CN114702967A - Novel liquid crystal compound and preparation method and application thereof - Google Patents
Novel liquid crystal compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN114702967A CN114702967A CN202210451647.0A CN202210451647A CN114702967A CN 114702967 A CN114702967 A CN 114702967A CN 202210451647 A CN202210451647 A CN 202210451647A CN 114702967 A CN114702967 A CN 114702967A
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- China
- Prior art keywords
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- liquid crystal
- ring
- independently selected
- crystal compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 67
- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
- -1 trifluoromethoxy, difluoromethoxy Chemical group 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000004405 heteroalkoxy group Chemical group 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 239000013538 functional additive Substances 0.000 claims description 4
- 150000002825 nitriles Chemical class 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 239000006097 ultraviolet radiation absorber Substances 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 1
- 239000000463 material Substances 0.000 abstract description 9
- 230000003287 optical effect Effects 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000034 method Methods 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 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
- 229910052794 bromium Inorganic materials 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
- 238000000605 extraction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 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
- 229910052757 nitrogen Inorganic materials 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 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
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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 group [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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- 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
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 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
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 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
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 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
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000005447 environmental material Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005980 hexynyl group Chemical group 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000006606 n-butoxy group Chemical group 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
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 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
- 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
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 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
- 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
- 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
- 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
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 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
- 238000000926 separation method Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 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
- 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
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
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Abstract
The invention relates to the technical field of liquid crystal materials, in particular to a novel liquid crystal compound and a preparation method and application thereof. The liquid crystal compound has a structure shown as a general formula I; the liquid crystal compound has the characteristics of relatively high vertical dielectric anisotropy, relatively high optical anisotropy, relatively low 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, effectively improves the display quality, and has an important application value.
Description
Technical Field
The invention relates to the technical field of liquid crystal materials, in particular to a novel 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 been developed. Taking a television as an example, the television has the characteristics of light weight, small occupied space, convenience in movement and the like, and is also provided with 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 environmental material. At present, the TFT-LCD product technology has matured, and successfully solves the technical problems of viewing angle, resolution, color saturation, brightness, etc., and large-size and medium-and small-size TFT-LCD displays have gradually occupied the mainstream status of flat panel displays in respective fields. However, the requirements for display technology are continuously increasing, and liquid crystal displays are required to achieve faster response, reduce driving voltage to reduce power consumption, and the like, so that liquid crystal materials are 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 the liquid crystal display, and in order to improve the performance of the material and enable the material to adapt to new requirements, the synthesis of a novel structure liquid crystal compound and the research of the structure-performance relationship become important work in the field of liquid crystal.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The invention aims to provide a liquid crystal compound with a novel 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 applied to the field of liquid crystal display, can achieve the application purposes of low power consumption, wide viewing angle and high contrast, effectively improves the display quality, and has important application value; the invention also aims to provide a preparation method and application of the liquid crystal compound.
Specifically, the invention provides the following technical scheme:
the invention provides a liquid crystal compound, which has a structure shown as a general formula I:
in the formula I, the compound is shown in the specification,
V1、V2each independently selected from a single bond, -CH2-、-CH2CH2-、-CH＝CH-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
R1、R2、R3、R4identical or different, each independently selected from hydrogen, deuterium, fluorine, nitrile groups, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl, aryl having 6 to 80 carbon atoms or heteroaryl having 2 to 60 carbon atoms, R1And R2May be optionally joined or fused and together with the Si to which it is attached form a substituted or unsubstituted ring, with or without one or more additional N, O, S or Si heteroatoms in the ring so formed; and R is1、R2、R3One or more hydrogen atoms in (a) may be optionally substituted with fluorine atoms;
X1represents O or S;
R0is hydrogen or fluorine;
T1selected from the group consisting of single bonds orThe group consisting of:
and represents a bond.
Aryl in the sense of the present invention preferably contains from 6 to 60 carbon atoms and heteroaryl in the sense of the present invention contains from 2 to 60 carbon atoms and at least one heteroatom, with the proviso 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 herein is 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 group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. The hydrogen on the aryl or heteroaryl group forms a substituted aryl or substituted heteroaryl group by simple substitution or substitution, such as fluorobenzene, difluorobenzene, trifluorobenzene, tetrafluorobenzene, cyclohexylbenzene, cyclohexylfluorobenzene, and the like, which is referred to as an aryl or heteroaryl group.
Alkyl, alkenyl or alkynyl groups having 1 to 40 carbon atoms in the sense of the present invention are preferably to be understood as meaning 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. The alkoxy group, preferably an alkoxy group having 1 to 40 carbon atoms, is considered to mean a methoxy group, a trifluoromethoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a n-pentyloxy group, a sec-pentyloxy group, a 2-methylbutyloxy group, a n-hexyloxy group, a cyclohexyloxy group, a n-heptyloxy group, a cycloheptyloxy group, a n-octyloxy group, a cyclooctyloxy group, a 2-ethylhexyloxy group, a pentafluoroethoxy group and a 2,2, 2-trifluoroethoxy group. The heteroalkyl group is preferably an alkyl group having 1 to 40 carbon atoms, meaning a hydrogen atom or-CH alone2The radicals-which may be substituted by oxygen, sulfur or halogen atoms-are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, 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, 2,2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, propenylthio, butenyloxy, cyclohexenylthio, ethynyloxy, Ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, where one or more-CH may be present2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
Preferably, the liquid crystal compound comprises one or more of the structures shown below:
further, the V1、V2Each independently selected from a single bond, -CH2O-、-CH2CH2-、-CF2O-or-COO-.
Further, said R3Selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, trifluoromethyl, trifluoromethoxy, difluoromethoxy, having C1-C7Straight chain alkyl of (2) having C1-C7Group consisting of linear alkoxy groups of (A), R3One of (1)Or a plurality of hydrogen atoms may be substituted by fluorine atoms.
Further, said R4Selected from the group consisting of hydrogen, methyl, ethyl, nitrile groups.
Further, said R1、R2Each, the same or different, is selected from the group consisting of1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Or alkenyl or alkynyl of (A), R1And R2May optionally be joined and form, together with the Si to which they are attached, a substituted or unsubstituted ring, with or without one or more additional N, O, S or Si heteroatoms in the formed ring; at R1、R2One or more hydrogen atoms in (a) may be substituted with fluorine atoms.
Further, said T1Selected from the group consisting of a single bond or the following groups:
and represents a bond.
According to an embodiment of the invention, said R0Is fluorine; x1Is S or O.
According to an embodiment of the invention, said R4Selected from the group consisting of hydrogen, methyl, nitrile groups.
According to an embodiment of the invention, said R3Selected from the group consisting of hydrogen, fluoro, trifluoromethyl, trifluoromethoxy, difluoromethoxy, having C1-C7Straight chain alkyl of (2) having C1-C7Group consisting of linear alkoxy groups of (A), R3One or more hydrogen atoms in (a) may be substituted with fluorine atoms.
According to an embodiment of the present invention, said R1、R2Each, the same or different, is selected from the group consisting of1-C40Straight chain alkyl of (2) having C3-C40A branched or cyclic alkyl group having C2-C40Or alkenyl or alkynyl of (A), R1And R2May optionally be joined and form, together with the Si to which they are attached, a substituted or unsubstituted ring, with or without one or more additional N, O, S or Si heteroatoms in the formed ring; at R1、R2One or more hydrogen atoms in (a) may be substituted with fluorine atoms.
Preferably, R is1、R2Identical or different, each independently selected from the group consisting of methyl, ethyl, propyl, butyl, propenyl, butenyl, or R1And R2Are bonded to each other to form a film having C2～C7An alkylene group of (a).
Preferably, R is4Selected from hydrogen or methyl.
According to an embodiment of the present invention, preferably, the R is1、R2Identical or different, each independently selected from the group consisting of methyl, ethyl, propyl, butyl, or R1And R2Are bonded to each other to form a film having C2～C5An alkylene group of (a).
Preferably, the liquid crystal compound comprises one or more of structures LS01-LS134 shown below:
the present invention also provides a method for preparing the liquid crystal compound described above:
wherein R is0-R3、X1、V1、V2、T1Have the same meaning as defined above; y is1Br, I, Li, OH or OTf; y is2Is Cl, Br, I or OTf.
The raw materials for synthesizing the compound shown in the formula I can be purchased from commercial sources, the method principle, the operation process, the conventional post treatment, the column purification, the recrystallization purification and other means are well known by the synthesis personnel in the field, and the synthesis process can be completely realized to obtain the target product.
The reactions of all the steps of all the above processes 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 which comprises one or more liquid crystal compounds.
Preferably, the liquid-crystalline medium further comprises, as a second component:
wherein, the first and the second end of the pipe are connected with each other,
R7、R8each independently selected from the group consisting of the groups defined by A, B, C:
a: having a structure of C1-C7Has a straight-chain alkyl group or has C1-C7Straight chain alkoxy of (a);
b: one or more-CH in any group in A2A group formed after being substituted by-O-, -COO-, -OOC-, or-CH ═ CH-;
c: one or more hydrogen atoms in any group in A are F, Cl, — CH ═ CH2or-CH ═ CH-CH3Replacing the latter formed group;
ring B, ring C, ring D, ring E are each independently selected from the group consisting of:
m, n, o are each independently 0 or 1;
Z1、Z2、Z3each independently selected from the group consisting of a single bond, — C2H4-*、*-CH＝CH-*、
*-COO-*、*-OOC-*、*-CH2O-*、*-OCH2-*、*-CF2O-and-OCF2Any H may be replaced by F;
-and-indicate the position to which the substituent is bonded;
preferably, the liquid-crystalline medium further comprises one or more compounds of the formula III:
wherein the content of the first and second substances,
R9、R10each independently selected from the group consisting of1-C10Or with C2-C10Wherein any of-CH2Can be-CH2O-、-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;
Z4、Z5、Z6each independently selected from the group consisting of a single bond, — C2H4-*、*-CH＝CH-*、
*-COO-*、*-OOC-*、*-CH2O-*、*-OCH2-*、*-CF2O-and-OCF2Any H may be replaced by F;
and indicates the position to which the substituent is 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 compounds of formula II include compounds represented by the following formulas II-1 to II-15:
wherein the content of the first and second substances,
R7、R8each independently selected from the group consisting of the groups defined by A, B, C:
a: having a structure of C1-C7Has a straight-chain alkyl group or has C1-C7Straight chain alkoxy of (a);
b: one or more-CH in any group in A2A group formed after being substituted by-O-, -COO-, -OOC-, or-CH ═ CH-;
c: one or more hydrogen atoms in any group in A are F, Cl, - (CH-CH ═ CH)2or-CH ═ CH-CH3Replacing the latter formed group;
above ring H1Ring H2Each independently selected from the group consisting of:
further, the compounds of formula III include compounds of formulae III-1 to III-16 below:
wherein R is9、R10Each independently selected from the group consisting of1-C10Or with C2-C10Wherein any of-CH2Can be-CH2O-、-OCH2-、
Instead, any H atom may be replaced by F; (F) each independently represents F or H.
Preferably, the liquid-crystalline 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.
The consumer products include, but are not limited to, flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablets, phablets, Personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays less than 2 inches diagonal, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls containing multiple displays tiled together, theater or sports screens, phototherapy devices, and signs.
Unless otherwise specified, all starting materials for use in the present invention are commercially available and any range recited herein includes any endpoints and any numerical values therebetween and any subranges therebetween.
The invention has the following beneficial effects:
the liquid crystal compound provided by the invention has the chemical main structure of dibenzothiophene or dibenzofuran, the dielectric anisotropy of the structure is larger, and a six-membered ring structure containing silicon atoms is introduced into 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, and meanwhile, the clearing point is obviously improved, the optical anisotropy is higher, the moderate rotational viscosity and the liquid crystal intersolubility are realized, the low-temperature working effect is excellent, and the performances in the aspects of good thermal stability, chemical stability, optical stability, mechanics and the like are realized; 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 provided by the invention 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 liquid crystal mixtures and have important application value.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The examples do not show the specific techniques or conditions, according to the technical or conditions described in the literature in the field, or according to the product specifications. The reagents or instruments used are conventional products available from regular distributors, not indicated by the manufacturer.
In the present invention, the preparation methods are all conventional methods unless otherwise specified. The starting materials used are available from published commercial sources unless otherwise specified, and the percentages are by mass unless otherwise specified. The novel liquid crystal compounds provided by the present invention all reactions are carried out under well-known suitable conditions, and some involve simple organic preparations, for example, the preparation of phenylboronic acid can be synthesized by skilled operating skills, and are not described in detail in the present invention.
Example 1
Preparation of compound LS 15:
under the protection of nitrogen, 20.0mmol of 4, 6-difluoro-7-propoxybenzene [ b, d ] thiophene-3-phenol (reactant 1) is dissolved in 50mL of DMF, 24.0mmol of 4-chloromethyl-1, 1-dimethyl-methylcyclohexane (reactant 2) and 40.0mmol of anhydrous potassium carbonate are added, the temperature is increased to 80 ℃, the reaction is stirred and reacted for 12 hours, the temperature is reduced to room temperature, the reaction solution is poured into 250mL of ice water, ethyl acetate is used for extraction, an organic phase is collected, drying and filtering are carried out, filtrate is concentrated under reduced pressure to dryness, silica gel column separation and purification and ethanol recrystallization are carried out to obtain a white solid, and the yield: 84%, HRMS, m/z: 435.1563[ M + H ].
Example 2
Preparation of compound LS 27:
under the protection of nitrogen, 20.0mmol of 7-cyclopentanemethoxy-4, 6-difluorodibenzo [ b, d ] thiophen-3-ol is dissolved in 50mL of DMF, 40.0mmol of anhydrous cesium carbonate and 24.0mmol of 9-chloromethyl-5-silaspiro [4.5] decane are added, the temperature is raised to 80 ℃, the reaction is stirred for 12 hours, the mixture is cooled to the room temperature, 250mL of ice water is added, dichloromethane is used for extraction, the organic phase is collected and washed by saturated salt water, the organic phase is dried, filtered, the filtrate is concentrated under reduced pressure and dried, separated and purified by a silica gel column, and ethanol is recrystallized to obtain a compound LS27, a white solid, and the yield: 90%, HRMS, m/z: 501.2029[ M + H ].
Example 3
Preparation of compound LS 71:
20.0mmol of 7- ((4-ethylcyclohexyl) methoxy) -4, 6-difluorodibenzo [ b, d ] furan-3-ol is dissolved in 80mL of acetone, 40.0mmol of anhydrous potassium carbonate and 24.0mmol of 4-chloromethyl-1-ethyl-1-methylsilacylcyclohexane are added, the mixture is heated to reflux and stirred for reaction for 12 hours, the mixture is cooled to room temperature and filtered, the filtrate is concentrated under reduced pressure and dried, separated and purified by a silica gel column and recrystallized by ethanol to obtain a white solid, and the yield is as follows: 88%, HRMS, m/z: 514.2703[ M + ].
Referring to the similar synthetic methods of the above examples 1 to 3, liquid crystal compounds shown in the following table 1 were prepared:
TABLE 1
Examples of mixtures
Examples 8 to 15:
examples 8 to 15 show the preparation methods of different liquid crystal media, wherein the monomer structures, the amounts (weight percentage) of the specific compounds of each example, and the results of the performance parameter tests of the obtained liquid crystal media are respectively shown in the following tables 8 to 15.
The temperature units referred to in the examples are, and the specific meanings and test conditions for the other symbols are as follows:
p. shows the clearing point (. degree. C.) of the liquid crystal, the test apparatus: a Mettler-Toledo-FP System micro thermal analyzer;
γ 1 is rotational viscosity (mPa · s) and the test conditions are: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
K11is a torsional elastic constant, K33For the splay spring constant, the test conditions were: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
Δ ∈ denotes dielectric anisotropy, Δ ∈/∈ where ∈/is the dielectric constant parallel to the molecular axis, ∈ ×) is the dielectric constant perpendicular to the molecular axis, test conditions: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
Δ n represents optical anisotropy, and Δ n ═ no-neWherein n isoRefractive index of ordinary light, neFor the refractive index of extraordinary rays, test conditions: 589nm, 25 + -0.2 deg.C.
In the invention, compounds of general formulas I, II and III are weighed according to the proportion respectively to prepare the liquid crystal medium, wherein the equipment and the instrument 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) a magnetic rotor: is used for stirring;
(5) and (5) controlling the temperature of the electromagnetic stirrer.
The preparation method of the liquid crystal medium comprises the following steps:
(1) the raw materials are orderly placed;
(2) placing the stainless steel beaker on a balance, and placing the compound of formula I into the stainless steel beaker with a small spoon;
(3) sequentially adding other compound raw materials according to the required weight;
(4) placing the stainless steel beaker added with the materials on a magnetic stirring instrument for heating and melting;
(5) and 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 component ratios and their performance parameters of the liquid-crystalline medium of example 8 are given in Table 3;
TABLE 3
Table 4 sets forth the component ratios and performance parameters for the liquid-crystalline media of example 9;
TABLE 4
Table 5 shows the component ratios and their performance parameters of the liquid-crystalline medium of example 10;
TABLE 5
Table 6 for the component ratios and their performance parameters of the liquid-crystalline medium of example 11;
TABLE 6
Table 7 for the component ratios and their performance parameters of the liquid-crystalline medium of example 12;
TABLE 7
Table 8 shows the component ratios and their performance parameters of the liquid-crystalline medium of example 13;
TABLE 8
Table 9 sets forth the component ratios and performance parameters for the liquid-crystalline media of example 14;
TABLE 9
Table 10 for the component ratios and their performance parameters of the liquid-crystalline medium of example 15;
watch 10
Comparative example 1
The formulation is shown in the following table 11, and the components thereof do not contain the compound of formula I, but contain the compound of formula V.
TABLE 11
And (4) conclusion: from the performance parameters of the liquid crystal compositions of the embodiments 8 to 15, the liquid crystal composition provided by the invention has good intersolubility and a larger negative dielectric constant, and from the comparison between the embodiment 13 and the comparative example 1, the liquid crystal of cyclohexane or pyran shows good intersolubility and low-temperature stability after being replaced by the liquid crystal of silacyclohexane, and has a larger negative dielectric constant, so that the compound shown in the formula I provided by the invention can improve the intersolubility of the liquid crystal compound, expand the application range of the liquid crystal mixture, and has an important application value.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A liquid crystal compound having a structure represented by formula I:
in the formula I, the compound is shown in the specification,
V1、V2each independently selected from a single bond, -CH2-、-CH2CH2-、-CH＝CH-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
R1、R2、R3、R4identical or different, each independently selected from hydrogen, deuterium, fluorine, nitrile group, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has a branched or cyclic heteroalkoxy group of C2-C40Alkenyl or alkynyl of (A), having C6-C80Or have C2-C60Of R, R1And R2May be optionally joined or fused and together with the Si to which it is attached form a substituted or unsubstituted ring, with or without one or more additional N, O, S or Si heteroatoms in the ring so formed; and R is1、R2、R3One or more hydrogen atoms in (a) may be optionally substituted with fluorine atoms;
X1represents O or S;
R0is hydrogen or fluorine;
T1selected from the group consisting of a single bond or the following groups:
and represents a bond.
2. The liquid crystal compound of claim 1, comprising one or more of the following structures:
wherein, V1、V2Each independently selected from a single bond, -CH2O-、-CH2CH2-、-CF2O-or-COO-;
R4selected from the group consisting of hydrogen, methyl, ethyl, nitrile;
R3selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, trifluoromethyl, trifluoromethoxy, difluoromethoxy, having C1-C7Straight chain alkyl of (2) having C1-C7Group consisting of linear alkoxy groups of (A), R3One or more hydrogen atoms in (a) may be substituted with fluorine atoms;
R1、R2each, the same or different, is selected from the group consisting of1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or C of2-C40Alkynyl of (a), R1And R2May 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 formed ring; at R1、R2One or more hydrogen atoms in (a) may be substituted with fluorine atoms;
T1selected from the group consisting of a single bond or the following groups:
and represents a bond.
3. The liquid crystal compound according to claim 1 or 2, wherein R is0Is fluorine;
R4selected from the group consisting of hydrogen, methyl, nitrile;
R3selected from the group consisting of hydrogen, fluoro, trifluoromethyl, trifluoromethoxy, difluoromethoxy, having C1-C7Straight chain alkyl of (2) having C1-C7Group consisting of linear alkoxy groups of (A), R3One or more hydrogen atoms in (a) may be substituted with fluorine atoms;
R1、R2each, the same or different, is selected from the group consisting of having C1-C40Straight chain alkyl of (2) having C3-C40A branched or cyclic alkyl group having C2-C40Or alkenyl or alkynyl of (A), R1And R2May optionally be joined and form, together with the Si to which they are attached, a substituted or unsubstituted ring, with or without one or more additional N, O, S or Si heteroatoms in the formed ring; at R1、R2One or more hydrogen atoms in (a) may be substituted with fluorine atoms.
4. The liquid crystal compound according to any one of claims 1 to 3, wherein R is1、R2Identical or different, each independently selected from the group consisting of methyl, ethyl, propyl, butyl, propenyl, butenyl, or R1And R2Are bonded to each other to form a film having C2～C7An alkylene group of (a);
R4selected from hydrogen or methyl.
5. The liquid crystal compound according to claim 4, wherein R is1、R2Identical or different, each independently selected from the group consisting of methyl, ethyl, propyl, butyl, or R1And R2Are bonded to each other to form a film having C2～C5An alkylene group of (a).
6. The liquid crystal compound of any one of claims 1-5, wherein the liquid crystal compound comprises one or more of structures LS01-LS134 shown below:
7. a liquid-crystalline medium, characterized in that it comprises one or more liquid-crystalline compounds according to any one of claims 1 to 6;
preferably, the liquid-crystalline medium further comprises one or more compounds of the formula II:
wherein the content of the first and second substances,
R7、R8each independently selected from the group consisting of those defined by A, B, C below:
a: having a structure of C1-C7Has a straight-chain alkyl group or has C1-C7Straight chain alkoxy of (a);
b: one or more-CH in any of groups in said A2A group formed after being substituted by-O-, -COO-, -OOC-, or-CH ═ CH-;
c: one or more hydrogen atoms in any group in A are F, Cl, - (CH-CH ═ CH)2or-CH3Replacing the latter formed group;
ring B, ring C, ring D, ring E are each independently selected from the group consisting of:
m, n, o are each independently 0 or 1;
Z1、Z2、Z3each independently selected from the group consisting of a single bond, — C2H4-*、*-CH＝CH-*、
*-COO-*、*-OOC-*、*-CH2O-*、*-OCH2-*、*-CF2O-and-OCF2Any H may be replaced by F;
-and-indicate the position to which the substituents are bonded;
more preferably, the liquid-crystalline medium further comprises one or more compounds of formula III:
wherein the content of the first and second substances,
R9、R10each independently selected from the group consisting of1-C10Or with C2-C10Wherein any of-CH2Can be-CH2O-、-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;
Z4、Z5、Z6each independently selected from the group consisting of a single bond, — C2H4-*、*-CH＝CH-*、
*-COO-*、*-OOC-*、*-CH2O-*、*-OCH2-*、*-CF2O-and-OCF2Any H may be replaced by F;
and indicates the position to which the substituent is bonded.
8. The liquid crystal medium of claim 7, wherein the liquid crystal compound is present in an amount of 1-24% by weight, the compound of formula II is present in an amount of 35-58% by weight, and the compound of formula III is present in an amount of 30-46% by weight.
9. Liquid-crystalline medium according to claim 7 or 8, characterized in that it further comprises one or more functional additives; the functional additive comprises an antioxidant, a chiral agent, a light stabilizer or an ultraviolet absorber.
10. A consumer product, characterized in that it comprises a liquid-crystalline medium according to any one of claims 7 to 9.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1129581A (en) * | 1997-07-11 | 1999-02-02 | Chisso Corp | Liquid crystal compound with negative permitivity anisotropy value, liquid crystal composition containing the liquid crystal compound, and liquid crystal display element using the liquid crystal compound |
| US20050258396A1 (en) * | 2002-06-28 | 2005-11-24 | Qinetiq Limited | Potochromic liquid crystals |
| US20080230745A1 (en) * | 2007-03-23 | 2008-09-25 | Michael Wand | Liquid crystal compound, ferroelectric liquid crystal composition, and ferroelectric liquid crystal display |
| US20140160384A1 (en) * | 2012-09-10 | 2014-06-12 | Wenlei Li | Smectic a-phase liquid crystal material |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1129581A (en) * | 1997-07-11 | 1999-02-02 | Chisso Corp | Liquid crystal compound with negative permitivity anisotropy value, liquid crystal composition containing the liquid crystal compound, and liquid crystal display element using the liquid crystal compound |
| US20050258396A1 (en) * | 2002-06-28 | 2005-11-24 | Qinetiq Limited | Potochromic liquid crystals |
| US20080230745A1 (en) * | 2007-03-23 | 2008-09-25 | Michael Wand | Liquid crystal compound, ferroelectric liquid crystal composition, and ferroelectric liquid crystal display |
| US20140160384A1 (en) * | 2012-09-10 | 2014-06-12 | Wenlei Li | Smectic a-phase liquid crystal material |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116496795A (en) * | 2022-11-17 | 2023-07-28 | Tcl华星光电技术有限公司 | Liquid crystal composition and liquid crystal display panel |
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