piperidine-1,4-diyl group, naphthalene-2,6-diyl group, decahydronaphthalene-2,6 -It preferably represents a diyl group or a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, and more preferably represents the following structure:

More preferably, it represents a trans-1,4-cyclohexylene group or a 1,4-phenylene group.

Z ^L1 and Z ^L2 are preferably single bonds when the response speed is important.

The compound represented by the general formula (L) preferably has 0 or 1 halogen atom in the molecule.

The compound represented by the general formula (L) is preferably a compound selected from the group of compounds represented by the general formulas (L-1) to (L-8).

The compound represented by the general formula (L-1) is the following compound.

(In the formula, R ^L11 and R ^L12 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)
R ^L11 and R ^L12 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. . From the viewpoint of the effect of improving the stability by storing together with the additive, any one or more of R ^L11 and R ^L12 are preferably an alkenyl group or an alkenyloxy group.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-1).

(Wherein R ^L12 represents the same meaning as in general formula (L-1).)
The compound represented by the general formula (L-1-1) is a compound selected from the group of compounds represented by the formula (L-1-1.1) to the formula (L-1-1.3). And is preferably a compound represented by formula (L-1-1.2) or formula (L-1-1.3), and particularly represented by formula (L-1-1.3). It is preferable that it is a compound.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-2).

(Wherein R ^L12 represents the same meaning as in general formula (L-1).)
Further, the compound represented by the general formula (L-1-2) is a compound selected from the group of compounds represented by the formula (L-1-2.1) to the formula (L-1-2.4). Preferably, it is a compound represented by the formula (L-1-2.2) to the formula (L-1-2.4). In particular, the compound represented by the formula (L-1-2.2) is preferable because the response speed of the composition of the present invention is particularly improved. When obtaining Tni higher than the response speed, it is preferable to use a compound represented by the formula (L-1-2.3) or the formula (L-1-2.4). The content of the compounds represented by formula (L-1-2.3) and formula (L-1-2.4) is not preferably 30% or more in order to improve the solubility at low temperatures.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-3).

(Wherein R ^L13 and R ^L14 each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
R ^L13 and R ^L14 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. .

Further, the compound represented by the general formula (L-1-3) is a compound selected from the group of compounds represented by the formula (L-1-3.1) to the formula (L-1-3.12). Preferably, it is a compound represented by formula (L-1-3.1), formula (L-1-3.3) or formula (L-1-3.4). In particular, the compound represented by the formula (L-1-3.1) is preferable because the response speed of the composition of the present invention is particularly improved. Further, when obtaining Tni higher than the response speed, the equation (L-1-3.3), the equation (L-1-3.4), the equation (L-1-3.11), and the equation (L− It is preferable to use a compound represented by 1-3.12).

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-4) and / or (L-1-5).

(In the formula, R ^L15 and R ^L16 each independently represent an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms.)
R ^L15 and R ^L16 are preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. .

Furthermore, the compounds represented by the general formulas (L-1-4) and (L-1-5) are represented by the formulas (L-1-4.1) to (L-1-5.3). And a compound represented by the formula (L-1-4.2) or the formula (L-1-5.2) is preferable.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-6).

(In the formula, R ^L17 and R ^L18 each independently represent a methyl group or a hydrogen atom.)
Further, the compound represented by the general formula (L-1-6) is a compound selected from the compound group represented by the formula (L-1-6.1) to the formula (L-1-6.3). Preferably there is.

The compound represented by the general formula (L-2) is the following compound.

(In the formula, R ^L21 and R ^L22 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)
R ^L21 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ^L22 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or a carbon atom. An alkoxy group of 1 to 4 is preferable.

Further, the compound represented by the general formula (L-2) is preferably a compound selected from the group of compounds represented by the formulas (L-2.1) to (L-2.6). A compound represented by formula (L-2.1), formula (L-2.3), formula (L-2.4) and formula (L-2.6) is preferred.

The compound represented by the general formula (L-3) is the following compound.

(In the formula, R ^L31 and R ^L32 each independently represent the same meaning as R ^L1 and R ^L2 in General Formula (L).)
R ^L31 and R ^L32 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

When the compound represented by the general formula (L-3) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (L-3) is preferably a compound selected from the group of compounds represented by the formulas (L-3.1) to (L-3.4). A compound represented by the formula (L-3.7) from (L-3.2) is preferable.

The compound represented by the general formula (L-4) is the following compound.

(In the formula, R ^L41 and R ^L42 each independently represent the same meaning as R ^L1 and R ^L2 in General Formula (L).)
R ^L41 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ^L42 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or a carbon atom. An alkoxy group of 1 to 4 is preferable. )
The compound represented by the general formula (L-4) can be used alone, or two or more compounds can be used in combination. There are no particular restrictions on the types of compounds that can be combined, but they are used in appropriate combinations according to the required properties such as solubility at low temperatures, transition temperatures, electrical reliability, and birefringence. The kind of the compound used is, for example, one kind as one embodiment of the present invention, two kinds, three kinds, four kinds, and five kinds or more.

Since the compound represented by the general formula (L-4) tends to exhibit liquid crystallinity near room temperature and tends to be deteriorated and deteriorated, storage with an additive for preventing deterioration can improve stability. Great effect.

In addition, when the compound represented by the general formula (N-1-4) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive that prevents alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed. The compound represented by general formula (L-4) is preferably a compound represented by formula (L-4.1) to formula (L-4.3), for example.

The compound represented by the general formula (L-4) is preferably, for example, a compound represented by the formula (L-4.4) to the formula (L-4.6). It is preferable that it is a compound represented by this.

The compound represented by the general formula (L-4) is preferably a compound represented by the formula (L-4.7) to the formula (L-4.10), and particularly the formula (L-4. The compound represented by 9) is preferred.

The compound represented by the general formula (L-5) is the following compound.

(In the formula, R ^L51 and R ^L52 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L).)
R ^L51 is preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and R ^L52 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms, or a carbon atom. An alkoxy group of 1 to 4 is preferable.

In the case where the compound represented by the general formula (L-5) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or (L-5.2), and in particular, the compound represented by the formula (L-5. It is preferable that it is a compound represented by 1).

The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4).

The compound represented by the general formula (L-5) is preferably a compound selected from the group of compounds represented by the formulas (L-5.5) to (L-5.7). The compound represented by L-5.7) is preferred.

The compound represented by the general formula (L-6) is the following compound.

(In the formula, R ^L61 and R ^L62 each independently represent the same meaning as R ^L1 and R ^L2 in the general formula (L), and X ^L61 and X ^L62 each independently represent a hydrogen atom or a fluorine atom. )
R ^L61 and R ^L62 are each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and one of X ^L61 and X ^L62 is a fluorine atom and the other is a hydrogen atom. Is preferred.

In the case where the compound represented by the general formula (L-6) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

The compound represented by the general formula (L-6) is preferably a compound represented by the formula (L-6.1) to the formula (L-6.9).

Further, the compound represented by the general formula (L-6) is preferably, for example, a compound represented by the formula (L-6.10) to the formula (L-6.17). A compound represented by L-6.11) is preferable.

The compound represented by the general formula (L-7) is the following compound.

^{(Wherein, R L71} and ^{R L72} each independently represent the same meaning as ^{R L1} and ^{R L2} in Formula ^{(L), A L71} and ^{A L72} is ^{A L2} and in the general formula (L) independently A ^L3 represents the same meaning, but the hydrogen atoms on A ^L71 and A ^L72 may be each independently substituted with a fluorine atom, Z ^L71 represents the same meaning as Z ^L2 in formula (L), X ^L71 and X ^L72 each independently represent a fluorine atom or a hydrogen atom.)
In the formula, R ^L71 and R ^L72 are each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and A ^L71 and A ^L72 Are each independently preferably a 1,4-cyclohexylene group or a 1,4-phenylene group, the hydrogen atoms on A ^L71 and A ^L72 may be each independently substituted with a fluorine atom, and Z ^L71 is a single group. A bond or COO- is preferable, a single bond is preferable, and X ^L71 and X ^L72 are preferably a hydrogen atom.

When the compound represented by the general formula (L-7) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive that prevents alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.1) to the formula (L-7.4), and the formula (L-7. It is preferable that it is a compound represented by 2).

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.11) to the formula (L-7.13). It is preferable that it is a compound represented by 11).

Furthermore, the compound represented by the general formula (L-7) is a compound represented by the formula (L-7.21) to the formula (L-7.23). A compound represented by formula (L-7.21) is preferable.

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.31) to the formula (L-7.34), and the formula (L-7. 31) or / and a compound represented by the formula (L-7.32).

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.41) to the formula (L-7.44), and the formula (L-7. 41) or / and a compound represented by formula (L-7.42).

Furthermore, the compound represented by the general formula (L-7) is preferably a compound represented by the formula (L-7.51) to the formula (L-7.53).

The compound represented by the general formula (L-8) is the following compound.

(In the formula, R ^L81 and R ^L82 each independently represent the same meaning as R ^L1 and R ^L2 in General Formula (L), and A ^L81 represents the same meaning or single bond as A ^L1 in General Formula (L)). However, each hydrogen atom on A ^L81 may be independently substituted with a fluorine atom, and X ^L81 to X ^L86 each independently represent a fluorine atom or a hydrogen atom.)
^{Wherein, R L81} and ^{R L82} are each independently an alkyl group having 1 to 5 carbon atoms, an alkenyl group or an alkoxy group having 1 to 4 carbon atoms of 2 to 5 carbon atoms ^{preferably, A L81} is 1, A 4-cyclohexylene group or a 1,4-phenylene group is preferable, and the hydrogen atoms on A ^L71 and A ^L72 may each independently be substituted with a fluorine atom, and the same in the general formula (L-8) The number of fluorine atoms in the ring structure is preferably 0 or 1, and the number of fluorine atoms in the molecule is preferably 0 or 1.

When the compound represented by the general formula (L-8) represents a compound having a benzyl position, the effect of improving stability is great by storing it together with an additive for preventing alteration. By storing together with additives, highly reactive alteration of the benzyl position can be suppressed.

Further, the compound represented by the general formula (L-8) is preferably a compound represented by the formula (L-8.1) to the formula (L-8.4), and the formula (L-8. 3), formula (L-8.5), formula (L-8.6), formula (L-8.13), formula (L-8.16) to formula (L-8.18), formula (L) A compound represented by formula (L-8.28) to L-8.23) is more preferable.

When the compound of the present invention has an alkenyl group as a side chain, when the alkenyl group is bonded to cyclohexane, the alkenyl group preferably has 2 to 5 carbon atoms, and the alkenyl group is bonded to benzene. In this case, the alkenyl group preferably has 4 to 5 carbon atoms, and the unsaturated bond of the alkenyl group and benzene are preferably not directly bonded.

The liquid crystal compound is preferably a compound represented by the general formula (P).

(In the general formula (P), Z ^p1 represents a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms in which a hydrogen atom may be substituted with a halogen atom, and a hydrogen atom in a halogen atom. An optionally substituted alkoxy group having 1 to 15 carbon atoms, a hydrogen atom optionally substituted with a halogen atom, and an alkenyl group having 1 to 15 carbon atoms optionally substituted with a halogen atom Represents an alkenyloxy group having 1 to 15 carbon atoms or —Sp ^p2 —R ^p2 ;
R ^p1 and R ^p2 are each independently the following formulas (RI) to (R-IX):

In the formulas (RI) to (R-IX), R ² to R ⁶ are independently of each other a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or the number of carbon atoms. 1 to 5 halogenated alkyl groups, W is a single bond, —O— or a methylene group, T is a single bond or —COO—, and p, t and q are each independently 0, Represents 1 or 2,
Sp ^p1 and Sp ^p2 represent spacer groups,
L ^p1 and L ^p2 are each independently a single bond, —O—, —S—, —CH ₂ —, —OCH ₂ —, —CH ₂ O—, —CO—, —C ₂ H ₄ —, — COO—, —OCO—, —OCOOCH ₂ —, —CH ₂ OCOO—, —OCH ₂ CH ₂ O—, —CO—NR ^a —, —NR ^a —CO—, —SCH ₂ —, —CH ₂ S— ^{^{^{, -CH = CR a -COO -,}}} - CH = CR a -OCO -, - COO-CR a = CH -, - OCO-CR a = CH -, - COO-CR a = CH-COO -, - COO ^{^{-CR a = CH-OCO -,}} - OCO-CR a = CH-COO -, - OCO-CR a = CH-OCO -, - (CH 2) z -C (= O) -O -, - (CH ₂ ) z—O— (C═O) —, —O— (C═O) — (CH ₂ ) z—, — (C═O) —O — (CH ₂ ) z—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF ₂ —, —CF ₂ O—, —OCF ₂ —, —CF ₂ CH ₂ —, —CH ₂ CF ₂ —, —CF ₂ CF ₂ — or —C≡C— (wherein each R ^a independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, In the above formula, z represents an integer of 1 to 4.
M ^p2 represents 1,4-phenylene group, 1,4-cyclohexylene group, anthracene-2,6-diyl group, phenanthrene-2,7-diyl group, pyridine-2,5-diyl group, pyrimidine-2, 5-diyl group, naphthalene-2,6-diyl group, indan-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5 -Represents a diyl group, but M ^p2 is unsubstituted or an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a carbon atom ^May be substituted with a halogenated alkoxy group of formula 1 to 12, a halogen atom, a cyano group, a nitro group or —R ^p1 ;
M ^p1 represents the following formulas (i-11) to (ix-11):

(In the formula, it binds to Sp ^p1 with ★ and binds to L ^p1 or L ^p2 with ★★),
M ^p3 represents the following formulas (i-13) to (ix-13):

(In the formula, it binds to Z ^p1 with ★ and binds to L ^p2 with ★★),
m ^p2 to m ^p4 each independently represents 0, 1, 2 or 3, m ^p1 and m ^p5 each independently represent 1, 2 or 3, but when there are a plurality of Z ^p1 May be the same or different. When a plurality of R ^p1 are present, they may be the same or different. When a plurality of R ^p2 are present, they may be the same. They may be different, they may be the same or different when multiple Sp ^p1 are present, and they may be the same or different when multiple Sp ^p2 are present, When a plurality of L ^p1 are present, they may be the same or different, and when a plurality of M ^p2 are present, they may be the same or different. )
Since the compound represented by the general formula (P) has a polymerizable group and easily deteriorates and deteriorates, the effect of improving stability by storing together with an additive for preventing the deterioration of the liquid crystal compound is great.

In the general formula (P) according to the present invention, Z ^p1 is preferably -Sp ^p2 -R ^p2 , and R ¹¹ and R ¹² are each independently represented by the formulas (R-1) to (R-3). Either is preferable.

In the general formula (P), m ^p1 + m ^p5 is preferably 2 or more.

In the general formula (P), L ^p1 represents a single bond, —OCH ₂ —, —CH ₂ O—, —CO—, —C ₂ H ₄ —, —COO—, —OCO—, —COOC _2. _{_{H 4 -, - OCOC 2 H}} 4 -, - C 2 H 4 OCO -, - C 2 H 4 COO -, - CH = CH -, - CF 2 -, - CF 2 O -, - (CH 2) z —C (═O) —O—, — (CH ₂ ) z—O— (C═O) —, —O— (C═O) — (CH ₂ ) z—, —CH═CH—COO—, —COO—CH═CH—, —OCOCH═CH—, — (C═O) —O— (CH ₂ ) z—, —OCF ₂ — or —C≡C—, and L ^p2 represents —OCH ₂ _{_{_{_{CH 2 O -, - COOC 2}}}} H 4 -, - OCOC 2 H 4 -, - (CH 2) z -C (= O) -O -, - (CH 2) z-O- (C = O) - _{_{-O- (C = O) - (}} CH 2) z -, - (C = O) -O- (CH 2) z -, - CH = CH-COO -, - COO-CH = CH -, - OCOCH ═CH—, —C ₂ H ₄ OCO— or —C ₂ H ₄ COO—, and z in the above formula is preferably an integer of 1 to 4.

In addition, at least one of L ^p1 and L ^{p2 in} the general formula (1) is — (CH ₂ ) _z —C (═O) —O— or — (CH ₂ ) z—O— (C═O). It is preferably at least one selected from the group consisting of — and —O— (C═O) — (CH ₂ ) z— and — (C═O) —O— (CH ₂ ) z—.

In the general formula (P), R ^p1 and R ^p2 are each independently the following formulas (R-1) to (R-15):

Any of these is more preferable.

In the general formula (P), m ^p3 represents 0, 1, 2, or 3. When m ^p2 is 1, L ^p1 is a single bond, and when m ^p2 is 2 or 3, a plurality of L ^p1 is present. At least one is preferably a single bond.

In the general formula (P), m ^p3 represents 0, 1, 2 or 3, and when m ^p3 is 1, M ^p2 is a 1,4-phenylene group, and when m ^p3 is 2 or 3, a plurality of them are present. ^{M p2} adjacent to ^{M p1} through at least ^{L p1} of ^{M p2} which is preferably a 1,4-phenylene group.

Further, m ^{p3 in the} general formula (P) represents 0, 1, 2, or 3, and at least one of M ^p2 is a 1,4-phenylene group substituted with one or two or more fluorines. It is preferable.

Further, m ^{p4 in the} general formula (P) represents 0, 1, 2 or 3, and at least one of M ^p3 is a 1,4-phenylene group substituted with one or two or more fluorines. It is preferable.

The spacer group (Sp ^p1 , Sp ^p2 , Sp ^p4 ) in the general formula (P) is a single bond, —OCH ₂ —, — (CH ₂ ) _z O—, —CO—, —C ₂ H _4. _{_{-, - COO -, - OCO}} -, - COOC 2 H 4 -, - OCOC 2 H 4 -, - (CH 2) z -, - C 2 H 4 OCO -, - C 2 H 4 COO -, - CH ═CH—, —CF ₂ —, —CF ₂ O—, — (CH ₂ ) _z —C (═O) —O—, — (CH ₂ ) _z —O— (C═O) —, —O— (C═O) — (CH ₂ ) _z —, — (C═O) —O— (CH ₂ ) _z —, —O— (CH ₂ ) _z —O—, —OCF ₂ —, —CH═CH —COO—, —COO—CH═CH—, —OCOCH═CH— or —C≡C— is preferable, and Z is an integer of 1 to 10. Rukoto is preferable.

The polymerizable compound of the general formula (P) according to the present invention is represented by the general formula (Pa), the general formula (Pb), the general formula (Pc), and the general formula (Pd). A compound selected from the group consisting of compounds is preferred.

In the general formulas (Pa) to (Pd), R ^p1 and R ^p2 are each independently the following formulas (RI) to (R-IX):

In the formulas (RI) to (R-IX), R ² to R ⁶ are independently of each other a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or the number of carbon atoms. 1 to 5 halogenated alkyl groups, W is a single bond, —O— or a methylene group, T is a single bond or —COO—, and p, t and q are each independently 0, Represents 1 or 2,
Ring A and Ring B are each independently 1,4-phenylene group, 1,4-cyclohexylene group, anthracene-2,6-diyl group, phenanthrene-2,7-diyl group, pyridine-2,5- Diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, indan-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or 1, Represents a 3-dioxane-2,5-diyl group, which is unsubstituted or an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy having 1 to 12 carbon atoms Group, a halogenated alkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or —R ^p1 is preferred,
Ring C represents the following formulas (ci) to (c-ix):

(In the formula, it binds to Sp ^p1 with ★ and binds to L ^p5 or L ^p6 with ★★),
Sp ^p1 and Sp ^p4 each represent a spacer group, and X ^p1 to X ^p4 preferably each independently represent a hydrogen atom or a halogen atom,
L ^p4 , L ^p5 and L ^p6 are each independently a single bond, —OCH ₂ —, —CH ₂ O—, —CO—, —C ₂ H ₄ —, —COO—, —OCO—, —COOC ₂ _{_{H 4 -, - OCOC 2 H}} 4 -, - C 2 H 4 OCO -, - C 2 H 4 COO -, - CH = CH -, - CF 2 -, - CF 2 O -, - (CH 2) z —C (═O) —O—, — (CH ₂ ) _z —O— (C═O) —, —O— (C═O) — (CH ₂ ) _z —, — (C═O) —O — (CH ₂ ) _z —, —O— (CH ₂ ) _z —O—, —OCF ₂ —, —CH═CHCOO—, —COOCH═CH—, —OCOCH═CH— or —C≡C—. It is preferable that z in the above formula is an integer of 1 to 4.

L ^p3 is preferably —CH═CHCOO—, —COOCH═CH— or —OCOCH═CH—.

In the compound represented by the general formula ( ^Pa ), it is preferable that m ^p6 and m ^p7 each independently represent 0, 1, 2, or 3. Further, it is more preferable that m ^p6 + m ^p7 = ^2-5 .

In the compound represented by the general formula ( ^Pb ), it is preferable that m ^p8 and m ^p9 each independently represent 1, 2 or 3. Further, it is more preferable that m ^p6 + m ^p7 = 2 to 3.

In the compound represented by the general formula (Pc), it is preferable that m ^p10 and m ^p11 each independently represent 0 or 1. Further, it is more preferable that m ^p10 + m ^p11 = 0-1. Further, since the general formula (Pc) has a phenanthrene ring, it is considered that the overall photosensitive action of the composition is large.

In the compound represented by the general formula (Pd), ^mp12 and ^mp15 each independently represent 1, 2, or 3, and ^mp13 preferably represents 0, 1, 2, or 3, m ^p14 preferably represents 0 or 1. Further, it is more preferable that m ^p12 + m ^p15 = 2 to 5. When a plurality of R ^p1 are present, they may be the same or different. When a plurality of R ^p1 are present, they may be the same or different, and a plurality of R ^p2 are present. In some cases, they may be the same or different. When a plurality of Sp ^p1 are present, they may be the same or different. When there are a plurality of Sp ^p4 , they are the same. They may be the same or different when there are a plurality of L ^p4 and L ^p5, and they may be the same when there are a plurality of rings A to C Or different.

Examples of preferred structures of the compounds represented by the general formulas (Pa) to (Pd) according to the present invention are shown below.

Preferred examples of the compound represented by the general formula (Pa) according to the present invention include polymerizable compounds represented by the following formulas (Pa-1) to (Pa-31).

Preferred examples of the compound represented by the general formula (Pb) according to the present invention include polymerizable compounds represented by the following formulas (Pb-1) to (Pb-34).

Preferred examples of the compound represented by the general formula (Pc) according to the present invention include polymerizable compounds represented by the following formulas (Pc-1) to (Pc-52).

The compound represented by the general formula (Pd) according to the present invention is preferably a compound represented by the following general formula (P-d ').

(In the compound represented by the general formula (Pd ′), ^mp10 is more preferably 2 or 3. The other symbols are the same as those in the general formula (pd) and are omitted.)
Preferable examples of the compound represented by the general formula (Pd) according to the present invention include polymerizable compounds represented by the following formulas (Pd-1) to (Pd-31).

The “alkyl group having 1 to 15 carbon atoms” according to the present invention is preferably a linear or branched alkyl group, and more preferably a linear alkyl group. In the general formula (1), R ¹ and R ² are each independently an alkyl group having 1 to 15 carbon atoms, and R ¹ and R ² are each independently 1 to 1 carbon atoms. Eight alkyl groups are preferred, and alkyl groups having 1 to 6 carbon atoms are more preferred.

Examples of the “alkyl group having 1 to 15 carbon atoms” according to the present invention include methyl group, ethyl group, propyl group, butyl group, isopropyl group, isobutyl group, t-butyl group, 3-pentyl group, isopentyl group. Group, neopentyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, pentadecyl group and the like. In the present specification, examples of alkyl groups are common and are appropriately selected from the above examples depending on the number of carbon atoms of each alkyl group.

Examples of the “alkoxy group having 1 to 15 carbon atoms” according to the present invention are preferably present at a position where at least one oxygen atom in the substituent is directly bonded to the ring structure. Group, propoxy group (n-propoxy group, i-propoxy group), butoxy group, pentyloxy group, octyloxy group and decyloxy group are more preferable. In addition, in this specification, the example of an alkoxy group is common and is suitably selected from the said illustration according to the number of carbon atoms of each alkoxy group.

Examples of the “alkenyl group having 2 to 15 carbon atoms” according to the present invention are vinyl group, allyl group, 1-propenyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl. Group, 2-pentenyl group, 3-pentenyl group, 2-hexenyl group and the like. More preferable alkenyl groups according to the present invention include the following formula (i) (vinyl group), formula (ii) (1-propenyl group), formula (iii) (3-butenyl group) and formula (iv) ) (3-pentenyl group):

(In the above formulas (i) to (iv), * represents a binding site to the ring structure.)
It is represented by
<Additive for preventing deterioration of liquid crystal compound>
One or more additives for preventing deterioration of the liquid crystal compound are added to the liquid crystal compound. Examples of the additive include an antioxidant, an ultraviolet absorber, a light stabilizer, a metal deactivator, and an oxygen scavenger.
The antioxidant is preferably a hindered phenol compound. As a hindered phenol compound, the general formula (H)

Wherein H ^y is a hydrocarbon having 1 to 25 carbon atoms (one or more —CH ₂ — in the hydrocarbon is —O—, —CO— , -COO-, or -OCO- may be substituted.), Represents a 1,4-phenylene group or a trans-1,4-cyclohexylene group, and the 1,4-phenylene group has an arbitrary hydrogen atom as fluorine. H ^y may be substituted by an atom, and H ^y is an alkylene group having 1 to 15 carbon atoms (one or more of —CH ₂ — in the alkylene group may be —O -, -CO-, -COO-, and -OCO- may be substituted.), -OCH _2- , -CH ₂ O-, -COO-, -OCO-, -CF ₂ O-, -OCF _{_{_{2 -, - CF 2 CF 2}}} -, - CH = CH-COO -, - CH = CH- CO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —C≡C—, single bond, 1,4-phenylene group, trans-1,4-cyclohexylene group In the 1,4-phenylene group, any hydrogen atom may be replaced by a fluorine atom, and l represents an integer of 2 to 6.)
It is preferable to contain 1 type, or 2 or more types of compounds represented by these.

H ^y is a hydrocarbon having 1 to 25 carbon atoms (one or more —CH ₂ — in the hydrocarbon is —O—, —CO—, —COO— so that oxygen atoms are not directly adjacent to each other). , Optionally substituted with -OCO-). X ^y represents an alkylene group having 2 to 15 carbon atoms (one or more of —CH ₂ — in the alkylene group is —O—, —CO—, —COO— so that the oxygen atom is not directly adjacent). , -OCO- may be substituted), a single bond, a 1,4-phenylene group, or a trans-1,4-cyclohexylene group is preferable. l is preferably from 2 to 4, particularly preferably 2.

As the antioxidant represented by the general formula (H), the following general formula (HI)

(Wherein M ^x is a hydrocarbon having 1 to 25 carbon atoms (one or two or more —CH ₂ — in the hydrocarbon is —O—, —CO— X represents an alkylene group having 1 to 15 carbon atoms (one or more of —CH ₂ — in the alkylene group represents oxygen, and —COO— may be substituted with —OCO—). It may be substituted with —O—, —CO—, —COO—, —OCO— so that the atoms are not directly adjacent to each other.), —OCH ₂ —, —CH ₂ O—, —COO—, —OCO —, —CF ₂ O—, —OCF ₂ —, —CF ₂ CF ₂ —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH -, -CH = CH-, -C≡C-, single bond, 1,4-phenylene group, trans-1,4-cycl Represents a hexylene group, and a 1,4-phenylene group in which any hydrogen atom may be replaced by a fluorine atom, a, b, c and d each independently represents 0 or 1, but a + b + c + d is 2 or more Is more preferable.

M ^x is a hydrocarbon having 2 to 15 carbon atoms (one or more —CH ₂ — in the hydrocarbon is —O—, —CO—, —COO— so that oxygen atoms are not directly adjacent to each other). X may be an alkylene group having 2 to 15 carbon atoms (one or more of —CH ₂ — in the alkylene group is directly adjacent to an oxygen atom) May be substituted with —O—, —CO—, —COO—, —OCO—), preferably a single bond, 1,4-phenylene group, or trans-1,4-cyclohexylene group. , A + b + c + d is more preferably 2 to 4, and 2 is particularly preferable.

More specifically, the general formula (H-II)

(Wherein M is an alkylene group having 1 to 15 carbon atoms (one or more —CH ₂ — in the alkylene group is —O—, —CO—, It may be substituted with —COO— or —OCO—.), —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —CF ₂ O—, —OCF ₂ —, —CF ₂ CF ₂ —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —C≡C—, single bond 1,4-phenylene group, trans-1,4-cyclohexylene group, and the 1,4-phenylene group is a hindered phenol derivative in which any hydrogen atom may be substituted by a fluorine atom. Preferably there is.

M in the general formula (II) is more preferably an alkylene group having 1 to 15 carbon atoms. A larger number is preferable in consideration of volatility, and a smaller number of carbons is preferable in consideration of viscosity. . From the above, M in the general formula (II) has more preferably 2 to 15 carbon atoms, and particularly preferably 2 to 10 carbon atoms.

Specifically, the compound represented by the general formula (H) is preferably represented by the general formula (H-1) to the general formula (H-4).

In general formulas (H-1) to (H-4), R ^H1 represents an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or It represents an alkenyloxy group having 2 to 10 carbon atoms, one -CH ₂ present in the radical - or non-adjacent two or more -CH ₂ - are each independently -O- or -S- In addition, one or two or more hydrogen atoms present in the group may be each independently substituted with a fluorine atom or a chlorine atom. More specifically, it is an alkyl group having 2 to 7 carbon atoms, an alkoxyl group having 2 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms. An alkyl group having 3 to 7 carbon atoms or an alkenyl group having 2 to 7 carbon atoms is more preferable.
In the general formula ^{(H4), M H4} is -CH ₂ 1, two or more of the alkylene group (the alkylene group having from 1 to 15 carbon atoms - as the oxygen atoms are not directly adjacent, - O—, —CO—, —COO—, —OCO— may be substituted.), —OCH ₂ —, —CH ₂ O—, —COO—, —OCO—, —CF ₂ O—, — OCF ₂ —, —CF ₂ CF ₂ —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, — C≡C—, a single bond, a 1,4-phenylene group (any hydrogen atom in the 1,4-phenylene group may be substituted with a fluorine atom) or a trans-1,4-cyclohexylene group. Preferably an alkylene group having 1 to 14 carbon atoms, In consideration of the viscosity, a large number of carbon atoms is preferable, but in consideration of the viscosity, the number of carbon atoms is preferably not too large. Therefore, the number of carbon atoms is more preferably 2 to 12, more preferably 3 to 10. 4 to 10 carbon atoms are more preferred, 5 to 10 carbon atoms are more preferred, and 6 to 10 carbon atoms are more preferred.
In general formulas (H-1) to (H-4), one or more non-adjacent —CH═ in the 1,4-phenylene group may be substituted by —N═. In addition, each hydrogen atom in the 1,4-phenylene group may be independently substituted with a fluorine atom or a chlorine atom.
In general formula (H-1) to general formula (H-4), one or more non-adjacent —CH ₂ — in the 1,4-cyclohexylene group is replaced by —O— or —S—. May be. In addition, each hydrogen atom in the 1,4-cyclohexylene group may be independently substituted with a fluorine atom or a chlorine atom.
More specifically, for example, the formulas (H-11) to (H-15) can be given.

Further, the antioxidant is preferably a hindered amine compound. As the hindered amine-based compound, it is preferable to contain a compound represented by the following general formula (i) or general formula (ii) in the molecule.

(Wherein R ⁱ⁰ represents a hydrogen atom, a hydroxyl group, —O., Or an alkyl group having 1 to 20 carbon atoms, and one or two or more non-adjacent —CH ₂ present in the alkyl group) Each independently represents —O—, —S—, —CO—, —CO—O—, —O—CO—, —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— , —C≡C—, —Si (CH ₃ ) ₂ —, a trans 1,4-cyclohexylene group, a 1,4-phenylene group or a naphthalene-2,6-diyl group, and R ⁱ⁰ 1 or 2 or more hydrogen atoms may be independently substituted with a fluorine atom, a chlorine atom or a cyano group. Ku,
R ⁱ¹ , R ⁱ² , R ⁱ³ and R ⁱ⁴ each independently represents an alkyl group having 1 to 12 carbon atoms, and R ⁱ¹ and R ⁱ² and / or R ⁱ³ and R ⁱ⁴ are bonded to each other to form a ring. You may,
^{^R ^i5,} R i6, R ⁱ⁷ and ^{R i8} are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon ^atoms, when ^{R II5} and ^{R II6} and / or ^{the R II7} and ^{R II8} represents an alkyl group , wherein ^{R II5} and ^{R II6} and / or ^{R II7} and ^{R II8} may be bonded to each other to form a ring,
n ⁱ represents 0 or 1,
m ⁱ represents an integer of 1-6, ^{M i} represents 1 to hexavalent organic group, the valence of ^{M i} is the same number as the number represented by ^{^{^{m i, R i0, R i1}}} , R i2, When there are a plurality of R ⁱ³ , R ⁱ⁴ , R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁸ and n ⁱ , they may be the same or different. )

(Wherein R ⁱⁱ⁰ represents a hydrogen atom, a hydroxyl group, —O ·, or an alkyl group having 1 to 20 carbon atoms, and one or two or more non-adjacent —CH ₂ present in the alkyl group) Each independently represents —O—, —S—, —CO—, —CO—O—, —O—CO—, —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— , —C≡C—, —Si (CH ₃ ) ₂ —, a trans 1,4-cyclohexylene group, a 1,4-phenylene group or a naphthalene-2,6-diyl group may be substituted in R ⁱⁱ⁰ 1 or 2 or more hydrogen atoms are each independently substituted with a fluorine atom, a chlorine atom or a cyano group It may be,
R ⁱⁱ¹ , R ⁱⁱ² , R ⁱⁱ³ and R ⁱⁱ⁴ each independently represent an alkyl group having 1 to 12 carbon atoms, and R ⁱⁱ¹ and R ⁱⁱ² and / or R ⁱⁱ³ and R ⁱⁱ⁴ are bonded to each other to form a ring. You may,
n ⁱⁱ represents 0 or 1,
t represents 1 to 4, U represents a 2 × t-valent organic group forming a ring structure, R ⁱⁱ⁰ , R ⁱⁱ¹ , R ⁱⁱ² , R ⁱⁱ³ , R ⁱⁱ⁴ , R ⁱⁱ⁵ , R ⁱⁱ⁶ , R ⁱⁱ⁷ , R ^{If ii8} and n ⁱⁱ there are a plurality, they may be different even in the same. )
In general formula (i) and general formula (ii), R ⁱ⁰ and R ⁱⁱ⁰ are each a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms from the viewpoint of compatibility with the liquid crystal composition. It is preferably an alkoxy group or an alkenyl group having 2 to 20 carbon atoms, and is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an alkenyl group having 3 to 12 carbon atoms. Is more preferable. The alkyl group, alkoxy group or alkenyl group is preferably linear or molecular, and preferably linear. In view of ease of production, a hydrogen atom or a linear alkyl group having 1 to 5 carbon atoms is particularly preferable. In order to enhance the ability to prevent photodegradation, a hydrogen atom or a hydroxyl group is preferable, and a hydrogen atom is particularly preferable.

R ⁱ¹ , R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱⁱ¹ , R ⁱⁱ² , R ⁱⁱ³ and R ⁱⁱ⁴ are preferably each independently an alkyl group having 1 to 4 carbon atoms, A methyl group is particularly preferred from the viewpoint of the stability of the compound. In order to facilitate removal of polar impurities mixed during production, R ⁱ¹ and R ⁱ² and / or R ⁱ³ and R ⁱ⁴ are preferably bonded to each other to form a ring structure. Similarly, R ⁱⁱ¹ and R ⁱⁱ² and / or R ⁱⁱ³ and R ⁱⁱ⁴ are preferably bonded to each other to form a ring structure.

R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁸ , R ⁱⁱ⁵ , R ⁱⁱ⁶ , R ⁱⁱ⁷ and R ⁱⁱ⁸ are each independently preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, An alkyl group having 1 to 4 carbon atoms is preferable, and a hydrogen atom or a methyl group is particularly preferable from the viewpoint of availability of raw materials and stability of the compound.

In the compound represented by the general formula (i), m ⁱ is an integer of 1-6, M ⁱ represents 1 to hexavalent organic group, as many valence of M ⁱ is represented by n ⁱ although, m ⁱ is 3, M ⁱ is preferably a trivalent organic group.

When m ⁱ represents 3, M ⁱ represents the general formula (i−M)

(Wherein Z ¹ , Z ² and Z ³ are each independently —O—, —S—, —CH═CH—, —C≡C—, —CO—, —CO—O—, —O It represents —CO—, —OCF ₂ —, —CF ₂ O—, —NH— or a single bond.
Sp ¹ , Sp ² and Sp ³ each independently represent a single bond or an alkylene group having 1 to 10 carbon atoms, and one or more —CH ₂ — present in the alkylene group is independently Substituted with —O—, —S—, —CH═CH—, —C≡C—, —CO—, —CO—O—, —O—CO—, —OCF ₂ — or —CF ₂ O—. May be.
A is

(In the formula, R ⁸ represents a hydrogen atom, —OH or an alkyl group having 1 to 10 carbon atoms, and one or two or more —CH ₂ — present in the alkyl group are each independently —O—, —S—, —CH═CH—, —C≡C—, —CO—O—, —O—CO— may be substituted, and the hydrogen atom in the cyclic structure is a halogen atom or (It may be substituted with a cyano group.)
Represents a group selected from: )
In order to improve the compatibility with the liquid crystal composition and the storage stability, it is preferable.

Here, in terms of ease of production and availability of raw materials, at least one of Z ¹ , Z ² and Z ³ preferably represents —O—, —CO—O— or a single bond, and Z ¹ , It is particularly preferred that all of Z ² and Z ³ represent —O—, —CO—O— or a single bond. Sp ¹ , Sp ² and Sp ³ preferably represent a single bond or an alkylene group having 1 to 10 carbon atoms, preferably a single bond or an alkylene group having 1 to 8 carbon atoms, Alternatively, it is more preferably an alkylene group having 1 to 4 carbon atoms. The alkylene group is unsubstituted, or one or more —CH ₂ — present in the alkylene group is each independently —O—, —CO—, —CO—O— or —O—. It is preferably substituted with CO-, more preferably unsubstituted. ^{Specifically,} Sp ^1, Sp ² and ^Sp 3 _{_{_{are, -CO -, - CH 2 -CO}}} -, - CH 2 -CH 2 -CO -, - CH 2 -O -, - CH 2 -CH 2 - _{_{_{_{O -, - CH 2 -CH 2}}}} -CH 2 -O -, - CH 2 -O-CO -, - CH 2 -CH 2 -O-CO -, - CH 2 -CH 2 -CH 2 -O-CO Particularly preferred is an unsubstituted alkylene group having 1 to 4 carbon atoms or a single bond.

In addition, —Sp ¹ —Z ¹ —, —Sp ² —Z ² —, and —Sp ² —Z ² — are each independently —CO—O—, —CH ₂ —CO—O—, —CH ₂ —. _{_{_{_{CH 2 -CO-O -, -}}}} CH 2 -CH 2 --CH 2 -CO-O -, - CH 2 -O -, - CH 2 -CH 2 -O -, - CH 2 -CH 2 -CH 2 _{-O -, - CH 2 -O-} CO-O -, - preferably CH 2 -CH 2 -O-CO- O- or _{_{_{-CH 2 -CH 2 -CH 2 -O-}}} CO-O- in which _{, -CO-O -, - CH} 2 -CO-O- or more preferably _{_-CH} 2 _-CH 2 -CO-O- and which.

A is

(In the formula, R ⁸ represents a hydrogen atom, —OH or an alkyl group having 1 to 10 carbon atoms, and one or two or more —CH ₂ — present in the alkyl group are each independently A liquid crystal having a structure represented by —O—, —S—, —CH═CH—, —C≡C—, —CO—O— or —O—CO—. It is more preferable to improve the compatibility with the composition and the storage stability. Here, R ⁸ is a hydrogen atom, —OH, an alkyl group having 2 to 10 carbon atoms, —O—CO—R ⁹ (R ⁹ is 1 carbon atom) because of the ease of production and the availability of raw materials. Represents an alkyl group of ˜9, and particularly preferably represents a hydrogen atom.

Specifically, ^{compounds n i} is 3 as a general formula (i) is a compound represented by the general formula (i-a1) ~ (i -a14) are particularly preferred.

(R ¹¹ , R ¹² and R ¹³ in the formula independently represent the same meaning as R ⁱ⁰ in the general formula (i).)
Further, the compound represented by the general formula (i) is preferably a compound represented by the following general formula (i-1).

In general formula (i-1), R ^is each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and is particularly preferably a hydrogen atom. When it is an alkyl group, it preferably has 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, and 1 carbon atom. Further preferred. When a plurality of ^RHS are present, they may be the same or different.

M ^iS represents an alkyl group having 1 to 15 carbon atoms when m ^iS represents 1, and represents an alkylene group having 1 to 15 carbon atoms when m ^iS represents an integer of 2 to 6, and is present in M ^iS One or more —CH ₂ — represents —O—, —CH═CH—, —C≡C—, —CO—, —OCO—, —COO—, trans-1,4-cyclohexylene group, 1 , 4-phenylene group and naphthalene-2,6-diyl group may be substituted, but considering the viscosity given to the liquid crystal composition and its volatility, M ^iS is an alkyl group having 2 to 10 carbon atoms or An alkylene group is preferable, an alkyl group or alkylene group having 2 to 8 carbon atoms is preferable, an alkyl group or alkylene group having 4 to 8 carbon atoms is preferable, and an alkyl group or alkylene group having 6 or 8 carbon atoms is preferable. M ^iS may be linear or branched.

m ^iS represents an integer of 1 to 6, and preferably 2 to 4.

When m ^iS represents 1, the compound represented by the general formula (i-1) is preferably a compound represented by the general formula (i-11) or the general formula (i-12).

(Wherein R ^H11 independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and M represents an alkylene group having 1 to 13 carbon atoms.)

(In the formula, R ^is and R ⁱ¹¹ each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.)
When ^miS represents 2, the compound represented by the general formula (i-1) is preferably a compound represented by the general formula (i-2).

(In the formula, R ^H1 and R ^H2 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and M represents an alkylene group having 1 to 15 carbon atoms. One or more —CH ₂ — is —O—, —CH═CH—, —C≡C—, —CO—, —OCO—, —COO—, trans-1,4-cyclohexylene group, 1, (It may be substituted with a 4-phenylene group or a naphthalene-2,6-diyl group.)
In general formula (i-2), R ^H1 and R ^H2 are particularly preferably hydrogen atoms. When it is an alkyl group, it preferably has 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, and 1 carbon atom. Further preferred.
In general formula (i-2), M represents an alkylene group having 1 to 15 carbon atoms. However, considering the viscosity given to the liquid crystal composition and its volatility, M is an alkylene group having 2 to 10 carbon atoms. Preferably, alkylene having 4 to 8 carbon atoms is preferable, and alkylene having 6 or 8 carbon atoms is preferable.
Specific examples include compounds represented by general formula (i-24), general formula (i-26), and general formula (i-28). R ^H1 and R ^{H2 in} these formulas are as described above.

When ^miS represents an integer of 3 to 6, the compound represented by the general formula (i-1) is preferably a compound represented by the general formula (i-3).

(In the formula, R ^H3 , R ^H4 and R ^H5 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. N ^H1 and n ^H2 each independently represent 0 or 1 n. ^H3 represents an integer of 1 to 4. When n ^H3 is 2, 3 or 4, and a plurality of R ^H5 are present, they may be the same or different.
In general formula (i-3), R ^H3 , R ^H4 and R ^H5 are particularly preferably hydrogen atoms. When it is an alkyl group, it preferably has 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, and 1 carbon atom. Further preferred.

In the general formula (i-3), when n ^H3 represents 1, it is preferable to represent the above general formula (i-a1) to general formula (i-a3). In the general formula (i-3), when n ^H3 represents 2, compounds represented by the following general formula (i-31) and general formula (i-32) are preferable. R ^H3 , R ^H4 and R ^{H5 in} these formulas are as described above.

Examples of the compound n ⁱ represents 0 in the compound represented by the general formula (i), the following compounds are preferred.

The compound represented by the general formula (ii) is preferably a compound represented by the following general formula (ii-1) or general formula (ii-2).

(In the formula, R ⁱⁱ¹⁰ represents a hydrogen atom or a hydroxyl group, R ⁱⁱ¹² represents a hydrogen atom or a monovalent organic group,
Sp ⁱⁱ¹ represents a single bond or an alkylene group having a carbon number of from 12, one -CH ₂ present in the alkylene group - or nonadjacent two or more -CH ₂ - is -O -, - May be replaced by COO—, —OCO—, —CH═CH— or —C≡C—,
A ⁱⁱ¹ each independently (a) 1,4-cyclohexylene group (this is present in the group one -CH ₂ - or nonadjacent two or more -CH ₂ - is replaced by -O- May be.)
(B) a 1,4-phenylene group (one —CH═ present in the group or two or more non-adjacent —CH═ may be replaced by —N═) and (c) Naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or decahydronaphthalene-2,6-diyl group (naphthalene-2,6-diyl group or 1,2 , 3,4-tetrahydronaphthalene-2,6-diyl group, one —CH═ or two or more non-adjacent —CH═ may be replaced by —N═.
Each of the groups (a), (b) and (c) is independently substituted with a cyano group, a fluorine atom, a chlorine atom, a methyl group or a methoxy group. R ⁱⁱ¹¹ may be a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a general formula ( ^ie )

(Wherein R ^e1 represents a hydrogen atom or a hydroxyl group, Sp ^ie1 represents a single bond or an alkylene group having 1 to 12 carbon atoms, and one —CH ₂ — present in the alkylene group or adjacent thereto. And two or more —CH ₂ — may be replaced by —O—, —COO—, —OCO—, —CH═CH— or —C≡C—, and s1 represents 0 or 1.)
In represents a ^group represented by one -CH present in ^{R ii11} ₂ - or nonadjacent two or more -CH ₂ - is -O -, - S -, - COO -, - OCO- , -CO-, -CH = CH- or -C≡C-
n ⁱⁱ¹ represents 0 or 1, and p ⁱⁱ represents 0, 1 or 2, but when p ⁱⁱ represents 2, a plurality of Spii1 and Aii2 may be independently the same or different. . )

(In the formula, R ⁱⁱ¹⁰ and R ⁱⁱ²¹ each represent a hydrogen atom or a hydroxyl group, and n ⁱⁱ² , l, o, and r each independently represent 0 or 1)
The additive of the present invention only needs to be added in a very small amount in the liquid crystal composition, and may be contained in an amount of 0 ppm or more as a lower limit relative to the total amount of the liquid crystal compound and the additive, and may be contained in an amount of 0.0001% or more. 0.0002% or more may be contained, 0.0003% or more may be contained, 0.0004% or more may be contained, 0.0005% or more may be contained, and 0.0008% or more may be contained. 0.001% or more, 0.002% or more, 0.003% or more, 0.004% or more, 0.005% or more. It may be contained 0.006% or more, 0.007% or more, 0.008% or more, 0.009% or more, 0.01% or more. Well, 0.02% It may be contained above, 0.03% or more may be contained, 0.04% or more may be contained, 0.05% or more may be contained, 0.06% or more may be contained, 0.07% It may be contained at least 0.08%, 0.09% or more, 0.10% or more, 0.11% or more, 0.12% It may be contained above, 0.13% or more may be contained, 0.14% or more may be contained, 0.15% or more may be contained, 0.20% or more may be contained, 0.25% It may be contained in an amount of 0.30% or more, 0.35% or more, 0.40% or more, 0.50% or more, and 1% or more. do it. Further, the upper limit value is preferably 10% or less, preferably 5% or less, preferably 3% or less, preferably 2% or less, and preferably 1.5% or less. Preferably, contained 1% or less, preferably 0.9% or less, preferably 0.8% or less, preferably 0.7% or less, preferably 0.6% or less Preferably 0.5% or less, preferably 0.45% or less, preferably 0.4% or less, preferably 0.35% or less, .3% or less, preferably 0.25% or less, preferably 0.2% or less, preferably 0.15% or less, preferably 0.1% or less It is preferable to contain 0.07% or less, preferably 0.05% or less, preferably 0.03% or less, preferably 0.01% or less. 0.005% or less is preferable, and 0.003% or less is preferable.

More specifically, it is preferably contained from 0 ppm or more, preferably contained from 0 ppm or more to 0.005% by mass, preferably contained from 0.00001 to 0.005% by mass, and from 0.00001 to 0.005%. It is preferably 003% by mass, more preferably 0.00001 to 0.001% by mass, and particularly preferably 0.00001 to 0.0005% by mass.

Since the liquid crystal compound of the present invention is adjusted to a liquid crystal composition by mixing other liquid crystal compounds, a liquid crystal composition containing an additive having an effective minimum necessary additive amount is obtained. It becomes easy to control the amount of the additive when adjusted.

The container containing the liquid crystal compound and the additive of the present invention may be any container having airtightness. The material of the container may be any material that does not react with the liquid crystal compound and alter the liquid crystal compound, and preferably has corrosion resistance. For example, stainless steel, titanium, glass, resin, a composite material of these, and the like can be given, which may be rigid or flexible.

In the present invention, an additive is added to a liquid crystal compound to form a composition, and then the composition is stored in an airtight container. During storage, it is preferable to lower the oxygen concentration in the container, and it is preferable to fill with an inert gas such as nitrogen.

Liquid crystal compounds have different phase transition temperatures depending on the type. Therefore, in the case of a liquid crystal compound exhibiting a solid phase at room temperature, it is necessary to prepare a composition by adding an additive to the solid liquid crystal compound.

In the present invention, when an additive is added to a liquid crystal compound in a solid state, it is preferable to stir using a blending apparatus having a high stirring efficiency in order to obtain a more uniformly contained composition. Alternatively, the liquid crystal composition may be prepared by spraying an additive solution dissolved in a small amount of solvent onto a solid-state liquid crystal compound under stirring. The solvent used can be distilled off at room temperature or under reduced pressure.

In the present invention, after the liquid crystal compound in a solid state at room temperature is brought into a liquid crystal state or an isotropic liquid state, an additive for preventing the change of the liquid crystal compound may be added. As this method, it is preferable to add an additive after heating a liquid crystal compound in a solid state to be in a liquid crystal state or an isotropic liquid state. When the liquid crystal compound is distilled, the liquid crystal compound in the liquid crystal state or the isotropic liquid state can be mixed with the additive by placing the additive in a flask that receives the liquid crystal compound after distillation. Alternatively, the liquid crystal compound and the additive may be charged in a kettle and then distilled. Alternatively, a liquid crystal composition may be prepared by dissolving a solid-state liquid crystal compound in a solvent at room temperature or under heating, adding an additive, stirring and homogenizing, and then removing the solvent. . In addition, after passing the liquid crystal compound solution dissolved in the solvent through column chromatography made of silica gel or alumina, an additive is added, and the mixture is stirred and homogenized, and then the liquid crystal composition is prepared by removing the solvent. May be.

Moreover, in this invention, you may prepare a liquid-crystal composition by recrystallizing the mixture which consists of a liquid crystal compound and the additive and solvent which prevent modification of this liquid-crystal compound. The amount of additive contained in the liquid crystal composition obtained after recrystallization can be controlled by adjusting the amount of additive relative to the liquid crystal compound in the liquid mixture before recrystallization. Moreover, the quantity of the additive contained in the liquid crystal composition obtained after recrystallization can be controlled by selecting the kind of solvent. In addition, as a recrystallization method, a liquid crystal compound, an additive, and a solvent are stirred to obtain a uniform solution, cooled and crystallized, and then the solvent is removed by filtration to prepare a liquid crystal composition. Is preferred. In addition, a liquid crystal composition may be prepared by cooling a solution composed of a liquid crystal compound and a solvent, causing the solution to crystallize, adding an additive, and removing the solvent by filtration. The solvent remaining in the liquid crystal composition can be distilled off under reduced pressure at room temperature or with heating. Moreover, you may prepare a liquid-crystal composition by distilling off the solvent of the filtrate obtained by filtration of this crystal | crystallization.
In the present invention, the liquid crystal composition may be prepared by reprecipitation from a mixture comprising a liquid crystal compound, an additive for preventing alteration of the liquid crystal compound, and a solvent. Moreover, reprecipitation can be performed by adding a poor solvent in the solution containing a liquid crystal compound and an additive. Moreover, you may add the poor solvent containing an additive in the solution containing a liquid crystal compound. Moreover, you may add the solution containing a liquid crystal compound and an additive in a poor solvent. Moreover, you may add the solution containing a liquid crystal compound in the poor solvent containing an additive. A method of preparing a liquid crystal composition by removing the solvent by filtering the crystals obtained by these operations is preferred. The solvent remaining in the liquid crystal composition can be distilled off under reduced pressure at room temperature or with heating. Moreover, you may prepare a liquid-crystal composition by distilling off the solvent of the filtrate obtained by filtration of this crystal | crystallization.

The compound used in the present invention preferably has a high specific resistance value. As a lower limit, 9.9 × 10 ¹¹ Ω · m is preferable, 8.0 × 10 ¹¹ Ω · m is preferable, 5.0 × 10 ¹¹ Ω · m is preferable, and 1.0 × 10 ¹¹ Ω · m is preferable. 1.0 × 10 ¹⁰ Ω · m is preferable, 1.0 × 10 ⁹ Ω · m is preferable, 1.0 × 10 ⁸ Ω · m is preferable, and the upper limit value is 9.9 × 10 ¹¹ Ω · m. Preferably, 8.0 × 10 ¹¹ Ω · m is preferable, 5.0 × 10 ¹¹ Ω · m is preferable, 1.0 × 10 ¹¹ Ω · m is preferable, and 1.0 × 10 ¹⁰ Ω · m is preferable. 1.0 × 10 ⁹ Ω · m is preferable, and 1.0 × 10 ⁸ Ω · m is preferable. If the specific resistance is as high as necessary, no purification is required.

The compound used in the present invention does not need to be purified by other purification methods or recrystallization as long as it has a purity sufficient to withstand use, but in order to obtain a liquid crystal compound of sufficient purity, purification and recrystallization It is preferable to carry out. Further, the chemical purity of the compound used in the present invention is not particularly specified, but a higher one is desirable, and a compound having an area ratio of 95% or more in gas chromatography (column: DB-1, carrier gas: helium) is preferable. It is preferably used, desirably 97% or more, desirably 99% or more, desirably 99.5% or more, and more desirably 99.8% or more. Purification and recrystallization may be performed after mixing the additive with the compound.

As a purification agent used for column chromatography, it is preferable to use silica gel, alumina, or both. The purifying agent may be used after washing with pure water or an organic solvent in advance. Alumina may be acidic, basic or neutral.

The hydrocarbon solvent is preferably hexane or its structural isomer, heptane or its structural isomer, octane or its structural isomer, petroleum ether, benzene, toluene, xylene, or cumene, and hexane or its structural isomer. , Heptane or its structural isomer, or toluene.

Recrystallization can be performed by purifying the compound by column chromatography and then cooling the resulting solution. At this time, for the purpose of improving the yield of recrystallization, the solvent may be partially distilled off from the solution, and the concentration may be increased before recrystallization. If crystals are precipitated before recrystallization, it is preferable to recrystallize them after complete dissolution, but undissolved parts remain in the range that does not hinder the subsequent crystallization and filtration operations. May be. In cooling, it may be cooled rapidly or slowly. After cooling, the temperature may be kept constant, or crystals may be precipitated while further cooling. Moreover, when precipitating a crystal | crystallization, you may stir or may stand still. Stirring is preferred when the crystal sizes are aligned and the crystal size is not too large. The crystal may be precipitated in the air, but it is preferably performed in a rare gas or nitrogen atmosphere in order to prevent the influence of oxidation by oxygen in the air and the incorporation of moisture into the crystal. Moreover, although the crystal | crystallization is filtered in order to take out the precipitated crystal | crystallization, the method of natural filtration, reduced pressure filtration, pressure filtration, or centrifugal filtration can be taken. Moreover, when performing filtration, in order to prevent the influence of the oxidation by the oxygen in the air and moisture being taken into the crystal, it is preferably performed in a rare gas or nitrogen atmosphere. Moreover, what is normally used by filtration processes, such as a cellulose containing a paper, glass fiber, a membrane filter, and celite, can be used as a filter medium. In addition, the filtration may be performed at room temperature, cooled or heated.

The solvent used for recrystallization after filtering the crystals in the recrystallization step can be removed at room temperature or with heating under reduced pressure. At this time, the heating means is not particularly limited, and any method can be adopted as long as it can be controlled within a range of several degrees from the set temperature. For ease of implementation, a method of immersing a container filled with a liquid crystal compound in a temperature-controlled container filled with a solution, a method of heating the container with a mantle heater or the like, and a flow of flowing heated liquid on a shelf loaded with a liquid crystal compound The method of providing a path and heating by this is mentioned. Further, when the solvent is distilled off, the liquid crystal compound is cooled by the heat of vaporization, so that the above-mentioned means can be carried out with an unheated solution for the purpose of reducing the temperature drop. It is also possible to remove the solvent without using these methods and without controlling the temperature. In order to shorten the working time, the lower limit temperature is preferably 20 ° C, preferably 30 ° C, preferably 35 ° C, and more preferably 40 ° C. The upper limit temperature is preferably higher because the solvent distillation rate increases when the temperature is raised, but if the temperature is too high, decomposition or oxidation of the liquid crystal compound occurs, which is not preferred. Further, heating to a temperature higher than the melting point is not preferable because when it is cooled to room temperature after drying, it becomes an integral solid and cannot be obtained as a powder. For this reason, less than melting | fusing point is preferable, 60 degreeC is preferable, 55 degreeC is preferable, 50 degreeC is preferable, 45 degreeC is preferable and 40 degreeC is preferable. When the solvent is distilled off, the container or shelf containing the liquid crystal compound may be stationary or may be moved. However, it is preferable to rotate or vibrate from the viewpoint of efficiency.

The crystal obtained by recrystallization and the crystal of the present invention can then be mixed with an additive to prepare a liquid crystal composition. After forming the liquid crystal composition, filtration or treatment with an adsorbent may be performed as necessary.

It is preferable that the liquid crystal compound does not contain the solvent used for recrystallization, but it may be any concentration that does not adversely affect the liquid crystal composition. The concentration is preferably 200 ppm or less, preferably 100 ppm or less, preferably 50 ppm or less, and more preferably 20 ppm or less.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. Further, “%” in the compositions of the following Examples and Comparative Examples means “% by mass”.

The specific resistance value of the liquid crystal composition was obtained by placing the liquid crystal composition in a measurement cell and measuring the resistance value at a voltage (DC) of 1 V at 25 ° C.

In the examples and comparative examples, the purity was calculated from the area ratio of gas chromatography (column: DB-1, carrier gas: helium).
Example 1 Storage of Compound Represented by Formula (L-1-2.2) Formula (L-1-2.2)

697 g of a compound represented by the formula (purity 99.9920%) was weighed in a distillation kettle. Next, 133 mg of the additive represented by the formula (H-14) was accurately weighed into a round bottom flask as a vacuum distillation receiver. After vacuum distillation (1.0 kPa, steam temperature 130 ° C.), the vacuum distillation receiver was stirred at 37 ° C. for 10 minutes, so that 673 g of composition (E-1) (purity of L-1-2.2) The purity of 99.9750 & and H-14 was 0.0170%, and the combined purity was 99.9920%). The composition (E-1) was placed in an aluminum container, filled with nitrogen, and stored at 30 ° C. for 30 days. As a result of GC analysis, the combined purity of L-1-2.2 and H-14 was 99.9820%.
Example 2 Storage of Compound Represented by Formula (L-1-1.2) Formula (L-1-1.2)

3200 g of the compound represented by the formula (purity 99.9910%) was dissolved in 6400 ml of hexane at 40 ° C. Further, column chromatography was prepared with 960 g of silica gel, 1600 g of alumina and hexane, and 640 mg of the additive represented by the formula (H-14) was accurately weighed as a receiver in a round bottom flask. The column chromatography was charged with a hexane solution of formula (L-1-1.2) and received in a round bottom flask prepared earlier. Further, 10 L of hexane was passed through column chromatography and received in the same round bottom flask as before. The solvent of the obtained solution was distilled off under reduced pressure to obtain 3097 g of the composition (E-2) (L-1-1.2 purity 99.9730%, H-14 purity 0.0180%, Combined purity 99.9910%) was adjusted. The composition (E-2) was placed in an aluminum container, filled with nitrogen, and stored at 30 ° C. for 30 days. As a result of GC analysis, the combined purity of L-1-1.2 and H-14 was 99.9910%.
Example 3 Storage of Compound Represented by Formula (L-4.5) Formula (L-4.5)

20 g of a compound represented by the formula (purity 99.99994%) was dissolved in 60 ml of hexane at room temperature. Further, column chromatography was prepared with 6 g of silica gel, 10 g of alumina and hexane, and 4 mg of the additive represented by the formula (H-14) was accurately weighed in a round bottom flask as a receiver. This column chromatography was charged with a hexane solution of formula (L-4.5) and received in a round bottom flask prepared previously. Further, 77 ml of hexane was passed through column chromatography and received in the same round bottom flask as before. This mixed solution was precipitated by cooling to 0 ° C. and aged at −20 ° C. for 3 hours. The precipitated crystals were filtered and dried under reduced pressure to give 10 g of the composition (E-3) (L-4.5 purity 99.99990%, H-14 purity 0.0004%, and these were combined. Purity 99.99994%) was adjusted. The composition (E-3) was placed in a glass container, filled with nitrogen, and stored at 70 ° C. for 30 days. As a result of GC analysis, the combined purity of L-4.5 and H-14 was 99.9910%.
Example 4 Conservation of Compound Represented by Formula (Pb-3) Formula (Pb-3)

In a mixed solvent of 600 mL of methylene chloride and 500 mL of hexane, 100 g of the compound represented by the formula (purity 99.8611%) was dissolved. In addition, column chromatography was prepared using 200 g of silica gel, 100 g of alumina, and a mixed solvent of hexane and methylene chloride. As a receiver, 20 mg of the additive represented by the formula (H-14) was accurately weighed in a round bottom flask. I took it. The column chromatography was charged with a solution of formula (Pb-3) and received in a previously prepared round bottom flask. Further, a mixed solvent of 750 mL of hexane and 900 mL of methylene chloride was passed through column chromatography and received in the same round bottom flask as before. From this mixed solution, 2700 mL of the solvent was distilled off under reduced pressure. To this solution, 300 mL of hexane was slowly added to perform reprecipitation. After cooling at −10 ° C. for 2 hours, the crystals were filtered and dried under reduced pressure to give 90 g of composition (E-4) (Pb-3 purity 99.8606%, H-14 purity 0 .0005%, and the combined purity was 99.8611%). The composition (E-4) was placed in a glass container, filled with nitrogen, and stored at 60 ° C. for 90 days. As a result of GC analysis, the combined purity of L-4.5 and H-14 was 99.8301%.
Example 5 Storage of Compound Represented by Formula (L-1-1.3) Formula (L-1-1.3)

The compound represented by the formula (purity 99.9931) was dissolved in 100 ml of hexane. In addition, a column was prepared with 14.6 g of silica gel, 24.4 g of alumina and hexane, and a hexane solution of the formula (L-1-1.3) was charged through this column, passed through, and further eluted with 160 ml of hexane. The solvent of the obtained solution was distilled off under reduced pressure. The resulting residue was dried under reduced pressure for 3 hours while warming in a 37 ° C. water bath. The resulting viscous liquid was distilled under reduced pressure (0.8 mmHg) while heating (250 ° C.), and collected in a round bottom flask to which 10 mg of the formula (H-14) had been weighed in advance. The resulting mixture was stirred for 10 minutes in an argon atmosphere while warming in a 48 ° C. water bath, and 49 g of composition (E-5) (L-1-1.3 purity 99.99728%, H-14 purity) 0.0192%, the combined purity of 99.9920%) was adjusted. The composition (E-5) was placed in a glass container and stored at 70 ° C. for 20 days under atmospheric pressure. As a result of GC analysis, the combined purity of L-1-1.3 and H-14 was 99.9920%.
Example 6 Storage of Compound Represented by Formula (L-5.4) Formula (L-5.4)

The compound represented by the formula (purity 99.99958) was dissolved in 130 ml of hexane. A column was prepared with 7.5 g of silica gel, 12.5 g of alumina, and hexane, and 5 mg of the additive represented by the formula (H-14) was accurately weighed in a round bottom flask as a receiver. The column was charged with a hexane solution of the formula (L-5.4), passed through and eluted with 120 ml of hexane, and 140 ml of the solvent of the resulting solution was distilled off under reduced pressure. The obtained solution was allowed to stand at −20 ° C. for 2 hours to precipitate crystals. The precipitated crystals were collected by filtration and dried under reduced pressure for 18 hours while heating in a 45 ° C. water bath, and 19 g of the composition (E-6) (L-5.4 having a purity of 99.9961%, H-14 The purity was adjusted to 0.0009% and the combined purity of 99.9970%). The composition (E-6) was placed in a glass container and stored at 70 ° C. for 30 days under atmospheric pressure. As a result of GC analysis, the combined purity of L-5.4 and H-14 was 99.8360%.
Example 7 Storage of Compound Represented by Formula (L-5.4) Formula (L-5.4)

The filtrate obtained at the time of crystal filtration in Example 6 was concentrated under reduced pressure, and then dried under reduced pressure for 12 hours while heating in a 45 ° C. water bath, and 4 g of composition (E-7) (L-5.4). Purity of 99.9091%, purity of H-14 of 0.0789%, and the combined purity of 99.9880%). The composition (E-7) was placed in a glass container and stored at 70 ° C. for 30 days under atmospheric pressure. As a result of GC analysis, the combined purity of L- and H-14 was 99.9710%.
Example 8 Storage of Compound Represented by Formula (N-1-3.6) Formula (N-1-3.6)

100 g of the compound represented by the formula (purity: 99.9974%) was dissolved in 1000 ml of hexane. Further, a column was prepared with 30 g of silica gel, 50 g of alumina and hexane, and 100 mg of the additive represented by the formula (H-14) was accurately weighed as a receiver in a round bottom flask. The column was charged with a hexane solution of formula (N-1-3.6) at 50 ° C., passed through, and further eluted with 363 ml of hexane. The obtained solution was allowed to stand at −20 ° C. for 2 hours to precipitate crystals. The precipitated crystals were collected by filtration and dried under reduced pressure for 15 hours while heating in a 45 ° C. water bath, and 87 g of the composition (E-8) (N-1-3.6 having a purity of 99.9806%, H— 14 purity of 0.0168% and the combined purity of 99.9974%) were adjusted. The composition (E-8) was placed in a glass container, filled with nitrogen, and stored at 70 ° C. for 30 days. As a result of GC analysis, the combined purity of N-1-3.6 and H-14 was 99.9972%.
Example 9 Preservation of Compound Represented by Formula (N-1-11.14) Formula (N-1-11.14)

27.5 g of a compound represented by the formula (purity: 99.9879%) was dissolved in 110 ml of hexane. A column was prepared with 8.2 g of silica gel, 13.8 g of alumina, and hexane, and 30 mg of the additive represented by the formula (H-14) was accurately weighed in a round bottom flask as a receiver. The column was charged with a hexane solution of formula ((N-1-11.14)) at 55 ° C., passed through, and eluted with 91 ml of hexane. The obtained solution was allowed to stand at −20 ° C. for 2 hours to precipitate crystals. The precipitated crystals were collected by filtration and dried under reduced pressure for 15 hours while heating in a water bath at 50 ° C., and 25.1 g of the composition (E-9) (N−1-11.14 purity 99.9799%, The purity of H-14 was 0.0080%, and the combined purity was 99.9879%). The composition (E-9) was placed in a glass container, filled with nitrogen, and stored at 60 ° C. for 20 days. As a result of GC analysis, the combined purity of N-1-3.6 and H-14 was 99.9860%.
Example 10 Storage of Compound Represented by Formula (L-3.1) Formula (L-3.1)

20 g (purity 99.9875%) represented by the formula was dissolved in hexane 80 ml. Further, a column was prepared with 6 g of silica gel, 10 g of alumina and hexane, and 30 mg of the additive represented by the formula (H-14) was accurately weighed in a round bottom flask as a receiver. The column was charged with a hexane solution of formula (L-3.1), passed through, and further eluted with 66 ml of hexane. The obtained solution was allowed to stand at −20 ° C. for 2 hours to precipitate crystals. The precipitated crystals were collected by filtration and dried under reduced pressure for 15 hours while heating in a 45 ° C. water bath, and 17 g of the composition (E-10) (L-3.1 purity 99.9835%, H-14 The purity was adjusted to 0.0040%, and the combined purity of 99.9875%). The composition (E-10) was placed in a glass container, filled with nitrogen, and stored at 70 ° C. for 20 days. As a result of GC analysis, the combined purity of L-3.1 and H-14 was 99.9810%.
(Comparative Example 1)
10 g of the compound represented by the formula (L-1-2.2) (purity 99.9920%) was placed in an aluminum container, filled with nitrogen, and stored at 30 ° C. for 30 days. As a result of GC analysis, the purity was 99.9660%.
(Comparative Example 2)
10 g of the compound represented by the formula (L-1-1.2) (purity 99.9910%) was placed in an aluminum container, filled with nitrogen, and stored at 30 ° C. for 30 days. As a result of GC analysis, the purity was 99.8810%.
(Comparative Example 3)
10 g of the compound represented by the formula (L-4.5) (purity 99.9910%) was placed in a glass container, filled with nitrogen, and stored at 70 ° C. for 30 days. As a result of GC analysis, the purity was 73.1457%.
(Comparative Example 4)
10 g of the compound represented by the formula (Pb-3) (purity: 99.8611%) was placed in a glass container, filled with nitrogen, and stored at 60 ° C. for 90 days. As a result of GC analysis, the purity was 98.5398%.

(Comparative Example 5)
10 g of the compound represented by the formula (L-1-1.3) (purity 99.9920%) was placed in a glass container and stored at 70 ° C. for 20 days under atmospheric pressure. As a result of GC analysis, the purity was 39.8874%.
(Comparative Example 6)
10 g of the compound represented by the formula (L-5.4) (purity 99.99958%) was placed in a glass container and stored at 70 ° C. for 30 days under atmospheric pressure. As a result of GC analysis, the purity was 45.5839%.
(Comparative Example 7)
10 g of the compound represented by the formula (N-1-3.6) (purity: 99.9974%) was placed in a glass container and stored at 70 ° C. under atmospheric pressure for 30 days. As a result of GC analysis, the purity was 99.9813%.
(Comparative Example 8)
10 g of the compound represented by the formula (N-1-11.14) (purity: 99.9879%) was placed in a glass container, filled with nitrogen, and stored at 60 ° C. for 20 days. As a result of GC analysis, the purity was 99.89553%.
(Comparative Example 9)
10 g of the compound represented by the formula (L-3.1) (purity: 99.9875%) was placed in a glass container, filled with nitrogen, and stored at 70 ° C. for 20 days. As a result of GC analysis, the purity was 99.9610%.

Tables 1 and 2 show the results of GC analysis of the above examples and comparative examples, respectively.

Referring to Tables 1 and 2, it can be seen that the liquid crystal composition of Example 1-7 can be stored for a long time while maintaining a high level of purity.

Claims

Substantially containing one type of liquid crystal compound and an additive for preventing the liquid crystal compound from being altered,
A composition contained in an airtight container.
2. The composition according to claim 1, wherein the additive for preventing deterioration of the liquid crystal compound is one or more compounds selected from an antioxidant and an ultraviolet ray inhibitor.
The liquid crystal compound is represented by the general formula (L)

(Wherein R L1 represents an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently —CH═CH—, — Optionally substituted by C≡C—, —O—, —CO—, —COO— or —OCO—,
A L1 and A L2 are each independently (a) 1,4-cyclohexylene group (this is present in the group one -CH 2 - or nonadjacent two or more -CH 2 - is -O And (b) a 1,4-phenylene group (one —CH═ present in the group or two or more non-adjacent —CH═ are replaced with —N =). May be.)
(C) 1,4-cyclohexenylene group, naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group ( One —CH═ present in a naphthalene-2,6-diyl group or 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or two or more non-adjacent —CH═ are — N = may be substituted, and a hydrogen atom present in these groups may be substituted with a fluorine atom.)
The group (a), the group (b) and the group (c) are each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
Z L1 is a single bond, —CH 2 CH 2 —, — (CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O— -CH = NN-CH-, -CH = CH-, -CF = CF- or -C≡C-
R L2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or an alkyl group having 1 to 10 carbon atoms, and one or two or more non-adjacent —CH 2 — in the alkyl group are each independently Optionally substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO— or —OCO—, and one or more hydrogens in the alkyl group The atom may be substituted with a fluorine atom,
m L1 represents 1, 2, 3 or 4, but when m L1 represents 2, 3 or 4, a plurality of A L1 and Z L1 may be the same or different. )
Or general formula (P)

(In the general formula (P), Z p1 represents a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms in which a hydrogen atom may be substituted with a halogen atom, and a hydrogen atom in a halogen atom. An optionally substituted alkoxy group having 1 to 15 carbon atoms, a hydrogen atom optionally substituted with a halogen atom, and an alkenyl group having 1 to 15 carbon atoms optionally substituted with a halogen atom Represents an alkenyloxy group having 1 to 15 carbon atoms or —Sp p2 —R p2 ;
R p1 and R p2 are each independently the following formulas (RI) to (R-IX):

In the formulas (RI) to (R-IX), R 2 to R 6 are independently of each other a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or the number of carbon atoms. 1 to 5 halogenated alkyl groups, W is a single bond, —O— or a methylene group, T is a single bond or —COO—, and p, t and q are each independently 0, Represents 1 or 2,
Sp p1 and Sp p2 represent spacer groups,
L p1 and L p2 are each independently a single bond, —O—, —S—, —CH 2 —, —OCH 2 —, —CH 2 O—, —CO—, —C 2 H 4 —, — COO—, —OCO—, —OCOOCH 2 —, —CH 2 OCOO—, —OCH 2 CH 2 O—, —CO—NR a —, —NR a —CO—, —SCH 2 —, —CH 2 S— , -CH = CR a -COO -, - CH = CR a -OCO -, - COO-CR a = CH -, - OCO-CR a = CH -, - COO-CR a = CH-COO -, - COO -CR a = CH-OCO -, - OCO-CR a = CH-COO -, - OCO-CR a = CH-OCO -, - (CH 2) z -C (= O) -O -, - (CH 2 ) z—O— (C═O) —, —O— (C═O) — (CH 2 ) z—, — (C═O) —O — (CH 2 ) z—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —CF 2 —, —CF 2 O—, —OCF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 — or —C≡C— (wherein each R a independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, In the above formula, z represents an integer of 1 to 4.
M p2 represents 1,4-phenylene group, 1,4-cyclohexylene group, anthracene-2,6-diyl group, phenanthrene-2,7-diyl group, pyridine-2,5-diyl group, pyrimidine-2, 5-diyl group, naphthalene-2,6-diyl group, indan-2,5-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5 -Represents a diyl group, but M p2 is unsubstituted or an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a carbon atom May be substituted with a halogenated alkoxy group of formula 1 to 12, a halogen atom, a cyano group, a nitro group or —R p1 ;
M p1 represents the following formulas (i-11) to (ix-11):

(In the formula, it binds to Sp p1 with ★ and binds to L p1 or L p2 with ★★),
M p3 represents the following formulas (i-13) to (ix-13):

(In the formula, it binds to Z p1 with ★ and binds to L p2 with ★★),
m p2 to m p4 each independently represents 0, 1, 2 or 3, m p1 and m p5 each independently represent 1, 2 or 3, but when there are a plurality of Z p1 May be the same or different. When a plurality of R p1 are present, they may be the same or different. When a plurality of R p2 are present, they may be the same. They may be different, they may be the same or different when multiple Sp p1 are present, and they may be the same or different when multiple Sp p2 are present, When a plurality of L p1 are present, they may be the same or different, and when a plurality of M p2 are present, they may be the same or different. )
The composition of Claim 1 or 2 which is a compound represented by these.
The composition according to claim 2 or 3, wherein the content of the additive is 10% by mass or less in the liquid crystal composition.
A method for storing a liquid crystal composition using a container having airtightness, wherein a liquid crystal composition containing substantially one type of liquid crystal compound and an additive for preventing alteration of the liquid crystal compound is used.
The manufacturing method of the liquid crystal composition which adds the additive which prevents a change of this liquid crystal compound to the liquid crystal compound of a solid state, and prepares the liquid crystal composition in which a liquid crystal compound is substantially comprised only by 1 type.
After a liquid crystal compound in a solid state at room temperature is dissolved in a liquid crystal state or an isotropic liquid state or a solvent to form a solution state, an additive for preventing the liquid crystal compound from being altered is added, and substantially one type of liquid crystal compound and A method for producing a liquid crystal composition, comprising preparing a liquid crystal composition comprising an additive for preventing deterioration of the liquid crystal compound.
Consists of a liquid crystal compound, an additive for preventing alteration of the liquid crystal compound, and an additive for preventing alteration of the liquid crystal compound by recrystallization or reprecipitation from a mixture comprising a solvent. A method for producing a liquid crystal composition for preparing a liquid crystal composition.