SELF ALIGNMENT AGENT AND LIQUID CRYSTAL COMPOSITION THEREOF

Abstract

The present invention provides a self-aligning agent and a liquid crystal composition thereof. The liquid crystal composition comprising the self aligning agent of general formula O in the present invention has a lower residue concentration, a smaller roughness, a better alignment effect as well as a better low-temperature storage stability and a better pre-tilt angle stability while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

##STR00001##

Claims

1. A self-aligning agent of general formula O: ##STR00226## wherein, R.sub.o2 represents -Sp.sub.o2-P.sub.o1, H, C.sub.1-12 linear alkyl, C.sub.3-12 branched alkyl, ##STR00227## wherein one or more than two nonadjacent CH.sub.2in the C.sub.1-12 linear alkyl, ##STR00228## can each be independently replaced by CHCH, CC, O, CO, COO or OCO, and one or more H in the C.sub.1-12 linear alkyl can each be independently substituted by F or Cl; ring ##STR00229## represents ##STR00230## wherein one or more CH.sub.2 in ##STR00231## can be replaced by O, and one or at most two single bonds in the ring can be replaced by double bond; ring ##STR00232## represents ##STR00233## wherein, one or more than two nonadjacent CH.sub.2 in the above groups can each be independently replaced by O or S, and one or more H on the above groups can each be independently substituted by F or C.sub.1-5 halogenated or unhalogenated linear alkyl; L.sub.o1 and L.sub.o3 each independently represents F, Cl, CN, NO.sub.2, NCO, NCS, OCN, SCN, C(O)N(R.sup.o0).sub.2, C(O)R.sup.o0, C.sub.1-12 linear alkyl, C.sub.3-12 branched alkyl, ##STR00234## wherein one or more than two nonadjacent CH.sub.2 in the C.sub.1-12 linear alkyl, ##STR00235## can each be independently replaced by CHCH, CC, O, CO, COO or OCO, and one or more H in the C.sub.1-12 linear alkyl can each be independently substituted by F, wherein R.sup.o0 represents C.sub.1-12 linear alkyl or C.sub.3-12 branched alkyl; L.sub.o2 represents -Sp.sub.o3-P.sub.o2 or ##STR00236## R.sub.o1 and R.sub.o3 each independently represents an anchoring group, the anchoring group is ##STR00237## wherein *_ represents the binding site in the bound structure; n.sub.o4 represents 1 or 2, wherein when n.sub.o4 represents 2, -Sp.sub.o8-X.sub.o2 can be the same or different; n.sub.o5 represents 0 or 1; M.sup.S1 represents ##STR00238## wherein, custom-character represents the binding site between M.sup.S1 and CH.sub.2 in the six-membered ring; I.sup.S1 and J.sup.S1 each independently represents CH.sub.2, O or S; N.sup.S1 represents O or S; V.sup.K1, V.sup.K2 and V.sup.K3 each independently represents CH or N; X.sub.o1 and X.sub.o2 each independently represents H, OH, SH, NH.sub.2, NHR.sup.11, N(R.sup.11).sub.2, NHC(O)R.sup.11, OR.sup.11, C(O)OH, CHO, C.sub.1-12 linear halogenated or unhalogenated alkyl or C.sub.3-12 branched halogenated or unhalogenated alkyl, wherein at least one of X.sub.o1 and X.sub.o2 is selected from a group consisting of OH, SH, NH.sub.2, NHR.sup.11, C(O)OH and CHO, wherein R.sup.11 represents C.sub.1-12 linear alkyl or C.sub.3-12 branched alkyl; P.sub.o1, P.sub.o2 and P.sub.o3 each independently represents polymerizable group; Sp.sub.o1, Sp.sub.o2, Sp.sub.o3, Sp.sub.o4, Sp.sub.o5, Sp.sub.o7 and Sp.sub.o8 each independently represents spacer group or single bond; Sp.sub.o6 represents ##STR00239## wherein, - - - - - represents the binding site to Sp.sub.o7 or Sp.sub.o8; Z.sub.o1 and Z.sub.o2 each independently represents O, S, CO, COO, OCO, OCOO, CH.sub.2O, OCH.sub.2, CH.sub.2S, SCH.sub.2, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, (CH.sub.2).sub.d, CF.sub.2CH.sub.2, CH.sub.2CF.sub.2, (CF.sub.2).sub.d, CHCH, CFCF, CHCF, CFCH, CC, CHCHCOO, OCOCHCH, CH.sub.2CH.sub.2COO, OCOCH.sub.2CH.sub.2, CHR.sup.1, CR.sup.1R.sup.2 or single bond, wherein R.sup.1 and R.sup.2 each independently represents C.sub.1-12 linear alkyl or C.sub.3-12 branched alkyl, and d represents an integer of 1-4; p.sub.o1, p.sub.o2, p.sub.o3 and p.sub.o4 each independently represents 0, 1 or 2, wherein when p.sub.o1 represents 2, L.sub.o1 can be the same or different, wherein when p.sub.o2 represents 2, L.sub.o2 can be the same or different; wherein when p.sub.o3 represents 2, -Sp.sub.o5-R.sub.o3 can be the same or different; wherein when p.sub.o4 represents 2, L.sub.o3 can be the same or different; and n.sub.o2 represents 0, 1, 2 or 3, n.sub.o3 represents 1, 2 or 3, wherein when n.sub.o2 represents 2 or 3, ##STR00240## can be the same or different, wherein when n.sub.o3 represents 2 or 3, ##STR00241## can be the same or different.

2. The self-aligning agent according to claim 1, wherein the self-aligning agent of general formula O is selected from a group consisting of the following compounds: ##STR00242## ##STR00243## ##STR00244## ##STR00245## wherein, L.sub.o4L.sub.o7 each independently represents F or C.sub.1-5 halogenated or unhalogenated linear alkyl.

3. The self-aligning agent according to claim 2, wherein the compound of general formula O-1 is selected from a group consisting of the following compounds: ##STR00246## ##STR00247## wherein, Z.sub.o11 represents O, S, CO, COO, OCO, OCOO, CH.sub.2O, OCH.sub.2, CH.sub.2S, SCH.sub.2, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, (CH.sub.2).sub.d, CF.sub.2CH.sub.2, CH.sub.2CF.sub.2, (CF.sub.2).sub.d, CHCH, CFCF, CHCF, CF=CH, CC, CHCHCOO, OCOCHCH, CH.sub.2CH.sub.2COO, OCOCH.sub.2CH.sub.2, CHR.sup.1, CR.sup.1R.sup.2 or single bond, wherein R.sup.1 and R.sup.2 each independently represents C.sub.1-12 linear alkyl or C.sub.3-12 branched alkyl, and d represents an integer of 1-4; L.sub.o31 represents F, Cl, CN, NO.sub.2, NCO, NCS, OCN, SCN, C(O)N(R.sup.o0).sub.2, C(O)R.sup.o0, C.sub.1-12 linear alkyl, C.sub.3-12 branched alkyl, ##STR00248## wherein one or more than two nonadjacent CH.sub.2 in the C.sub.1-12 linear alkyl, ##STR00249## can each be independently replaced by CHCH, CC, O, CO, COO or OCO, and one or more H in the C.sub.1-12 linear alkyl can each be independently substituted by F, wherein R.sub.o0 represents C.sub.1-12 linear alkyl or C.sub.3-12 branched alkyl; and L.sub.o21 represents -Sp.sub.o3-P.sub.o2 or ##STR00250##

4. The self-aligning agent according to claim 3, wherein the compound of general formula O-1 is selected from a group consisting of the following compounds: ##STR00251## ##STR00252## ##STR00253## wherein, L.sub.o22 represents -Sp.sub.o3-P.sub.o2 or ##STR00254##

5. A liquid crystal composition comprising the self-aligning agent of claim 1.

6. The liquid crystal composition according to claim 5, wherein the liquid crystal composition comprises at least one compound of general formula M: ##STR00255## wherein, R.sub.M1 and R.sub.M2 each independently represents C.sub.1-12 linear alkyl, C.sub.3-12 branched alkyl, ##STR00256## wherein one or more than two nonadjacent CH.sub.2 in the C.sub.1-12 linear alkyl or C.sub.3-12 branched alkyl can each be independently replaced by CHCH, CC, O, CO, COO or OCO; ring ##STR00257## ring ##STR00258## and ring ##STR00259## each independently represents ##STR00260## wherein one or more CH.sub.2 in ##STR00261## can be replaced by O, one or at most two single bonds in the ring can be replaced by double bond, at most one H on ##STR00262## can be substituted by halo; Z.sub.M1 and Z.sub.M2 each independently represents single bond, COO, OCO, CH.sub.2O, OCH.sub.2, CC, CHCH, CH.sub.2CH.sub.2 or (CH.sub.2).sub.4; and n.sub.M represents 0, 1 or 2, wherein when n.sub.M=2, ring ##STR00263## can be the same or different, Z.sub.M2 can be the same or different.

7. The liquid crystal composition according to claim 6, wherein the compound of general formula M is selected from a group consisting of the following compounds: ##STR00264## ##STR00265## ##STR00266##

8. The liquid crystal composition according to claim 5, wherein the liquid crystal composition comprises at least one compound of general formula N: ##STR00267## wherein, R.sub.N1 and R.sub.N2 each independently represents H, C.sub.1-12 linear alkyl, C.sub.3-12 branched alkyl, ##STR00268## wherein one or more than two nonadjacent CH.sub.2 in the C.sub.1-12 linear alkyl or C.sub.3-12 branched alkyl can each be independently replaced by CHCH, CC, O, CO, COO or OCO; ring ##STR00269## and ring ##STR00270## each independently represents ##STR00271## wherein one or more CH.sub.2 in ##STR00272## can be replaced by O, and one or at most two single bonds in the ring can be replaced by double bond, wherein one or more H on ##STR00273## can each be independently substituted by F, Cl or CN, and one or more CH in ring can be replaced by N; Z.sub.N1 and Z.sub.N2 each independently represents single bond, COO, OCO, CH.sub.2O, OCH.sub.2, CHCH, CC, CH.sub.2CH.sub.2, CF.sub.2CF.sub.2, (CH.sub.2).sub.4, CHCH(CH.sub.2)n.sub.N3, CF.sub.2O or OCF.sub.2; L.sub.N1 and L.sub.N2 each independently represents H, halo or C.sub.1-3 alkyl; n.sub.N1 represents 0, 1, 2 or 3, n.sub.N2 represents 0 or 1, and 0n.sub.N1+n.sub.N23, when n.sub.N1=2 or 3, ring ##STR00274## can be the same or different, Z.sub.N1 can be the same or different, and n.sub.N3 represents 0, 1, 2 or 3.

9. The liquid crystal composition according to claim 8, wherein the compound of general formula N is selected from a group consisting of the following compounds: ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## wherein, R.sub.N11 represents C.sub.1-5 linear alkyl, ##STR00287## one or more than two nonadjacent CH.sub.2 in the C.sub.1-5 linear alkyl can each be independently replaced by O, CO, COO or OCO; R.sub.N12 represents H, C.sub.1-5 linear alkyl, ##STR00288## one or more than two nonadjacent CH.sub.2 in the C.sub.1-5 linear alkyl can each be independently replaced by CHCH, CC, O, CO, COO or OCO; and n.sub.N3 represents 0, 1, 2 or 3.

10. The liquid crystal composition according to claim 5, wherein the liquid crystal composition comprises at least one polymerizable compound of general formula RM: ##STR00289## wherein, R.sub.1 represents H, halo, CN, -Sp.sub.2-P.sub.2, C.sub.1-12 linear alkyl, C.sub.3-12 branched alkyl, ##STR00290## wherein one or more than two nonadjacent CH.sub.2 in the C.sub.1-12 linear alkyl, C.sub.3-12 branched alkyl, ##STR00291## can each be independently replaced by CHCH, CC, O, CO, COO or OCO, and one or more H can each be independently substituted by F or Cl; ring ##STR00292## and ring ##STR00293## each independently represents ##STR00294## wherein one or more CH.sub.2 in ##STR00295## can be replaced by O, and one or at most two single bonds in the ring can be replaced by double bond, wherein one or more H on ##STR00296## can each be independently substituted by F, Cl, CN, -Sp.sub.3-P.sub.3, C.sub.1-12 halogenated or unhalogenated linear alkyl, C.sub.1-11 halogenated or unhalogenated linear alkoxy, ##STR00297## and one or more CH in the ring can be replaced by N; ring ##STR00298## represents ##STR00299## wherein one or more H on ##STR00300## can each be independently substituted by F, Cl, CN, -Sp.sub.3-P.sub.3, C.sub.1-12 halogenated or unhalogenated linear alkyl, C.sub.1-11 halogenated or unhalogenated linear alkoxy, ##STR00301## and one or more CH in the rings can be replaced by N; P.sub.1, P.sub.2 and P.sub.3 each independently represents polymerizable group; X.sub.0 represents O, S or CO; Sp.sub.1, Sp.sub.2 and Sp.sub.3 each independently represents spacer group or single bond; Z.sub.1 and Z.sub.2 each independently represents O, S, CO, COO, OCO, OCOO, CH.sub.2O, OCH.sub.2, CH.sub.2S, SCH.sub.2, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, (CH.sub.2).sub.d, CF.sub.2CH.sub.2, CH.sub.2CF.sub.2, (CF.sub.2).sub.d, CHCH, CFCF, CHCF, CF=CH, CC, CHCHCOO, OCOCHCH, CH.sub.2CH.sub.2COO, OCOCH.sub.2CH.sub.2, CHR.sup.1, CR.sup.1R.sup.2 or single bond, wherein R.sup.1 and R.sup.2 each independently represents C.sub.1-12 linear alkyl or C.sub.3-12 branched alkyl, and d represents an integer of 1-4; a represents 0, 1 or 2, b represents 0 or 1, wherein when a represents 2, ring ##STR00302## can be the same or different, Z.sub.1 can be the same or different.

11. The liquid crystal composition according to claim 10, wherein the polymerizable compound of general formula RM is selected from a group consisting of the following compounds: ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## wherein, X.sub.1X.sub.10 and X.sub.12 each independently represents F, Cl, -Sp.sub.3-P.sub.3, C.sub.1-5 linear alkyl or alkoxy, ##STR00308##

12. The liquid crystal composition according to claim 5, wherein the liquid crystal composition comprises at least one compound of general formula B: ##STR00309## wherein, R.sub.B1 and R.sub.B2 each independently represents halo, C.sub.1-12 halogenated or unhalogenated linear alkyl, C.sub.3-12 halogenated or unhalogenated branched alkyl, ##STR00310## wherein one or more than two nonadjacent CH.sub.2 in the C.sub.1-12 halogenated or unhalogenated linear alkyl, C.sub.3-12 halogenated or unhalogenated branched alkyl, ##STR00311## can each be independently replaced by CHCH, CHCF, CC, O, CO, COO or OCO, wherein at most one single bond in ##STR00312## can be replaced by double bond; ring ##STR00313## and ring ##STR00314## each independently represents ##STR00315## wherein one or more CH.sub.2 in ##STR00316## can be replaced by O, and one or at most two single bonds in the rings can be replaced by double bond, wherein one or more H on ##STR00317## can each be independently substituted by CN, F or Cl, and one or more CH in the rings can be replaced by N; X.sub.B represents O, S or CO; L.sub.B1 and L.sub.B2 each independently represents H, F, Cl, CF.sub.3 or OCF.sub.3; Z.sub.B1 and Z.sub.B2 each independently represents COO, OCO, OCH.sub.2, CHCH, CC, CH.sub.2CH.sub.2, CF.sub.2CF.sub.2, (CH.sub.2)n.sub.B3-, (CH.sub.2)n.sub.B3O, (CH.sub.2)n.sub.B3S, CF.sub.2O or OCF.sub.2, wherein n.sub.B3 represents an integer of 0-5; and n.sub.B1 and n.sub.B2 each independently represents 0, 1 or 2, wherein when n.sub.B1 represents 2, ring ##STR00318## can be the same or different, wherein when n.sub.B2 represents 2, ring ##STR00319## can be the same or different.

13. The liquid crystal composition according to claim 12, wherein the compound of general formula B is selected from a group consisting of the following compounds: ##STR00320## ##STR00321## wherein, R.sub.B1 represents C.sub.1-8 linear alkyl or alkoxy, or C.sub.2-8 linear alkenyl or alkenoxy; and X.sub.B1 represents O or CH.sub.2.

14. A liquid crystal display device comprising the liquid crystal composition of claim 5.

Description

DETAILED EMBODIMENTS

[0203] The present invention will be illustrated by combining the detailed embodiments below. It should be noted that, the following examples are exemplary embodiments of the present invention, which are only used to illustrate the present invention, not to limit it. Other combinations and various modifications within the conception of the present invention are possible without departing from the subject matter or scope of the present invention.

[0204] In the present application, unless otherwise specified, the proportions used herein are weight ratios, and temperatures are Celsius temperatures.

[0205] For the convenience of the expression, the group structures of each compound in the following Examples are represented by the codes listed in Table 1:

TABLE-US-00002 TABLE 1 Codes of the group structures of the compounds Unit structure of group Code Name of group [00156] embedded image C 1,4-cyclohexylidene [00157] P 1,4-phenylene [00158] L 1,4-cyclohexenylene [00159] G 2-fluoro-1,4-phenylene [00160] G 3-fluoro-1,4-phenylene [00161] C(5) 1-cyclopentyl [00162] C(5,V) 1-cyclopentene [00163] THF tetrahydrofuran-2-yl [00164] W 2,3-difluoro-1,4-phenylene [00165] B(O) 4,6-difluoro-dibenzo[b,d]furan-3,7-diyl [00166] embedded image B(S) 4,6-difluoro-dibenzo[b,d]thiophene-3,7-diyl [00167] V(2F) difluorovinyl F F fluorine substituent O O oxygen bridge group CHCH or CHCH.sub.2 V vinylidene or vinyl CH.sub.2O 1O methyleneoxy CH.sub.2CH.sub.2 2 ethyl bridge bond C.sub.nH.sub.2n+1 or C.sub.nH.sub.2n n (n alkyl or alkylene represents a positive integer of 1-12)

[0206] Take the compound with the following structural formula as an example:

##STR00168##

[0207] Represented by the codes listed in Table 1, this structural formula can be expressed as nCCGF, in which, n in the code represents the number of carbon atoms of the alkyl on the left, for example, n is 3, meaning that the alkyl is C.sub.3H.sub.7; C in the code represents 1,4-cyclohexylidene, G represents 2-fluoro-1,4-phenylene, and F represents fluoro substituent.

[0208] The abbreviated codes of the test items in the following Examples are as follows: [0209] Cp clearing point (nematic-isotropic phases transition temperature, C.) [0210] n optical anisotropy (589 nm, 20 C.) [0211] dielectric anisotropy (1 KHz, 20 C.) [0212] K.sub.11 splay elastic constant (20 C.) [0213] K.sub.33 bend elastic constant (20 C.) [0214] Ra surface roughness (nm) [0215] .sub.1 rotational viscosity (mPa.Math.s, 20 C.) [0216] t.sub.20 C. low-temperature storage time (day, 20 C.) [0217] PTA pre-tilt angle (, 20 C.) [0218] PTA stability of pre-tilt angle (change in pre-tilt angle after applying voltage for a fixed time, ) [0219] wherein,

[0220] Cp: measured with melting point apparatus.

[0221] n: measured with an Abbe refractometer under sodium lamp (589 nm) light source at 20 C.

[0222] A=.sub.//.sub., in which, .sub.// is the dielectric constant parallel to the molecular axis, .sub. is the dielectric constant perpendicular to the molecular axis, the test conditions: 20 C., 1 KHz, VA type test cell with a cell gap of 6 m.

[0223] .sub.1: measured using a LCM-2 type liquid crystal physical property evaluation system; the test conditions: 20 C., 160 V-260 V, test cell gap 20 m.

[0224] K.sub.11 and K.sub.33: calculated from the CV curve of the liquid crystal measured using LCR meter and a VA test cell, the test conditions: cell gap 6 m, V=0.120 V, 20 C.

[0225] t.sub.20 C.: placing the nematic liquid crystal media in glass vials, storing at 20 C., and recording the time when crystal precipitation is observed, wherein, 7D NG represents crystal precipitation is observed after stored at 20 C. for 7 days, 10D OK represents no crystal precipitation is observed after stored at 20 C. for 10 days.

[0226] Ra: after UV photopolymerization of the polymerizable compound contained in the liquid crystal composition, the liquid crystal molecules are rinsed and then the surface roughness of the polymerized polymer layer is tested with an atomic force microscope (AFM).

[0227] Alignment effect: the liquid crystal containing the self-aligning agent and polymerizable compound is filled into a test cell with ITO on both sides (without PI layer, cell gap 3.2 m). The test cell filled with the liquid crystal is placed in an oven at 120 C. and heated for 1 hour. The test cell is cooled to room temperature at room temperature and then placed in a fixture with upper and lower linear polarizers attached thereto (the light transmission axes of the upper and lower polarizers are orthogonal at) 90. The alignment effect of the liquid crystal on the white backlight panel is observed. If it is all black, it indicates a good alignment effect. If there is light leakage in the corner areas around the test cell, the alignment effect is average. If there is also light leakage in the middle area of the test cell, the alignment effect is poo.

[0228] Residue concentration: after applying UV1 (5.5 mw/cm.sup.2, 313 nm) irradiation for 180 s and UV2 (0.25 mw/cm-2, 313 nm) irradiation for 90 min, the liquid crystal eluted from the liquid crystal test cell is detected by high-performance liquid chromatography (HPLC), and the concentration of polymerizable compound and self-aligning agent therein is called residue concentration (ppm).

[0229] PTA: measured by crystal rotation method. Liquid crystals are filled into VA type test cell (cell gap 3.5 m), and irradiated with ultraviolet light as described in UV1 step with the application of a voltage (15 V, 60 Hz), causing polymerization of the polymerizable compound and generation of pre-tilt angle PTA1, the liquid crystal composition with the generated pre-tilt angle PTA1 are subsequently irradiated with ultraviolet light as described in UV2 step to remove residual polymerizable compounds in the PTA1 state, and at this time the pre-tilt angle formed by the polymerizable compound is PTA2. In the present invention, the polymerization rate of the polymerizable compound is investigated through the comparation of the pre-tilt angles formed after the same exposure time of UV1 irradiation (the smaller the pre-tilt angle, the faster the polymerization rate) or the times for forming the same pre-tilt angle (the shorter the time required for forming the same pre-tilt angle, the fast the polymerization rate).

[0230] PTA: after the test cell used in the measurement of PTA is subjected to UV1 and UV2 steps to form a pre-tilt angle of 880.2, 60 Hz SW wave, AC voltage (20 V) and DC voltage (2 V) are applied to the test cell at 40 C. with the presence of backlight. After a fixed time period, the pre-tilt angle of the test cell is tested, and PTA (165 h)=PTA.sub.(initial)PTA (165 h), the smaller the PTA (165 h), the better the stability of the pre-tilt angle.

[0231] The self-aligning agent of general formula O provided in the present invention may be prepared by conventional organic synthesis methods, wherein the methods for introducing a target terminal group, a cyclic structure and a linking group into a starting material can be found in the following literatures: Organic Synthesis (John Wiley & Sons Inc.), Organic Reactions (John Wiley & Sons Inc.), Comprehensive Organic Synthesis (Pergamon Press), and the like.

[0232] The synthetic methods of the linking groups in the self-aligning agent of general formula O can refer to the following schemes, wherein MSG.sup.1 or MSG.sup.2 is a monovalent organic group having at least one ring, and a plurality of MSG.sup.1 (or MSG.sup.2) used in the following schemes can be the same or different.

(1) Synthesis of Single Bond

##STR00169##

[0233] Compound IA with a single bond is prepared by allowing an aryl boronic acid 1 to react, in the presence of an aqueous carbonate solution and a catalyst such as Tetrakis(triphenylphosphine)palladium (Pd(PPh.sub.3).sub.4), with Compound 2 prepared according to a well-known method. Compound IA with a single bond may also be prepared by allowing Compound 3 prepared according to a well-known method to react with n-butyllithium (n-BuLi) and subsequently with zinc chloride, and further with Compound 2 in the presence of a catalyst such as dichlorobis(triphenylphosphine)palladium (PdCl.sub.2 (PPh.sub.3).sub.2).

(2) Synthesis of COO and OCO

##STR00170##

[0234] A carboxylic acid 4 is obtained by allowing Compound 3 to react with n-butyllithium and then with carbon dioxide. In the presence of 1,3-dicyclohexyl carbodiimide (DCC) and 4-dimethylaminopyridine (DMAP), Compound 4 and Compound 5 synthesized by a well-known method are dehydrated to synthesize Compound IB having COO. A compound having OCO can also be synthesized by this method.

(3) Synthesis of CF.SUB.2.O and OCF.SUB.2.

##STR00171##

[0235] Compound 6 is obtained by treating Compound IB with a thiantoin agent such as Lawesson's reagent. Compound IC having CF.sub.2O is prepared by fluorinating Compound 6 with a hydrogen fluoride-pyridine (HF-Py) and N-bromosuccinimide (NBS). A compound having OCF.sub.2 can also be synthesized by this method.

(4) Synthesis of CHCH

##STR00172##

[0236] Compound 7 is obtained by allowing Compound 3 to react with n-butyllithium and then with formamide such as N,N-dimethylformamide (DMF). Compound ID is prepared by allowing phosphorus ylide, which is generated by reacting a phosphonium salt 8 prepared according to a well-known method with potassium t-butoxide (t-BuOK), to react with Compound 7. A cis isomer is generated by the above method depending on reaction conditions. It should be understood that the cis isomer may be isomerized into a trans isomer according to a well-known method, when necessary.

(5) Synthesis of CH.SUB.2.CH.SUB.2.

##STR00173##

[0237] Compound IE may be prepared by hydrogenating Compound ID with a catalyst such as palladium on carbon (Pd/C).

(6) Synthesis of CH.SUB.2.O or OCH.SUB.2.

##STR00174##

[0238] Compound 9 is obtained by reducing Compound 7 with sodium boron hydride (NaBH.sub.4). Compound 10 is then obtained by halogenating Compound 9 with hydrobromic acid. Alternatively, Compound 11 is obtained by protecting the hydroxyl group of Compound 9 with p-toluenesulfonic acid (TsOH). Then, Compound IF is prepared by allowing Compound 10 or Compound 11 to react with Compound 5 in the presence of potassium carbonate. A compound having OCH.sub.2 may also be synthesized according to these methods.

(7) Synthesis of CHCF.SUB.2

##STR00175##

[0239] Compound IG is prepared by removing hydrofluoric acid from the terminal chain of Compound 11 using a tetrahydrofuran solution of lithium diisopropylamide (LDA).

[0240] For ring structures such as 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, 2,3,5,6-tetrafluoro-1,4-phenylene, the starting materials are already commercially available or their synthesis methods are well-known in the art.

Synthetic Preparation Example 1

[0241] The preparation process of Compound of formula O-1-2-1-1 is as follows:

##STR00176##

Step 1. Synthesis of Compound of Formula 1-c

##STR00177##

[0242] 46.4 g Compound of formula 1-a ((2-pentyl-2,3-dihydro-1H-inden-5-yl) boronic acid), 55.4 g Compound of formula 1-b (4-(4-bromo-2-ethylphenyl) phenol) and 33.2 g potassium carbonate were added into a reaction flask, and fully dissolved in toluene. 1 g Pd(dppf).sub.2Cl.sub.2 was added under N.sub.2 protection, heated to reflux under N.sub.2 protection and reacted for 4 h. Spot detection on the plate shows the disappearance of the raw materials. The reaction was extracted with toluene and chromatographed, and the solvent was removed by dry spinning. The residue was recrystallized 3 times with 800 mL mixed solvent of toluene and ethanol (the volume ratio of toluene to ethanol was 3:1) to afford 56.9 g Compound of formula 1-c (4-[2-ethyl-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]phenol) as white solid, yield 74%.

Step 2. Synthesis of Compound of Formula 1-d

##STR00178##

[0243] 56.9 g Compound of formula 1-c and 3.0 g Diisopropylamine were added into a reaction flask, and fully dissolved in tetrahydrofuran. 49 g N-bromosuccinimide (NBS) was added in batches at a controlled temperature of 05 C. The reaction was naturally warmed and reacted for 6 h. 0.5 L sodium sulfite aqueous solution was added to neutralize the reaction solution until a neutral pH and the solution was separated. The aqueous layer was twice extracted with 300 mL Dichloromethane, and the organic phase was combined, washed twice with 0.5 L water, dried, purified by 30 g silica gel column, eluted with 1 L Dichloromethane, and recrystallized with 0.5 L mixed solvent of n-heptane and ethanol (the volume ratio of n-heptane and ethanol is 10:1) to afford 70.0 g yellow Compound of formula 1-d (2,6-dibromo-4-[2-ethyl-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]phenol), yield: 87%.

Step 3. Synthesis of Compound of Formula 1-e

##STR00179##

[0244] Under N.sub.2 protection, 70.0 g Compound of formula 1-d and 45.0 g Compound 4-[(tert-butyldimethyl)oxy]-3-[(tert-butyldimethyl)oxy]methyl]butan-1-ol were added into a reaction flask, and fully dissolved in Diethyl azodicarboxylate (DEAD). In N.sub.2 atmosphere, 0.3 g Triphenylphosphine was added, and the mixture was reacted at room temperature for 2 h. The reaction was purified, eluted with 2 L n-heptane, and recrystallized with 0.5 L mixed solvent of toluene and n-heptane (the volume ratio of toluene and n-heptane is 1:3) to afford 109.2 g Compound of 1-e (6-(2-{2,6-dibromo-4-[2-ethyl-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]phenoxy}ethyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disiloxane) as white solid, yield: 97%.

[0245] Step 4. Synthesis of Compound of Formula 1-f

##STR00180##

[0246] Under N.sub.2 protection, 13 g Compound (3-hydroxypropyl) boronic acid, 109.2 g Compound of formula 1-e and 34.6 g anhydrous potassium carbonate were added into a reaction flask, and fully dissolved in N, N-dimethylformamide. Under N.sub.2 protection, 0.3 g Tetrakis(triphenylphosphine)palladium was added, and the mixture was reacted at 70 C. for 3 h. The reaction was purified, eluted with 2 L n-hexane, recrystallized with 0.2 L ethanol to afford 82 g Compound of formula 1-f (3-(2-{4-[(tert-butyldimethylsilyl)oxy]-3-{[(tert-butyldimethylsilyl)oxy]methyl}butoxy}-5-[2-ethyl-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-3-(3-hydroxypropyl)phenyl) propan-1-ol) as white solid, yield: 79.3%.

Step 5. Synthesis of Compound of Formula 1-g

##STR00181##

[0247] In a reaction flask, 35 g Dicyclohexyl carbodiimide (DCC) was fully dissolved in 100 mL Dichloromethane and set aside for later use. 82 g Compound of formula 1-f and 8.6 g Compound 2-methylprop-2-enoic acid were added into the reaction flask at room temperature and fully dissolved in Dichloromethane. 1.5 g 4-dimethylaminopyridine (DMAP) was added under stirring. The temperature was controlled at 010 C. and 100 mL solution of Dicyclohexyl carbodiimide in Dichloromethane prepared above was added dropwise into the reaction system and the mixture was reacted overnight. The reaction was purified, eluted with 2 L n-hexane, recrystallized with 0.2 L acetonitrile to afford 89.1g Compound of formula 1-g (Propyl 3-(2-{4-[(tert-butyldimethylsilyl)oxy]-3-{[(tert-butyldimethylsilyl)oxy]methyl}butoxy}-5-[2-ethyl-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-3-{3-[(2-methylprop-2-enoyl)oxy]propyl}phenyl).sub.2-methylprop-2-enoate) as white solid, yield: 93%.

Step 6. Synthesis of Compound of Formula O-1-2-1-1

##STR00182##

[0248] Under N.sub.2 protection, 89.1 g Compound of formula 1-g and 7.3 g ammonium carbonate were added into a reaction flask, and fully dissolved in 0.5 L mixed solvent of acetic acid, water and tetrahydrofuran (the volume ratio of acetic acid, water and tetrahydrofuran is 10:5:2). The mixture was reacted at a controlled temperature of 70-80 C. for 2 h, and extracted with 0.5 L toluene. The reaction was purified, eluted with 2 L toluene, recrystallized with 200 mL ethanol to afford 57.8 g Compound of formula O-1-2-1-1 (Propyl 3-{5-[2-ethyl-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-2-[4-hydroxy-3-(hydroxymethyl)butoxy]-3-{3-[(2-methylprop-2-enoyl)oxy]propyl}phenyl}2-methylprop-2-enoate) as white solid, yield: 85%.

[0249] Mass-to-charge ratio (m/z) of Compound of formula O-1-2-1-1 is 738.1 (M+), Elemental Analysis: C, 76.39; H, 8.46; O, 15.16;

[0250] H-NMR (300 MHz, CDCl.sub.3): 0.85-2.15 (m, 28H), 2.25-3.25 (m, 10H), 3.35-3.73 (m, 6H), 3.95-4.78 (m, 6H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 8H).

[0251] By adjusting the raw materials of Formula 1-b and using the same synthesis method as Synthetic Preparation Example 1, Compounds as shown in the following table can be synthesized accordingly.

TABLE-US-00003 1-b Target Compound [00183] embedded image [00184] Compound of formula O-1-2-1-11 m/z is 728.1 (M+), Elemental Analysis: C, 74.15; H, 7.88; F, 2.61; O, 15.36. H-NMR (300 MHz, CDCl3): 0.85-2.15 (m, 25H), 2.25-3.25 (m, 8H), 3.35-3.73 (m, 6H), 3.95-4.78 (m, 6H), 6.25-6.89 (m, 4H), 6.96-7.95 (m. 8H). [00185] [00186] Compound of formula O-1-2-3-1 m/z is 710.1 (M+), Elemental Analysis: C, 76.02; H, 8.22; O, 15.75; H-NMR (300 MHz, CDCl3): 0.85-2.15 (m, 25H), 2.25-3.25 (m, 8H), 3.35-3.73 (m, 6H), 3.95-4.78 (m, 6H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 9H). [00187] embedded image [00188] Compound of formula O-1-2-1-16 m/z is 724.1 (M+), Elemental Analysis: C, 76.21; H, 8.34; O, 15.45; H-NMR (300 MHz, CDCl3): 0.85-2.15 (m, 25H), 2.25-3.25 (m, 11H), 3.35-3.73 (m, 6H), 3.95-4.78 (m, 6H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 8H). [00189] [00190] Compound of formula O-1-2-1-21 m/z is 740.1 (M+), Elemental Analysis: C, 74.56; H, 8.16; O, 17.27. H-NMR (300 MHz, CDCl3): 0.85-2.15 (m, 25H), 2.25-3.25 (m, 8H), 3.35-3.73 (m, 6H), 3.83 (s, 3H), 3.95-4.78 (m, 6H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 8H), [00191] embedded image [00192] Compound of formula O-1-2-1-6 m/z is 754.1 (M+), Elemental Analysis: C, 74.77; H, 8.28; O, 16.95; H-NMR (300 MHz, CDCl3): 0.85-2.15 (m, 28H), 2.25-3.25 (m, 8H), 3.35-3.73 (m, 6H), 3.95-4.80 (m, 8H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 8H). [00193] text missing or illegible when filed

Synthetic Preparation Example 2

[0252] The preparation process of Compound of formula O-1-2-1-15 is as follows:

##STR00194##

Step 1. Synthesis of Compound of Formula 2-c

##STR00195##

[0253] 23.3 g Compound of formula 2-a, 29.7 g Compound of formula 2-b and 25.4 g anhydrous sodium carbonate were added into a reaction flask, and fully dissolved in toluene. In N.sub.2 atmosphere, 0.1 g Pd-132 was added, and the mixture was reacted for 4 h. The mixture was adjusted to acidity with 1 M dilute hydrochloric acid, followed by liquid separation. The organic phase was washed with water, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using 2 L mixed solvent of n-heptane and toluene (the volume ratio of n-heptane and toluene was 1:1) and recrystallized to afford 36.4 g Compound of formula 2-c (4-[2-fluoro-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-2-methoxyphenol) as white crystal, yield 90%.

Step 2. Synthesis of Compound of Formula 2-d

##STR00196##

[0254] 36.4 g white crystal of Compound of formula 2-c was added into a reaction flask, and fully dissolved in carbon tetrachloride. In N.sub.2 atmosphere, 0.2 g Fe powder was added, followed by dropwise addition of 16 g liquid bromine over 1 h. After 30 min, the excess bromine was removed by washing with sodium bisulfite solution. The organic phase was washed with water, and the solvent was evaporated under reduced pressure. The crude product was recrystallized with 180 mL mixed solvent of n-heptane and ethanol (the volume ratio of n-heptane and ethanol is 5:1) to afford 35.8 g Compound of formula 2-d (2-bromo-4-[2-fluoro-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-6-methoxyphenol) white crystal, yield 82%.

Step 3. Synthesis of Compound of Formula 2-e

##STR00197##

[0255] 35.8 g white crystal of Compound of formula 2-d and 10.6 g sodium carbonate were added into a reaction flask, and fully dissolved in tetrahydrofuran. In N.sub.2 atmosphere, 15.3 g 4-bromobutanol was added, and the mixture was reacted at 80 C. for 6 h. The reaction mixture was poured into 500 mL water and extracted with 700 mL toluene. The organic phase was washed with 300 mL water, and the solvent was evaporated under reduced pressure. The crude product was recrystallized with 300 mL mixed solvent of n-heptane and ethanol (the volume ratio of n-heptane and ethanol was 4:1) to afford 35.6 g Compound of formula 2-e (4-{2-bromo-4-[2-fluoro-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-6-methoxyphenoxy}butan-1-ol), yield 86%.

Step 4. Synthesis of Compound of Formula 2-f

##STR00198##

[0256] 20.3 g 5-bromo-2-methoxyphenol and 13.8 g sodium carbonate were added into a reaction flask, and fully dissolved in tetrahydrofuran. In N.sub.2 atmosphere, 20.7 g 3-bromopropanol was added at a controlled temperature of 80 C., and the mixture was reacted for 6 h and extracted with 200 mL toluene. The organic phase was washed with water, and the solvent was evaporated under reduced pressure. The crude product was recrystallized with 50 mL n-heptane to afford 19.8 g Compound of formula 2-f (3-(5-bromo-2-methoxyphenoxy) propan-1-ol), yield 76%.

Step 5. Synthesis of Compound of Formula 2-g

##STR00199##

[0257] 19.8 g Compound of formula 2-f, 25.3 g bis(pinacolato)diboron and 8.2 g anhydrous sodium carbonate were added into a reaction flask, and fully dissolved in toluene. In N.sub.2 atmosphere, 0.4 g Tetrakis(triphenylphosphine)palladium was added, and the mixture was refluxed for 4 hours. The reaction mixture was washed with water and evaporated under reduced pressure. The crude product was recrystallized with 100 mL n-heptane to afford 19.5 g Compound of formula 2-g (3-[2-methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy]propan-1-ol) as pale-yellow crystal, yield 83%.

Step 6. Synthesis of Compound of Formula 2-h

##STR00200##

[0258] 19.5 g pale-yellow crystal of Compound of formula 2-g, 35.6 g Compound of formula 2-e and 10.6 g anhydrous sodium carbonate were added into a reaction flask, and fully dissolved in toluene. In N.sub.2 atmosphere, 0.5 g Tetrakis(triphenylphosphine)palladium was added, and the mixture was refluxed for 4 h. The reaction mixture was washed with water and evaporated under reduced pressure. The crude product was recrystallized with 600 mL mixed solvent of toluene and n-heptane (the volume ratio of toluene and n-heptane was 1:2) to afford 30.9 g Compound of formula 2-h (4-{4-[2-fluoro-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-2-[3-(3-hydroxypropoxy)-4-methoxyphenyl]-6-methoxyphenoxy}butan-1-ol) as white crystal, yield 75%.

Step 7. Synthesis of Compound of Formula 2-i

##STR00201##

[0259] 30.9 g white crystal of Compound of formula 2-h was added into a reaction flask, and fully dissolved in Dichloromethane. At 30 C., 35.8 g boron tribromide was added dropwise, and the mixture was maintained at this temperature and reacted for 3 h. The reaction mixture was washed with water, the organic phase was separated, and the solvent was evaporated under reduced pressure. The crude product was recrystallized with 100 mL mixed solvent of n-heptane and ethanol (the volume ratio of n-heptane and ethanol was 3:1) to afford 23.9 g Compound of formula 2-i (5-[2-fluoro-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-3-[4-hydroxy-3-(3-hydroxypropoxy)phenyl]-2-(4-hydroxybutoxy) phenol) as white solid, yield 81%.

Step 8. Synthesis of Compound of Formula 2-i

##STR00202##

[0260] 23.9 g white solid of Compound of formula 2-i and 2.8 g imidazole were added into a reaction flask, and fully dissolved in tetrahydrofuran. The solution was cooled to 0 C. under nitrogen protection, and 5.9 g tert-butyldimethylsilyl chloride was added within 40 min, and the mixture was maintained at 0 C. and reacted for 1.5 h. The reaction mixture was washed with 500 mL ammonium chloride solution, extracted with 500 mL methyl tert-butyl ether. The organic phase was separated, washed with water until neutral, dried, and rotary evaporated. The crude product was recrystallized with 100 mL mixed solvent of n-heptane and ethanol (the volume ratio of n-heptane and ethanol was 3:1) to afford 20.6 g Compound of formula 2-j (2-{4-[(tert-butyldimethylsilyl)oxy]butoxy}-3-(3-{3-[(tert-butyldimethylsilyl)oxy]propoxy}-4-hydroxyphenyl)-5-[2-fluoro-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]phenol) as white solid, yield 63%.

Step 9. Synthesis of Compound of Formula 2-k

##STR00203##

[0261] 20.6 g white solid of Compound of formula 2-j and 13.8 g potassium carbonate were added into a reaction flask, and fully dissolved in tetrahydrofuran. In N.sub.2 atmosphere, 19.3 g 2-bromoethyl methacrylate was added, and the mixture was reacted for 6 h at a controlled temperature of 70 C. 300 mL water was added and the mixture was extracted with 300 mL toluene. The organic phase was washed with water, dried and recrystallized with 50 mL mixed solvent of toluene and ethanol (the volume ratio of toluene and ethanol was 1:3), to afford 13 g Compound of formula 2-k (2-[4-(2-{4-[(tert-butyldimethylsilyl)oxy]butoxy}-5-[2-fluoro-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-3-{2-[(2-methylprop-2-enoyl)oxy]ethoxy}phenyl)-2-{3-[(tert-butyldimethylsilyl)oxy]propoxy}phenoxy]ethyl 2-methylprop-2-enoate), yield 50%.

Step 10. Synthesis of Compound of Formula O-1-2-1-15

##STR00204##

[0262] 13 g Compound of formula 2-k was added into a reaction flask, and fully dissolved in tetrahydrofuran. The solution was cooled to 0 C., 7.5 mL 2 M dilute hydrochloric acid was slowly added dropwise, and the mixture was reacted at room temperature under stirring for 3 h. The temperature was controlled at 0 C., and 200 mL saturated sodium bicarbonate aqueous solution was added, and the mixture was extracted with 300 mL methyl tert-butyl ether. The organic phase was separated, washed with water until neutral, dried, and rotary evaporated. The crude product was recrystallized with 50 mL mixed solvent of n-heptane and ethanol (the volume ratio of n-heptane and ethanol was 4:1) to afford 7.2 g Compound of formula O-1-2-1-15 (ethyl 2-(4-{5-[2-fluoro-4-(2-pentyl-2,3-dihydro-1H-inden-5-yl)phenyl]-2-(4-hydroxybutoxy)-3-{2-[2-methylprop-2-enoyl)oxy]ethoxy}phenyl}-2-(3-hydroxypropoxy) phenoxy).sub.2-methylprop-2-enoate) as white solid, yield 70%.

[0263] m/z of Compound of formula O-1-2-1-15 is 852.1 (M+), Elemental Analysis: C, 71.81; H, 7.21; F, 2.23; O, 18.76;

[0264] H-NMR (300 MHz, CDCl.sub.3): 0.85-2.15 (m, 24H), 2.25-3.25 (m, 4H), 3.35-3.73 (m, 6H), 3.95-4.78 (m, 12H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 11H).

[0265] By adjusting the raw materials of Formula 2-b and using the same synthesis method as Synthetic Preparation Example 2, Compounds as shown in the following table can be synthesized accordingly.

TABLE-US-00004 2-b Target Compound [00205] embedded image [00206] Compound of formula O-1-3-5 m/z is 834.1 (M+), Elemental Analysis: C, 73.36; H, 7.48; F, 2.23; O, 19.16; H-NMR (300 MHz, CDCl3): 0.85-2.15 (m, 24H), 2.25-3.25 (m, 4H), 3.35-3.73 (m, 6H), 3.95-4.78 (m, 12H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 12H). [00207] [00208] Compound of formula O-1-2-1-20 m/z is 848.1 (M+), Elemental Analysis: C, 73.56; H, 7.60; O, 18.84; H-NMR (300 MHz, CDCl3): 0.85-2.15 (m, 24H), 2.25-3.25 (m, 7H), 3.35-3.73 (m, 6H), 3.95-4.78 (m, 12H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 11H). [00209] embedded image [00210] Compound of formula O-1-2-1-5 m/z is 862.1 (M+), Elemental Analysis: C, 73.75; H, 7.71; O, 18.54; H-NMR (300 MHz, CDCl3): 0.85-2.15 (m, 27H), 2.25-3.25 (m, 6H), 3.35-3.73 (m, 6H), 3.95-4.78 (m, 12H), 6.25-6.89 (m, 4H), 6.96-7.95 (m, 11H).

[0266] The components used in the following Examples can either be synthesized by method known in the art or be obtained commercially. These synthetic techniques are conventional, and each of the obtained liquid crystal compounds is tested to meet the standards of electronic compounds.

[0267] The liquid crystal compositions are prepared in accordance with the ratios specified in the following Examples. The preparation of the liquid crystal compositions is proceeded by mixing in accordance with the ratios through conventional methods in the art, such as heating, ultrasonic wave, suspension and the like.

[0268] The structures of the polymerizable compounds used in each of the following Examples are shown in Table 2 below.

TABLE-US-00005 TABLE 2 Polymerizable compounds used in Examples Structural formula General formula code [00211] embedded image RM-1-1 [00212] RM-2-1 [00213] RM-20-1

[0269] The structures of self-aligning agents used in each of the following Examples are shown in Table 3 below.

TABLE-US-00006 TABLE 3 Self-aligning agents used in Examples Component General number Structural formula formula code D-1 [00214] embedded image D-2 [00215] D-2 [00216] D-3 [00217] D-3 [00218] D-4 [00219] AD-1 [00220] O-1-2-1-1 AD-2 [00221] O-1-2-3-1 AD-3 [00222] O-1-2-1-15 AD-3 [00223] O-1-2-1-11 AD-4 [00224] O-1-2-3-4 AD-5 [00225] O-1-6-2

[0270] Host liquid crystal compositions Host-1. Host-2, Host-3. Host-4. Host-5 and Host-6 are prepared according to each compound and weight percentage listed in Table 4 and are tested by filling the same between two substrates of a liquid crystal display device.

TABLE-US-00007 TABLE 4 Formulations and test results for performance parameters of host liquid crystal compositions Component General Weight percentage code formula code Host-1 Host-2 Host-3 Host-4 Host-5 Host-6 3CPWO4 N-21 9 8 3C1OWO2 N-7 7.5 2CPWO2 N-21 5 5 3CPWO2 N-21 2.5 7.5 2.5 3CPWO3 N-21 9 1VCPWO2 N-53 9 9 2OPWO2 N-19 6 6 3PWO2 N-19 9 15 10.5 9 10.5 2CC1OWO2 N-15 7 3CC1OWO2 N-15 7 4CC1OWO2 N-15 8 4C1OWO2 N-7 5 3CWO2 N-2 13 13 6 13 3CWO4 N-2 2 2 5CWO2 N-2 5 2CCWO2 N-9 6.5 5 4 4 3CCWO2 N-9 13.5 12 13 13.5 13 3LWO2 N-3 6 2CLWO2 N-12 6.5 3CPO2 M2-5 6 3CC2 M-1-2 15 14 17 14 5CC2 M-1-9 9 4 4 3CC4 M-1-4 9 6 6 3CCV M-1-5 28.5 28.5 3CCV1 M-1-6 10.5 9.5 8 10.5 8 3CCP1 M-11-1 2 3CCP2 M-11-2 13 9 8 4 3CPP1 M-13-1 7 3CPP2V1 M-13-9 5 3CPP2V M-13-8 4 5PP1 M-4 6.5 8 4 3PPO2 M-4 4 Total 100 100 100 100 100 100 Cp 76.4 74.9 75.7 76.2 76.8 77 n 0.089 0.1 0.109 0.109 0.102 0.11 3.4 3.1 3.3 3 3.1 2.6 K.sub.11 14.5 11.7 14.6 14.2 12.1 14.5 K.sub.33 13.8 14.9 15.6 15.7 15.3 16.1 .sub.1 105 101 106 84 103 78

Comparative Examples 1-3 and Examples 1-3

[0271] 0.3 parts by weight of polymerizable compound RM-1-1 and 0.7 parts by weight of D-1, D-2 and D-3 respectively are added into 100 parts by weight of host liquid crystal composition Host-1 to prepare the liquid crystal compositions of Comparative Examples 1-3 respectively, and 0.3 parts by weight of polymerizable compound RM-1-1 and 0.7 parts by weight of AD-1, AD-2 and AD-3 are added into 100 parts by weight of host liquid crystal composition Host-1 to prepare the liquid crystal compositions of Examples 1-3 respectively. The physical property values of each of the obtained liquid crystal compositions showed negligible changes relative to perspective host liquid crystal composition. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 1-3 and Examples 1-3 are shown in Table 5 below.

TABLE-US-00008 TABLE 5 Test results for performances of the liquid crystal compositions of Comparative Examples 1-3 and Examples1-3 Comp. Comp. Comp. Ex. 1 Ex. 2 Ex. 3 Ex. 1 Ex. 2 Ex. 3 Residue conc. 155 183 168 105 118 109 Ra 15.1 16.4 15.8 12.3 11.8 12.5 Alignment effect Fair Fair Poor Good Good Good

[0272] It can be seen from the comparison between Example 1 and Comparative Example 1, the comparison between Example 2 and Comparative Example 2 and the comparison between Example 3 and Comparative Example 3 that, the liquid crystal composition comprising the self-aligning agent of general formula O in the present invention has a lower residue concentration (105-118 ppm VS 155-183 ppm), a smaller roughness (11.8-12.5 nm VS 15.1-16.4 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 4-6 and Examples 4-6

[0273] 0.3 parts by weight of polymerizable compound RM-1-1 and 1 parts by weight of D-1, D-2 and D-3 respectively are added into 100 parts by weight of host liquid crystal composition Host-2 to prepare the liquid crystal compositions of Comparative Examples 4-6 respectively, and 0.3 parts by weight of polymerizable compound RM-1-1 and 1 parts by weight of AD-1, AD-2 and AD-3 are added into 100 parts by weight of host liquid crystal composition Host-2 to prepare the liquid crystal compositions of Examples 4-6 respectively. The physical property values of each of the obtained liquid crystal compositions showed negligible changes relative to perspective host liquid crystal composition. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 4-6 and Examples 4-6 are shown in Table 6 below.

TABLE-US-00009 TABLE 6 Test results for performances of the liquid crystal compositions of Comparative Examples 4-6 and Examples 4-6 Comp. Comp. Comp. Ex. 4 Ex. 5 Ex. 6 Ex. 4 Ex. 5 Ex. 6 Residue 168 197 179 113 126 119 conc. Ra 15.3 15.9 15.5 11.6 11.9 12.3 Alignment Fair Fair Poor Good Good Good effect

[0274] It can be seen from the comparison between Example 4 and Comparative Example 4, the comparison between Example 5 and Comparative Example 5 and the comparison between Example 6 and Comparative Example 6 that, the liquid crystal composition comprising the self-aligning agent of general formula O in the present invention has a lower residue concentration (113-126 ppm VS 168-197 ppm), a smaller roughness (11.6-12.3 nm VS 15.3-15.9 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 7-9 and Example 7-9

[0275] 0.3 parts by weight of polymerizable compound RM-2-1 and 0.9 parts by weight of D-1, D-2 and D-3 respectively are added into 100 parts by weight of host liquid crystal composition Host-3 to prepare the liquid crystal compositions of Comparative Examples 7-9 respectively, and 0.3 parts by weight of polymerizable compound RM-2-1 and 0.9 parts by weight of AD-I, AD-2 and AD-3 are added into 100 parts by weight of host liquid crystal composition Host-3 to prepare the liquid crystal compositions of Examples 7-9 respectively. The physical property values of each of the obtained liquid crystal compositions showed negligible changes relative to perspective host liquid crystal composition. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 7-9 and Examples 7-9 are shown in Table 7 below.

TABLE-US-00010 TABLE 7 Test results for performances of the liquid crystal compositions of Comparative Examples 7-9 and Examples 7-9 Comp. Comp. Comp. Ex. 7 Ex. 8 Ex. 9 Ex. 7 Ex. 8 Ex. 9 Residue 163 189 172 110 123 117 conc. Ra 15.5 16.1 15.4 11.8 12 12.4 Alignment Fair Fair Poor Good Good Good effect

[0276] It can be seen from the comparison between Example 7 and Comparative Example 7, the comparison between Example 8 and Comparative Example 8 and the comparison between Example 9 and Comparative Example 9 that, the liquid crystal composition comprising the self-aligning agent of general formula O in the present invention has a lower residue concentration (110-123 ppm VS 163-189 ppm), a smaller roughness (11.8-12.4 nm VS 15.4-16.1 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 10-12 and Examples 10-12

[0277] 0.3 parts by weight of polymerizable compound RM-1-1 and 0.8 parts by weight of D-1, D-2 and D-3 respectively are added into 100 parts by weight of host liquid crystal composition Host-4 to prepare the liquid crystal compositions of Comparative Examples 10-12 respectively, and 0.3 parts by weight of polymerizable compound RM-1-1 and 0.8 parts by weight of AD-1, AD-2 and AD-3 are added into 100 parts by weight of host liquid crystal composition Host-4 to prepare the liquid crystal compositions of Examples 10-12 respectively. The physical property values of each of the obtained liquid crystal compositions showed negligible changes relative to perspective host liquid crystal composition. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 10-12 and Examples 10-12 are shown in Table 8 below.

TABLE-US-00011 TABLE 8 Test results for performances of the liquid crystal compositions of Comparative Examples 10-12 and Examples 10-12 Comp. Comp. Comp. Ex. 10 Ex. 11 Ex. 12 Ex. 10 Ex. 11 Ex. 12 Residue 189 223 207 126 144 132 conc. Ra 14.8 15.6 15.1 11.5 11.7 12 Alignment Fair Fair Poor Good Good Good effect

[0278] It can be seen from the comparison between Example 10 and Comparative Example 10, the comparison between Example 11 and Comparative Example 11 and the comparison between Example 12 and Comparative Example 12 that, the liquid crystal composition comprising the self-aligning agent of general formula O in the present invention has a lower residue concentration (126-144 ppm VS 189-223 ppm), a smaller roughness (11.5-12 nm VS 14.8-15.6 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Examples 13-17

[0279] The liquid crystal compositions of Examples 13-17 are prepared according to the parts by weight of each compound listed in Table 9. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Examples 13-17 are shown in Table 10 below.

TABLE-US-00012 TABLE 9 Formulations of the liquid crystal compositions of Examples 13-17 Ex. 13 Ex. 14 Ex. 15 Ex. 16 Ex. 17 Host-5 100 100 Host-6 100 100 100 RM-1-1 0.3 0.3 0.3 RM-2-1 0.28 0.3 RM-20-1 0.02 AD-1 0.8 0.5 AD-2 0.8 0.8 0.5 AD-3 0.3 0.3

TABLE-US-00013 TABLE 10 Test results for performances of the liquid crystal compositions of Examples 13-17 Ex. 13 Ex. 14 Ex. 15 Ex. 16 Ex. 17 Residue 108 105 141 138 133 conc. Ra 11.8 11.4 11.5 11.7 11.6 Alignment Good Good Good Good Good effect

[0280] It can be seen from the performance parameters of Examples 13-17 that, the liquid crystal composition comprising the self-aligning agent of general formula O in the present invention has a lower residue concentration (105-141 ppm), a smaller roughness (11.4-11.8 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

[0281] Host liquid crystal compositions Host-7, Host-8, Host-9, Host-10 and Host-11 are prepared according to each compound and weight percentage listed in Table 11, and are tested by filling the same between two substrates of a liquid crystal display device.

TABLE-US-00014 TABLE 11 Formulations and test results for performance parameters of host liquid crystal compositions General formula Weight percentage Component code code Host-7 Host-8 Host-9 Host-10 Host-11 2CPWO2 N-21 7.5 3.5 11 7.5 3CPWO2 N-21 9 10.3 9 3CCWO2 N-9 3 3 3CLWO2 N-12 4 7 4 6.3 4 2OPWO2 N-19 6 5.5 6 6 3CC2 M-1-2 3.2 3CCV M-1-5 37 29 25.5 29 37 1PP2V1 M-4 5 4 5 VCCP1 M-11-1 5 5 3CCP1 M-11-1 11 12.5 11.5 3CCP3 M-11-3 3.5 3CPP2 M-13-2 1.2 6.5 1PWO2 N-19 9 11 11 10.5 9 2PWO2 N-19 10 3PWO2 N-19 9 4OB(S)O2 B-1-1 4 5OB(S)O2 B-1-1 2.5 C(5)1OB(S)O4 B-4 2.5 2.5 C(5)1OB(S)O2 B-4 2.5 2.5 C(5, V)1OB(S)O4 B-7 8 C(5, V)1OB(S)O2 B-7 4 4OB(S)OV(2F) B-1-4 4 3CCV1 M-1-6 5 8.5 9.5 8.5 5 3CPWO4 N-21 4.5 4.5 1VCPWO2 N-53 9 Total 100 100 100 100 100 Cp 75.3 75 75.2 75.3 75.2 n 0.1145 0.1145 0.1146 0.1145 0.115 2.88 2.83 3.2 2.97 2.83 K.sub.11 15.1 14.7 14.1 15.6 14.8 K.sub.33 16.4 15.7 16.3 16.8 16.0 .sub.1 68 69 70 75 70

[0282] Host liquid crystal compositions Host-12, Host-13, Host-14 and Host-15 are prepared according to each compound and weight percentage listed in Table 12, and are tested by filling the same between two substrates of a liquid crystal display device.

TABLE-US-00015 TABLE 12 Formulations and test results for performance parameters of host liquid crystal compositions General formula Weight percentage Component code code Host-12 Host-13 Host-14 Host-15 2CPWO2 N-21 3.5 11 11 5 3CPWO2 N-21 10.3 3CLWO2 N-12 7 4 4 5 2OPWO2 N-19 5.5 3PWO2 N-19 9 9 2PWO2 N-19 10 10 1PWO2 N-19 11 11 11 3PPWO2 N-23 2 3CPP2 M-13-2 1.2 6.5 6.5 6 1VCPP2 M-13-2 3 3CCP1 M-11-1 11 12.5 12.5 3CCP3 M-11-3 3.5 3.5 3CC2 M-1-2 3CCV M-1-5 29 25.5 25.5 36.5 3CCV1 M-1-6 8.5 9.5 9.5 6.5 1PP2V1 M-4 8 4OB(S)O2 B-1-1 4 4OB(O)O2 B-1-1 4 5OB(O)O2 B-1-1 2.5 2.5 C(5,V)1OB(S)O4 B-7 5 C(5,V)1OB(S)O2 B-7 4 C(5,V)1OB(O)O4 B-7 C(5,V)1OB(O)O2 B-7 4OB(O)OV(2F) B-1-4 4 3 1VCPWO2 N-53 7 Total 100 100 100 100 Cp 74.9 75.1 75.1 73.7 n 0.1147 0.1148 0.1151 0.121 2.79 3.13 3.13 2.3 K.sub.11 14.5 14 13.9 14.7 K.sub.33 15.4 16.2 16.1 15.2 .sub.1 71 71 72 67

Comparative Examples 13-15 and Examples 18-22

[0283] The liquid crystal compositions of Comparative Examples 13-15 and Examples 18-22 are prepared according to the parts by weight of each compound listed in Table 13. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer).

[0284] The test results for relevant performances of the liquid crystal compositions of Comparative Examples 13-15 and Examples 18-22 are shown in Table 14 below.

TABLE-US-00016 TABLE 13 Formulations of the liquid crystal compositions of Comparative Examples 13-15 and Examples 18-22 Comp. Comp. Comp. Ex. 13 Ex. 14 Ex. 15 Ex. 18 Ex. 19 Ex. 20 Ex. 21 Ex. 22 Host-7 100 100 100 100 100 100 100 100 RM-1-1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 D-1 0.7 D-2 0.7 D-3 0.7 AD-2 0.7 AD-1 0.7 AD-3 0.7 AD-4 0.7 AD-5 0.7

TABLE-US-00017 TABLE 14 Test results for performances of the liquid crystal compositions of Comparative Examples 13-15 and Examples 18-22 Comp. Comp. Comp. Ex. 13 Ex. 14 Ex. 15 Ex. 18 Ex. 19 Ex. 20 Ex. 21 Ex. 22 Residue 235 203 252 185 202 156 179 158 conc. Ra 13.8 14.7 14.4 10.9 11.1 11.4 11.5 11.9 Alignment Fair Fair Poor Good Good Good Good Good effect

[0285] It can be seen from the comparison between Examples 18-22 and Comparative Examples 13-15 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (156-202 ppm VS 203-252 ppm), a smaller roughness (10.9-11.9 nm VS 13.8-14.7 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 16-18 and Examples 23-27

[0286] The liquid crystal compositions of Comparative Examples 16-18 and Examples 23-27 are prepared according to the parts by weight of each compound listed in Table 15. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 16-18 and Examples 23-27 are shown in Table 16 below.

TABLE-US-00018 TABLE 15 Formulations of the liquid crystal compositions of Comparative Examples 16-18 and Examples 23-27 Comp. Comp. Comp. Ex. 16 Ex. 17 Ex. 18 Ex. 23 Ex. 24 Ex. 25 Ex. 26 Ex. 27 Host-8 100 100 100 100 100 100 100 100 RM-1-1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 D-1 0.8 D-2 0.8 D-3 0.8 AD-2 0.8 AD-1 0.8 AD-3 0.8 AD-4 0.8 AD-5 0.8

TABLE-US-00019 TABLE 16 Test results for performances of the liquid crystal compositions of Comparative Examples 16-18 and Examples 23-27 Comp. Comp. Comp. Ex. 16 Ex. 17 Ex. 18 Ex. 23 Ex. 24 Ex. 25 Ex. 26 Ex. 27 Residue 213 185 238 162 183 143 158 146 conc. Ra 13.9 14.8 14.5 10.7 10.8 11.1 11.3 11.6 Alignment Fair Fair Poor Good Good Good Good Good effect

[0287] It can be seen from the comparison between Examples 23-27 and Comparative Examples 16-18 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (143-183 ppm VS 185-238 ppm), a smaller roughness (10.7-11.6 nm VS 13.9-14.8 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 19-21 and Examples 28-32

[0288] The liquid crystal compositions of Comparative Examples 19-21 and Examples 28-32 are prepared according to the parts by weight of each compound listed in Table 17. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 19-21 and Examples 28-32 are shown in Table 18 below.

TABLE-US-00020 TABLE 17 Formulations of the liquid crystal compositions of Comparative Examples 19-21 and Examples 28-32 Comp. Comp. Comp. Ex. 19 Ex. 20 Ex. 21 Ex. 28 Ex. 29 Ex. 30 Ex. 31 Ex. 32 Host-9 100 100 100 100 100 100 100 100 RM-2-1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 D-1 1 D-2 1 D-3 1 AD-2 1 AD-1 1 AD-3 1 AD-4 1 AD-5 1

TABLE-US-00021 TABLE 18 Test results for performances of the liquid crystal compositions of Comparative Examples 19-21 and Examples 28-32 Comp. Comp. Comp. Ex. 19 Ex. 20 Ex. 21 Ex. 28 Ex. 29 Ex. 30 Ex. 31 Ex. 32 Residue 198 175 217 161 172 135 155 142 conc. Ra 14.0 14.9 14.5 10.7 10.9 11.2 11.3 11.7 Alignment Fair Fair Poor Good Good Good Good Good effect

[0289] It can be seen from the comparison between Examples 28-32 and Comparative Examples 19-21 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (135-172 ppm VS 175-219 ppm), a smaller roughness (10.7-11.7 nm VS 14.0-14.9 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 22-24 and Examples 33-37

[0290] The liquid crystal compositions of Comparative Examples 22-24 and Examples 33-37 are prepared according to the parts by weight of each compound listed in Table 19. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 22-24 and Examples 33-37 are shown in Table 20 below.

TABLE-US-00022 TABLE 19 Formulations of the liquid crystal compositions of Comparative Examples 22-24 and Examples 33-37 Comp. Comp. Comp. Ex. 22 Ex. 23 Ex. 24 Ex. 33 Ex. 34 Ex. 35 Ex. 36 Ex. 37 Host-10 100 100 100 100 100 100 100 100 RM-1-1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 D-1 0.9 D-2 0.9 D-3 0.9 AD-2 0.9 AD-1 0.9 AD-3 0.9 AD-4 0.9 AD-5 0.9

TABLE-US-00023 TABLE 20 Test results for performances of the liquid crystal compositions of Comparative Examples 22-24 and Examples 33-37 Comp. Comp. Comp. Ex. 22 Ex. 23 Ex. 24 Ex. 33 Ex. 34 Ex. 35 Ex. 36 Ex. 37 Residue 192 174 209 155 166 128 149 135 conc. Ra 14.2 15.1 14.6 10.6 10.7 11.0 11.2 11.5 Alignment Fair Fair Poor Good Good Good Good Good effect

[0291] It can be seen from the comparison between Examples 33-37 and Comparative Examples 22-24 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (128-166 ppm VS 174-209 ppm), a smaller roughness (10.6-11.5 nm VS 14.2-15.1 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Examples 38-47

[0292] The liquid crystal compositions of Examples 38-47 are prepared according to the parts by weight of each compound listed in Table 21. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Examples 38-47 are shown in Table 22 below.

TABLE-US-00024 TABLE 21 Formulations of the liquid crystal compositions of Examples 38-47 Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. 38 39 40 41 42 43 44 45 46 47 Host-11 100 100 100 100 100 Host-12 100 100 100 100 100 RM-1-1 0.4 0.4 0.4 0.4 0.4 0.8 0.8 0.8 0.8 0.8 AD-2 0.7 0.8 AD-1 0.7 0.8 AD-3 0.7 0.8 AD-4 0.7 0.8 AD-5 0.7 0.8

TABLE-US-00025 TABLE 22 Test results for performances of the liquid crystal compositions of Examples 38-47 Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. 38 39 40 41 42 43 44 45 46 47 Residue 193 213 164 187 165 169 191 150 165 154 conc. Ra 11.6 11.9 12.2 12.4 12.7 11.6 11.7 11.9 12.2 12.5 Alignment Good Good Good Good Good Good Good Good Good Good effect

[0293] It can be seen from the performance parameters of Examples 38-47 that, the liquid crystal composition comprising the self-aligning agent of general formula O in the present invention has a lower residue concentration (150-213 ppm), a smaller roughness (11.6-12.7 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Examples 48-57

[0294] The liquid crystal compositions of Examples 48-57 are prepared according to the parts by weight of each compound listed in Table 23. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Examples 48-57 are shown in Table 24 below.

TABLE-US-00026 TABLE 23 Formulations of the liquid crystal compositions of Examples 48-57 Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. 48 49 50 51 52 53 54 55 56 57 Host-13 100 100 100 100 100 Host-14 100 100 100 100 100 RM-2-1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 AD-2 1 1 AD-1 1 1 AD-3 1 1 AD-4 1 1 AD-5 1 1

TABLE-US-00027 TABLE 24 Test results for performances of the liquid crystal compositions of Example 48-57 Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. 48 49 50 51 52 53 54 55 56 57 Residue 165 178 140 160 146 172 184 146 167 152 conc. Ra 11.1 11.3 11.5 11.7 12.1 11.6 11.7 12.0 12.2 12.6 Alignment Good Good Good Good Good Good Good Good Good Good effect

[0295] It can be seen from the performance parameters of Examples 48-57 that, the liquid crystal composition comprising the self-aligning agent of general formula O in the present invention has a lower residue concentration (140-184 ppm), a smaller roughness (11.1-12.6 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Examples 58-62

[0296] The liquid crystal compositions of Examples 58-62 are prepared according to the parts by weight of each compound listed in Table 25. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Examples 58-62 are shown in Table 26 below.

TABLE-US-00028 TABLE 25 Formulations of the liquid crystal compositions of Examples 58-62 Ex. 58 Ex. 59 Ex. 60 Ex. 61 Ex. 62 Host-15 100 100 100 100 100 RM-1-1 0.4 0.4 0.4 0.4 0.4 AD-2 0.8 AD-1 0.8 AD-3 0.8 AD-4 0.8 AD-5 0.8

TABLE-US-00029 TABLE 26 Test results for performances of the liquid crystal compositions of Examples 58-62 Ex. 58 Ex. 59 Ex. 60 Ex. 61 Ex. 62 Residue conc. 144 156 119 139 126 Ra 10.5 10.7 11.0 11.2 11.5 Alignment Good Good Good Good Good effect

[0297] It can be seen from the performance parameters of Examples 58-62 that, the liquid crystal composition comprising the self-aligning agent of general formula O in the present invention has a lower residue concentration (119-175 ppm), a smaller roughness (10.5-12.5 nm) and a better alignment effect while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

[0298] Host liquid crystal compositions Host-16, Host-17, Host-18, Host-19, Host-20 and Host-21 are prepared according to each compound and weight percentage listed in Table 27, and are tested by filling the same between two substrates of a liquid crystal display device.

TABLE-US-00030 TABLE 27 Formulations and test results for performance parameters of host liquid crystal compositions General Component formula Weight percentage code code Host-16 Host-17 Host-18 Host-19 Host-20 Host-21 3PWO2 N-19 15 3 9 9 8 V2PWO4 N-55 6 2OPWO2 N-19 6 6 6 3CPWO2 N-21 5 7.5 2.5 2.5 8 1VCPWO2 N-53 2.5 3C1OWO2 N-7 11 2CC1OWO2 N-15 8.5 3CC1OWO2 N-15 11 3CWO2 N-2 13 13 13 12 3CWO4 N-2 2 2 2 5CWO2 N-2 5 5 VCWO2 N-49 13 2CCWO2 N-9 5 6.5 6.5 3CCWO2 N-9 3 12 13.5 13.5 13.5 6 VCCWO2 N-51 6 2CLWO2 N-12 6.5 2C1OWO2 N-7 5 2PWP3 N-24 5 2PWP2V1 N-54 5 3CPP2 M-13-2 13 9 13 8 13 10 3CPP2V1 M-13-9 5 3CPP1 M-13-1 7 10 3CPPC3 M-24 1 3CC2 M-1-2 20 17 14 14 14 15 5CC2 M-1-9 4 4 4 3CC4 M-1-4 6 6 6 3CCV1 M-1-6 9.5 10.5 10.5 10.5 10 2CPP2 M-13-2 8 5PP1 M-4 14.5 Total 100 100 100 100 100 100 Cp 75 75.7 77.2 76.8 75.6 76.6 n 0.1109 0.109 0.101 0.102 0.101 0.112 2.71 3.3 3.0 3.1 3.0 2.9 K.sub.11 14.5 14.6 15.1 12.1 15 15.1 K.sub.33 15.7 15.6 14.7 15.3 14.8 14.7 .sub.1 110 106 109 103 108 105

Comparative Examples 25-27 and Examples 63-66

[0299] The liquid crystal compositions of Comparative Examples 25-27 and Examples 63-66 are prepared according to the parts by weight of each compound listed in Table 28, The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 25-27 and Examples 63-66 are shown in Table 29 below.

TABLE-US-00031 TABLE 28 Formulations of the liquid crystal compositions of Comparative Examples 25-27 and Examples 63-66 Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. 25 Ex. 26 Ex. 27 63 64 65 66 Host-16 100 100 100 100 100 100 100 RM-1-1 0.3 0.3 0.3 0.3 0.3 RM-2-1 0.3 0.3 D-1 1 D-4 1 D-3 1 AD-2 1 AD-1 1 AD-3 1 AD-4 1

TABLE-US-00032 TABLE 29 Test results for performances of the liquid crystal compositions of Comparative Examples 25-27 Examples 63-66 Comp. Comp. Comp. Ex. 25 Ex. 26 Ex. 27 Ex. 68 Ex. 69 Ex. 70 Ex. 71 Residue 163 172 166 128 121 116 120 conc. Ra 15.2 15.6 15.7 11.9 11.7 11.8 12.1 t.sub.10 C. 8D NG 7D NG 7D NG 10D OK 10D OK 10D OK 10D OK Alignment Poor Fair Poor Good Good Good Good effect PTA.sub.(initial) 88.12 88.08 88.11 88.12 88.09 88.12 88.12 PTA.sub.(165 h) 87.77 87.73 87.75 87.86 87.85 87.87 87.87 PTA 0.35 0.35 0.36 0.26 0.24 0.25 0.25

[0300] It can be seen from the comparison between Examples 63-66 and Comparative Examples 25-27 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (116-128 ppm VS 163-172 ppm), a smaller roughness (11.7-12.1 nm VS 15.2-15.7 nm), a better low-temperature storage stability (10D OK VS 7-8D NG), a better alignment effect, and a better pre-tilt angle stability (0.24-0.26 VS 0.35-0.36) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 28-30 and Examples 67-70

[0301] The liquid crystal compositions of Comparative Examples 28-30 and Examples 67-70 are prepared according to the parts by weight of each compound listed in Table 30. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 28-30 and Examples 67-70 are shown in Table 31 below.

TABLE-US-00033 TABLE 30 Formulations of the liquid crystal compositions of Comparative Examples 28-30 and Examples 67-70 Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. 28 Ex. 29 Ex. 30 67 68 69 70 Host-17 100 100 100 100 100 100 100 RM-2-1 0.3 0.3 0.3 0.3 0.3 0.3 0.3 D-1 0.9 D-4 0.9 D-3 0.9 AD-2 0.9 AD-1 0.9 AD-3 0.9 AD-4 0.9

TABLE-US-00034 TABLE 31 Test results for performances of the liquid crystal compositions of Comparative Examples 28-30 and Examples 67-70 Comp. Comp. Comp. Ex. 28 Ex. 29 Ex. 30 Ex. 67 Ex. 68 Ex. 69 Ex. 70 Residue 168 189 172 120 123 117 119 conc. Ra 15.5 16.1 15.4 11.8 12 12.4 12.1 t.sub.10 C. 8D NG 8D NG 7D NG 10D OK 10D OK 10D OK 10D OK Alignment Fair Fair Poor Good Good Good Good effect PTA.sub.(initial) 88.1 88.12 88.09 88.14 88.08 88.14 88.14 PTA.sub.(165 h) 87.74 87.77 87.74 87.89 87.81 87.87 87.88 PTA 0.36 0.35 0.35 0.25 0.27 0.27 0.26

[0302] It can be seen from the comparison between Examples 67-70 and Comparative Examples 28-30 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (117-123 ppm VS 168-189 ppm), a smaller roughness (11.8-12.4 nm VS 15.4-16.1 nm), a better low-temperature storage stability (10D OK VS 7-8D NG), a better alignment effect, and a better pre-tilt angle stability (0.25-0.27 VS 0.35-0.36) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 31-33 and Examples 71-74

[0303] The liquid crystal compositions of Comparative Examples 31-33 and Examples 71-74 are prepared according to the parts by weight of each compound listed in Table 32. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 31-33 and Examples 71-74 are shown in Table 33 below.

TABLE-US-00035 TABLE 32 Formulations of the liquid crystal compositions of Comparative Examples 31-33 and Examples 71-74 Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. 31 Ex. 32 Ex. 33 71 72 73 74 Host-18 100 100 100 100 100 100 100 RM-1-1 0.3 0.3 0.3 0.3 0.3 0.3 0.3 D-1 1 D-4 1 D-3 1 AD-2 1 AD-1 1 AD-3 1 AD-4 1

TABLE-US-00036 TABLE 33 Test results for performances of the liquid crystal compositions of Comparative Examples 31-33 and Examples 71-74 Comp. Comp. Comp. Ex. 31 Ex. 32 Ex. 33 Ex. 71 Ex. 72 Ex. 73 Ex. 74 Residue 158 157 159 112 105 108 111 conc. Ra 14.3 14.9 14.5 11.7 11.8 11.2 41.3 t.sub.10 C. 8D NG 7D NG 8D NG 10D OK 10D OK 10D OK 10D OK Alignment Fair Fair Poor Good Good Good Good effect PTA.sub.(initial) 88.14 88.11 88.09 88.15 88.09 88.15 88.13 PTA.sub.(165 h) 87.81 87.78 87.86 87.92 87.85 87.92 87.89 PTA 0.33 0.33 0.33 0.23 0.24 0.23 0.24

[0304] It can be seen from the comparison between Examples 71-74 and Comparative Examples 31-33 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (105-112 ppm VS 157-159 ppm), a smaller roughness (11.2-11.8 nm VS 14.3-14.9 nm), a better low-temperature storage stability (10D OK VS 7-8D NG), a better alignment effect, and a better pre-tilt angle stability (0.23-0.24 VS 0.33) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 34-36 and Examples 75-78

[0305] The liquid crystal compositions of Comparative Examples 34-36 and Examples 75-78 are prepared according to the parts by weight of each compound listed in Table 34. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 34-36 and Examples 75-78 are shown in Table 35 below.

TABLE-US-00037 TABLE 34 Formulations of the liquid crystal compositions of Comparative Examples 34-36 and Examples 75-78 Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. 34 Ex. 35 Ex. 36 75 76 77 78 Host-19 100 100 100 100 100 100 100 RM-1-1 0.3 0.3 0.3 0.3 0.3 0.3 0.3 D-1 0.8 D-4 0.8 D-3 0.8 AD-2 0.8 AD-1 0.8 AD-3 0.8 AD-4 0.8

TABLE-US-00038 TABLE 35 Test results for performances of the liquid crystal compositions of Comparative Examples 34-36 and Examples 75-78 Comp. Comp. Comp. Ex. 34 Ex. 35 Ex. 36 Ex. 75 Ex. 76 Ex. 77 Ex. 78 Residue 169 173 167 115 128 120 122 conc. Ra 15.8 15.6 15.1 12.5 12.4 12.4 12.2 t.sub.10 C. 8D NG 6D NG 7D NG 10D OK 10D OK 10D OK 10D OK Alignment Fair Fair Poor Good Good Good Good effect PTA.sub.(initial) 88.12 88.11 88.09 88.11 88.1 88.14 88.11 PTA.sub.(165 h) 87.76 87.75 87.74 87.85 87.84 87.9 87.86 PTA 0.36 0.36 0.35 0.26 0.26 0.24 0.25

[0306] It can be seen from the comparison between Examples 75-78 and Comparative Examples 34-36 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (115-128 ppm VS 167-173 ppm), a smaller roughness (12.2-12.5 nm VS 15.1-15.8 nm), a better low-temperature storage stability (10D OK VS 6-8D NG), a better alignment effect, and a better pre-tilt angle stability (0.24-0.26 VS 0.35-0.36) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 37-39 and Examples 79-82

[0307] The liquid crystal compositions of Comparative Examples 37-39 and Examples 79-82 are prepared according to the parts by weight of each compound listed in Table 36. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 37-39 and Examples 79-82 are shown in Table 37 below.

TABLE-US-00039 TABLE 36 Formulations of the liquid crystal compositions of Comparative Examples 37-39 and Examples 79-82 Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. 37 Ex. 38 Ex. 39 79 80 81 82 Host-20 100 100 100 100 100 100 100 RM-2-1 0.3 0.3 0.3 0.3 0.3 0.3 0.3 D-1 1 D-4 1 D-3 1 AD-2 1 AD-1 1 AD-3 1 AD-4 1

TABLE-US-00040 TABLE 37 Test results for performances of the liquid crystal compositions of Comparative Examples 37-39 and Examples 79-82 Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. 37 Ex. 38 Ex. 39 79 80 81 82 Residue 145 139 140 94 96 90 89 conc. Ra 14.1 14 13.8 9.8 9.5 9.4 9.4 t.sub.10 C. 6D NG 8D NG 8D NG 10D OK 10D OK 10D OK 10D OK Alignment Fair Poor Poor Good Good Good Good effect PTA.sub.(initial) 88.11 88.09 88.1 88.14 88.11 88.14 88.13 PTA.sub.(165 h) 87.79 87.78 87.78 87.93 87.89 87.93 87.92 PTA 0.32 0.31 0.32 0.21 0.22 0.21 0.21

[0308] It can be seen from the comparison between Examples 79-82 and Comparative Examples 37-39 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (89-96 ppm VS 139-145 ppm), a smaller roughness (9.4-9.8 nm VS 13.8-14.1 nm), a better low-temperature storage stability (10D OK VS 6-8D NG), a better alignment effect, and a better pre-tilt angle stability (0.21-0.22 VS 0.31-0.32) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

Comparative Examples 40-42 and Examples 83-86

[0309] The liquid crystal compositions of Comparative Examples 40-42 and Examples 83-86 are prepared according to the parts by weight of each compound listed in Table 38. The obtained liquid crystal compositions are tested for performance by filling each liquid crystal composition into a non-aligned test cell (cell gap d is 3.5 m, with ITO coatings (structured ITO for multi-domain switching mode) on both substrates, no alignment layer, and no passivation layer). The test results for relevant performances of the liquid crystal compositions of Comparative Examples 40-42 and Examples 83-86 are shown in Table 39 below.

TABLE-US-00041 TABLE 38 Formulations of the liquid crystal compositions of Comparative Examples 40-42 and Examples 83-86 Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. 40 Ex. 41 Ex. 42 83 84 85 86 Host-21 100 100 100 100 100 100 100 RM-2-1 0.3 0.3 0.3 0.3 0.3 0.3 0.3 D-1 1 D-4 1 D-3 1 AD-2 1 AD-1 1 AD-3 1 AD-4 1

TABLE-US-00042 TABLE 39 Test results for performances of the liquid crystal compositions of Comparative Examples 40-42 and Examples 83-86 Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. 40 Ex. 41 Ex. 42 83 84 85 86 Residue 149 144 158 101 97 102 102 conc. Ra 14.9 14.6 14.4 10.8 10.5 10.4 10.4 t.sub.10 C. 8D NG 7D NG 7D NG 10D OK 10D OK 10D OK 10D OK Alignment Fair Poor Poor Good Good Good Good effect PTA.sub.(initial) 88.09 88.09 88.13 88.14 88.09 88.13 88.11 PTA.sub.(165 h) 87.77 87.76 87.8 87.9 87.85 87.88 87.89 PTA 0.32 0.33 0.33 0.24 0.24 0.25 0.22

[0310] It can be seen from the comparison between Examples 83-86 and Comparative Examples 40-42 that, through structural optimization of the self-aligning agent, the liquid crystal composition of the present invention has a smaller polymer residue (97-102 ppm VS 144-158 ppm), a smaller roughness (10.4-10.8 nm VS 14.4-14.9 nm), a better low-temperature storage stability (10D OK VS 7-8D NG), a better alignment effect, and a better pre-tilt angle stability (0.22-0.25 VS 0.32-0.33) while maintaining an appropriate clearing point, an appropriate optical anisotropy, an appropriate absolute value of dielectric anisotropy, a larger K value (K.sub.11 and K.sub.33) and a smaller rotational viscosity.

[0311] The above embodiments are merely illustrative of the technical concepts and the features of the present invention, are included merely for purposes of illustration and implement of the present invention, and are not intended to limit the scope of the present invention. Equivalent variations or modifications are intended to be included within the scope of the present invention.

SELF ALIGNMENT AGENT AND LIQUID CRYSTAL COMPOSITION THEREOF

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Abstract

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