CN114806596B - Silicon-containing liquid crystal compound and preparation method and application thereof - Google Patents
Silicon-containing liquid crystal compound and preparation method and application thereof Download PDFInfo
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- CN114806596B CN114806596B CN202210473425.9A CN202210473425A CN114806596B CN 114806596 B CN114806596 B CN 114806596B CN 202210473425 A CN202210473425 A CN 202210473425A CN 114806596 B CN114806596 B CN 114806596B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 74
- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 19
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000010703 silicon Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title abstract description 12
- -1 methoxy, ethoxy, propoxy, butoxy, propenoxy, butenyloxy, pentoxy, pentenyloxy Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000013538 functional additive Substances 0.000 claims description 4
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 2
- 150000003377 silicon compounds Chemical class 0.000 claims 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 claims 1
- 239000000463 material Substances 0.000 abstract description 11
- 230000003287 optical effect Effects 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000004404 heteroalkyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-UHFFFAOYSA-N 0.000 description 1
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical compound FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 1
- GUYHXQLLIISBQF-UHFFFAOYSA-N 1-cyclohexyl-2-fluorobenzene Chemical compound FC1=CC=CC=C1C1CCCCC1 GUYHXQLLIISBQF-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- HKPQSAMLXJHFSU-UHFFFAOYSA-N chloro-cyclopentyl-dimethylsilane Chemical compound C[Si](C)(Cl)C1CCCC1 HKPQSAMLXJHFSU-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004405 heteroalkoxy group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000003245 working effect Effects 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
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
-
- 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention relates to the technical field of liquid crystal materials, in particular to a silicon-containing liquid crystal compound and a preparation method and application thereof. The silicon-containing liquid crystal compound has a structure shown in a general formula I; the silicon-containing liquid crystal compound has the characteristics of larger vertical dielectric anisotropy, lower optical anisotropy, lower rotational viscosity, good liquid crystal intersolubility and the like, can be widely applied to the field of liquid crystal display, can achieve the application purposes of low power consumption, wide viewing angle and high contrast ratio, effectively improves the display quality, and has important application value.
Description
Technical Field
The invention relates to the technical field of liquid crystal materials, in particular to a silicon-containing liquid crystal compound and a preparation method and application thereof.
Background
In recent years, liquid crystal display devices have been developed more and more rapidly, and various types such as a vehicle-mounted small-sized liquid crystal display device, a portable liquid crystal display device, an ultra-thin liquid crystal display device, and the like have also been developed. Taking television as an example, the portable electronic device is characterized by light weight, small occupied space, convenient movement and the like, and further comprises a notebook type personal computer, a mobile phone and the like.
The liquid crystal material has great research value and good application prospect in the fields of information display materials, organic optoelectronic materials and the like as an environment material. At present, the technology of TFT-LCD products is mature, the technical problems of visual angle, resolution, color saturation, brightness and the like are successfully solved, and large-size and medium-small-size TFT-LCD displays gradually occupy the mainstream position of flat panel displays in the respective fields. However, the requirements for display technology are continuously increasing, and the liquid crystal display is required to realize faster response, lower driving voltage to reduce power consumption, etc., and the liquid crystal material is also required to have low voltage driving, fast response, wide temperature range and good low temperature stability.
The liquid crystal material plays an important role in improving the performance of a liquid crystal display, and in order to improve the performance of the material and enable the material to adapt to new requirements, the research on the synthesis and structure-performance relationship of a novel structure liquid crystal compound becomes an important work in the field of liquid crystals.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims to provide a liquid crystal compound with a silicon-containing structure, which has the characteristics of larger vertical dielectric anisotropy, lower optical anisotropy, lower rotational viscosity, good liquid crystal intersolubility and the like, can be widely used in the field of liquid crystal display, can achieve the application purposes of low power consumption, wide viewing angle and high contrast ratio, effectively improves the display quality, and has important application value; another object of the present invention is to provide a method for preparing the liquid crystal compound and application thereof.
Specifically, the invention provides the following technical scheme:
the invention provides a silicon-containing liquid crystal compound, which has a structure shown in a general formula I:
In the formula I, the compound (I),
V 1、V2 are each independently selected from single bond 、-CH2-、-CH2CH2-、-CH＝CH-、-COO-、-OOC、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4- or-cf=cf-;
R 1、R2、R3、R4 is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, straight chain alkyl with C 1-C40, straight chain alkoxy with C 1-C40, straight chain heteroalkyl with C 1-C40, straight chain heteroalkoxy with C 1-C40, branched or cyclic alkyl with C 3-C40, branched or cyclic alkoxy with C 3-C40, branched or cyclic heteroalkyl with C 3-C40, branched or cyclic heteroalkoxy with C 3-C40, alkenyl or alkynyl with C 2-C40, aryl with 6 to 80 carbon atoms or heteroaryl with 2 to 60 carbon atoms, R 2 and R 3 may optionally be joined or fused together with the Si to which they are attached to form a substituted or unsubstituted ring with or without one or more additional N, O, S or Si heteroatoms in the ring formed; one or more hydrogen atoms in R 1、R4 may be optionally substituted with fluorine atoms;
X 1 represents O or S;
R 0 is hydrogen or fluorine;
t 1、T2 is selected from the group consisting of a single bond or:
* -and- (x) represents a bond.
Aryl groups in the sense of the present invention preferably contain 6 to 60 carbon atoms, heteroaryl groups in the sense of the present invention contain 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl is herein considered to mean a simple aromatic ring, i.e. benzene, biphenyl, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. The hydrogen on an aryl or heteroaryl group is simply replaced or substituted to form a substituted aryl or substituted heteroaryl group, such as fluorobenzene, difluorobenzene, trifluorobenzene, tetrafluorobenzene, cyclohexylbenzene, cyclohexylfluorobenzene, and the like, referred to as aryl or heteroaryl.
Alkyl, alkenyl or alkynyl groups having 1 to 40 carbon atoms in the sense of the present invention are preferably taken to mean the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. Alkoxy is preferably an alkoxy group having 1 to 40 carbon atoms, which is taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octoxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy. Heteroalkyl is preferably alkyl having from 1 to 40 carbon atoms, meaning a radical in which the individual hydrogen atoms or-CH 2 -groups may be replaced by oxygen, sulfur, halogen atoms, is taken to mean alkoxy, alkylthio, fluoroalkoxy, fluoroalkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethoxy, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butylenethio, butyleneoxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene thio, acetylenyloxy, acetylenylthio, propynyloxy, butynylthio, pentynyloxy, pentynylthio, hexyloxy, hexylynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 -groups may be replaced by the above groups; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
Preferably, the silicon-containing liquid crystal compound comprises one or more of the following structures:
Further, each of said V 1、V2 is independently selected from a single bond, -CH 2O-、-OCH2-、-CH2-、-CH2CH2-、-CF2O-、-OCF2 -, or-COO-.
Further, the R 2、R3 are the same or different and are each independently selected from the group consisting of methyl, ethyl, nitrile, R 2 and R 3 may optionally be joined and together with the Si to which they are attached form a substituted or unsubstituted ring with or without one or more additional N, O, S or Si heteroatoms in the ring formed.
Further, the R 1、R4 are the same or different and are each independently selected from the group consisting of a linear alkyl group having C 1-C40, a linear alkoxy group having C 1-C40, a linear heteroalkyl group having C 1-C40, a linear heteroalkyl group having C 1-C40, a branched or cyclic alkyl group having C 3-C40, a branched or cyclic alkoxy group having C 3-C40, a branched or cyclic heteroalkyl group having C 3-C40, a branched or cyclic heteroalkyl group having C 3-C40, an alkenyl or alkynyl group having C 2-C40; one or more hydrogen atoms in R 1、R4 may be optionally substituted with fluorine atoms.
Further, each of said T 1、T2 is independently selected from the group consisting of a single bond or:
* -and- (x) represents a bond.
According to an embodiment of the invention, R 0 is fluoro; x 1 is S or O.
According to an embodiment of the present invention, the R 2、R3 are the same or different and are each independently selected from the group consisting of methyl, ethyl.
According to an embodiment of the present invention, the R 1、R4 are the same or different and are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, propenyl, butenyl, pentyl, pentenyl, methoxy, ethoxy, propoxy, butoxy, propenoxy, butenyloxy, pentoxy, pentenyloxy, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, pentafluoroethyl, cyclopropoxy, cyclobutoxy, cyclopentoxy or pentafluoroethoxy.
Preferably, the X 1 is sulfur; r 1、R4 are the same or different and are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, propenyl, butenyl, pentyl, pentenyl.
Preferably, the silicon-containing liquid crystal compound comprises one or more of the structures LS01-LS286 shown below:
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The invention also provides a preparation method of the silicon-containing liquid crystal compound, which comprises the following steps:
Wherein R 0-R4、X1、V1、V2、T1、T2 has the same meaning as defined above.
The raw materials for synthesizing the compound shown in the formula I can be purchased through commercial paths, and the methods of the principle, the operation process, the conventional post treatment, the column purification, the recrystallization purification and the like are well known to the synthesis personnel in the field, so that the synthesis process can be completely realized, and the target product is obtained.
All the steps of all the above methods are carried out in a solvent; the solvent is at least one selected from tetrahydrofuran, 2-methyltetrahydrofuran, N-dimethylformamide, dimethyl sulfoxide, 1-methylpyrrolidin-2-one, ethanol, methanol, dichloromethane, acetone, toluene and deionized water.
The invention also provides a liquid crystal medium comprising one or more of the above-described silicon-containing liquid crystal compounds.
Preferably, the liquid-crystalline medium further comprises, as second component, one or more compounds of the formula II:
Wherein,
Each R 7、R8 is independently selected from the group consisting of the groups defined below A, B, C:
A: a linear alkyl group having C 1-C7 or a linear alkoxy group having C 1-C7;
b: a group formed after one or more of the groups in a are replaced by-CH 2 -, O-, COO-, OOC-, or-ch=ch-;
C: a group formed after one or more hydrogen atoms in any of the groups a are replaced by F, cl, -ch=ch 2, or-ch=ch-CH 3;
Ring B, ring C, ring D, ring E are each independently selected from the group consisting of:
and at least one of the rings B, C, D, E is selected from One of the following;
m, n, o are each independently 0 or 1;
each Z 1、Z2、Z3 is independently selected from the group consisting of a single bond, -C 2H4 -, ch=ch-, * -COO-, OOC-, CH 2O-*、*-OCH2-*、*-CF2 O-, and OCF 2 -, wherein any H may be replaced by F;
* -and- (x) indicates the position at which the substituent is bonded;
Preferably, the liquid-crystalline medium further comprises one or more compounds of the formula III:
Wherein,
R 9、R10 is each independently selected from the group consisting of alkyl having C 1-C10 or alkenyl having C 2-C10, wherein any of-CH 2 -may be replaced by-CH 2O-、-OCH2 -,Instead, any H atom may be replaced by F;
Ring F, ring G, ring I, ring J are each independently selected from the group consisting of:
p, q, r are each independently 0 or 1;
Each Z 4、Z5、Z6 is independently selected from the group consisting of a single bond, -C 2H4 -, ch=ch-, * -COO-, OOC-, CH 2O-*、*-OCH2-*、*-CF2 O-, and OCF 2 -, wherein any H may be replaced by F;
* -and- (x) indicates the position at which the substituents are bonded.
Preferably, in the liquid crystal medium, the mass percentage of the liquid crystal compound is 1-24%, the mass percentage of the compound with the structural formula II is 35-58%, and the mass percentage of the compound with the structural formula III is 30-46%.
Further, the compound with the structural formula II comprises compounds shown in the following formulas II-1 to II-15:
Wherein,
Each R 7、R8 is independently selected from the group consisting of the groups defined below A, B, C:
A: a linear alkyl group having C 1-C7 or a linear alkoxy group having C 1-C7;
b: a group formed after one or more of the groups in a are replaced by-CH 2 -, O-, COO-, OOC-, or-ch=ch-;
C: a group formed after one or more hydrogen atoms in any of the groups a are replaced by F, cl, -ch=ch 2, or-ch=ch-CH 3;
The above-mentioned rings H 1, H 2 are each independently selected from the group consisting of:
Further, the compound with the structural formula III comprises compounds shown in the following formulas III-1 to III-16:
Wherein R 9、R10 is each independently selected from the group consisting of alkyl having C 1-C10 or alkenyl having C 2-C10, any of which-CH 2 -may be replaced by-CH 2O-、-OCH2 -, Instead, any H atom may be replaced by F; (F) each independently represents F or H.
Preferably, the liquid crystal medium further comprises one or more functional additives; the functional additive comprises an antioxidant, a chiral agent, a light stabilizer or an ultraviolet absorber.
The invention also provides a consumer product comprising a liquid crystalline medium as described above.
Such consumer products include, but are not limited to, flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with less than 2 inches diagonal, 3-D displays, virtual or augmented reality displays, vehicles, video walls containing a plurality of tiled displays, theatre or gym screens, phototherapy devices, and signs.
Unless otherwise indicated, all starting materials used in the present invention are commercially available, and any ranges recited herein include any number between the endpoints and any subrange formed by any number between the endpoints or any number between the endpoints.
The beneficial effects of the invention are as follows:
The silicon-containing liquid crystal compound provided by the invention has the chemical main structure of dibenzothiophene or dibenzofuran, the structure has larger dielectric anisotropy, and meanwhile, a silane-based structure is introduced to one side of the dibenzothiophene or dibenzofuran to form a strong synergistic effect, so that the negative dielectric anisotropy of the liquid crystal compound is extremely high, a clearing point is obviously improved, the optical anisotropy is relatively high, the rotation viscosity and the liquid crystal intersolubility are moderate, the low-temperature working effect is excellent, and the performances in the aspects of thermal stability, chemical stability, optical stability, mechanics and the like are good; therefore, the driving voltage is effectively reduced, the response speed of the liquid crystal display device is improved, and the liquid crystal display device has the characteristics of good charge retention rate and the like. Therefore, the compound shown in the formula I can improve the intersolubility and response speed of the liquid crystal compound, improve the low-temperature stability of mixed crystals, expand the application range of the liquid crystal mixture and have important application value.
Detailed Description
The following examples are illustrative of the invention and are not intended to limit the scope of the invention.
The specific techniques or conditions are not identified in the examples and are described in the literature in this field or are carried out in accordance with the product specifications. The reagents or equipment used were conventional products available for purchase by regular vendors without the manufacturer's attention.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the disclosure and percentages such as percentages by mass unless otherwise indicated. The novel series of liquid-crystalline compounds provided by the present invention, all of which are carried out under well-known suitable conditions, involve some simple organic preparation, for example the preparation of phenylboronic acid, which can be synthesised by a skilled operating skill and are not described in detail in the present invention.
Example 1
Preparation of compound LS 65:
Under the protection of nitrogen, 20.0mmol of 4, 6-difluoro-3-propoxy dibenzo [ b, d ] thiophene (reactant 1) is dissolved in 60mL of dry THF, cooled to-100 ℃,20.0mmol of potassium tert-butoxide is added, 24.0mmol of n-butyllithium n-hexane solution is slowly added dropwise, stirring reaction is carried out for 30 minutes, 24.0mmol of n-amyl dimethyl chlorosilane (reactant 2) is added dropwise, stirring reaction is carried out for 2 hours at room temperature, 20mL of saturated ammonium chloride aqueous solution is added, extraction is carried out by ethyl acetate, an organic phase is collected, drying, filtration, decompression concentration and drying of filtrate are carried out, separation and purification are carried out by using a silica gel column, ethanol recrystallization are carried out, and white solid is obtained, yield: 92%, HRMS, m/z:407.1612[ M+H ].
Example 2
Preparation of compound LS 126:
Under the protection of nitrogen, 20.0mmol of 4, 6-difluoro-3- ((4-propylcyclohexyl) methoxy) dibenzo [ b, d ] thiophene is dissolved in 80mL of dry THF, the temperature is reduced to minus 78 ℃, 24.0mmol of n-butyllithium n-hexane solution is added dropwise, stirring reaction is carried out for 1 hour, 24.0mmol of cyclopentyl dimethylchlorosilane is added dropwise again, stirring reaction is carried out for 1 hour at room temperature, 20mL of saturated ammonium chloride aqueous solution is added, extraction is carried out by ethyl acetate, an organic phase is collected, drying and filtration are carried out, the filtrate is concentrated to dryness under reduced pressure, silica gel column separation and purification are carried out, ethanol recrystallization is carried out, and white solid is obtained, yield: 87%, HRMS, m/z:501.2393[ M+H ].
Referring to the synthesis method similar to that of example 1 and example 2, the liquid crystal compounds shown in the following table 1 were prepared:
TABLE 1
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Examples of mixtures
Examples 3 to 15:
examples 3-15 show the preparation of different liquid crystal media, wherein the monomer structure, amount (weight percent) of the specific compounds of each example, and the results of the performance parameter test of the obtained liquid crystal media are shown in tables 3-15, 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:
p. represents the clear point (. Degree. C.) of the liquid crystal, test instrument: mettler-Toledo-FP System micro thermal analyzer;
γ1 is the rotational viscosity (mpa·s) and the test conditions are: ALCT-IR1, 18 μm vertical box at 25deg.C INSTEC;
K 11 is the torsional elastic constant, K 33 is the splay elastic constant, and the test conditions are: ALCT-IR1, 18 μm vertical box at 25deg.C INSTEC;
delta epsilon represents dielectric anisotropy, delta epsilon = epsilon-epsilon, wherein epsilon is the dielectric constant parallel to the molecular axis, epsilon is the dielectric constant perpendicular to the molecular axis, and the test conditions are: ALCT-IR1, 18 μm vertical box at 25deg.C INSTEC;
Δn represents optical anisotropy, Δn=n o-ne, where n o is the refractive index of ordinary light and n e is the refractive index of extraordinary light, test conditions: 589nm, 25.+ -. 0.2 ℃.
In the invention, the compounds of the general formulas I, II and III are respectively weighed according to the proportion to prepare the liquid crystal medium, wherein equipment and instruments used for preparing the liquid crystal medium are as follows:
(1) Electronic precision balance (precision 0.1 mg);
(2) Stainless steel beaker: for weighing the compound raw materials;
(3) Spoon: for adding raw materials;
(4) Magnetic force rotor: for stirring;
(5) Temperature-controlled electromagnetic stirrer.
The preparation method of the liquid crystal medium comprises the following steps:
(1) The raw materials are orderly placed;
(2) Placing a stainless steel beaker on a balance, and placing the compound of the formula I into the stainless steel beaker by using a small spoon;
(3) Sequentially adding other compound raw materials according to the required weight;
(4) Placing the stainless steel beaker with the materials on a magnetic stirring instrument for heating and melting;
(5) After most of the mixture in the stainless steel beaker is melted, adding a magnetic rotor into the stainless steel beaker, uniformly stirring the liquid crystal mixture, and cooling to room temperature to obtain the liquid crystal medium.
And filling the obtained liquid crystal medium between two substrates of the liquid crystal display for performance test.
The composition ratios and the performance parameters of the liquid crystal media of example 3 are shown in table 2;
TABLE 2
The composition ratios and the performance parameters of the liquid crystal media of example 4 are shown in table 3;
TABLE 3 Table 3
The composition ratios and the performance parameters of the liquid crystal media of example 5 are shown in Table 4;
TABLE 4 Table 4
The component ratios and the performance parameters of the liquid crystal media of example 6 are shown in Table 5;
TABLE 5
The component ratios and the performance parameters of the liquid crystal media of example 7 are shown in Table 6;
TABLE 7
The composition ratio of the liquid crystal medium of example 8 and its performance parameters table 7;
TABLE 7
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The composition ratio of the liquid crystal medium of example 9 and its performance parameters table 8;
TABLE 8
The composition ratio and the performance parameters of the liquid crystal medium of example 10 are shown in Table 9;
TABLE 9
Comparative example 1
The formulation is shown in Table 10 below, and the components do not include a compound of formula I, but include a compound of formula V.
Table 10
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Conclusion: as can be seen from the performance parameters of the liquid crystal compositions of examples 3 to 10, the liquid crystal composition provided by the invention has good intersolubility and large negative dielectric constant, and as can be seen from the comparison of example 10 and comparative example 1, the liquid crystal with alkoxy is replaced by the silyl liquid crystal provided by the invention, and has good intersolubility and low-temperature stability, and has larger negative dielectric constant, so that the intersolubility of the liquid crystal compound can be improved by using the compound shown as the formula I provided by the invention, the application range of the liquid crystal mixture is widened, and the application value is important.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (9)
1. A silicon-containing liquid crystal compound characterized by having any one of the following structures
Wherein V 1、V2 is each independently selected from a single bond, -CH 2O-、-OCH2-、-CH2-、-CH2CH2-、-CF2O-、-OCF2 -, or-COO-;
r 0 is fluorine;
R 2、R3 are the same or different and are each independently selected from the group consisting of methyl and ethyl;
R 1、R4 is the same or different and is each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, propenyl, butenyl, pentyl, pentenyl, methoxy, ethoxy, propoxy, butoxy, propenoxy, butenyloxy, pentoxy, pentenyloxy, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, pentafluoroethyl, cyclopropoxy, cyclobutoxy, cyclopentyloxy or pentafluoroethoxy;
t 1、T2 are each independently selected from the group consisting of a single bond or:
* -and- (x) represents a bond.
2. The liquid crystal on silicon compound of claim 1, wherein R 1、R4 in I-2 are the same or different and are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, propenyl, butenyl, pentyl, pentenyl.
3. The liquid crystal compound containing silicon according to claim 1 or 2, wherein the liquid crystal compound comprises any one of the structures LS01-LS286 shown below:
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4. a liquid-crystalline medium, characterized in that it comprises one or more silicon-containing liquid-crystalline compounds as claimed in any of claims 1 to 3.
5. The liquid-crystalline medium according to claim 4, further comprising one or more compounds of formula II:
Wherein,
Each R 7、R8 is independently selected from the group consisting of the groups defined below A, B, C:
A: a linear alkyl group having C 1-C7 or a linear alkoxy group having C 1-C7;
b: a group formed after one or more of the groups in a are replaced by-CH 2 -, O-, COO-, OOC-, or-ch=ch-;
C: a group formed after one or more hydrogen atoms in any of the groups a are replaced by F, cl, -ch=ch 2, or-ch=ch-CH 3;
Ring B, ring C, ring D, ring E are each independently selected from the group consisting of:
and at least one of the rings B, C, D, E is selected from/> One of the following;
m, n, o are each independently 0 or 1;
each Z 1、Z2、Z3 is independently selected from the group consisting of a single bond, -C 2H4 -, ch=ch-, * -COO-, OOC-, CH 2O-*、*-OCH2-*、*-CF2 O-, and OCF 2 -, wherein any H may be replaced by F;
* -and- (x) indicates the position at which the substituents are bonded.
6. The liquid-crystalline medium according to claim 5, further comprising one or more compounds of formula III:
Wherein,
R 9、R10 is each independently selected from the group consisting of alkyl having C 1-C10 or alkenyl having C 2-C10, wherein any of-CH 2 -may be replaced by-CH 2O-、-OCH2 -,Instead, any H atom may be replaced by F;
Ring F, ring G, ring I, ring J are each independently selected from the group consisting of:
p, q, r are each independently 0 or 1;
Each Z 4、Z5、Z6 is independently selected from the group consisting of a single bond, -C 2H4 -, ch=ch-, * -COO-, OOC-, CH 2O-*、*-OCH2-*、*-CF2 O-, and OCF 2 -, wherein any H may be replaced by F;
* -and- (x) indicates the position at which the substituents are bonded.
7. The liquid crystal medium according to claim 6, wherein the mass percentage of the silicon-containing liquid crystal compound in the liquid crystal medium is 1-24%, the mass percentage of the compound of formula II is 35-58%, and the mass percentage of the compound of formula III is 30-46%.
8. The liquid crystal medium of claim 4, further comprising one or more functional additives; the functional additive comprises an antioxidant, a chiral agent, a light stabilizer or an ultraviolet absorber.
9. Consumer product, characterized in that it comprises a liquid-crystalline medium according to any one of claims 4 to 8.
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