CN113717735B - Positive dielectric anisotropic liquid crystal compound, liquid crystal composition and liquid crystal display device - Google Patents
Positive dielectric anisotropic liquid crystal compound, liquid crystal composition and liquid crystal display device Download PDFInfo
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- CN113717735B CN113717735B CN202110922470.3A CN202110922470A CN113717735B CN 113717735 B CN113717735 B CN 113717735B CN 202110922470 A CN202110922470 A CN 202110922470A CN 113717735 B CN113717735 B CN 113717735B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 169
- 150000001875 compounds Chemical class 0.000 title claims abstract description 163
- 239000000203 mixture Substances 0.000 title claims abstract description 99
- 125000004432 carbon atom Chemical group C* 0.000 claims description 98
- -1 2, 6-dioxan-1, 4-diyl Chemical group 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 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 8
- 239000011159 matrix material Substances 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 125000005450 2,3-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C(F)=C(F)C([*:1])=C1[H] 0.000 claims description 2
- 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 claims description 2
- 230000004044 response Effects 0.000 abstract description 13
- 230000003287 optical effect Effects 0.000 abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 5
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 5
- 125000006023 1-pentenyl group Chemical group 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 206010047571 Visual impairment Diseases 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 3
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 3
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Natural products CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- XRMZKCQCINEBEI-UHFFFAOYSA-N 4-bromo-2-fluoro-1-iodobenzene Chemical compound FC1=CC(Br)=CC=C1I XRMZKCQCINEBEI-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- HYDVVGSQURFARM-UHFFFAOYSA-N iodomethane;phosphane Chemical compound P.IC HYDVVGSQURFARM-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- CLGIPVVEERQWSQ-UHFFFAOYSA-N (2,3,4-trifluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C(F)=C1F CLGIPVVEERQWSQ-UHFFFAOYSA-N 0.000 description 1
- UHDDEIOYXFXNNJ-UHFFFAOYSA-N (3,4,5-trifluorophenyl)boronic acid Chemical compound OB(O)C1=CC(F)=C(F)C(F)=C1 UHDDEIOYXFXNNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- NFYCPIJWXRRVLR-UHFFFAOYSA-N ethane-1,2-diol;propanal Chemical compound CCC=O.OCCO NFYCPIJWXRRVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
-
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Abstract
The present invention relates to a positive dielectric anisotropic liquid crystal compound, a liquid crystal composition and a liquid crystal display device. The liquid crystal compound of the invention is a liquid crystal compound shown in the following formula I, which can maintain proper optical anisotropy value, dielectric anisotropy and K 33 /K 11 Obtaining reduced G on the basis of the value 1 /K 11 And thus can reduce the response time, which is advantageous in achieving a quick response.
Description
Technical Field
The invention relates to the technical field of liquid crystal display materials. And more particularly, to a positive dielectric anisotropic liquid crystal composition and a liquid crystal display device.
Background
At present, the application range of the liquid crystal compound is expanded more and more, and the liquid crystal compound can be applied to various types of displays, such as televisions, mobile phones, industrial control displays, vehicle-mounted displays and the like, electro-optical devices, sensors and the like. The liquid crystal compounds used in the above display fields are various, and among them, nematic liquid crystals are most widely used. Nematic liquid crystals have been used in passive TN, STN matrix displays and systems with TFT active matrices.
For the application field of thin film transistor technology (TFT-LCD), although the market has been very huge in recent years, the technology is gradually mature, but the requirements of people on display technology are continuously increasing, especially in the aspects of realizing fast response, reducing driving voltage to reduce power consumption, and the like. The liquid crystal material is one of important photoelectronic materials for liquid crystal display and has important effect in improving the performance of liquid crystal display.
For the liquid crystal composition, how to maintain proper optical anisotropy value, dielectric anisotropy and K 33 /K 11 Obtaining reduced response times on a value basis is a problem to be solved in the art.
Disclosure of Invention
In one aspect, the present invention provides a novel positive dielectric anisotropic liquid crystal compound capable of maintaining a proper optical anisotropy value, dielectric anisotropy, K by using the liquid crystal compound of the present invention in a liquid crystal composition 33 /K 11 Obtaining reduced G on the basis of the value 1 /K 11 Values of the optical anisotropy, dielectric anisotropy and K are maintained at appropriate values 33 /K 11 A fast response is obtained on the basis of the values.
In another aspect, the present invention provides a liquid crystal composition which can maintain an appropriate optical anisotropy value, dielectric anisotropy, K by containing the liquid crystal compound of the present invention 33 /K 11 A fast response is obtained on the basis of the values. Further, the liquid crystal composition also has an improved VHR value, so that defects such as afterimages of a final display can be overcome or reduced.
Another aspect of the present invention provides a liquid crystal display device which has a fast response time by containing the liquid crystal compound of the present invention. Further, the liquid crystal display device of the present invention has reduced defects such as afterimage due to the use of the liquid crystal composition having a high VHR value, and thus can obtain display advantages of reduced power consumption and improved stability.
The invention comprises the following technical scheme.
In one aspect, the present invention provides a novel positive dielectric anisotropic liquid crystal compound which is a liquid crystal compound represented by the following formula I:
wherein R is 1 Represents H, an alkyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, wherein optionally 4 or less H are substituted with F;
R 2 represents H, F, alkyl having 1 to 8 carbon atoms or alkenyl having 2 to 8 carbon atoms, wherein one or two of them are not adjacent to each other, -CH 2 -optionally substituted with-O-, optionally less than 4H are substituted with F;
m is 1 or 2;
n is selected from 1, 2, 3 or 4;
o is 1 or 2;
Z 1 representation-C 2 H 4 -、-CH 2 O-、-S-、-CF 2 O-or-COO-wherein-C 2 H 4 -wherein optionally 0 to 4H are substituted by F;
Z 2 Represents a single bond, -CF 2 O-or-COO-;
ring a, ring B, ring C each independently represent a group selected from the group consisting of: 1, 4-cyclohexylene, 1-methyl-1, 4-cyclohexylene, 2-oxetan-1, 4-diyl, 2, 6-dioxan-1, 4-diyl, cyclohexene-1, 4-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 2-fluoro-3-trifluoromethyl-1, 4-phenylene, 2, 3-bis (trifluoromethyl) -1, 4-phenylene, 2-fluoro-3-trifluoromethoxy-1, 4-phenylene, 2, 3-bis (trifluoromethoxy) -1, 4-phenylene, 2, 6-difluoro-substituted-1, 4-phenylene 2, 5-difluoro-substituted-1, 4-phenylene, 2-fluoro-6-trifluoromethyl-1, 4-phenylene, 2-fluoro-5-trifluoromethyl-1, 4-phenylene, 2-fluoro-6-trifluoromethoxy-1, 4-phenylene, 2-fluoro-5-trifluoromethoxy-1, 4-phenylene, 2, 6-bis (trifluoromethyl) -1, 4-phenylene, 2, 5-bis (trifluoromethyl) -1, 4-phenylene, 2, 6-bis (trifluoromethoxy) -1, 4-phenylene, 2, 5-bis (trifluoromethoxy) -1, 4-phenylene, 2-trifluoromethyl-6-trifluoromethoxy-1, 4-phenylene, 2-trifluoromethyl-5-trifluoromethoxy-1, 4-phenylene.
In another aspect, the present invention provides a liquid crystal composition comprising the liquid crystal compound of the present invention described above.
In still another aspect, the present invention provides a liquid crystal display device comprising the aforementioned liquid crystal compound of the present invention, or the aforementioned liquid crystal composition of the present invention; the liquid crystal display device is an active matrix display device, or a passive matrix display device.
Effects of the invention
The invention has the advantages that compared with the prior art, the liquid crystal composition can maintain proper optical anisotropy value, dielectric anisotropy and K by adopting the positive dielectric anisotropy liquid crystal compound 33 /K 11 Obtaining reduced G on the basis of the value 1 /K 11 Value, thereby obtaining a fast response. In addition, by including the aforementioned liquid crystal compound of the present invention in the liquid crystal composition of the present invention, the VHR after irradiation with UV light is high, and thus defects such as afterimages occurring in the final display device can be overcome/reduced.
Drawings
FIG. 1 is a mass spectrum of the compound CVEPGU-V-F prepared in example 1 of the present invention.
FIG. 2 is a mass spectrum of the compound CVEPUQU-V-F prepared in example 2 of the present invention.
Detailed Description
[ liquid Crystal Compound ]
The novel positive dielectric anisotropic liquid crystal compound of the present invention is a liquid crystal compound represented by the following formula I:
Wherein R is 1 Represents H, an alkyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, wherein optionally 4 or less H are substituted with F;
R 2 represents H, F, alkyl having 1 to 8 carbon atoms or alkenyl having 2 to 8 carbon atoms, wherein one or two of them are not adjacent to each other, -CH 2 -optionally substituted with-O-, optionally less than 4H are substituted with F;
m is 1 or 2;
n is selected from 1, 2,3 or 4;
o is 1 or 2;
Z 1 representation-C 2 H 4 -、-CH 2 O-、-S-、-CF 2 O-or-COO-wherein-C 2 H 4 -wherein optionally 0 to 4H are substituted by F;
Z 2 represents a single bond, -CF 2 O-or-COO-;
ring a, ring B, ring C each independently represent a group selected from the group consisting of: 1, 4-cyclohexylene, 1-methyl-1, 4-cyclohexylene, 2-oxetan-1, 4-diyl, 2, 6-dioxan-1, 4-diyl, cyclohexene-1, 4-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 2-fluoro-3-trifluoromethyl-1, 4-phenylene, 2, 3-bis (trifluoromethyl) -1, 4-phenylene, 2-fluoro-3-trifluoromethoxy-1, 4-phenylene, 2, 3-bis (trifluoromethoxy) -1, 4-phenylene, 2, 6-difluoro-substituted-1, 4-phenylene 2, 5-difluoro-substituted-1, 4-phenylene, 2-fluoro-6-trifluoromethyl-1, 4-phenylene, 2-fluoro-5-trifluoromethyl-1, 4-phenylene, 2-fluoro-6-trifluoromethoxy-1, 4-phenylene, 2-fluoro-5-trifluoromethoxy-1, 4-phenylene, 2, 6-bis (trifluoromethyl) -1, 4-phenylene, 2, 5-bis (trifluoromethyl) -1, 4-phenylene, 2, 6-bis (trifluoromethoxy) -1, 4-phenylene, 2, 5-bis (trifluoromethoxy) -1, 4-phenylene, 2-trifluoromethyl-6-trifluoromethoxy-1, 4-phenylene, 2-trifluoromethyl-5-trifluoromethoxy-1, 4-phenylene.
The aforementioned 2-fluoro-1, 4-phenylene group represents 2 divalent groups in which the fluorine substituent may be located on the left side or on the right side.
2-methyl-1, 4-cyclohexylene represents the following 2 divalent groups:
other similar groups also apply this rule.
As the aforementioned R 1 The "alkyl group having 1 to 8 carbon atoms" may be a straight-chain alkyl group, a branched alkyl group or a cyclic alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a cyclopentyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclobutyl group, an n-pentyl group, an isopentyl group, a cyclopentyl group, a hexyl group, a heptyl group, an octyl group and the like.
As the aforementioned R 1 The "alkenyl group having 2 to 8 carbon atoms" may be a straight-chain alkenyl group, a branched alkenyl group or an alkenyl group having a cyclic alkyl chain, and is not particularly limited. Examples thereof include ethenyl, propenyl, butenyl, 2-methylpropenyl, 1-pentenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 2-methyl-2-butenyl, pentenyl, hexenyl, heptenyl and the like.
In the aforementioned "alkyl group having 1 to 8 carbon atoms" and "alkenyl group having 2 to 8 carbon atoms", optionally, 4 or less of H's are substituted with F, for example, optionally 0, 1, 2, 3 or 4H's are substituted with F. For example, R 1 In the case where the methyl group represented is substituted with F, it may be, for example, -CH 2 F、-CHF 2 or-CF 3 . The other groups substituted with F are similar to those described above, and detailed description thereof will be omitted.
As the aforementioned R 2 The "alkyl group having 1 to 8 carbon atoms" may be a straight-chain alkyl group, a branched alkyl group or a cyclic alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a cyclopentyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclobutyl group and an n-pentyl groupRadical, isopentyl, cyclopentyl, hexyl, heptyl, octyl, and the like.
As the aforementioned R 2 The "alkenyl group having 2 to 8 carbon atoms" may be a straight-chain alkenyl group, a branched alkenyl group or an alkenyl group having a cyclic alkyl chain, and is not particularly limited. Examples thereof include ethenyl, propenyl, butenyl, 2-methylpropenyl, 1-pentenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 2-methyl-2-butenyl, pentenyl, hexenyl, heptenyl and the like.
R as described above 2 Of the groups represented by "alkyl group having 1 to 8 carbon atoms" and "alkenyl group having 2 to 8 carbon atoms", one or two non-adjacent-CH 2 -optionally substituted with-O-. For example, R 2 represents-CH 2 CH 3 In the case of (C), wherein-CH 2 The radical obtained after substitution by O is-OCH 3 ，R 2 represents-CH 2 CH 2 CH 3 In the case of one of them-CH 2 The radical obtained after substitution by O is-OCH 2 CH 3 And so on, are not listed here.
R as described above 2 The expression "alkyl group having 1 to 8 carbon atoms", "alkenyl group having 2 to 8 carbon atoms" and one or two non-adjacent-CH 2 -optionally-O-, further optionally less than 4H groups substituted with F. For example, R 2 represents-CH 3 In the case of (2), 1 to 3H groups obtained by F substitution are each-CH 2 F、-CHF 2 、-CF 3 ,R 2 Representation of-OCH 3 In the case of (2), 1 to 3H groups obtained by F substitution are each-OCH 2 F、-OCHF 2 、-OCF 3 。
Preferably, R 2 Represent H, F, -CH 2 F、-CHF 2 、-CF 3 、-OCH 2 F、-OCHF 2 or-OCF 3 . More preferably F, -OCH 2 F. or-OCF 3 。
The positive dielectric anisotropic liquid crystal compound of the present invention is represented by the above formula IThereby being capable of maintaining proper optical anisotropy value, dielectric anisotropy and K 33 /K 11 Obtaining reduced G on the basis of the value 1 /K 11 A value such that a rapid response is obtained, whereby the response time can be reduced when used in a liquid crystal composition, which is advantageous in achieving a rapid response.
Preferably, the liquid crystal compound represented by the above formula I is selected from the group consisting of compounds represented by the following formulas I-1 to I-36:
Wherein R is 1 、R 2 Is as defined above.
[ Synthesis of liquid Crystal Compound having positive dielectric anisotropy ]
The method for synthesizing the positive dielectric anisotropic liquid crystal compound of the present invention will be described below.
The compounds of formula I can be synthesized by combining methods of organic synthetic chemistry. For example, with-CH=CH-CH 2 -CH 2 In the case of compounds of the structure, -ch=ch-CH 2 -CH 2 The structure can be synthesized as follows:
with at least oneThe organic bromide (a 1) having a ring structure is reacted with p-bromophenylpropionaldehyde ethylene glycol to give the aforementioned compound (a 2) having a ring structure linked to propionaldehyde ethylene glycol. The compound (a 2) is hydrolyzed with formic acid, and the propionaldehyde acetal of the compound (a 2) is hydrolyzed to generate a compound (a 3) with a ring structure connected with propionaldehyde. The aforementioned compound (a 3) is further reacted with a methyl iodide phosphine salt (e.g., 4-vinylcyclohexylmethyl iodide phosphine salt) in a system containing potassium tert-butoxide, THF to give a compound having-CH=CH-CH 2 -CH 2 -a compound of structure (a 4). The reaction scheme is shown in the following reaction scheme 1.
The 4-vinylcyclohexyliodomethane phosphine salt may be replaced with other iodomethane phosphine salts as required to obtain-ch=ch-CH 2 -CH 2 -compounds linked to different structures.
Scheme 1 of the reaction
(2) Synthesis example 1
The synthetic route of the aforementioned compound represented by formula A-6 is shown in the aforementioned synthetic route pattern. Concretely, trifluoro-phenylboronic acid and 2-fluoro-4-bromoiodobenzene react under the condition of stirring, heating and refluxing in a reaction system containing tetrahydrofuran, sodium carbonate and tetra (triphenylphosphine) palladium to generate a compound shown in a formula A-1. Then, the compound represented by the formula A-1 was reacted with triisopropyl borate in anhydrous tetrahydrofuran in the presence of butyllithium n-hexane and THF to give the compound represented by the formula A-2. Then, the compound shown in the formula A-2 reacts with ethylene glycol p-bromophenylpropionaldehyde under the action of a catalyst of bis (di-tert-butyl-4-dimethylaminophosphine) palladium chloride to generate the compound shown in the formula A-3. The compound shown in the formula A-3 is hydrolyzed in a system containing formic acid to obtain the compound shown in the formula A-4. The compound shown in the formula A-4 is further reacted with 4-ethylene cyclohexyl methyl iodide phosphine salt in a system containing potassium tert-butoxide and THF to obtain the compound shown in the formula A-5. Then, the compound represented by the formula A-5 was heated in a system containing toluene, sodium benzene sulfinate and concentrated hydrochloric acid to reverse the configuration, thereby obtaining a compound represented by the formula A-6.
(2) Synthesis example 2
Preparation of CVEPUQU-V-F
The synthetic route of the aforementioned compound represented by formula B-6 is shown in the aforementioned synthetic route pattern.
Specifically, the compound shown in the formula B-1 is reacted with triisopropyl borate in the presence of anhydrous tetrahydrofuran and butyllithium n-hexane to obtain the compound shown in the formula B-2, and then the compound shown in the formula B-2 is reacted with ethylene p-bromophenylpropionaldehyde in the presence of a catalyst bis (di-tert-butyl-4-dimethylaminophosphine) palladium chloride to obtain the compound shown in the formula B-3. The compound represented by the formula B-3 is hydrolyzed in the presence of formic acid to obtain a compound represented by the formula B-4. The compound shown in the formula B-4 is reacted with 4-vinylcyclohexyliodomethane phosphine salt in the presence of potassium tert-butoxide and THF to obtain the compound shown in the formula B-5 containing E, Z configuration. Then, the compound represented by the formula B-5 was heated in a system containing toluene, sodium benzene sulfinate and concentrated hydrochloric acid to reverse the configuration, thereby obtaining a compound represented by the formula B-6.
For the synthesis of other structures of the liquid crystal compounds of the present invention, those skilled in the art can select appropriate synthetic routes and conditions as needed for the preparation.
[ liquid Crystal composition ]
The liquid crystal composition of the present invention contains the liquid crystal compound represented by the formula I.
The liquid crystal composition of the present invention may contain 1 or 2 or more liquid crystal compounds represented by formula I. The liquid crystal composition of the present invention may contain only the liquid crystal compound represented by formula I as a liquid crystal compound component. The composition of the present invention may contain the compound represented by formula I in a range of, for example, 1 to 99 mass%.
The liquid crystal composition of the present invention is a liquid crystal composition having positive dielectric anisotropy.
By using the liquid crystal compound of the present invention represented by the formula I in the liquid crystal composition of the present invention, it is possible to maintain an appropriate optical anisotropy value, dielectric anisotropy, K 33 /K 11 Obtaining reduced G on the basis of the value 1 /K 11 Value, thereby obtaining a fast response. Further, the liquid crystal composition of the present invention has an improved VHR value, so that defects such as afterimages of a liquid crystal display device can be reduced/eliminated.
In addition to the liquid crystal compounds represented by the above formula I, the liquid crystal composition of the present invention may contain other liquid crystal compounds. The other liquid crystalline compound that may be contained may have positive dielectric anisotropy or negative dielectric anisotropy.
In some embodiments of the liquid crystal composition of the present invention, it preferably further comprises:
at least one compound of formula II;
at least one compound of formula III: the method comprises the steps of,
at least one compound of formula IV:
wherein,,
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 5 carbon atoms;
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 each H on any carbon atom is independently optionally substituted with F, one or two non-adjacent-CH 2 -optionally substituted with-O-;
Z 3 represents a single bond or-CH 2 O-；
Z 4 representation-C 2 H 4 -、-CH 2 O-、-S-、-CF 2 O-or-COO-wherein-C 2 H 4 -wherein optionally 0 to 4H are substituted by F;
s is selected from 1, 2,3 or 4;
p represents 0, 1, 2 or 3;
q, r, v each independently represent 0, 1 or 2;
ring A1, ring A2, ring A3, ring A4, ring A5, ring A6 each independently represent a group selected from the group consisting of: 1, 4-cyclohexylene, 1-methyl-1, 4-cyclohexylene, 2-oxetan-1, 4-diyl, 2, 6-dioxan-1, 4-diyl, cyclohexene-1, 4-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 2-fluoro-3-trifluoromethyl-1, 4-phenylene, 2, 3-bis (trifluoromethyl) -1, 4-phenylene, 2-fluoro-3-trifluoromethoxy-1, 4-phenylene, 2, 3-bis (trifluoromethoxy) -1, 4-phenylene, 2, 6-difluoro-substituted-1, 4-phenylene 2, 5-difluoro-substituted-1, 4-phenylene, 2-fluoro-6-trifluoromethyl-1, 4-phenylene, 2-fluoro-5-trifluoromethyl-1, 4-phenylene, 2-fluoro-6-trifluoromethoxy-1, 4-phenylene, 2-fluoro-5-trifluoromethoxy-1, 4-phenylene, 2, 6-bis (trifluoromethyl) -1, 4-phenylene, 2, 5-bis (trifluoromethyl) -1, 4-phenylene, 2, 6-bis (trifluoromethoxy) -1, 4-phenylene, 2, 5-bis (trifluoromethoxy) -1, 4-phenylene, 2-trifluoromethyl-6-trifluoromethoxy-1, 4-phenylene, 2-trifluoromethyl-5-trifluoromethoxy-1, 4-phenylene.
R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 5 carbon atoms; r is R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Any of the followingMeaning that H on a carbon atom is each independently optionally substituted by F, one or two non-adjacent-CH 2 -optionally substituted with-O-.
As the aforementioned R 3 、R 4 、R 5 、R 6 、R 7 Or R is 8 Examples of the alkyl group having 1 to 5 carbon atoms include straight-chain or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, and isopentyl groups, and cycloalkyl groups such as cyclopropyl, cyclobutyl, and cyclopentyl groups.
As the aforementioned R 3 、R 4 、R 5 、R 6 、R 7 Or R is 8 Examples of the "alkoxy group having 1 to 5 carbon atoms" include a cycloalkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, an n-pentoxy group, an isopentoxy group, or a cyclopropoxy group, a cyclopentoxy group, or a cyclobutoxy group.
As the aforementioned R 3 、R 4 、R 5 、R 6 、R 7 Or R is 8 Examples of the "alkenyl group having 2 to 5 carbon atoms" include ethenyl, propenyl, butenyl, 2-methylpropenyl, 1-pentenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, and 2-methyl-2-butenyl.
As the aforementioned R 3 、R 4 、R 5 、R 6 、R 7 Or R is 8 Examples of the "alkenyloxy group having 3 to 5 carbon atoms" include ethyleneoxy group, propyleneoxy group, butyleneoxy group, 2-methylpropeneoxy group, 1-pentenyloxy group, 2-methyl-1-butenyloxy group, 3-methyl-1-butenyloxy group, 2-methyl-2-butenyloxy group and the like.
R 3 、R 4 、R 5 、R 6 、R 7 Or R is 8 Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 5 carbon atoms, each independently represents H on any carbon atom of these groupsOptionally substituted in the vertical position by F, and in addition, one or two of these groups are not adjacent-CH 2 -optionally substituted with-O-.
Z 3 Represents a single bond or-CH 2 O-。
Z 4 representation-C 2 H 4 -、-CH 2 O-、-S-、-CF 2 O-or-COO-in which-C 2 H 4 Optionally 0 to 4H's are replaced by F's. -C 2 H 4 Examples of the group substituted with F include-CH 2 CHF-、-CH 2 CF 2 -、-CHFCF 2 -, or-CF 2 CF 2 -。
In the positive dielectric anisotropic liquid crystal composition, the compound represented by the formula II is preferably selected from the group consisting of compounds represented by the following formulas II-1 to II-10.
R 3 、R 4 (F) is F or H as defined above.
Preferably, R 3 Is a straight-chain alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. Examples of the straight-chain alkyl group having 1 to 5 carbon atoms include methyl, ethyl, n-propyl, n-butyl, and n-pentyl. Examples of the alkenyl group having 2 to 5 carbon atoms include vinyl, propenyl, butenyl, pentenyl and the like.
R 4 Preferably a straight-chain alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms. Examples of the straight-chain alkyl group having 1 to 5 carbon atoms include methyl, ethyl, n-propyl, n-butyl, and n-pentyl. Examples of the alkenyl group having 2 to 5 carbon atoms include vinyl, propenyl, butenyl, pentenyl and the like.
In the positive dielectric anisotropic liquid crystal composition, the compound represented by the formula III is preferably selected from the group consisting of compounds represented by the following formulas III-1 to III-21.
R 5 、R 6 Is as defined above.
In the positive dielectric anisotropic liquid crystal composition described above, the compound represented by the formula IV is preferably selected from the group consisting of compounds represented by the following formulas IV-1 to IV-44.
R 7 、R 8 Is as defined above.
Preferably, R 7 An alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.
Preferably, R 8 Representation ofAn alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms.
In the liquid crystal composition, the content of the liquid crystal compound represented by the formula I is preferably, for example, 1 to 40% by weight based on the total amount of the liquid crystal composition.
In the liquid crystal composition, the content of the liquid crystal compound represented by the formula II is, for example, 1 to 90% by weight based on the total amount of the liquid crystal composition.
In the liquid crystal composition, the content of the liquid crystal compound represented by the formula III is preferably 1 to 30% by weight, and more preferably 1 to 20% by weight, based on the total amount of the liquid crystal composition, in terms of obtaining a suitable Δn, Δε, viscosity, VHR, rotational viscosity/elastic constant, and the like.
In the positive dielectric anisotropic liquid crystal composition, the content of the liquid crystal compound represented by the formula IV is preferably 1 to 30% by weight, and more preferably 1 to 20% by weight, based on the total amount of the liquid crystal composition, in terms of obtaining a suitable Δn, Δε, viscosity, VHR, rotational viscosity/elastic constant, and the like.
In some embodiments of the positive dielectric anisotropic liquid crystal composition, the components may be contained in the following proportions. For example, the weight percentage of the compound represented by the formula I is 1 to 40%, the weight percentage of the compound represented by the formula II is 1 to 70%, the weight percentage of the compound represented by the formula III is 1 to 30%, and the weight percentage of the compound represented by the formula IV is 1 to 30%.
In some embodiments of the positive dielectric anisotropic liquid crystal composition, the positive dielectric anisotropic liquid crystal composition may further contain a compound represented by the following formula V.
Wherein R is 9 Represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkene having 3 to 5 carbon atomsAn oxy group; r is R 9 Each H on any carbon atom is independently optionally substituted with F, one or two non-adjacent-CH 2 -optionally substituted with-O-.
R 10 Represents H, F, alkyl having 1 to 8 carbon atoms or alkenyl having 2 to 8 carbon atoms, wherein one or two of them are not adjacent to each other, -CH 2 -optionally substituted with-O-, and optionally less than 4H are substituted with F.
Ring A7, ring A8 each independently represent a group selected from the group consisting of: 1, 4-cyclohexylene, 1-methyl-1, 4-cyclohexylene, 2-oxetan-1, 4-diyl, 2, 6-dioxan-1, 4-diyl, cyclohexene-1, 4-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 2-fluoro-3-trifluoromethyl-1, 4-phenylene, 2, 3-bis (trifluoromethyl) -1, 4-phenylene, 2-fluoro-3-trifluoromethoxy-1, 4-phenylene, 2, 3-bis (trifluoromethoxy) -1, 4-phenylene, 2, 6-difluoro-substituted-1, 4-phenylene 2, 5-difluoro-substituted-1, 4-phenylene, 2-fluoro-6-trifluoromethyl-1, 4-phenylene, 2-fluoro-5-trifluoromethyl-1, 4-phenylene, 2-fluoro-6-trifluoromethoxy-1, 4-phenylene, 2-fluoro-5-trifluoromethoxy-1, 4-phenylene, 2, 6-bis (trifluoromethyl) -1, 4-phenylene, 2, 5-bis (trifluoromethyl) -1, 4-phenylene, 2, 6-bis (trifluoromethoxy) -1, 4-phenylene, 2, 5-bis (trifluoromethoxy) -1, 4-phenylene, 2-trifluoromethyl-6-trifluoromethoxy-1, 4-phenylene, 2-trifluoromethyl-5-trifluoromethoxy-1, 4-phenylene;
Z 5 Represents a single bond, -CF 2 O-or-COO-;
t represents 1, 2, 3 or 4;
u represents 1 or 2.
Preferably, the compound of formula V is selected from the group consisting of compounds of formulas V-1 through IV-37 described below.
Wherein R is 9 、R 10 Is as defined above.
Preferably, R 9 Represents H, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, more preferably H, an alkyl group having 1 to 3 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms.
Preferably, R 10 Is F, -CF 3 、-CHF 2 、-CH 2 F、-OCF 3 、-OCHF 2 or-OCH 2 F. Further preferably F, -CF 3 、-OCF 3 or-OCF 3 。
In the case where the compound represented by the formula V is contained in the positive dielectric anisotropic liquid crystal composition, the content of the liquid crystal compound represented by the formula V may be, for example, 1 to 30% by weight, and from the viewpoint of obtaining a suitable Δn, Δε, viscosity, VHR, rotational viscosity/elastic constant, etc., it is preferably 1 to 25%, and more preferably 1 to 20% by weight, based on the total amount of the liquid crystal composition.
In some embodiments of the aforementioned liquid crystal composition, for example, the components may be contained in the following proportions: the weight percentage of the compound shown in the formula I is 1-40%, the weight percentage of the compound shown in the formula II is 1-70%, the weight percentage of the compound shown in the formula III is 1-30%, the weight percentage of the compound shown in the formula IV is 1-30%, and the weight percentage of the compound shown in the formula V is 1-30%.
In some embodiments of the positive dielectric anisotropic liquid crystal composition described above, it is preferable that one or more compounds represented by the following formula VI are further contained in order to obtain a reduction in viscosity, thereby improving the response speed, reducing defects such as ghost, and the like:
in formula VI, R 11 、R 12 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms; and R is 11 、R 12 Each H on any carbon atom is independently optionally substituted with F, wherein one or two non-adjacent-CH' s 2 -optionally substituted with-O-;
ring D represents 1, 4-cyclohexylene, cyclohexene-1, 4-diyl, 2-oxetan-1, 4-diyl, 2, 6-dioxan-1, 4-diyl, 1, 4-phenylene, 2-fluoro-1, 4-diphenylene, 2-methyl-1, 4-diphenylene or 2, 3-difluoro-1, 4-phenylene, wherein any H atom is optionally replaced by-F or-CH 3 Substitution;
ring E represents a group selected from the group consisting of:
Z 6 represents a single bond, -CH 2 O-、-CF 2 O-, -COO-, or-CH 2 CH 2 -；
w, x, y, z each independently represents 0, 1, 2 or 3.
As the aforementioned R 11 、R 12 Examples of the alkyl group having 1 to 8 carbon atoms include Such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like.
As the aforementioned R 11 、R 12 Examples of the "alkoxy group having 1 to 8 carbon atoms" include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy and the like.
As the aforementioned R 11 、R 12 Examples of the "alkenyl group having 2 to 7 carbon atoms" include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-heptenyl group, 2-heptenyl group, 3-heptenyl group, 4-heptenyl group, 5-heptenyl group, 6-heptenyl group and the like.
As the aforementioned R 11 、R 12 Examples of the "alkenyloxy group having 2 to 7 carbon atoms" include: vinyloxy, allyloxy, 3-butenyloxy, 3-pentenyloxy, 4-pentenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 3-heptenyloxy, 4-heptenyloxy, 5-heptenyloxy, 6-heptenyloxy, and the like.
R as described above 11 、R 12 In the alkyl group having 1 to 8 carbon atoms, the alkoxy group having 1 to 8 carbon atoms, the alkenyl group having 2 to 7 carbon atoms, or the alkenyloxy group having 2 to 7 carbon atoms, H in these groups is independently optionally substituted with F, wherein one or two non-adjacent-CH 2 -optionally substituted with-O-.
The compound represented by formula VI is preferably selected from the group consisting of the compounds represented by the following formulas VI-1 to VI-78.
When the compound represented by the formula VI is contained in the liquid crystal composition of the present invention, the content of the compound represented by the formula VI in the liquid crystal composition may be, for example, 1 to 20% by weight, and preferably 1 to 10% by weight.
In addition to the aforementioned liquid crystal compounds, other liquid crystal compounds and non-liquid crystal compounds may be added to the liquid crystal composition of the present invention by those skilled in the art without impairing the desired properties of the liquid crystal composition.
In the positive dielectric anisotropic liquid crystal composition of the present invention, various functional additives such as UV stabilizer, antioxidant, chiral dopant, polymerization initiator, one or more of them may be optionally added.
The antioxidant may be exemplified by, for example:
m represents an integer of 1 to 10;
examples of the chiral dopant include,
wherein R is 0 An alkyl group having 1 to 10 carbon atoms;
as the light stabilizer, for example,
wherein Z is 0 Represents an alkylene group having 1 to 20 carbon atoms, any one or more hydrogens in the alkylene group being optionally substituted with halogen, any one or more-CH' s 2 -optionally substituted with-O-.
Examples of the ultraviolet absorber include,
or->Wherein R is 01 Represents an alkyl group having 1 to 10 carbon atoms.
The amount of the aforementioned additive may be, for example, 0.01% to 1.5% by mass of the total mass of the liquid crystal composition.
[ liquid Crystal display device ]
A second aspect of the present invention provides a liquid crystal display device using the aforementioned liquid crystal composition of the present invention. The liquid crystal display device of the present invention is not particularly limited as long as the liquid crystal composition is contained. Those skilled in the art will be able to select other compositions and structures of the liquid crystal display device as appropriate for the desired performance.
The liquid crystal display device of the present invention is preferably driven in, for example, IPS mode or FFS mode.
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 otherwise specified, all raw materials used can be obtained from public commercial paths, the percentages refer to mass percentages, the temperature is in degrees centigrade (DEG C), and the liquid crystal compound is also a liquid crystal monomer.
The structures of the liquid crystal monomers used in the examples of the present application are represented by the following codes, and the code representation methods of the liquid crystal ring structure, the terminal group and the linking group are shown in the following tables (one) and (two).
Table (one): corresponding code of ring structure
Table (ii): corresponding codes of end groups and linking groups
Examples:
[ liquid Crystal Compound ]
Example 1: preparation of CVEPGU-V-F
Reaction scheme 2: preparation circuit diagram of CVEPGU-V-F
CVEPGU-V-F was prepared according to the preparation route shown in the above scheme 2.
The concrete explanation is as follows:
a-1 structure:preparation of the indicated compounds
Under nitrogen, 387g of 3,4, 5-trifluorophenylboronic acid, 2500ml of tetrahydrofuran, 450g of sodium carbonate, 950ml of deionized water and 12g of tetrakis (triphenylphosphine) palladium were introduced into a three-necked flask. Under stirring, the mixture was heated to a weak reflux, and a solution prepared from 600g of 2-fluoro-4-bromoiodobenzene and 1100ml of tetrahydrofuran was added dropwise for about 3 hours, and after the completion of the dropwise addition, the reflux reaction was continued for 16 hours.
Cooling to 40 ℃, adding toluene and water into the reaction solution, stirring, separating out a water layer, extracting the toluene, crystallizing the mixed solution of the toluene and the ethanol, and obtaining 366g of white powdery compound shown as a formula A-1.
A-2 structure:preparation of the indicated compounds
The clean three-necked flask was purged with nitrogen for 10 minutes. Then 306g of the compound represented by the formula A-1 and 1200ml of anhydrous tetrahydrofuran were added in this order. Stirring is started, liquid nitrogen is introduced for cooling, 430ml of 2.5M butyl lithium n-hexane solution is dripped when the temperature is reduced to minus 78 ℃, and the whole process is at a temperature of minus 70 ℃ to minus 80 ℃. After the dripping, the temperature is kept for 1 hour. After the heat preservation, dropwise adding a pre-prepared THF solution of triisopropyl borate (prepared by dissolving 280g of triisopropyl borate in 300ml of tetrahydrofuran), controlling the internal temperature at-70 to-80 ℃ during dropwise adding, after the dropwise adding is completed for about 1 hour, continuously preserving the heat for 30 minutes, and naturally heating for about 2-3 hours.
When the temperature is raised to about minus 20 ℃, the reaction solution is added into dilute hydrochloric acid for hydrolysis, the hydrolysis solution is stirred for 0.5 hour and then layered, the lower water phase is extracted twice by ethyl acetate, the organic phases are combined, and sodium bicarbonate is neutralized to pH value of 6-7. The solvent was removed by rotary evaporation to give 256g of a white powder, i.e., a compound of formula A-2, which was used directly in the next step without purification.
A structure of formula a-3:preparation of the indicated compounds
700g of deionized water was added to the reaction flask under nitrogen protection, stirring was started, 190g of anhydrous sodium carbonate was added to the three-necked flask, and stirring was performed for about 10 minutes to dissolve. 1000ml toluene, 450ml ethanol, 232g p-bromophenylpropionaldehyde ethylene glycol, 243g of intermediate I-2 prepared in the previous step were added. After the addition, the air in the autoclave was replaced with nitrogen for 1 hour, and 0.5g of bis (di-t-butyl-4-dimethylaminophosphine) palladium chloride catalyst was added. After the catalyst is added, stirring and heating to 75-80 ℃, and preserving heat for 2.5 hours until the reaction is finished.
Cooling the reaction liquid to 20-30 ℃, stopping stirring, standing for layering, and standing an organic layer for later use. The aqueous phase was extracted twice with toluene, the organic phases were combined, washed to neutrality, spin-evaporated to dryness in vacuo and recrystallized from ethanol to yield 325g of intermediate A-3.
A-4 structure:preparation of the indicated compounds
Under the protection of nitrogen, 440ml of toluene, 320g of intermediate A-3 prepared in the previous step and 1200ml of formic acid are added into a three-port bottle, after stirring and fully dissolving at room temperature, the temperature is raised to 60-65 ℃, and the temperature is kept for 5h until the residual amount of the intermediate A-3 is less than or equal to 0.02%.
Stopping stirring, standing for layering, separating a lower formic acid phase, extracting with 100ml of toluene once, combining toluene phases, washing with water once, washing with saturated sodium bicarbonate once, finally washing with saturated brine to be neutral, adding anhydrous sodium sulfate into an organic phase, stirring for drying, filtering, and carrying out vacuum rotary evaporation on a filtrate to obtain 250g of an intermediate A-4, and directly carrying out the next reaction without purification.
A-5 structure:preparation of the indicated compounds
700ml of toluene, 96g of 4-vinylcyclohexyl iodomethane phosphonate are added into a reaction bottle under the protection of nitrogen, the mixture is stirred for about 30 minutes at 20-30 ℃, the temperature is reduced to-5-0 ℃, and a solution prepared from 25g of potassium tert-butoxide and 150ml of THF is dropwise added into the reaction bottle, wherein the dropwise adding process is controlled at-5-0 ℃. After the dripping, the temperature is kept for 2 hours. 150ml toluene and 55g intermediate I-4 are prepared into solution, the temperature is controlled to be between minus 5 and 0 ℃ and the solution is dripped into a reaction bottle, and the temperature is kept for 3 hours after the dripping is finished.
Quenching with tap water, standing for layering, combining organic phases, washing with water to be neutral, stirring and drying with anhydrous sodium sulfate for 0.5-1 hour, filtering with anhydrous sodium sulfate, and decompressing and desolventizing filtrate. And (3) adding petroleum ether into the desolventized solid, boiling, filtering, and reserving filtrate for later use. The resulting solid was suction filtered and the above procedure was repeated 2 times with petroleum ether. The filtrates were combined and passed through a silica gel column. The column passing liquid is decompressed and desolventized to obtain 68g of crude product of cis-and trans-containing A-5, which is directly used for the next configuration transformation.
Single crystal a-6 (CVEPGU-V-F) structure:preparation of the indicated compounds
Under the protection of nitrogen, 150ml of toluene, 50g of intermediate I-5,12g of sodium benzene sulfinate obtained in the previous step and 7ml of 36% concentrated hydrochloric acid (wt%) are added into a reaction bottle, after stirring and fully dissolving at room temperature, the temperature is raised to 60 ℃ and the temperature is kept between 60 ℃ and 65 ℃ for 8 hours, and stirring is carried out.
After the reaction was completed, 20ml of deionized water was added to the reaction flask, stirring was stopped after 30 minutes, and the mixture was allowed to stand for delamination, the lower aqueous phase was separated and extracted twice with toluene. The combined organic phases were washed three times with water to neutrality. The organic phase is desolventized under reduced pressure to give 48g of crude product. The crude product was crystallized three times from ethanol and n-hexane to give a white solid. The material after drying and recrystallization is passed through a silica gel (70-200 meshes) chromatographic column and eluted by n-heptane to obtain 30g of trans CVEPGU-V-F, the mass spectrum of which is shown in figure 1.
MS(EI,m/z):149,315,464
Example 2: preparation of CVEPUQU-V-F
Reaction scheme 3: preparation roadmap for CVEPUQU-V-F
CVEPUQU-V-F was prepared according to scheme 3 shown above.
B-2 structure:preparation of the indicated compounds
The inside air was replaced with nitrogen for 10 minutes in a three-necked flask. 195g of starting material B-1, 1000ml of anhydrous tetrahydrofuran and 140g of triisopropyl borate were then added in succession. Stirring is started, liquid nitrogen is introduced for cooling, 210ml of 2.5M butyl lithium n-hexane solution is dripped when the temperature is reduced to minus 100 ℃, and the whole process is controlled to be at minus 90 ℃ to minus 100 ℃. After the dripping, the temperature is kept for 1 hour. After the heat preservation is continued for 30 minutes, the temperature is naturally raised for about 2 to 3 hours.
When the temperature is raised to about minus 30 ℃, the reaction solution is added into dilute hydrochloric acid for hydrolysis, and the hydrolysis solution is stirred for 1 hour and then is stood for layering. The lower aqueous phase was extracted twice with ethyl acetate, the organic phases were combined and neutralized with sodium bicarbonate to pH 6-7. Spin-steaming desolventizing gave 159g of white powder, intermediate B-2, which was used directly in the next step without purification.
B-3 structure:preparation of the indicated compounds
Under the protection of nitrogen, 300g of deionized water is added into a reaction bottle, stirring is started, 76g of anhydrous sodium carbonate is added into a three-port bottle, and stirring is performed for about 10 minutes to dissolve the sodium carbonate. 460ml toluene, 150ml ethanol, 93g p-bromophenylpropionaldehyde ethylene glycol, 135g of intermediate B-2 prepared in the previous step were added. After the addition, the air in the flask was replaced with nitrogen for 30 minutes, and 0.15g of bis (di-t-butyl-4-dimethylaminophosphine) palladium chloride catalyst was added. After the catalyst is added, stirring and heating to 75-80 ℃, and preserving heat for 3 hours until the reaction is finished.
After the temperature of the reaction solution is reduced to 20-30 ℃, 300ml of water is added, the mixture is stirred for 15 minutes, the mixture is stood for layering, and an organic layer is used. The aqueous phase was extracted twice with toluene, the organic phases were combined, washed to neutrality, spin-evaporated to dryness in vacuo and recrystallized from ethanol to give 140g of intermediate B-3, which was used directly in the next step.
B-4 structure:preparation of the indicated compounds
150ml of toluene, 120g of intermediate B-3 prepared in the previous step and 360ml of formic acid are added into a three-port bottle under the protection of nitrogen, after stirring and fully dissolving at room temperature, the temperature is raised to 60-65 ℃, and the stirring is carried out for 3 hours under the heat preservation until the residual amount of the raw material B-3 is less than or equal to 0.02 percent.
Stirring was stopped, the layers were allowed to stand, the organic layer replaced, and the lower formic acid phase was extracted once with 200ml toluene. Combining toluene phases, washing once with saturated sodium bicarbonate, washing once with saturated brine to be neutral, adding an organic phase, stirring and drying the mixture with anhydrous sodium sulfate, carrying out suction filtration, transferring filtrate to reduced pressure for desolventizing to obtain 105g of an intermediate B-4, and directly carrying out the next reaction without purification.
B-5 structure:preparation of the indicated compounds
400ml of tetrahydrofuran, 73g of 4-vinylcyclohexyl iodomethane phosphonate are added into a reaction bottle under the protection of nitrogen, the mixture is stirred for about 30 minutes at 20-30 ℃, the temperature is reduced to minus 15-minus 10 ℃, and a solution prepared from 20g of potassium tert-butoxide and 125ml of THF is dropwise added into the reaction bottle, and the temperature is controlled to minus 15-minus 10 ℃ in the dropwise adding process. After the dripping, the temperature is raised to-5 to 0 ℃ and kept for 2 hours. 150ml toluene and 55g intermediate B-4 are prepared into solution, the temperature is controlled between minus 15 ℃ and minus 10 ℃ and the solution is dripped into a reaction bottle, and the temperature is kept for 3 hours after the dripping is finished.
Quenching with deionized water, standing for layering, extracting the organic layer with toluene, mixing the organic phases, washing to neutrality, stirring and drying with anhydrous sodium sulfate for 0.5-1 hr, filtering with anhydrous sodium sulfate, and vacuum desolventizing. And (3) adding petroleum ether into the desolventized solid, boiling, filtering, and reserving filtrate for later use. The resulting solid was suction filtered and the above procedure was repeated 2 times with petroleum ether. Combining the three hot filtration filtrates, and passing through a silica gel column. The column passing liquid is decompressed and desolventized to obtain 62g of crude product of the compound shown as the B-5 containing cis-form and trans-form, and the crude product is directly used for the next configuration conversion.
Single crystal B-6 (CVEPUQU-V-F) structure:is prepared from
Toluene, 120ml and 52.5g of intermediate B-5 obtained in the previous step, 12.5g of sodium benzene sulfinate and 7.5ml of 36% concentrated hydrochloric acid (wt%) are added into a reaction bottle under the protection of nitrogen, and after stirring and complete dissolution at room temperature, the temperature is raised to 60 ℃ and the temperature is kept between 60 ℃ and 65 ℃ for stirring for 12 hours.
After the reaction was completed, 40ml of deionized water was added to the reaction flask, stirring was stopped after 30 minutes, and the mixture was allowed to stand for delamination, the lower aqueous phase was separated and extracted twice with toluene. The combined organic phases were washed three times with water to neutrality. The organic phase is desolventized under reduced pressure to give 47.5g of crude product. The crude product was crystallized four times with a mixed solvent of ethanol and toluene to give a white solid. The recrystallized material was dried and passed through a silica gel (70-200 mesh) column and eluted with n-heptane to give 26.5g of trans CVEPUQU-V-F, the mass spectrum of which is shown in FIG. 2.
MS(EI,m/z):149,252,401,548。
According to a method similar to the above-mentioned synthetic method of CVEPGU-V-F, CVEPUQU-V-F, liquid crystal compounds described in the following table were prepared, and T was measured after 10% of each compound monomer was compatible with 90% of the mother liquid crystal ni Delta n and delta epsilon, and then calculating the T of the monomer by adopting an extrapolation method ni 、Δn、Δε。
The matrix liquid crystal comprises the following components in percentage by mass:
| CCG-2-F | 10％ |
| CCP-V-1 | 20％ |
| CCP-V2-1 | 20％ |
| CPU-3-F | 20％ |
| CP-3-O2 | 15％ |
| CP-3-O1 | 15％ |
T ni representing the temperature at which the liquid crystalline monomer changes phase from nematic to clear phase, the temperature being measured by an MP-90 device.
Delta epsilon represents dielectric anisotropy, delta epsilon=epsilon ∥ -ε ⊥ Wherein ε is ∥ For dielectric constant parallel to the molecular axis ε ⊥ The dielectric constant perpendicular to the molecular axis, test conditions: alCT-IR1, 18 μm vertical box at 25deg.C.
Δn represents optical anisotropy, Δn=n e -n o Wherein n is o Refractive index of ordinary ray, n e For the refractive index of the extraordinary ray, test conditions: 589nm, 25.+ -. 0.2 ℃.
| Sequence number | Liquid crystal compound structure | T ni (℃) | Δn | Δε |
| 1 | CVEDGUQU-V-F | 205.9 | 0.1760 | 33.8 |
| 2 | CVEPGU-V-T | 158.5 | 0.2250 | 20.6 |
| 3 | CVEPGU-3-F | 173.5 | 0.2300 | 13.3 |
| 4 | CVEPGU-3-OT | 180.5 | 0.2215 | 17.5 |
| 5 | CVEPGU-V-F | 168.0 | 0.2285 | 12.9 |
| 6 | CVEPGU-V-OT | 174.5 | 0.2190 | 17.0 |
| 7 | CVEPGUQU-3-F | 232.5 | 0.2585 | 24.5 |
| 8 | CVEPUQU-V-OT | 110.5 | 0.1590 | 22.5 |
| 9 | CVEPUQU-V-F | 102.3 | 0.1678 | 18.2 |
| 10 | CVEPPGU-3-F | 335.2 | 0.3470 | 14.0 |
| 11 | CVEPPGU-V-F | 330.5 | 0.3450 | 13.5 |
[ preparation of liquid Crystal composition ]
Liquid crystal compositions of different compositions were prepared in the following examples and comparative examples, wherein the monomer structures, amounts (weight percentages) of specific compounds used in each example, and results of testing performance parameters of the resulting liquid crystal media are shown in the following tables, respectively.
The temperature units involved in each example are in degrees celsius, and the specific meaning of the other symbols and the test conditions are as follows:
gamma1 (mPas) represents the rotation viscosity coefficient of the liquid crystal compound, and the measurement method comprises the following steps: the instrument and equipment INSTEC is ALCT-IR1, a vertical box with the thickness of 18 micrometers and the temperature of 25 ℃ is abbreviated as 'G1';
K 11 to give a torsional spring constant, K 33 For the splay elastic constant, the test conditions were: 25 ℃, INSTEC, ALCT-IR1, 18 micron vertical box;
delta epsilon represents dielectric anisotropy, delta epsilon=epsilon ∥ -ε ⊥ Wherein ε is ∥ For dielectric constant parallel to the molecular axis ε ⊥ For dielectric constants perpendicular to the molecular axis, test conditions: 25 ℃, INSTEC, ALCT-IR1, 18 micron vertical box;
Δn represents optical anisotropy, Δn=n e -n o Wherein n is o Refractive index of ordinary ray, n e For the refractive index of the extraordinary ray, test conditions: 589nm, 25.+ -. 0.2 ℃.
VHR represents the voltage holding ratio (%) after uv irradiation, and the test conditions were 20±2 ℃, voltage ±5V, pulse width of 1ms, and voltage holding time of 16.7ms. The test equipment is an ALCT-IV1 liquid crystal performance comprehensive tester. In the ultraviolet polymerization of the polymerizable compound for VHR test, 365nm wavelength was used and the irradiation light intensity was 2.5Mw/cm 2 Is irradiated by ultraviolet light for 34 minutes.
In the present invention, the preparation method of the liquid crystal composition is as follows: 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.
And filling the obtained liquid crystal composition between two substrates of the liquid crystal display for performance test.
The liquid crystal compositions of examples exhibiting positive dielectric anisotropy were obtained by compounding the liquid crystal compounds represented by the above formulas I to VI with other components, and the compositions and contents of the respective components in the liquid crystal compositions of examples are shown in the following table. Further, comparative examples 1 and 2 were obtained by substituting a general-purpose positive liquid crystal compound for the compound represented by the general formula I in example 1 and example 5.
Table 1 the liquid crystal composition of example 1 has the composition ratios and the performance parameters thereof
TABLE 2 component proportions and Performance parameters of the liquid Crystal composition of example 2
TABLE 3 component proportions and Performance parameters of the liquid Crystal composition of example 3
TABLE 4 component proportions and Performance parameters of the liquid Crystal composition of example 4
TABLE 5 component proportions and Performance parameters of the liquid Crystal composition of example 5
TABLE 6 component proportions and Performance parameters of the liquid Crystal composition of example 6
TABLE 7 component proportions and Performance parameters of the liquid Crystal composition of example 7
TABLE 8 component proportions and Performance parameters of the liquid Crystal composition of example 8
Comparative example 1 the formulation is shown in table 9 below, which contains no compound of formula I according to the present invention.
Table 9 component proportions and Performance parameters of the liquid Crystal Medium of comparative example 1
Comparative example 2 the formulation is shown in table 10 below, which contains no compound of formula I according to the present invention.
Table 10 component proportions and Performance parameters of the liquid Crystal Medium of comparative example 2
Although not exhaustive of all liquid crystal mixtures which are claimed, it is foreseeable by the person skilled in the art that, on the basis of the above-described embodiments which have been disclosed, other liquid crystal materials of the same type can be obtained in a similar manner, without the need for inventive labour, only in combination with professional attempts. Representative embodiments are only exemplified herein for limited space.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (14)
1. A positive dielectric anisotropic liquid crystal compound selected from the group consisting of compounds represented by the following formulas I-1 to I-36:
wherein R is 1 Represents H, an alkyl group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, wherein optionally 4 or less H are substituted with F;
R 2 represents H, F, alkyl having 1 to 8 carbon atoms or alkenyl having 2 to 8 carbon atoms, wherein one or two of them are not adjacent to each other, -CH 2 -optionally substituted with-O-, optionally less than 4H are substituted with F.
2. A liquid crystal composition comprising the liquid crystal compound according to claim 1.
3. The liquid crystal composition according to claim 2, which is a positive dielectric anisotropic liquid crystal composition, further comprising: at least one compound of formula II;
at least one compound of formula III: the method comprises the steps of,
at least one compound of formula IV:
wherein R is 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 5 carbon atoms; r is R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each H on any carbon atom is independently optionally substituted with F, one or two non-adjacent-CH 2 -optionally substituted with-O-;
Z 4 representation-C 2 H 4 -、-CH 2 O-、-S-、-CF 2 O-or-COO-wherein-C 2 H 4 -wherein optionally 0 to 4H are substituted by F;
Z 3 represents a single bond or-CH 2 O-；
p represents 0, 1, 2 or 3;
q, r, v each independently represent 0, 1 or 2;
s is selected from 1, 2,3 or 4;
ring A1, ring A2, ring A3, ring A4, ring A5, ring A6 each independently represent a group selected from the group consisting of: 1, 4-cyclohexylene, 1-methyl-1, 4-cyclohexylene, 2-oxetan-1, 4-diyl, 2, 6-dioxan-1, 4-diyl, cyclohexene-1, 4-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 2-fluoro-3-trifluoromethyl-1, 4-phenylene, 2, 3-bis (trifluoromethyl) -1, 4-phenylene, 2-fluoro-3-trifluoromethoxy-1, 4-phenylene, 2, 3-bis (trifluoromethoxy) -1, 4-phenylene, 2, 6-difluoro-substituted-1, 4-phenylene 2, 5-difluoro-substituted-1, 4-phenylene, 2-fluoro-6-trifluoromethyl-1, 4-phenylene, 2-fluoro-5-trifluoromethyl-1, 4-phenylene, 2-fluoro-6-trifluoromethoxy-1, 4-phenylene, 2-fluoro-5-trifluoromethoxy-1, 4-phenylene, 2, 6-bis (trifluoromethyl) -1, 4-phenylene, 2, 5-bis (trifluoromethyl) -1, 4-phenylene, 2, 6-bis (trifluoromethoxy) -1, 4-phenylene, 2, 5-bis (trifluoromethoxy) -1, 4-phenylene, 2-trifluoromethyl-6-trifluoromethoxy-1, 4-phenylene, 2-trifluoromethyl-5-trifluoromethoxy-1, 4-phenylene.
4. A liquid crystal composition according to claim 3, wherein the compound represented by formula ii is selected from the group consisting of compounds represented by the following formulas ii-1 to ii-10:
R 3 、R 4 (F) is as defined in claim 3, and (F) represents F or H.
5. A liquid crystal composition according to claim 3, wherein the compound represented by formula iii is selected from the group consisting of compounds represented by the following formulas iii-1 to iii-21:
R 5 、R 6 is as defined in claim 3.
6. A liquid crystal composition according to claim 3, wherein the compound represented by formula IV is selected from the group consisting of compounds represented by the following formulas IV-1 to IV-44:
R 7 represents an alkenyl group having 2 to 5 carbon atoms, and R 7 Each H on any carbon atom is independently optionally substituted with F, one or two non-adjacent-CH 2 -optionally substituted with-O-;
R 8 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 5 carbon atoms; r is R 8 Each H on any carbon atom is independently optionally substituted with F, one or two non-adjacent-CH 2 -optionally substituted with-O-.
7. The positive dielectric anisotropic liquid crystal composition according to claim 3, further comprising a compound represented by the following formula V:
Wherein R is 9 Represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 5 carbon atoms; r is R 9 H on any carbon atom of (B)Optionally substituted by F, one or two non-adjacent-CH' s 2 -optionally substituted with-O-;
R 10 represents H, F, alkyl having 1 to 8 carbon atoms or alkenyl having 2 to 8 carbon atoms, wherein one or two of them are not adjacent to each other, -CH 2 -optionally substituted with-O-, and optionally less than 4H are substituted with F;
ring A7, ring A8 each independently represent a group selected from the group consisting of:
1, 4-cyclohexylene, 1-methyl-1, 4-cyclohexylene, 2-oxetan-1, 4-diyl, 2, 6-dioxan-1, 4-diyl, cyclohexene-1, 4-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 2-fluoro-3-trifluoromethyl-1, 4-phenylene, 2, 3-bis (trifluoromethyl) -1, 4-phenylene, 2-fluoro-3-trifluoromethoxy-1, 4-phenylene, 2, 3-bis (trifluoromethoxy) -1, 4-phenylene, 2, 6-difluoro-substituted-1, 4-phenylene 2, 5-difluoro-substituted-1, 4-phenylene, 2-fluoro-6-trifluoromethyl-1, 4-phenylene, 2-fluoro-5-trifluoromethyl-1, 4-phenylene, 2-fluoro-6-trifluoromethoxy-1, 4-phenylene, 2-fluoro-5-trifluoromethoxy-1, 4-phenylene, 2, 6-bis (trifluoromethyl) -1, 4-phenylene, 2, 5-bis (trifluoromethyl) -1, 4-phenylene, 2, 6-bis (trifluoromethoxy) -1, 4-phenylene, 2, 5-bis (trifluoromethoxy) -1, 4-phenylene, 2-trifluoromethyl-6-trifluoromethoxy-1, 4-phenylene, 2-trifluoromethyl-5-trifluoromethoxy-1, 4-phenylene;
Z 5 Represents a single bond, -CF 2 O-or-COO-;
t represents 1, 2,3 or 4;
u represents 1 or 2.
8. The liquid crystal composition according to claim 7, wherein the compound represented by formula V is selected from the group consisting of compounds represented by the following formulas V-1 to V-37:
wherein R is 9 、R 10 Is as defined in claim 7.
9. A liquid crystal composition according to claim 3, further comprising one or more compounds of formula VI:
in the formula VI, R 11 、R 12 Each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an alkenyloxy group having 2 to 7 carbon atoms; and R is 11 、R 12 Each H on any carbon atom is independently optionally substituted with F, wherein one or two non-adjacent-CH' s 2 -optionally substituted with-O-;
ring D represents 1, 4-cyclohexylene, cyclohexene-1, 4-diyl, 2-oxetan-1, 4-diyl, 2, 6-dioxan-1, 4-diyl, 1, 4-phenylene, 2-fluoro-1, 4-diphenylene, 2-methyl-1, 4-diphenylene or 2, 3-difluoro-1, 4-phenylene, wherein any H atom is optionally replaced by-F or-CH 3 Substitution;
ring E represents a group selected from the group consisting of:
Or->
Z 6 Represents a single bond, -CH 2 O-、-CF 2 O-, -COO-, or-CH 2 CH 2 -；
w, x, y, z each independently represents 0, 1, 2 or 3.
10. The liquid crystal composition according to claim 9, wherein the compound represented by formula VI is selected from the group consisting of compounds represented by the following formulas VI-1 to VI-78:
11. the liquid crystal composition according to claim 3, wherein the weight percentage of the compound represented by formula I is 1 to 40%, the weight percentage of the compound represented by formula ii is 1 to 70%, the weight percentage of the compound represented by formula iii is 1 to 30%, and the weight percentage of the compound represented by formula IV is 1 to 30%.
12. The liquid crystal composition according to claim 7, wherein the liquid crystal composition comprises 1 to 40% by weight of the compound represented by formula I, 1 to 70% by weight of the compound represented by formula ii, 1 to 30% by weight of the compound represented by formula iii, 1 to 30% by weight of the compound represented by formula IV, and 1 to 30% by weight of the compound represented by formula V.
13. The liquid crystal composition according to claim 9, wherein the liquid crystal composition comprises 1 to 40% by weight of the compound represented by formula I, 1 to 70% by weight of the compound represented by formula ii, 1 to 30% by weight of the compound represented by formula iii, 1 to 30% by weight of the compound represented by formula IV, 1 to 30% by weight of the compound represented by formula V, and 1 to 20% by weight of the compound represented by formula VI.
14. A liquid crystal display device, characterized in that the liquid crystal composition comprises the liquid crystal compound according to claim 1, or the liquid crystal composition according to any one of claims 2 to 13; the liquid crystal display device is an active matrix display device, or a passive matrix display device.
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