CN110760313A - Liquid crystal compound, liquid crystal composition, liquid crystal display element and liquid crystal display - Google Patents
Liquid crystal compound, liquid crystal composition, liquid crystal display element and liquid crystal display Download PDFInfo
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- CN110760313A CN110760313A CN201810837437.9A CN201810837437A CN110760313A CN 110760313 A CN110760313 A CN 110760313A CN 201810837437 A CN201810837437 A CN 201810837437A CN 110760313 A CN110760313 A CN 110760313A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 243
- 150000001875 compounds Chemical class 0.000 title claims abstract description 166
- 239000000203 mixture Substances 0.000 title claims abstract description 159
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 39
- 125000004979 cyclopentylene group Chemical group 0.000 claims abstract description 27
- 125000004980 cyclopropylene group Chemical group 0.000 claims abstract description 27
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 238000006467 substitution reaction Methods 0.000 claims abstract description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 12
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 11
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 89
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005725 cyclohexenylene group Chemical group 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000000875 corresponding effect Effects 0.000 description 42
- 238000009472 formulation Methods 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000002834 transmittance Methods 0.000 description 18
- -1 methylcyclopropylidene Chemical group 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 5
- 238000005265 energy consumption Methods 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- OEPBVXQEVBURGC-UHFFFAOYSA-N 4-bromo-2-fluoro-1-(trifluoromethyl)benzene Chemical compound FC1=CC(Br)=CC=C1C(F)(F)F OEPBVXQEVBURGC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LKOXSLOIMSYWPK-UHFFFAOYSA-N (3-propylcyclopentyl)methanol Chemical compound CCCC1CCC(CO)C1 LKOXSLOIMSYWPK-UHFFFAOYSA-N 0.000 description 1
- RPEPGIOVXBBUMJ-UHFFFAOYSA-N 2,3-difluorophenol Chemical compound OC1=CC=CC(F)=C1F RPEPGIOVXBBUMJ-UHFFFAOYSA-N 0.000 description 1
- SBSFDYRKNUCGBZ-UHFFFAOYSA-N 4-bromo-2-fluoro-1-(trifluoromethoxy)benzene Chemical compound FC1=CC(Br)=CC=C1OC(F)(F)F SBSFDYRKNUCGBZ-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
Abstract
The invention relates to a liquid crystal compound, a liquid crystal composition, a liquid crystal display device and a liquid crystal display. The liquid crystal compound of the invention is a liquid crystal compound shown in the following formula I,
in the formula I, R represents more than one-CH in cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene; y represents-OCF3、‑CF3、‑CF2H or-OCF2H; z represents a single bond, -CH2O‑、‑CF2O-or-COO-;
to represent
Description
Technical Field
The invention belongs to the field of liquid crystal compounds. More particularly, it relates to a liquid crystal compound, a liquid crystal composition, a liquid crystal display element, and a liquid crystal display.
Background
The transmittance of the TFT-LCD panel refers to the ratio of the light intensity before and after the backlight transmits through the TFT-LCD panel. The TFT-LCD is a low-efficiency device with the transmittance of only 3% -10%, when the brightness of the backlight source is 100, most of light incident from the backlight source passes through each layer of the panel, and the brightness of the light finally passing through the panel is only 5, namely the transmittance is only 5%, and only a small part of light can be effectively utilized and captured by human eyes. If the transmittance of the liquid crystal composition can be improved, the transmittance of the TFT-LCD panel can be effectively increased, so that more light can be effectively utilized; on the other hand, the backlight intensity can be reduced, so that the purpose of saving energy consumption is achieved, and the service life of the equipment is prolonged.
In addition, in order to cope with the problems of display image sticking and tailing existing in the application of moving picture display, the liquid crystal display device is required to have a fast response speed, and thus the liquid crystal composition is required to have a low rotational viscosity γ 1. In addition, the response speed of the liquid crystal composition after electrification is directly related to the viscosity of the liquid crystal composition, particularly the rotational viscosity γ 1.
Disclosure of Invention
The present inventors have conducted extensive studies to obtain a liquid crystal compound and a liquid crystal composition for liquid crystal display having improved transmittance and reduced rotational viscosity, and have found that the object can be achieved by the liquid crystal compound and the liquid crystal composition of the present invention, and have completed the present invention.
An object of the present invention is to provide a liquid crystal compound.
Another object of the present invention is to provide a liquid crystal composition containing the above liquid crystal compound.
It is a further object of the present invention to provide a further liquid crystal composition.
The invention also provides a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition.
A liquid crystal compound according to one aspect of the present invention is a liquid crystal compound represented by formula I below:
wherein:
r represents-CH (-CH) of more than one of cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
y represents-OCF3、-CF3、-CF2H or-OCF2H；
Z represents a single bond, -CH2O-、-CF2O-or-COO-;
n represents 0 or 1.
A liquid crystal composition according to an embodiment of the present invention contains the liquid crystal compound according to an embodiment of the present invention.
As a further embodiment of the present invention, a liquid crystal composition comprising one or more compounds represented by the formula II, one or more compounds represented by the formula III, and one or more compounds represented by the formula IV,
wherein the content of the first and second substances,
in the formula II, R' represents more than one-CH in cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
y' represents-F, -OCF3、-CF3、-CF2H or-OCF2H；
Z1Represents a single bond, -CH2O-、-CF2O-or-COO-;
n1Represents 0 or 1;
in the formula III, R1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R1Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
Z2Represents a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
X1、X2each independently represents H or F; x3Represents H, F or methyl;
Y1represents-F, -CF3、-OCF3、-OCF2H or-OCH2F；
m represents 0, 1 or 2;
in the formula IV, R2、R3Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
A liquid crystal display element or a liquid crystal display as another aspect of the present invention includes the aforementioned liquid crystal composition, and the liquid crystal display element or the liquid crystal display is an active matrix display element or a display, a passive matrix display element or a display.
The compound shown in the formula I and the compound shown in the formula II have the characteristics of large vertical dielectric constant, low rotational viscosity and high solubility. In addition, the compound shown in the formula I and the compound shown in the formula II have the characteristics of low rotational viscosity and good intersolubility with other compounds. The lower rotational viscosity is more favorable for improving the response speed of the liquid crystal composition. By adopting the liquid crystal compounds shown in the formula I and the formula II in the liquid crystal composition, the large vertical dielectric constant of the liquid crystal compound can be utilized to be beneficial to improving the transmittance of the liquid crystal composition, so that the transmittance of a liquid crystal display element or a liquid crystal display can be improved, more backlight penetrates through the liquid crystal display element or the liquid crystal display, the backlight utilization rate is improved, the brightness of the liquid crystal display element or the liquid crystal display is improved, the energy consumption is reduced, and the purposes of saving energy and reducing consumption are achieved.
Detailed Description
A. Liquid crystal compounds
The liquid crystal compound as one embodiment of the present invention is a liquid crystal compound represented by the following formula I:
wherein:
r represents-CH (-CH) of more than one of cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
y represents-OCF3、-CF3、-CF2H or-OCF2H；
Z represents a single bond, -CH2O-、-CF2O-or-COO-;
n represents 0 or 1.
The liquid crystal compound shown in the formula I has a dibenzofuran structure, and the structure comprises two fluorine atoms and one oxygen atom which provide a large vertical dielectric constant for the liquid crystal compound. Because the fluorine atom contained in the dibenzofuran structure forms an included angle with the long axis direction of the liquid crystal compound, the dielectric anisotropy formed by the fluorine atom can be decomposed into a parallel dielectric constant and a vertical dielectric constant which are parallel to and vertical to the long axis direction of the liquid crystal compound. Because the parallel dielectric constants generated by the two fluorine atoms are opposite in direction and equal in size, the fluorine atoms do not improve the parallel dielectric constant of the liquid crystal compound, but only improve the vertical dielectric constant of the liquid crystal compound. Further, oxygen atoms have a dielectric anisotropy component only in a direction perpendicular to the long axis of the liquid crystal compound. The Y group as a terminal group provides a liquid crystal compound with a large parallel dielectric constant, and the absolute value of the Y group is similar to the vertical dielectric constant provided by fluorine atoms and oxygen atoms. The R group reduces the symmetry of the liquid crystal compound, forms an irregular structure, prevents the liquid crystal compound from forming a regular crystal structure, is beneficial to keeping the liquid crystal state of the liquid crystal compound and effectively improves the clearing point of the liquid crystal compound. Therefore, the compound represented by formula I has a small absolute value of dielectric anisotropy and is close to neutral, but has the characteristics of a large perpendicular dielectric constant, a low rotational viscosity, and a high solubility. By adopting the liquid crystal compound in the liquid crystal composition, the large vertical dielectric constant of the liquid crystal compound can be utilized, so that the transmittance of the liquid crystal composition is improved, the transmittance of a liquid crystal display element or a liquid crystal display can be improved, more backlight penetrates through the liquid crystal display element or the liquid crystal display, the backlight utilization rate is improved, the brightness of the liquid crystal display element or the liquid crystal display is improved, the energy consumption is reduced, and the purposes of saving energy and reducing consumption are achieved. In addition, the compound shown in the formula I has the characteristics of low rotational viscosity and good intersolubility with other compounds. The lower rotational viscosity is more favorable for improving the response speed of the liquid crystal composition.
In the liquid crystal composition represented by the formula I, R represents-CH (CH-CH) of more than one of cyclopropyl, cyclopentyl and alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene. One or more-CH in C2-10 alkyl group2Examples of the group substituted with cyclopropylene or cyclopentylene include methylcyclopropylidene, ethylcyclopropylene, propylcyclopropylene, isopropylcyclopropylidene, n-butylcyclopropylidene, isobutylcyclopropylidene, t-butylcyclopropylidene, methylcyclopentylene, ethylcyclopentylene, propylcyclopentylene, isopropylidenePropylcyclopentylene, n-butylcyclopentylene, isobutylcyclopentylene, and the like. Among the groups represented by R, preferred is cyclopropyl or cyclopentyl from the viewpoints of rotational viscosity, solubility and clearing point of the liquid crystal compound. Among the linking groups represented by Z, -CH is preferred2O-，-CH2O-to a single bond, -CF2O-or-COO-can provide a liquid crystal compound with a larger vertical dielectric constant.
Optionally, the liquid crystal compound represented by the formula I is selected from the group consisting of compounds represented by the formulae I1 to I32,
wherein:
r represents-CH (-CH) of more than one of cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
In one embodiment of the present invention, among the compounds represented by the above formula I, preferably, the compounds represented by the formula I are selected from the group consisting of compounds represented by the following chemical formulae,
the compound represented by the formula I can be produced by the methods shown in examples described below and by using known alternative reactions and starting materials compatible with the target substance in these methods.
B. Liquid crystal composition
A liquid crystal composition according to an embodiment of the present invention contains the liquid crystal compound represented by the formula I. The liquid crystal composition may contain a liquid crystal compound other than the liquid crystal compound represented by formula I and other additive materials in addition to the compound represented by formula I. By containing the liquid crystal compound shown in the formula I in the liquid crystal composition, the large vertical dielectric constant of the liquid crystal compound can be utilized, so that the transmittance of the liquid crystal composition is improved, more backlight penetrates through a liquid crystal display element or a liquid crystal display, and the backlight utilization rate is improved. In addition, the compound shown in the formula I has the characteristics of low rotational viscosity and good intersolubility with other compounds. The lower rotational viscosity is more favorable for improving the response speed of the liquid crystal composition.
C. Liquid crystal composition
As a further embodiment of the present invention, a liquid crystal composition comprising one or more compounds represented by the formula II, one or more compounds represented by the formula III, and one or more compounds represented by the formula IV,
wherein the content of the first and second substances,
in the formula II, R' represents more than one-CH in cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
y' represents-F, -OCF3、-CF3、-CF2H or-OCF2H；
Z1represents-CH2O-、-CF2O-or-COO-;
to represent
n1Represents 0 or 1;
in the formula III, R1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, R1Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
Z2Represents a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
X1、X2each independently represents H or F; x3Represents H, F or methyl;
Y1represents-F, -CF3、-OCF3、-OCF2H or-OCH2F；
m represents 0, 1 or 2;
in the formula IV, R2、R3Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
In the liquid crystal composition of the aforementioned further embodiment of the present invention, the liquid crystal compound represented by formula II has a dibenzofuran structure, which contains two fluorine atoms and one oxygen atom to provide a liquid crystal compound with a large vertical dielectric constant. Because the fluorine atom contained in the dibenzofuran structure forms an included angle with the long axis direction of the liquid crystal compound, the dielectric anisotropy formed by the fluorine atom can be decomposed into a parallel dielectric constant and a vertical dielectric constant which are parallel to and vertical to the long axis direction of the liquid crystal compound. Because the parallel dielectric constants generated by the two fluorine atoms are opposite in direction and equal in size, the fluorine atoms do not improve the parallel dielectric constant of the liquid crystal compound, but only improve the vertical dielectric constant of the liquid crystal compound. Further, oxygen atoms have a dielectric anisotropy component only in a direction perpendicular to the long axis of the liquid crystal compound. The Y' group as a terminal group provides a liquid crystal compound with a large parallel dielectric constant, which has an absolute value close to the perpendicular dielectric constant provided by fluorine atoms and oxygen atoms. The R' group reduces the symmetry of the liquid crystal compound, forms an irregular structure, prevents the liquid crystal compound from forming a regular crystal structure, is beneficial to keeping the liquid crystal state of the liquid crystal compound and effectively improves the clearing point of the liquid crystal compound. Therefore, the liquid crystal compound represented by formula II has a small absolute value of dielectric anisotropy and is close to neutral, but has characteristics of a large vertical dielectric constant, a low rotational viscosity, and a high solubility. By adopting the liquid crystal compound shown in the formula II in the liquid crystal composition, the large vertical dielectric constant of the liquid crystal compound can be utilized to be beneficial to improving the transmittance of the liquid crystal composition, so that the transmittance of a liquid crystal display element or a liquid crystal display can be improved, more backlight penetrates through the liquid crystal display element or the liquid crystal display, the backlight utilization rate is improved, the brightness of the liquid crystal display element or the liquid crystal display is improved, the energy consumption is reduced, and the purposes of saving energy and reducing consumption are achieved. In addition, the compound shown in the formula II has the characteristics of low rotational viscosity and good intersolubility with other compounds. The lower rotational viscosity is more favorable for improving the response speed of the liquid crystal composition.
The compound shown in the formula III is positive in dielectric anisotropy, and the driving voltage of the liquid crystal composition is adjusted by the compound shown in the formula III.
The content of the compound shown in the formula II in the total mass percent of the liquid crystal composition is 1-15%, preferably 2-10%; the compound shown in the formula III accounts for 1-60% of the total mass of the liquid crystal composition, preferably 10-50%; the content of the compound shown in the formula IV in the total mass percent of the liquid crystal composition is 10-70%, preferably 20-60%.
In the liquid crystal composition represented by the formula II, R' represents-CH which is one or more of cyclopropyl, cyclopentyl and alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene. One or more-CH in C2-10 alkyl group2Examples of the group substituted with a cyclopropylene group or a cyclopentylene group include a methylcyclopropylidene group, an ethylcyclopropylidene group, a propylcyclopropylidene group, an isopropylcyclopropylidene group, an n-butylcyclopropylidene group, an isobutylcyclopropylidene group, a tert-butylcyclopropylidene group, a methylcyclopentylidene group, an ethylcyclopentylidene group, a propylcyclopentylidene group, an isopropylcyclopentylidene group, an n-butylcyclopentylidene group and an isobutylcyclopentylidene group. Among the groups represented by R', preferred is cyclopropyl or cyclopentyl from the viewpoint of the rotational viscosity, solubility and clearing point of the liquid crystal compound. Z1Among the linking groups represented, the preferred one is-CH2O-，-CH2O-is relative to a single bond,-CF2O-or-COO-can provide a liquid crystal compound with a larger vertical dielectric constant.
As Y in the liquid crystal compound represented by the aforementioned formula II1The group represented is preferably-CF in view of increasing the parallel dielectric constant to bring the absolute value of the dielectric anisotropy of the liquid crystal compound close to zero and increasing the clearing point of the liquid crystal compound3、-OCF3、-OCF2H or-OCH2F。
Optionally, the one or more compounds of formula II are selected from the group consisting of compounds of formulae II1-II 40, the one or more compounds of formula III are selected from the group consisting of compounds of formulae III1-III27, and the one or more compounds of formula IV are selected from the group consisting of compounds of formulae IV 1-IV 16.
Wherein the content of the first and second substances,
r 'in the formulae II1 to II 40 is the same as R' in the compound represented by the formula II, and each independently represents-CH which is one or more of cyclopropyl, cyclopentyl and alkyl having 2 to 10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
of formulae II 16-II 30, II 36-II 40
With respect to the aforementioned compound represented by the formula IIAre identical in meaning and each independently represents 
R in the formulae III1 to III271With R in the aforementioned compound of formula III1Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R1Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
(F) in the formulae III1 to III6 each independently represents H or F.
Preferably, the one or more compounds of formula II are selected from the group consisting of compounds of the following formulae,
as another embodiment of the liquid crystal composition of the present invention, one or more compounds represented by formula v may be further included:
wherein:
R4、R5each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
each independently represent
r represents 2 or 3.
Optionally, the one or more compounds of formula V are selected from the group consisting of compounds of formulae V1-V10,
wherein the content of the first and second substances,
R41represents an alkyl group having 2 to 6 carbon atoms, R42Represents an alkenyl group having 2 to 6 carbon atoms, R51Represents an alkyl group having 1 to 6 carbon atoms, R52Represents an alkoxy group having 1 to 6 carbon atoms;
R43、R53each independently represents an alkyl group having 1 to 6 carbon atoms.
The compounds of the formulae V1 to V6 have relatively high clearing points and elastic constants, in particular the splay elastic constant K33It is beneficial to improving the reliability and response speed of the liquid crystal composition.
In the case of compounds of the group consisting of the compounds of the formulae V1 to V6 mentioned above, the compounds of the formulae
The total content of the compounds V1-V6 accounts for 1-40% of the total mass of the liquid crystal composition, and preferably 5-25%.
The compounds shown in the formulas V7-V10 have higher clearing points compared with the compounds shown in the formulas V1-V6, generally higher than 200 ℃, and the clearing points of the liquid crystal composition can be improved more remarkably.
In the case of compounds of the group consisting of the compounds of the formulae V7 to V10 mentioned above, the total amount of the compounds of the formulae V7 to V10 mentioned above is from 1 to 20%, preferably from 5 to 15%, by weight based on the total liquid-crystal composition.
In one embodiment, the liquid crystal composition according to still another embodiment of the present invention may further comprise one or more compounds represented by formula vi:
wherein the content of the first and second substances,
R6、R7each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyl group having 2 to 10 carbon atoms3-8 alkenyloxy, said R6、R7Any one or more of the radicals indicated being unconnected-CH2-optionally each independently substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z3represents a single bond, -CF2O-、-CH2CH2-or-CH2O-；Z4Represents a single bond, -CH2CH2-or-CH2O-；
p represents 1 or 2;
q represents 0, 1 or 2.
The compound shown in the formula VI has larger vertical dielectric constant, the vertical dielectric constant of the liquid crystal composition can be adjusted according to different use conditions, the liquid crystal composition can keep low rotational viscosity, so that the vertical dielectric constant of the liquid crystal composition is further improved on the premise of slightly sacrificing the response speed, and the liquid crystal composition with improved transmittance on the basis of maintaining a certain response speed is obtained.
In the case of compounds of the group consisting of the compounds of the formula VI mentioned above, the proportion of the compound or compounds of the formula VI in the liquid-crystal composition is from 1 to 30% by mass, preferably from 10 to 25% by mass, based on the total mass of the liquid-crystal composition.
Optionally, one or more of the compounds shown in the formula VI is selected from the group consisting of compounds shown in formulas VI 1 to VI 21,
wherein the content of the first and second substances,
R6、R7each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, wherein R is6、R7Any one or more of the radicals indicated being unconnected-CH2-optionally each independently substituted with cyclopentylene, cyclobutyl or cyclopropylene.
As a further embodiment of the liquid crystal composition of the present invention, in one embodiment, optionally, one or more compounds represented by formula vii:
wherein R is8、R9Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R8、R9Any one or more-CH of the groups shown2-optionally each independently substituted with cyclopentylene, cyclobutyl or cyclopropylene;
x represents O, S or CH2O。
Compared with the compound shown in the formula VI, the compound shown in the formula VII has larger vertical dielectric, and the larger vertical dielectric can be obtained by adding a small amount of the compound shown in the formula VII, which is favorable for further improving the transmittance of the liquid crystal composition.
In the case of containing the compound represented by the above formula VII, the content of the above-mentioned one or more compounds represented by the above formula VII is 1 to 15%, preferably 2 to 10% by mass based on the total mass of the liquid crystal composition.
Optionally, the one or more compounds of formula VII are selected from the group consisting of compounds of formulae VII 1 to VII 6,
wherein R is101Each independently represents an alkyl group having 2 to 6 carbon atoms.
D. The liquid crystal display element or the liquid crystal display comprises the liquid crystal composition, and the liquid crystal display element or the liquid crystal display is an active matrix display element or a display, a passive matrix display element or a display.
Optionally, the liquid crystal display element or liquid crystal display is preferably an active matrix addressed liquid crystal display element or liquid crystal display.
Optionally, the active matrix display element or display is specifically a TN-TFT or IPS-TFT liquid crystal display element or display.
The liquid crystal display element or the liquid crystal display has the characteristics of high transmittance and high response speed by containing the liquid crystal composition, and can effectively reduce backlight energy consumption.
Examples
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method if no special description is provided, the used raw materials can be obtained from a public commercial way if no special description is provided, the percentages refer to mass percentage, the temperature is centigrade (DEG C), the liquid crystal compound also becomes a liquid crystal monomer, and the specific meanings and test conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
Δ n represents optical anisotropy, and Δ n ═ ne-noWherein n isoRefractive index of ordinary light, neThe refractive index of the extraordinary ray is measured under the conditions of 25 +/-2 ℃ and 589nm, and the Abbe refractometer is used for testing;
Δ ε represents the dielectric anisotropy, Δ ε/ε ⊥, where ε/is the dielectric constant parallel to the molecular axis, ε ⊥ is the dielectric constant perpendicular to the molecular axis, the test conditions were 25. + -. 0.5 ℃, 20 μm parallel box, INSTEC: ALCT-IR1 test;
γ 1 represents rotational viscosity (mPa. multidot.s) at 25. + -. 0.5 ℃ in a 20 μm parallel cell INSTEC: ALCT-IR1 test;
the equipment and equipment used for preparing the liquid crystal composition were:
(1) electronic precision balance (precision 0.1mg)
(2) Stainless steel beaker: for weighing liquid crystal monomers
(3) Spoon: for adding liquid crystal monomers
(4) A magnetic rotor: for stirring
(5) And (5) controlling the temperature of the electromagnetic stirrer.
The preparation method of the liquid crystal composition comprises the following steps:
(1) orderly placing the used liquid crystal monomers;
(2) placing the stainless steel beaker on a balance, and putting the monomer into the stainless steel beaker by using a small spoon;
(3) adding liquid crystal monomers according to the required weight in sequence;
(4) placing the stainless steel beaker added with the liquid crystal monomer 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 mixture, and cooling to room temperature to obtain the liquid crystal composition.
The liquid crystal monomer structure of the embodiment of the invention is represented by codes, and the code representation methods of the liquid crystal ring structure, the end group and the connecting group are shown in the following tables 1 and 2.
Corresponding code of the ring structure of Table 1
TABLE 2 corresponding codes for end groups and linking groups
Examples are:
the code is PGP-Cpr 1-2.
Synthetic route for compounds of formula I
The compounds of formula I above may be synthesized by, but are not limited to, the following synthetic routes:
in the above synthetic route, R represents-CH or more than one of cyclopropyl, cyclopentyl and alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene; y represents OCF3、CF3、CF2H or OCF2H；
To represent
n represents 0 or 1.
In the above route, starting materials
And
can be obtained from public commercial sources. According to the synthesis route, Z in the formula I is a single bond, -CF can be prepared by only replacing raw materials2O-or-COO-compounds. The method principle, the operation process, the conventional post-treatment, the silica gel column passing, the recrystallization purification and other means are well known by synthesizers 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, N-dimethylformamide, dimethyl sulfoxide, ethanol, methanol, dichloromethane, acetone, toluene and deionized water.
Example 1 Compounds of formula I1a
Step 1
Adding 39g (0.30mol) of 2, 3-difluorophenol, 33g (0.33mol) of cyclopentyl methanol, 91.7g (0.35mol) of triphenylphosphine and 500ml of tetrahydrofuran into a 2L three-necked bottle, stirring until the mixture is completely dissolved, dropping 61g (0.35mol) of 300ml of tetrahydrofuran solution of diethyl azodicarboxylate when the temperature is reduced to 0-10 ℃ under the protection of nitrogen, keeping the temperature for 0-10 ℃, adding the mixture for half an hour, and stirring for 4 hours at room temperature; adding 500ml of water and 300ml of toluene into the reaction solution, stirring for 10min, standing, separating liquid, extracting a water layer by using 300ml of multiplied by 2 toluene, combining organic layers, washing by using 40% ethanol 300ml of multiplied by 2, washing by using 300ml of multiplied by 2 saturated saline, carrying out spin-drying on the solvent under reduced pressure, adding 200ml of petroleum ether into the obtained liquid, passing the obtained liquid through a column, washing the column by using 400ml of petroleum ether, carrying out spin-drying on the solvent, and carrying out distillation under reduced pressure to obtain 50g of a light yellow liquid product (1-a), and carrying out GC: 97.0% and yield 78%.
Step 2
Adding 50g (0.24mol) (1-a) and 300mL tetrahydrofuran into a 1L three-necked bottle, starting stirring, filling nitrogen to replace air, placing the three-necked bottle in a low-temperature tank, cooling by using liquid nitrogen, dropping 104mL (0.26mol) of 2.5M butyllithium when the temperature is reduced to-78 ℃, finishing dropping for 20 minutes, after heat preservation reaction for half an hour, still dropping 100mL tetrahydrofuran solution of 28g (0.26mol) trimethyl borate at-78 ℃, finishing adding for 20 minutes to obtain transparent solution, removing the low-temperature tank, naturally heating to-20 ℃ (after the temperature is raised to-20 ℃ (after the time is used for 2 hours), pouring 750mL deionized water with 100mL hydrochloric acid for hydrolysis, separating, extracting the water phase once by using 500mL ethyl acetate, combining the organic layers, and washing to be neutral by water. The solvent was evaporated under reduced pressure, 150ml of petroleum ether was added, heated to boiling, cooled and filtered to obtain 40g of a white solid (1-b), yield: 66 percent.
Step 3
Adding 48.6g (0.20mol) of 2-fluoro-4-bromotrifluoromethylbenzene and 250mL of tetrahydrofuran into a 1L three-necked bottle, starting stirring, filling nitrogen to replace air, placing the bottle in a low-temperature tank, cooling the bottle by using liquid nitrogen, dropping 88mL (0.22mol) of 2.5M lithium diisopropylamide petroleum ether solution when the temperature is reduced to-78 ℃, completing the addition for half an hour, after reacting for half an hour, dropping 50mL of tetrahydrofuran solution of 27g (0.25mol) trimethyl borate at-78 ℃, completing the addition for half an hour to obtain a transparent solution, removing the low-temperature tank, naturally heating the bottle to-20 ℃ (2 hours later), pouring 750mL of deionized water with 100mL of hydrochloric acid for hydrolysis, separating the solution, extracting the aqueous phase once by using 500mL of ethyl acetate, combining the organic layers, and washing the organic layers to be neutral. The solvent was evaporated under reduced pressure, 150ml of petroleum ether was added, heated to boiling, cooled and filtered to obtain 40g of a white solid (1-c), HPLC: 96.8%, yield: 70 percent.
Step 4
Adding 40g (0.14mol) (1-c) of tetrahydrofuran 300mL into a 1L three-necked bottle, stirring until the tetrahydrofuran is completely dissolved, adding 60g of hydrogen peroxide, stirring uniformly, heating and refluxing for 5 hours; the reaction was stopped, cooled to room temperature, 300ml of dichloromethane was added, liquid separation was performed with shaking, the aqueous layer was extracted with 300ml of × 2 dichloromethane, dichloromethane was combined, washed with 300ml of × 2 saturated aqueous sodium chloride solution, dried over 25g of anhydrous sodium sulfate, and the solution was spin-dried to obtain 29g of a pale yellow liquid (1-d), GC: 95.2% and a yield of 81%.
Step 5
Adding 25.6g (0.10mol) (1-b), 25.9g (0.10mol) (1-d), 26.5g (0.25mol) of sodium carbonate, 300ml of toluene, 300ml of ethanol and 150ml of pure water into a 1L three-necked bottle, stirring until the mixture is completely dissolved, adding 0.15g of tetrakis (triphenylphosphine) palladium under the protection of nitrogen, and heating and refluxing for reaction for 5 hours; the reaction was stopped, 300ml of pure water was added and the liquid was separated by stirring, the aqueous layer was extracted with 200ml of X2 toluene, the organic layers were combined, washed with 300ml of X2 saturated brine, the solvent was dried by spinning under reduced pressure, the resulting liquid was stirred with 150g of petroleum ether and frozen at-20 ℃ for 1 hour to obtain 30g of a white solid (1-e), GC: 99.0% and a yield of 77%.
Step 6
Adding 30g (0.077mol) (1-e) into a 500ml three-neck flask, adding 200ml dimethyl sulfoxide (DMSO) under the protection of nitrogen, stirring uniformly, adding 6.0g (0.15mol) of 60% sodium hydride mineral oil, heating to 120 ℃, and stirring for 4 hours; stopping the reaction, cooling to room temperature, pouring the reaction solution into 300g of ice water, stirring to separate out a solid, performing suction filtration by using filter cloth to obtain a solid, drying in the air, adding 200ml of petroleum ether, heating to completely dissolve the solid, passing through a 30g hot silica gel column, flushing the column by using 200ml of hot petroleum ether, spin-drying the solution, heating to completely dissolve 1 time of toluene and 2 times of petroleum ether, and recrystallizing twice at 0 ℃ to obtain 13g of a white solid (I1 a), and performing GC: 99.85 percent and the yield is 45 percent.
The compound represented by formula I1a has an optical anisotropy Δ n of 0.135, a dielectric anisotropy Δ ε of-3.1, and a perpendicular dielectric constant ε⊥It was 23.2.
Example 2 Compounds of formula I1b
Step 1
Synthesis of 3-propylcyclopentylmethanol instead of cyclopentylmethanol as a starting Material in step 1 of reference example 1
Step 2
Starting from (2-a), synthesized according to step 2 of reference example 1
Step 3
Starting from (2-b) and (1-d), the synthesis was carried out in step 5 of reference example 1
Step 4
Synthesis of I1b from (2-c) reference example 1, step 6
The compound represented by formula I1b has an optical anisotropy Δ n of 0.134, a dielectric anisotropy Δ ε of-3.1, and a perpendicular dielectric constant ε⊥It was 23.3.
Example 3 Compound of formula I4a
Step 1
2-fluoro-4-bromotrifluoromethoxybenzene instead of 2-fluoro-4-bromotrifluoromethylbenzene was used as a starting material, and synthesized in step 3 of reference example 1
Step 2
Starting from (3-a), synthesized according to step 4 of reference example 1
Step 3
Starting from (1-b) and (3-b), the synthesis was carried out in step 5 of reference example 1
(3-c)；
Step 4
Synthesis of I4a starting from (3-c) in step 6 of reference example 1
The compound represented by formula I4a has an optical anisotropy Δ n of 0.113, a dielectric anisotropy Δ ε of-3.2, and a perpendicular dielectric constant ε⊥Was 18.2.
Example 4A Compound of formula I4c
Step 1
Synthesized by using cyclopropylmethanol instead of cyclopentylmethanol as a starting material in step 1 of reference example 1
Step 2
Starting from (4-a), synthesized according to step 2 of reference example 1
Step 3
Starting from (4-b) and (3-b), synthesized in step 5 of reference example 1
Step 4
Synthesis of I4c starting from (4-c) in step 6 of reference example 1
The compound represented by formula I4c has an optical anisotropy Δ n of 0.115, a dielectric anisotropy Δ ε of-3.3, and a perpendicular dielectric constant ε⊥It was 19.2.
Example 5 liquid Crystal composition
The formulation and corresponding properties of the liquid crystal compositions are shown in table 3 below.
TABLE 3 formulation and corresponding Properties of the liquid crystal composition of example 5
Comparative example 1
The formulation and corresponding properties of the liquid crystal compositions are shown in table 4 below.
TABLE 4 formulation and corresponding Properties of the comparative example 1 liquid Crystal composition
By comparing example 5 with comparative example 1, the liquid crystal composition of example 5 containing the compound represented by the formula II has a vertical dielectric constant ε⊥The transmittance of the liquid crystal composition can be improved by obviously improving the transmittance.
Comparative example 2
The formulation and corresponding properties of the liquid crystal compositions are shown in table 5 below.
TABLE 5 formulation and corresponding Properties of the liquid crystal composition of comparative example 2
As is clear from comparison of example 6 with comparative example 2, the liquid crystal composition of example 6 containing the dibenzofuran structural compound having a terminal group of cyclopentyl, cyclopropyl substituted alkyl group has a higher clearing point and higher solubility than comparative example 2 using the dibenzofuran structural compound having a terminal group of linear alkoxy group in the liquid crystal composition.
Example 6
The formulation and corresponding properties of the liquid crystal compositions are shown in table 6 below.
TABLE 6 formulation and corresponding Properties of the liquid crystal composition of example 6
Example 7
The formulation and corresponding properties of the liquid crystal compositions are shown in table 7 below.
TABLE 7 formulation and corresponding Properties of the liquid crystal composition of example 7
Example 8
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 8 below.
TABLE 8 formulation and corresponding Properties of the liquid crystal composition of example 8
Example 9
The formulation and corresponding properties of the liquid crystal compositions are shown in table 9 below.
TABLE 9 formulation and corresponding Properties of the liquid crystal composition of example 9
Example 10
The formulation and corresponding properties of the liquid crystal composition are shown in table 10 below.
TABLE 10 formulation and corresponding Properties of the liquid crystal composition of example 10
Example 11
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 11 below.
TABLE 11 formulation and corresponding Properties of the liquid crystal composition of example 11
Example 12
The formulation and corresponding properties of the liquid crystal compositions are shown in table 12 below.
TABLE 12 formulation and corresponding Properties of the liquid crystal composition of example 12
Example 13
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 13 below.
TABLE 13 formulation and corresponding Properties of the liquid crystal composition of example 13
Example 14
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 14 below.
TABLE 14 formulation and corresponding Properties of the liquid crystal composition of example 14
Example 15
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 15 below.
TABLE 15 formulation and corresponding Properties of the liquid crystal composition of example 15
Example 16
The formulation of the liquid crystal composition and the corresponding properties are shown in Table 16 below.
TABLE 16 formulation and corresponding Properties of the liquid crystal composition of example 16
Example 17
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 17 below.
TABLE 17 formulation and corresponding Properties of the liquid crystal composition of example 17
Example 18
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 18 below.
TABLE 18 formulation and corresponding Properties of the liquid crystal composition of example 18
Example 19
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 19 below.
TABLE 19 formulation and corresponding Properties of the liquid crystal composition of example 19
Example 20
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 20 below.
TABLE 20 formulation and corresponding Properties of the liquid crystal composition of example 20
Example 21
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 21 below.
TABLE 21 formulation and corresponding Properties of the liquid crystal composition of example 21
Example 22
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 22 below.
TABLE 22 formulation and corresponding Properties of the liquid crystal composition of example 22
Claims (11)
1. A liquid crystal compound, which is characterized in that the liquid crystal compound is shown as the following formula I:
wherein: in the formula I, the compound is shown in the specification,
r represents at least one-CH of cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
y represents-OCF3、-CF3、-CF2H or-OCF2H；
Z represents a single bond, -CH2O-、-CF2O-or-COO-;
n represents 0 or 1.
2. The liquid crystal compound according to claim 1, wherein the liquid crystal compound of formula I is selected from the group consisting of compounds of formulae I1 to I32,
wherein:
r represents-CH (-CH) of more than one of cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
3. A liquid crystal composition containing the liquid crystal compound according to claim 1 or 2.
4. A liquid crystal composition comprising one or more compounds of formula II, one or more compounds of formula III, and one or more compounds of formula IV,
wherein the content of the first and second substances,
in the formula II, R' represents more than one-CH in cyclopropyl, cyclopentyl or alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
y' represents-F, -OCF3、-CF3、-CF2H or-OCF2H；
Z1Represents a single bond, -CH2O-、-CF2O-or-COO-;
n1Represents 0 or 1;
in the formula III, R1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R1Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
Z2Represents a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
X1、X2each independently represents H or F; x3Represents H, F or methyl;
Y1represents-F, -CF3、-OCF3、-OCF2H or-OCH2F；
m represents 0, 1 or 2;
in the formula IV, R2、R3Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
5. The liquid crystal composition of claim 4, wherein the one or more compounds of formula II are selected from the group consisting of compounds of formulae II1-II 40, the one or more compounds of formula III are selected from the group consisting of compounds of formulae III1-III27, and the one or more compounds of formula IV are selected from the group consisting of compounds of formulae IV 1-IV 16;
wherein the content of the first and second substances,
r' represents-CH (CH) of more than one of cyclopropyl, cyclopentyl and alkyl with 2-10 carbon atoms2-a group obtained after substitution with cyclopropylene or cyclopentylene;
R1Represents an alkyl group having 1 to 10 carbon atoms, having 1 to 10 carbon atomsAn alkoxy group of 1 to 10, an alkenyl group of 2 to 10 carbon atoms or an alkenyloxy group of 3 to 8 carbon atoms, and R1Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
(F) each independently represents H or F.
6. The liquid crystal composition of claim 4 or 5, further comprising one or more compounds of formula V:
wherein:
R4、R5each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
each independently represent
r represents 2 or 3.
7. The liquid crystal composition of claim 6, wherein the one or more compounds of formula V are selected from the group consisting of compounds of formulae V1-V10,
wherein the content of the first and second substances,
R41each independently represents an alkyl group having 2 to 6 carbon atoms, R42Each independently represents an alkenyl group having 2 to 6 carbon atoms, R51Each independently represents an alkyl group having 1 to 6 carbon atoms, R52Each independently represents an alkoxy group having 1 to 6 carbon atoms;
R43、R53each independently represents an alkyl group having 1 to 6 carbon atoms.
8. The liquid crystal composition of any one of claims 4 to 7, further comprising one or more compounds of formula VI:
wherein the content of the first and second substances,
R6、R7each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R6、R7Any one or more of the radicals indicated being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z3represents a single bond, -CF2O-、-CH2CH2-or-CH2O-；Z4Represents a single bond, -CH2CH2-or-CH2O-；
p represents 1 or 2;
q represents 0, 1 or 2.
9. The liquid crystal composition of claim 8, wherein the one or more compounds of formula VI are selected from the group consisting of compounds of formulae VI 1-VI 21,
wherein the content of the first and second substances,
R6、R7each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R6、R7Any one or more of the radicals indicated being unconnected-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene.
10. The liquid crystal composition of any of claims 4 to 9, further comprising one or more compounds of formula vii:
wherein R is8、R9Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R8、R9Any one or more-CH of the groups shown2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
x represents O, S or CH2O。
11. A liquid crystal display element or a liquid crystal display comprising the liquid crystal composition according to any one of claims 3 to 10, wherein the liquid crystal display element or the liquid crystal display is an active matrix display element or a display, a passive matrix display element or a display.
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| CN114196417A (en) * | 2021-12-22 | 2022-03-18 | 北京云基科技有限公司 | Liquid crystal compound containing cyclopentyl and application |
| CN115247072A (en) * | 2021-04-27 | 2022-10-28 | 江苏和成显示科技有限公司 | Liquid crystal composition containing dibenzo derivative and application thereof |
| TWI796679B (en) * | 2021-04-01 | 2023-03-21 | 大陸商石家莊誠志永華顯示材料有限公司 | Positive dielectric anisotropy liquid crystal composition, liquid crystal display element or liquid crystal display |
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