LIQUID CRYSTAL COMPOUND CONTAINING 2,3,4-TRISUBSTITUTED BENZENE AND COMPOSITION THEREOF

Abstract

Provided is a liquid crystal compound containing 2,3,4-trisubstituted benzene, a liquid crystal composition thereof, and a liquid crystal display element or a liquid crystal display comprising the liquid crystal compound or the liquid crystal composition, wherein the liquid crystal composition has a lower viscosity, can achieve a quick response, and further has a moderate dielectric anisotropy , a moderate optical anisotropy n, and high stability to heat and light. The liquid crystal display element or liquid crystal display comprising the liquid crystal composition has the properties of a wider nematic phase temperature range, an appropriate birefringence anisotropy, a very high electrical resistivity, a good ultraviolet resistant property, a high charge retention rate, a low vapor pressure etc., and particularly, the liquid crystal compound or the liquid crystal composition has the advantage of a high light transmittance.

Claims

1. A liquid crystal composition, wherein the liquid crystal composition comprises one or more compounds of formula I and one or more compounds of formula II, and said liquid crystal composition at least further comprises one or two compounds of formula II-B included in formula II, ##STR00057## wherein R.sub.0, R.sub.1 and R.sub.3 each independently represent an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any one or more non-connected CH.sub.2 in the groups represented by R.sub.o, R.sub.1 and R.sub.3 may be substituted with cyclobutyl, cyclopropyl or O; Y represents ethyl or vinyl; R.sub.2 represents F, OCF.sub.3, OCHF.sub.2 or OCH.sub.2F; ##STR00058## each independently represent one of ##STR00059## and any fluorobenzene; and m and n each independently represent 1 or 2.

2. The liquid crystal composition according to claim 1, wherein said one or more compounds represented by formula I are one or more of compounds represented by formulas I1 to I14; said one or more compounds represented by formula II comprise one or more compounds represented by formulas II1 to II10; and said one or two compounds represented by formula are one or two of compounds represented by formulas II-B-1 and II-B-2; ##STR00060## ##STR00061## ##STR00062## ##STR00063## wherein R.sub.11 each independently represents an alkyl having a carbon atom number of 1-6 or an alkenyl group having an atom number of 2-6.

3. The liquid crystal composition according to claim 1, wherein in said liquid crystal composition, the total content in mass percentage of the compounds represented by formula I is 0.5-50%, the total content in mass percentage of the compounds represented by formula II-B is 5-65%, and the total content in mass percentage of the compounds represented by formula II except the compounds represented by formula II-B is 0-30%.

4. The liquid crystal composition according to claim 1, wherein said liquid crystal composition is a positive liquid crystal composition, and said liquid crystal composition further comprises one or more compounds represented by foiinula III ##STR00064## wherein R.sub.4 represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8; and any one or more CH.sub.2 in the groups represented by R.sub.4 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl; ##STR00065## each independently represent: one or two of ##STR00066## m represents 1 or 2; Z.sub.1 and Z.sub.2 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 fluoro-substituted alkyl group having a carbon atom number of 1-5, a fluoro-substituted alkoxy group having a carbon atom number of 1-5, a fluoro-substituted alkenyl group having a carbon atom number of 2-5, or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8.

5. The liquid crystal composition according to claim 4, wherein said one or more compounds represented by formula III are one or more of compounds represented by formulae III1 to III26 ##STR00067## ##STR00068## ##STR00069## wherein X.sub.1 and X.sub.2 each independently represent H or F, but can be neither F nor H at the same time in the same molecular formula; R.sub.4 each independently represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in the groups represented by R.sub.4 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl; the (F)s each independently represent H or F; and Y.sub.2 each independently represents F, a fluoro-substituted alkyl group having a carbon atom number of 1-5, a fluoro-substituted alkoxy group having a carbon atom number of 1-5, a fluoro-substituted alkenyl group having a carbon atom number of 2-5, or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8.

6. The liquid crystal composition according to claim 1, wherein said liquid crystal composition is a negative liquid crystal composition, and said liquid crystal composition further comprises one or more compounds represented by formula IV ##STR00070## wherein R.sub.5 and R.sub.6 each independently represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in the groups represented by R.sub.5 and R.sub.6 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl; Z.sub.3 and Z.sub.4 each independently represent a single bond, CH.sub.2CH.sub.2 or CH.sub.2O; ##STR00071## each independently represent one or more of ##STR00072## m represents 1 or 2; n represents 0, 1 or 2.

7. The liquid crystal composition according to claim 6, wherein said one or more compounds represented by formula IV are one or more of compounds represented by formulae IV1 to IV11 ##STR00073## wherein R.sub.5 and R.sub.6 each independently represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in the groups represented by R.sub.5 and R.sub.6 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl.

8. The liquid crystal composition according to claim 1, wherein said liquid crystal composition is a negative liquid crystal composition, and said liquid crystal composition further comprises one or more compounds represented by formula V ##STR00074## wherein R.sub.7 and R.sub.8 each independently represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any CH.sub.2 in the groups represented by R.sub.7 and R.sub.8 may be substituted with cyclopentyl, cyclobutyl or cyclopropyl.

9. The liquid crystal composition according to claim 4, wherein said liquid crystal composition further comprises one or more compounds represented by formula VI ##STR00075## wherein R.sub.91 represents an alkyl group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; R.sub.92 represents an alkyl group having a carbon atom number of 1-5, an alkoxy group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; and ##STR00076## represents ##STR00077##

10. A liquid crystal compound represented by formula I-A, ##STR00078## wherein R.sub.1 represents an alkyl group having a carbon atom number of 1-10, a fluoro-substituted alkyl group having a carbon atom number of 1-10, an alkoxy group having a carbon atom number of 1-10, a fluoro-substituted alkoxy group having a carbon atom number of 1-10, an alkenyl group having a carbon atom number of 2-10, a fluoro-substituted alkenyl group having a carbon atom number of 2-10, an alkenoxy group having a carbon atom number of 3-8 or a fluoro-substituted alkenoxy group having a carbon atom number of 3-8, and any one or more non-connected CH.sub.2 in the groups represented by R.sub.1 may be substituted with cyclopentyl, cyclobutyl, cyclopropyl or O; R.sub.2 represents F, OCF.sub.3, OCHF.sub.2 or OCH.sub.2F; m and n each independently represent 1 or 2; and ##STR00079## each independently represent one or two of ##STR00080## and with the proviso that when m+n=2, ##STR00081## represents ##STR00082## and when R.sub.2 represents F, ##STR00083## cannot represent ##STR00084##

11. The liquid crystal composition represented by foimula I-A according to claim 10, wherein said one or more compounds represented by formula I-A are one or more of compounds represented by fo mulas 12 to 14 and 16 to 124 ##STR00085## ##STR00086## ##STR00087## wherein R.sub.11 each independently represents an alkyl having a carbon atom number of 1-6 or an alkenyl group having an atom number of 2-6.

12. A liquid crystal display element or liquid crystal display comprising the liquid crystal compound or liquid crystal composition of claim 1, wherein 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.

13. The liquid crystal composition according to claim 6, wherein said liquid crystal composition further comprises one or more compounds represented by formula VI ##STR00088## wherein R.sub.91 represents an alkyl group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; R.sub.92 represents an alkyl group having a carbon atom number of 1-5, an alkoxy group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; and ##STR00089## represents ##STR00090##

14. The liquid crystal composition according to claim 8, wherein said liquid crystal composition further comprises one or more compounds represented by formula VI ##STR00091## wherein R.sub.91 represents an alkyl group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; R.sub.92 represents an alkyl group having a carbon atom number of 1-5, an alkoxy group having a carbon atom number of 1-5 or an alkenyl group having a carbon atom number of 2-5; and ##STR00092## represents ##STR00093##

15. A liquid crystal display element or liquid crystal display comprising the liquid crystal compound or liquid crystal composition of claim 10, wherein 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

DETAILED DESCRIPTION OF EMBODIMENTS

[0059] The present invention is further described as below in combination with particular embodiments, but the present invention is not limited to the following embodiments. Said methods, if not otherwise indicated, are all conventional methods. Said raw materials, if not otherwise indicated, can all be available through public commercial approaches.

[0060] The reaction process is generally monitored through TLC, and the post-treatments after the reaction is completed are generally water washing, extracting, combining organic phases and then drying, evaporating and removing the solvent under a reduced pressure, recrystallization and column chromatographic separation; and a person skilled in the art would be able to achieve the present invention according to the following description.

[0061] In the present specification, the percentages are mass percentages, the temperatures are in degree Celsius ( C.), and the specific meanings of other symbols and the test conditions are as follows:

[0062] Cp represents the clearing point ( C.) of the liquid crystal measured by a DSC quantitative method;

[0063] S-N represents the melting point ( C.) of the liquid crystal from a crystal state to a nematic phase;

[0064] n represents the optical anisotropy, no is the refractive index of an ordinary light, ne is the refractive index of an extraordinary light, the test conditions are 252 C. and 589 nm, and an Abbe refractometer is used for the test;

[0065] represents the dielectric anisotropy, =//, wherein // is a dielectric constant parallel to a molecular axis, and is a dielectric constant perpendicular to the molecular axis, the test condition is 250.5 C., a 20-micron parallel cell is used, and INSTEC: ALCT-IR1 is used for the test;

[0066] 1 represents a rotary viscosity (mPa.Math.s), the test condition is 250.5 C., a 20-micron parallel cell is used, and INSTEC: ALCT-IR1 is used for the test; and

[0067] represents an electrical resistivity (.Math.cm), the test condition is 252 C., and the test instruments are a TOYO SR6517 high resistance instrument and an LE-21 liquid electrode.

[0068] VHR represents a voltage holding rate (%), and the test condition is 202 , a voltage of 5 V, a pulse width of 10 ms, and a voltage holding time of 16.7 ms. The test equipment is a TOYO Model 6254 liquid crystal performance comprehensive tester.

[0069] represents a response time (ms), the test instrument is DMS-501, the test condition is 250.5 C., the test cell is a 3.3 micron IPS test cell, both the electrode spacing and the electrode width are 10 microns, and the included angle between the frictional direction and the electrode is 10.

[0070] T (%) represents a transmissivity, T (%)=100% *bright state (Vop) luminance/light source luminance, the test equipment is DMS501, the test condition is 250.5 C., the test cell is a 3.3 micron IPS test cell, both the electrode spacing and the electrode width are 10 microns, and the included angle between the frictional direction and the electrode is 10.

[0071] In the examples of the present invention application, liquid crystal monomer structures are represented by codes, wherein the code representation 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 Corresponding code for ring structure Cyclic structure Corresponding code [00035] C [00036] C(V) [00037] B [00038] B(2F,3F,4F) [00039] B(3F) [00040] B(3F,4F,5F) [00041] B(2F) [00042] B(2Me) [00043] B(2F,3F) [00044] C[3O] [00045] C[3O,5O] [00046] Sa [00047] Sc

TABLE-US-00002 TABLE II Corresponding code for end group and linking group 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.3 CF.sub.3 CF.sub.2O CF.sub.2O CH.sub.2O CH.sub.2O F F CN CN CH.sub.2CH.sub.2 E CHCH V CC W COO COO CHCHC.sub.nH.sub.2n+1 Vn [00048] C(5) [00049] C(3) CHCF.sub.2 V(F,F)

EXAMPLES

[0072] ##STR00050##

Example 1

[0073] Synthesis of

##STR00051##

[0074] To a 1000 ml three-necked flask, 0.2 mol of propyl biphenyl boronic acid, 0.21 mol of 2,3,4-trifluorobromobenzene, 300 ml of toluene, 300 ml of ethanol, 200 ml of water, 0.24 mol of sodium carbonate and 1 g of s tetrakis(triphenylphosphine)palladium are added and heated for a reflux reaction for 5 hours, followed by conventional treatments: dissolution with petroleum ether, passing through a silica gel column and recrystallization with anhydrous ethanol to obtain 49.4 g of a white crystal, with a yield of 76% and Gc: 99.91%.

[0075] n [589 nm, 25 C. ]: 0.222

[0076] Cp: 106 C.

[0077] [1 KHz, 25 C]: 4.3

[0078] By means of similar synthesis processing, the following compounds can be obtained:

##STR00052##

[0079] n [589 nm, 25 C]: 0.332

[0080] Cp: 229 C.

[0081] [1 KHz, 25 C]: 6.9

##STR00053##

[0082] n [589 nm, 25 C]: 0.250

[0083] Cp: 241 C.

[0084] [1KHz, 25 C]: 6.8

##STR00054##

[0085] n [589 nm, 25 C]: 0.091

[0086] Cp: 56 C.

[0087] [1KHz, 25 C]: 15

##STR00055##

[0088] n [589 nm, 25 C]: 0.340

[0089] Cp: 110 C.

[0090] [1 KHz, 25 C]: 9.3

##STR00056##

[0091] n [589 nm, 25 C]: 0.242

[0092] Cp: 119 C.

[0093] [1 KHz, 25 C]: 7.3

Example 2

[0094]

TABLE-US-00003 Classification Liquid crystal monomer codes Content (%) I 3CCB(2F,3F,4F) 10 I 3CBB(2F,3F,4F) 13 I 3CBBB(2F,3F,4F) 5 I 3BBB(2F,3F,4F) 14 I 3BBB(2F,3F)OCF3 8 II-B 3CCV 50 n [589 nm, 25 C.]: 0.105 Cp: 78 C. [1 KHz, 25 C.]: 2.3 .sub.1: 56 mPa .Math. s.

Example 3

[0095]

TABLE-US-00004 Classification Liquid crystal monomer codes Content (%) I 3CCB(2F,3F,4F) 5 I 3CBB(2F,3F,4F) 3 I 3BBB(2F,3F,4F) 5 I V2BBB(2F,3F,4F) 4 I 3CBBB(2F,3F,4F) 3 II-B 3CCV 45 II-B 2CC3 5 II 5BB1 10 III 4BBB(2F,4F) 5 III 3BB(3F,5F)CF2O B(2F,3F,4F) 5 III 2BB(3F) B(3F,5F)CF2O B(2F,3F,4F) 2 III 2C[3O]B B(3F,5F)CF2O B(2F,3F,4F) 3 III 4BB(3F) B(3F,5F)CF2O B OCF3 5 n [589 nm, 25 C.]: 0.0988 Cp: 79 C. [1 KHz, 25 C.]: 5.1 .sub.1: 48.5 mPa .Math. s.

Example 4

[0096]

TABLE-US-00005 Classification Liquid crystal monomer codes Content (%) I 3CBB(2F,3F,4F) 7 I 3BBB(2F,3F,4F) 10 I 3CCB(2F,3F,4F) 5 II 3CCV 50 II 4BB2V 9 III H(5)BB(3F,5F)CF2OB(3F,4F,5F) 6 III 2C(3O)BB(3F,5F)CF2OB(3F,4F,5F) 3 III 4BB(3F)B(3F,5F)CF2OB(4F) 10 n [589 nm, 25 C.]: 0.109 Cp: 75 C. [1 KHz, 25 C.]: 5.6 .sub.1: 65 mPa .Math. s.

Comparative Example 1

[0097] By replacing the compound 3CBB(2F,3F,4F) of formula I in Example 4 with common 3CBB(3F,4F,5F), 3BBB(2F,3F,4F) with common 3BBB(3F,4F,5F), and 3CCB(2F,3F,4F) with common 3CCB(3F,4F,5F), a composition of Comparative Example 1 is obtained, .sub.being reduced from 3.8 to 3.1,

[0098] and after the transmissivity thereof is tested, the transmissivity of the composition of Comparative Example 1 is reduced by 8% compared with that of Example 4.

Example 5

[0099]

TABLE-US-00006 Classification Liquid crystal monomer codes Content (%) I 3BBB(2F,3F,4F) 5 II 3CCV 35 II 2CB3 10 III C(5)BB(3F,5F)CF2O B(3F,4F,5F) 7 III C(5)C(3O)BB(3F,5F)CF2OB(3F,4F,5F) 3 III 2BB(3F,5F)CF2OB(3F,4F,5F) 5 IV 4CCB3 10 IV 3CCB(3F)2 5 IV 2CBBC4 5 V 5CCB(4F) 5 V 2CBB(3F,4F) 5 V 4CCBOCF3 5 n [589 nm, 25 C.]: 0.116 Cp: 114 C. [1 KHz, 25 C.]: 5.67 .sub.1: 139 mPa .Math. s.

Example 6

[0100]

TABLE-US-00007 Classification Liquid crystal monomer codes Content (%) I 3CBB(2F,3F,4F) 6 II 3CCV 40 II 4VBO2 10 III 3BB(3F,5F)CF2OB(3F,4F,5F) 4 III 3C(3O,5O)BB(3F,5F)CF2OB(3F,4F,5F) 3 III C(5)BB(3F,5F)CF2O B(3F,4F,5F) 4 IV 2CCB4 7 IV 4CB(3F)B4 6 IV C(3)1BB(3F)B3 5 VI 2CB(2F,3F)O1 5 VI 2BB(2F,3F)O3 5 VI 2CCB(2F,3F)O1 5 n [589 nm, 25 C.]: 0.1168 Cp: 88.2 C. [1 KHz, 25 C.]: 2.51 .sub.1: 142.6 mPa .Math. s.

Example 7

[0101]

TABLE-US-00008 Classification Liquid crystal monomer codes Content (%) I V2BBB(2F,3F,4F) 5 II 3CCV 35 II 2CB3 10 III C(5)BB(3F,5F)CF2OB(3F,4F,5F) 7 III C(5)BB(3F)B(3F,5F)CF2O B(3F,4F,5F) 3 III 2BB(3F,5F)CF2OB(3F,4F,5F) 5 IV 4CCB3 10 IV 3CCB(3F)2 5 IV 2CBBC4 5 V 5CCB(4F) 5 V 2CBB(3F,4F) 5 V 4CCBOCF3 5 n [589 nm, 25 C.]: 0.136 Cp: 115 C. [1 KHz, 25 C.]: 5.25 .sub.1: 105.6 mPa .Math. s.

[0102] The liquid crystal compound of the present invention has a lower viscosity, better stability to light and heat, and is suitable for adjusting a quickly responsive liquid crystal compound having a high transmittance.

[0103] The liquid crystal composition of the present invention has a lower viscosity, better stability to light and heat, a wider refractive index, a wider nematic phase temperature range, and excellent properties in adjusting a quick response and high transmittance, and is particularly suitable for an IPS mode.