JPS63215682A - 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2- dioxabolinane derivative and liquid crystal material - 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 novel organic compounds having liquid crystal properties, and more particularly to 2-(4,3-disubstituted phenyl)-5-alkyl- as a liquid crystal substance component. 1,3,2-dioxaz I
The present invention relates to J-nate derivatives and liquid crystal materials for use in electro-optical devices.

The present invention is a method for the electronic industry 1 to display single-character numerical information.
It will find a wide range of applications, for example in electronic watches and small calculators.

Space below [Prior Art] Liquid crystal trans-2-(4-(4'- cyanophenylcargenyl)phenyl)-5-alkyl-1,
3-dioxane is well known in the art (J, fir
prakt, Cham, Bd, No. 323.6.

1981, Leipzig, Vollprot, Brerasch, Cleanza, Piedalepen, Denuse, Lascheke (L
aipzig, H.M., Vorbrodt, S.
.

Dsresch, H., Kresse, A., Wleg.
sleban, D.

Denues, H, La5chke), r5yn
these and Eigensehaftan 5u
bstituierter L3-Dloxana J
, pp. 902-13) These compounds are characterized by high temperatures (135 °C) of nematic phase formation and easy isomerization to cis isomers, while liquid crystal materials based on these compounds are characterized by their electro-optical parameters. Therefore, it is unsuitable for use in the negative temperature range.

The following formula, (in the above formula, R represents an alkyl group of a conventional structure containing 3 to 6 carbon atoms, and R' is 2-(4-substituted phenyl)-5-alkyl represented by 10R1) -1,3,
2-dioxagelinan is also well known (JP, A, 6
1-83190.61-109792).

These compounds have a slightly high temperature for nematic phase formation (
105°C or higher) and low negative anisotropy of dielectric constant. As a result, the threshold voltage and saturation voltage of the "twisting" effect of liquid crystal materials comprising these compounds are high, and the materials cannot be used at low temperatures.

[Problem that the invention seeks to solve]

The present invention provides novel 2-(4,3-disubstituted phenyl)-5- as a component of liquid crystal materials, characterized by a low temperature for nematic phase formation and a high positive anisotropy of the dielectric constant.
The present invention relates to an alkyl-1,3,2-dioxa♂linane derivative and to a liquid crystal material characterized by low limit voltage and saturation voltage values with short intermittent periods.

[Ninth way to solve the problem]

The object of the present invention is to use the following formula as a component of a liquid crystal material.

2-(4,3 -disubstituted phenyl)-5-alkyl-1,3,2-dioxagelinane.

It is also recommended to use a derivative of 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane represented by the following formula, YY.

It also contains at least two types of components, at least one of which is represented by the formulas (I) to (■) proposed herein.
2-(4,3-disubstituted phenyl)-5-alkyl-1
, 3,2-dioxaporinane derivatives are also proposed.

Advantageously, the content of the compounds of formulas (I) to (VT) proposed here in the liquid crystal material is between 3 and 75 percent by weight.

Such liquid crystal materials are characterized by optical properties.

The compounds of formulas (1) to (Vl) according to the present invention are characterized by a low nematic phase formation temperature and high positive anisotropy of dielectric constant. These characteristics include low threshold voltages and saturation voltages, steep voltage differences,
Guarantees short intermittent periods.

The liquid crystal material according to the present invention can be used, for example, in electronic watches,
It will find application in a variety of electro-optical devices with static and dynamic control modes in devices operating in diverse ways, such as television screens, personal computers, etc.

The methods for synthesizing the compounds of formulas (lI) to (Vl) are shown below.

Compounds of formula (II), (IV) are prepared by reacting 2-alkyl-1,3-7'ropanediol with 4,3-disubstituted phenylboronic acid in acetone.

Reaction of 2-alkyl-1,3-7'lopanediol with 4-calgexy-3-halodanophenylboronic acid and subsequent treatment of this reaction product with thionyl chloride gives the acid chloride, which can be prepared by conventional methods. 4-hydroxybenzonitrile, 4-hydroxybenzonitrile, 4-hydroxybenzonitrile, 4-hydroxybenzonitrile, 4-hydroxybenzonitrile,
-Hydroxy-2-halogenobenzonitrile.

The compound of formula (V) is prepared in the same manner as the compound of formula (■) using 4-carboxy-3,2'-disubstituted 4-diphenylboric acid.

The liquid crystal material according to the invention is produced by mixing at least two components, one of which is the 2-(4,3-disubstituted phenyl)-5-alkyl-1,
The 3,2-dioxagellinate derivative accounts for 3 to 75 percent by weight. This mixing is carried out under heat until an isotropic phase appears and then cooled.

Other components of this liquid crystal material are biphenyl, cyclohexane, dioxane, pyrimidine, alkyl (alkoxy)
Phenyl esters, derivatives of 4-furkyl(alkoxy)benzoic acid, as well as trans-4-alkyl-cyclohexanecarboxylic acids, alkylphenyl esters of 4-()trans-4-alkylcyclohexyl)benzoic acid, trans-4-alkyl 4- of cyclohexanecarboxylic acid
Any compound such as (trans-4-alkylcyclohexyl)phenyl ester, 1,2-diphenylethane, and 1-cyclohexyl-2-phenylethane may be used.

[Examples] The following are examples of specific embodiments of the present invention.
Examples 1 to 5 illustrate the preparation method and properties of 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxa,y IJnan derivatives of formula (II) to formula (■). Examples 6-9, however, illustrate the manufacturing method and properties of the liquid crystal materials.

Example 1゜2-(4-bentroxy-3-chlorophenyl)=5-
Pentyl-1,3,2-dioxaporinane (II) 0.02 mol 2-pentyl-1 in 5Qm acetone
, 3-propanediol, and 0.02 mol of 4-pentyloxy-3-chlorophenylboric acid.
Reflux for 5 hours. The solvent is evaporated and the resulting product is recrystallized from a small amount of acetone.

The yield of compound (ff) is 53%, and the melting point is 8°C. The number of carbon atoms in the alkyl group is 1 to 7, and X is H
, F, Ct atoms are prepared in a similar manner with yields of 50-72%.

Example 2゜2-(4-cyano-3-fluorophenyl)-5-pentyl-1+3+2-dioxa? A mixture containing 0.025 mol of 4-carboxy-3-fluorophenyl and 1.0.02 s mol of 2-pentyl-1.3-7'ropanediol in 70 ml of acetone is refluxed for 5 hours. The solvent is evaporated and the product is crystallized from methyl ethyl ketone. The resulting 0.02 moles of 2-(4-calgexy-3-fluorophenyl)-5-pentyl 1.
3. Reflux the 2-dioxaporinane with 5 ml of thionyl chloride for 1 hour. After evaporation of the excess thionyl chloride, the residue is treated with 15 ml of aqueous ammonia bath.

Separate the precipitated crystals, wash them with water, and air dry them.
of dimethylformamide and Q, f3 ml of thionyl chloride. The crystals are kept in this solution for 1 hour, then the solution containing the crystals is placed in an aqueous solution of sodium bicarbonate and extracted with diethyl ether. The ether solution is washed with water and dried over anhydrous sodium sulfate. The residue obtained after evaporating the solvent is recrystallized from methyl alcohol.

The yield of compound (1) is 45%, and the melting point is 29°C. the alkyl group has 1 to 7 carbon atoms, X is F,
Other compounds of formula (III) representing 01M molecules were prepared in a similar manner, with impressive yields of 48-57%.

Example 3゜2-(4-ethyl-3-fluoro-4'-diphenyl)
-5-pentyl-1,3,2-dioxaporinane (ff
) Preparation of 100 d of KO in acetone, 0.2 moles of 2-pentyl-1,3-7'ropanediol, 0.02 moles of 4-alkyl-3-fluoro-4'-diphenylboric acid is refluxed for 3 to 4 hours. do. The solvent is evaporated and the product obtained is recrystallized from a small amount of acetone.

The yield of compound (IV) is 53% and the melting point is 87°C.

The alkyl group has 1 to 7 carbon atoms.

Other compounds of formula (IV) in which X and Y represent H, F, and Ct atoms are also prepared in a similar manner, with yields ranging from 45 to 59%.
Met.

Example 4 Preparation of 2-(4-cyano-3,2'-difluoro-4'-diphenyl-5-pentyldioxaborinane (V)) 0.02 mol of 2-pentyl-1. 3-Nia'lopanediol, 0.02 mol of 4-
The mixture containing calgexy 3,2'-difluoro-4'-diphenylboric acid is refluxed for 10 hours. The solvent is evaporated and the product is recrystallized from toluene.

0.015 mol of 2-(4-carboxy-3,
2'-Difluoro-4'-diphenyl)-5-pentyl-1.3.2-dioxa/IJnan is refluxed with 7 tnl of thionyl chloride for 3 hours. The residue after evaporating excess thionyl chloride was dissolved in dioxane and diluted with 15 ml
Treat with aqueous ammonia. The precipitated crystals are separated, washed with water, air-dried and placed in 35 ml of dimethylformamide and 3 ml of thionyl chloride solution. This solution was allowed to stand for 4 hours, then poured into a sodium bicarbonate solution and extracted with diethyl ether. Wash this ether solution with water,
Dehydrate with anhydrous sodium sulfate. The residue obtained after evaporating the solvent is recrystallized from a mixture of hexane and isopropyl alcohol.

The yield of this compound (V) was 36%, and the melting point was 62°C.
It is.

The alkyl group has 1 to 7 carbon atoms, and X and Y are H
, F, C1 atoms were prepared in a similar manner with yields of 33-42%.

Example 5 Preparation of 2-(4'-(4-cyano-3-fluorophenyloxycarbonyl)-3'-fluorophenyl-5-benzene-1.3.2-dioxaporinane (VIs)) in 7 Qrnl of acetone. A mixture containing 0.25 moles of 4-carboxy-3-fluorophenyl 1R10,025% 2-pentyl-1,3-f-ropanediol is boiled for 5 hours in a flask fitted with a reflux condenser. Add 0.004 mol of 4-hydroxy-2-fluorobenzonitrile and 1 ml of pyridine. Leave the mixture overnight and filter. The residue obtained after evaporating the solvent is diluted with hexane and ethyl alcohol. The yield of this compound (■s) was 60%, and the melting point was 63°C.

Other compounds of formula (Via-w) can also be obtained in a similar manner,
The yield was 47-86%, and t0 compounds (■a-W)
The properties, yield and elemental analysis are shown in Table 1.

The novel compounds of formulas (I) to (Vla,) below are all white crystalline powders at room temperature.

The composition and structure of compounds (1) to (Vla-W) are confirmed by the results of elemental analysis and IR-1 NMR-spectral data.

Therefore, 1,3,2-dioxaporinane derivative (1) ~
(■) In the NMR spectrum of (10% solution in deuteroacetone, standard hexamethyldisiloxane, δ, ppm), a signal due to the hydrogen atom of the borinane moiety is observed in the region of 3.4 to 4.3. (3.54, 3.7
0,3.86,4.00.4.10.4.16゜4.2
6. Or 3.53, 3.63, 3.74, 3.
93,4.00°center at 4.13, 4.20)
. The signal due to the hydrogen atom of the benzene ring is 7.10-8
．． Observed in the region of 0.06 ppm. This compound (CC
t4. In the IR spectrum of a 0.01 molar solution in chloroform solution, the strong peak at 1715.2215- corresponds to the stretching vibration of the carbonyl and nitrile groups of the ester moiety.

Compounds according to the present invention and JP, A, 61-109
Comparative data on the nematic phase formation temperature and positive anisotropy of dielectric constant of the compounds disclosed in No. 792 are shown in Table 2.

The blank space below is the positive anisotropy of the dielectric constant measured at 60°C below the temperature at which the nematic phase changes to an isotropic liquid.From Table 2, this new compound (Vl) is JP, A, 6
It is obvious that the nematic phase formation temperature is lower than that of the compound disclosed in No. 1-109792, and the positive anisotropy of the dielectric constant is much higher.

Compounds of formulas (III) and (IV) shown here and JP
,A.

61-109792, the said compound of 15 mass cents and 85 mass f
A mixture was prepared consisting of a mixture of Formulation A of -St. This mixture of Formulation A is comprised of 66 weight percent 4-butylmethoxyanisole and 34 weight percent 4-butylmethoxyanisole.
It comprises butyl-4-hexylcarobiazobenzene. The results of the positive anisotropy of the dielectric constant of this prepared mixture are shown in Tables 3 and 4.

Below is a blank example 6゜20'lf 4-cyano-4'-bentildininyl (■), 10 mass t% of 4-ethoxy-nyl ester of trans-4-chlorohexanecardan acid) %30
fil1% (7) 2-(:4'-(4anophenyloxycarbonyl)phenyl2:ethyl-1,3-dioxane (IX), ethyl phenyl ester,
ethoxy full ester of 4-butylbenzoic acid of 10 ii-cents, and 2(4-cyano-3-fluorophenyl)-50 pyr-1,3,2- of 15 4-cents.
Prepare a mixture consisting of dioxagelinan (■) -
0 this mixture.

Heat and stir until the tropic phase forms.

Cool until warm. Table 5 shows the q properties of the liquid crystal material thus obtained.
Shown below.

The liquid crystal materials of formulations 2 to 54 were prepared using the same method.

Their properties are also shown in Table 5.

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Circle G Example 7゜trans-4-propyl-4(4'-ethoxyphenyl)cyclohexane 0■), 4-hexylhydrophenyl ester of trans-4-butylcyclohexanecarboxylic acid (LC), 2-(4-ethoxyphenyl) 3-fluorophenyl)-5-pentyl-1,3,2-dioxaporinane (I[), 2-(4'-(4-cyano-3-fluorophenylhydroxycarbonyl)-37-fluorophenyl)-5-pentyl Liquid crystal materials of formulations 55.1 to 55.2 comprising -1,3,2-dioxadolinane (8) were prepared analogously to the liquid crystal material of formulation 1 of Example 6.

The content of the components in the liquid crystal material of this formulation 55.1-55.2 and its electro-optical parameters measured at room temperature are shown in Table 6.

Below is a blank example 8゜trans-4-propyl-4(4'-ethoxyphenyl)cyclohexane (■), 4-hexylhydrophenyl ester of trans-4-butylcyclohexanecarboxylic acid (LC), 2-[4'-( Formulations 56.1 to 56.5 comprising 4-cyano-3-fluorophenylhydroxycarbonyl) + 37-fluorophenyl-5-d-1,3,2-dioxaporinane (3)
A liquid crystal material was prepared analogously to the liquid crystal material of Formulation 1 of Example 6.

The contents of the components in the liquid crystal material of the formulations 56.1 to 56.5 and their electro-optical parameters measured at room temperature are shown in Table 7.

Below is a blank example 9゜trans-4-7'ropyru(4-ethoxyphenyl)
Cyclohexane (■), 4-hexylhydroxyphenyl ester of trans-4-butylcyclohexanecarboxylic acid (LC), 4-ethoxyphenyl ester of trans-4-butylcyclohexanecarboxylic acid), 2-
[4'-(4-cyano-3-fluorophenylhydroxycarbonyl)-3'-fluorophenyl-5-phenyl-1,3,2-dioxaporinane (Vll), 2-
Formulations 57.1 to 57.8 comprising (:4'-(4-cyano-3-fluorophenylhydroxycarbonyl)-37-chlorophenyl]-5-pentyl-1,3,2-dioxaporinane (Vlt) The liquid crystal material was prepared similarly to the liquid crystal material of Formulation 1 of Example 6 and then:

The contents of the components in the liquid crystal materials of Compounds 57.1 to 57.8 and their electro-optical/base lame values measured at room temperature are shown in ff8.
U. is the voltage at which the cell transmits 10% of the irradiated light (limit voltage).

U3O is the voltage at which the cell transmits 50% of the irradiated light.

U. is the voltage at which the cell transmits 90% of the irradiated light (saturation voltage).

P5o is the immersion gauge (P2O” (U3
O-U,. )/TJ 1o) τ. , is the time during which the cell changes from 10% to 90%.

τ. 2F is the time during which the cell changes from 90% to 10%.

Δn is optical anisotropy.

Here, ΔU is the difference in the limiting voltage of the mixture at 50°C and 10°C, and ΔT is the difference in the limit voltage of the mixture at 50°C and 10°C, and ΔT is the difference in temperature change from 10°C to 50°C (Δ
T=5'-100=40'), U,. is 2o℃
Measure with.

ON and OFF periods are measured at U=3V.

Thus, as seen from Examples 1-9 and Tables 1-8,
The compounds of formulas (1) to (Vr) according to the present invention are JP, A
, 61-109792 , JP, A, 61-83190
It is characterized by a lower nematic phase formation temperature and higher positive anisotropy of dielectric constant than the compound disclosed in .

These characteristics can be achieved by using the compounds of the present invention.
It becomes possible to supply liquid crystal materials which are characterized by low limit voltages and saturation voltages, constant immersion voltage characteristics, short intermittent periods and operation at low temperatures.

〔Effect of the invention〕

The liquid crystal material according to the present invention has applications in a variety of electro-optical devices with static and dynamic control modes, for example in devices operating in a variety of ways, such as electronic watches, small computers, information display panels, personal computers, etc. will be found.

0 margins below Inventors: Alexander Basi Sorieevich Ipa's thousand, Donko La'viet Federation, Moskovskaya Oblast, Dolgoprny, Uritsa Pervomayskaya, 44 AR, Kvarchy procedural amendment April 4, 1988 Director General of the Patent Office Kuni Ogawa Husband 1, Indication of the case Patent Application No. 316338 of 1988 2, Title of the invention 2-(4,3-disubstituted phenyl)-5-alkyl-1,
3,2-Dioxaporinane derivative and liquid crystal material 3, relationship with the amended case Patent applicant 4, agent address 5-8-10 Toranomon-chome, Minato-ku, Tokyo 105
Subject of amendment (1) “Claims” column of the description (2)
Column 6 of “Detailed Description of the Invention” of the specification, Contents of amendment (1) The scope of claims will be amended as shown in the attached sheet.

(2) Table 5 on pages 27 to 61 of the detailed statement will be amended as shown in the attached sheet.

7. List of attached documents (1) Scope of claims iim
(2) Table 5 1 copy 2, claims 1. As components of the liquid crystal material, the following formula simultaneously or independently represents H, F or C1; R,
2-(4,3-disubstituted phenyl)5-alkyl-1,3,2-dioxaporinane m1 body represented by R' represents an alkyl group having a normal structure containing 1 to 7 carbon atoms.

2. Represented by the following formula, (in the above formula, X represents F or CX),
2-(4,3-disubstituted phenyl)-5-alkyl-1°3.2-dioxaporinane derivative according to claim 1.

3. 2-(4,3-disubstituted phenyl)-5-alkyl-1° according to claim 1, represented by the following formula, Y (in the above formula, X represents F or Ci) 3.2-dioxaporinane m1 body.

4, the following formula, (in the above formula, X and Y are H, F or C simultaneously or independently)
2-(4,
3-Disubstituted phenyl)-5-alkyl-1°3.2-dioxaporinane derivative.

5, the following formula, (in the above formula, X and Y are simultaneously or independently H, F or C
2-(4, 1) according to claim 1,
3-Disubstituted phenyl)-5-alkyl-1°3.2-dioxaporinane derivative.

6, the following formula, (in the above formula, X and Y are H, F or C simultaneously or independently)
2-(4,
3-Disubstituted phenyl)-5-alkyl-1°3.2-dioxaporinane derivative.

7. A liquid crystal material comprising at least two components, in which at least one of the components is represented by the following formula, and simultaneously or independently represent H, F or C1; R,
2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative represented by A liquid crystal material characterized by

8. The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is a compound represented by the following formula: (In the above formula, X represents F or C1) A liquid crystal material according to claim 7, characterized in that:

9. The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is a compound represented by the following formula: (In the above formula, X represents F or C1) A liquid crystal material according to claim 7, characterized in that:

10, The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative has the following formula, (wherein X and Y are simultaneously or independently H, F or C
1) The liquid crystal material according to claim 7, wherein the liquid crystal material is a compound represented by:

11. The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane'BM conductor has the following formula, (wherein X and Y are simultaneously or independently I-(, 8. The liquid crystal material according to claim 7, wherein the liquid crystal material is a compound represented by: (representing F or C1).

12, The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative has the following formula, (wherein X and Y are simultaneously or independently [(, F or C1 8. The liquid crystal material according to claim 7, which is a compound represented by:

13, the content of the 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is 3
13. Liquid crystal material according to any one of claims 7 to 12, characterized in that it is in the range 75% by weight.

Table 5 Table 5 ('4It) Table 5 (continued) 3, ■
20 15.26 -8 70.4[[115 ■ 10! Fight X 15 XI 10 4, ■
20 11.96 -6 67.411I
15 ■ 10 X 15 XI 10 Table 5 (continued) 5, ■ 20
15.01 -8 65.0III
15 ■ 10 X 15 XI t.

Table 5 (continued) 7, ■ 20 29
．． 76 -12 70.4 ■ 15 ■ 10 X 15 XI 10 Table 5 (continued) 8. ■ 20
20.07 -7 59.4m
15 ■ 10 X 15 Ll 10 9, ■ 2
0 21.6 -1 62.4[[115 ■ lO X 15 X[10 Table 5 (continued) 10, W
20 13.05 0 54.4I [115 ■ 10 X 15 XI 10 Table 5 (Vt) Table 5 (continued) 12, ■
15 9.21 -14 71.3I [111 Xn 9 ■ 10 Xm 12 XIV 18 XV IQ 13, ■
15 13.81 -10 59.7m
11 χ■ 9 ■ 10 Table 5 (continued) 14. Vl 15
8.28 -15 62.01 [111 X■ 9 Table 5 (continued) 14,
■ 1゜XI[+
12 XIV 1B XV 10 Shi 1 15, W 15
10.78 -17 63.21 [111
15.25 -21 53.4Il+
11 X11 9 Table 5 (vt) 17. ■ 1゜Xm 12 XIV 18 XV 10 18, ■ 15
14.04 -17 51.6 [[[11 χ■9 ■ IO 3
13.87 -10 81.1XV+
4 χ■ 3
zICN (XX) c, n,, (Y) Yugiri) c mountain (XX1) Table 5
(continued) 22, ■ 3
15.23 -6 72.8XVI
4 χ■ 3
3 34.25 -8 77.2XVI
4 X■ 3 X■ 5 XIX 15 XII 6 ■8 XX 3 XXI 5 XI 3 Table 5 (continued) 25, ■ 3
22.07 -2 64. IXVI
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X 5 29.73 -3 78.1χK
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5 24.11 -8 82.3XXI
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5 Xχ■5 XXV 3 Table 5 (continued) 29. ■
5XXVI 10 XX■ 2 Table 5 (continued) 30, XX
5 24.21 -10 82.6χX[[l
5XXrV
5 XXV 3 ■ 5 ×5 XXVI 10 XX■ 2 11 To table 5 (1*ki) Table 5 (continued) Table 5 (continued) i 32, xχ■
3 32.14 -7 93.2XXIX
3 XXX 3 XXXI 3 Xχχ■ 3 XXm 5 XIX 5 Table 5 (continued) 33, χχ■
3 32.27 -8 94.5XXIX
3 XXXχ 3 XXXI 3 XXX II 3X■
5 X[X 5 Table 5 (continued) Table 5 (continued) Table 5 (continued) 35. XXW 3
15.07 1 84. IXXIX
3 XXX 3 XXXI 3 XXX■ 3 X■ 5 XIX 5 36, XXXVI
3 22.6 0 77.2χχ■3 Table 5 (continued) 36, XXX
3XXX+ 3 XXXχ■3 X■ 5 XIX 5 37, XXX■
3 21.57 -8 91.7XXX IX
3XXX
3 XXXI 3 XXX■ 3 X■ 5 XXXI 5 Table 5 (continued) 38, XXX■
3 25.11 -9 91.7χXX
IX 3XXX
3 XXXI 3 XXX I+ 3X■
5 XXI 5 39, XXW
3 24.12 -3 95.2XXIX
3 Table 5 (continued) 39, XXX
3XXXI 3 XXX■ 3 X■ 5 X[X 5 40, XXW
3 58.43 -11 100.8XXIX
3 XXX 3 XXXI 3 XXX■ 3 X■ 5 XIX 5 Table 5 (continued), 11. XXW
3 27.14 1 68.6XXX
IX 3XXX
3 XXX+ 3 XXX■ 3 X■ 5 XIX 5 42, XXVI
3 41.13 +3 77.1X
XIX 3 Table 5 (continued) 42, XXX
3XXXI 3 XXXχ■3 X■ 3 XIX 5 43, XXXIII
3 21.14 +6 75.8XXI
X 3 XXX 3 XXXT 3 XXχ■3 X■ 5 XIX 5 Table 5 (continued) Table 5 (continued) Table 5 (continued) 45. XXXI[[86,13-
2675,2XXI[[12 XXXrV 17xxy+
13 XXXV 10 XIX 10 XXX Vl 7XXX■
7 XXX ■ 8 XXX IX 546,
XXXII+
8 6.23 -29 80.1XχII+
12XXX rV
17 Table 5 (continued) 46, XXVT
13χXχV 10 X[X IQ XXX Vl 7XXX■
7 XχX■ 8 XXX IX 547,
XXXI[[88,16-3881,4X
XI [112 XXX TV 17XXV+
13 XXXV 10 XIX 10 Table 5 (continued) 47, χXXVI
7XXX■ 7 XXX■ 8 XXX IX 5Table 5
(Continued) Table 5 (Continued) 49. XXXI[1105,02
-3478,2XXm 12 XXX IV 1? XXVI
13 XXXV 10 XIX 't.

χXXVT 7 XXX■ 7 xxx■ 5 XXX IX 5Table 5
(continued) CsH++0CHtCHt+CN (XXXrV)c,
If, -C) CIl, CH, 80C mountain (XXVI) cs
o l +0CIIzClb80Czlls (XXX
V) CsHq<Czlls (X IX) O C mountain () Bekami (V C mountain (XXXW) CIl () - one (giant←ζ site CtHs (XXXW)
Table 5 (continued) 51, XXXIII
10 5.06 -33 76.1XXI[I
12XχXrV
17XXyl 13 XXXV 10 XIX 10 XXX V+ 7XXX■
7 Table 5 (continued) 51, XXXW
5XXX IX 55
2. XXXIII
10 5.12 -30 80.3XXI
I [12 Table 5 (continued) 53. XXX[[[105,1
4-2980,9XχI[I 1
2XXX rV 17 Table 5
(continued) 53, XXVI
13XXXV 10 XIX 10 XXX Vl 7XXX■
7 XXXX■ 5 XXX IX 554,
XXXl11 10
5.03 -31 79.4XXIII
12XXX IV
17XXVX 13 XXXν 10 XIX 10 Table 5 (continued) 54, XXXVI
7XXX■ 7 XXX■ 5

Claims (1)

[Claims] 1. The following formulas as components of liquid crystal materials: ▲ Numerical formulas, chemical formulas, tables, etc. There are▼、▲There are mathematical formulas, chemical formulas, tables, etc.▼、
2-(4,3-disubstituted phenyl) represented by ▲Mathematical formulas, chemical formulas, tables, etc.▼, where X and Y represent an alkyl group with a normal structure containing 1 to 7 carbon atoms 5-alkyl-1,3,2-dioxaporinane derivative. 2. 2-(4,
3-Disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative. 3. 2-(4,
3-Disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative. 4. The following formula, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the above formula, X and Y are H, F or C simultaneously or independently.
2-(4,
3-Disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative. 5. The following formula, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the above formula, X and Y are H, F or C simultaneously or independently.
2-(4,
3-Disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative. 6. The following formula, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the above formula, X and Y are H, F or C simultaneously or independently.
2-(4,
3-Disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative. 7. A liquid crystal material containing at least two types of components, at least one of which has the following formula, ▲Mathematical formula, chemical formula, table, etc.▼ (In the above formula, A is -OR', - CN, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
2-(4,3-disubstituted phenyl) represented by ▲Mathematical formulas, chemical formulas, tables, etc.▼, where X and Y represent an alkyl group with a normal structure containing 1 to 7 carbon atoms -A liquid crystal material characterized by being a 5-alkyl-1,3,2-dioxaporinane derivative. 8. The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is the compound according to claim 2, Liquid crystal material according to scope 7. 9. The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is the compound according to claim 3, Liquid crystal material according to scope 7. 10. The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is a compound according to claim 4,
A liquid crystal material according to claim 7. 11. The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is a compound according to claim 5,
A liquid crystal material according to claim 7. 12. The 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is a compound according to claim 6,
A liquid crystal material according to claim 7. 13, the content of the 2-(4,3-disubstituted phenyl)-5-alkyl-1,3,2-dioxaporinane derivative is 3
13. Liquid crystal material according to any one of claims 7 to 12, characterized in that it is in the range 75% by weight.