JPH04134050A - Optically active compound, polymer liquid crystal and liquid crystal composition containing said liquid crystal - Google Patents

Abstract

NEW MATERIAL:An optically active compound shown by the formula R<1>-X-R<2> [R<2> is group shown by formula I (C* is asymmetric carbon; k is 42 integer; Z is CH3 or halogen); X is group shown by formula II, etc. (ring B is group shown by formula III, etc.; Y is COO, OCO, CH2O or OCH2; Q is H, halogen or CN); R<1> is group shown by formula IV, etc. (R<3> is >=3C alkenyl having unsaturated bond at end)] or the formula R<4>-X-R<5> [R<4> is group shown by formula V (R<6> is each group in R<3>; R<5> is group shown by formula VI, etc. (m is >=2 integer)]. EXAMPLE:(R,S)-4-(2-(7-Octenyloxypropanoyloxy)biphenyl 4-(1-oxo-2-methylbutyl) benzoate. USE:A raw material for a polymer ferroelectric liquid crystal widely showing a chiral smectic liquid crystal phase approximately at normal temperature, having high spontaneous polymerization, high response speed because of high spontaneous polarization and applicable to display materials of curved large pictures. PREPARATION:An optically active substance shown by formula VII is reacted with an optically active substance shown by formula VIII to give an optically active substance shown by the formula R<1>-X-R<2> (X is group shown by formula II).

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an optically active compound, a polymer liquid crystal, and a liquid crystal composition containing the same, which can be applied to various optical elements.

[Conventional technology and its issues]

Liquid crystals with high-speed response to electric fields, good viewing characteristics, and contrast characteristics are attracting attention as materials for realizing high-performance liquid crystal display devices. However, this liquid crystal has problems in that it is difficult to control the cell gap over a large area, and it is weak in bending and shock resistance, making it difficult to adapt to large area displays and curved displays.

Therefore, as an attempt to improve this point, it has been considered to make the low-molecular ferroelectric liquid crystal into a polymer to give it moldability and shape retention ability. (Japanese Unexamined Patent Publication No. 55-21479) However, conventional polymeric ferroelectric liquid crystals have a slow operating speed (cannot be used for displaying moving images) and have the problem of high operating temperature.

An object of the present invention is to provide a polymeric ferroelectric liquid crystal that exhibits a wide range of chiral smectic liquid crystal phases near room temperature, has large spontaneous polarization, and therefore has a fast response speed, and can be applied to large-screen curved display materials. It is in.

[Means to solve the problem]

The present invention focuses on the fact that the optically active compounds represented by the general formulas (1) and (r[) have large spontaneous polarization, and the following general formula (II
The present invention provides a polymeric liquid crystal having main repeating units represented by I) and (IV), and a liquid crystal composition containing at least 1 component of this polymeric liquid crystal.

(O8,) (I) R''R1' (wherein, R7 represents an alkyl group, R9 represents CkH2, 1CHCO* (C* represents an asymmetric carbon, k is an integer of 2 or more, ,Z
represents a methyl group or a ]\rogen atom. )X represents any one of CH, O-, -0CR,-; p is 1 or 2; Q is hydrogen, )\rogen atom, or nitrile group; ).

R8 is CHs CHs Cl
2RI0CHCOO-R"0CHCOO-, R10CH
COO**** (C* represents an asymmetric carbon, and RIG is an alkyl chain having 3 or more carbon atoms.

Whether the absolute configuration of R8 where Z is a methyl group is (S),
When Z is a halogen atom and the absolute configuration of R9 is (R), CH.

The absolute configuration of RIOCHCOO is (S), but CH.

The absolute configuration of R”0CHCO○ is * (R) Q The absolute configuration of R”CHCOO is * (S) It is (S) When CH.

The absolute configuration of R”CHCOO is * (R) Hs The absolute configuration of R”OCHCOO is * (S) Q The absolute configuration of R”CHCOO is * (R).) (0-8i) (IV) R”- X (in the formula, R11 represents the alkyl group, the R shows R14chco - * (C indicates asymmetric carbon, and R14 indicates an alkyl chain with 3 or more carbon number. Z is a methyl group or ＼ Rogen atom. ) X is (However, CI(,0-, -OCH,-.
Or 2. Q is hydrogen, a halogen atom, or a nitrile group. ).

R'3 is CH3CIl+ CIC□H,
11,,CHCOO-,C,,H2□,0CIICOO
-, Cm112□, CllCOO**** (C* represents an asymmetric carbon, m represents an integer of 2 or more.)
Either, and the absolute configuration of the R eye where Z is a methyl group is (S), or
CH when Z is a halogen atom and the absolute configuration of R12 is (R);

C,,,H7□,,The absolute configuration of CHCOO is (S), *H3 C□I-12□,,,0The absolute configuration of CRCOO is (R)
,C.Q.

The absolute configuration of C,,82m,,CHCOO is (S)*, and the absolute configuration of R12 where Z is a methyl group is (S), or the absolute configuration of R11 where Z is a halogen atom is (R )
When CH3 CmH, m,, the absolute configuration of CHCOO is (R), * H3 C□H41゜,,0 the absolute configuration of CHCOO is (S), * CQ Cml-1,,,,, the absolute configuration of CHCOO is ( R) is represented by *. ) In the optically active compound according to claims 1 and 2 of the present invention, two optically active groups are introduced into one molecule with a core portion sandwiched therebetween, and the sign of spontaneous polarization based on the optically active group is determined. By making them the same, it is possible to realize a compound that exhibits a much larger spontaneous polarization than the sum of the spontaneous polarizations exhibited by compounds containing each optically active group alone. Furthermore, in the polymer liquid crystal according to claims 3 and 4 of the present invention, by bonding the optically active compound according to claims 1 and 2 to the polysiloxane chain,
It is possible to realize a polymer liquid crystal that exhibits large spontaneous polarization and therefore responds quickly to an electric field.

The present invention will be explained in detail below.

A compound with a partial structure consisting of a carbonyl group directly sandwiched between a core and an asymmetric carbon exhibits large spontaneous polarization.
This has already been reported by the present inventors. (Tokugan Sho 6
3-278618) Most of the ferroelectric liquid crystals that have been reported so far have used dipoles with ester or ether groups; By replacing the group with a carbonyl group, the spontaneous polarization can be increased approximately in proportion to the group moment of these groups. Furthermore, if a methylene group is present between the carbonyl group and the asymmetric carbon, the spontaneous polarization becomes extremely small.

An optically active compound in which a carbonyl group-containing partial structure described in ``2'' and another optically active group are combined with a core sandwiched between them,
If the signs of the spontaneous polarization based on two optically active groups are the same, the spontaneous polarization will be larger than that exhibited by a compound containing each optically active group alone. However, the degree of increase varies depending on the type of other optically active groups used in combination and the type of core.

The present invention realizes a compound that exhibits a much larger spontaneous polarization than the sum of the spontaneous polarizations of compounds containing each optically active group alone by selecting the types of cores and other optically active groups to be combined. .

That is, in the optically active compound according to claim 1 of the present invention, the optically active alkanoyl group R2 is C, H,
CHCO* (C represents an asymmetric carbon, k is an integer of 2 or more, and Z represents a methyl group or a halogen atom) is combined with a core between them as an optically active group R+ to form CH3CHs.
CQR'C) ICOO-R30C) ICOO
-R3CHCOO*** (C represents an asymmetric carbon, R3 is an alkenyl group having 3 or more carbon atoms and having an unsaturated bond at the terminal). Further, in the optically active compound according to claim 2 of the present invention, the optically active alkanoyl group R4 is R'CHCO* (C represents an asymmetric carbon, R' is a group having 3 or more carbon atoms and having an unsaturated bond at the terminal). Indicates an alkenyl group.

Z represents a methyl group or a halogen atom. ), CHa as the optically active group R5 to be combined with the core in between.
C113CQC-Htl, l-+0HC
OO-, CmIIt, 1. +0CHCOO,C-H2
=-+CHCOO*** (C represents an asymmetric carbon, and m represents an integer of 2 or more.) It is necessary to select one of the following. In the polymer liquid crystal according to claim 3, R6 is CKl(, ni, , CHCO * (C represents an asymmetric carbon, k is an integer of 2 or more, and 2 represents a methyl group or a ]\rogen atom) ) as R8, Cl1s CIl+
CQRIoCHCOO-R”0CHCOO-R30
It is necessary to select one of CHCOO*** (C* represents an asymmetric carbon and RIG is an alkyl chain having 3 or more carbon atoms).

Further, in the polymer liquid crystal according to claim 4, R+t is R14CHCO* (C* represents an asymmetric carbon, R'' represents an alkyl chain having 3 or more carbon atoms, and Z represents a methyl group or a halogen atom.

) as RIG*** (C* represents an asymmetric carbon, m represents an integer of 2 or more.)
You need to choose one. At this time, R1 and R'', R' and Rs, Re and RIo, Rth and R1
The combination of absolute configurations of 3 and 3 must be as follows in order to match the signs of the spontaneous polarization based on both.

That is, the absolute configuration of R2 where Z is a methyl group is (S)
or the absolute configuration of R1 where Z is a halogen atom is (
R), the absolute configuration of H3 R'CHCOO is (S), * The absolute configuration of H5 R30CHCOO is (R), * The absolute configuration of CQ CH3 R3CHCOO is * (S), and ? ■H2■. The absolute configuration of CHCO○ is * (S) If the absolute configuration of R2 where Z is a methyl group is (R) and is C H ,l or if the absolute configuration of R2 where Z is a halogen atom (S) then C mH The absolute configuration of 2m◆ O C R C O O is * (R) Cl! CHG C,H,. ．． ．． The absolute configuration of C H C O O is * (S) and the absolute configuration of R'CHCOO is * (R), and the absolute configuration of R4 where C H s Z is a methyl group is (R), so R 30 C H C Does the absolute configuration of O O have * (S)? When Z is a halogen atom and the absolute configuration of R4 is (S), the absolute configuration of CQ R'CHCOO must be *.

(R) Must be C143 C. ,,H2,◆ The absolute configuration of CHCOO is * (R) Also, the absolute configuration of R4 where Z is a methyl group is (S) C H 3 or the absolute configuration of R' where Z is a halogen atom is (R ) when C , H , . , O C H C O O has the absolute configuration * (S) CQ C H . ? ■I4? , l, l The absolute configuration of CHCOO must be * (R) and the absolute configuration of R 'CHCOO must be * (R).

CH. Also, the absolute configuration of R9 where Z is a methyl group is (S) Is it? Absolute configuration R of RI1 where Z is a halogen atom The absolute location of 00CHCOO is * (S) Place is When (R) CQ C H 3 R The absolute position of ’CHCOO is * (R) Must be R The absolute position of 0CHCOO is * (S) Must be.

Furthermore, when the absolute configuration of R 12, where Z is a methyl group, is (S), or the absolute configuration of R It, which is Z or a halogen atom CH s child, is (R), the absolute configuration of R 00CHCOO is * (R) C H 3 CQ. The absolute configuration of C , H ,,, CHCOO is * (S) R'' CHCO (M) The absolute configuration is (S) * The absolute configuration of R8 where Z is a methyl group is (R) and CH 3 Absolute configuration of R9 with Z or eight loken atoms? ■H, ■. O C H The absolute configuration of C○0 is * When (R) is (S), Cρ C, H,..., lCHCOO's absolute configuration is ( S), * and Z is a methyl group, the absolute configuration of R12 is (R), or Z is a halogen atom, the absolute configuration of R11 is (
CH when S).

The absolute configuration of C□H3ffi, 1CHC00 is (R),
*CH.

Absolute configuration ci(s) of C,H,,,0CRCOO,* Q C, H, , , CHCOO (7) Absolute configuration is (R) * There must be.

Introducing a halogen atom or a nitrile group into the core is often used as a means to improve liquid crystallinity and as a means to increase spontaneous polarization, and this method is also effective in the present invention. That is, the introduction of a fluorine atom, chlorine atom, bromine atom, or nitrile group,
Enhances liquid crystallinity and is effective in increasing spontaneous polarization.

The polymer liquid crystal of the present invention has an extremely useful property of responding rapidly to an electric field because of its large spontaneous polarization. Furthermore, Sc can be used in a wide temperature range including room temperature.
Since it exhibits a phase and is easy to mold, it can be used as a variety of optoelectronic materials, including displays, optical switches, and optical modulation elements.

This polymer liquid crystal is mixed with low molecular weight ferroelectric liquid crystal, non-ferroelectric liquid crystal, or other types of polymer liquid crystal to improve viscosity, response speed, helical pitch, etc., and to achieve excellent electro-optical properties and moldability. A material that is easy to process can be obtained.

Among the optically active compounds represented by general formulas (1) and (II), compounds in which Y is -COO- can be synthesized, for example, by the following route.

(or R'-CHCOC&) * (6) (A, ) or (A3) or (A5) + (B,
)→ (1) (A,) ten (R3)→ ([) (A,) or (A4) or (A6)+ (B,)→ (
It)(A2)-1-(B, )→ ([1) For optically active compounds represented by general formulas (1) and (II), compounds in which Y is 10CO- can be prepared, for example, by the following route. is synthesized with.

C+t+ C1+3 CI(.

Q or C, II2□, , -CIICOCQ) * Q or R3-ClIC0C * H3 (+0) (8,) 10 (Ba) or (R7) → (1
) (A8) + (B, ) or (R8) → (n) Among the compounds represented by the general formula (1) and (Tl), compounds that do not contain Y can be synthesized, for example, by the following route.

Q or C111211, ICHCOC* → (II) (R', R', Rri, R', R5, R6, k
, msha, +, Q, Z, Y are the same as above.

Q is 0 or 1. ) The polymeric liquid crystal represented by the general formula (III) can be obtained by reacting a polysiloxane with an optically active compound represented by the general formula (I).

The polymeric liquid crystal represented by the general formula (TV) is obtained by reacting polycyflo-beef san with an optically active compound represented by the general formula (n).

〔Example〕

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples. Structures of the compounds of Examples 1 to 8, phase transition temperatures upon cooling, and spontaneous polarization at 10'C below the upper limit temperature of the Sc phase,
The response speeds are summarized in Table 1. The liquid crystal phase and phase transition temperature were determined by differential scanning calorimetry (DSC) measurement and observation using a polarizing microscope. Table 2 also shows, as a comparative example, the results of spontaneous polarization and electric field response speed at 10°C below the upper limit temperature of the Sc phase for compounds each having a chiral structure independently in the present invention. When compared with the spontaneous polarization in Table 1, the effects of the present invention are clear. (Measurement of Spontaneous Polarization) A cell was prepared by injecting a polymer liquid crystal under reduced pressure between two ITO substrates of 1O x 10 mm whose thickness was adjusted to 10 μm with a spacer. This was determined by measuring the polarization reversal current value accompanying the reversal of the dipole of the molecule when a triangular wave with a frequency of IHz and 150 V was applied to this cell.

(Measurement of response speed) An electric field (2X 10'V
/ m ) and change the amount of transmitted light at that time (0 to 90%
) response time was measured.

[Example 1] (1) (R)-4-2-(7-octynyloxy)propanoyloxy-4'-hydroxybiphenol p, To a tetrahydrofuran solution of 2.05 g of p'-biphenol was added 151 g of triethylamine under water cooling. Ta.

A tetrahydrofuran solution containing 2.18 g of (R)-2-(7octenyloxy)propanoyl chloride was added dropwise to this solution, and the mixture was stirred for 12 hours. After the reaction, the mixture was diluted with chloroform and washed with pure water. After drying the solution over magnesium sulfate, the solvent was distilled off, and the residue was purified by column chromatography. Furthermore, it was recrystallized from ethanol and (R
)-4-2-(7-octynyloxy)propanoyloxy-4'-hydroxybiphenyl was obtained.

(2) (S)-4-(1-oxo-2-methylbutyl)
Synthesis of benzoic acid 1.87 g of 4-bumorobenzyl alcohol, 3.60 g of ethyl vinyl ether, and 0.09 g of fluoroboric acid were heated and stirred in dimethylformamide. After reacting for 8 hours, the mixture was cooled to room temperature and diluted with 100 ml of ether. It was washed with an aqueous sodium hydroxide solution and dried. After removing the solvent, it was purified with a silica column to obtain 4-bromo-(2-ethynethoxymethyl)benzene.

A solution of 2.4 g of (S)-2-methylbutyric acid chloride in anhydrous tetrahydrofuran (50 ml) under a nitrogen stream was
At 6 to -78°C, 2.83 g of Grignard reagent of 4-bromo-(2ethoxyethoxymethyl)benzene was added dropwise over 2 hours. Further, the mixture was stirred at room temperature for 2 hours. After the reaction,
Washed with 100 ml of water and extracted with diethyl ether. Furthermore, the extract was washed with an aqueous sodium hydroxide solution and a saturated saline solution, and dried over sodium sulfate. After distilling off the solvent,
Separated on a silica column, (S)-4-(1-oxo-2
-methylbutyl)-2-ethoxyethoxymethylbenzene was obtained.

(s)-4-(1-oxo-2-methylbutyl)(2-
264 g of (ethoxyethoxymethyl)benzene was stirred in trifluoroacetic acid at 0 to 20°C for 10 hours, and after removing the solvent, it was purified using a silica column.
-]oxo 2-methylbutylbenzyl alcohol was obtained.

(s)-4-(1-oxo-2-
200 g of (methylbutyl)hensyl alcohol was added, and 474 g of potassium permanganate was slowly added while maintaining the temperature at 20-30°C. After the reaction, the reaction mixture was added to an aqueous solution of thorium hydrogen sulfite and extracted with ether. After drying, concentrate and separate with a silica column to obtain (s)-4
-(]]oxo-2-methylbutylbenzoic acid was obtained.

(3) (R,5)-4-(2-(7-octenylAquin)propanoyloxy)biphenyl 4(1-oxo-
Synthesis of (R)-4-(7-octynyloxy)propanoyloxy-4'-hydroquinbiphenol and (s
) 3.68 g of -4-(1-oxo-2-methylbutyl)benzoic acid was dissolved in 50 ml of anhydrous dichloromethane, and 0.02 g of dimethylamine/pyridine and 2.27 g of chlorhexyl carbonimide were added thereto, and the mixture was left at room temperature overnight. Stirred. After the reaction, the generated precipitate was filtered off, and the solvent was distilled off. The purified product was purified by silica gel chromatography and further recrystallized from ethanol to obtain (R,5
)-1(2-(7-octynyloquine)propanoyloxy)biphenyl 4-(]-]oxo 2-methylbutylbenzoate was obtained.

IR (cm-') +2930 1760.1724
1684 16021270 +204 1072
890 766 [Example 2] Synthesis of polymer liquid crystal using the compound of Example 1 Toluene 1
(R8)-4-(1-(7) obtained in (1)
-octynyloquine)propanoyloxy)biphenyl 4-(1-oxo2-methylbutyl)benzoate 1
．． 12 g and 0.055 tvt% platinic acid isopropyl alcohol solution were dissolved in 0.05 cc and 0.12 g polysiloxane (Toshiba Silicone), and the tube was sealed after being completely degassed. After reacting this at 80°C for 15 hours, it was reprecipitated with methanol, filtered through Kelle, and dried to obtain the desired polymeric liquid crystal.

[Example 3] (R,5)-4-(2-(7-octynyloquine)propanoyloxy)biphenyl 4- (]]oxo2
-Synthesis of methyloctylbenzoate In Example 1 (2), (S)-2-methyloctanoic acid chloride was used in place of (S)-2-methylbutyric acid chloride except that (S)-2-methyloctanoic acid chloride was used. ) -1-(1-
Oxo-2-methyloctyl)benzoic acid was obtained. Furthermore, as in (3) of Example 1, (R)-4-(7-octynyloxy)propanoyloxy-4'-hydroxybiphenol and (S)-1-(+-oxo-2-methyloctyl)benzoin were added. (R,5)-1-(:2
- (7octenyloxy)propanoyloxy)biphenyl 4-(1-oxo-2-methyloctyl) Henshade was obtained.

IR (cm=); 2924. 2848. 1778.
1734. 1682 [Example 4] Synthesis of polymer liquid crystal using the compound of Example 3 (R,5)-4-(2(7-octynyloquine)propanoyloxy)biphenyl 4-(1 -oxo-2-methyloctyl)benzoate and polysiloxane were reacted to obtain a polymer liquid crystal.

[Example 5] (1) Synthesis of (R)-4-(2-(7-octynyloquine)propanoyloxy)benzoic acid In (1) of Example 1, 4-hydroxy instead of p,p-biphenol - By exactly the same reaction except that benzoic acid was used (R
)-4-(2(7-octynyloxy)propanoyloxy)benzoic acid was obtained.

(2) (S)-4-(1-oxo-2-methylbutyl)
Synthesis of phenol C■.

Dissolve 8.25 g of anisole in 100 ml of anhydrous 1,2-dichloroethane, cool to 0°C, and add 9.2 g to this.
of aluminum chloride was added little by little. Furthermore (R)
A solution of 92 g of -2-methylbutyric acid chloride dissolved in 50 ml was added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature for 1 hour. A further 9.2 g of ground aluminum chloride were then added and the reaction mixture was refluxed for 2 hours. After cooling to room temperature, the mixture was poured into 10 ml of water containing hydrochloric acid and extracted with chloroform. The extracted organic layer was washed with sodium hydrogen carbonate and water, and then dried. After distilling off the solvent, the constituent organisms were purified by silica gel chromatography, and (S)
-4-(1-oxo-2methylbutyl)phenol was obtained.

IR(am-') ;3305.1651.1602.
1578. 122'1(3)(S,R)-4-(1-
Oxo-2-methylbutyl)phenyl 4-(2-(7
Synthesis of -octynyloxy)propanoyloxy)benzoate The (R)-4-(2-(7-octynyloxy)propanoyloxy)benzoic acid obtained in the above reaction and (S)-1
-(1-oxo-2-methylbutyl)phenol was prepared from (S,R)-4- by the same reaction as in Example 1 (3).
(]-]oxo2methylbutylphenyl 4- (2
-(7-octynyloxy)propafiloxy)benzoate was obtained.

IR (cm-1); 292g, 1770. 173
0. 1682. 16021210, 1070.
765 Synthesis of panoyloxy)biphenyl-4'-carboxylic acid [Example 6] Synthesis of polymer liquid crystal using the compound of Example 5 The desired polymer liquid crystal was obtained in the same manner as in Example 2.

[Example 7] (1) Synthesis of (S)-4-(1-oxo-2-methyl9'-decenyl)phenol In (2) of Example 5, replacing (S)-2-methylbutyric acid chloride Using (S)-2-methyl-9-decenoic acid chloride, (S)4-(l-oxo-2
-methyl-9-decenyl)fer/- was obtained.

(2) (R)-1-(2-hexyloxyproExample 1)
(1), by using (R)-2-hexyloxypropanoyl chloride instead of (R)-2-(7octenyloxy)propanoyl chloride, (R)
-4-(2-hexyloxypropanoyloxy)biphenyl-4carboxylic acid was obtained.

(3) Synthesis of (S,R)-4-(1-oxo-2octenylpropyl))phenyl 4-(4'(2-hexyloxypropanoyluoquin)phenyl)henshade obtained by the above reaction. (S)-/I-(+-oxo2-methyl-9-decenyl)phenol and (R)1-(2-hexyloxyprobanoyl ookine)biphenyl-4'-
(S,R)-4-(1oxo-2-(7-octynylpropyl))tubonyl 4-(4'-(2-hexyloxypropyl)) is obtained from carboxylic acid by the same reaction as in Example 1 (3). Noyloxy)phenyl)benzoate was obtained.

IR (cm"'); 2930.1768.1730.
1680.1602 [Example 8] Synthesis of polymer liquid crystal using the compound of Example 7 The desired polymer liquid crystal was obtained in the same manner as in Example 2.

(The following is a blank space) 5: ([Effects of the invention] The polymer liquid crystal of the present invention exhibits a chiral smectic phase at around room temperature, and moreover, it exhibits larger spontaneous polarization than any previously reported polymer ferroelectric liquid crystal. Because of this, it responds quickly to electric fields.

Therefore, it is an extremely useful polymer liquid crystal that can display moving images on large screens and curved surfaces.

Claims (5)

[Claims] (1) General formula (I) R^1-X-R^2... (I) [In the formula, R^2 can be ▲a mathematical formula, chemical formula, table, etc.▼ (C^* is not represents a homogeneous carbon. k is an integer of 2 or more,
Z represents a methyl group or a halogen atom. )▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, ▲There are mathematical formulas, chemical formulas, tables, etc.▼▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ are ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Yes, Y is -COO-, -OCO-, -C
Indicates either H_2O- or -OCH_2-. p is 1
Or 2. Q is hydrogen, a halogen atom, or a nitrile group. ). R^1 is one of the following: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (C^* represents an asymmetric carbon, R^3 is an alkenyl group with 3 or more carbon atoms and an unsaturated bond at the end), When the absolute configuration of R^2 where Z is a methyl group is (S) or when the absolute configuration of R^2 where Z is a halogen atom is (R), the absolute configuration of ▲There are mathematical formulas, chemical formulas, tables, etc.▼ The arrangement is (S)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (R)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (S)
When the absolute configuration of R^2 where Z is a methyl group is (R) or the absolute configuration of R^2 where Z is a halogen atom is (S) ▲ There are mathematical formulas, chemical formulas, tables, etc. The absolute position of ▼ is (R)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (S)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (R)
It is. ) represents. ] An optically active compound represented by: (2) General formula (II) R^4-X-R^5...(II) [In the formula, R^4 can be ▲a mathematical formula, a chemical formula, a table, etc.▼ (C^* is not applicable) (R^6 represents an alkenyl group having 3 or more carbon atoms and an unsaturated bond at the end. Z represents a methyl group or a halogen atom.) , ▲Mathematical formula, chemical formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc.▼, (However, there are ▲mathematical formulas, chemical formulas, tables, etc.▼▲mathematical formulas, chemical formulas,
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ are ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Yes, Y is -COO-, -OCO-, -C
Indicates either H_2O- or -OCH_2-. p is 1
Or 2. Q is hydrogen, a halogen atom, or a nitrile group. ). R^5 has ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲There are mathematical formulas, chemical formulas, tables, etc. ▼ (C^* represents an asymmetric carbon, m represents an integer of 2 or more), and R where Z is a methyl group When the absolute configuration of ^4 is (S) or when Z is a halogen atom and the absolute configuration of R^4 is (R), the absolute configuration of ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is (S)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (R)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (S)
And when the absolute configuration of R^4 where Z is a methyl group is (R) or the absolute configuration of R^4 where Z is a halogen atom is (S), ▲The mathematical formula, chemical formula, table, etc. The absolute position of ▼ is (R)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (S)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (R)
represents. )] An optically active compound represented by (3) General formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(III) [In the formula, R^7 represents an alkyl group, and R^9 is ▲Mathematical formulas, chemical formulas, tables, etc. etc. ▼ Yes, Z represents a methyl group or a halogen atom. )X has ▲mathematical formulas, chemical formulas, tables, etc.
There are tables, etc.▼) (However, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ means ▲Mathematical formulas, chemical formulas, tables, etc.)
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ are ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Yes, Y is -COO-, -OCO-, -C
Indicates either H_2O- or -OCH_2-. p is 1
Or 2. Q is hydrogen, a halogen atom, or a nitrile group. ). R^8 has ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (C^* represents an asymmetric carbon, R^1^0 is an alkyl chain with 3 or more carbon atoms. R where Z is a methyl group When the absolute configuration of ^9 is (S) or when Z is a halogen atom and the absolute configuration of R^9 is (R), the absolute configuration of ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is (S)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (R)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (S)
and the absolute configuration of R^9 where Z is a methyl group is (R) or the absolute configuration of R^9 where Z is a halogen atom is (S) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ The absolute configuration of is (R)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (S)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (R)
It is. )] Polymer liquid crystal having a main repeating unit represented by. (4) General formula (IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(IV) (In the formula, R^1^1 represents an alkyl group, R^1^2 is, ▲Mathematical formula , chemical formulas, tables, etc. ▼ (C^* represents an asymmetric carbon, R^1^4 represents an alkyl chain with 3 or more carbon atoms. Z represents a methyl group or a halogen atom.) X is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc.▼ (However, there are ▲mathematical formulas, chemical formulas, tables, etc.▼ means ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ are ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Yes, Y is -COO-, -OCO-, -C
Indicates either H_2O- or -OCH_2-. p is 1
Or 2. Q is hydrogen, a halogen atom, or a nitrile group. ). R^1^3 has ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, (C^* represents an asymmetric carbon, m represents an integer of 2 or more), and the absolute configuration of R^1^2 where Z is a methyl group is (S), or When Z is a halogen atom and the absolute configuration of R^1^2 is (R), the absolute configuration of ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is (S)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (R)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (S)
And when the absolute configuration of R^1^2 where Z is a methyl group is (S) or the absolute configuration of R^1^2 where Z is a halogen atom is (R) ▲ mathematical formula, chemical formula, There are tables, etc. The absolute position of ▼ is (R)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (S)
, ▲There are mathematical formulas, chemical formulas, tables, etc. The absolute configuration of ▼ is (R)
represents. )] Polymer liquid crystal having a main repeating unit represented by. (5) A liquid crystal composition containing at least one component of the polymer liquid crystal according to claim 3 or 4.