CN112812014B - Compound, liquid crystal composition and liquid crystal display - Google Patents
Compound, liquid crystal composition and liquid crystal display Download PDFInfo
- Publication number
- CN112812014B CN112812014B CN201911120055.5A CN201911120055A CN112812014B CN 112812014 B CN112812014 B CN 112812014B CN 201911120055 A CN201911120055 A CN 201911120055A CN 112812014 B CN112812014 B CN 112812014B
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- group
- carbon atoms
- atoms
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 128
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 126
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- -1 tetrahydropyran-2, 5-diyl Chemical group 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000004976 cyclobutylene group Chemical group 0.000 claims description 7
- 125000004979 cyclopentylene group Chemical group 0.000 claims description 7
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000006850 spacer group Chemical group 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 2
- NSUDGNLOXMLAEB-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)pentanoic acid Chemical group OC(=O)CCCCOC1=CC=CC(O)=C1C=O NSUDGNLOXMLAEB-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 15
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000010410 layer Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000007787 solid Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000008034 disappearance Effects 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001338 self-assembly Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 2
- 125000006437 ethyl cyclopropyl group Chemical group 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 2
- 125000006441 n-butyl cyclopropyl group Chemical group 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 125000006434 propyl cyclopropyl group Chemical group 0.000 description 2
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000006442 t-butyl cyclopropyl group Chemical group 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/60—Maleic acid esters; Fumaric acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention relates to a compound shown in the following formula I, a liquid crystal composition and a liquid crystal display. The compounds of the present invention can be used as self-assembled photoalignment agents (SAPA) in liquid crystal compositions, by photoalignment of liquid crystal compositions having positive or negative dielectric anisotropy, liquid Crystal (LC) display devices having in-plane alignment can be manufactured. The compound shown in the formula I can obtain the photo-alignment film with good stability through polymerization, can play roles of insulating an alignment layer and horizontally aligning liquid crystal molecules, can avoid the process of the alignment layer, simplifies the process of a liquid crystal display element or a liquid crystal display, and improves the production efficiency.
Description
Technical Field
The invention relates to a compound capable of realizing self-assembly photoalignment function and a liquid crystal composition containing the compound, and belongs to the field of liquid crystal display.
Background
Currently, alignment of liquid crystal molecules can be achieved using a specific polyimide alignment film. As a method of aligning a liquid crystal alignment film for imparting alignment control ability, a brush polishing method has been widely used. However, the brush polishing method for rubbing the surface of a liquid crystal alignment film containing polyimide or the like has problems of dust generation and static electricity generation. Further, in recent years, the liquid crystal display element has been made higher in definition and the surface of the liquid crystal alignment film cannot be uniformly rubbed with a cloth due to irregularities caused by the electrode on the corresponding substrate or the switching active element for driving the liquid crystal, and thus uniform liquid crystal alignment cannot be achieved.
On the other hand, the polymerizable mesogenic unit RMs is a very popular and important subject in the display industry, and the possible application fields include Polymer Stabilized Alignment (PSA) liquid crystal display, polymer stabilized blue phase (PS-BP) liquid crystal display, and patterned retardation film PATTERN RETARDER FILM. In a liquid crystal display element in which a polymer is stably aligned, the alignment of liquid crystal molecules can be controlled by using the polymer.
In the prior art, there is disclosed a report that liquid crystal display elements such as PSA-VA, PSA-OCB, PS-IPS/FFS and PS-TN can be expected to achieve such effects by using a combination of a polymer and a polar compound in a liquid crystal display element without an alignment film by using a liquid crystal composition containing a polymer and a polar compound to control alignment of liquid crystal analysis, but LC mixtures and RMs have some drawbacks in application to IPS/FFS displays. For example, the panel process requires the application of alignment layers, which not only complicates the process and affects the throughput of the production line, but also results in the emission of organic contaminants, and in addition, n.a. Clark et al Langmuir2010,26 (22), 17482-17488 have described that the following structural compounds may be used: Self-assembly on a substrate to give a monolayer capable of being photoaligned to induce homeotropic alignment of liquid crystals. However, a separate step of self-assembly is required before the LC cell is fabricated, and disadvantages such as reversibility of alignment after exposure to light are reported.
Disclosure of Invention
The present invention provides a compound capable of self-assembling photoalignment, which can perform alignment without using a polyimide alignment film when a liquid crystal composition containing the compound is applied to a liquid crystal display element, and has a simplified method of liquid crystal alignment and stable alignment.
In order to achieve the above object, the present invention provides a compound having the structural formula shown in the following formula I,
Wherein P 11、P12 each independently represents P 1、P1-Sp-、-Z3 -H,-Z 3-L1, H atoms, F atoms or linear or branched alkyl having 1 to 12C atoms, wherein one or more non-adjacent-CH 2 -groups are optionally replaced by-C (L 0)＝C(L00)-、-C≡C-、-N(L00) -, -O-, -S-, -CO-O-, -O-CO-or-O-CO-O-, one or more H atoms are optionally replaced by F atoms, cl atoms, br atoms, I atoms, CN, P 1 or P 1 -Sp-, and at least one of P 11 and P 12 represents a group P 1 or P 1 -Sp-;
K 1、K2、K3 each independently represents an aromatic, heteroaromatic, alicyclic, heterocyclic or fused cyclic group of 4 to 25 carbon atoms, wherein any one of the-CH 2 -groups on the ring is optionally replaced by-O-, -S-or-CO-, at least one or more H atoms being optionally substituted by L 1;
L 1 represents an F atom, an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms, a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms or-Sp-P 1, and any of-CH 2 -is optionally replaced by cyclopentylene, cyclobutylene or cyclopropylene;
Z 1、Z2、Z3 each independently represents a single bond 、-O-、-S-、-CO-、-COO-、-OCO-、-OCOO-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-(CH2)n1-、-CF2CH2-、-CH2CF2-、-(CF2)n1-、-(CL0L00)n1-、-CH＝CH-、-C≡C-、-CF＝CF-、-CH＝CH-COO-、-OCO-CH＝CH-、-OCO-CH＝CH-COO-、-N＝N-、 Or
N1 represents 1,2, 3 or 4; m, n, o, q each independently represents 0, 1,2, 3 or 4, and m+o+n q is not less than 2;
Each G 1、G2、G3 independently represents-Sp 1-R1、-Sp2-R2、-Sp3-R3 or R, wherein one or more non-adjacent-CH 2 -is optionally replaced by-O-; r represents
P represents 1, 2 or 3; x represents a divalent, trivalent or tetravalent group;
R 1、R2、R3、R4 each independently represents-NL 11、-OL11、-SL11、-COOL11、-CHO、-CONL11 OrP 1 represents a polymerizable group;
l 0、L00、L11 each independently represents an H atom or an alkyl group of 1 to 12C atoms;
Sp and Sp 1、Sp2、Sp3、Sp4、Sp5 each independently represent a spacer or a single bond.
In another aspect, the present invention provides a liquid crystal composition comprising one or more compounds of formula I.
In yet another aspect of the present invention, there is provided a liquid crystal display element or display comprising a compound of the present invention, or a liquid crystal composition of the present invention, said display element or display being an active matrix display element or display or a passive matrix display element or display.
The compounds of the present invention are capable of acting as self-assembling photoaligners (SAPAs), utilizing the polar side groups of the compounds to interact with the substrate surface, thereby enabling SAPAs to be separated from the LC mixture after filling the LC cell, forming a layer on the substrate that can be photoaligned with linearly polarized UV light. Then, the compound shown in the formula I is subjected to in-situ gradual polymerization by polarized ultraviolet irradiation to obtain a photo-alignment film with good stability, the photo-alignment film can play roles in insulation of an alignment layer and horizontal alignment of liquid crystal molecules, and the liquid crystal follows the alignment of the aligned SAPA so as to give uniform plane alignment across the whole display. Therefore, the alignment layer manufacturing process can be avoided, the manufacturing process of the liquid crystal display element or the liquid crystal display is simplified, and the production efficiency is improved.
Further, the liquid crystal composition of the present invention has a low viscosity, and can realize a rapid response while having a moderate dielectric anisotropy Δεand a moderate optical anisotropy Δn.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of a compound shown in the formula I1-1 a.
Detailed Description
[ Compound ]
The above-mentioned compounds of formula I of the present invention are preferably selected from the group consisting of compounds of the following formulae I1 to I11:
Wherein r represents 0, 1, 2 or 3; the remaining groups and parameters have the meanings indicated above for formula I.
Preferably, the compound of formula I is selected from the group consisting of compounds of formulas I1-1 through I11-3:
Wherein r represents 0, 1, 2 or 3; the remaining groups and parameters have the meanings indicated above for formula I.
More preferably, the compound of formula I is selected from the group consisting of compounds of formulas I1-1a through I11-3 a:
The method for producing the compound of formula I of the present invention is not particularly limited. One embodiment of the method is, for example, a method of synthesizing according to the following synthesis route, but not limited to this:
Scheme 1:
Scheme 2:
Wherein G 1、G2、L1、L00、Sp1、Sp2, r are as defined above, L represents a hydrogen atom, a methyl group, a trifluoromethyl group, etc., and L' represents L 1 or an aromatic group.
The raw materials and reagents in the general formula can be purchased through commercial paths, and the methods of the method principle, the operation process, the conventional post-treatment, the silica gel column passing, the recrystallization purification and the like are well known to the synthesis personnel in the field, so that the synthesis process can be completely realized, and the target product is obtained.
The reactions of all steps of all the above methods are carried out in a solvent selected from at least one of tetrahydrofuran, N-dimethylformamide, ethanol, methanol, methylene chloride, acetone, toluene and deionized water.
[ Liquid Crystal composition ]
The liquid crystal composition of the present invention comprises one or more compounds of the present invention.
In the liquid crystal composition of the present invention, the content of the compound represented by formula I in the liquid crystal composition is preferably 0.01 to 10%. Preferably, the content of the compound shown in the formula I in the liquid crystal composition is 0.01-1%.
In one embodiment of the liquid crystal composition of the present invention, one or more polymerizable compounds represented by formula P may be further contained,
Pa-(Spa)s1-A2-(Z-A1)n2-(Spb)s2-Pb P
Wherein P a、Pb each independently represents a polymerizable group; sp a、Spb each independently represents a spacer group;
s1, s2 are each independently 0 or 1;
Each a 1、A2 independently represents a group selected from the group consisting of:
a) A group consisting of trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene and 4,4' -dicyclohexylene, wherein one or more non-adjacent-CH 2 the groups are optionally replaced by-O-or-S-, one or more H atoms are optionally replaced by F atoms,
B) A group consisting of 1, 4-phenylene and 1, 3-phenylene, wherein one or two CH groups are optionally replaced by N, one or more H atoms are optionally replaced by L,
C) A group consisting of tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, tetrahydrofuran-2, 5-diyl, cyclobutane-1, 3-diyl, piperidine-1, 4-diyl, thiophene-2, 5-diyl and selenophene-2, 5-diyl, wherein one or more H atoms are optionally monosubstituted or polysubstituted by L,
D) From the following components
A group of;
Wherein one or more H atoms in these groups are optionally replaced by L, and/or one or more double bonds are optionally replaced by single bonds, and/or one or more CH are optionally replaced by N; n2 is 0, 1, 2 or 3;
Z represents-CO-O-, -O-CO-, -CH 2O-、-OCH2-、-CF2O-、-OCF2 -, a linear alkylene group having 2 to 4 carbon atoms-O-, -CO-, -C (R 0R00)-、-CH2CF2-、-CF2CF2 -or a single bond;
L represents, independently for each occurrence, F atoms, cl atoms, CN, SCN, SF 5 or optionally fluorinated straight-chain or branched alkyl groups having 1 to 12C atoms, alkoxy groups, alkylcarbonyl groups, alkoxycarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups;
R 0、R00 each independently of the other represents an H atom, an F atom or a linear or branched alkyl radical having 1 to 12C atoms, wherein one or more H atoms are optionally replaced by F atoms; m represents-O-, -S-, -CH 2-、-CHY1 -or-CY 1Y2 -;
Y 1、Y2 each independently of the other represents an H atom, an F atom, a Cl atom, CN or a linear or branched alkyl radical having 1 to 12C atoms, wherein one or more H atoms are optionally replaced by F atoms.
In the case of containing the compound represented by the formula P, the liquid crystal composition of the present invention preferably has a content of the compound represented by the formula P in the liquid crystal composition of 0.01 to 10%. Preferably, the content of the compound represented by formula P in the liquid crystal composition is 0.01 to 1%.
Preferably, the polymerizable compound of formula P is selected from polymerizable compounds represented by the following formula P1,
Wherein P a、Pb each independently represents a polymerizable group; sp a、Spb each independently represents a spacer group;
l 1 represents an F atom, a Cl atom, an alkyl group having 1 to 12C atoms, an alkoxy group having 1 to 12C atoms;
r represents 0, 1 or 2.
Preferably, the polymerizable compound represented by the formula P1 is selected from the group consisting of compounds represented by the following formulas P1-1 to P1-3,
In one embodiment of the liquid crystal composition of the present invention, one or more compounds represented by formula II and/or compounds represented by formula III may be further contained,
Wherein in the formula II,RepresentationOrRepresentationOr
R 5、R6 each independently represents an alkyl group having 1 to 12 carbon atoms, wherein one or more non-adjacent-CH 2 -groups are optionally replaced by-O-, -ch=ch-, -CO-, -O-CO-, or-CO-O-;
Z 4 represents -CH2CH2-、-CH＝CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-COO-、-OCO-、-C2F4-、-CF＝CF- or a single bond;
In the formula III, the compound of the formula III, Each independently representsOr
R 7、R8 is independently an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms.
Preferably, the one or more compounds of formula II are selected from the group consisting of the following compounds of formulas II-1 to II-17:
Preferably, the one or more compounds of formula III are selected from the group consisting of compounds of formulas III-1 to III-4,
Wherein R 71、R81 each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms; r 82 represents an alkoxy group having 1 to 5 carbon atoms. Examples of the alkenyl group having 2 to 6 carbon atoms include a vinyl group, a 2-propenyl group and a 3-pentenyl group.
In the case where the compound represented by the formula II is contained in the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula II to be added to the liquid crystal composition is not particularly limited, and the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I may be, for example, 15 to 70%, preferably 30 to 70%. In the case where the compound represented by the formula III is contained in the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula III to be added to the liquid crystal composition is not particularly limited, and may be, for example, 1 to 30%, preferably 5 to 20%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
By combining the compound shown in the formula II and the compound shown in the formula I in the invention in the liquid crystal composition, the beneficial effects of improving the intersolubility and improving the response speed are obtained. By using the compound represented by formula III in combination in the liquid crystal composition of the present invention, a liquid crystal composition having a large optical anisotropy Δn and a low rotational viscosity is obtained.
In one embodiment of the liquid crystal composition of the present invention, one or more compounds of formula IV,
Wherein,
Each independently represents a group selected from the group consisting of ①、②:
① Trans 1, 4-cyclohexylene, 1, 4-cyclohexenylene in which one or more non-adjacent-CH 2 -groups are optionally substituted by-O-or-S-;
② 1, 4-phenylene, wherein one or two CH groups are optionally substituted with N and one or two H atoms are optionally substituted with F atoms;
R 9 represents A linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms;
X 1、X2 each independently represents an H atom or an F atom;
Y 3 represents an F atom, a linear alkyl group having 1 to 6 carbon atoms, a linear alkoxy group having 1 to 6 carbon atoms or a linear alkenyl group having 2 to 6 carbon atoms, wherein one or more hydrogen atoms are optionally replaced by an F atom;
Z 5 represents a single bond 、-CH2-、-CH2CH2-、-(CH2)3-、-(CH2)4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-OCH2-、-CH2O-、-CF2CH2-、-CH2CF2-、-C2F4- or-cf=cf-;
r represents 0, 1 or 2.
Preferably, the one or more compounds of formula IV are selected from the group consisting of compounds of formulas IV 1-IV 15:
Wherein R 9 has the same meaning as R 9 in the compound represented by the above formula IV, and each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 8 carbon atoms, and any one or more of-CH 2 -groups represented by R 9 is optionally replaced by cyclopentylene, cyclobutylene, or cyclopropylene; (F) in the formulae IV 1 to IV 6 each independently represents H or F; - (O) CF 3 in formula IV 7 represents-CF 3 or-OCF 3.
Examples of the group obtained by substituting one or more non-adjacent ones of the alkyl groups having 1 to 10 carbon atoms represented by R 9 in the compound represented by the above formula IV include cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopropyl, ethylcyclopropyl, propylcyclopropyl, isopropylcyclopropyl, n-butylcyclopropyl, isobutylcyclopropyl, tert-butylcyclopropyl, methylcyclobutyl, ethylcyclobutyl, propylcyclobutyl, isopropylcyclobutyl, n-butylcyclopentylene, isobutylcyclobutyl, tert-butylcyclopentylene, methylcyclopentyl, ethylcyclopentyl, isopropylcyclopentylene, propylcyclopentyl, isopropylcyclopentylene, n-butylcyclopentylene, isobutylcyclopentyl and isobutylcyclopentyl. Among the groups represented by R 9, cyclopropyl or cyclopentyl is preferable from the viewpoints of rotational viscosity, solubility and clearing point of the liquid crystal compound.
In the case where the compound represented by the formula IV is contained in the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula IV to be added to the liquid crystal composition is not particularly limited, and may be, for example, 1 to 55%, preferably 30 to 50%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
The compound shown in the formula IV is positive dielectric anisotropy, and the threshold voltage of the liquid crystal composition can be further adjusted by containing the compound shown in the formula IV in the liquid crystal composition.
In one embodiment of the liquid crystal composition of the present invention, one or more compounds represented by formula V,
Wherein R 10、R11 each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any one or more of R 10、R11 is not substituted with-CH 2 -optionally substituted with cyclopentylene, cyclobutylene or cyclopropylene; z 6、Z7 each independently represents a single bond, -CH 2CH2 -, or-CH 2 O-;
each independently represents/> Or
S represents 1 or 2; t represents 0, 1 or 2.
Preferably, the aforementioned one or more compounds of formula V are selected from the group consisting of compounds of formula V-1 to formula V-15,
Wherein R 10、R11 in the compounds represented by the formulas V-1 to V-15 has the same meaning as R 10、R11 in the compounds represented by the formula V, and each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any one or more of non-adjacent-CH 2 -groups represented by R 10、R11 -are optionally substituted by cyclopentylene, cyclobutylene or cyclopropylene.
The compound shown in the formula V and the compound shown in the formula I are combined in the liquid crystal composition, so that the beneficial effect of increasing the negative dielectric anisotropy of the liquid crystal composition is obtained.
As the group obtained by substituting one or more non-adjacent-CH 2 -groups in the alkyl group having 1 to 10 carbon atoms represented by R 10、R11 in the above formula V with a cyclopropylene group, a cyclobutylene group or a cyclopentylene group, examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopropyl, ethylcyclopropyl, propylcyclopropyl, isopropylcyclopropyl, n-butylcyclopropyl, isobutylcyclopropyl, t-butylcyclopropyl, methylcyclobutyl, ethylcyclobutyl, propylcyclobutyl, isopropylcyclobutyl, n-butylcyclobutyl, isobutylcyclobutyl, t-butylcyclobutyl, methylcyclopentyl, ethylcyclopentyl, propylcyclopentyl, isopropylcyclopentyl, n-butylcyclopentyl, and isobutylcyclopentyl. Among the groups represented by R 10、R11, cyclopropyl, cyclobutyl or cyclopentyl are preferable from the viewpoints of the rotational viscosity, solubility and clearing point of the liquid crystal compound.
In the case where the compound represented by the formula V is contained in the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula V to be added to the liquid crystal composition is not particularly limited, and may be, for example, 10 to 65%, preferably 20 to 50% based on the total amount of other components in the liquid crystal composition excluding the compound represented by the formula I.
One embodiment of the liquid crystal composition according to the invention further comprises one or more compounds of formula VI,
Wherein R 12、R13 each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any one or more of R 5、R6 is not substituted with-CH 2 -optionally substituted with cyclopentylene, cyclobutylene or cyclopropylene; w represents-O- -S-or-CH 2 O-.
Preferably, the compound of formula VI is selected from the group consisting of compounds of formulas VI-1 to VI-6:
Wherein R 131 represents an alkyl group having 2 to 6 carbon atoms.
In the case where the compound represented by the formula VI is contained in the liquid crystal composition of the present application, the amount (mass ratio) of the compound represented by the formula VI to be added to the liquid crystal composition is not particularly limited, and may be, for example, 1 to 15%, preferably 2 to 10%, based on the total amount of other components in the liquid crystal composition excluding the compound represented by the formula I. By including the compound represented by the formula VI in the liquid crystal composition of the present application, the liquid crystal composition can have a large negative dielectric anisotropy, which is advantageous in reducing the driving voltage of the device.
In addition, various functional dopants may be added to the liquid crystal composition of the present invention, and when the dopants are contained, the content of the dopants is preferably 0.01 to 1% by mass based on the liquid crystal composition, and examples of the dopants include antioxidants, light stabilizers, and chiral agents.
Examples of the antioxidant and the light stabilizer include,
U represents an integer of 1 to 10.
The photoalignment of the liquid crystal composition can be induced by irradiating the liquid crystal composition of the present invention with light, preferably with linearly polarized light. In a preferred embodiment, the linearly polarized light is ultraviolet light, and the polymerizable compound is cured by irradiation with ultraviolet light to cause immobilization of the alignment, whereby the self-assembled photoalignment agent and the polymerizable compound can be simultaneously photo-cured.
The liquid crystal display comprises the liquid crystal composition of the invention, and the liquid crystal display is an active matrix display or a passive matrix display.
Alternatively, the aforementioned liquid crystal display may be, for example, an IPS or FFS display.
The structure of the liquid crystal display of the present invention is not limited as long as the compound of the present invention represented by the formula I is contained in the liquid crystal composition used in the liquid crystal display, and a person skilled in the art can select a suitable structure of the liquid crystal display according to the desired performance.
As an embodiment of the liquid crystal display of the present invention, for example, the following structure is given: the liquid crystal display device comprises a first substrate, a second substrate and a liquid crystal composition formed by a compound shown in a formula I, a compound shown in a formula P and other liquid crystal molecules, wherein the compound is arranged between the first substrate and the second substrate, the first substrate and the second substrate are arranged in parallel and opposite to each other, the first substrate is provided with a common electrode, the second substrate is provided with a pixel electrode, and spacers are scattered between the first substrate and the second substrate.
Examples
In order to more clearly illustrate the present invention, the present invention will be further described with reference to preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and that this invention is not limited to the details given herein.
In the invention, the preparation method is a conventional method unless specified otherwise, the raw materials used can be obtained from the disclosed commercial path unless specified otherwise, the percentages refer to mass percentages, the temperature is in degrees centigrade (DEG C), the liquid crystal compound is also a liquid crystal monomer, and the specific meanings and testing conditions of other symbols are as follows:
Cp represents a liquid crystal clearing point (DEG C), and is tested by DSC quantification;
Δn represents optical anisotropy, Δn=n e-no, where n o is the refractive index of ordinary light, n e is the refractive index of extraordinary light, and the test conditions are 25±2 ℃,589nm, and abbe refractometer test;
Delta epsilon represents dielectric anisotropy, delta epsilon=epsilon-epsilon, wherein epsilon is the dielectric constant parallel to the molecular axis, epsilon is the dielectric constant perpendicular to the molecular axis, and the test condition is 25+/-0.5 ℃ and 20-micrometer parallel box, INSTEC is ALCT-IR1 test;
VHR represents a voltage holding ratio (%), and the test conditions were 20±2 ℃, voltage ±5V, pulse width 10ms, and voltage holding time 16.7ms. The test equipment is a TOYO Model6254 liquid crystal performance comprehensive tester;
gamma 1 represents the rotational viscosity (mPas) under the test conditions of 25+ -0.5deg.C, 20 μm parallel box, INSTEC: ALCT-IR1 test.
The structures of the liquid crystal monomers used in the examples of the present invention are represented by codes, and the codes of the liquid crystal ring structures, the terminal groups and the linking groups are represented by the following tables 1 and 2.
Table 1: corresponding code of ring structure
Table 2: corresponding codes of end groups and linking groups
Examples:
the code is CC-Cp-V1;
The code is PGP-Cpr1-2;
The code is CPY-2-O2;
The code is CCY-3-O2;
the code is COY-3-O2;
The code is CCOY-3-O2; /(I)
The code is Sb-CpO-O4;
The code is Sc-CpO-O4;
the code is COYL-Cprl-O2;
the code is COYL-1-OV1.
Example 1
The structural formula of the compound is shown as the following formula I1-1 a:
Step 1
Into the reaction flask were charged 11.5g (0.05 mol) of compound 1-1 and 15.7g (0.05 mol) of compound 1-2, 12.7g (0.05 mol) of pinacol biborate, 16.6g (0.12 mol) of potassium carbonate, 0.5g of Pd (dppf) 2Cl2, 300mL of toluene and 100mL of water. Heating to reflux under the protection of nitrogen, reacting for 2 hours, and detecting the disappearance of the raw materials by using a dot plate. Adding water and toluene, stirring, extracting the water layer with toluene twice, combining toluene layers, washing with water, performing silica gel column chromatography, spin-drying the solvent, and recrystallizing with toluene and ethanol for 3 times to obtain white solid 20.5g, and GC:99.1%.
Step 2
26.1G (0.067 mol) of compound 1-3, 12.6g (0.143 mol) of methacrylic acid, 100ml of methylene chloride are added into a reaction flask, stirred and fully dissolved, 29.5g (0.143 mol) of DCC is added at room temperature, then stirred at room temperature for 4 hours, and the point plate detects that the compound 1-3 disappears; adding water, stirring, separating, extracting the water layer with dichloromethane twice, combining dichloromethane layers, washing with water, drying with anhydrous sodium sulfate, spin-drying the solvent, dissolving with toluene, performing silica gel column chromatography, and recrystallizing with toluene and ethanol for 3 times to obtain white solid 19.1g, and HPLC:99.7%.
Step 3
19.6G (0.043 mol) of compounds 1-4 and 250mL of tetrahydrofuran were added to the reaction flask. 50mL of 2N aqueous hydrochloric acid was added at room temperature, and the reaction was carried out at room temperature for 4 hours, whereupon the spot plate detects the disappearance of compounds 1-4. Adding water and toluene, stirring, extracting the water layer with toluene twice, combining toluene layers, washing with water, performing silica gel column chromatography, spin-drying the solvent, and recrystallizing with toluene and ethanol for 3 times to obtain 13.5g of white solid, wherein GC is 98.3%.
Step 4
17.3G (0.038 mol) of Compound 1-5,6.4g (0.080 mmol) of 2-chloroethanol, 11.0g (0.080 mmol) of potassium carbonate and 150mL of DMF are added into a reaction flask, heated and stirred, and reacted at 100 ℃ until the spot-size detection of Compound 1-5 disappears. Adding water and toluene, stirring, extracting the water layer with toluene for two times, combining toluene layers, washing with water, performing silica gel column chromatography, spin-drying the solvent, and recrystallizing with toluene and petroleum ether for 3 times to obtain I1-1a, 11.5g of white solid, and LC:99.3%. The nuclear magnetic resonance spectrum of the obtained compound shown in the formula I1-1a is shown in the attached figure 1.
Example 2
The structural formula of the compound is shown as the following formula I1-1I:
Step 1
Into a reaction flask were charged 18.1g (0.05 mol) of Compound 2-1 and 11.6g (0.05 mol) of Compound 2-2, 12.7g (0.05 mol) of pinacol biborate, 16.6g (0.12 mol) of potassium carbonate, 0.5g of Pd (dppf) 2Cl2, 300mL of toluene and 100mL of water. Heating to reflux under the protection of nitrogen, reacting for 2 hours, and detecting the disappearance of the raw materials by using a dot plate. Adding water and toluene, stirring, extracting the water layer with toluene twice, combining toluene layers, washing with water, performing silica gel column chromatography, spin-drying the solvent, and recrystallizing with toluene and ethanol for 3 times to obtain white solid 20.5g, and GC:99.1%.
Step 2
29.2G (0.067 mol) of compound 2-3, 12.6g (0.143 mol) of methacrylic acid and 100ml of methylene chloride are added into a reaction bottle, stirred and fully dissolved, 29.5g (0.143 mol) of DCC is added at room temperature, and then stirred at room temperature for 4 hours, and the point plate detects that the compound 2-3 disappears; adding water, stirring, separating, extracting the water layer with dichloromethane twice, combining dichloromethane layers, washing with water, drying with anhydrous sodium sulfate, spin-drying the solvent, dissolving with toluene, performing silica gel column chromatography, and recrystallizing with toluene and ethanol for 3 times to obtain white solid 19.1g, and HPLC:99.7%.
Step 3
21.7G (0.043 mol) of Compound 2-4 and 250mL of tetrahydrofuran were added to the reaction flask. 50mL of 2N aqueous hydrochloric acid was added at room temperature, and the reaction was carried out at room temperature for 4 hours, whereupon the spot plate detects the disappearance of compounds 2-4. Adding water and toluene, stirring, extracting the water layer with toluene twice, combining toluene layers, washing with water, performing silica gel column chromatography, spin-drying the solvent, and recrystallizing with toluene and ethanol for 3 times to obtain 13.5g of white solid, wherein GC is 98.3%.
Step 4
Into the reaction flask, 15.8g (0.038 mol) of Compound 2-5,5.2g (0.080 mmol) of 2-chloroethylamine, 11.0g (0.080 mmol) of potassium carbonate and 150mL of DMF were added, and the mixture was stirred with heating, and reacted at 100℃until the spot-size plate detects the disappearance of Compound 1-5. Adding water and toluene, stirring, extracting the water layer with toluene for two times, combining toluene layers, washing with water, performing silica gel column chromatography, spin-drying the solvent, and recrystallizing with toluene and petroleum ether for 3 times to obtain I1-1a, 11.5g of white solid, and LC:99.3%.
Example 3
The structural formula of the compound is shown as the following formula I1-2 a:
Step 1
Into a reaction flask were charged 10g (0.027 mol) of Compound 3-1, 5.0g (0.06 mol) of sodium hydrogencarbonate, 9.7g (0.03 mol) of tetrabutylammonium bromide, 6g (0.06 mol)100Mg of palladium acetate and 100mL of dimethylformamide are heated to 100deg.C and held for 6 hours. The mixture was cooled and then acidified with 100mL of dilute hydrochloric acid (1N). The aqueous layer was extracted twice with toluene, and the organic phases were combined, dried over anhydrous sodium sulfate, dried over spin-on solvent, and purified by distillation under reduced pressure to give 7.1g of a pale yellow oil, GC:96.5%.
Step 2
To the reaction flask was added 7.1g (0.018 mol) of compound 3-2,7mL of aqueous potassium hydroxide (2N), 100mL of ethanol. The reaction system was stirred and heated to reflux for 1 hour, and the spot plate detected disappearance of compound 4. The pH was adjusted to acidity with dilute hydrochloric acid (0.5N), the aqueous layer was extracted twice with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, the solvent was spun-dried, and recrystallized from ethanol to give 4.6g of off-white solid, LC:97.3%.
Step 3
4.6G (0.013 mol) of compound 3-3,4.7g (0.015 mol) of compound 3-4, 100ml of dichloromethane are added into a reaction bottle, stirring is carried out fully, 3.1g (0.015 mol) of DCC is added at room temperature, stirring is carried out at room temperature for 4 hours, and the disappearance of the compound 3-3 is detected by a dot plate; adding water, stirring, separating, extracting the water layer with dichloromethane twice, combining dichloromethane layers, washing with water, drying with anhydrous sodium sulfate, spin-drying the solvent, dissolving with toluene, performing silica gel column chromatography, and recrystallizing with toluene and ethanol for 2 times to obtain white solid 6.1g, and HPLC:98.1%.
Step 4
6.1G (0.009 mol) of compound 3-5 and 100mL of tetrahydrofuran were added to the reaction flask, followed by the addition of 2.3g (0.020 mol) of tetrabutylammonium fluoride in portions. The reaction was carried out at room temperature for 2 hours, and the spot plate was used to detect the disappearance of compounds 3-5. The aqueous layer was extracted twice with ethyl acetate, the organic layers were combined, washed with water, dried, spin-dried, and recrystallized 2 times from toluene petroleum ether to give 3.3g of off-white solid, LC:97.1%.
Step 5
Referring to step 3 in example 1, the target monomer I1-2a,1.5g, a white solid was obtained.
Example 4
The structural formula of the compound is shown as the following formula I8-3 a:
Step 1
Into a reaction flask were charged 6.8g (0.018 mol) of compound 4-1, 0.99g (0.009 mol)And 100mL of tetrahydrofuran, after which 2.3g (0.020 mol) of tetrabutylammonium fluoride were added in portions. The reaction was carried out at room temperature for 2 hours, and the spot plate was used to detect the disappearance of Compound 4-1. The aqueous layer was extracted twice with ethyl acetate, the organic layers were combined, washed with water, dried, spin-dried, and recrystallized 2 times from toluene petroleum ether to give 3.3g of off-white solid, LC:97.1%.
Step 2
Referring to step3 of example 1, the target monomer I8-3a was obtained as a white solid, 8g, LC:99.3%.
Manufacturing display case
Display cases were made with Norland 65 adhesive using 5 μm spacer beads through the original untreated alkali-free glass. The cartridge was assembled by hand and then cured using a high pressure mercury lamp having 50mW/cm 2 and 3000mJ/cm 2.
Box filling and curing
The LC mixture was capillary-filled using capillary action at room temperature, annealed at 100 ℃ for 1 hour and then irradiated with linearly polarized UV light (50 mW/cm 2) at the same temperature for 60 seconds. The box was then allowed to cool to room temperature.
Mother liquid crystal composition
TABLE 3 mother liquid crystal composition A-1
TABLE 4 mother liquid crystal composition A-2
TABLE 5 mother liquid crystal composition A-3
TABLE 6 mother liquid crystal compositions A-4
TABLE 7 mother liquid crystal compositions A-5
TABLE 8 mother liquid crystal compositions A-6
Liquid Crystal composition examples
From the above listed mother liquid crystal compositions A-1 to A-6 and the compounds of formula I, liquid crystal compositions B-1 to B-6 according to the invention were prepared according to the combinations given in the following tables.
Alignment experiment
Test displays were fabricated using raw untreated glass or ITO glass, then filled with nematic mixtures according to mixture examples B-1 to B-6, respectively, and then cured as described above.
The alignment quality was then studied between crossed polarizers on a light box. A good dark state is observed when the cell is placed between crossed polarizers. A good transmission state was observed when the cassette was rotated 45 °. This demonstrates the excellent uniform planar alignment achieved by the mixtures from examples B-1 to B-6. The liquid crystal box continuously applies voltage and switches the dark state and the bright state in the temperature environment of 78-80 ℃ for 500 hours, and the alignment exists stably. In the comparative experiments, the test displays were filled with nematic host mixtures A-1 to A-6 without compounds of the formula I and cured in the same manner as described for the mixture examples B-1 to B-6 according to the invention. In the comparative experiments, a non-uniform transmission state was observed under all polarizer configurations.
It should be understood that the foregoing examples of the present invention are provided merely for clearly illustrating the present invention and are not intended to limit the embodiments of the present invention, and that various other changes and modifications may be made therein by one skilled in the art without departing from the spirit and scope of the present invention as defined by the appended claims.
Claims (8)
1. A compound represented by the formula I1-1a,
2. A liquid crystal composition comprising the compound of claim 1.
3. The liquid crystal composition according to claim 2, further comprising one or more polymerizable compounds represented by formula P,
Pa-(Spa)s1-A2-(Z-A1)n2-(Spb)s2-Pb P
Wherein,
P a、Pb each independently represents a polymerizable group;
sp a、Spb each independently represents a spacer group;
s1, s2 are each independently 0 or 1;
Each a 1、A2 independently represents a group selected from the group consisting of:
a) A group consisting of trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene and 4,4' -dicyclohexylene, wherein one or more non-adjacent-CH 2 the groups are optionally replaced by-O-or-S-, one or more H atoms are optionally replaced by F atoms,
B) A group consisting of 1, 4-phenylene and 1, 3-phenylene, wherein one or two CH groups are optionally replaced by N, one or more H atoms are optionally replaced by L,
C) A group consisting of tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, tetrahydrofuran-2, 5-diyl, cyclobutane-1, 3-diyl, piperidine-1, 4-diyl, thiophene-2, 5-diyl and selenophene-2, 5-diyl, wherein one or more H atoms are optionally substituted by L,
D) From the following components
A group of which is composed of,
Wherein one or more H atoms in these groups are optionally replaced by L, and/or one or more double bonds are optionally replaced by single bonds, and/or one or more CH are optionally replaced by N;
n2 is 0, 1,2 or 3;
Z represents-CO-O-, -O-CO-, -CH 2O-、-OCH2-、-CF2O-、-OCF2 -, a linear alkylene group having 2 to 4 carbon atoms-O-, -CO-, -C (R 0R00)-、-CH2CF2-、-CF2CF2 -or a single bond;
L represents, independently for each occurrence, F atoms, cl atoms, CN, SCN, SF 5 or optionally fluorinated straight-chain or branched alkyl groups having 1 to 12C atoms, alkoxy groups, alkylcarbonyl groups, alkoxycarbonyl groups, alkylcarbonyloxy groups, alkoxycarbonyloxy groups;
r 0、R00 each independently of the other represents an H atom, an F atom or a linear or branched alkyl radical having 1 to 12C atoms, wherein one or more H atoms are optionally replaced by F atoms;
M represents-O-, -S-, -CH 2-、-CHY1 -or-CY 1Y2 -;
Y 1、Y2 each independently of the other represents an H atom, an F atom, a Cl atom, CN or a linear or branched alkyl radical having 1 to 12C atoms, wherein one or more H atoms are optionally replaced by F atoms.
4. The liquid crystal composition according to claim 2, wherein the liquid crystal composition further comprises one or more compounds represented by formula II and/or one or more compounds represented by formula III,
Wherein in the formula II,Representation
Representation
R 5、R6 each independently represents an alkyl group having 1 to 12 carbon atoms, wherein one or more non-adjacent-CH 2 -groups are optionally replaced by-O-, -ch=ch-, -CO-, -O-CO-, or-CO-O-;
Z 4 represents-CH 2CH2-、-CH＝CH-、-CF2O-、-OCF2-、-CH2 O-
OCH 2-、-COO-、-OCO-、-C2F4 -, -cf=cf-, or a single bond;
In the formula III, the compound of the formula III, Each independently represents
R 7、R8 is independently an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms.
5. The liquid crystal composition according to claim 2, wherein the liquid crystal composition further comprises one or more compounds of formula IV,
Wherein,
Each independently selected from the group consisting of the groups shown in ①、②:
① Trans 1, 4-cyclohexylene, 1, 4-cyclohexenylene in which one or more non-adjacent-CH 2 -groups are optionally substituted by-O-or-S-;
② 1, 4-phenylene, wherein one or two CH groups are optionally substituted with N and one or two H atoms are optionally substituted with F atoms;
R 9 represents A linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 10 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms;
X 1、X2 each independently represents an H atom or an F atom;
Y 3 represents an F atom, a linear alkyl group having 1 to 6 carbon atoms or a linear alkenyl group having 2 to 6 carbon atoms, wherein one or more hydrogen atoms are optionally replaced by an F atom;
z 5 represents a single bond, -CH 2-、-CH2CH2-、-(CH2)3-、-(CH2)4 -, -CH=CH-,
-C≡C-、-COO-、-OOC-、-OCH2-、-CH2O-、-CF2CH2-、-CH2CF2-、-C2F4- Or-cf=cf-;
r represents 0, 1 or 2.
6. The liquid crystal composition according to claim 4 or claim 5, wherein the liquid crystal composition further comprises one or more compounds of formula V,
Wherein R 10、R11 each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any one or more of R 10、R11 is not substituted with-CH 2 -optionally substituted with cyclopentylene, cyclobutylene or cyclopropylene;
Z 6、Z7 each independently represents a single bond, -CH 2CH2 -, or-CH 2 O-;
each independently represents/>
S represents 1 or 2; t represents 0, 1 or 2.
7. A liquid crystal display comprising the compound of claim 1, or the liquid crystal composition of any one of claims 2 to 6, the liquid crystal display being an active matrix display or a passive matrix display.
8. The liquid crystal display according to claim 7, wherein the display is an IPS display or an FFS display.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911120055.5A CN112812014B (en) | 2019-11-15 | 2019-11-15 | Compound, liquid crystal composition and liquid crystal display |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911120055.5A CN112812014B (en) | 2019-11-15 | 2019-11-15 | Compound, liquid crystal composition and liquid crystal display |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112812014A CN112812014A (en) | 2021-05-18 |
| CN112812014B true CN112812014B (en) | 2024-05-10 |
Family
ID=75851702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911120055.5A Active CN112812014B (en) | 2019-11-15 | 2019-11-15 | Compound, liquid crystal composition and liquid crystal display |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112812014B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4271673A1 (en) | 2020-12-30 | 2023-11-08 | Tyra Biosciences, Inc. | Indazole compounds as kinase inhibitors |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101792391A (en) * | 2009-01-23 | 2010-08-04 | Dic株式会社 | Polymerizable biphenyl compound |
| JP2011020981A (en) * | 2009-07-21 | 2011-02-03 | Dic Corp | Polymerizable compound and production intermediate for the compound |
| CN104508084A (en) * | 2012-08-08 | 2015-04-08 | 捷恩智株式会社 | Liquid crystal composition and liquid crystal display element |
| CN106242973A (en) * | 2015-06-09 | 2016-12-21 | 默克专利股份有限公司 | Polymerizable compound and purposes in a liquid crystal display thereof |
-
2019
- 2019-11-15 CN CN201911120055.5A patent/CN112812014B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101792391A (en) * | 2009-01-23 | 2010-08-04 | Dic株式会社 | Polymerizable biphenyl compound |
| JP2011020981A (en) * | 2009-07-21 | 2011-02-03 | Dic Corp | Polymerizable compound and production intermediate for the compound |
| CN104508084A (en) * | 2012-08-08 | 2015-04-08 | 捷恩智株式会社 | Liquid crystal composition and liquid crystal display element |
| CN106242973A (en) * | 2015-06-09 | 2016-12-21 | 默克专利股份有限公司 | Polymerizable compound and purposes in a liquid crystal display thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112812014A (en) | 2021-05-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI737834B (en) | Spontaneous alignment aid for liquid crystal composition | |
| JP5593890B2 (en) | Liquid crystal composition and liquid crystal device | |
| TWI671388B (en) | Liquid crystal composition and liquid crystal display device | |
| TWI719139B (en) | Liquid crystal composition and liquid crystal display element | |
| KR20190074987A (en) | Liquid crystal composition and liquid crystal display element | |
| KR101539703B1 (en) | Nematic liquid crystal composition | |
| KR101599756B1 (en) | Cinnamic acid derivative, polymer thereof, and liquid crystal alignment layer comprising hardened product of said polymer | |
| TW201736581A (en) | Liquid crystal mixture and liquid crystal display | |
| KR20200016215A (en) | Polymerizable monomer, liquid crystal composition and liquid crystal display element using the same | |
| CN107841316B (en) | Spontaneous alignment assistant for liquid crystal composition | |
| JP5839147B2 (en) | Compound, polymer, liquid crystal alignment film, liquid crystal display element, and optical anisotropic body | |
| KR20180090257A (en) | Liquid crystal composition and liquid crystal display element | |
| KR20130110172A (en) | Liquid crystal displays and liquid crystalline media with homeotropic alignment | |
| CN111465592B (en) | Compound, liquid crystal composition and liquid crystal display element | |
| JP5040400B2 (en) | Polymer stabilized liquid crystal composition and polymer stabilized liquid crystal display device | |
| TW201928030A (en) | Liquid crystal compositions and liquid crystal display element | |
| CN112004914A (en) | Liquid crystal mixture and liquid crystal display | |
| TW201732022A (en) | Method for manufacturing a liquid crystal display device and liquid crystal mixture | |
| TWI826484B (en) | Compounds, liquid crystal compositions, liquid crystal display elements and liquid crystal displays | |
| TW202028434A (en) | Liquid crystal mixture and liquid crystal display | |
| CN112812014B (en) | Compound, liquid crystal composition and liquid crystal display | |
| US11130911B2 (en) | Liquid crystal compound and liquid crystal composition | |
| CN112812012B (en) | Compound, liquid crystal composition, liquid crystal display element, and liquid crystal display | |
| CN110803990B (en) | Compound, liquid crystal composition, liquid crystal display element and liquid crystal display | |
| JP2015090427A (en) | Manufacturing method of liquid crystal alignment film and liquid crystal display element using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |