JPH04316545A - New amine derivative - Google Patents

Abstract

PURPOSE:To provide the subject new optically inactive and chemically stable amine derivatives showing liquid crystallinity over a wide temperature range. CONSTITUTION:Amine derivatives of formula I [R1 and R3 are 1-18C optically inactive alkyl which may contain branched chain; (may be partly substituted with halogen); R2 is H, methyl or ethyl; PHI is 1,4-phenylene; X is COO or OCO; m and n are 0 or 1], e.g. 4-[N-3-methylbutyl-N-methylaminomethyl]-benzoic acid 4''-pentyloxycarbonyl-4'-biphenyl ester. The compounds of formula I can be obtained by esterifying a compound of formula II or its salt with a compound of formula III in case of X=COO or esterifying a compound of formula IV or its salt with a compound of formula V in case of X=OCO.

Description

[Detailed description of the invention]

0001

FIELD OF INDUSTRIAL APPLICATION This invention provides novel compounds exhibiting liquid crystals, methods for producing the same, and liquid crystal devices using these compounds.

0002

BACKGROUND OF THE INVENTION Among many known liquid crystal compounds, there is one called nematic liquid crystal. Although this compound is currently the mainstream of compounds or compositions used in liquid crystal display devices, one of its disadvantages is that the response speed is slow, and a response speed of only a few milliseconds can be obtained. Therefore, it is said that we are approaching the limit for increasing the size of the display.

[0003] In order to improve the drawbacks of conventional liquid crystal display elements, the use of a liquid crystal having bistability was proposed by Clark and Lagerwell (Japanese Unexamined Patent Application Publication No. 1983-1930).
No. 6-107216). This liquid crystal with bistability is
Called ferroelectric liquid crystals, they have attracted attention for their high-speed response and memory properties, and research into their practical application has been particularly active in recent years, making the development of practical ferroelectric liquid crystal materials an urgent task.

In general, ferroelectric liquid crystals are compounds having optically active sites and are expressed in a series of smectic phases having a molecular orientation in which the long axis of the molecules is tilted from the normal direction of the layer. Among them, chiral smectic C (hereinafter referred to as SC)
Abbreviated as *. ) phase is considered to be advantageous in practice due to its relatively low voltage operability.

As described above, ferroelectric liquid crystals have a very fast response speed due to their spontaneous polarization, and can also develop a bistable state with memory properties, and also have excellent viewing angles. Therefore, it is suitable as a material for large-capacity, large-screen displays.

As such a ferroelectric liquid crystal, in 1975, R. B. 4-(4-n) synthesized by Meyer et al.
-decyloxybenzylideneamino)cinnamic acid-2-methylbutyl ester (hereinafter abbreviated as DOBAMBC).
is known (J. Physique 36 L
-69 (1975)).

[0007] DOBAMBC contains a Schiff base in its structure, and therefore has a problem in its chemical stability. Therefore, various physically and chemically stable compounds have been searched for as ferroelectric liquid crystal materials, and currently 4-(4-n-alkyloxyphenyl)-1-carboxylic acid-2-methylbutyl ester (hereinafter referred to as CN The main focus has shifted to the search for ester-based compounds such as (abbreviated as ). but,
Ester compounds such as CN do not exhibit the Sc* phase, or even if they do, the temperature range in which they exhibit the Sc* phase is narrow, and moreover, they are monotropic liquid crystals that exhibit different phase series when the liquid crystal is heated or cooled. Therefore, there are few that can withstand practical use (Liquid Crystals
and Ordered Fluids 4 (1
984)).

On the other hand, many ferroelectric liquid crystal compounds containing a hetero atom are known, but compounds containing a nitrogen atom include those containing it as a hetero ring such as a pyrimidine ring (Japanese Patent Application Laid-Open No. 61-22072, 24576, 129170). issue)
, and those containing a Schiff base such as DOBAMBC as a bonding group are known.

Among compounds containing a nitrogen atom as a bonding group, Schiff's bases have poor chemical stability as mentioned above. Furthermore, compounds containing amide bonds generally have a high melting point and are difficult to exhibit liquid crystallinity, so they cannot be said to be effective.

As an example of a liquid crystal in which a nitrogen atom is introduced in the form of an amine, there is an example in which an amine is first introduced into an alkyl chain using tranexamic acid as a raw material to provide a liquid crystal compound that is inexpensive and exhibits a wide liquid crystal temperature range ( JP 3-218338
(Japanese Patent Application No. 2-149487). In addition, as examples of introducing aromatic amines, there are examples of introducing aromatic secondary amines (JP-A-63-2961, JP-A-2-537).
No. 56).

However, only examples have been disclosed in which a single compound exhibits liquid crystallinity in an inappropriate temperature range or at a high temperature, and has not yet reached a practical stage.

Therefore, attempts have been made to mix these liquid crystal compounds to widen the temperature range in which they exhibit liquid crystallinity, to lower the liquid crystal temperature, and to reduce costs, but in general, in ferroelectric liquid crystal compositions, optical When mixing active compounds, the chiral smectic C phase and cholesteric phase between the optically active liquid crystal compounds of the composition, the left and right direction of the pitch, the size, the polarity of spontaneous polarization, etc. must be considered. .

On the other hand, if a non-optically active liquid crystal composition having no spontaneous polarization is used as a matrix, chiral smectic C
It is possible to mix the components without considering the phase, the cholesteric phase, the direction of each pitch, the polarity of spontaneous polarization, etc., and it becomes possible to obtain an effective ferroelectric liquid crystal composition. A method has been developed and commonly used to add a small amount of an optically active compound to a stable, non-optically active liquid crystal composition that exhibits liquid crystallinity, particularly smectic C phase, over a wide temperature range to develop ferroelectricity. became. Therefore, non-optical compounds that exhibit stable liquid crystallinity are strongly desired.

[0014]

SUMMARY OF THE INVENTION An object of the present invention is to provide a novel non-optically active amine derivative that is chemically stable and exhibits liquid crystallinity over a wide temperature range.

Furthermore, the type of alkyl group can be easily changed.
, N-disubstituted amine derivatives as intermediates to develop a novel method for producing liquid crystal compounds. In addition, the type and length of the alkyl group and the type of ester group can be easily changed,
The object of the present invention is to provide a liquid crystal compound capable of controlling the type and temperature range of the liquid crystal phase developed in a liquid crystal state, and a liquid crystal composition containing at least one compound thereof as a compounding component.

[0016]

[Means for Solving the Problems] In the present invention, an N,N-disubstituted amine derivative is used as an intermediate, and this is reacted with a biphenyl derivative to perform esterification, thereby exhibiting stable liquid crystallinity over a wide temperature range. succeeded in synthesizing the compound.

That is, general formula (I) (R1)(R2)N-(CH2)m-Φ-
X-Φ-Φ-(CO)n-OR3


...(I) (in the formula, R1 and R3 are non-optically active alkyl groups having 1 to 18 carbon atoms that may contain a branched chain, a part of which may be substituted with halogen, and R2
is hydrogen, methyl group or ethyl group, Φ is 1,4-phenylene group, X is COO or OCO, m and n are each 0
Or represents 1. ) was obtained.

The amine derivative of the present invention has an N,N-disubstituted amine derivative moiety with adjacent aromatic rings, (R1)(R2)N-(CH2)m-Φ- and a biphenyl derivative moiety -Φ-Φ-( It is divided into two parts: CO)n -OR3, and these two parts are linked by an ester bond.

Regarding R1, it is a non-optically active alkyl group having 1 to 18 carbon atoms which may contain a branched chain, and a part of which may be substituted with halogen, preferably an alkyl group having 3 to 7 carbon atoms. Therefore, the use of a branched alkyl group tends to increase the thermal stability of liquid crystals.

R2 is hydrogen, methyl group or ethyl group. Methyl groups and ethyl groups are preferable, but when the number of carbon atoms is 3 or more, liquid crystallinity decreases, which is not preferable.

R3 represents a non-optically active alkyl group having 1 to 18 carbon atoms which may contain a branched chain, but having 5 to 18 carbon atoms.
12 is preferable, and when the number of carbon atoms is 7 or less or an odd number, the temperature range of the liquid crystal tends to become wider.

The compound of the present invention has the general formula (I)
The ester bond represented by is COO or OC
It can be manufactured according to the following manufacturing method, although it depends on whether it is O or not.

That is, if ) is reacted with a biphenyl derivative having a hydroxyl group attached to the 4-position of the biphenyl group (represented by general formula (III)). For example, (R1)(R2)N-(
CH2)m -Φ-COOH


...A compound represented by (II) or a salt thereof and general formula (III)
HO-Φ-Φ-(CO)n-OR3


...(III) By esterifying the compound represented by the general formula (Ia) (R1) (R2)N- (CH2)m -Φ-CO
O-Φ-Φ- (CO)n-OR3


...(Ia) (in the formula, R1 and R3 are non-optically active alkyl groups having 1 to 18 carbon atoms that may contain a branched chain, and a portion thereof may be substituted with halogen, and R2 is hydrogen, methyl or ethyl group, Φ is a 1,4-phenylene group, and m and n each represent 0 or 1).

When X=OCO (represented by the general formula (Ib)), the above-mentioned carboxyl group and hydroxyl group are replaced (represented by the general formulas (IV) and (V)).
can be obtained by reacting in the same manner.

That is, general formula (IV) (R1 )(R2 )N-(
CH2)m-Φ-OH

…
...(IV) or a salt thereof and the general formula (
V) HOOC-
Φ−Φ−(CO)n −OR3


...By esterifying the compound represented by (V), the general formula (Ib) (R1) (R2)N- (CH2)m -Φ-OC
O-Φ-Φ- (CO)n-OR3


...(Ib) (in the formula, R1 and R3 are non-optically active alkyl groups having 1 to 18 carbon atoms that may contain a branched chain, a part of which may be substituted with halogen, and R2 is hydrogen, methyl or ethyl group, Φ is a 1,4-phenylene group, and m and n each represent 0 or 1).

These esterifications are carried out using dicyclohexylcarbodiimide (hereinafter abbreviated as DCC) or thionyl chloride.

The amine intermediate represented by the general formula (II) or (IV) is prepared by attaching a protecting group to the active hydrogen of the corresponding amine, and then adding a halogenated alkyl group having an alkyl group corresponding to R1 and R2. It can be obtained by N-alkylation using a base such as sodium hydride.

For example, the compound represented by the general formula (II) is prepared by first using the corresponding commercially available primary amine as a raw material, introducing a t-butyloxycarbonyl group as a protecting group for the amine, and converting it to N-methyl with a methyl halide. A protecting group for a carboxyl group can be formed by carrying out esterification and esterification at the same time (see FIG. 1(A)). Next, the protecting group was removed with hydrochloric acid, and N was added with the alkyl halide corresponding to R1.
-alkylation and finally hydrolysis of the ester to obtain compound (II) (see Figure 1(B)).

In particular, when m=0 and R2 is methyl, it is possible to shorten the one-step reaction by using commercially available N-methylaminobenzoic acid and esterifying it with methanol or ethanol (Fig. (See 1(C))
.

In the compound represented by (IV), an amine moiety is derived by reduction of the nitrile when m=1 and reduction of the nitro group when m=0 (see FIGS. 2(D) and (E)),
It can be obtained by attaching a protecting group to the phenolic hydroxyl group and the amine moiety in the same manner as in the case of (II), and then N-alkylating it with an alkyl halide corresponding to R1 and R2 (see Figure 2 (F)). . At this time, a protecting group for the phenolic hydroxyl group is required, but by using a p-toluenesulfonyl group when m = 1 and a benzyl group when m = 0, the reduction reaction and deprotection reaction can be carried out with high yield. It can be carried out.

FIGS. 1 and 2 show amine intermediate (II), (
The reaction route of compounds represented by general formulas (Ia) and (Ib) via IV) is shown.

The compound produced by the above method is purified by column chromatography and recrystallization.

The compound represented by the general formula (III) is
It can be obtained in the same manner as the method shown in JP-A-3-218338. Furthermore, commercially available compounds can be used as the compound represented by the general formula (V).

[0034]

[Action] General formula (I) (R1)(R2)N-(CH2)m-Φ- in the present invention
X-Φ-Φ-(CO)n-OR3


...(I) (in the formula, R1 and R3 are non-optically active alkyl groups having 1 to 18 carbon atoms that may contain a branched chain, a part of which may be substituted with halogen, and R2
is hydrogen, methyl group or ethyl group, Φ is 1,4-phenylene group, X is COO or OCO, m and n are each 0
Or represents 1. ) is a non-optically active amine derivative that has a low melting point and exhibits extremely stable liquid crystallinity.

In particular, compounds of the present invention having amino groups present between methylene groups (corresponding to compounds where m=1 in general formula (I)) exhibit enantiotropic liquid crystallinity; It is presumed that this is because the amino groups present between the groups promote polarization of the molecule, making it easier to obtain liquid crystal alignment.

From these results, it has been found that compounds having an amine in the molecule have the effect of stabilizing liquid crystallinity, unlike amide bonds and the like having strong intermolecular hydrogen bonds.

The compounds developed in this way are compounds having an alkyl chain having an expensive asymmetric carbon (Japanese Patent Application No.
6948), and because it uses an alkyl chain with a wide variety of variations, it is easy to change the side chain. Therefore, it is possible to consider optimizing the side chain to achieve the ideal liquid crystal temperature range. Next, since the compound of the present invention is a non-optically active liquid crystal compound, it can be mixed as a material for a ferroelectric liquid crystal composition without considering material constants such as the direction of the helix and the polarity of spontaneous polarization. Since they can be mixed, there is a high degree of freedom in combinations.

Furthermore, since it is a non-optically active liquid crystal and does not have a helix, it is possible to lengthen the helical pitch of the chiral smectic C phase by adding it to a ferroelectric liquid crystal composition.

Furthermore, it is easier to adjust the ideal liquid crystal phase series and temperature range with a non-optically active compound, and by adding a small amount of chiral dopant to this, a ferroelectric liquid crystal composition can also be created with a controlled phase series and liquid crystal temperature. doesn't change much. Conversely, even if the liquid crystal compound of the present invention is mixed into the phase series in which the ferroelectric liquid crystal composition has obtained a good alignment state, the composition has a more effective liquid crystal temperature range without disturbing the mutual phase series. be able to.

The compound of the present invention is a novel non-optically active amine derivative that can be used as a component of a liquid crystal display element having excellent responsiveness and memory properties for the above reasons.

[0041]

EXAMPLES The compounds of the present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples.

[0042] Below, Cry, N, SA, SC, Is
The o phases represent a crystal, a nematic phase, a smectic A phase, a smectic C phase, and an isotropic liquid, respectively, and SX represents a higher-order structure of the smectic phase.

The compound of the present invention was purified by silica gel chromatography and recrystallization from ethyl acetate, hexane, etc.

The measured values of the phase transition points shown below may be slightly influenced by the purity of the material.

(Example 1) Synthesis of 4-[N-3-methylbutyl-N-methylaminomethyl]-benzoic acid-4''-pentyloxycarbonyl-4'-biphenyl ester ■ 4-(N-t-butyl Synthesis of (oxycarbonylaminomethyl)benzoic acid 7.56 g of 4-aminomethylbenzoic acid was mixed with dioxane.
1M Na dissolved in 150 ml of water (2:1) in an ice bath.
Add 50ml of OH aqueous solution dropwise over 10 minutes, then add
12.6 g of t-butyl dicarbonate was added dropwise. The mixture was returned to room temperature and stirred overnight. Then, the reaction solution was concentrated under reduced pressure to about ⅓ volume, and the pH was adjusted to 4 using 1N-HCl. Extracted with ethyl acetate (700 ml), then the organic layer was mixed with purified water (200 ml) and saturated brine (100 ml).
After washing with water and dehydrating with anhydrous magnesium sulfate, the solvent was
It was concentrated under reduced pressure to 00 ml and crystallized to give a white powder of 4-(N
6.10 g of -t-butyloxycarbonylaminomethyl)benzoic acid was obtained.

■ Synthesis step of 4-(N-t-butyloxycarbonyl-N-methylaminomethyl)benzoic acid methyl ester 8.60 g of the crystals obtained in step (2) was dissolved in N,N-dimethylformamide and placed in an ice bath. Among them, 17.4 m of methyl iodide
1 was added dropwise, 4.12 g of 60% sodium hydride was added little by little, and after stirring for 30 minutes, the mixture was returned to room temperature and stirring was continued overnight. Purified water (100 ml) was added to this reaction solution, and the mixture was extracted with ether (250 ml). The organic layer was mixed with saturated sodium hydrogen carbonate (200 ml) and saturated brine (100 ml).
After washing with and dehydrating with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 10.8 g of crude 4-(N-t-butyloxycarbonyl-N-methylaminomethyl)benzoic acid methyl ester as a pale yellow oil. .

■ Synthesis step of 4-(N-methylaminomethyl)benzoic acid methyl ester hydrochloride 10.8 g of the compound obtained in step (2) was added with 4N hydrochloric acid/ethyl acetate solution (23.3 ml) in an ice bath, and the mixture was heated to room temperature. and stirred for 3 hours. After standing overnight, 40 ml of ethyl acetate was added, the resulting crystals were collected by filtration, and 7.8 g of crude 4-(N-methylaminomethyl)benzoic acid methyl ester hydrochloride was obtained as a white powder.
Obtained.

■ 4-(N-3-methylbutyl-N-
7.8 g of the crystals obtained in Step ① of synthesis of methylaminomethylbenzoic acid were dissolved in N,N-dimethylformamide (50 ml), and triethylamine (methylaminomethyl)benzoate was dissolved in an ice bath.
5.0 ml), 1-bromo-3-methylbutane (5.8
ml) were added dropwise, and sodium hydride (1.87 g) was added dropwise.
was added little by little and heated at 90°C for 4 hours. After cooling, purified water (40 ml) was added dropwise, extracted with ether (300 ml), washed with saturated brine, dehydrated with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Obtained orange oil 8
．． 4g was subjected to silica gel column chromatography to obtain 5.14g of transparent extremely pale yellow 4-(N-3-methylbutyl-N-methylaminomethylbenzoic acid methyl ester) from the fraction of ethyl acetate-hexane (1:6). Ta.

■ 4-(N-3-methylbutyl-N-
6N-
Hydrochloric acid (34 ml) was added dropwise, and the mixture was heated at 100°C for 4 hours. After cooling, the solvent was distilled off under reduced pressure, and isopropyl ether,
Crystals formed by adding ether were collected by filtration and washed with benzene to obtain 4 g of pale yellow powder of 4-(N-3-methylbutyl-N-methylaminomethyl)benzoic acid hydrochloride.

■ Synthesis of 4-hydroxy-4-biphenylcarboxylic acid pentyl ester 4-hydroxy-4-biphenylcarboxylic acid (6.4g
), n-amyl alcohol (22.8 ml) and concentrated sulfuric acid (
1.0 ml) was added dropwise and heated at 95°C for 5 hours. After cooling, the solvent such as amino alcohol was distilled off under reduced pressure, and hexane 3
The crystals formed by adding 0 ml of 4-hydroxy-
4.2 g of pale yellow powder of 4-biphenylcarboxylic acid pentyl ester was obtained.

■ 4-[N-3-methylbutyl-N-
Synthesis process of methylaminomethyl]-benzoic acid-4”-pentyloxycarbonyl-4’-biphenyl ester■
Dissolve the compound obtained in step (1) in 30 ml of dichloromethane, add dicyclohexylcarbodiimide (2.7 g), 3.8 g of the compound obtained in step (2), and 4-pyrrolidinopyridine (0.9 g).
) and stirred overnight at room temperature. The solvent was distilled off under reduced pressure, ethyl acetate (60 ml) was added, and the resulting crystals were filtered off. The obtained crystals were dissolved in dichloromethane and filtered again. The filtrate was washed with saturated sodium hydrogen carbonate (120 ml) and saturated brine (100 ml). Dehydrated over anhydrous magnesium sulfate, concentrated the solvent, added hexane (3 ml), filtered off by-products, and distilled the solvent off under reduced pressure to obtain crude 4-[N-3-methylbutyl-N-methylaminomethyl]-benzoic acid. -4”
5.8 g of -pentyloxycarbonyl-4'-biphenyl ester was obtained. This was subjected to silica gel chromatography, purified twice with ethyl acetate: dichloromethane (1:9) and ethyl acetate: hexane (1:3), recrystallized from hexane, and white needle-like crystals 4-[N-3 -Methylbutyl-N-methylaminomethyl]-benzoic acid-4''-pentyloxycarbonyl-4'-biphenyl ester.
I got 3g.

The structure of the obtained product was confirmed by 1H-NMR and IR. Further, Table 1 shows the results of measuring the phase transition temperature of this substance. The phase transition temperature was determined by visual observation using a polarizing microscope. NMR spectrum (ppm) 0.90, 0.95, 1.30~1.50, 1.52~
1.72, 1.83, 2.22, 2.43, 3.56,
4.35, 7.34, 7.50, 7.68, 7.70,
8.14, 8.19 IR-spectrum (cm-1) 2825, 2750, 1700, 1590, 1440

[
(Examples 2 to 5) In general formula (I), R
Examples 2 to 1 in which 1 and R2 are each a group shown in Table 1
Compounds No. 5 were synthesized in the same manner as in Example 1, respectively. The structures of the obtained compounds were confirmed by 1H-NMR and IR, respectively. NMR spectrum (ppm) 0.90, 0.95, 1.20-1.60*, 1.8
3, 2.22, 2.43 3.56, 4.35, 7.34, 7.50, 7.68,
7.70, 8.14, 8.19 (Note) *The only difference is the height of the peak corresponding to the length of each methylene group; everything else is the same. IR-spectrum (cm-1) 2825, 2750, 1700, 1590, 1440 The phase transition temperatures of these compounds were measured by the method shown in Example 1, and the results are shown in Table 1.

[0054]

[Table 1]

(Examples 6 to 8) The optically active compounds A to C shown below were mixed with the compounds obtained in Examples 2 and 3 above in the proportions shown in Table 2 to prepare liquid crystal compositions.

[Chemical formula 1]

[Case 2]

[Chemical formula 3] This liquid crystal composition was injected into a 3.3 μm thick cell made of a glass plate with a transparent electrode coated with polyimide and subjected to a rubbing treatment, and a rectangular wave voltage (30VP-P, 50Hz) was applied.
When applied, clear switching between light and dark was observed. Table 2 shows the phase transition temperature and response speed.

[0056]

[Table 2]

[0057]

As exemplified above, since the compound of the present invention is a non-optically active compound, it is easy to synthesize, is inexpensive, and exhibits stable liquid crystallinity over an extremely wide temperature range.

Next, since mixing is possible without considering material constants, the degree of freedom in combination is extremely high and compatibility is excellent. Furthermore, when added to a ferroelectric liquid crystal composition, the pitch of the helix can be lengthened.

Furthermore, the high degree of freedom in combination makes it easy to obtain a ferroelectric liquid crystal composition having a preferable liquid crystal temperature range.

[Brief explanation of drawings]

FIG. 1 shows a reaction route of a compound represented by general formula (Ia).

FIG. 2 shows a reaction route of a compound represented by general formula (Ib).

Claims (4)

[Claims] Claim 1: General formula (I) (R1)(R2)N-(CH2)m-Φ-
X-Φ-Φ-(CO)n-OR3


...(I) (in the formula, R1 and R3 are non-optically active alkyl groups having 1 to 18 carbon atoms that may contain a branched chain, a part of which may be substituted with halogen, and R2
is hydrogen, methyl group or ethyl group, Φ is 1,4-phenylene group, X is COO or OCO, m and n are each 0
Or represents 1. ) Amine derivatives represented by Claim 2: General formula (II) (R1)(R2)N-(
CH2)m -Φ-COOH


...(II) (in the formula, R1 is a non-optically active carbon number of 1 to
An alkyl group which may contain 18 branched chains, a part of which may be substituted with halogen, R2 is hydrogen, methyl group or ethyl group, Φ is 1,4-phenylene group, m is 0 or 1. represent. ) or a salt thereof, and general formula (III)
HO-Φ-Φ-(CO)n-OR3


...(III) (In the formula, R3 is a non-optically active alkyl group having 1 to 18 carbon atoms that may contain a branched chain, a part of which may be substituted with halogen, and Φ is 1,4-phenylene) group, n represents 0 or 1.) General formula (I) (R1) (R2) N- (CH2)m -Φ-CO
O-Φ-Φ- (CO)n-OR3


...(Ia) (in the formula, R1 and R3 are non-optically active alkyl groups having 1 to 18 carbon atoms that may contain a branched chain, and a portion thereof may be substituted with halogen, and R2 is hydrogen, methyl or ethyl group, Φ is a 1,4-phenylene group, m and n each represent 0 or 1). Claim 3: General formula (IV) (R1) (
R2)N- (CH2)m -Φ-OH


...(IV) (In the formula, R1 is a non-optically active alkyl group having 1 to 18 carbon atoms that may contain a branched chain, a part of which may be substituted with halogen, and R2 is hydrogen or a methyl group. or ethyl group, Φ is a 1,4-phenylene group, m is 0 or 1) and the compound represented by the general formula (V) HO
OC-Φ-Φ- (CO)n-OR3


...(V) (in the formula, R3 is a non-optically active alkyl group having 1 to 18 carbon atoms that may contain a branched chain, a part of which may be substituted with a halogen, and Φ is 1,4-
A phenylene group, n represents 0 or 1. ) (R1) (R2)N- (CH2)m -Φ-OC
O-Φ-Φ- (CO)n-OR3


...(Ib) (in the formula, R1 and R3 are non-optically active alkyl groups having 1 to 18 carbon atoms that may contain a branched chain, a part of which may be substituted with halogen, and R2 is hydrogen, methyl or ethyl group, Φ is a 1,4-phenylene group, m and n each represent 0 or 1). 4. A liquid crystal device comprising a composition containing the amine derivative according to claim 1 as at least one component.