STABILIZER AND LIQUID CRYSTAL COMPOSITION COMPRISING SAME

Abstract

Disclosed is a novel stabilizer represented by formula I,

##STR00001##

Further disclosed is a liquid crystal composition comprising a compound of formula I. The liquid crystal composition disclosed in the present invention has a low viscosity γ.sub.1, a moderate dielectric anisotropy Δ∈, a moderate optical anisotropy Δn, and most principally a high reliability, and can achieve a quick response of liquid crystal display.

Claims

1. A stabilizer represented by formula I: ##STR00070## wherein M represents cyclopentyl, cyclobutyl or cyclopropyl; Z.sub.1 and Z.sub.2 each independently represent a single bond, —CH.sub.2—, —CH.sub.2CH.sub.2—, —O—, —CH.sub.2O—, —OCH.sub.2— or —COO—; ##STR00071## represents one or two of ##STR00072## and n represents 0, 1 or 2.

2. The stabilizer according to claim 1, characterized in that said stabilizer represented by formula I is selected from the following structures: ##STR00073## wherein M represents cyclopentyl, cyclobutyl or cyclopropyl; ##STR00074## represents ##STR00075## and Z.sub.1 and Z.sub.2 each independently represent a single bond, —CH.sub.2—, —CH.sub.2CH.sub.2—, —O—, —CH.sub.2O—, —OCH.sub.2— or —COO—.

3. The stabilizer according to claim 2, characterized in that said stabilizer represented by formula I-a is selected from the following structures: ##STR00076## ##STR00077## ##STR00078## said stabilizer represented by formula I-b is selected from the following structures: ##STR00079## said stabilizer represented by formula I-c is selected from the following structures: ##STR00080## ##STR00081## ##STR00082##

4. A liquid crystal composition comprising a stabilizer of claim 1, characterized in that said liquid crystal composition comprises one or more of compounds represented by formulas II-1 to II-14: ##STR00083## ##STR00084## wherein R0, R0′, R1, R1′, R2, R2′, R3, R3′ each independently represent an alkyl group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, or an alkoxy group having a carbon atom number of 1-10, wherein any —CH.sub.2— can be substituted by —O—, and any hydrogen can be substituted by F; and the (F)s each independently represent H or F.

5. The liquid crystal composition according to claim 4, characterized in that in said liquid crystal composition, the total content in mass percentage of the compound represented by formula I is 0.001-5%; the total content in mass percentage of the compounds represented by formulas II-1 to II-10 is 1-60%; and the total content in mass percentage of the compounds represented by formulas II-11 to II-14 is 0-30%; wherein R0 and R2 each independently represent an alkyl group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5, and R1 and R3 each independently represent an alkyl or alkoxy group having a carbon atom number of 1-5.

6. The liquid crystal composition according to claim 4, characterized in that said liquid crystal composition is a positive liquid crystal composition and further comprises one or more compounds represented by formula III: ##STR00085## wherein R.sub.4 represents an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any one or more CH.sub.2 in R.sub.4 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl; ##STR00086## each independently represent one or two of ##STR00087## m represents 1 or 2; Z.sub.3 and Z.sub.4 each independently represent a single bond, —CF.sub.2O—, —CH.sub.2CH.sub.2— or —CH.sub.2O—; and Y.sub.2 represents F, a fluorinated alkyl group having a carbon atom number of 1-5, a fluorinated alkoxy group having a carbon atom number of 1-5, a fluorinated alkenyl group having a carbon atom number of 2-5, or a fluorinated alkenoxy group having a carbon atom number of 3-8.

7. The liquid crystal composition according to claim 6, characterized in that said one or more compounds represented by formula III are one or more of compounds represented by formulas III-1 to III-22: ##STR00088## ##STR00089## ##STR00090## wherein X.sub.1 and X.sub.2 each independently represent H or F, and cannot both be F or H; R.sub.4 each independently represents an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.4 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl; the (F)s each independently represent H or F; and Y.sub.2 each independently represents F, a fluorinated alkyl group having a carbon atom number of 1-5, a fluorinated alkoxy group having a carbon atom number of 1-5, a fluorinated alkenyl group having a carbon atom number of 2-5, or a fluorinated alkenoxy group having a carbon atom number of 3-8.

8. The liquid crystal composition according to claim 4, characterized in that said liquid crystal composition is a negative liquid crystal composition and further comprises one or more compounds represented by formula IV: ##STR00091## wherein R.sub.5 and R.sub.6 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.5 and R.sub.6 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl; Z.sub.5 and Z.sub.6 each independently represent a single bond, —CH.sub.2CH.sub.2—, —CH.sub.2O—; ##STR00092## each independently represent one of ##STR00093## m represents 1 or 2; and n represents 0, 1 or 2.

9. The liquid crystal composition according to claim 6, characterized in that said one or more compounds represented by formula IV are one or more of compounds represented by formulas IV-1 to IV-11: ##STR00094## wherein R.sub.5 and R.sub.6 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.5 and R.sub.6 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl.

10. The liquid crystal composition according to claim 4, characterized in that said liquid crystal composition is a negative liquid crystal composition and further comprises one or more compounds represented by formula V: ##STR00095## wherein R.sub.7 and R.sub.8 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.7 and R.sub.8 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl.

11. The liquid crystal composition according to claim 5, characterized in that said liquid crystal composition is a negative liquid crystal composition and further comprises one or more compounds represented by formula V: ##STR00096## wherein R.sub.7 and R.sub.8 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.7 and R.sub.8 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl.

12. The liquid crystal composition according to claim 6, characterized in that said liquid crystal composition is a negative liquid crystal composition and further comprises one or more compounds represented by formula V: ##STR00097## wherein R.sub.7 and R.sub.8 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.7 and R.sub.8 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl.

13. The liquid crystal composition according to claim 7, characterized in that said liquid crystal composition is a negative liquid crystal composition and further comprises one or more compounds represented by formula V: ##STR00098## wherein R.sub.7 and R.sub.8 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.7 and R.sub.8 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl.

14. The liquid crystal composition according to claim 8, characterized in that said liquid crystal composition is a negative liquid crystal composition and further comprises one or more compounds represented by formula V: ##STR00099## wherein R.sub.7 and R.sub.8 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.7 and R.sub.8 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl.

15. The liquid crystal composition according to claim 9, characterized in that said liquid crystal composition is a negative liquid crystal composition and further comprises one or more compounds represented by formula V: ##STR00100## wherein R.sub.7 and R.sub.8 each independently represent an alkyl group having a carbon atom number of 1-10, a fluorinated alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluorinated alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluorinated alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluorinated alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in R.sub.7 and R.sub.8 may be substituted by cyclopentyl, cyclobutyl or cyclopropyl.

16. A liquid crystal display element or liquid crystal display comprising the liquid crystal composition of claim 4, characterized in that said liquid crystal display element or liquid crystal display is an active matrix display element or display or a passive matrix display element or display.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0061] FIG. 1 is a mass spectrum of a compound represented by formula I-a-1; and

[0062] FIG. 2 is a mass spectrum of a compound represented by formula I-b-1.

DESCRIPTION OF EMBODIMENTS

[0063] The present invention is further described in conjunction with particular examples below, and the present invention is not limited to the following examples. Said methods are all conventional methods, unless otherwise specified. Said raw materials can all be obtained from disclosed commercial approaches, unless otherwise specified. Said percentages are all mass percentages, unless otherwise specified.

[0064] In the following examples,

[0065] CP represents a clearing point, directly determined by WRX-1S microscopic thermal analyzer, with a temperature rate set to be 3° C./min.

[0066] Δn represents an optical anisotropy (589 nm, 20° C.),

[0067] Δ∈ represents a dielectric anisotropy (25° C., 1 KHz, HP4284A, 5.2 micron TN levorotary box),

[0068] γ.sub.1 represents a rotary viscosity (mPa.Math.s) at 20° C., VHR (%) represents a charge retention ratio (5 V, 60 Hz, 20° C.), and ρ(×10.sup.13Ω.Math.cm) represents electrical resistivity (at 20° C.).

[0069] Testers for the charge retention ratio VHR (%) and the electrical resistivity ρ(×10.sup.13Ω.Math.cm) are both TOYO06254 and TOYO6517-type liquid crystal physical property evaluation systems (at a test temperature of 20° C., a time of 16 ms, and a test box of 7.0 microns).

[0070] In the reaction process, the reaction progress is generally monitored by means of TLC, and treatments after the completion of the reaction are generally water washing, extraction, organic phase combination and drying, solvent evaporation under reduced pressure, as well as recrystallization and column chromatography; and a person skilled in the art would be able to implement the present invention according to the following description.

[0071] In the examples of the present invention application, liquid crystal monomer structures are represented by codes, wherein the code representation methods of cyclic structures, end groups and linking groups of the liquid crystals are shown in tables (I) and (II) below

TABLE-US-00001 TABLE (I) Codes corresponding to cyclic structures Cyclic structures Corresponding codes [00030] C [00031] B [00032] B(3F) [00033] B(3F, 5F) [00034] B(2F) [00035] B(2F, 3F) [00036] C[3O] [00037] C[3O, 5O] [00038] Sa

TABLE-US-00002 TABLE (II) Codes corresponding to end groups and linking groups End groups and linking groups Corresponding codes C.sub.nH.sub.2n+1— n- C.sub.nH.sub.2n+1O— nO— —OCF.sub.3 —OCF.sub.3 —CF.sub.2O— —CF.sub.2O— —F —F —CN —CN —CH.sub.2CH.sub.2— —E— —CH═CH— —V— —C≡C— —W— —COO— —COO— —CH═CH—C.sub.nH.sub.2n+1 Vn— [00039] C(5)— [00040] C(4)— [00041] C(3)—

EXAMPLES

[0072] ##STR00042##

Route:

[0073] ##STR00043##

Example 1

[0074] ##STR00044##

[0075] Route:

##STR00045##

[0076] Operation Procedure:

[0077] To a 2 L three-necked flask, 4-cyclopentyl cyclohexyl phenol (95 g, 0.389 mol) and 500 ml of petroleum ether are added and stirred for 5 min, 39 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (151 g, 2.04 mol) and 100 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 300 ml of water and 1 L of EA are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 3 times, 57 g is obtained, with GC: 99.88% and a yield of 40%.

Example 2

[0078] ##STR00046##

[0079] Route:

##STR00047##

[0080] To a 2 L three-necked flask, 4-(5′-cyclobutyltetrahydropyrane)phenol (93 g, 0.4 mol) and 500 ml of petroleum ether are added and stirred for 5 min, 39 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (151 g, 2.04 mol) and 100 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 300 ml of water and 1 L of ethyl acetate are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 4 times, 50 g is obtained, with GC: 99.66% and a yield of 35%.

Example 3

[0081] ##STR00048##

[0082] Route:

##STR00049##

[0083] To a 1 L three-necked flask, 4-(5′-cyclopropyl-1′,3′-dioxane)phenol (44 g, 0.2 mol) and 300 ml of petroleum ether are added and stirred for 5 min, 20 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (74 g, 1 mol) and 50 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 200 ml of water and 500 mL of ethyl acetate are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 4 times, 33 g is obtained, with GC: 99.5% and a yield of 50%.

Example 4

[0084] ##STR00050##

[0085] Route:

##STR00051##

[0086] To a 1 L three-necked flask, 4′-cyclopentyl-4-hydroxy-1,1′-biphenyl (47.6 g, 0.2 mol) and 300 ml of petroleum ether are added and stirred for 5 min, 20 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (74 g, 1 mol) and 50 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 200 ml of water and 500 mL of ethyl acetate are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 4 times, 60 g is obtained, with GC: 99.9% and a yield of 85%.

Example 5

[0087] ##STR00052##

[0088] Route:

##STR00053##

[0089] To a 2 L three-necked flask, 4-cyclopropylphenol (53.6 g, 0.4 mol) and 500 ml of petroleum ether are added and stirred for 5 min, 39 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (151 g, 2.04 mol) and 100 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 300 ml of water and 1 L of ethyl acetate are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 3 times, 40 g is obtained, with GC: 99.6% and a yield of 40%.

Example 6

[0090] ##STR00054##

[0091] Route:

##STR00055##

[0092] To a 1 L three-necked flask, 4-(cyclopentyloxy)phenol (35.6 g, 0.2 mol) and 300 ml of petroleum ether are added and stirred for 5 min, 20 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (74 g, 1 mol) and 50 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 200 ml of water and 500 mL of ethyl acetate are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 4 times, 29 g is obtained, with GC: 99.75% and a yield of 50%.

Example 7

[0093] ##STR00056##

[0094] To a 1 L three-necked flask, 4-(cyclopentylmethoxy)phenol (38.4 g, 0.2 mol) and 300 ml of petroleum ether are added and stirred for 5 min, 20 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (74 g, 1 mol) and 50 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 200 ml of water and 500 mL of ethyl acetate are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 4 times, 27.4 g is obtained, with GC: 99.65% and a yield of 45%.

Example 8

[0095] ##STR00057##

[0096] To a 2 L three-necked flask, 4-cyclobutylethylphenol (70.4 g, 0.4 mol) and 500 ml of petroleum ether are added and stirred for 5 min, 39 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (151 g, 2.04 mol) and 100 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 300 ml of water and 1 L of ethyl acetate are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 3 times, 48.4 g is obtained, with GC: 99.7% and a yield of 42%.

Example 9

[0097] ##STR00058##

[0098] To a 2 L three-necked flask, 4-cyclopropylmethylphenol (59.2 g, 0.4 mol) and 500 ml of petroleum ether are added and stirred for 5 min, 39 g of concentrated sulfuric acid is added, the temperature is raised to 70° C. (in a water bath), a mixed liquid of tert-butyl alcohol (151 g, 2.04 mol) and 100 ml of petroleum ether are added dropwise for an addition time of 2 h, the temperature is controlled at 70-72° C., and after the completion of the addition, the temperature is maintained for 4 h; and liquid separation is directly carried out to separate sulfuric acid, 300 ml of water and 1 L of ethyl acetate are added and stirred for 5 min, liquid separation is carried out, the organic phase is directly dried in a rotary manner, the product is dissolved under heat in 1 fold of petroleum ether and 3 folds of ethanol, chilled in a refrigerator for 6 hours, and subjected to suction filtration, and after repeated crystallization 3 times, 41.6 g is obtained, with GC: 99.6% and a yield of 40%.

[0099] The following liquid crystal compositions are used as matrix MUTY

TABLE-US-00003 Liquid crystal monomer codes Content (%) 3CCV 10 2CCB(3F)O1 6 2CCBO1 6 1BB5 8 3CBO2 6 3CCB(3F)2 6 3CCB2 5 2CCB(3F,4F) 12 2CCBOCF3 8 C(5)BB(3F,5F)CF.sub.2OB(3F,4F,5F) 17 C(5)C(3O)BB(3F,5F)CF.sub.2OB(3F,4F,5F) 6 3CCBB(3F,4F) 5 2CBB(2F)B3 5

[0100] 500 ppm of stabilizers with different structures are added respectively, after the perfusion into a liquid crystal cell, a UV irradiation (5000 mJ) experiment is carried out, a preservative experiment of maintaining at a high heat of 120° C. for three hours is carried out, and the VHR data thereof are tested, as follows for comparison:

TABLE-US-00004 VHR (%, 5 V, 60 Hz) Sample name Initial After high temperature MUTY 99.83 99.22 MUTY + BHT 99.77 99.57 MUTY + T001 99.78 99.28 MUTY + I-a-1 99.80 99.77 MUTY + I-b-1 99.79 99.76 MUTY + I-a-9 99.76 99.68 MUTY + I-a-16 99.77 99.72 MUTY + I-c-11 99.77 99.65

[0101] wherein BHT represents

##STR00059##

and

[0102] T001 represents

##STR00060##

[0103] It can be seen from the above table that the stabilizer provided by the present invention, having a greater advantage with respect to the prior art, can provide better thermal resistance for a mixed liquid crystal, so as to provide a better guarantee for satisfying increasingly high reliability requirements of mixed liquid crystals for TFT display.

[0104] The compounds represented by formula I provided by the examples of the present invention, as additives applied to liquid crystal compositions, are added additionally into the components of the liquid crystal compositions, for example, the addition of 1% of formula I-a-1 is represented as follows:

[0105] Other components: 100%, and

[0106] Formula I-a-1: 1%.

Example 10

[0107]

TABLE-US-00005 Content Category Liquid crystal monomer codes (%) II 3CCV 10 II 2CCB(3F)O1 6 II 2CCBO1 6 II 1BB5 8 II 3CBO2 6 II 3CCB(3F)2 6 II 3CCB2 5 III 2CCB(3F, 4F) 12 III 2CCBOCF3 8 III C(5)BB(3F, 5F)CF.sub.2OB(3F, 4F, 5F) 17 III C(5)C(3O)BB(3F, 5F)CF.sub.2OB(3F, 4F, 5F) 6 III 3CCBB(3F, 4F) 5 III 2CBB(2F)B3 5 I [00061] 0.03 Δε [1 KHz, 20° C.]: 8.4 Δn [589 nm, 20° C.]: 0.12 Cp: 108° C. γ.sub.1: 99 mPa.s.

Example 11

[0108]

TABLE-US-00006 Content Category Liquid crystal monomer codes (%) II 3CC2 23 II 3CCV1 12 II 3CCB(2F)2 4 II 3CCB2 3 II 3CCB(3F)2 4 II 3CBB2 4 III 2CCB(3F, 4F, 5F) 9 III 2CBB(3F, 4F, 5F) 8 II V2CCB1 10 III C(3)1BBB(3F, 5F)CF.sub.2OB(3F, 4F, 5F) 17 III 4BB(3F)B(3F, 5F)CF.sub.2OB(3F, 4F, 5F) 6 I [00062] 1 Δε [1 KHz, 20° C.]: 7.0 Δn [589 nm, 20° C.]: 0.09 Cp: 62° C. γ.sub.1: 70 mPa.s.

Example 12

[0109]

TABLE-US-00007 Content Category Liquid crystal monomer codes (%) II-B 3CC2 20 II-B 3CCV 18 II 3CBO2 2 II VCCB(3F)2 5 II VCCB1 5 III 2CCB(3F, 4F) 12 III 2CBBOCF3 8 III C(3)1BB(3F, 5F)CF.sub.2OB(3F, 4F, 5F) 17 III 3BB(3F, 5F)BCF.sub.2OB(3F, 4F, 5F) 6 II 3CBBC3 7 I [00063] 0.05 Δε [1 KHz, 20° C.]: 6.3 Δn [589 nm, 20° C.]: 0.090 Cp: 81° C. γ.sub.1: 81 mPa.s.

Example 13

[0110]

TABLE-US-00008 Content Category Liquid crystal monomer codes (%) II 3CC2 30 II 3CCV 20 II VCCB(3F)2 2 II V2CCB1 3 III 5BBB(2F, 4F) 13 III C(5)BB(3F, 5F)CF.sub.2OB(3F, 4F, 5F) 17 III C(5)BB(3F)B(3F, 5F)CF.sub.2OB(3F, 4F, 5F) 6 III C(5)BBB(3F)B(3F, 4F, 5F) 1 1928 III C(5)CBB(3F)B(3F, 4F, 5F)1912 3 III 3CBB(3F, 5F)BOCF3 5 I [00064] 5 Δε [1 KHz, 20° C.]: 6.9 Δn [589 nm, 20° C.]: 0.115 Cp: 72° C. γ.sub.1: 79 mPa.s.

Example 14

[0111]

TABLE-US-00009 Content Category Liquid crystal monomer codes (%) II 3CC2 5 II 3CCV 45 II 3CBB2 5 II V2CBB(3F)3 5 III 5BBB(2F, 4F) 8 III C(5)BB(3F, 5F)CF.sub.2OB(3F, 4F, 5F) 17 III 5BB(3F, 5F)BCF.sub.2OB(3F, 4F, 5F) 6 III H(5)BBB(3F)B(3F, 4F, 5F) 1 IV 3CBB(2F, 3F)O2 3 III 3CBB(3F, 5F)BCF3 5 I [00065] 0.05 Δε [1 KHz, 20° C.]: 6.5 Δn [589 nm, 20° C.]: 0.11 Cp: 72° C. γ.sub.1: 75 mPa.s.

Example 15

[0112]

TABLE-US-00010 Content Category Liquid crystal monomer codes (%) II 3CC2 10 II 3CCB(3F)O1 6 II 3CCBO1 6 II 1BB5 8 II 3CBO2 6 II 3CCB(3F)2 5 II 3CBB1 6 IV 3CBB(2F, 3F)O2 8 IV 2CBB(2F, 3F)O2 12 IV 3C1OB(2F, 3F)O2 10 IV C(5)BB(2F, 3F)O2 10 III 5BBB(2F, 4F) 13 I [00066] 0.1 Δε [1 KHz, 20° C.]: −3.4 Δn [589 nm, 20° C.]: 0.12 Cp: 76° C. γ.sub.1: 95 mPa.s.

Example 16

[0113]

TABLE-US-00011 Content Category Liquid crystal monomer codes (%) II 3CC2 23 II 3CCV1 12 III 5BBB(2F, 4F) 7 III 3BBB(2F, 4F) 7 II 2CBB2 9 II 3CBB2 5 IV 3CB(2F, 3F)BO2 8 IV 2CBB(2F, 3F)O2 12 IV 3C1OB(2F, 3F)O2 10 IV C(5)1OSaO4 6 I [00067] 0.02 Δε [1 KHz, 20° C.]: −3.0 Δn [589 nm, 20° C.]: 0.115 Cp: 97° C. γ.sub.1: 110 mPa.s.

Example 17

[0114]

TABLE-US-00012 Content Category Liquid crystal monomer codes (%) II 3CC2 20 II 3CCV 18 II 3CBO2 2 II VCCB1 10 IV 3CCB(2F, 3F)O2 8 IV 2CB(2F, 3F)B(3F)O2 12 IV 3C1OB(2F, 3F)O2 10 IV C(5)BB(2F, 3F)O2 10 IV 3CB(2F, 3F)O2 10 I [00068] 0.005 Δε [1 KHz, 20° C.]: −3.5 Δn [589 nm, 20° C.]: 0.08 Cp: 60° C. γ.sub.1: 90 mPa.s.

Example 18

[0115]

TABLE-US-00013 Content Category Liquid crystal monomer codes (%) II 3CC2 30 II 3CCV 20 II VCCBO2 2 II V2CCB(3F)3 3 IV VCCB(2F, 3F)O2 8 IV 2CBB(2F, 3F)O2 12 IV 3C1OB(2F, 3F)O2 10 IV C(5)CB(2F, 3F)O2 10 IV 3CB(2F, 3F)O2 5 I [00069] 0.3 Δε [1 KHz, 20° C.]: −3.0 Δn [589 nm, 20° C.]: 0.08/ Cp: 60° C. γ.sub.1: 82 mPa.s.

[0116] It can be seen from the above examples that the liquid crystal composition of the present invention has a lower rotary viscosity γ.sub.1, is used for liquid crystal display, can achieve a quick response, and further has a moderate dielectric anisotropy Δ∈, a moderate optical anisotropy Δn, and a high stability to heat. It is especially suitable for liquid crystal materials for TN, IPS, and VA modes.