JPH0782257A - Phenylpyrimidine derivative having optically active 2-substituted alkyl group and liquid crystal composition - Google Patents

Abstract

(57) [Summary] [Structure] General Formula (I) (R ^1: C1-18 alkyl group, X: a single bond or -O
-, M: 0 or 1, ring A and ring B: one is an optionally substituted phenyl group, the other is a pyrimidine ring, and ring C: F
An optionally substituted phenyl group or cyclohexylene group, Y: —OH, —OCH ₃ , —OCF ₂ H, —OCF ₃
Or F, R ^2: C1-18 alkyl, *: containing optically active compound and which is represented by the asymmetric carbon atoms),
In particular, a ferroelectric liquid crystal composition. [Effect] This compound has a low viscosity and is excellent in liquid crystallinity. Therefore, by adding it as a chiral dopant to the host liquid crystal exhibiting the SC phase, a ferroelectric liquid crystal composition capable of high-speed response in a wide temperature range can be obtained without lowering the upper limit temperature of the SC ^* phase. Further, since it is also excellent in chemical stability against water, light, etc., it is useful as a material for a liquid crystal optical switching element for display.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel optically active liquid crystalline compound and a liquid crystal material, and more particularly to a ferroelectric liquid crystal display material having excellent responsiveness and memory property.

[0002]

2. Description of the Related Art Liquid crystal display devices are widely used at present due to their excellent features (low voltage operation, low power consumption, thin display, can be used even in bright places and do not cause eye strain). However, in the TN type, which is the most general display method, the response is extremely slow compared with other light emitting display methods such as CRT, and the display memory (memory effect) is obtained when the applied electric field is cut off. Therefore, there are many restrictions on the application to moving screens such as an optical shutter that requires high-speed response, a printer head, or a television that requires time-division driving, and it cannot be said that it is a suitable display method.

Recently, a display method using a ferroelectric liquid crystal has been reported, and according to this, a TN type liquid crystal display of 100-1 is used.
Since a high-speed response of 000 times and a memory effect can be obtained, it is expected as a next-generation liquid crystal display device, and research and development are being actively conducted at present.

The liquid crystal phase of the ferroelectric liquid crystal belongs to the tilt type chiral smectic phase, but the chiral smectic C (hereinafter abbreviated as SC ^* ) phase has the lowest viscosity and is most desirable. A large number of liquid crystal compounds exhibiting the SC ^* phase have already been synthesized and studied, but the following conditions for use as a ferroelectric liquid crystal device, namely, (a) exhibiting the SC ^* phase in a wide temperature range including room temperature, (B) In order to obtain good orientation, the SC ^* phase has an appropriate phase series on the high temperature side, and its helical pitch is large, (c) it has an appropriate tilt angle, and (d) the viscosity is Small things,
No compound is known that alone satisfies (e) sufficient polarization, and (f) high-speed response. Therefore, it is necessary to mix several or more compounds and use them as a liquid crystal composition showing an SC ^* phase (hereinafter, abbreviated as SC ^* liquid crystal composition).

As a method for preparing the SC ^* liquid crystal composition, a matrix liquid crystal (hereinafter abbreviated as SC matrix liquid crystal) composed of an achiral compound and showing a smectic C (hereinafter abbreviated as SC) phase is prepared from an optically active compound. The method of adding a chiral dopant is most general because a composition having a lower viscosity can be obtained and a high-speed response is possible.

The compound used as the chiral dopant is
Alone, it is not always necessary to show the SC ^* phase or even the liquid crystal phase, but by adding it as a chiral dopant, it induces a certain degree of spontaneous polarization in the liquid crystal composition, and has a sufficiently large helical pitch. It is necessary to indicate

It is well known that the response time (τ) of a ferroelectric liquid crystal is proportional to its viscosity and inversely proportional to its spontaneous polarization. According to this, in order to shorten the response time, the viscosity should be lowered and the spontaneous polarization should be increased. However, if the spontaneous polarization is too large, it adversely affects the switching characteristics such as the memory property and increases the viscosity of the composition. Therefore, it is desirable that the spontaneous polarization be as small as possible. Therefore, it is necessary to prevent the viscosity of the composition from increasing by minimizing the viscosity of the chiral dopant itself.

Low-viscosity optically active compounds have been synthesized so far. However, when such a low-viscosity optically active compound is added so that a high-speed response is possible, it often has a bad influence on the temperature range of the liquid crystal phase of the composition, the phase series, or the like.

[0009]

The problem to be solved by the present invention is to provide a low-viscosity optically active compound capable of high-speed response by adding it to a host liquid crystal as a chiral dopant, and to use it. Another object of the present invention is to provide a ferroelectric liquid crystal display material having high-speed response.

[0010]

In order to solve the above-mentioned problems, the present invention has the general formula (I)

[0011]

[Chemical 2]

(Where R¹Is an optionally substituted carbon
Represents an alkyl group having 1 to 18 atoms, especially carbon atoms
A linear alkyl group of the number 6 to 14 is preferable. X is a single bond
Or represents -O-. m represents 0 or 1, but especially 0
Is preferred. Ring C is substituted by one or two fluorine atoms.
Optionally substituted 1,4-phenylene group or trans
It represents a -1,4-cyclohexylene group. Ring A and Ring B
Of which one is substituted by one or two fluorine atoms
1,4-phenylene group which may be substituted,
4-phenylene group is preferred, the other is pyrimidine-2,
Represents a 5-diyl group. Y is -OH, -OCH₃, -O
CF₂H, -OCF₃Or represents a fluorine atom, but --OH
Alternatively, a fluorine atom is preferable. R²Has 1 to 18 carbon atoms
Represents an alkyl group of, but is especially a straight chain having 1 to 10 carbon atoms.
A chain alkyl group is preferred. Also, ^*Its carbon is optical
Represents an active asymmetric carbon. ) Light
Phenylpyrimidimines with 2-Substituted Alkyl
To provide a derivative thereof.

In the general formula (I), many structures are possible as the central skeleton (core) by combining m, ring A, ring B and ring C. Among them, the following general formula (I
Compounds of a) to (Id) are preferred, especially those of general formula (I
The compounds of a) and (Ib) are preferred.

[0014]

[Chemical 3]

(Wherein R ¹ , X, Y, R ² and * have the same meanings as in formula (I).) The present invention also provides the optically active phenyl represented by formula (I). Provided is a liquid crystal composition containing a pyrimidine derivative.

The liquid crystal composition of the present invention has the above general formula (I).
Which contains at least one of the phenylpyrimidine derivatives described above as a constituent component. In particular, for displaying a ferroelectric liquid crystal, the main component SC matrix liquid crystal has the above general formula (I).
An SC ^* liquid crystal composition obtained by adding at least one of the above compounds as a part or all of the chiral dopant is desirable. Alternatively, by adding a small amount of the compound of the general formula (I) of the present invention to a nematic liquid crystal, a so-called reverse domain can be prevented as a TN type liquid crystal, or STN can be used.
It can be used for applications such as type liquid crystals. For such use, in the general formula (I), R ¹ and R ² have 1 to 1 carbon atoms.
Compounds which are linear alkyl groups of 7 are preferred.

The compound of the general formula (I) of the present invention can be produced from the corresponding dithiane derivative according to the following production method. That is, the general formula (II)

[0018]

[Chemical 4]

The 1,3-dithiane derivative represented by the formula (wherein R ¹ , X, m, ring A, ring B and ring C have the same meanings as in formula (I)) with a strong base. age,

[0020]

Embedded image By reacting with an aldehyde represented by R ² CHO (wherein R ² has the same meaning as in the general formula (I)), the compound represented by the general formula (III)

[0021]

[Chemical 6]

(Wherein R ¹ , X, m, ring A, ring B, ring C, R ² and ^* have the same meanings as in formula (I)). A dithiane derivative can be obtained. This general formula (III)
The compound of formula (I) having a 2-hydroxyalkyl group is obtained by reductively desulfurizing the compound of
The compound of the following general formula (Ip) in which Y in the general formula (I) is —OH is obtained by optically resolving the racemic compound of Can be obtained.

[0023]

[Chemical 7]

(In the formula, R ¹ , X, m, ring A, ring B, ring C, R ² and * have the same meanings as in formula (I).) Further, this optical resolution is relatively difficult. In such a case, it can be easily obtained by acetylating the hydroxyl group for optical resolution and then hydrolyzing the acetyl group.

Various compounds of the general formula (I) of the present invention can be obtained by the method described below.

[0026]

[Chemical 8]

(In the formula, R ¹ , X, m, ring A, ring B, ring C, R ² and * have the same meanings as in formula (I).) By reacting the compound with a fluorinating agent such as dimethylaminosulfur trifluoride (DAST), general formula (Iq) in which Y in general formula (I) is a fluorine atom can be obtained.

Further, the compound of the general formula (Ip) is used as a base compound.
And methylating agents such as methyl iodide and dimethylsulfate.
By reacting, Y in the general formula (I) is -O.
CH ₃It is possible to obtain a compound of general formula (Ir)
Wear.

Further, by converting the compound of the general formula (Ip) into a dithiocarbonate and then reacting it with a fluorinating agent, Y in the general formula (I) is —OCF _3; ).

Further, by converting the compound of the general formula (Ip) to a formate ester and then reacting it with a fluorinating agent, the general formula (I-t) in which Y in the general formula (I) is —OCF ₂ H. ).

[0031]

[Chemical 9]

(In the formula, R ¹ , X, m, ring A, ring B and ring C have the same meanings as in formula (I).) 1 of formula (II) used as an intermediate here. , 3-dithiane derivatives are the following when Ring B is a pyrimidine ring:
It can be obtained by reacting the corresponding formylpyrimidine derivative of the general formula (IV) with 1,3-propanedithiol.

[0033]

[Chemical 10]

(In the formula, R ¹ , X, m, ring A, ring B and ring C have the same meanings as in formula (I).) Further, when ring A is a pyrimidine ring, Formula (V
It can be obtained by reacting an amidine hydrochloride which is a dithiane derivative of a) with an acrolein derivative of the general formula (VIb).

[0035]

[Chemical 11]

(In the formula, R ¹ , X, m, ring A, ring B and ring C have the same meanings as in formula (I).) Alternatively, an acrolein derivative which is a dithiane derivative of formula (Vb). It can be obtained by reacting with an amidine hydrochloride of general formula (VIa).

The compounds of the general formula (I) of the present invention can be obtained as described above, and the specific compounds belonging to these compounds have a phase transition temperature such as a melting point and an infrared absorption spectrum (IR). , Nuclear magnetic resonance spectrum (NMR), mass spectrum (MS) and the like.

Typical examples of the compounds of formula (I) thus obtained are shown in Table 1.

[0039]

[Table 1]

(In the table, Cr represents a crystalline phase, SX represents a chiral smectic phase with unidentified properties, SB represents a smectic B phase, SA represents a smectic A phase, I represents an isotropic liquid phase, and [α] _D represents the optical rotation at 20 ° C, and the phase transition temperature represents ° C.) From Table 1, among the compounds of the general formula (I), particularly the compound of the general formula (Ia-
Most of the compounds of q) or (Ib-q) show a chiral smectic phase up to a relatively high temperature range. Further, among the compounds of general formula (I), there are some compounds which do not exhibit a liquid crystal phase, but rather than using the compound of general formula (I) alone,
Since it is desirable to use it as a SC ^* liquid crystal composition by adding it as a chiral dopant to the host liquid crystal exhibiting the SC phase, there is no practical problem.

The effects of the compounds of the general formula (I) of the present invention are shown below, as shown in the examples below. Phenylpyrimidine-based host liquid crystal (H-1) having an upper limit temperature of SC phase of 55.5 ° C

[0042]

[Chemical 12]

(In the formula, "%" represents "% by weight".)
Was prepared. 90% by weight of this host liquid crystal (A) and a compound 10 of formula (Ia-q-1) exhibiting a chiral smectic phase.
When a liquid crystal composition containing 1% by weight was prepared, the maximum liquid crystal composition SC ^* phase maximum temperature was 58 ° C. Similarly, 80% by weight of the base liquid crystal (H-1) and the formula (Ia)
A liquid crystal composition comprising 20% by weight of the compound of −q-1) is
The maximum temperature of the SC ^* phase is 61.5 ° C, 70% by weight of the host liquid crystal (A) and the compound 30 of the formula (Ia-q-1).
The liquid crystal composition composed of wt% has a maximum temperature of the SC ^* phase of 6
It is 4.5 ° C., which shows that the temperature range tends to be expanded.

Further, 5% by weight of the compound of the formula (1a-p-1) which does not show a chiral smectic phase but shows a non-tilt type smectic phase such as SB phase or SA phase.
When a liquid crystal composition containing 95% by weight of the host liquid crystal (H-1) was prepared, the maximum temperature of the SC ^* phase of the obtained SC ^* composition was 55.5 ° C., which was almost unchanged. Also,
5% by weight of a compound of formula (Ib-q-1) showing no liquid crystal phase
When a liquid crystal composition containing 95% by weight of the base liquid crystal (A) was prepared, the maximum temperature of the SC ^* phase of the obtained SC ^* composition was 49.5 ° C., which was a slight decrease. From the above, when the compound of the general formula (I) of the present invention is added to the host liquid crystal exhibiting the SC phase, the temperature range of the SC ^* phase of the obtained SC ^* liquid crystal composition is not narrowed but rather expanded. Understand that they have a tendency to

Further, by adding the compound of the general formula (I) to the host liquid crystal, an SC ^* liquid crystal composition capable of high-speed response can be obtained. For example, the above formula (Ia-q-
20% by weight of the compound of 1) and the host liquid crystal (H-1) 80
The SC ^* liquid crystal composition composed of wt% showed a high-speed response of 200 μs, although the spontaneous polarization at 25 ° C. was as small as 0.1 nC / cm ² or less. From this, it can be understood that the viscosity of the compound of the general formula (I) is very small.

The SC compound used in the host liquid crystal to which the compound of the general formula (I) of the present invention is added as a chiral dopant is, for example, the following general formula (A).

[0047]

[Chemical 13]

(In the formula, R ^a and R ^b are linear or branched alkyl groups, alkoxy groups, alkoxycarbonyl groups,
It represents an alkanoyloxy group or an alkoxycarbonyloxy group, which may be the same or different. ) Phenyl benzoate compounds represented by,
General formula (B)

[0049]

[Chemical 14]

A phenylpyrimidine compound represented by the formula (wherein R ^a and R ^b have the same meanings as in formula (A)) can be given. In addition, the general formula (C) including the general formulas (A) and (B)

[0051]

[Chemical 15]

(In the formula, R ^a and R ^b have the same meanings as in the general formula (A), and the ring L and the ring M are 1, 4 respectively.
-Phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, pyridazine-3,6
Represents a -diyl group, a 1,3-dioxane-2,5-diyl group or a halogen-substituted product thereof, which may be the same or different, and Z ^a is -COO-, -O.
_{CO -, - CH 2 O -} , - OCH 2 -, - CH 2 CH 2 -,
-C = C- or represents a single bond. The compound represented by () can be used for the same purpose.

For the purpose of expanding the temperature range of the SC phase to a high temperature range, the general formula (D)

[0054]

[Chemical 16]

(In the formula, R^aAnd R^bIs in general formula (A)
And ring L, ring M and ring N are the same as
It has the same meaning as ring L and ring M in formula (C),
May be the same or different, Z^aAnd Z^bIs
Z of the general formula (C) ^aHas the same meaning as
They may be the same or different from each other. )
It is possible to use a three-ring compound.

It is effective that these compounds are mixed and used as an SC liquid crystal composition, but it is only necessary that the composition show the SC phase, and it is not always necessary for each compound to show the SC phase. .

By adding the compound of the general formula (I) of the present invention and, if necessary, other optically active compound to the thus obtained SC liquid crystal composition as a chiral dopant, SC ^{* in a} wide temperature range including room temperature ^. A liquid crystal composition exhibiting a phase can be easily obtained.

The compound of general formula (I) of the present invention is prepared by
SC obtained by adding to C matrix liquid crystal ^*The liquid crystal composition is 2
As a thin film of about 1 to 20 μm between transparent glass electrodes
By enclosing it, it can be used as a display cell. Good
Uniformly oriented monods for good contrast
Need to be main. Many to obtain good orientation
However, as a liquid crystal material, the high temperature side has been tried.
To Phase I-N^*(Chiral nematic) Phase-SA (Smek
Tick A) phase-SC^*Phase or I phase-SA phase-SC^*Phase of phase
Shows the sequence, N^*Phase and SC^*Large spiral pitch in phase
You need a threshold. To increase the spiral pitch,
Generally, an appropriate amount of chiral compounds with opposite twist directions are mixed.
Although the method of combining is used, the general formula (I) of the present invention is used.
In the compound of 1, the compound obtained by selecting the substituent Y
The relationship between the direction of the spiral pitch induced by
Since it is different, it can be adjusted by using only the compound of general formula (I).
Is possible.

For example, when Y is OH, the polarity of spontaneous polarization is + when the direction of the spiral pitch is left,
Whereas Y is F when Y is F, it is − when Y is F and + when Y is F.

The compound of the general formula (I) of the present invention may be added in an amount of 1% by weight or more in the obtained SC ^* liquid crystal composition, and when other optically active compound is also used as a chiral dopant. It may be 1% by weight or less.

[0061]

EXAMPLES The present invention will be specifically described below with reference to examples, but the gist and the scope of application of the present invention are not limited to these examples.

The phase transition temperature was measured by using a polarizing microscope equipped with a temperature adjusting stage and a differential scanning calorimeter (DSC). The structure of the compound is NMR, IR,
Confirmed by MS and elemental analysis. (Ne in IR
(at) indicates the measurement by the liquid film, and (KBr) indicates the measurement by the tablet molding. CDCl _{3 in} NMR represents a solvent, s is a singlet, d is a doublet, t is a triplet, quin.
tet represents a quintuplet, m represents a multiplet, and, for example, d
t represents the doublet triplet and broad represents the broad absorption. M ^{+ in} MS represents the parent peak, ()
The numerical value inside represents the relative intensity of the peak. All "%" in the composition represent "% by weight".

Reference Example 1 5-Formyl-2- (4-
Synthesis of decyloxyphenyl) pyrimidine

[0064]

[Chemical 17]

A solution of 1.0 g of 4-decyloxybenzamidine hydrochloride and 0.9 g of 3- (N, N-dimethylamino) -2-formylacrolein in 25 ml of methanol was prepared from 1 g of sodium and 20 ml of methanol. -Methanol solution was added and heated to reflux for 5 hours. After concentration under reduced pressure, 2M hydrochloric acid was added to the obtained residue, the reaction product was extracted with ethyl acetate, and then separated and purified using column chromatography (Wakogel C-200, hexane / ethyl acetate = 9/1). , 5-formyl-2- (4-decyloxyphenyl) pyrimidine (1.06 g, yield: 97%) was obtained. Colorless needle crystal melting point 110 ° C IR (KBr) 2930, 2850, 1680, 15
85, 1435, 1260, 1170, 1010, 85
0,800,730 cm ^{-1 1} H NMR (CDCl ₃ ) δ 0.88 (t, J =
6.8 Hz, 3 H), 1.24 to 1.72 (m, 12
H), 1.42 to 1.52 (m, 2H), 1.77 to
1.87 (m, 2H), 4.05 (t, J = 6.6H
z, 2H), 7.01 (d, J = 9.0Hz, 2H),
8.50 (d, J = 9.0 Hz, 2H), 9.15
(S, 2H), 10.10 (s, 1H) MS m / z 340 (M ⁺ , 21), 200 (10
0), 43 (30) Elemental analysis: Calculated as C ₂₁ H ₂₈ N ₂ O ₂ C: 74.08%; H, 8.29%; N, 8.
23% Found: C, 73.90%; H, 8.23%; N, 8.
10%

Reference Example 2 Synthesis of 2- [2- (4-decyloxyphenyl) pyrimidin-5-yl)]-1,3-dithiane

[0067]

[Chemical 18]

5-Formyl-2 obtained in Reference Example 1 above
2.5 g of-(4-decyloxyphenyl) pyrimidine,
1.8 g of propanedithiol and 30 ml of trimethylsilyl polyphosphate (PPSE) -dichloromethane solution were stirred at room temperature for 9 hours. After completion of the reaction, 50 ml of saturated aqueous sodium hydrogen carbonate solution was added, and the reaction product was extracted with ethyl acetate. The extract was concentrated and then recrystallized from a hexane / ethyl acetate (15/1) mixture to give 2- [2- (4
-Decyloxyphenyl) pyrimidin-5-yl)]-
2.7 g (yield: 85%) of 1,3-dithiane was obtained. Colorless plate crystal melting point 106 ° C. IR (KBr) 2930,2850,1605,15
80, 1430, 1265, 1165, 800 cm ^{-1 1} H NMR (CDCl ₃ ) δ 0.88 (t, J =
6.9 Hz, 3H), 1.24 to 1.72 (m, 12
H), 1.42 to 1.52 (m, 2H), 1.77 to
1.87 (m, 2H), 1.92 to 2.04 (m, 1
H), 2.17-2.27 (m, 1H), 2.93-
3.01 (m, 2H), 3.03 to 3.13 (m, 2)
H), 4.02 (t, J = 6.6 Hz, 2H), 5.1
7 (s, 1H), 6.98 (d, J = 9.0Hz, 2
H), 8.37 (d, J = 9.0 Hz, 2H), 9.8
3 (s, 2H) MS m / z 431 (M ⁺⁺ 1,26), 430
(M ⁺ , 89), 356 (48), 216 (100),
120 (22), 119 (42), 57 (25), 55
(20), 43 (64), 41 (41) Elemental analysis: Calculated as C ₂₂ H ₃₀ N ₂ OS ₂ : C, 66.93%; H, 7.96%; N, 6.
50%; S, 14.89% Found: C, 66.70%; H, 8.02%; N, 6.
62%; S, 15.08%

(Example 1) (-)-2- (4-decyloxyphenyl) -5- (2-hydroxyundecyl)
Pyrimidine (compound of (1a-p-1)) and (+)-
Synthesis of 2- (4-decyloxyphenyl) -5- (2-hydroxyundecyl) pyrimidine (compound of (1a-p-2))

[0070]

[Chemical 19]

(1-a) Synthesis of 2- [2- (4-decyloxyphenyl) pyrimidin-5-yl)]-2- (1-hydroxydecyl) -1,3-dithiane Diisopropylamine 56 mg in THF 10 ml solution To the above, 0.3 ml of 1.6 M butyllithium-hexane solution was added at −78 ° C. and stirred for 30 minutes. 2 in this reaction solution
-[2- (4-decyloxyphenyl) pyrimidine-5
-Yl)]-1,3-dithiane 200 mg THF 5 m
1 solution was added, and the mixture was stirred at −78 ° C. for 15 minutes, and then 87 mg of decanal in 5 ml of THF was added and stirred for 2 hours. The reaction solution was treated with saturated saline, the reaction product was extracted with ethyl acetate, the extract was concentrated, and the obtained residue was subjected to column chromatography (Wakogel C-300, hexane / ethyl acetate 5/1). Purified using
[2- (4-decyloxyphenyl) pyrimidine-5-
Yl)]-2- (1-hydroxydecyl) -1,3-dithiane (189 mg, yield: 70%) was obtained.

Colorless viscous oily substance IR (neat) 3407, 2924, 2855, 1
607, 1574, 1427, 1254, 1169, 1
082,847,801 cm ^{-1 1} H NMR (CDCl ₃ ) δ 0.86 (t, J =
6.9 Hz, 3H), 0.89 (t, J = 6.9, H
z, 3H), 1.21-1.52 (m, 30H), 1.
78-1.85 (m, 2H), 1.92-2.02
(M, 2H), 2.35 (bd, J = 5.2 Hz, 1
H), 2.62 to 2.81 (m, 4H), 3.90.
(T, J = 5.2 Hz, 1H), 4.04 (t, J =
6.6Hz, 2H), 7.00 (d, J = 9.0Hz,
2H), 8.42 (d, J = 9.0Hz, 2H), 9.
23 (s, 2H) MS m / z 586 (M ⁺ , 0.1), 569 (4
2), 431 (33), 430 (100), 289 (1
5), 215 (20), 69 (22), 43 (99),
41 (62) Elemental _{analysis: C 34 H 54 N 2 O} 2 S 2 Calculated: C, 69.58%; H, 9.27%; N, 4.
77%; S, 10.93% Found: C, 69.49%; H, 9.04%; N, 4.
61%; S, 10.82%

(1-b) (-)-2- (4-decyloxyphenyl) -5- (2-hydroxyundecyl) pyrimidine and (+)-2- (4-decyloxyphenyl) -5- ( Synthesis of 2-hydroxyundecyl) pyrimidine 2- [2- (4-decyloxyphenyl) pyrimidin-5-yl)]-2- (1-hydroxydecyl) -1, obtained in (1-a) above. To a solution of 189 mg of 3-dithiane in 10 ml of acetone, 10 ml of a Raney nickel (W-4) ethanol suspension was added, and the mixture was heated under reflux for 30 minutes. The reaction solution was filtered through Celite, the filtrate was concentrated, and the obtained residue was subjected to column chromatography (Wakogel C-30
0, hexane / ethyl acetate = 5/1) and purified to give 2- (4-decyloxyphenyl) -5- (2-hydroxyundecyl) pyrimidine 140 mg (yield: 9
1%) was obtained. Furthermore, high performance liquid chromatography (Daicel Corporation, CHIRALCELOD, 2 cm ID)
25 cm) to separate the two optical isomers,
66 mg of 2- (4-decyloxyphenyl) -5- (2-hydroxyundecyl) pyrimidine (yield: 43
%) And (+)-2- (4-decyloxyphenyl)-
74 mg of 5- (2-hydroxyundecyl) pyrimidine
(Yield: 48%) was obtained.

Colorless Needle Crystal Phase Transition Temperature (° C.) Cr87 (SB82) SA11
4 I [α] _D ²⁰ -2.4 ° (c = 1.1, CHCl ₃ ) and + 2.9 ° (c = 0.98, CHCl ₃ ) IR (KBr) 3358, 2924, 2851, 16
11, 1591, 1543, 1433, 1252, 11
_{^{67,793cm -1 1 H NMR (CDCl 3}} ) δ 0.88 (t, J =
6.9 Hz, 3 H), 0.89 (t, J = 7.0 Hz,
3H), 1.27 to 1.57 (m, 30H), 1.67
(D, J = 4.6 Hz, 1H), 1.77 to 1.84
(M, 2H), 2.66 (dd.J = 14.0, and
7.9 Hz, 1 H), 2.78 (dd, J = 14.0,
and 4.1 Hz, 1H), 3.79 to 3.84 (m,
1H), 4.03 (t, J = 6.6Hz, 2H), 6.
98 (d, J = 9.0 Hz, 2H), 8.34 (d, J
= 9.0 Hz, 2H), 8.61 (s, 2H) MS m / z 482 (M +, 23), 346 (2
5), 187 (14), 186 (97), 185 (3
3), 83 (24), 69 (34), 43 (100),
41 (64) Elemental _{analysis: C 31 H 50 N 2 O} 2 Calculated: C, 77.13%; H, 10.44%; N,
5.80% Found: C, 76.94%; H, 10.36%; N,
5.77%

Example 2 (-)-2- (4-decyloxyphenyl) -5- (2-hydroxydecyl) pyrimidine (compound of (1a-p-3)) and (+)-2-
Synthesis of (4-decyloxyphenyl) -5- (2-hydroxydecyl) pyrimidine ((1a-p-4 compound) In Example 1, the same as Example 1 except that nonanal was used instead of decanal. Then, (-)-2- (4
-Decyloxyphenyl) -5- (2-hydroxydecyl) pyrimidine and (+)-2- (4-decyloxyphenyl) -5- (2-hydroxydecyl) pyrimidine were obtained.

Colorless Needle Crystal Phase Transition Temperature (° C.) Cr86 (SB67) SA11
3 I [α] _D ²⁰ −2.1 ° (c = 1.01, CHCl ₃ ) and + 2.8 ° (c = 0.93, CHCl ₃ ) IR (KBr) 3355, 2924, 2853, 16
01, 1593, 1545, 1433, 1256, 11
_{^{67,793cm -1 1 H NMR (CDCl 3}} ) δ 0.88 (t, J =
6.0 Hz, 3 H), 0.88 (t, J = 5.6 Hz,
3H), 1.27 to 1.56 (m, 28H), 1.67
(D, J = 4.4 Hz, 1H), 1.78 to 1.85
(M, 2H), 2.66 (dd.J = 14.0, and
8.0 Hz, 1 H), 2.78 (dd, J = 14.0,
and 4.2 Hz, 1H), 3.79 to 3.85 (m,
1H), 4.03 (t, J = 6.6Hz, 2H), 6.
98 (d, J = 9.0 Hz, 2H), 8.34 (d, J
= 9.0 Hz, 2H), 8.61 (s, 2H) MS m / z 468 (M ⁺ , 23), 326 (2
4), 187 (13), 186 (100), 185 (3
4), 158 (12), 83 (21), 69 (53),
43 (99), 41 (73) High Resolution _{MS: C 30 H 48 N 2} O 2 Calculated: 468.3712 Found: 468.3710

Example 3 (−)-2- (4-decyloxyphenyl) -5- (2-hydroxynonyl) pyrimidine (compound of (1a-p-5)) and (+)-2-
Synthesis of (4-decyloxyphenyl) -5- (2-hydroxynonyl) pyrimidine ((compound of 1a-p-6)) In Example 1, except that octanal was used instead of decanal. Then, (-)-2-
(4-decyloxyphenyl) -5- (2-hydroxynonyl) pyrimidine and (+)-2- (4-decyloxyphenyl) -5- (2-hydroxynonyl) pyrimidine were obtained.

Colorless Needle Crystal Phase Transition Temperature Cr81 SA115 I [α] _D ²⁰ −7.0 ° (c = 0.92, CHCl ₃ ) and + 6.7 ° (c = 0.86, CHCl ₃ ) IR ( KBr) 3353, 2957, 2924, 16
09, 1591, 1433, 1252, 1167, 79
_{^{3cm -1 1 H NMR (CDCl 3}} ) δ 0.88 (t, J =
7.0 Hz, 3 H), 0.88 (t, J = 6.7 Hz,
3H), 1.28 to 1.59 (m, 27H), 1.78.
˜1.85 (m, 2H), 2.67 (dd.J = 14.
1, and 7.9 Hz, 1 H), 2.79 (dd.J =
14.1, and 4.2 Hz, 1H), 3.80-3.
86 (m, 1H), 4.03 (t, J = 6.6Hz, 2
H), 6.98 (d, J = 9.0 Hz, 2H), 8.3
5 (d, J = 9.0 Hz, 2H), 8.62 (s, 2
H) MS m / z 454 (M ⁺ , 80), 326 (4
4), 187 (13), 186 (100), 185 (2
8), 83 (7), 69 (28), 43 (40), 41
(24) Elemental _{analysis: C 30 H 48 N 2 O} 2 Calculated: C, 76.61%; H, 10.20%; N,
6.16% Found: C, 76.41%; H, 10.14%; N,
6.11%

Reference Example 3 Synthesis of 2- [4- (5-decylpyrimidin-2-yl) phenyl] -1,3-dithiane

[0080]

[Chemical 20]

4-Cyanobenzaldehyde (10 g), propanedithiol (10 g) and PPSE-dichloromethane solution (60 ml) were stirred at room temperature for 10 hours. 200 ml of saturated aqueous sodium hydrogen carbonate solution was added, and the reaction product was extracted with 200 ml of ether and 100 ml of ethyl acetate. After concentrating the extract, hexane / ethyl acetate (9/1) mixed solvent was recrystallized to give 2- (4-cyanophenyl) -1,3-
14.9 g (yield: 88%) of dithiane was obtained. Colorless needles melting point 112 ° C

The obtained 2- (4-cyanophenyl)-
A mixed solution of 10 g of 1,3-dithiane, 3.5 g of ethanol, 40 ml of dichloromethane and 80 ml of ether was stirred under a hydrogen chloride atmosphere at room temperature for 5 days. After concentration under reduced pressure,
100 ml of methanol was added to the obtained residue, and the mixture was stirred at room temperature under an ammonia gas atmosphere for 3 days. After concentration under reduced pressure, 100 ml of ether was added, the white precipitate was filtered off, and dried to obtain 13.7 g of 4- (2,6-dithiocyclohexyl) benzamidine hydrochloride. To 2.2 g of this 4- (2,6-dithiocyclohexyl) benzamidine hydrochloride,
1- (N, N-dimethylamino) -2-formyl-1-
Dodecene (2.5 g) and methanol (20 ml) were added, a sodium methoxide-methanol solution prepared from sodium (1 g) and methanol (20 ml) was added, and the mixture was heated under reflux for 5 hours. After concentration under reduced pressure, water was added to the obtained residue, the reaction product was extracted with ethyl acetate, and then silica gel column chromatography (hexane / ethyl acetate = 6/1).
Separated and purified using, and recrystallized from hexane,
2- [4- (5-decylpyrimidin-2-yl) phenyl] -1,3-dithiane (1.6 g, yield: 47%) was obtained.

Colorless needles melting point 84 ° C. IR (KBr) 2924,2851,1433,12
_{^{73,762cm -1 1 H NMR (CDCl 3}} ) δ 0.88 (t, J =
7.0 Hz, 3 H), 1.26 to 1.35 (m, 15
H), 1.61 to 1.69 (m, 2H), 1.91
2.02 (m, 1H), 2.16 to 2.23 (m, 1
H), 2.62 (t, J = 7.7 Hz, 2H), 2.9
4 (dt, J = 14 and 3.5 Hz, 2H), 3.0
9 (dt, J = 14 and 2.4 Hz, 2H), 7.5
9 (d, J = 8.4 Hz, 2H), 8.39 (d, J =
8.4 Hz, 2H), 8.61 (s, 2H) MS m /
z 415 (M ⁺ +1,30), 414 (M ⁺ , 10)
0), 349 (58), 340 (82), 227 (2
9), 214 (28), 213 (23), 105 (1
1), 43 (27) Elemental analysis: C ₂₄ H ₃₄ N ₂ S ₂ Calculated value: C, 69.52%; H, 8.26%; N, 6.
76%; S, 15.47% Found: C, 69.61%; H, 8.26%; N, 6.
93%; S, 15.56%

(Example 4) (-)-5-decyl-2-
[4- (2-hydroxynonyl) phenyl] pyrimidine (a compound of (1b-p-1)) and (+)-5-decyl-2- [4- (2-hydroxynonyl) phenyl] pyrimidine ((1b- Compound of p-2))

[0085]

[Chemical 21]

(4-a) Synthesis of 2- [4- (5-decylpyrimidin) -2-yl-phenyl] -2- (1-hydroxyoctyl) -1,3-dithiane Diisopropylamine 73 mg in THF 3 ml solution. ,
1.6M butyllithium-hexane solution at -78 ° C.
5 ml was added and stirred for 30 minutes. 2-in this reaction liquid
[4- (5-decylpyrimidin) -2-yl) phenyl] -1,3-dithiane 250 mg, octanal 92
A solution of 5 mg of THF in 5 ml was added dropwise over 15 minutes, and -7
Stirred at 8 ° C. for 1 hour. The reaction solution was treated with saturated saline,
The reaction product was extracted with ethyl acetate, the extract was concentrated, and the obtained residue was purified by column chromatography (hexane / ethyl acetate = 10/1) to give 2- [4
-(5-decylpyrimidin) -2-yl) phenyl]-
2- (1-hydroxyoctyl) -1,3-dithiane 2
25 mg (yield: 69%) was obtained.

Colorless viscous oily substance IR (neat) 3437, 2926, 2855, 1
728, 1588, 1541, 1431, 1074, 8
_{^{62,795cm -1 1 H NMR (CDCl 3}} ) δ 0.83 (t, J =
7.0 Hz, 3 H), 0.88 (t, J = 6.7 Hz,
3H), 1.19 to 1.59 (m, 26H), 1.65
˜1.70 (m, 2H), 1.93-1.99 (m, 2
H), 2.16 (d, J = 5.6 Hz, 1H), 2.6
4 (t, J = 7.7 Hz, 2H), 2.68 to 2.78
(M, 4H), 3.83 to 3.86 (m, 1H), 8.
08 (d, J = 8.8 Hz, 2H), 8.42 (d, J
= 8.8 Hz, 2H), 8.64 (s, 2H) MS m / z 542 (M ⁺ , 0.4), 524
(3), 413 (100), 339 (23), 212
(12), 69 (19), 43 (38) Elemental analysis: Calculated as C ₃₂ H ₅₀ N ₂ O ₂ S ₂ C: 70.80%; H, 9.28%; N, 5.
16%; S, 11.81% Found: C, 70.76%; H, 9.18%; N, 5.
03%; S, 11.64%

(4-b) (+)-2- [4- (2-acetyloxynonyl) phenyl] -5-decylpyrimidine and (-)-2- [4- (2-acetyloxynonyl) phenyl] Synthesis of 5-decylpyrimidine 2- [4- (5-decylpyrimidin) -2-yl) phenyl] -2- (1-hydroxyoctyl) -1,3-dithiane 200 mg in a solution of Raney nickel (W- 4) Add 15 ml of ethanol suspension and add 30
Heated to reflux for minutes. The reaction solution was filtered through Celite, the filtrate was concentrated, and the obtained residue was subjected to column chromatography (Wakogel C-300, hexane / ethyl acetate = 5 /
The product was purified using 1) to obtain 130 mg of 5-decyl-2- [4- (2-hydroxynonyl) phenyl] pyrimidine (yield: 80%). This was dissolved in 15 ml of dichloromethane, 59 mg of acetic anhydride and 15 ml of pyridine were added at room temperature, and the mixture was stirred for 13 hours. After the reaction solution was concentrated under reduced pressure, the obtained residue was washed with dilute hydrochloric acid and then saturated aqueous sodium hydrogen carbonate solution, and the reaction product was extracted with ether,
After concentrating the extract, the obtained residue was purified by column chromatography (hexane / ethyl acetate = 10/1), 2- [4- (2-acetyloxynonyl) phenyl] -5-decylpyrimidine. 105 mg (yield: 95
%) Was obtained. High performance liquid chromatography (Daicel, CHIRALCEL OD, 2 cm ID × 2)
5 cm) to separate the two optical isomers, (+)-
2- [4- (2-acetyloxynonyl) phenyl]-
50 mg of 5-decylpyrimidine (yield: 45%) and 48 mg of (-)-2- [4- (2-acetyloxynonyl) phenyl] -5-decylpyrimidine (yield: 44)
%) Was obtained.

Colorless viscous oily substance [α] _D ²⁰ + 4.4 ° (c = 0.90, CHCl ₃ ) and −3.8 ° (c = 0.64, CHCl ₃ ) IR (KBr) 2926, 2855, 1740, 15
88,1543,1431,1375,1240,10
_{^{20,793cm -1 1 H NMR (CDCl 3}} ) δ 0.87 (t, J =
7.0Hz, 3H), 0.88 (t, J = 6.9Hz,
3H), 1.24 to 1.33 (m, 24H), 1.53
~ 1.58 (m, 2H), 1.61 to 1.67 (m, 2
H), 1.99 (s, 3H), 2.62 (t, J = 7.
6Hz, 2H), 2.90 (ddd, J = 20, 14a
nd 6.4 Hz, 2H), 5.11 (quintet,
J = 6.4 Hz, 1H), 7.31 (d, J = 8.4H
z, 2H), 8.32 (d, J = 8.4Hz, 2H),
9.60 (s, 2H) MS m / z 481 (M ⁺ +1, 2), 420 (3
1), 335 (16), 310 (16), 149 (1
2), 69 (22), 57 (59), 55 (40), 4
3 (100), 41 (63) Elemental analysis: Calculated as C ₃₁ H ₄₈ N ₂ O ₂ C: 77.45%; H, 10.06%; N,
5.83% Found: C, 77.34%; H, 9.95%; N,
5.56%

(4-c) (+)-5-decyl-2-
Synthesis of [4- (2-hydroxynonyl) phenyl] pyrimidine and (-)-5-decyl-2- [4- (2-hydroxynonyl) phenyl] pyrimidine (-) obtained in (4-b) above. To a solution of 40 mg of 2- [4- (2-acetyloxynonyl) phenyl] -5-decylpyrimidine in 5 ml of methanol was added 2N aqueous sodium hydroxide solution at room temperature, and the mixture was stirred for 1 hour. After distilling off the solvent under reduced pressure, the obtained residue was washed with brine,
The reaction product was extracted with ether and concentrated, and the obtained residue was purified by column chromatography (hexane / ethyl acetate = 4/1) to give (+)-5-decyl-
2- [4- (2-hydroxyphenyl] pyrimidine 30
mg (yield: 85%) was obtained. Similarly, the above (4-b)
40 mg of (+)-2- [4- (2-acetyloxynonyl) phenyl] -5-decylpyrimidine obtained in () was used to obtain (-)-5-decyl-2- [4- (2-hydroxynonyl). Phenyl] pyrimidine 33 mg (yield: 94
%) Was obtained.

[Α] _D ²⁰ + 5.9 ° (c = 0.91, C
HCl ₃ ) and -5.0 ° (c = 1.1, CHCl ₃ ) IR (KBr) 3428, 2926, 2851, 15
89, 1429, 793 cm ^{-1 1} H NMR (CDCl ₃ ) δ 0.88 (t, J =
6.8 Hz, 3 H), 0.89 (t, J = 6.0 Hz,
3H), 1.26 to 1.33 (m, 22H), 1.51
~ 1.57 (m, 2H), 1.62 to 1.69, (m,
2H), 2.62 (t, J = 14 and 8.2Hz, 1
H), 2.89 (dd, J = 14 and 4.3 Hz, 1
H), 3.87 (bs, 1H), 7.34 (d, J =
8.3 Hz, 2 H), 8.35 (d, J = 8.3 Hz,
2H), 8.61 (s, 2H) MS m / z 438 (M ⁺ , 0.9), 310 (10
0), 183 (12), 69 (11), 55 (11),
43 (16), 41 (13) High resolution MS C ₂₉ H ₄₆ N ₂ O M ⁺ calculated value m / z 438.3607 Measured value m / z 448.3589

(Example 5) Synthesis of (-)-2- (4-decyloxyphenyl) -5- (2-fluoroundecyl) pyrimidine (compound of (1a-q-1))

[0093]

[Chemical formula 22]

To a solution of 74 mg of (+)-2- (4-decyloxyphenyl) -5- (2-hydroxyundecyl) pyrimidine obtained in Example 1 in 5 ml of dichloromethane was added 1.0 M trifluoride at -78 ° C. 0.2 ml of dimethylaminosulfurized chloride (DAST) -dichloromethane solution was added,
Stir for 20 minutes. Water was added to the reaction solution, the reaction product was extracted with ether, the extract solution was concentrated, and then separated and purified using column chromatography (Wakogel C-300, hexane / ethyl acetate = 80/1), (- ) -2- (4
52 mg (yield: 72%) of -decyloxyphenyl) -5- (2-fluoroundecyl) pyrimidine was obtained. Further, it was recrystallized from a mixed solution of hexane / ether (5/1) to give (-)-2- (4-decyloxyphenyl) -5.
36 mg (yield: 50%) of-(2-fluoroundecyl) pyrimidine was obtained.

Colorless needle crystal Phase transition temperature (° C.) Cr86 SX83 I [α] _D ²⁰ -10.5 ° (c = 1.03, CHCl ₃ ) IR (KBr) 2922,2853,1607,15
84, 1541, 1435, 1254, 1165, 10
20,829,795 cm ^{-1 1} H NMR (CDCl ₃ ) δ 0.88 (t, J =
7.0 Hz, 3 H), 0.88 (t, J = 7.1 Hz,
3H), 1.26 to 1.73 (m, 30H), 1.77.
~ 1.85 (m, 2H), 2.86 (d, J = 5.7H
z, 1H), 2.92 (dd, J = 2.4, and5.
7 Hz, 1 H), 4.03 (t, J = 6.6 Hz, 2
H), 4.66 (dm, J = 49 Hz, 1H), 6.9.
8 (d, J = 9.0 Hz, 2H), 8.36 (d, J =
9.0 Hz, 2H) 8.62 (s, 2H) MS m / z 485 (M ⁺ +1, 36), 484
(M ⁺ , 100), 344 (11), 186 (30),
185 (51), 69 (17), 43 (53), 41
(19) Elemental analysis: Calculated as C ₃₁ H ₄₉ N ₂ FO: C, 76.81%; H, 10.19%; N,
5.78% Found: C, 76.55%; H, 9.92%; N,
5.73%

Example 6 Synthesis of (-)-2- (4-decyloxyphenyl) -5- (2-fluorodecyl) pyrimidine (Compound of (1a-q-2)) Obtained in Example 2. (+)-2- (4-decyloxyphenyl) -5- (2-hydroxydecyl) pyrimidine was used in the same manner as in Example 5 to obtain (-)-2- (4-decyloxyphenyl) -5. -(2-Fluorodecyl) pyrimidine was obtained.

Colorless plate crystal Phase transition temperature (° C.) Cr63 SX74 I [α] _D ²⁰ -10.0 ° (c = 0.98, CHCl ₃ ) IR (KBr) 2922, 2853, 1607, 15
86,1543,1441,1252,1171,10
26,828,795 cm ^{-1 1} H NMR (CDCl ₃ ) δ 0.88 (t, J =
6.9 Hz, 3 H), 0.89 (t, J = 6.8 Hz,
3H), 1.27 to 1.73 (m, 28H), 1.77.
~ 1.85 (m, 2H), 2.86 (d, J = 5.8H
z, 1H), 2.92 (dd, J = 2.4, and5.
7 Hz, 1 H), 4.03 (t, J = 6.6 Hz, 2
H), 4.68 (dm, J = 48Hz, 1H), 6.9.
8 (d, J = 9.0 Hz, 2H), 8.36 (d, J =
9.0 Hz, 2H) 8.62 (s, 2H) MS m / z 471 (M ⁺ +1, 33), 470
(M ⁺ , 100), 330 (18), 186 (27),
185 (59), 149 (30), 69 (10), 57
(27), 43 (45), 41 (25) Elemental analysis: as C ₃₀ H ₄₇ N ₂ FO Calculated value: C, 76.55%; H, 10.06%; N,
5.95% Found: C, 76.34%; H, 9.93%; N,
5.90%

Example 7 Synthesis of (-)-2- (4-decyloxyphenyl) -5- (2-fluorononyl) pyrimidine (Compound of (1a-q-3)) Obtained in Example 3. (+)-2- (4-decyloxyphenyl) -5- (2-hydroxynonyl) pyrimidine in the same manner as in Example 5 except that (-)-2- (4-decyloxyphenyl) -5 was used. -(2-Fluorononyl) pyrimidine was obtained.

Colorless needle crystal Phase transition temperature (° C.) Cr48 SX77 I [α] _D ²⁰ -10.4 ° (c = 1.00, CHCl ₃ ) IR (KBr) 2922, 2853, 1607, 15
86, 1541, 1435, 1254, 1165, 10
17,831,795 cm ^{-1 1} H NMR (CDCl ₃ ) δ 0.88 (t, J =
7.1 Hz, 3 H), 0.88 (t, J = 6.7 Hz,
3H), 1.28 to 1.73 (m, 26H), 1.78.
~ 1.85 (m, 2H), 2.86 (d, J = 5.7H
z, 1H), 2.92 (dd, J = 2.3, and5.
7 Hz, 1 H), 4.03 (t, J = 6.6 Hz, 2
H), 4.66 (dm, J = 48Hz, 1H), 6.9.
8 (d, J = 9.0 Hz, 2H), 8.36 (d, J =
9.0 Hz, 2H) 8.62 (s, 2H) MS m / z 457 (M ⁺ +1, 32), 456
(M ⁺ , 100), 316 (34), 186 (25),
185 (74), 43 (34), 41 (21) Elemental analysis: as C ₂₉ H ₄₅ N ₂ FO Calculated value: C, 76.27%; H, 9.93%; N, 6.
13% Found: C, 76.23%; H, 9.82%; N, 6.
10%

(Example 8) (-)-5-decyl-2-
Compound of [4- (2-fluorononyl) phenyl] pyrimidine ((1b-q-1) (-)-5-decyl-2- [4- obtained in Example 4
Using (2-hydroxynonyl) phenyl] pyrimidine, in the same manner as in Example 5, (−)-5-decyl-2-
[4- (2-Fluorononyl) phenyl] pyrimidine was obtained. Melting point 42 ° C. ¹ H NMR (CDCl ₃ ) δ 0.8 to 1.0 (m,
6H), 1.26 to 1.69 (m, 28H), 2.61
(T, J = 6.0 Hz, 2H), 2.88 to 3.15
(M, 2H), 4.72 (dm, J = 45Hz, 1
H), 7.33 (d, J = 8.3 Hz, 2H), 8.3
4 (d, J = 8.3 Hz, 2H) 8.61 (s, 2H)

Example 9 Preparation of SC ^* Liquid Crystal Composition

[0102]

[Chemical formula 23]

A host liquid crystal (H-1) having an SC phase consisting of
Was prepared. The phase transition temperature of this host liquid crystal (H-1) is as follows. Phase transition temperature: 12.5 ° C (Cr → SC), 55.5 ° C
(SC-SA), 64.5 ° C (SA-N), 70 ° C (N
-I) 5% of each of the compounds obtained in the above Examples was added to this host liquid crystal.
SC ^* liquid crystal composition (M-1) to (M
-6) was prepared. The amount added and the phase transition temperature are summarized in Table 2. The melting point is omitted because it is not clear in many cases.

[0104]

[Table 2]

[0105] (above in, SC ^* is a chiral smectic phase, SA phase the smectic A phase, the N ^* chiral nematic phase, I represents represents isotropic liquid phase, respectively, the addition amount is obtained SC ^* liquid crystal Represents% by weight in 100% by weight of the composition.)

Example 10 Production of Liquid Crystal Display Device The SC ^* liquid crystal composition (M-4) obtained in Example 9 was heated to an isotropic liquid (I) phase, which was 2 μm in thickness. A glass cell consisting of two transparent electrode plates (polyimide coating-aligned by rubbing) was filled and gradually cooled until an SC ^* phase was exhibited to prepare a display element.

Electric field strength of 10 V _pp / μm, 5
When a rectangular wave of 0 Hz was applied and the electro-optical response was measured, a high-speed response of 200 μsec at 25 ° C. was confirmed. At this time, the tilt angle was 9.8 °, and the contrast was good. Further, when a triangular wave was applied and the spontaneous polarization thereof was measured, it was as small as 0.1 nC / cm ² or less. From this, it can be understood that the viscosity of the composition (M-4) is very small.

Similarly, the compositions (M-1) and (M-
6) was used to produce display elements, and the electro-optical response was measured. The results are shown below. (M-1): 1.75 msec (M-6): 450 μsec

[0109]

INDUSTRIAL APPLICABILITY The phenylpyrimidine derivative having an optically active 2-substituted alkyl group represented by the general formula (I) of the present invention has a low viscosity and is excellent in liquid crystallinity. Therefore, by adding it as a chiral dopant to the host liquid crystal composition exhibiting the SC phase, it is possible to provide a liquid crystal composition capable of high-speed response in a wide temperature range without narrowing the temperature range of the liquid crystal phase.

The compound of the general formula (I) of the present invention can be easily produced industrially, is colorless and has excellent chemical stability against water, light and the like, and is practical. The chiral smectic liquid crystal composition containing this compound can easily realize a high-speed response of about 200 μsec, and is extremely useful as an optical switching element for display.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Tetsuo Kusumoto 1-9-2-102 Minamidai, Sagamihara City, Kanagawa Prefecture (72) Inventor Kenichi Sato 35-11, Kamimizo, Sagamihara City, Kanagawa Prefecture (72) Kumiko Ogino Kanagawa Prefecture 23-1-702 Yotsuyakami-cho, Kawasaki-ku, Kawasaki-shi

Claims (6)

[Claims] 1. A compound represented by the general formula (I): (In the formula, R ¹ represents an alkyl group having 1 to 18 carbon atoms, X represents a single bond or —O—, m represents 0 or 1, and one of ring A and ring B is a fluorine atom. Represents a 1,4-phenylene group which may be substituted by, the other represents a pyrimidine-2,5-diyl group, and ring C is a 1,4-phenylene group which may be substituted by a fluorine atom or trans- denotes a 1,4-cyclohexylene group, Y _{-OH, -OCH 3, -OCF 2 H} , -OCF 3
Or a fluorine atom, R ² represents an alkyl group having 1 to 18 carbon atoms, and ^* represents that the carbon is an optically active asymmetric carbon. ) An optically active compound represented by: 2. The optically active compound according to claim 1, wherein m = 0 in the general formula (I). 3. The optically active compound according to claim 2, wherein Y in the general formula (I) represents —OH or a fluorine atom. 4. A liquid crystal composition containing the optically active compound according to claim 1. 5. The liquid crystal composition according to claim 4, which exhibits a ferroelectric chiral smectic phase. 6. A liquid crystal display device using the liquid crystal composition according to claim 4.