JPH02229131A - Optically active compound, liquid crystal composition containing the same and production of intermediate for synthesis of optically active compound - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel optically active compound, a liquid crystal composition using this optically active compound, and a method for producing an intermediate for the synthesis of the optically active compound.

[Prior Art] Liquid crystal display elements have characteristics such as low driving voltage, low power consumption, thinness and light weight, and are used in calculators, watches, televisions, and the like. Although nematic liquid crystals are currently widely used as these display materials, they have the disadvantage of a slow response speed of several +m5 ec. As one attempt to improve this point, a display method using ferroelectric liquid crystal has been proposed. (N,
A, C1ark et al.: Applied Phys, Let
t, 36.899 [1980]) This method utilizes the chiral smectic C phase (hereinafter abbreviated as Sc* phase) of ferroelectric liquid crystal, and the ferroelectric liquid crystal material has Sc* phase. It is required to have a wide temperature range, large spontaneous polarization, and low rotational viscosity. but,
The ferroelectric liquid crystalline compounds reported so far are S
In addition to drawbacks such as a narrow temperature range of the c' phase and low spontaneous polarization, compounds containing an azomethine group also have the drawback of poor chemical stability, making them impractical.

In addition, when using ferroelectric liquid crystals as electro-optical devices, it is necessary to appropriately control the liquid crystal temperature range and electrical/optical properties, so several types of ferroelectric liquid crystals or compounds that induce ferroelectricity and A non-ferroelectric liquid crystal is mixed and used as a composition.

[Problems to be Solved by the Invention] For the reasons mentioned above, there has been a desire for a large number of compounds that have excellent chemical stability and have various properties that can be used as constituent components of ferroelectric liquid crystal compositions.

The purpose of the present invention is to provide a method for producing a chemically stable novel ferroelectric liquid crystal or a compound that induces ferroelectricity, and an intermediate for its synthesis. [Means for achieving this] The present invention will be explained as follows.

The invention according to claim I relates to an optically active compound, which has the following general formula (1) (wherein, R1 represents an alkyl group or a child having 4 to 22 carbon atoms), +COO-, Yl is a hydrogen atom, a halogen atom, a hydroxyl group, or a nitrile group; Y2 is a hydrogen atom, a halogen atom, a hydroxyl group, or a nitrile group; Z is a methyl group, an ethyl group, a methoxy group, or an ethoxy group;
Halogen atom, nitrile group, triph [noromethyl hanawa (YY), when both are hydrogen atoms, Z is ethyl group, methquino group, ethoquino group, halogen atom, nitrile group, 1 to reflo[ L) of the trimethyl group. ), Rz is an alkyl group having 10 or more carbon atoms, an alkokino group, an aryl group, or an aralgyl group,
* represents optically active carbon, and n is an integer of 0 to 6. )
It is characterized by being expressed as

The invention according to claim 12 relates to an optically active compound, in which R1 is an alkyl group having 4 to 22 carbon atoms, an alkoxy group, an elementary atom, or a halogen atom. represent. ), +c o o-, Y is a hydrogen atom, a halogen atom, a hydroxyl group, or a nitrile group, Y2 is a hydrogen atom, Z is an ethyl group, a metkyne group, an etkyne group, a halogen atom, a nitrile group, or a nitrile group. Any of the fluoromethyl groups, R2 is an alkyl group having 10 or less carbon atoms, an alkoxy group, an aryl group, an aralkyl group, C' represents an optically active carbon, and n is an integer from 0 to 6. Features: Dorochino.

The invention according to claim 3 (regarding the optically active compound J, 4' is 25-, 15L is the general formula (1゛)), and 1 is the carbon vi1-22 noal: 1 Kino JA ,X(
"Single bond, Y is a hydrogen atom, Y2 is a carbonyl υ) male hydroxyl group at the ortho position, Z is a methyl group, R2 is an alkyl group having 10 or less carbon atoms, C* represents an optically active carbon, and n is 0 to
It is characterized by being an integer of 6.

The invention of claim 4 is a chiral liquid crystal composition containing the optically active compound according to claim 1 (L) and claim 3 in an amount of at least the I component.

The inventions according to claims 5 to 8 all relate to a method for producing an intermediate for the synthesis of the optically active compound according to claim 1, and the invention according to claim 5 relates to a method for producing an intermediate for the synthesis of the optically active compound according to claim 1, wherein ) (wherein, R2 is an alkyl group, alkokino group, aryl group, or aralgyl group having a carbon number of 10 or less, and 7 is a methyl group, ethyl group, methokino group, ethoxy group, halogen atom, nitrile group, trifle group) :I l:I methyl Jj, 04 represents optically active carbon, is an integer from +1 to 6, and is an optically active acid chloride represented by 35);
-Hydroquine-4゛-me]quino-1hyphenyl,
Synthesis of a Lewis acid represented by the following general formula (111) (wherein R7, Z, C*, and n have the same meanings as above) This is a method for producing an intermediate for use.

The invention according to claim 6 provides the following general formula (IV) (wherein, R
3 represents an alkyl group or benzyl group having 22 or less carbon atoms. ) 3-Hydroquine 4°-substituted-1,1°
A Lewis acid is applied to an optically active compound represented by general formula (V) produced by reacting hifenyl with an optically active acid chloride represented by general formula (■) in a basic solvent. This is a method for producing a synthetic intermediate represented by general formula (VI) (wherein R2, R3, z, c', and ``initial'' have the same meanings as above), which is characterized by:

The invention according to claim 7 is a method for producing an intermediate represented by the general formula (1), characterized in that a Lewis acid is allowed to act on the optically active compound represented by the general formula (V).

The invention according to claim 8 provides a method for producing a synthetic intermediate represented by the general formula (II1), characterized in that a Lewis acid is allowed to act on the optically active compound represented by the general formula (VI). be.

The present invention will be described in detail below.

The molecular structure of a compound exhibiting or inducing ferroelectricity consists of a terminal flexible part, a core part and a chiral carbon part. Claims 1, 2 and 3 of the present invention
A feature of the described invention is that a ferroelectric liquid crystal with large spontaneous polarization or an optically active compound that induces large spontaneous polarization has been realized by directly bonding a carbonyl group to the core portion. The spontaneous polarization of ferroelectric liquid crystals is caused by dipoles perpendicular to the molecular axis of the liquid crystal. Most of the ferroelectric liquid crystals that have been reported so far have utilized dipoles of ester groups or ether groups. In the optically active compound of the present invention, the dipole sandwiched between the core and the optically active carbon is changed from an ether group or an ester group to a carbonyl group, thereby increasing the dipole moment and spontaneous polarization of these groups. Furthermore, the feature of the invention according to claims 1 to 3 of the present invention is that by introducing various substituents into the core part, optically active compounds having various properties and capable of becoming constituent components of chiral liquid crystal compositions can be produced. The reason lies in the fact that it has come true.

Among the substituents, a hydroxyl group introduced at the ortho position of the carbonyl group has a particularly remarkable effect. That is, by introducing a hydroxyl group to the ortho position of the carbonyl group, an intramolecular hydrogen bond is formed, and the dipoles of the carbonyl group and the hydroxyl group point in the same direction, thereby further increasing the spontaneous polarization. In the optically active compound according to claim 1 and claim 3 of this invention, a methylene group may be interposed between the carbonyl group and the optically active carbon, but the carbonyl group and the optically active carbon are directly connected. This has a remarkable effect on increasing spontaneous polarization. Introducing a methylene group between the carbonyl group and the optically active carbon has the effect of improving liquid crystallinity.

Furthermore, the liquid crystal composition according to claim 4 contains at least l component or more of the optically active compound according to claims 1 to 3 represented by the general formula (1), but other than the chiral liquid crystal composition. The component may be a ferroelectric liquid crystal compound or a non-chiral liquid crystal compound.

Examples of compounds other than the compound represented by general formula (1) used in the present invention are not shown below.

a) Ferroelectric liquid crystal compound R6-@S@1- coo +0R7 R60++COO+QR7゜In the formula, C* represents optically active carbon, and rt is the number of carbon atoms: 6
~14 straight chain alkyl group, R5 is a straight chain alkyl group having 2 to 6 carbon atoms or an isobutyl group.

b) Non-ferroelectric liquid crystal compound R60-@-Coo -@-R7 Rd filter C○o -@-OR7゜R6COO-@-Coo ((eaves R7 R6Coo -@-Coo -@-OF!7 in formula , R6
, R7 each represent an argyl group having 4 to IO carbon atoms.

Next, an example of a method for producing an optically active compound represented by the general formula (1) and an intermediate for synthesizing the optically active compound will be described.

Among the optically active compounds represented by the general formula (1), compounds in which Yl is a hydrogen atom, Y, or a hydroxyl group introduced at the ortho position of a carbonyl group, and where an alkyl group is not directly connected to the hyphenyl ring, are: It can be produced by reacting a synthetic intermediate represented by general formula (II1) with any of the following compounds (■) to (■).

RHal (■) (In the above compound, 1-2 carbon atoms
The alkyl radical of 2, 11a1 represents a halogen atom, and I represents a hydrogen atom or a halogen atom. ) This reaction is carried out in the presence of alkali in the case of the compound (■), and in the presence of a basic solvent such as pyridine in the case of the compounds (■) to (Xl). Compounds in which Y is a hydrogen atom, Y2 is a hydroxyl group introduced at the ortho position of the carbonyl group, and an alkyl group is not directly connected to the pivot ring of the optically active compound represented by the general formula (1) are It can also be synthesized, for example, by the following route without going through the synthetic intermediate represented by the general formula (fil).

It means.

The intermediate for synthesizing an optically active compound represented by the general formula (I1) can be produced, for example, by the following route.

The reaction from compound (XIV) to compound (In) can also occur through the following route.

A I C1z −> 130°C (I1) The reaction from compound (XII1) to compound (II1) can also occur through the following route.

Otsu It can be easily obtained by processing.

3. ) Optical occupancy acid Rz9”H-(CHz)nc OO
The following compounds are preferably used as H.

(CH3)2C)l CH2 cl-13 CI-(COOH.

CH3C2H5C)1(C)-13)CH(CH2)2COO
H.

[Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples and Production Examples, but of course the gist and scope of the present invention are not limited by these Examples.

(Example 1) S-(+)-3,4'-dihydroquine-4-(2methylbutyroyl)-1,1'-biphenyl (general formula (II1
) Synthesis of a compound in which Z is a methyl group, R7 is an ethyl group, and n is O
Suspended at 00mC and added 10% of M-iodophenol to this.
' A DMF solution of Og (0.45 mol) was added dropwise, and 70
The reaction was stirred at ±5°C for 30 minutes.

Then Hensyl chloride 57.4. g (0,454 mol) was added dropwise, and the mixture was reacted at 10'0±5°C for 2 hours. After injecting water IQ into the reaction solution, it was extracted with ethyl acetate, and the organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the solvent was distilled off, and the crystallized residue was recrystallized from ethanol to give 3-benzyloxyiodobenzene 11
9.7 g was obtained as white crystals. (Yield: 85%, m,
p, 51. (1-53,0℃) HN M R6ppm (
CD C+23) was obtained as crystals. (Yield 58%, m,
p, 78.5-81.0°C)'HNMRδppm (CD
C (3) 3.83 (3H, S, CH30-) I R (K B r) cm-': 1240 ■ Synthesis of 3-benzyloxy-4'-methoxy-1,1'-biphenyl In the above item 0 Obtained 3-benzyloxyiodobenzene 11
9 g (0,384 mol) and p-iodoanisole 8
9.9 g (0,384 mol) was heated to 60±5°C, 210 g of copper powder was added thereto, and the mixture was reacted at 200 to 210°C for 10 hours. 500 mρ of toluene was injected into the reaction mixture, insoluble materials were filtered off, and the solvent was distilled off to obtain crude crystals, which were separated by column separation (filling material: Watugel C-200, eluent: n-hexane/ethyl acetate = 20/ 1) 64.8 g of 3-benzyloxy-4methoxy-1,1゛-biphenyl was formed into a white crystal. ■ Synthesis of 3-hydroquine-4°-methoxy-1,1-biphenyl 3-benzyloxy-obtained in item 0 above. 4°-methoxy-
29.0 g (0.1 mol) of 1,1-biphenyl was dissolved in 300 ml of ethyl acetate-tetrahydrofuran mixture,
Catalytic reduction under 2g Raney nickel catalyst (initial hydrogen pressure: 55
kg/cm", reaction temperature = 100±10°C), the catalyst was filtered off, and the solvent was distilled off to obtain crude crystals.

Then, the crude crystals were separated by column separation (filling material: Watugel C-2
00, eluent/n-hexane/ethyl acetate = 1O/1
) L, 3-hydroxy-4゛-methoxy-1゜1“-
15.1 g of biphenyl was obtained as white crystals.

(Yield near 6%, m, p, 76.5-78.0°C) Z
? -'HNMRδppm(CDC(23):3.82(3
')l,s,'cH-0-)5.59(IH,bs,=
OH) ■Synthesis of S-(+)-2-methylbutyroyl chloride 5-(
40 g (0.39 mol) of -1-)-2-methylbutyric acid and 70 g of thionyl chloride were gradually heated and reacted at 50 to 60°C for 2 hours. After the reaction, it was concentrated, and the residue was distilled at normal pressure to give S(+)-chloride (2
42 g of -methyl)butyroyl were obtained as a colorless oil.

(Yield: 90%) ■s-(+)-3-(2-methylbutyroyloxy)-
Synthesis of 4°-methoxy-1,lo-biphenyl 15 g (75 mmol) of 3-hydroxy-4°-methoxy-1.1°-biphenyl obtained in section The obtained S-(+)-2-methylbutyroyl chloride 9.1 g (75 mmol) was mixed with 20 to
It was added dropwise at 30°C, and the mixture was stirred and reacted at the same temperature for 2 hours. After the reaction, dilute aqueous hydrochloric acid solution was injected to neutralize the reaction mixture, and the mixture was extracted with ethyl acetate.

The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was distilled off and the remaining pale yellow oil was separated by column (filling material: Watugel C-200, eluent: n-hexane/ethyl acetate = 5/l), and S(+)
-3-(2-methylbutyroyloxy4°-methoxy-
205 g of 1,1°-biphenyl was obtained as a pale yellow oil. (Yield: 96%) [ff]: + 1 2.0
°(cm 2 , C H C (!3)'HNMR
δppm (CD C 12s): 103 (3H, t
, J=7Hz, -CI(CHtCt(a)1, 33(3
FI, d, J・7) 1z. -CI(CH*)1,55~
1.97(2H,m,-CHCHt-CHs)2,58
~2.73(LH,m, -COCH-)3,82(3
H,S,CH30) ■S-(+)-3-Hydroquine-4-(2-methylbutyroyl)-4'-methokino-11'-biphenylnitrobenzene (15 mρ) was added with 57 g of aluminum chloride and heated to 70°C. Add to this the S−(→−) obtained in the above 0 term.
-3=(2-methylbutyroyl oxine)4-methoxy-
IOg (35 mmol) of 1,1'-biphenyl was added dropwise. The reaction was then carried out at 115 to +25°C for 3 hours. The reaction solution was poured into a dilute aqueous hydrochloric acid solution, and then extracted with ethyl acetate.

Insoluble matter was filtered off, and the organic layer was separated, washed with water, and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the brown oil obtained by distilling off the solvent was separated by column separation (filling material, Watugel C2).
00, eluent/n-hexane/ethyl acetate-10/l
), S-(+)-3-hydroquine-4-(2methylbutyroyl)-4'-methoquino-1,1hyphenyl3.
7 g was obtained as a pale yellow viscous oil.

(Yield 37%) [α] ・+195° (cm 2 , CHCQ3)
HN M Rδ ppm (CD CL+) 0, 9
6 (3H, t, J=7H2, -CHCH2CH3)1
．． 24 (3H, d, J・7H2, -CHCH3) 1, 5
0-1, 93(2H, m, -CHC[Iz-CH3
)3.4:2-3.52(11-1,m, -COCH-
)3.83(3H,S,CI+30)12.73(
IH,s;-0H) I R(Neat)cm-':3400.2920,1
605 elemental analysis value (C+-H2oO*) Theoretical value 0%, 78.03, H% 7.09 Actual value 2C%, 75.85, H% 713■S-(+)-3,
4'-dihydroxo 4-(2methylbutyroyl)-1
, S-(+:)-3-hi)login-4 obtained in Section 2 of "Synthesis of 1'-biphenyl"
2.8 g (10 mmol) of (2-methylbutyroyl)-4'-methoquino-1F-biphenyl and 17 g of aluminum chloride were stirred and refluxed for 3 hours in 30 ml of toluene (!).The reaction solution was poured into a dilute aqueous hydrochloric acid solution. The organic layer was separated, washed with water, and dried over anhydrous sodium sulfate.The desiccant was filtered off, and the brown oil obtained by evaporation of the solvent was column-separated (filling material/fuco -Gel C-20
01, eluent n-hexane/acetone-10/l)t,
, S-(+)-3,4°-dihydroxy-4-(2-
1.7 g of methylbutyroyl)-1,1°-biphenyl were obtained as a pale yellow viscous oil. (Yield, 63%) [α]
o: +18.5° (cm 2 , CHCQ3)'HNM
Rδppm (CD CI23): 0.96 (3H, t,
J=7H2,-CHCI(2C1(3)1.25(31
(d, J=7Hz, -C)HCH3) 1, 50-1.9
3(211,m, -CIICH2-CH3)3.41
-3.50 (1) 1. m, -COCH-)l R(N
eat) am Elemental analysis value (C, 7H theoretical value 0%, 75 actual value 0%, 75 (Example 2) 3-hydroquine-4-methoxyphenyl to S -(+)-3,4 3350, 2960, 1610 53 .11%671 50 ・H%681 1 Synthesis of 1'-bidihydroxymethylbutyroyl)-1, bibiphenyl 15 mQ of nitrobenzene, 57 g of aluminum chloride and 3-hydroxy-4methoxy-1, obtained in Section 0 above. l
Add 7.0 g (35 mmol) of o-biphenyl and 70°C.
The S-(+)-chloride 2- obtained in Section 0 above is added to this.
4.8 g (40 mmol) of methylbutyroyl was injected. Subsequently, the reaction mixture was stirred at 130 to 135°C for 4 hours, and after cooling, the mixture was poured into a dilute aqueous hydrochloric acid solution and extracted with ethyl acetate. Separate the organic layer, wash with water, dry (anhydrous magnesium sulfate),
Evaporation of the solvent gave a brown oil. Column separation of oil (
Filler: Watugel C-200, eluent/n-hexane/acetone-10/l) L, S-(+)-3,4"dihydroxy-4-(2-methylbutyroyl)1.1'-biphenyl 2.3 g of the product was obtained as a pale yellow viscous oil (yield: 24%). The specific rotation of the ice crystals, IR and 'HNMR spectra completely matched those produced in Example 1.

(Example 3) S-(+)-3-(2-methylbutyroyloxy)4'-methoxy-1, biphenyl to S-(+)-3,
4°-dihydroxy-4-(2-methylbutyroyl)-
Synthesis of 1,1°-biphenyl S-(+) obtained in item 0 above
-3-(2-methylbutyroyl)-4'-methoxy-1
A reaction was carried out in exactly the same manner as in Example 2 using 10 g (35 mmol) of 1'-biphenyl, and S-(+)-3,4'-
Nohydroquine-4-(2-methylbutyroyl l-1,1
449 g of '-biphenyl was obtained. (Yield: 52%) The specific rotation, IR, and 'HNMR spectra of the ice crystals completely matched those produced in Example 1.

(Example 4) S-(+)-3,4'-dihydroxy-4-(2methylbutyroyl)-1,1"-biphenyl to S-(+)-
3-Hydroxy-4-(2-methylbutyroyl)-4'-cutyloxy-1,1'-biphenyl (general formula (1)
Synthesis of a compound in which R4 is an octyl group, X is a methyl group, R7 is an ethyl group, and n is 0) S-(+)-3 obtained in Examples 1 to 3 ,4
゛-Dihydroxy-4-(2-methylbutyroyl)-1
, 2.7 g (0.01 mol) of 1'-biphenyl was mixed with 1.4 g of potassium carbonate, 33 g of potassium iodide and n-bromide.
Stirring and refluxing in 1.9 g (0.01 mol) of octyl and 30-mg acetone was carried out for 12 hours, and after cooling, inorganic substances were filtered off.
Evaporation of the solvent gave a crude oil.

Column separation of oily substance (filling material: Watugel C-200,
eluent/n-hexane) and further recrystallized from ethanol to obtain 0.9 g of S-(+)-3-hydroxy-4(2-methylbutyroyl)-4'-year-old ctyloxy-1,1-biphenyl. Obtained as white crystals. (Yield: 24X
m, p・44.5-45.5°C) [α]D: + 12.
4°(c-2, CHCl23)'HN M R6ppm
(CD CQ3>:0.89 (3■, t, J=6.5H
z, CHs(CHy)e-)0.98(3H,t,J=
7H2, -CI(C)+2CI(3) 1.23-1.9
5(17H,m, CH3(CH,)8-, -COCHC
H3 and -C)IsItch3) 3.38-3.50 (IH, m, -COCH-)TR
(K B r) cm-': 2910 2850 160
Five-element analysis value (CzsHs-03) Theoretical value 2C%, 78.49: l1% 8.96 Actual value 0%, 78.56 1% 889 (Example 5) m-iodophenol and p-iodophenol From S-
Synthesis of (+)-3-hydroxy-4-(2-methylbutyroyl)-4'-octyloxy-1-biphenyl p-El-dophenol and n-octyl bromide were combined with item 0 of Example 1. A similar reaction was carried out to obtain 4-octyloxyiodobenzene as a pale yellow oil.

(Yield 95%) This 4-octyloxyiodobenzene and the 3-benzyloxyiodobenzene obtained in Example 1, Item 0 were reacted in the same manner as in Example 1, Item 0, and 3-benzyloxy-4'- Octyloquine 1.1°-biphenyl was obtained as pale yellow crystals.

(Yield 36%) This compound was treated in the same manner as in Section 0 of Example 1 using 5% paramium carbon as a catalyst.
Quin-4-octyloxy-11biphenyl was obtained as pale yellow crystals. (Yield 70%) This compound was reacted with 5-(-+-) 2-methylbutyroyl chloride obtained in Section 0 of Example 1 in the same manner as in Section 0 of Example 1, and S -(+)- 3-
(2-Methylbutyroyl okino)-4'-octyloxy-1,1 hiphenyl was obtained as a pale yellow oil. (Yield 92%) This s-(+)-3-(2-methylbutyroyl oxine)
-4゛-octyloxy-1,lo-biphenyl 1.2
The reaction was carried out in the same manner as in Section 0 of Example 1 using 3 mmol of g (3 mmol), and the resulting oil was separated in a column (packing material: Wakogel C-200, eluent: n-hexane), and then re-treated with ethanol. Crystallized to S-(+)-3-hydroxy-4
-(2-methylbutyroyl)4″-octyloxy-1
, 1-piphenyl (04 g) was obtained as white crystals. (Yield: 35%) Water world melting point, specific optical rotation, lR,'l+NMR
The subvector was completely identical to that obtained in Example 4.

(Example 6) Each compound was mixed in the following ratio to produce a liquid crystalline composition.

2-(4-nonyloNzophenyl)-5-7° tilbyrimizone 222%2-(j-to)%t”
t Noah 1'-1u) 51rJflb pirimino/
22.2% 2-(4-octyl-N-zophenyl)-5-octyl-N-zobyrimizone 22.2%
4-hentyl-N-diphenyl 4-octyl-N-diphenyl 7.1% 4-hentyl-N-diphenyl-4-octyl-N-diphenyl 4-octyl-N-diphenyl
71% 4-hexol-N-zophenyl 4-tezoloxy hepatate 7.1% 4-to!
When the phase transition of this composition was observed using a polarizing microscope, it was as follows.

Leaf 0 or less Sc” 42 SA 58.4 N 70
．． 4°C1 This liquid crystalline composition was placed in a test liquid crystal cell (IT○
A polyimide film is provided on a glass plate on which is vapor-deposited, rubbed in a certain direction, and sealed in a glass bead (diameter 2 μm) used as a spacer to bond two substrates together.
A test element was manufactured. When a voltage of ±IOV was applied to this test element and observed using a polarizing microscope, a change in transmitted light intensity was observed. The response time was determined from the intensity change and was 400 μsec at 25°C.

1. Effect of the invention] As explained above, in the general formula () according to claim I, 7]
, the compound of the present invention is chemically! l'IIL
It is an optically active compound that does not exhibit properties as a ferroelectric liquid crystal itself.

When mixed with a spiral liquid crystal compound, it has the excellent property of exhibiting large spontaneous polarization and being able to provide a ferroelectric liquid crystal composition that operates at high speed.

Further, according to the production method according to claims 5 to 8 of the present invention, it becomes possible to easily obtain an intermediate for synthesizing an optically active compound.

Claims (8)

[Claims] (1) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R_1 is an alkyl group or alkoxy group having 4 to 22 carbon atoms, X is a single bond, -COO, ▲Mathical formula , chemical formulas, tables, etc. ▼ (L represents a hydrogen atom or halogen atom), ▲ Numerical formulas, chemical formulas, tables, etc. ▼, Y_1 is a hydrogen atom, a halogen atom, a hydroxyl group, or a nitrile group , Y_2 is a hydrogen atom,
Any of a halogen atom, a hydroxyl group, or a nitrile group; Z is a methyl group, an ethyl group, a methoxy group, an ethoxy group, a halogen atom, a nitrile group, or a trifluoromethyl group (
However, when Y_1 and Y_2 are both hydrogen atoms, Z is any one of an ethyl group, a methoxy group, an ethoxy group, a halogen atom, a nitrile group, and a trifluoromethyl group. ), R_2 is an alkyl group, alkoxy group, aryl group, or aralkyl group having 10 or less carbon atoms, C^*
represents optically active carbon, and n is an integer of 0 to 6. ) optically active compound represented by (2) In the general formula (I) according to claim 1, R_1
is an alkyl group or alkoxy group having 4 to 22 carbon atoms,
is a single bond, -COO, ▲Mathematical formula, chemical formula, table, etc.▼ (L represents a hydrogen atom or a halogen atom.)▲Mathematical formula,
There are chemical formulas, tables, etc. Any of ▼, Y_1 is a hydrogen atom, halogen atom, hydroxyl group, or nitrile group, Y
_2 is a hydrogen atom, Z is an ethyl group, methoxy group, ethoxy group, halogen atom, nitrile group, or trifluoromethyl group; R_2 is an alkyl group with 10 or less carbon atoms, an alkoxy group, an aryl group, or an aralkyl group Or C^
An optically active compound characterized in that * represents optically active carbon, and n is an integer of 0 to 6. (3) In the general formula (I) according to claim 1, R_1
is an alkoxy group having 4 to 22 carbon atoms, X is a single bond, Y_1
is a hydrogen atom, Y_2 is a hydroxyl group at the ortho position of carbonyl, Z is a methyl group, R_2 is an alkyl group having 10 or less carbon atoms, C^* represents an optically active carbon, and n is an integer from 0 to 6. Featured optically active compounds (4) A chiral liquid crystal composition containing at least one component of the optically active compound according to claim 1. (5) General formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (II) (In the formula, R_2 is an alkyl group, alkoxy group, aryl group, or aralkyl group having 10 or less carbon atoms, and Z is methyl group, ethyl group, methoxy group, ethoxy group, halogen atom, nitrile group, trifluoromethyl group, C
^* represents optically active carbon, and n is an integer of 0 to 6. ) and an optically active acid chloride represented by 3-hydroxy-4
General formula (III) characterized by reacting '-methoxy-1,1'-biphenyl with Lewis acid in the presence of a Lewis acid ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (In the formula, R_2, Z, C^*, n have the same meanings as above.) Method for producing an intermediate for synthesizing an optically active compound (6) General formula (IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) (In the formula, R_3 represents an alkyl group or benzyl group having 22 or less carbon atoms.) 3-hydroxy-4 ′−
General formula (V) produced by reacting substituted-1,1' biphenyl and the optically active acid chloride represented by the above general formula (II) in a basic solvent ▲ Numerical formula, chemical formula, table, etc. There is a general formula (VI) characterized by the action of a Lewis acid on the optically active compound represented by (V) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(VI) Z, C^*, n have the same meanings as above.) Method for producing an intermediate for synthesizing an optically active compound (7) The optically active compound represented by the general formula (III) is treated with a Lewis acid.
) Method for producing an intermediate for optically active compound synthesis represented by (8) The optically active compound represented by the general formula (VI) is treated with a Lewis acid;
) Method for producing an intermediate for optically active compound synthesis represented by