CN110803990B - Compound, liquid crystal composition, liquid crystal display element and liquid crystal display - Google Patents
Compound, liquid crystal composition, liquid crystal display element and liquid crystal display Download PDFInfo
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- CN110803990B CN110803990B CN201810880669.2A CN201810880669A CN110803990B CN 110803990 B CN110803990 B CN 110803990B CN 201810880669 A CN201810880669 A CN 201810880669A CN 110803990 B CN110803990 B CN 110803990B
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- liquid crystal
- carbon atoms
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- crystal composition
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 117
- 150000001875 compounds Chemical class 0.000 title claims abstract description 102
- 239000000203 mixture Substances 0.000 title claims abstract description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 89
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004976 cyclobutylene group Chemical group 0.000 claims description 8
- 125000004979 cyclopentylene group Chemical group 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 7
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 12
- 239000000178 monomer Substances 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 230000006750 UV protection Effects 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000004642 Polyimide Substances 0.000 abstract description 4
- 229920001721 polyimide Polymers 0.000 abstract description 4
- 238000012545 processing Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 230000037048 polymerization activity Effects 0.000 abstract description 3
- 238000000034 method Methods 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000010410 layer Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004873 anchoring Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 230000004224 protection Effects 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical group C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- -1 fluorine-substituted carbon atom Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RPJZSRHPVPELRE-UHFFFAOYSA-N 4-bromo-2,6-dihydroxybenzaldehyde Chemical compound C1=C(C=C(C(=C1O)C=O)O)Br RPJZSRHPVPELRE-UHFFFAOYSA-N 0.000 description 1
- HXTWKHXDFATMSP-UHFFFAOYSA-N 4-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC(Br)=CC=C1C=O HXTWKHXDFATMSP-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- LBJQKYPPYSCCBH-UHFFFAOYSA-N spiro[3.3]heptane Chemical compound C1CCC21CCC2 LBJQKYPPYSCCBH-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
-
- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- 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
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- 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
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/123—Ph-Ph-Ph
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- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- C09K19/00—Liquid crystal materials
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- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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Abstract
The invention relates to a compound, a liquid crystal composition, a liquid crystal display element and a liquid crystal display. The compound is shown in the following formula I. The liquid crystal composition of the invention contains a compound shown as a formula I. The compound shown in the formula I provided by the invention has the advantages of good intersolubility with other compounds, good ultraviolet resistance and the like. The Reactive Mesogen (RM) has the advantages of good intersolubility, high charge holding ratio (VHR), high polymerization activity (little monomer residue) and the like, can be independently used as a self-alignment agent of a liquid crystal composition, can be used as a vertical alignment material and other RM to be copolymerized with the self-alignment agent of a liquid crystal composition in a PSA (polymer supported alignment) mode and a PS (polymer stable) mode, can avoid PI (polyimide) processing, simplifies the processing of a liquid crystal display element or a liquid crystal display, and improves the production efficiency.
Description
Technical Field
The invention belongs to the technical field of liquid crystal display, and particularly relates to a compound, a liquid crystal composition containing the compound, and a liquid crystal display element or a liquid crystal display containing the liquid crystal composition.
Background
The liquid crystal medium used for the display element of the active matrix addressing system such as VA mode is not perfect, and for example, the residual image level is significantly inferior to that of the display element of positive dielectric anisotropy, the response time is relatively slow, and the driving voltage is relatively high. At this time, some new VA display technologies are silent and still in progress: the PSVA technology realizes a wide view angle display mode similar to MVA/PVA, and simplifies the CF process, so that the aperture opening ratio is improved while the CF cost is reduced, and higher brightness and higher contrast ratio can be obtained. In addition, since the whole liquid crystal has a pretilt angle and no domino delay phenomenon, a faster response time can be obtained under the same driving voltage, and the afterimage level is not affected, but since Fine Slit densely distributed electrodes in the pixel, if the electrode widths cannot be uniformly distributed, the problem of uneven display is easily caused. Like UVVA technology, on the basis of maintaining the advantages of PSVA technology, the problem of uneven display caused by uneven width of pixel electrodes is also improved due to the fact that a Slit structure is not arranged on the TFT side. Although display devices are continually being developed, efforts have been made to develop new liquid crystal compounds that allow the liquid crystal media and their application to display devices to continue to evolve.
The polymerizable mesogenic unit (RMs) is a very hot 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).
The PSA principle is being applied in different typical LC displays, such as PSA-VA, PSA-OCB, PS-IPS/FFS and PS-TN. Taking the PSA-VA display, which is currently the most widely used, as an example, the pretilt angle of the liquid crystal cell, which has a positive effect on the response time, can be obtained by the PSA method. For PSA-VA displays, standard MVA or PVA pixel and electrode designs can be used, but if the electrode design on one side is specially patterned and the other end is not raised, the production can be significantly simplified while the display is given very good contrast and high light transmittance.
The prior art has found that LC mixtures and RMs still have some drawbacks in application in PSA displays. For example, the panel process requires PI coating, which not only complicates the process and affects the throughput of the production line, but also causes the emission of organic pollutants.
Disclosure of Invention
The invention provides a compound capable of realizing self-alignment function, a liquid crystal composition containing the compound, a liquid crystal display element or a liquid crystal display containing the liquid crystal composition, and a PSVA liquid crystal composition especially suitable for display or TV application.
The compound has the advantages of good intersolubility with other compounds and good ultraviolet resistance. The Reactive Mesogen (RM) has the advantages of high charge holding ratio (VHR) and high polymerization activity (little monomer residue), can be independently used as a self-alignment agent of a liquid crystal composition, can be used as a self-alignment agent of a liquid crystal composition for copolymerization of a vertical alignment material and other RMs and used in PSA and PS modes, can avoid PI processes, and improves production efficiency.
The liquid crystal composition has lower viscosity, can realize quick response, and has moderate dielectric anisotropy delta epsilon, moderate optical anisotropy delta n and high stability to heat and light. The liquid crystal display element or the liquid crystal display containing the liquid crystal composition has the performances of wide nematic phase temperature range, proper or high birefringence anisotropy delta n, very high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like.
In order to achieve the above object, the present invention specifically provides the following compounds, which are compounds represented by the following formula I:
wherein R is 0 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 of them may be-CH 2 -optionally substituted with cycloalkylene; any one or more unconnected-CH(s) 2 -optionally being replaced by-O-;
the cycloalkylene group includes cyclopentylene group, cyclobutylene group and cyclopropyl group;
q represents 1, 2 or 3; r represents 0, 1, 2 or 3;
K 1 represents an aromatic, heteroaromatic, aliphatic or fused ring, in which any one of the rings is-CH 2 -optionally substituted with-O-, -S-; k (K) 1 One or more H on the ring are optionally covered by L 1 Substitution;
L、L 1 each independently represents-Sp 1 -P 4 、-Sp 2 -X 1 F, alkyl having 1 to 10 carbon atoms, fluoro-substituted alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, fluoro-substituted alkoxy having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, fluoro-substituted alkenyl having 2 to 10 carbon atoms, alkenyloxy having 3 to 8 carbon atoms or fluoro-substituted alkenyloxy having 3 to 8 carbon atoms, and any one of CH 2 Optionally substituted with cyclopentylene, cyclobutylene, and cyclopropyl ene;
P 4 represents a group which is H or a polymerizable group,
Sp 1 、Sp 2 each independently represents a single bond or a spacer;
X 1 represents a hydroxyl group, an ester group or a carbonyl group;
Z 0 represents a single bond, -O-, -S-, -CO-, -COO-, -OCO-, -OCOO-, -OCH 2 -、-CH 2 O-、-SCH 2 -、-CH 2 S-、-CF 2 O-、-OCF 2 -、-CF 2 S-、-SCF 2 -、-(CH 2 )n 1 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-(CF 2 )n 2 -、-CH＝CH-、-C≡C-、-CF＝CF-、-CH＝CH-COO-、-OCO-CH＝CH-、-(CR Y R Z )n 3 -、-CH(-Sp-P 5 )-、-CH 2 CH(-Sp-P 5 ) -, or-CH (-Sp-P) 5 )CH(-Sp-P 5 )-；
n 1 、n 2 、n 3 Each independently represents 1, 2, 3 or 4;
R Y 、R Z each independently represents H or an alkyl group having 1 to 5 carbon atoms, and at least one is an alkyl group having 1 to 5 carbon atoms;
sp represents a single bond or a spacer;
P 5 represents H or a polymerisable group;
R x represents (a), (b) or (c):
m 1 represents 1, 2, 3 or 4;
represents an aromatic ring, an aliphatic ring, and a condensed ring, wherein any one of the rings-CH 2 -optionally substituted with-O-, -S-;One or more H on the ring are optionally covered by L 2 Substitution;
Sp 3 、Sp 4 each independently represents a single bond or a spacer;
X 2 represents a hydroxyl group, an ester group or a carbonyl group;
L 2 representation-Sp 3 -X 2 F, alkyl having 1 to 10 carbon atoms, fluorine-substituted alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, fluorine-substituted C1 to 1 carbon atoms0, 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 of them-CH 2 Optionally substituted with cyclopentyl, cyclobutyl, cyclopropyl;
S 1 represents a trivalent radical, S 2 Represents a tetravalent group;
as trivalent groups, S may be mentioned 1 Representing the case of a trivalent radical of carbon or silicon; as tetravalent groups there may be mentioned S 2 Represents the case of tetravalent groups of phosphorus.
The compound shown in the formula I has better solubility in the liquid crystal composition, and the addition amount of the compound in the liquid crystal composition is generally between 0.5 and 5 percent, preferably between 1 and 2 percent, and is easy to absorb UV and quickly polymerize to form a polymer with an alignment function when the compound is in the range.
The compound shown in the formula I has an anchoring group X 1 、X 2 ，X 1 、X 2 Selected from hydroxyl, ester or carbonyl groups, preferably hydroxyl. After the liquid crystal composition is subjected to an ODF process, the compound shown in the formula I is spontaneously and vertically arranged on the surface of a panel (glass surface or ITO or polyimide), and is polymerized by UV illumination under the condition of voltage application to form a stable pretilt angle.
P 4 、P 5 When a polymerizable group is represented, a methacrylate group, an acrylate group, a vinyl group, or an ethylene oxide group is preferable.
The spacer represents a chain group, preferably a branched or straight chain alkyl group having 1 to 10 carbon atoms, and any non-bonded-CH in the alkyl group 2 -optionally replaced by-O-, optionally-CH 2 Optionally substituted with cyclopropylene, cyclobutylene or cyclopentylene.
K 1 Represents an aromatic, heteroaromatic, aliphatic or condensed ring, any of which-CH 2 -optionally substituted with-O-, -S-; k (K) 1 One or more H on the ring are optionally covered by L 1 And (3) substitution. The aromatic ring is preferably a benzene ring or a naphthalene ring, the heteroaromatic ring is preferably at least one-CH-N-substituted benzene ring or naphthalene ring, the aliphatic ring is preferably cyclohexane, cyclohexene,at least one-CH 2 -cyclohexane substituted by-O-or-S-and at least one-CH 2 -cyclohexene substituted by-O-or-S-, K 1 It may also represent spiro, bridged rings, preferably bicyclo (1, 1) pentane, bicyclo (2, 2) octane, bicyclo (3, 0) octane, spiro (3, 3) heptane, decalin, tetrahydronaphthalene, etc. Fused rings are preferably indane rings, indene rings, indane rings in which at least one C on the ring is replaced by-O-or-S-, and an indene ring in which at least one C on the ring is replaced by-O-or-S-.
Anchoring group X 1 preferably-OH.
R x Preferably:
alternatively, the compound of formula I is selected from the group consisting of compounds of formulas I1-I21 described below.
The invention also provides a liquid crystal composition which comprises one or more compounds shown in the formula I.
Optionally, the liquid crystal composition of the present invention may further comprise one or more compounds represented by formula II, and one or more compounds represented by formula III,
in formula II, R 1 、R 2 Each of which is a single pieceIndependently 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;
each independently represents->
In formula III, R 3 、R 4 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 R 3 、R 4 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene;
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -or-CH 2 O-；
Each independently represents
m represents 1 or 2; n represents 0, 1 or 2.
Optionally, the one or more compounds of formula II are selected from the group consisting of compounds of formulas II 1-II 14; one or more of the above compounds of formula III are selected from the group consisting of compounds of formulae III1 to III11,
in the formulae III1 to III11, R 3 、R 4 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 R 3 、R 4 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene.
In the liquid crystal composition, X in the compound shown in the formula I 1 、X 2 Represented by an anchoring functional group, X 1 、X 2 Each independently is an anchoring functional group with a hydroxyl group, a carbonyl group or an ester group structure, after the ODF process of the panel, the anchoring functional group and the intermolecular acting force of the panel surface (glass surface and ITO electrode surface) can be spontaneously and vertically arranged on the upper surface of the panel glass or ITO transparent electrode substrate to promote the vertical arrangement of liquid crystal molecules close to the compound shown in the formula I, and the compound shown in the formula I can be polymerized on the substrate to form a layer of polymer with rough surface under the irradiation of UV light, so that the functions of PI insulation and vertical alignment of the liquid crystal molecules are achieved. In general, the thickness of PI is 50nm to 120nm, and in order to form a film having a thickness equivalent to that of PI after polymerization of the compound of formula I, the addition amount of the compound of formula I is preferably 1% or lessAnd (3) upper part. In this case, the compound of formula I is added in a large amount, and thus there is a high demand for storage stability at low temperatures.
The compound shown in the formula I provided by the invention is used as a Reactive Mesogen (RM), and the cinnamic acid structure is used as a compound main body structure, and as the cinnamic acid structure has a polymerizable function, no or less polymerizable functional groups are required to be additionally added, the synthesis process is simple, the cost is low, and the molecular structure of the compound is simple. And, because cinnamic acid structure has the effect of lengthening the molecular length, compared with the prior RM, the method reduces one ring structure, so the synthetic route is simpler, the molecular weight is smaller, and the low-temperature storage property is better.
The compound shown in the formula I provided by the invention has the advantages of good intersolubility with other compounds, good ultraviolet resistance and the like. The Reactive Mesogen (RM) has the advantages of good intersolubility, high charge holding ratio (VHR), high polymerization activity (little monomer residue) and the like, can be independently used as a self-alignment agent of a liquid crystal composition, can be used as a self-alignment agent of a liquid crystal mixture of a vertical alignment material and RM copolymerized for PSA (polymer supported alignment) and PS (polymer stable) modes, can avoid PI (polyimide) processing, simplifies the processing of a liquid crystal display element or a liquid crystal display, and improves the production efficiency.
In addition, a liquid crystal composition comprising the compound shown in the formula I or an optically anisotropic body of the liquid crystal composition also belongs to the protection scope of the invention.
The compounds of formula I may have slightly different solubility properties in liquid crystals due to the different substituents, but may be added in an amount of 0.5% to 5% by mass in the liquid crystal composition. Since the polymer formed from the compound of formula I is required to have an insulating effect on PI, a certain thickness is necessary, and thus the compound of formula I is required to have sufficient solubility.
The compounds of the formula I may be added to the liquid crystal composition in an amount of 0.5% to 5%, preferably 1 to 3%, by mass.
The compound of formula II may be added to the liquid crystal composition in an amount of 15 to 60% by mass, preferably 20 to 40% by mass.
The compound of formula III may be added to the liquid crystal composition in an amount of 20 to 60% by mass, preferably 30 to 50% by mass.
Optionally, the liquid crystal composition of the invention can also contain one or more compounds shown in formula IV
Wherein R is 5 、R 6 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 R 5 、R 6 any-CH of 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene; w represents-O-, -S-or-CH 2 O-。
Optionally, the one or more compounds of formula IV are selected from compounds of formulas IV 1-IV 6:
wherein R is 61 Represents an alkyl group having 2 to 6 carbon atoms.
The compound of formula IV may be added to the liquid crystal composition in an amount of 1 to 15% by mass, preferably 2 to 10% by mass.
Optionally, the liquid crystal composition of the present invention may further comprise one or more compounds represented by formula V.
Wherein R is 7 、R 8 Each independently represents an alkyl group having 1 to 10 carbon atoms, and a fluorine-substituted carbon atom having 1 to 10 carbon atomsAn alkyl group, 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;
each independently represents 1, 4-phenylene, 1, 4-cyclohexylene or 1, 4-cyclohexenylene.
Optionally, the one or more compounds of formula v are selected from the group consisting of compounds of formulae v 1-v 4:
wherein R is 71 、R 81 Each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms; r is R 82 An alkoxy group having 1 to 5 carbon atoms; among them, the alkenyl group having 2 to 6 carbon atoms includes vinyl group, 2-propenyl group or 3-pentenyl group.
The compound of formula V may be added to the liquid crystal composition in an amount of 1 to 40% by mass, preferably 5 to 30% by mass.
Optionally, the liquid crystal composition of the present invention may further comprise one or more polymerizable compounds represented by formula VI,
each independently represents phenylene, fluorinated phenylene or indanyl;
P 1 、P 2 、P 3 each independently represents a methacrylate group or an acrylate group.
Optionally, the one or more compounds of formula VI are selected from the group consisting of compounds of formulas VI 1-VI 3:
the compounds of formula VI have a slightly lower UV sensitivity than the compounds of formula I, and have a slightly slower polymerization rate, and the compounds of formula VI are relatively superficial when actually forming the polymer. Under the condition that the compound shown in the formula VI is added to be copolymerized with the compound shown in the formula I, the display effect can be improved, the polymer layer provides continuous and stable pre-tilting, and the pre-tilting of liquid crystal molecules is very beneficial to improving the response speed of liquid crystal under an electric field. In the case of copolymerizing a compound represented by the formula VI with a compound represented by the formula I, the amount of the compound represented by the formula VI to be added may be 0.1 to 1% by mass, preferably 0.2 to 0.5% by mass.
The liquid crystal composition of the present invention exhibits slightly different properties such as dielectric anisotropy Δε, optical anisotropy Δn, transition temperature point CP of liquid crystal from nematic phase to liquid, and stability at low temperature, depending on the ratio of the components, but is characterized by the same rotational viscosity γ 1 Lower. The method is applied to the liquid crystal display device, and can realize quick response. The liquid crystal composition has high stability to heat and light. The liquid crystal display element or the liquid crystal display containing the liquid crystal composition has the performances of wide nematic phase temperature range, proper or high birefringence anisotropy delta n, very high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like. PSVA liquid crystal compositions suitable for display or TV applications have no or significantly reduced image sticking, especially after long running.
The liquid crystal compound provided by the invention can be further added with various functional dopants, the content of the dopants is preferably 0.01-1% by mass percent, and the dopants can be antioxidants, ultraviolet absorbers and chiral agents.
Antioxidants and ultraviolet absorbers may be mentioned:
s represents an integer of 1 to 10.
The invention also relates to a liquid crystal display element or a liquid crystal display comprising any one of the liquid crystal compositions; the display element or display is an active matrix display element or display or a passive matrix display element or display.
Alternatively, the liquid crystal display element or liquid crystal display is preferably an active matrix addressed liquid crystal display element or liquid crystal display.
Optionally, the active matrix display element or display is a PSVA-TFT liquid crystal display element or display without PI alignment layer.
Detailed Description
The invention will be further illustrated with reference to the following specific examples, but the invention is not limited to the following examples. The methods are conventional methods unless otherwise specified. The starting materials are commercially available from the public unless otherwise specified.
The progress of the reaction is generally monitored by TLC, and the post-treatment after the completion of the reaction is generally washing with water, extracting, combining the organic phases, drying, evaporating the solvent under reduced pressure, and recrystallizing, column chromatography, all of which can be carried out by those skilled in the art as described below.
The percentages in the specification are mass percentages, the temperature is in degrees centigrade (DEG C), 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 -n o ，n o Refractive index of ordinary ray, n e The refractive index of the extraordinary ray is 25+/-2 ℃ and is measured by an Abbe refractometer at 589 nm;
delta epsilon represents dielectric anisotropy, delta epsilon=epsilon ∥ -ε ⊥ Wherein ε is ∥ For dielectric constant parallel to the molecular axis ε ⊥ For the dielectric constant perpendicular to the molecular axis, the test conditions are 25+/-0.5 ℃ and 20-micrometer parallel boxes, INSTEC, ALCT-IR1 test;
γ1 represents rotational viscosity (mPas) under conditions of 25.+ -. 0.5 ℃ and 20 μm parallel box, INSTEC: ALCT-IR1 test;
the preparation method of the liquid crystal composition comprises the following steps: and weighing all the liquid crystal monomers according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker with all the liquid crystal monomers on a magnetic stirring instrument, heating and melting, adding a magnetic rotor into the stainless steel beaker after most of the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The liquid crystal monomer structure of the embodiment of the invention is represented by codes, and the code representation method of the liquid crystal ring structure, the end group and the connecting group is shown in the table I and the table II below
Table (one): corresponding code of ring structure
Table (ii): corresponding codes of end groups and linking groups
Examples:
the compounds of formula I may be prepared by the following schematic synthetic route:
when L is a polymerizable group:
for the product obtained by the above-described schematic synthetic route, the reaction product was precipitated as a solid by adding ice water, and the obtained product was determined by HPLC.
Example 1
Step 1
50g (0.194 mol) of compound A, 37g (0.23 mol 0) of diethyl malonate, 500ml of acetonitrile and 15.5g (0.194 mol) of pyridine are added, nitrogen protection and heating reflux reaction are carried out for 8 hours, after the reaction is finished, the system is poured into ice water, 1L of ethyl acetate is used for extraction and concentration to obtain oily matter, the oily matter is added into a system of 100ml of hydrochloric acid and 200ml of water, the temperature is increased for 5 hours, after the reaction is finished, the system is poured into the ice water, solid is separated out, and suction filtration is carried out to obtain white solid 1-a, 48g is added, the yield is 82.7%, and the purity of the white solid is 99.2% according to HPLC detection.
Step 2
30g (0.1 mol) of Compound 1-a, 10.6g (0.1 mol) of Compound B are added to 200ml of dichloromethane, under nitrogen, the temperature is brought to 0℃and 0.1g (0.01 mol) of DMAP is added, and then 24.7g (0.12 mol) of DCC are added in portions. Stirring at room temperature for 3 hours, pouring the system into water after the reaction is finished, extracting with dichloromethane, drying and spin-drying. Compound 1-b was obtained in a total of 32g in 84.2% yield by HPLC:98.5%.
Step 3
32g (0.08 mol) of compound 1-b was added to 200ml of tetrahydrofuran solution, the temperature was lowered to 0-10℃and 50ml of 10% aq. HCl was added dropwise thereto, followed by stirring at room temperature for 30 minutes after the completion of the addition. After the reaction, the reaction mixture was poured into water, extracted with ethyl acetate, dried and separated from the column to obtain a white solid (15 g, yield 53%) and HPLC (99.1%).
Example 2
Step 1
30g (0.12 mol) of compound C, 23.3g (0.12 mol) of 2-hydroxy-4-bromobenzaldehyde, 25g (0.18 mol) of potassium carbonate and the like are added into toluene/water/ethanol (300/50/50 v) for nitrogen protection, 0.2g of catalyst is added, and the mixture is heated to 80 ℃ for reaction for 3 hours. After the reaction, the system was poured into water, extracted with ethyl acetate, dried over sodium sulfate, dried by spin-drying, and recrystallized from ethanol. A white solid 2-a was obtained, total 33g, yield 85%. GC 98.2%.
Step 2
Compound 2-b was synthesized from compound 2-a according to the procedure of step 1 in example 1 to give 25g of a white solid in a yield of 67.5% and HPLC:98.6%.
Step 3
25g (0.066 mol) of compound 2-b was added to DCM, cooled to 0℃and 13.4g (0.13 mol) of triethylamine was added thereto, followed by dropwise addition of 6.5g (0.073 mol) of acryloyl chloride. Stirring at room temperature for 2 hours, washing the system with 1L of water for 2 times, drying with anhydrous sodium sulfate, and spin-drying. 22g of white solid was obtained in 77.7% yield by HPLC 95.3%.
Step 4
22g (0.05 mol) of compound 2-c, 9g (0.056 mol) of compound D, 0.68g (0.006 mol) of DMAP are added to 200ml of DCM, the temperature is reduced to 0℃and 12.36g (0.06 mol) of DCC are added in portions under nitrogen protection, the reaction is allowed to proceed overnight, and the system is washed with 500ml of X2 brine for 2 times. The organic phase was dried by spinning and recrystallized from 2 by ethanol. Suction filtered to white solid 18g, yield: 61.4% and 98.6% GC.
Step 5
Compound 2-d 18g (0.031 mol) was added to 100ml of acetonitrile at a temperature of 0℃and 0.6g (0.003 mol) of p-toluenesulfonic acid was added. Stirring at room temperature for 4 hours, adding the system into water, extracting with ethyl acetate 500ml X2 for 2 times, washing an organic phase with saturated saline water for 2 times, drying with anhydrous sodium sulfate, spin-drying the organic phase, and recrystallizing with toluene with 2 times ethanol and 1 time. Suction filtration gave 10g of a white solid in 59.8% yield by HPLC 99.5%.
Example 3
Step 1
Compound 3-a,25g, 86% yield, 98.02% by HPLC were synthesized by following the procedure of step 1 in example 2 starting from compound C and 2, 6-dihydroxy4-bromobenzaldehyde.
Step 2
Compound 3-b,25g, 88% yield, HPLC:97.52% was synthesized by the procedure of step 2 in example 2 starting from compound 3-a.
Step 3
Compound 3-c,20.2g, yield 80%, HPLC:98.4% was synthesized by following the procedure of step 3 in example 2 starting from compound 3-b.
Step 4
Compound 3-d,18g, yield 85% and HPLC 99.1% were synthesized by following the procedure of step 4 in example 2 starting from compound 3-c.
Step 5
Compound 3-e,10g, 90% yield, 99.7% HPLC were synthesized by following the procedure of step 5 in example 2 starting from compound 3-d.
Example 4: the liquid crystal composition comprises the following components in percentage by mass.
Example 5: the liquid crystal composition comprises the following components in percentage by mass.
Example 6: the liquid crystal composition comprises the following components in percentage by mass.
Example 7: the liquid crystal composition comprises the following components in percentage by mass.
Comparative example 1
Replacement of I21 from example 7 with an existing reactive mesogen (A) having a dihydroxyl structure
The liquid crystal composition of example 7 was poured into a test cell (no polyimide alignment layer, cell thickness 4 μm, ITO electrode on the substrate surface, no passivation layer), a voltage of 15V was applied to both sides of the test cell, and UV was appliedDominant wavelength 313 nm) 200s,0.55mw/cm 2 The voltage was then removed at 0.20mw/cm 2 The compound shown in the formula I and the compound shown in the formula VI are completely polymerized after being irradiated for 100min under the light intensity, so that a stable pre-inclined polymerization layer is formed. After the power-up and UV light irradiation treatment, the liquid crystal molecules in the test box are spontaneously vertically aligned, and the vertical alignment of the liquid crystal molecules can be kept stable in an environment of 0-80 ℃.
The test box is tested for 1000 hours under the temperature environment of 78-80 ℃ by continuously applying voltage and switching the dark state and the bright state, and the pretilt of the polymeric layer still exists stably.
Comparative example 7 and comparative example 1 the liquid crystal composition according to example 7 of the present invention provides a compound of formula I having better low temperature solubility.
In conclusion, the compound shown in the formula I can play a role in PI insulation after polymerization, vertical alignment can be realized, polymerization can be realized under the condition of voltage application, and the polymer layer can provide continuous and stable pre-tilt after the voltage is removed, so that liquid crystal molecules have stable pre-tilt, and the pre-tilt of the liquid crystal molecules is very beneficial to improving the response speed of the liquid crystal under an electric field.
Claims (7)
1. A compound selected from the group consisting of compounds of formula I21,
2. a liquid crystal composition comprising a compound of formula I21 according to claim 1.
3. The liquid crystal composition according to claim 2, further comprising one or more of the compounds of the following formulas II1, II 4 and II 13, and one or more of the compounds of the formulas III1, III 2 and III 7, and further comprising one of the compounds of the formula VI 1,
in the formulae III1, III 2 and III 7, R 3 Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and R 3 Any one or more of the unconnected-CH' s 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene; r is R 4 An alkoxy group having 1 to 10 carbon atoms;
in the liquid crystal composition, the mass percentage of the compound shown in the formula I21 is 1-3%; the mass percentage of the compound shown in the formula VI 1 is 0.2-0.5%.
4. The liquid crystal composition according to claim 3, wherein the liquid crystal composition is a negative dielectric anisotropic liquid crystal composition, and the liquid crystal composition further comprises one or more compounds represented by formula IV
Wherein R is 5 、R 6 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 R 5 、R 6 Any one or more of-CH 2 Optionally substituted with cyclopentylene, cyclobutylene or cyclopropyl ene; w represents-O-, -S-or-CH 2 O-。
5. The liquid crystal composition according to claim 3, wherein the liquid crystal composition is a negative dielectric anisotropic liquid crystal composition, the liquid crystal composition further comprising one or more compounds of formula V,
wherein R is 7 、R 8 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;
each independently represents 1, 4-phenylene, 1, 4-cyclohexylene or 1, 4-cyclohexenylene.
6. A liquid crystal display element or a liquid crystal display comprising the compound of claim 1 or the liquid crystal composition of any one of claims 2 to 5; the display element or display is an active matrix display element or display or a passive matrix display element or display.
7. The liquid crystal display element or the liquid crystal display according to claim 6, wherein: the active matrix display element or display is a PSVA-TFT liquid crystal display element or display without a PI alignment layer.
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| CN112480938B (en) * | 2020-12-15 | 2022-09-27 | 烟台显华化工科技有限公司 | Negative dielectric anisotropy liquid crystal composition and liquid crystal display device |
| CN117024657B (en) * | 2023-09-28 | 2023-12-29 | 北京灵犀微光科技有限公司 | Holographic polymer dispersed liquid crystal material and application thereof |
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