CN102690167B - Liquid crystal compound containing saturated indene rings and composition thereof - Google Patents
Liquid crystal compound containing saturated indene rings and composition thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 239000013078 crystal Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 28
- 239000012074 organic phase Substances 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000012043 crude product Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 229960000935 dehydrated alcohol Drugs 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 229940125782 compound 2 Drugs 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000007868 Raney catalyst Substances 0.000 description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
- 229910000564 Raney nickel Inorganic materials 0.000 description 7
- 230000006837 decompression Effects 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000011056 performance test Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000007599 discharging Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002469 indenes Chemical class 0.000 description 5
- -1 methyl halide triphenylphosphine salt Chemical class 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- YKYMGFHOJJOSEB-UHFFFAOYSA-N butan-1-ol;potassium Chemical compound [K].CCCCO YKYMGFHOJJOSEB-UHFFFAOYSA-N 0.000 description 4
- 210000002858 crystal cell Anatomy 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000008447 perception Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- SNWQUNCRDLUDEX-UHFFFAOYSA-N inden-1-one Chemical class C1=CC=C2C(=O)C=CC2=C1 SNWQUNCRDLUDEX-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- 0 Cc1cc*(C=C(C)C=C=C2)c2c1 Chemical compound Cc1cc*(C=C(C)C=C=C2)c2c1 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- VNXUIRXHRSJUNQ-UHFFFAOYSA-N bromoethane;triphenylphosphane Chemical compound CCBr.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VNXUIRXHRSJUNQ-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- QQCFOQNFPIAENW-UHFFFAOYSA-N 1,3-difluoro-5-iodobenzene Chemical compound FC1=CC(F)=CC(I)=C1 QQCFOQNFPIAENW-UHFFFAOYSA-N 0.000 description 1
- RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical compound FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XUMQMKMQHDNIIN-UHFFFAOYSA-N CCCCC(CCC)c(cc1F)cc(F)c1F Chemical compound CCCCC(CCC)c(cc1F)cc(F)c1F XUMQMKMQHDNIIN-UHFFFAOYSA-N 0.000 description 1
- WNJSZOGOYJDJMP-UHFFFAOYSA-N ClCOCCl.C1=CC=C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound ClCOCCl.C1=CC=C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 WNJSZOGOYJDJMP-UHFFFAOYSA-N 0.000 description 1
- FAOBFWHWLCQTSN-UHFFFAOYSA-N Fc(ccc(C1CCCCC1)c1)c1F Chemical compound Fc(ccc(C1CCCCC1)c1)c1F FAOBFWHWLCQTSN-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 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 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical class CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides compounds of a formula (I) containing saturated indene rings, wherein one of A1 and A6 rings is a radical of formula (I), and m, n, p and s each independently represent 0, 1 or 2, and m+n+p+s>= 0. The compounds are provided with good chemical and physical stability and low birefringence. The invention also provides a liquid crystal composition constituted by one or more of said compounds. The liquid crystal composition has characteristics of good low-temperature intersolubility and small birefringence, and is applicable to mixed crystal systems with small birefringence such as TN, TFT, VA and FFS, especially ECB and IPS display modes.
Description
Technical field
The present invention relates to a kind of liquid crystalline cpd and comprise the composition of described liquid crystalline cpd, more particularly, the present invention relates to a kind of novel liquid crystalline cpd containing saturated indenes lopps and comprise the liquid-crystal composition of described liquid crystalline cpd.
Background technology
Liquid crystal material must have good chemistry and thermostability and the good stability to electric field and electromagnetic radiation.In addition, liquid crystal material should have low viscosity and in liquid crystal cell, produce short addressing time, low threshold voltage and high-contrast.They also should, at normal operations temperature,, in the possible wide region above and below room temperature, have the mesomorphous phase that is applicable to above-mentioned liquid crystal cell, for example nematic or cholesteric mesomorphous phase.But liquid crystal uses usually used as the mixture of various ingredients, these components are easily miscible each other.In addition, other performances of liquid crystal, as specific conductivity, dielectric anisotropy and optical anisotropy must meet various requirement according to brilliant box type and Application Areas.
Use the mixed liquid crystal on MLC indicating meter, notebook or automobile instrument, except relating to the contrast gradient problem relevant with the time of response, want to obtain high resistivity and also occurred difficulty, along with the reduction of resistivity, the contrast gradient meeting variation of indicating meter, and may produce the problem that after image disappears.For TV and Video Applications, need to there is the indicating meter of short time of response.Especially, if use the liquid-crystal composition with low viscosity value, can realize this short time of response.But dilution has conventionally reduced clearing point with additive and has reduced thus the working range of mixed liquid crystal.As in TN liquid crystal cell, need to facilitate the medium of the following advantages in liquid crystal cell:
1. the nematic phase range (being particularly low to moderate low temperature) expanding;
2. the changeable property under extremely low temperature;
3. the ultra-violet radiation resisting improving;
4. low threshold voltage.
But the mixed liquid crystal obtaining in existing technology can not be realized these advantages in keeping other parameters.Therefore, still and need to not show these shortcomings or show the high resistivity of having of these features on compared with low degree, there is the mixed liquid crystal of large operating temperature range, short response time (even at low temperatures) and low threshold voltage simultaneously.
Summary of the invention
The object of this invention is to provide a kind of novel liquid crystalline cpd that comprises saturated indenes lopps, this compound has good chemistry and physical stability and low degree of birefringence.
Another object of the present invention is to provide a kind of liquid-crystal composition that comprises the described novel liquid crystalline cpd that comprises saturated indenes lopps, and this liquid-crystal composition has good low temperature mutual solubility.
For addressing the above problem, the present invention proposes following technical scheme:
One aspect of the present invention, provides one to comprise saturated indenes lopps novel cpd, and described compound has the structure shown in general formula (I):
Wherein,
R
1, R
2separately independently expression-H ,-F ,-Cl ,-CN ,-NCS ,-SCN ,-OCN ,-NCO,
or the halo of 1-20 carbon atom or the alkyl of unsubstituted straight or branched or alkoxyl group, wherein, at described R
1and R
2in at least one-CH
2-can by-O-,-S-,-SiH
2-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
-CO-O-or-O-CO-substitute, its prerequisite is that heteroatoms is not directly connected to each other.
Ring A
2, A
3, A
4and A
5identical or different, choosing independently of one another freely
the group of composition, wherein, described ring A
2, A
3, A
4and A
5in one or more hydrogen atom quilt-D ,-F ,-Cl ,-CN ,-CF
3,-OCF
3,-CH
2f ,-OCH
2f ,-OCH
3or-CH
3replace, or described ring A
2, A
3, A
4and A
5in one or more-CH
2-quilt-S-,-CF
2-,-SiH
2-or-CO-substitutes, prerequisite is-O-,-S-or-CO-is not directly connected to each other, or described ring A
2, A
3, A
4and A
5in one～2-CH=quilt-N=substitute, ring A
1and A
6except same ring A
2, A
3, A
4and A
5definition outside, ring A
1and A
6can also be
wherein R
3and R
4same R
1and R
2definition, and its prerequisite be ring A
1and A
6in one of them is
Z
1, Z
2, Z
3, Z
4and Z
5identical or different, be independently from each other separately by carbon-carbon single bond and-CO-O-,-CF
2o-,-CH
2o-,-CH
2cH
2-,-CF
2cH
2-,-CF=CF-,-CH=CH-,-CH=CF-,-C
2f
4-,-(CH
2)
4-,-C
4f
8-,-OCF
2cF
2o-,-CF
2cF
2cF
2o-,-CH
2cH
2cF
2o-,-CH
2cF
2oCH
2-,-CH=CHCF
2o-,-CF
2oCH=CH-,-CF
2oCF=CH-,-CF
2oCH=CF-,-CF=CFCF
2o-,-CF
2oCF=CF-,-CH=CHCH
2cH
2-,-C
2h
4oCH
2-,-CH
2cH=CHCH
2-,-OCH
2cH
2cH
2-,-CF=CF-CF=CF-,-C ≡ C-CF=CF-,-C ≡ C-CF=CF-C ≡ C-,-CF=CF-C ≡ C-CF=CF-,-C ≡ C-CF
2the group of O-,-C ≡ C-composition, wherein, at described Z
1, Z
2, Z
3, Z
4and Z
5link group in any one-CH
2-can be by-SiH
2-substitute.
M, n, p and s are identical or different, represent independently of one another separately 0,1 or 2, and m+n+p+s >=0.
In some preferred embodiments, R
1, R
2separately independently expression-H ,-F ,-Cl ,-C ,-NCS,
or the group of the halo of 1-10 carbon atom or the alkyl of unsubstituted straight or branched or alkoxyl group composition, wherein, at described R
1and R
2in at least one-CH
2-Ji can by-O-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
or-CO-O-is alternative, and its prerequisite is that heteroatoms is not directly connected to each other.
In some preferred embodiments, ring A
2, A
3, A
4and A
5representative
ring A
1and A
6except same ring A
2, A
3, A
4and A
5definition outside, ring A
1or A
6can also be
but requiring is A
1and A
6encircling one of them is
In some preferred embodiments, Z
1, Z
2, Z
3, Z
4and Z
5expression-CO-O-independent of each other ,-CF separately
2o-,-CH
2o-,-OCH
2-,-CH
2cH
2-,-CF=CF-,-CH=CH-,-C
2f
4-,-(CH
2)
4-,-C
4f
8-,-OCF
2cF
2o-,-CH
2cH
2cF
2o-,-CF=CFCF
2o-,-C
2h
4oCH
2-,-OCH
2cH
2cH
2-,-C ≡ C-or carbon-carbon single bond.
In some preferred embodiments, m, n, p and s be expression 0,1 or 2 independent of each other separately, and 0≤m+n+p+s≤4.
In some embodiments, the compound of general formula (I) is particularly preferably one or more of following compound:
Another scheme of the present invention provides a kind of method of preparing above-claimed cpd, comprises the steps:
In solvents tetrahydrofurane, N
2under protection, in the scope of-5 DEG C～0 DEG C, the compound of formula 1 and methyl halide triphenylphosphine salt and propyl carbinol nak response, obtain the compound of general formula 2.Wherein, the compound of formula 1 can according to prior art, perception method be synthetic altogether.
In autoclave, using Raney Nickel as catalyzer, by general formula 2 and H
2under 1.5Mpa hydrogen pressure, react 5h, obtain the compound of general formula 3.
3) compound of general formula 3 and 80% formic acid are at room temperature stirred and spent the night, obtain the compound of general formula 4.
In solvents tetrahydrofurane, under nitrogen protection, under room temperature, the compound of general formula 4 is reacted with grignard reagent or lithium reagent, then through tosic acid dehydration, obtain the compound of general formula 5.
In autoclave, under room temperature taking 5%Pd/C as catalyzer, by the compound of general formula 5 and H
2at 1.5Mpa hydrogen pressure reaction 5h, obtain the compound of general formula (I).
A scheme more of the present invention provides a kind of liquid-crystal composition, comprises one or more of above-claimed cpds.
The monomer of the liquid crystalline cpd of general formula provided by the invention (I) has good chemistry and physical stability, containing compared with the monomer of phenyl ring, has low degree of birefringence with homogeneous structure; Compared with the liquid-crystal composition that contains this liquid crystalline cpd contains the liquid-crystal composition of phenyl ring with homogeneous structure, there is good low temperature mutual solubility.The mixed liquid crystal of being prepared by this liquid crystal monomer can be used for the little mixed crystal system of double refraction, particularly ECB and the IPS display formats such as TN, TFT, VA, FFS.
Embodiment
Below with reference to specific embodiments, the present invention is described.It should be noted that, the following examples are example of the present invention, are only used for illustrating the present invention, and are not used for limiting the present invention.In the situation that not departing from purport of the present invention or scope, can carry out other combination and various improvement in design of the present invention.
For ease of expressing, in following embodiment, the listed coded representation of table 1 for the unit structure of liquid crystalline cpd:
The unit structure code of table 1 liquid crystalline cpd
Taking the compound of following structural formula as example:
This structural formula, as represented by code listed in Table 1, can be expressed as: nOIdCUF, and the n in code represents the C atomicity of left end alkyl, for example n is " 3 ", represents that this alkyl is-C
3h
7; C in code represents cyclohexyl; U in code represents 2,5-, bis-fluoro phenylenes.
Embodiment 1
The synthetic route of the compound 1IdCUF of preparation is as follows:
Its concrete preparation process is as follows:
Wherein, dicyclo list is protected ketone and can be total to perception method synthetic (its synthetic method is with reference to US4307112) by prior art.
1) compound 1IdCUF-04's is synthetic
In 1L there-necked flask, add monobromethane triphenylphosphine salt 71g, tetrahydrofuran (THF) (THF) 300mL, N
2the lower icy salt solution of protection is cooled to-5 DEG C, adds propyl carbinol potassium 22g, adds rear reaction 30min, obtains orange suspension.Drip 60g monoethylene glycol and protect the THF solution 50mL of saturated indone, after adding ,-5 DEG C～0 DEG C rises to ambient temperature overnight naturally.Reaction solution proceeds in single port bottle, is spin-dried for solvent, and resistates adds 200mL petroleum ether, suction filtration, and sherwood oil is washing leaching cake repeatedly.With Rotary Evaporators evaporate to dryness sherwood oil filtrate, obtain crude product.Sherwood oil wash-out column chromatography for crude product, elutriant Rotary Evaporators evaporate to dryness, obtains the light yellow liquid (1IdCUF-04) of 27.36g, GC content 97.9%, yield 95%.
2) compound 1IdCUF-03's is synthetic
In 1L autoclave, add the intermediate of the above-mentioned preparation of 27.36g, 300mL ethanol, 5g 5% Pd/C, hydrogen pressure 1.5Mpa reacts 5h.Sampling GC monitoring reaction is complete.Discharging, filtering Pd/C, filtrate is steamed solvent to the greatest extent with Rotary Evaporators, obtains 27.1g light yellow liquid (1IdCUF-03), GC content 97.5%, yield 98%.
3) compound 1IdCUF-02's is synthetic
In 1L there-necked flask, add the intermediate of the above-mentioned preparation of 27.1g, 600mL 80% formic acid, stirred overnight at room temperature.300mL dichloromethane extraction twice for reaction solution, organic phase saturated sodium carbonate solution washed twice, then use 20g anhydrous sodium sulfate drying, dried organic phase is steamed solvent to the greatest extent with Rotary Evaporators, obtain 23.06g product (1IdCUF-02), GC content 97%, yield 85.1%.
4) compound 1IdCUF-01's is synthetic
In 500mL there-necked flask, add 4.0g Mg, 150mL THF, stirs.Under nitrogen protection, drip the 44.6g 5-(4-bromine cyclohexyl)-1,2 dissolving with 15mL THF, 3-trifluorobromobenzene; stirring at room temperature to grignard reagent causes, and continues to drip 3,4 of remainder after causing; the THF solution of 5-trifluorobromobenzene, keeps micro-reflux state, drips off rear backflow 1h.Under nitrogen protection, under micro-reflux state, drip the 1IdCUF-02 that 23.06g 100mL THF dissolves, 30min drips, back flow reaction 3h.Be chilled to below room temperature, add 100mL saturated aqueous ammonium chloride, separatory, 100mL ethyl acetate extraction three times for water, merges organic phase, with twice of 100mL water washing, organic phase 20g anhydrous sodium sulfate drying, steams solvent to the greatest extent with Rotary Evaporators decompression, obtains brown oil 56g.
In dry 500mL there-necked flask, add above-mentioned crude product, 300mL toluene, adds 1g tosic acid monohydrate under stirring.Temperature rising reflux divides water 2h, and tlc (TLC) detects without raw material.Reaction solution is cooled to room temperature, steams solvent to the greatest extent with Rotary Evaporators decompression, makees eluent with sherwood oil, column chromatography, elutriant steams sherwood oil to the greatest extent with Rotary Evaporators decompression again, and then with twice, 50mL dehydrated alcohol recrystallization, obtain product (1IdCUF-01) 32.57g, GC content 98.3%, yield 62%.
5) compound 1IdCUF's is synthetic
In 1L autoclave, add the intermediate of the above-mentioned preparation of 32.57g, 400mL ethanol, 8g Raney Nickel, hydrogen pressure 1.5Mpa reaction 5h under room temperature.Sampling GC monitoring reaction is complete.Discharging, filtering Raney Nickel, filtrate is steamed solvent to the greatest extent with Rotary Evaporators, obtains 32.2g colourless transparent liquid.Crude product, with after 100mL dehydrated alcohol recrystallization 3 times, obtains white solid 19.68g(1IdCUF), GC content 99.8%, yield 60%.
1H NMR(CDCl
3，300MHz)，δ(ppm)：6.8(dd，J=6.9，8.9Hz，2H)，2.38(tt，J=2.3，8.9Hz,，1H)，1.0～1.90(m，23H)，0.96(d，J=6.9Hz，3H)。
Embodiment 2
The synthetic route of the compound 1IdCGF of preparation is as follows:
Its concrete preparation process is as follows:
With step 1)～3 in embodiment 1) obtain 1IdCGF by following synthesis step again after preparing compound 1IdCUF-02.
4) compound 1IdCGF-01's is synthetic
Use the intermediate 1IdCUF-02 of preparation 1IdCUF, according to the synthetic 1IdCGF-01 of the method for above-mentioned synthetic 1IdCUF-01, with the alternative 44.6g 5-(4-bromine cyclohexyl)-1 of 41.5g 4-(4-bromine cyclohexyl)-1,2 difluoro bromobenzene, 2,3-trifluorobromobenzene.Can prepare 31.4g 1IdCGF-01, GC purity is 99.2%, yield: 63%.
5) compound 1IdCGF's is synthetic
According to the method for synthetic 1IdCUF, by 1IdCGF-01 hydro-reduction, then carry out recrystallization purifying, obtain 18.87g target product 1IdCGF, GC purity is 99.7%, yield: 59.8%.
1H NMR(CDCl
3，300MHz)，δ(ppm)：6.86～7.10(m，3H)，2.38(tt，J=3.3，12.2Hz，1H)，1.02～1.92(m，23H),0.95(d，J=6.9Hz，3H)。
Embodiment 3
The synthetic route of the compound 3IdZGF of preparation is as follows:
Its concrete preparation process can be total to perception method (its synthetic method is with reference to US5621147) with reference to prior art, specific as follows:
1) compound 3IdZGF-08's is synthetic
In 2L there-necked flask, add N-PROPYLE BROMIDE triphenylphosphine salt 270.7g, THF 1.2L, N
2the lower icy salt solution of protection is cooled to-5 DEG C, adds propyl carbinol potassium 80g, adds rear reaction 30min, obtains orange suspension.Drip 115g monoethylene glycol and protect the THF solution 300mL of saturated indone, after adding ,-5 DEG C～0 DEG C rises to ambient temperature overnight naturally.Reaction solution proceeds in single port bottle, is spin-dried for solvent, and resistates adds 200mL petroleum ether, suction filtration, and sherwood oil is washing leaching cake repeatedly.With Rotary Evaporators evaporate to dryness sherwood oil filtrate, obtain crude product.Sherwood oil wash-out column chromatography for crude product, elutriant Rotary Evaporators evaporate to dryness, obtains the light yellow liquid (3IdZGF-08) of 123.6g, GC content 97.9%, yield 95%.
2) compound 3IdZGF-07's is synthetic
In 1L autoclave, add the intermediate of the above-mentioned preparation of 123.6g, 800mL ethanol, 5g 5%Pd/C, hydrogen pressure 1.5Mpa reacts 5h.Sampling GC monitoring reaction is complete.Discharging, filtering Pd/C, filtrate is steamed solvent to the greatest extent with Rotary Evaporators, obtains 121g light yellow liquid (3IdZGF-07), GC content 96.5%, yield 97%.
3) compound 3IdZGF-06's is synthetic
In 2L there-necked flask, add the intermediate of the above-mentioned preparation of 121g, 1.2L 80% formic acid, stirred overnight at room temperature.300mL dichloromethane extraction twice for reaction solution, organic phase saturated sodium carbonate solution washed twice, then use 20g anhydrous sodium sulfate drying, dried organic phase is steamed solvent to the greatest extent with Rotary Evaporators, obtain 83.6g product (3IdZGF-06), GC content 95.8%, yield 86%.
4) compound 3IdZGF-05's is synthetic
In 2L there-necked flask, add chloromethyl ether triphenylphosphine salt 174.8g, THF 1.0L, N
2the lower icy salt solution of protection is cooled to-5 DEG C, adds propyl carbinol potassium 57g, adds rear reaction 30min, obtains orange suspension.Drip the THF solution 200mL of 83.6g 3IdZGF-06, after adding ,-5 DEG C～0 DEG C rises to ambient temperature overnight naturally.Reaction solution proceeds in single port bottle, is spin-dried for solvent, and resistates adds 200mL petroleum ether, suction filtration, and sherwood oil is washing leaching cake repeatedly.With Rotary Evaporators evaporate to dryness sherwood oil filtrate, obtain crude product.Sherwood oil wash-out column chromatography for crude product, elutriant Rotary Evaporators evaporate to dryness, obtains the light yellow liquid (3IdZGF-05) of 92.7g, GC content 94.6%, yield 96%.
5) compound 3IdZGF-04's is synthetic
In 1L there-necked flask, add the intermediate of 92.7 above-mentioned preparations,, THF 600mL, the aqueous hydrochloric acid of 165mL 3mol/L, 60 DEG C～65 DEG C stirring 3h of water, reaction solution adds 200mL ethyl acetate separatory, 200mL saturated sodium carbonate solution washing 3 times for organic phase, then use 100g anhydrous sodium sulfate drying, with Rotary Evaporators decompression steaming solvent to the greatest extent, obtain the weak yellow liquid (3IdZGF-04) of 79.7g, GC(cis+trans) content 92.8%, yield 92%.
6) compound 3IdZGF-03's is synthetic
In dry 2L there-necked flask, add 173.8g CF
2br
2with dry 800mLTHF, dissolve nitrogen protection borehole cooling to 0 DEG C-5 DEG C of dropping 267.3g tri-(dimethylamino) phosphines; 30min adds, and 0 DEG C-5 DEG C are stirred 10min, drip the 100mL THF solution of the intermediate of the above-mentioned preparation of 79.7g; 30min adds, and after reaction 3h, GC monitoring raw material reaction is complete.Reaction solution proceeds in single port bottle, be spin-dried for solvent, add 500mL sherwood oil+300mL water to crude product kind, separatory, water layer extracts once, merge all organic layers, washing twice, organic phase anhydrous sodium sulfate drying, PE crosses post and obtains 54.3g light yellow liquid (3IdZGF-03), GC(cis+trans): 96.2%, yield 58.1%.
7) compound 3IdZGF-02's is synthetic
In 2L autoclave, add the intermediate of the above-mentioned preparation of 54.3g, 192.8g CoF
3, 1.5mL water and 1.5L CCl
2fCClF
2after good seal, be warming up to 100 DEG C of reaction 3h, remove by filter inorganic salt, organic phase is first with the washing of 500mL saturated sodium bicarbonate aqueous solution, use 500mL water washing, organic phase is used 20g anhydrous sodium sulfate drying more again, and dried organic phase is crossed silicagel column, chromatographic solution steams solvent to the greatest extent with Rotary Evaporators, obtain 26.6g product (3IdZGF-02), GC(cis+trans): 89.3%, yield 42%.
8) compound 3IdZGF-01's is synthetic
In the dry there-necked flask of 500mL, add the intermediate of the above-mentioned preparation of 26.6g, the THF that 250mL is dry, nitrogen protection borehole cooling is to-78 DEG C, drip the 24mL butyllithium of 2.5mol/L, temperature control-78 DEG C～-80 DEG C, drip off rear temperature control-78 DEG C～-80 DEG C and stir 2h, naturally be warming up to room temperature, the dilute hydrochloric acid acidifying of 500mL 1mol/L for reaction solution, organic phase separatory, 300mL ethyl acetate extracting twice for water layer, organic phase merges uses saturated sodium bicarbonate aqueous solution washed twice, organic phase is used 20g anhydrous sodium sulfate drying again, dried organic phase is steamed solvent to the greatest extent with Rotary Evaporators, cross silicagel column with n-hexane dissolution again, chromatographic solution steams solvent to the greatest extent with Rotary Evaporators, obtain 14.76g product (3IdZGF-01), GC(cis+trans): 89.3%, yield 42%.
9) compound 3IdZGF's is synthetic
In the there-necked flask of 2L dried and clean, add 57.6g 3, 5-difluoro iodobenzene and 1.3L dry ether, nitrogen protection borehole cooling is to-78 DEG C, drip the 100mL butyllithium of 2.5mol/L, temperature control-78 DEG C～-80 DEG C, drip off rear temperature control-78 DEG C～-80 DEG C and stir 2h, and then the dry Tetramethyl Ethylene Diamine of dropping 27.8g, at-78 DEG C, drip the 100mL anhydrous ether solution of the intermediate of the above-mentioned preparation of 14.76g, being controlled at 45min-1h drips, drip off rear temperature control-78 DEG C～-80 DEG C and stir 1.5h, naturally be warming up to room temperature, the dilute hydrochloric acid acidifying of 300mL 1mol/L for reaction solution, organic phase separatory, 200mL ethyl acetate extracting twice for water layer, organic phase merges uses saturated sodium bicarbonate aqueous solution washed twice, organic phase is used 30g anhydrous sodium sulfate drying again, dried organic phase is steamed solvent to the greatest extent with Rotary Evaporators, cross silicagel column with n-hexane dissolution again, chromatographic solution steams solvent to the greatest extent with Rotary Evaporators, crude product is used methyl alcohol recrystallization 5 times at-50 DEG C again, under low temperature, obtain 5.6g white solid (containing methyl alcohol), under room temperature, drain solvent and obtain 3.88g colourless transparent liquid (3IdZGF).GC:99.6%, yield 19%.
1H NMR(CDCl
3，300MHz)，δ(ppm)：76.94～7.30(m，3H)，2.74(m，1H)，0.82～2.2(m，17H),0.88(t，J=8.1Hz，3H)。
Embodiment 4
The synthetic route of compound 2 (Id) PGUQUF of preparation is as follows:
Its concrete preparation process can be total to perception method (its synthetic method is with reference to European Journal of Organic Chemistry, and 2008, V20 is – 3487 p.3479) with reference to prior art, specific as follows:
1) compound 2 (Id) PGUQUF-06's is synthetic
In 100mL there-necked flask, add 0.03g Mg, 10mL THF, stirs.Under nitrogen protection, drip the 2.4g 4 '-bromo-3-fluorine biphenyl dissolving with 10mL THF, stirring at room temperature to grignard reagent causes, and continues to drip the THF solution of 4 remaining '-bromo-3-fluorine biphenyl after causing, and keeps micro-reflux state, drips off rear backflow 1h.The monoethylene glycol that drips 1.9g 10mLTHF dissolving under nitrogen protection under micro-reflux state is protected saturated indone, and 30min drips, back flow reaction 3h.Be chilled to below room temperature, add 15mL saturated aqueous ammonium chloride, separatory, 30mL ethyl acetate extraction three times for water, merges organic phase, with twice of 20mL water washing, organic phase 5g anhydrous sodium sulfate drying, steams solvent to the greatest extent with Rotary Evaporators decompression, obtains brown oil 3.2g.
In dry 100mL there-necked flask, add above-mentioned crude product, 50mL toluene, adds 0.1g tosic acid monohydrate under stirring.Temperature rising reflux divides water 4h, and tlc (TLC) detects without raw material.Reaction solution is cooled to room temperature, with Rotary Evaporators decompression steaming solvent to the greatest extent, make eluent with sherwood oil, column chromatography, elutriant steams sherwood oil to the greatest extent with Rotary Evaporators decompression again, and then with 4mL dehydrated alcohol recrystallization twice, obtains product (2 (Id) PGUQUF-06) 2.2g, GC content 99.2%, yield 65%.
2) compound 2 (Id) PGUQUF-05's is synthetic
In 1L autoclave, add the intermediate of the above-mentioned preparation of 2.2g, 10mL dehydrated alcohol and 5mL toluene, 5g 5% Raney Nickel, hydrogen pressure 1.5Mpa reacts 5h.Sampling GC monitoring reaction is complete.Discharging, filtering Raney Nickel, filtrate is steamed solvent to the greatest extent with Rotary Evaporators, and the crude product obtaining is used 4ml dehydrated alcohol recrystallization 3 times again, obtains 1.6g colourless transparent liquid (2 (Id) PGUQUF-05), GC content 99.4%, yield 72%.
3) compound 2 (Id) PGUQUF-04's is synthetic
In 1L there-necked flask, add the intermediate of the above-mentioned preparation of 1.6g, 40mL 80% formic acid and 10mL toluene, stirred overnight at room temperature.20mL toluene extracting twice for reaction solution, organic phase saturated sodium carbonate solution washed twice, then use 5g anhydrous sodium sulfate drying, dried organic phase is steamed solvent to the greatest extent with Rotary Evaporators, obtain 1.29g product (2 (Id) PGUQUF-04), GC content 98.6%, yield 92%.
4) compound 2 (Id) PGUQUF-03's is synthetic
In 50mL there-necked flask, add monobromethane triphenylphosphine salt 1.9g, tetrahydrofuran (THF) (THF) 10mL, N
2the lower icy salt solution of protection is cooled to-5 DEG C, adds propyl carbinol potassium 0.6g, adds rear reaction 30min, obtains milk yellow suspension.Drip the THF solution 10mL of 1.29g2 (Id) PGUQUF-04, after adding ,-5 DEG C～0 DEG C rises to ambient temperature overnight naturally.Reaction solution proceeds in single port bottle, is spin-dried for solvent, and resistates adds 30mL petroleum ether, suction filtration, and sherwood oil is washing leaching cake repeatedly.With Rotary Evaporators evaporate to dryness sherwood oil filtrate, obtain crude product.Sherwood oil wash-out column chromatography for crude product, elutriant Rotary Evaporators evaporate to dryness, obtains the white solid (2 (Id) PGUQUF-03) of 1.28g, GC content 98.3%, yield 96%.
5) compound 2 (Id) PGUQUF-02's is synthetic
In 1L autoclave, add the intermediate of the above-mentioned preparation of 1.28g, 100mL ethanol and 100mL toluene, 0.5g Raney Nickel, hydrogen pressure 1.5Mpa reacts 5h.Sampling GC monitoring reaction is complete.Discharging, filtering Raney Nickel, filtrate is steamed solvent to the greatest extent with Rotary Evaporators, obtain 1.28g colourless transparent liquid, then use 4mL dehydrated alcohol recrystallization 3 times, obtain 0.84g white powder (2 (Id) PGUQUF-02), GC content 98.8%, yield 65%.
6) compound 2 (Id) PGUQUF-01's is synthetic
In 50mL there-necked flask, add the intermediate of the above-mentioned preparation of 0.84g, 20mL anhydrous tetrahydro furan, argon shield borehole cooling is to-90 DEG C, drip the s-butyl lithium of 0.3mL 1mol/L, after dripping off ,-85 DEG C～-90 DEG C are stirred 30min, the 10mL anhydrous tetrahydrofuran solution that drips again 0.76g iodine at-85 DEG C～-90 DEG C, dropwises, and is naturally warming up to room temperature; Reaction solution is poured in the saturated aqueous solution of sodium bisulfite of 10mL, proceed to separatory in separating funnel, 20mL ethyl acetate extracting twice for water layer, organism is laminated and use saturated sodium bicarbonate aqueous solution washed twice, organic layer is used 10g anhydrous sodium sulfate drying again, steam solvent to the greatest extent with Rotary Evaporators again, obtain 1.2g brown color solid.Crude product 4mL dehydrated alcohol recrystallization 1 time, obtains white solid 1.04g(2 (Id) PGUQUF-01), GC content 97.8%.
7) compound 2 (Id) PGUQUF's is synthetic
In the single port bottle of 25mL dried and clean, add the intermediate of the above-mentioned preparation of 1.04g, 0.9g 4-bis-fluoro-(3,4,5-trifluoromethoxy phenoxy base) methyl]-3, (its synthetic method is with reference to European Journal of Organic Chemistry for 5-difluorobenzene boric acid, 2008, V20p3479 – 3487), 0.55g anhydrous sodium carbonate, 2.5mL deionized water, 10mL toluene and 5mL dehydrated alcohol, after using argon replaces emptying, add 0.1g Pd[P (Ph)
3]
4.Reflux 6h under argon shield; the cooling rear separatory of reaction solution; organic phase is crossed silicagel column; with sherwood oil and the eluent ethyl acetate of 5:1; chromatographic solution steams solvent to the greatest extent with Rotary Evaporators, obtains 1.5g light yellow solid, and crude product is used 3mL sherwood oil and 2mL dehydrated alcohol recrystallization again; obtain 1.2g white solid (2 (Id) PGUQUF), GC content 99.8%.
1H NMR(CDCl
3，300MHz)，δ(ppm)：7.54(d,J=8.30Hz,2H),7.51-7.45(m,2H),7.41(d,J=12.2Hz,1H),7.32(d,J=8.20Hz,2H),7.26(d,J=8.10Hz,2H),7.03-6.95(m,2H),2.53(tt,J=12.1Hz,J=3.00Hz,1H),0.88～1.95(m,15H),0.83(t,J=7.1Hz,3H)。
Embodiment 5-7 is the performance test of liquid-crystal composition of the present invention below, and every example has corresponding comparative example:
In following examples test event to write a Chinese character in simplified form code name as follows:
Embodiment 5
Be mixed with by each compound listed in table 2 and weight percentage the liquid-crystal composition that comprises compound of the present invention, carry out performance test, test data is as shown in the table:
Table 2 liquid-crystal composition formula and test performance thereof
| Component codes | Weight percentage (%) | Performance parameter test result |
| 3CPO2 | 5 | △n=0.110 |
| 3CPP2 | 20 | Vth=2.35v |
| 5PP1 | 5 | Cp=73.1℃ |
| 3PPO2 | 10 | η=30.1mpa.s |
| VCCP1 | 5 | △ε=5.42 |
| 3CCV | 34 | |
| 3IGUQUF | 8 | |
| 2IGUQUF | 8 | |
| 1IdCUF | 5 |
Comparative example 5
The liquid-crystal composition that is mixed with reference examples 5 by each compound listed in table 3 and weight percentage, carries out performance test, and test data is as shown in the table:
Table 3 liquid-crystal composition formula and test performance thereof
| Component codes | Weight percentage (%) | Performance parameter test result |
| 3CPO2 | 5 | △n=0.119 |
| 3CPP2 | 20 | Vth=2.24v |
| 5PP1 | 5 | Cp=74.4℃ |
| 3PPO2 | 10 | η=28.2mpa.s |
| VCCP1 | 5 | △ε=5.55 |
| 3CCV | 34 | |
| 3IGUQUF | 8 | |
| 2IGUQUF | 8 | |
| 3CPUF | 5 |
Embodiment 6
Be mixed with by each compound listed in table 4 and weight percentage the liquid-crystal composition that comprises compound of the present invention, carry out performance test, test data is as shown in the table:
Table 4 liquid-crystal composition formula and test performance thereof
| Component codes | Weight percentage (%) | Performance parameter test result |
| 2CCGF | 14 | △n=0.118 |
| 3CCGF | 13 | Vth=2.15v |
| 3CCP3 | 6 | Cp=95℃ |
| 2CCPOCF3 | 15 | η=28.1mpa.s |
| 3CCPOCF3 | 10 | △ε=6.92 |
| 3CCV | 10 | |
| 3CCV1 | 8 | |
| 3IUQUF | 5 | |
| 3IGUQUF | 4 | |
| 2IGUQUF | 5 | |
| 2IZP3 | 5 | |
| 3IdZGF | 5 |
Comparative example 6
The liquid-crystal composition that is mixed with reference examples 6 by each compound listed in table 5 and weight percentage, carries out performance test, and test data is as shown in the table:
Table 5 liquid-crystal composition formula and test performance thereof
| Component codes | Weight percentage (%) | Performance parameter test result |
| 2CCGF | 14 | △n=0.126 |
| 3CCGF | 13 | Vth=2.08v |
| 3CCP3 | 6 | Cp=98℃ |
| 2CCPOCF3 | 15 | η=25.3mpa.s |
| 3CCPOCF3 | 10 | △ε=7.12 |
| 3CCV | 10 | |
| 3CCV1 | 8 | |
| 3IUQUF | 5 | |
| 3IGUQUF | 4 | |
| 2IGUQUF | 5 | |
| 2IZP3 | 5 | |
| 3PZGF | 5 |
Embodiment 7
Be mixed with by each compound listed in table 6 and weight percentage the liquid-crystal composition that comprises compound of the present invention, carry out performance test, test data is as shown in the table:
Table 6 liquid-crystal composition formula and test performance thereof
Comparative example 7
The liquid-crystal composition that is mixed with reference examples 7 by each compound listed in table 7 and weight percentage, carries out performance test, and test data is as shown in the table:
Table 7 liquid-crystal composition formula and test performance thereof
| Component codes | Weight percentage (%) | Performance parameter test result |
| 3CGPC3 | 4 | △n=0.135 |
| 3CGPC5 | 4 | Vth=2.52v |
| 3CCV | 50 | Cp=83.5℃ |
| 3CCV1 | 6 | η=21.4mpa.s |
| 3IGUQUF | 4 | △ε=5.23 |
| 3IZUQUF | 4 | |
| 3IZP3 | 6 | |
| 2IZP3 | 6 | |
| 2IZGUQUF | 4 | |
| 2IZUQUF | 4 | |
| 3PZGQU0CF3 | 4 | |
| 2PZUF | 4 |
With reference to comparative example 5,6 and 7, from the test data of above embodiment 5,6 and 7, the composition that comprises compound provided by the invention has less optical anisotropy, can be applicable to the little mixed crystal system of double refraction, particularly ECB and the IPS display formats such as TN, TFT, VA, FFS.
Claims (4)
1. a compound, the group of the freely following compound composition of described compound choosing:
Wherein, R
1, R
2the unsubstituted straight chained alkyl of an expression-F or 1-20 carbon atom independently separately;
Z
1, Z
2and Z
3expression-CF independently separately
2o-or carbon-carbon single bond.
2. compound as claimed in claim 1, the group of the freely following compound composition of wherein said compound choosing:
One kind as shown in the formula compound:
4. a liquid-crystal composition, comprises at least one according to the compound one of claim 1～3 Suo Shu.
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| TWI613277B (en) * | 2016-11-02 | 2018-02-01 | Daxin Materials Corporation | Liquid crystal compound, liquid crystal composition and liquid crystal display using the same |
| CN108690640B (en) * | 2018-07-17 | 2022-02-25 | 烟台显华化工科技有限公司 | Compound containing indene ring and liquid crystal medium |
| CN115572210B (en) * | 2022-12-08 | 2023-03-21 | 暨南大学 | (1,2,2,2-tetrafluoroethyl) arene derivative and preparation method and application thereof |
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| CN1717467A (en) * | 2002-11-29 | 2006-01-04 | 大日本油墨化学工业株式会社 | Indane compound-containing nematic liquid crystal composition |
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| WO2008034511A1 (en) * | 2006-09-21 | 2008-03-27 | Merck Patent Gmbh | Indane compounds for use as components of liquid crystal media |
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| CN1507427A (en) * | 2001-07-20 | 2004-06-23 | Ĭ��ר���ɷ�����˾ | Indane compounds with negative dielectric anisotropy |
| CN1717467A (en) * | 2002-11-29 | 2006-01-04 | 大日本油墨化学工业株式会社 | Indane compound-containing nematic liquid crystal composition |
| CN1867647A (en) * | 2003-10-17 | 2006-11-22 | 默克专利股份有限公司 | Liquid crystal medium containing fluorinated indane compounds |
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