KR19990011062A - Ixoxazolidine ring-containing liquid crystal compound and liquid crystal composition containing the same - Google Patents

Abstract

The present invention discloses an isoxazolidine ring-containing liquid crystal compound and a liquid crystal composition containing the same. The isoxazolidine ring-containing liquid crystal compound according to the present invention is chemically stable, and it is very easy to form a smectic phase because of the low temperature transition from the crystalline solid to the smectic phase. Such a liquid crystal compound may be used not only as a component of the liquid crystal composition but also to synthesize other kinds of liquid crystal compounds as a synthetic intermediate. The liquid crystal composition containing the liquid crystal compound according to the present invention can be very usefully applied to various liquid crystal display devices by appropriately adjusting birefringence, dielectric anisotropy, and the like.

Description

Ixoxazolidine ring-containing liquid crystal compound and liquid crystal composition containing the same

The present invention relates to a liquid crystal compound containing an isoxazolidine ring and a liquid crystal composition containing the same.

Many liquid crystal compounds containing pentagonal heterocycles are known. In particular, various studies have been conducted on pentagonal heterocyclic-containing compounds having nitrogen (N) and oxygen (O) atoms. Representative examples thereof include isoxazole ring-containing compounds (A) and oxa. Oxazole ring-containing compounds (B), oxadiazole ring-containing compounds (C), and benzoxazole ring-containing compounds (D).

However, the compounds generally have a problem that the formation of the smectic phase is not easy because the crystalline solid-smetic phase transition temperature is too high.

The first object of the present invention is to solve the above problems and to provide an isoxazolidine ring-containing liquid crystal compound having a lower crystalline solid-smectic transition temperature than in the related art.

The second technical problem to be achieved by the present invention is to provide a liquid crystal composition containing the liquid crystal compound.

In order to achieve the first object, the present invention provides an isoxazolidine ring-containing liquid crystal compound of the formula (1).

Wherein at least one of R ₁ and R ₂ is a group represented by the following structural formula,

Wherein Z ₁ is COO, OOC, CH ₂ CH ₂ , OCH ₂ , CH ₂ O, C≡C, CH = CH or CH ₂ ,

X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₅ , X ₇ and X ₈ are independently of each other, H, F or Cl, and R ₃ is C _n H _{2n + 1} , OC _n H _{2n +1} , SC _n H _{2n + 1} , C (= 0) C _n H _{2n + 1} , OOC-C _n H _{2n + 1} , COOC _n H _{2n + 1} , or NHC _n H _{2n + 1} , where n is An integer of 1-12);

The remaining R ₁ or R ₂ is unsubstituted C ₁ ~C ₁₂ straight-chain or branched alkyl, F, Cl, Br, CF 3, OCF 3 and substituted with at least one substituent selected from C ₁ ~C ₁₂ straight-CN A chain or branched alkyl group, provided that one -CH ₂ -or two non-adjacent -CH ₂ -is -O-, -S-, -CO-, -OCO-, -COO-, -OCS-,- Substituted by COS- and -CH = CH- and having -CH = CH ₂ and / or -CH = C (CH ₃ ) ₂ as a terminal group), a cyclohexyl group, a phenyl group, 4 -An alkylcyclohexyl group, a 4-alkylphenyl group, or a 4-alkoxyphenyl group, provided that the alkyl group is a C ₁ to C ₆ alkyl group.

A second object of the present invention is achieved by a liquid crystal composition containing an isoxazolidine ring-containing liquid crystal compound.

Preferably, at least one of R ₁ and R ₂

(Wherein Z ₃ is a chemical bond, an oxygen atom, a sulfur atom or a carboxyl group, and R ₄ is a C ₆ -C ₁₂ straight or branched saturated alkyl group).

The liquid crystal compound according to the present invention is a 1,4-diphenylisoxazolidine compound of Formula 2, 1-phenyl-4-alkylisoxazolidine of Formula 3 (1-phenyl-4 Particularly preferred are -alkylisoxazolidine-based compounds, biphenylisoxazolidine-based compounds of the formulas (4) and (5) and cyclophenylisoxazolidine-based compounds of the formula (6).

Wherein Y ₁ , Y ₂ , Y ₃ , Y ₄ , Y ₅ , Y ₆ , Y ₇ and Y ₈ are C _n H _{2n + 1} (n is a number from 1 to 8) irrespective of each other.

Referring to Scheme 1, a method for preparing a 1,4-diphenylisooxazolidine-based liquid crystal compound represented by Formula 2 will be described.

First, 4-alkoxybenzaldehyde (E-1) is reacted with an alkyl halide to produce 4-alkoxybenzaldehyde (E-2). Subsequently, 4-alkoxybenzaldehyde (E-2) is made of the corresponding oxime compound (E-3), which is then reacted with N-chlorosuccinimide (NCS) to give 1- (4 '). -Alkoxyphenyl) -4- (4-acetoxyphenyl) isoxazolidine (E-4). Hydrolyze 1- (4'-alkoxyphenyl) -4- (4-acetoxyphenyl) isooxazolidine (E-4).

The hydroxyl group of the compound (E-5) obtained by hydrolysis is changed to an alkoxy group to prepare 1- (4'-alkoxyphenyl) -4- (4-alkoxyphenyl) isoxazolidine.

Referring to Scheme 2, a method for preparing a 1-phenyl-4-alkylisoxazolidine-based liquid crystal compound represented by Chemical Formula 3 will be described.

4- (4'-alkoxyphenylcarbonyloxy) benzaldehyde (F-2) is formed from 4-alkoxybenzoic acid (F-1), and then the corresponding oxime compound (F-3) is formed. This oxime compound (F-3) is reacted with N-chlorosuccinimide to form 1- (4'-alkoxyphenylcarbonyloxyphenyl) -4-alkylisooxazolidine.

With reference to Scheme 3, a method for preparing a biphenylisoxazolidine-based liquid crystal compound represented by Formula 4 will be described.

4- (4'-alkylphenyl) benzoate (G-1) is reduced to produce 4- (4'-alkylphenyl) benzyl alcohol (G-2). This compound (G-2) is oxidized to form 4- (4'-alkylphenyl) benzaldehyde (G-3).

The aldehyde compound (G-3) is formed of the corresponding oxime compound (G-4) and then reacted with N-chlorosuccinimide to form 1- (4'-alkylbiphenyl) -4-alkylisooxazolidine To prepare.

With reference to Scheme 4, a method for preparing a biphenylisoxazolidine-based liquid crystal compound represented by Formula 5 will be described.

4-acetyl-4'-alkylbiphenyl (H-1) is reduced to form 4-alkyl-4 '-(1-hydroxyethyl) biphenyl (H-2). Water is removed from this compound to form 4-alkyl-4'-vinylbiphenyl (H-3).

On the other hand, the corresponding oxime compound (H-5) is formed from compound (H-4), and then compound (H-6) is formed using a halogenating agent such as N-chlorosuccinimide or the like.

Thereafter, the 4-alkyl-4'-vinylbiphenyl (H-3) is reacted with compound (H-6) to form a compound of formula (5).

Referring to Scheme 5, a method for preparing a cyclohexylphenylisoxazolidine-based liquid crystal compound represented by Chemical Formula 6 will be described.

The corresponding oxime compound (I-2) is formed from 4- (4′-alkylcyclohexyl) benzaldehyde (I-1). The oxime compound (I-2) is reacted with N-chlorosuccinimide to prepare 4-alkyl-1- (4 '-(4-alkylcyclohexyl) phenyl) isoxazolidine.

Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited only to the following Examples.

Synthesis Example 1

Preparation of 1,4-diphenylisooxazolidine

(1) 4-alkoxybenzaldehyde

To 10 g (0.082 mol) of 4-hydroxybenzaldehyde, alkyl bromide (0.080 mol), 0.25 mol of calcium carbonate and 20 ml of acetone were added, and the reaction mixture was refluxed for 5 hours.

The reaction mixture was cooled, filtered and distilled under reduced pressure to remove acetone.

250 ml of ethyl acetate, 50 ml of 1M NaOH and 50 ml of distilled water were added to the reaction mixture, and then the organic layer and the water layer were separated. The combined organic layers were then filtered and distilled under reduced pressure in 20 ml of dry anhydrous ether to give 4-alkoxybenzaldehyde (yield: 90 to 95%).

(2) 4-alkoxybenzaldoxime

30 mL of ethanol was added to 0.044 mol of 4-alkoxybenzaldehyde, and the reaction mixture was cooled using an ice bath. To the cooled reaction mixture, 10 ml of aqueous hydroxyamine hydrochloride (NH ₂ OH HCl) (0.05 mol) solution and 10 ml of aqueous sodium hydroxide (0.06 mol) solution were added sequentially. At this time, the temperature of the reaction mixture was adjusted so as not to exceed about 10 ° C.

The reaction mixture was stirred at room temperature for about 2 hours and then extracted with 500 ml of ethyl acetate. The collected ethyl acetate layers were dried, filtered and distilled under reduced pressure to obtain 4-alkoxybenz aldoxime (yield: 85 to 92%).

(3) 1- (4'-alkoxyphenyl) -4- (4-acetoxyphenyl) isoxazolidine

4.5 mmol of 4-alkoxybenz aldoxim was dissolved in 30 mL of CHCl ₃ , and then 4.5 mmol of N-chlorosuccinimide was added to dissolve completely. The reaction mixture was stirred at room temperature for 30 minutes and then 20 mL of a solution of CHCl _{3 in} p-acetoxystyrene (4.7 mmol) was added dropwise.

Thereafter, a solution of CHCl ₃ (10 mL) of triethylamine (5.4 mmol) was added dropwise to the reaction mixture for 30 minutes.

The reaction mixture was stirred for about 2 hours, then 50 mL of distilled water was added and extracted with 100 mL of chloroform. The reaction mixture was distilled under reduced pressure to remove chloroform, and then recrystallized from ethyl acetate to obtain 1- (4'-alkoxyphenyl) -4- (4-acetoxyphenyl) isooxazolidine (yield: 45-70%) .

(4) 1- (4'-alkoxyphenyl) -4- (4-hydroxyphenyl) isoxazolidine

9.2 mmol of 1- (4'-alkoxyphenyl) -4- (4-acetoxyphenyl) isooxazolidine was dissolved in 190 ml of ethanol, and then 40 ml of aqueous sodium hydroxide (0.046 mol) solution was added.

The reaction mixture was stirred at 50 ° C. for 12 h and then extracted with ethyl acetate. The reaction mixture was distilled under reduced pressure to remove ethyl acetate, and then recrystallized with ethanol to obtain 1- (4'-alkoxyphenyl) -4- (4-hydroxyphenyl) isoxazolidine (yield: 80 to 90%). .

(5) 1- (4'-alkoxyphenyl) -4- (4-alkoxyphenyl) isoxazolidine

A mixture of 7 mmol of 1- (4'-alkoxyphenyl) -4- (4-hydroxyphenyl) isoxazolidine, 0.3 mmol of alkyl bromide and 50 ml of acetone was refluxed for 15 hours under anhydrous conditions.

The reaction mixture was cooled, then filtered and distilled under reduced pressure to remove acetone.

The reaction product was extracted with 150 ml of chloroform. The combined organic layers were dried, filtered and distilled under reduced pressure. Subsequently, recrystallization with ethyl acetate gave 1- (4'-alkoxyphenyl) -4- (4-alkoxyphenyl) isooxazolidine (yield: 60 to 80%).

Synthesis Example 2

Preparation of 1-phenyl-4-alkylisoxazolidine

(1) 4- (4'-alkoxyphenylcarbonyl) oxybenzaldehyde

0.1 mol of thionyl chloride (SOCl ₂ ) was added to 0.02 mmol of 4-alkoxybenzoic acid, and the mixture was refluxed under anhydrous conditions for 2 hours. The reaction mixture was distilled under reduced pressure to remove excess thionyl chloride and then dissolved in 10 ml of anhydrous ether.

To the reaction mixture, 30 mL of anhydrous ether solution of 4-hydroxybenzaldehyde (0.025 mmol) and pyridine (5 mL) was added dropwise for 30 minutes.

The reaction mixture was stirred at rt for about 2 h and then extracted with 250 mL of ether. The ether layer was washed with 1M aqueous HCl solution, then dried, filtered and distilled under reduced pressure. Subsequently, column chromatography was performed on the resultant to obtain 4- (4'-alkoxyphenylcarbonyl) oxybenzaldehyde (yield: 60-85%).

(2) 4- (4'-alkoxyphenylcarbonyloxy) benz aldoxime

9.3 mmol of 4- (4'-alkoxyphenylcarbonyl) benzaldehyde was dissolved in 100 ml of ethanol and the reaction mixture was cooled using an ice bath.

To the cooled reaction mixture, 20 ml of hydroxyamine hydrochloride (9.7 mmol) aqueous solution and 20 ml of calcium carbonate (9.7 mmol) aqueous solution were added, at which time the temperature of the reaction mixture was adjusted to not exceed 10 ° C.

The reaction mixture was stirred at room temperature for about 5 hours and then distilled under reduced pressure to remove ethanol. The resultant was then extracted with 50 ml of ethyl acetate.

The combined organic layers were dried, filtered and distilled under reduced pressure to obtain 4- (4'-alkoxyphenylcarbonyloxy) benzaldehyde, which was yielded from 55 to 70%.

(3) 1- (4'-alkoxyphenylcarbonyloxy) phenyl-4-alkylisoxazolidine

1.3 mmol of 4- (4'-alkoxyphenylcarbonyloxy) benzaldoxim was dissolved in 30 ml of CHCl ₃ , followed by the addition of 1.36 mmol of N-chlorosuccinimide to complete dissolution.

The reaction mixture was stirred at rt for about 30 min and then a CHCl ₃ (5 mL) solution of olefin (1.36 mmol) was added dropwise. Then a solution of CHCl ₃ (3 mL) of triethylamine (1.43 mmol) was added dropwise over 10 minutes.

The reaction mixture was stirred for 2 hours to complete the reaction. Subsequently, 30 ml of distilled water and 50 ml of chloroform were added to the reaction mixture to separate the water layer and the organic layer, thereby extracting the chloroform layer.

The combined organic layers were dried, filtered and distilled under reduced pressure. The resulting product was recrystallized using ethyl acetate to obtain 1- (4'-alkoxyphenylcarbonyloxy) phenyl-4-alkylisoxazolidine (yield: 40-50%).

The phase form according to the temperature of said 1- (4'-alkoxyphenylcarbonyloxy) phenyl-4-alkylisoxazolidine is as follows.

C 111.5 ℃ S _C 116.5 ℃ S _a 162.4 ℃ N 162.8 I

Here, C represents a crystalline solid, S _C represents a smematic c phase, S _a represents a smematic a phase, N represents a nematic phase, and I represents an isotropic phase. At this time, the phase transition temperature and the liquid crystal phase were measured using a hot stage with a polarizing microscope.

Synthesis Example 3

Preparation of Biphenylisooxazolidine

(1) 4- (4'-alkylphenyl) benzyl alcohol

To anhydrous THF (20 mL) solution of lithium aluminum hydride (LAH, 8.6 mmol) was added dropwise anhydrous THF (10) mL) solution of ethyl 4- (4'-alkylphenyl) benzoate (3.6 mmol) for 25 minutes. The reaction mixture was cooled using an ice bath, then 10 ml of water was added to terminate the reaction.

The reaction mixture was extracted with 200 ml of ethyl acetate and the organic layer was dried and filtered. The resultant was distilled under reduced pressure, and column chromatography was carried out to obtain 4- (4'-alkylphenyl) benzyl alcohol (yield: 75%).

(2) 4- (4'-alkylphenyl) benzaldehyde

To a methylene chloride (40 mL) solution of pyridinium chlorochromate (PCC) (7.3 mmol) was added a solution of 4- (4'-alkylphenyl) benzyl alcohol (10 mL) of methylene chloride (10 mL) for 30 minutes. Added dropwise. The reaction mixture was stirred at rt for 5 h and then extracted with 250 ml of methylene chloride.

The combined organic layers were dried, filtered and distilled under reduced pressure. This product was subjected to column chromatography to obtain 4- (4'-alkylphenyl) benzaldehyde (yield: 90%).

(3) 4- (4'-alkylphenyl) benz aldoxime

3.51 mmol of 4- (4'-alkylphenyl) benzaldehyde was dissolved in 20 ml of ethanol and the reaction mixture was cooled using an ice bath. To the cooled reaction mixture, 10 ml of aqueous hydroxyamine hydrochloride (4.2 mmol) solution and 10 ml of aqueous sodium hydroxide (4.2 mmol) solution were added sequentially. At this time, the temperature of the reaction mixture was adjusted to not exceed 10 ° C.

The reaction mixture was stirred at room temperature for 5 hours and then distilled under reduced pressure to remove ethanol. Extracted with 500 ml of ethyl acetate, dried, filtered, and distilled under reduced pressure to obtain 4- (4'-alkylphenyl) benzaldehyde.

(4) 4-alkyl-1- (4'-alkylbiphenyl) isoxazolidine

3.6 mmol of 4- (4'-alkylphenyl) benzaldoxim was dissolved in 30 mL of CHCl ₃ , and then 3.6 mmol of N-chlorosuccinimide was added thereto to dissolve completely.

The reaction mixture was stirred for 30 minutes at room temperature, then a solution of CHCl ₃ (10 mL) of olefin (4.0 mmol) was added. Thereafter, a solution of CHCl ₃ (5 mL) of triethylamine (3. () mmol) was added dropwise to the reaction mixture for 10 minutes.

The reaction mixture was stirred for 2 hours, and then 30 ml of distilled water and 50 ml of chloroform were added to extract a chloroform layer. The combined organic layers were distilled under reduced pressure, and the resultant was recrystallized from ethyl acetate to obtain 4-alkyl-1- (4'-alkylbiphenyl) isoxazolidine (yield: 60%).

The phase form of the 4-alkyl-1- (4'-alkylbiphenyl) isooxazolidine according to the temperature is as follows.

C 152 ℃? 168 ° C I

(5) 4-amyl-4 '-(1-hydroxyethyl) biphenyl

A mixture of 0.017 mol of 4-acetyl-4'-amylbiphenyl, 0.025 mol of sodium borohydride and 10 ml of ethanol was refluxed for 5 hours.

Upon completion of the reaction, the reaction mixture was extracted with 50 ml of ethyl acetate. The ethyl acetate layer was distilled under reduced pressure and then recrystallized with ethanol to give 4-amyl-4 '-(1-hydroxyethyl) biphenyl (yield: 72%).

(6) 4-amyl-4'-vinylbiphenyl

A mixture of 0.70 g (2.36 mmol) of 4-amyl-4 '-(1-hydroxyethyl) biphenyl and 60 mL of 20% aqueous H ₂ SO ₄ solution was refluxed for 1 hour.

The reaction mixture was extracted with ethyl acetate and subjected to column chromatography to give 0.14 g of 4-amyl-4'-vinylbiphenyl (yield: 21%).

(7) heptaldoxime

0.18 mmol of alkyl aldehydes were dissolved in 50 mL of ethanol and the reaction mixture was cooled using an ice bath. 20 ml of aqueous hydroxyamine hydrochloride (0.20 mol) solution and 20 ml of sodium hydroxide (0.06 mol) aqueous solution were sequentially added to the reaction mixture. At this time, the temperature of the reaction mixture was adjusted so as not to exceed about 10 ° C.

The reaction mixture was stirred at room temperature for 5 hours and then distilled under reduced pressure to remove ethanol. The resulting product was extracted with 500 ml of ethyl acetate, then dried, filtered and distilled under reduced pressure to obtain hepta aldoxin (yield: 90%).

(8) 1-propyl-4- (4'-amylbiphenyl) isoxazolidine

1.8 mmol of heptaldoxime was dissolved in 30 mL of CHCl ₃ , and then 1.8 mmol of N-chlorosuccinimide was added thereto to completely dissolve it.

The reaction mixture was stirred for 30 minutes at room temperature, then a solution of CHCl ₃ (10 mL) of 4-amyl-4'-vinylbiphenyl (2 mmol) was added. Thereafter, a solution of CHCl ₃ (5 mL) of triethylamine (2.0 mmol) was added dropwise to the reaction mixture for 10 minutes.

The reaction mixture was stirred for 2 hours, and then 30 ml of distilled water and 50 ml of chloroform were added to extract a chloroform layer. The combined organic layers were distilled under reduced pressure and recrystallized with ethyl acetate to obtain 1-propyl-4- (4'-amylbiphenyl) isooxazolidine (yield: 35%).

Synthesis Example 4

Preparation of Cyclohexylphenylisoxazolidine

(1) 4- (4'-trans-amyloxycyclohexyl) benzaldehyde

0.017 mol of 4- (4'-trans-amylcyclohexyl) benzaldehyde was dissolved in 50 ml of ethanol and the reaction mixture was cooled using an ice bath.

10 ml of hydroxyamine hydrochloride (0.02 mol) aqueous solution and 20 ml of calcium carbonate (2.85 g, 0.02 mol) aqueous solution were sequentially added to the reaction mixture, at which time the temperature of the reaction mixture was adjusted not to exceed about 10 ° C. .

The reaction mixture was stirred at room temperature for 5 hours and then distilled under reduced pressure to remove ethanol. The resulting product was extracted with 500 ml of ethyl acetate, dried, filtered and distilled under reduced pressure to obtain 4- (4'-trans-amyloxycyclohexyl) benzaldehyde (yield: 73%).

(2) 4-propyl-1- (4 '-(4-amylcyclohexyl) phenyl) isoxazolidine

3.3 mmol of 4- (4′-trans-amyloxycyclohexyl) benzaldehyde was dissolved in 30 ml of CHCl ₃ , and 3.6 mmol of N-chlorosuccinimide was added thereto to dissolve completely.

The reaction mixture was stirred at room temperature for 30 minutes, then a solution of CHCl ₃ (10 mL) in heptene (3.94 mmol) was added. Thereafter, 0.38 g (3.8 mmol) of CHCl ₃ (10 mL) solution of triethylamine was added dropwise to the reaction mixture for 10 minutes.

The reaction mixture was stirred for 2 hours, and then 100 ml of distilled water and 100 ml of chloroform were added to extract a chloroform layer. The combined organic layers were distilled under reduced pressure and then recrystallized twice with ethyl acetate to obtain 4-propyl-1- (4 '-(4-amylcyclohexyl) phenyl) isoxazolidine (yield: 35%).

The phase form according to the temperature of the 4-propyl-1- (4 '-(4-amylcyclohexyl) phenyl) isooxazolidine is as follows.

C 156 ℃? 172 ℃ I

It was found that the temperature of transition from the crystalline solid to the smectic phase of the liquid crystal compound prepared according to the synthesis example was lower than in the conventional case.

The isoxazolidine ring-containing liquid crystal compound according to the present invention is chemically stable, and it is very easy to form a smectic phase because of the low temperature transition from the crystalline solid to the smectic phase. These liquid crystal compounds are not only used as components of the liquid crystal composition, but also used to synthesize other kinds of liquid crystal compounds as synthetic intermediates.

In addition, the liquid crystal composition containing the liquid crystal compound according to the present invention can be very usefully applied to various liquid crystal display devices by appropriately adjusting birefringence, dielectric anisotropy, and the like.

Claims (7)

Ioxoxazolidine ring-containing liquid crystal compound of Formula 1: Wherein at least one of R ₁ and R ₂ is a group represented by the following structural formula, Wherein Z ₁ is COO, OOC, CH ₂ CH ₂ , OCH ₂ , CH ₂ O, C≡C, CH = CH or CH ₂ , X ₁ , X ₂ , X ₃ , X ₄ , X ₅ , X ₅ , X ₇ and X ₈ , regardless of each other, are H, F or Cl, R ₃ is C _n H _{2n + 1} , OC _n H _{2n + 1} , SC _n H _{2n + 1} , C (= O) C _n H _{2n + 1} , OOC-C _n H _{2n + 1} , COOC _n H _{2n + 1} , or NHC _n H _{2n + 1} , where n is an integer from 1-12; The remaining R ₁ or R ₂ is unsubstituted C ₁ ~C ₁₂ straight-chain or branched alkyl, F, Cl, Br, CF 3, OCF 3 and substituted with at least one substituent selected from C ₁ ~C ₁₂ straight-CN A chain or branched alkyl group, provided that one -CH ₂ -or two non-adjacent -CH ₂ -is -O-, -S-, -CO-, -OCO-, -COO-, -OCS-,- Substituted by COS- and -CH = CH- and having -CH = CH ₂ and / or -CH = C (CH ₃ ) ₂ as a terminal group), a cyclohexyl group, a phenyl group, 4 -An alkylcyclohexyl group, a 4-alkylphenyl group, or a 4-alkoxyphenyl group, provided that the alkyl group is a C ₁ to C ₆ alkyl group. The method of claim 1, wherein at least one of R ₁ and R ₂ is (Wherein Z ₃ is a chemical bond, an oxygen atom, a sulfur atom or a carboxyl group, and R ₄ is a C ₆ to C ₁₂ straight or branched saturated alkyl group) Isooxazolidine ring-containing liquid crystal compound, characterized in that selected from the group consisting of. The isooxazolidine ring-containing liquid crystal compound according to claim 1, wherein the liquid crystal compound is a compound represented by the formula (2). In the above formula, Y ₁ and Y ₂ are C _n H _{2n + 1} (n is a number from 1 to 8) irrespective of each other. The isoxoxazolidine ring-containing liquid crystal compound according to claim 1, wherein the liquid crystal compound is a compound represented by Chemical Formula 3. In the above formula, Y ₃ and Y ₄ are C _n H _{2n + 1} (n is a number from 1 to 8) irrespective of each other. The isoxoxazolidine ring-containing liquid crystal compound according to claim 1, wherein the liquid crystal compound is a compound represented by Chemical Formula 4 or 5. In the above formula, Y ₅ and Y ₆ are C _n H _{2n + 1} (n is a number from 1 to 8) irrespective of each other. The isoxoxazolidine ring-containing liquid crystal compound according to claim 1, wherein the liquid crystal compound is a compound represented by Chemical Formula 6. In the above formula, Y ₇ and Y ₈ are C _n H _{2n + 1} (n is a number from 1 to 8) irrespective of each other. The liquid crystal composition containing the isooxazolidine ring containing liquid crystal compound as described in any one of Claims 1-6.