Liquid crystal compound and use thereof

Abstract

The present application relates to a novel liquid crystal compound and a use thereof. The novel liquid crystal compounds of the present application can exhibit a smectic A phase over a wide temperature range. The novel liquid crystal compounds of the present application can be usefully used in the technical fields to which smectic A liquid crystals can be applied, for example, bistable devices.

Claims

1. A liquid crystal compound of the following Formula 1: ##STR00018## in said Formula 1, R.sub.1 to R.sub.4 are each independently an alkyl group having 1 to 3 carbon atoms, R.sub.5 is F, Cl, Br, OF.sub.3, NCS, CN or OCH.sub.3, X is CH.sub.2 or O, k is an integer of 0 to 9, l is an integer of 0 to 2, m is an integer of 2 to 13, Y.sub.1 to Y.sub.8 are each independently CH, CF or N, where CF of Y.sub.1 to Y.sub.8 is not more than 2, A is the following Formula 2, or a single bond, O, S, CO, COO, OCO, SCO, COS, OCOO, CONR.sup.0, NR.sup.0CO, NR.sup.0CONR.sup.00, NR.sup.0COO, OCONR.sup.0, OCH.sub.2, OCH.sub.2, SCH.sub.2, CH.sub.2S, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, CH.sub.2CH.sub.2, (CH.sub.2).sub.4, CF.sub.2CH.sub.2, CH.sub.2CHF.sub.2, CHN, NCH, NHNH, NN, CHCR.sup.0, CY.sup.1CY.sup.2, CC, CHCHCOO or OCOCHCH, where R.sup.0, R.sup.00, Y.sup.1 and Y.sup.2 are each independently H or CH.sub.3; ##STR00019## in said Formula 2, Z.sub.1 and Z.sub.2 are each independently CH or N, and when said Z.sub.1 and Z.sub.2 are each CH, at least one of Y.sub.1 to Y.sub.8 is N, and wherein when A is not a heterocyclic structure then at least one of Y.sub.1 to Y.sub.8 is N.

2. The liquid crystal compound according to claim 1, wherein in said Formula 1, R.sub.1 to R.sub.4 are a methyl group.

3. The liquid crystal compound according to claim 1, wherein in said Formula 1, R.sub.5 is CN.

4. The liquid crystal compound according to claim 1, wherein in said Formula 1, k is an integer of 0 to 3.

5. The liquid crystal compound according to claim 1, wherein in said Formula 1, l is 0 or 1.

6. The liquid crystal compound according to claim 1, wherein in said Formula 1, m is an integer of 7 to 9.

7. The liquid crystal compound according to claim 1, wherein in said Formula 1, A is a single bond, any one of Y.sub.1 to Y.sub.8 is N and the remainder are CH.

8. The liquid crystal compound according to claim 1, wherein in said Formula 1, A is Formula 2, Z.sub.1 and Z.sub.2 are CH, any one of Y.sub.1 to Y.sub.8 is N and the remainder are CH.

9. The liquid crystal compound according to claim 1, wherein in said Formula 1, A is Formula 2, Z.sub.1 and Z.sub.2 are N, and Y.sub.1 to Y.sub.8 are each CH.

10. The liquid crystal compound according to claim 1, wherein said liquid crystal compound of Formula 1 has a structure represented by the following formulas a-1 to a-18: ##STR00020## ##STR00021## ##STR00022##

11. The liquid crystal compound according to claim 1, wherein the liquid crystal compound exhibits a smectic A phase in a temperature range of 20 C. to 100 C.

12. The liquid crystal compound according to claim 1, wherein the liquid crystal compound has a dielectric anisotropy of 1.0 to 20.

13. A bistable device comprising the liquid crystal compound of claim 1.

14. The bistable device according to claim 13, comprising two electrode substrates disposed opposite to each other and a liquid crystal layer containing the liquid crystal compound of claim 1 and a charging substance between said two electrode substrates.

Description

BRIEF DESCRIPTION OF THE DRAWING

(1) FIG. 1 is the results of evaluating the smectic A phase temperature range of Example 1.

DETAILED DESCRIPTION OF THE INVENTION

(2) Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present application is not limited by the contents set forth below.

<Preparation Example 1> Preparation of Compound of Formula a-1

(3) The compound of Formula a-1 was prepared according to the following reaction scheme.

(4) ##STR00006##

(5) Specifically, the compound A (12.0 g, 69.0 mmol) and the compound B (10.1 g, 69.0 mmol) were completely dissolved in tetrahydrofuran (200 ml), and then 3M potassium carbonate aqueous solution (100 ml) was added thereto and tetrakistriphenyl-phosphinopalladium (800 mg, 0.69 mmol) was added thereto, followed by heating and stirring for 4 hours. After the temperature was lowered to room temperature and the reaction was terminated, the reactant was adjusted to pH 23 with concentrated hydrochloric acid and the organic layer was separated and treated with magnesium sulfate. After filtration and concentration, the compound of Formula C (9.8 g, yield 72%) was prepared and used in the next reaction without further purification process.

(6) The compound C (9.8 g, 50.0 mmol) and the compound D (17.0 g, 50.0 mmol) were dissolved in 2-butanone (160 mL), and then potassium carbonate (13.8 g, 100.0 mmol) and potassium iodide (830 mg, 5.0 mmol) were added thereto and the mixture was refluxed and stirred. After 12 hours, water (160 ml) and ethyl acetate (160 ml) were added thereto and the organic layer was separated and washed with brine and then treated with magnesium sulfate. After filtration, the filtrate was concentrated, and purified by a final column chromatography (hexane/EA=5/1) to prepare the compound of Formula a-1 (18.7 g, yield 82.5%).

(7) MS [M+H].sup.+=455

<Preparation Example 2> Preparation of Compound of Formula a-2

(8) The compound of Formula a-2 was prepared according to the following reaction scheme.

(9) ##STR00007##

(10) Specifically, the compound of Formula F was prepared in the same method as the method of preparing the compound C of Preparation Example 1, except that the compound E was used instead of the compound A.

(11) The compound of Formula a-2 was prepared in the same method as the method of preparing the compound of Formula a-1 in Preparation Example 1, except that the compound F was used instead of the compound C.

(12) MS [M+H].sup.+=455

<Preparation Example 3> Preparation of Compound of Formula a-3

(13) The compound of Formula a-3 was prepared according to the following reaction scheme.

(14) ##STR00008##

(15) Specifically, the compound of Formula I was prepared in the same method as the method of preparing the compound C of Preparation Example 1, except that the compound G was used instead of the compound A and the compound H was used instead of the compound B.

(16) The compound of Formula a-3 was prepared in the same method as the method of preparing the compound of Formula a-1 in Preparation Example 1, except that the compound I was used instead of the compound C.

(17) MS [M+H].sup.+=455

<Preparation Example 4> Preparation of Compound of Formula a-4

(18) The compound of Formula a-4 was prepared according to the following reaction scheme.

(19) ##STR00009##

(20) Specifically, the compound of Formula K was prepared in the same method as the method of preparing the compound C of Preparation Example 1, except that the compound G was used instead of the compound A and the compound J was used instead of the compound B.

(21) The compound of Formula a-4 was prepared in the same method as the method of preparing the compound of Formula a-1 in Preparation Example 1, except that the compound K was used instead of the compound C.

(22) MS [M+H].sup.+=455

<Preparation Example 5> Preparation of Compound of Formula a-5

(23) The compound of Formula a-5 was prepared according to the following reaction scheme.

(24) ##STR00010##

(25) Specifically, the compound of Formula a-5 was prepared in the same method as the method of preparing the compound of Formula a-1 in Preparation Example 1, except that the compound L was used instead of the compound D.

(26) MS [M+H].sup.+=497

<Preparation Example 6> Preparation of Compound of Formula a-6

(27) The compound of Formula a-6 was prepared according to the following reaction scheme.

(28) ##STR00011##

(29) Specifically, the compound of Formula a-6 was prepared in the same method as the method of preparing the compound of Formula a-1 in Preparation Example 1, except that the compound M was used instead of the compound D.

(30) MS [M+H].sup.+=423

<Preparation Example 7> Preparation of Compound of Formula a-10

(31) The compound of Formula a-10 was prepared according to the following reaction scheme.

(32) ##STR00012##

(33) Specifically, the compound of Formula O was prepared in the same method as the method of preparing the compound C, except that the compound N was used instead of the compound A.

(34) The compound P (43.4 g, 72.2 mmol) was completely dissolved in tetrahydrofuran (200 ml), and then 1.6M n-butyl lithium (45.1 ml) was added in drops thereto at 0 C. for 1 hour. After 30 minutes, the temperature was raised to room temperature and the reactant was stirred for 1 hour. The compound O (10.0 g, 48.1 mmol) was dissolved in tetrahydrofuran (50 mL) and added in drops thereto at 0 C. for 1 hour. The temperature was raised to room temperature and the reactant was stirred for 12 hours. After completing the reaction, the resultant was filtered, concentrated and purified by a column chromatography (hexane/EA=5/1) to synthesize a precursor of Formula a-10. This precursor was dissolved in ethyl acetate (200 mL), and then palladium/charcoal (1.0 g) was added thereto, a hydrogen balloon was hung, and the reactant was stirred for 12 hours. After completing the reaction, the filtrate filtered through a Celite pad was concentrated to prepare the compound of Formula a-10 (10.9 g, yield 50.0%).

(35) MS [M+H].sup.+=453

<Preparation Example 8> Preparation of Compound of Formula a-11

(36) The compound of Formula a-11 was prepared according to the following reaction scheme.

(37) ##STR00013##

(38) Specifically, the compound of Formula R was prepared in the same method as the method of preparing the compound C of Preparation Example 1, except that the compound Q was used instead of the compound A.

(39) The compound of Formula a-11 was prepared in the same method as the method of preparing the compound of Formula a-10 in Preparation Example 7, except that the compound R was used instead of the compound O.

(40) MS [M+H].sup.+=453

<Preparation Example 9> Preparation of Compound of Formula a-12

(41) The compound of Formula a-12 was prepared according to the following reaction scheme.

(42) ##STR00014##

(43) Specifically, the compound of Formula T was prepared in the same method as the method of preparing the compound C of Preparation Example 1, except that the compound S was used instead of the compound A and the compound H was used instead of the compound B.

(44) The compound of Formula a-12 was prepared in the same method as the method of preparing the compound of Formula a-10 in Preparation Example 7, except that the compound T was used instead of the compound O.

(45) MS [M+H].sup.+=453

<Preparation Example 10> Preparation of Compound of Formula a-13

(46) The compound of Formula a-13 was prepared according to the following reaction scheme.

(47) ##STR00015##

(48) Specifically, the compound of Formula U was prepared in the same method as the method of preparing the compound C of Preparation Example 1, except that the compound S was used instead of the compound A and the compound J was used instead of the compound B.

(49) The compound of Formula a-13 was prepared in the same method as the method of preparing the compound of Formula a-10 in Preparation Example 7, except that the compound U was used instead of the compound O.

(50) MS [M+H].sup.+=453

<Preparation Example 11> Preparation of Compound of Formula a-14

(51) The compound of Formula a-14 was prepared according to the following reaction scheme.

(52) ##STR00016##

(53) Specifically, the compound of Formula O was prepared in the same method as the method of preparing the compound C of Preparation Example 1, except that the compound N was used instead of the compound A.

(54) The compound of Formula a-14 was prepared in the same method as the method of preparing the compound of Formula a-10 in Preparation Example 7, except that the compound V was used instead of the compound P.

(55) MS [M+H].sup.+=495

<Preparation Example 12> Preparation of Compound of Formula a-15

(56) The compound of Formula a-15 was prepared according to the following reaction scheme.

(57) ##STR00017##

(58) Specifically, the compound of Formula O was prepared in the same method as the method of preparing the compound C of Preparation Example 1, except that the compound N was used instead of the compound A.

(59) The compound of Formula a-15 was prepared in the same method as the method of preparing the compound of Formula a-10 in Preparation Example 7, except that the compound W was used instead of the compound P.

(60) MS [M+H].sup.+=421

Evaluation Example 1: Evaluation of Smectic a Phase Temperature Range

(61) The smectic A phase temperature range was evaluated using the compounds prepared in Preparation Examples 1 to 12 as Examples 1 to 12, respectively, and the results were shown in Table 1 below. The smectic A phase temperature range was evaluated by observing the phase change by the differential scanning calorimetry (DSC) measurement and the polarized light microscopy. FIG. 1 is the results of evaluating the smectic A phase temperature range of Example 1.

(62) TABLE-US-00001 TABLE 1 Example Smectic A Temperature 1 0 C.~69 C. 2 12 C.~51 C. 3 21 C.~72 C. 4 1 C.~70 C. 5 15 C.~66 C. 6 8 C.~11 C. 7 5 C.~70 C. 8 8 C.~66 C. 9 19 C.~78 C. 10 14 C.~68 C. 11 20 C.~54 C. 12 7 C.~25 C.