CN105295949A - Liquid crystal compound containing terminal alkyl groups and liquid crystal composition - Google Patents

Liquid crystal compound containing terminal alkyl groups and liquid crystal composition Download PDF

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Publication number
CN105295949A
CN105295949A CN201510670393.1A CN201510670393A CN105295949A CN 105295949 A CN105295949 A CN 105295949A CN 201510670393 A CN201510670393 A CN 201510670393A CN 105295949 A CN105295949 A CN 105295949A
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liquid crystal
carbonatoms
nitrae
isosorbide
component
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CN105295949B (en
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员国良
张伟
张虎波
王奎
邵哲
王明霞
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Abstract

The invention discloses a liquid crystal compound containing terminal alkyl groups and a liquid crystal composition. The structural general formula of the liquid crystal compound containing the terminal alkyl groups is shown in the formula I (please see the formula in the specification). The liquid crystal composition has low viscosity and can achieve fast responding and meanwhile has moderate dielectric anisotropy delta epsilon, moderate optical anisotropy delta n and high heat and light stability, and particularly the liquid crystal has a high VHR value under the severe condition. Liquid crystal materials containing the liquid crystal composition have good chemical and thermal stability and good electric field and magnetic field radiation stability. Besides, as liquid crystal materials for the thin film transistor technology (TFT-LCD), the nematic phase temperature range is wide, birefringence anisotropy is suitable, resistivity is very high, ultraviolet resistance is good, the charge retention rate is high, and low steam pressure and other properties are achieved.

Description

Liquid crystalline cpd containing end alkyl and liquid-crystal composition
Technical field
The invention belongs to field of liquid crystals, being specifically related to a kind of liquid crystalline cpd and liquid-crystal composition containing holding alkyl.
Background technology
At present, it is more and more wider that the range of application of liquid crystalline cpd is expanded, and it can be applicable in polytype indicating meter, electro-optical device, sensor.For liquid crystalline cpd of a great variety in above-mentioned display field, wherein nematic liquid crystal is most widely used.Nematic liquid crystal has been applied in passive TN, STN matrix display and has had in the system of tft active matrix.
For thin-film transistor technologies (TFT-LCD) Application Areas, although market is very huge in recent years, technology is also ripe gradually, people to the requirement of technique of display also in continuous raising, especially in realization response fast, driving voltage is reduced to reduce the aspects such as power consumption.Liquid crystal material as one of important photoelectron material of liquid-crystal display, the effect important to the performance improving liquid-crystal display.
As liquid crystal material, need to have good chemistry and thermostability and the stability to electric field and electromagnetic radiation.And as thin-film transistor technologies (TFT-LCD) liquid crystal material, not only need to have as outside upward stability, also should have the performances such as wider nematic temperature range, suitable degree of birefringence anisotropy, very high resistivity, good anti-ultraviolet property, high electric charge conservation rate and low-steam pressure.
For dynamic menu display application, as LCD TV, in order to realize high-quality display, eliminating display frame ghost and hangover, requiring that liquid crystal has very fast response speed, therefore require that liquid crystal has lower rotary viscosity γ 1; In addition, in order to reduce equipment energy consumption, wish that the driving voltage of liquid crystal is low as far as possible, so the dielectric anisotropy △ ε improving liquid crystal is significant to mixed liquid crystal.
Summary of the invention
The object of this invention is to provide a kind of liquid crystalline cpd and liquid-crystal composition containing holding alkyl.
Provided by the invention containing end alkyl liquid crystalline cpd, its general structure such as formula shown in I,
In described formula I, R 1the alkene oxygen base that expression carbonatoms is the alkyl of 1-9, the carbonatoms of fluorine replacement is the alkyl of 1-9, carbonatoms is the alkoxyl group of 1-9, the carbonatoms of fluorine replacement is the alkoxyl group of 1-9, carbonatoms is the thiazolinyl of 2-9, the carbonatoms of fluorine replacement is the thiazolinyl of 2-9, carbonatoms is 3-8 or the carbonatoms that fluorine replaces are the alkene oxygen base of 3-8;
represent Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene or one or two-CH that Isosorbide-5-Nitrae-phenylene, fluorine replace 2-Isosorbide-5-Nitrae-cyclohexylidene of being replaced by oxygen;
X 1and X 2independently represent hydrogen or fluorine all separately;
X 3represent carbonatoms is the alkyl of 1-9, carbonatoms is 1-9 alkoxyl group, alkene oxygen base that thiazolinyl that carbonatoms is 2-9 or carbonatoms are 2-9;
Q represents 1 or 2.
Concrete, described R 1definition in, described carbonatoms is the alkyl that the alkyl of 1-9 is specially the alkyl of the alkyl of the alkyl of the alkyl of the alkyl of C1, C2, C3, C4, C5, C6, C7, C8, C9 or the alkyl of C1-C5 or C1-C4 or the alkyl of C1-C3 or C1-C2 or the alkyl of C2-C5 or C2-C4 or the alkyl of C2-C3 or C3-C5 or the alkyl of C3-C4 or C4-C5;
The carbonatoms that described fluorine replaces is the alkyl that the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of the fluorine of the alkyl that replaces of fluorine that the alkyl of 1-9 is specially C1, C2, C3, C4, C5, C6, C7, C8, C9 or C1-C5 or C1-C4 or C1-C3 or C1-C2 or C2-C5 or C2-C4 or C2-C3 or C3-C5 or C3-C4 or C4-C5 replaces;
Described carbonatoms is the alkoxyl group that the alkoxyl group of 1-9 is specially the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of C1, C2, C3, C4, C5, C6, C7, C8, C9 or the alkoxyl group of C1-C5 or C1-C4 or the alkoxyl group of C1-C3 or C1-C2 or the alkoxyl group of C2-C5 or C2-C4 or the alkoxyl group of C2-C3 or C3-C5 or the alkoxyl group of C3-C4 or C4-C5;
The carbonatoms that described fluorine replaces is that the alkoxyl group of 1-9 is specially C1, C2, C3, C4, C5, C6, C7, C8, the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the alkoxyl group of the fluorine replacement of C9 or the fluorine replacement of C1-C5 or the fluorine replacement of C1-C4 or the fluorine replacement of C1-C3 or the fluorine replacement of C1-C2 or the fluorine replacement of C2-C5 or the fluorine replacement of C2-C4 or the fluorine replacement of C2-C3 or the fluorine replacement of C3-C5 or the fluorine replacement of C3-C4 or the fluorine replacement of C4-C5,
Described carbonatoms is the thiazolinyl that the thiazolinyl of 2-9 is specially the thiazolinyl of the thiazolinyl of the thiazolinyl of C2, C3, C4, C5, C6, C7, C8, C9 or the thiazolinyl of C2-C5 or C2-C4 or the thiazolinyl of C2-C3 or C3-C5 or the thiazolinyl of C3-C4 or C4-C5;
The carbonatoms that described fluorine atom replaces is that the thiazolinyl of 2-9 is specially the thiazolinyl of C2, C3, C4, C5, C6, C7, C8, C9 of fluorine atom replacement or the thiazolinyl of the thiazolinyl of the thiazolinyl of the thiazolinyl of C2-C5 or C2-C4 or the thiazolinyl of C2-C3 or C3-C5 or the thiazolinyl of C3-C4 or C4-C5;
Described carbonatoms is that the alkene oxygen base of 3-8 is specially the alkene oxygen base of the alkene oxygen base of C3, C4, C5, C6, C7, C8 or the alkene oxygen base of C3-C5 or C3-C4 or the alkene oxygen base of C4-C5;
The carbonatoms that described fluorine atom replaces is the alkene oxygen base of C3, C4, C5, C6, C7, C8 or the alkene oxygen base of the alkene oxygen base of C3-C5 or C3-C4 or the alkene oxygen base of C4-C5 that the alkene oxygen base of 3-8 is specially that fluorine atom replaces;
Concrete, compound shown in described formula I is compound shown in formula I1 or formula I2:
In described formula I1 and formula I2, R 11all represent that carbonatoms is the alkyl of 2-5;
X 31represent that carbonatoms is the alkyl of 2-5, carbonatoms is 2-5 thiazolinyl or carbonatoms are the alkoxyl group of 2-5.
Shown in formula I, compound is according to R 1, the difference of X1, X2, X3, thus performance is slightly different.The base mateiral of liquid crystal compound can be used as, in the middle of the liquid crystal base mateiral that the compound that also likely can add other types to as adding material forms, such as, improve the dielectric anisotropy △ ε of liquid crystal compound or/and rotary viscosity γ 1or/and threshold voltage V thor/and the contrast gradient under low temperature is or/and optical anisotropy △ n is or/and clearing point Cp.
The ε of compound dielectric anisotropy △ shown in formula I is medium, between 6-15, belongs to middle polarity monomer, especially X 1, X 2when being all fluorine atom replacement, represent time, △ ε can reach about 15, is thus conducive to improving liquid crystal compound △ ε, reduces liquid crystal drive voltage.
The n of compound light anisotropy △ shown in formula I with structural changes and there is slightly wide scope, be comparatively suitable for generally, during for phenyl ring, △ n is comparatively large, about 0.140; during for hexanaphthene, △ n is less, about 0.10.
With compound shown in up-to-date style I, there is low rotary viscosity γ 1, large elastic constant, is conducive to the response speed improving liquid crystal compound; To ultraviolet light and heat, there is better stability, be particularly useful for allocating the exploitation to the higher dispensing liquid crystal of image retention requirement.
In addition, comprise the liquid crystal compound of component A, also belong to protection scope of the present invention; Wherein, described component A is made up of at least one in compound shown in aforementioned formula I provided by the invention;
Concrete, described liquid crystal compound also can comprise B component and component C;
Described B component is made up of at least one in compound shown in formula II;
Described component C is made up of at least one in compound shown in formula III;
In described formula II and formula III, R 2, R 3and R 4all be selected from the alkoxyl group of the alkyl of C1-C6, the alkenyl of C2-C6 or C1-C6;
represent Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene or Isosorbide-5-Nitrae-phenylene independently of one another;
be selected from least one in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene;
P is 2 or 3;
(F) H or F is represented;
X 4for F, Cl or-OCF 3.
Certainly, described liquid crystal compound also can only be made up of described component A, B component and component C.
Concrete, compound shown in described formula II is any one in compound shown in formula II1 to formula II13:
Compound shown in described formula III is any one in the compound of formula III 1 to III22:
In described formula III 1 to III22, R 4all be selected from least one in the alkoxyl group of the alkyl of C1-C6, the thiazolinyl of C2-C6 and C1-C6.
Described liquid crystal compound also comprises at least one in component D, component E and component F;
Described component D is made up of at least one in compound shown in formula IV;
In described formula IV, R 51and R 52be selected from the alkoxyl group of the alkyl of C1-C6, the alkenyl of C2-C6 and C1-C6 any one;
M is 1 or 2;
all be selected from least one in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene;
Concrete, shown in described formula IV, compound is selected from any one in compound shown in formula IV 1-IV 7:
In described formula IV 1-IV 7, R 51and R 52all be selected from the alkoxyl group of the alkyl of C1-C6, the thiazolinyl of C2-C6 and C1-C6 any one;
Described component E is made up of at least one in compound shown in formula V;
In described formula V, R 61and R 62be selected from the alkoxyl group of the alkyl of C1-C6, the thiazolinyl of C2-C6 and C1-C6 any one;
N is 1 or 2;
be selected from least one in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene;
Z is selected from singly-bound ,-CH 2o-,-COO-and-CH 2cH 2-at least one;
Concrete, compound shown in described formula V be selected from compound shown in formula V 1-V 5 any one:
In described formula V 1-V 5, R 61and R 62identical with formula V of definition;
Described component F is made up of at least one in compound shown in formula VI;
In described formula VI, R 1the alkene oxygen base that expression carbonatoms is the alkyl of 1-9, the carbonatoms of fluorine replacement is the alkyl of 1-9, carbonatoms is the alkoxyl group of 1-9, the carbonatoms of fluorine replacement is the alkoxyl group of 1-9, carbonatoms is the thiazolinyl of 2-9, the carbonatoms of fluorine replacement is the thiazolinyl of 2-9, carbonatoms is 3-8 or the carbonatoms that fluorine replaces are the alkene oxygen base of 3-8;
R 71represent fluorine ,-OCF 3or carbonatoms is the alkoxyl group of 1-9;
for Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene or one or two-CH that Isosorbide-5-Nitrae-phenylene, fluorine replace 2-Isosorbide-5-Nitrae-cyclohexylidene of being replaced by oxygen;
(F) H or F is represented.
Concrete, compound shown in described VI be selected from compound shown in formula VI 1-VI 7 any one:
More specifically, in described formula II to formula VI in substituent definition, the alkyl of described C1-C6 is specifically selected from least one in the alkyl of the alkyl of the alkyl of C1, C2, C3, C4, C5, C6 or C2-C6, the alkyl of C3-C6, the alkyl of C4-C6, the alkyl of C5-C6, the alkyl of C1-C5, the alkyl of C2-C5, the alkyl of C3-C5, the alkyl of C4-C5, the alkyl of C1-C4, the alkyl of C2-C4, the alkyl of C3-C4, the alkyl of C1-C3, the alkyl of C1-C2 and C2-C3;
The alkoxyl group of described C1-C6 is specifically selected from least one in the alkoxyl group of the alkoxyl group of the alkoxyl group of C1, C2, C3, C4, C5, C6 or C2-C6, the alkoxyl group of C3-C6, the alkoxyl group of C4-C6, the alkoxyl group of C5-C6, the alkoxyl group of C1-C5, the alkoxyl group of C2-C5, the alkoxyl group of C3-C5, the alkoxyl group of C4-C5, the alkoxyl group of C1-C4, the alkoxyl group of C2-C4, the alkoxyl group of C3-C4, the alkoxyl group of C1-C3, the alkoxyl group of C1-C2 and C2-C3;
The thiazolinyl of described C2-C6 is specifically selected from least one in the thiazolinyl of the thiazolinyl of the thiazolinyl of C2, C3, C4, C5, C6 or C2-C6, the thiazolinyl of C3-C6, the thiazolinyl of C4-C6, the thiazolinyl of C5-C6, the thiazolinyl of C2-C5, the thiazolinyl of C3-C5, the thiazolinyl of C4-C5, the thiazolinyl of C2-C4, the thiazolinyl of C3-C4 and C2-C3;
Concrete again, in described liquid crystal compound, the mass parts of each component is as follows respectively:
Component A:5-25 part, is specially 8,12,14,18,19 or 25 parts;
B component: 15-45 part, is specially 18,25,30,33,35,40 or 42 parts;
Component C:5-45 part, is specially 8,20,25,28,40 parts;
Component D:5-25 part, is specially 6,8,11,15 or 23 parts;
Component E:5-25 part, is specially 7 or 11 parts;
Component F:5-25 part, is specially 6,12,15,18,20 or 23 parts;
Described liquid crystal compound is specially following liquid crystal compound a to any one in liquid crystal compound g:
Wherein, described liquid crystal compound a comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound a specifically comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound b comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound b specifically comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound c comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound c specifically comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound d comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound d specifically comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound e comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound e specifically comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound f comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound f specifically comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound g comprises the component of following each mass parts or is made up of the component of following each mass parts:
Described liquid crystal compound g specifically comprises the component of following each mass parts or is made up of the component of following each mass parts:
In the liquid crystal monomer structure of above-mentioned coded representation, the coded representation method of liquid crystal ring structure, end group, linking group is in table 1 and table 2.
In addition; shown in liquid crystal display device containing compound shown in the formula I that the invention described above provides or described liquid crystal compound or liquid-crystal display and this formula I, compound or described liquid crystal compound are preparing the application in liquid crystal display device or liquid-crystal display, also belong to protection scope of the present invention.
Wherein, described liquid crystal display device or liquid-crystal display are specially active array addressing liquid crystal display device or active array addressing liquid-crystal display;
Described active matrix display element is specially TN-TFT, IPS-TFT or FFS-TFT liquid crystal display device;
Described active array addressing liquid-crystal display is specially TN-TFT, IPS-TFT or FFS-TFT liquid-crystal display;
Described IPS-TFT liquid crystal display device is more specifically switch liquid crystal display device in face;
Described FFS-TFT liquid crystal display device is more specifically fringing field switchable liquid crystal display element;
Described IPS-TFT liquid-crystal display is more specifically in-plane switching liquid crystal display;
Described FFS-TFT liquid-crystal display is more specifically LCDs.
Liquid-crystal composition provided by the invention has lower viscosity, quick response can be realized, have simultaneously moderate dielectric anisotropy Δ ε, moderate optical anisotropy Δ n, the high stability to light and heat especially liquid crystal there is high VHR numerical value in the extreme circumstances.Comprise the liquid crystal material of liquid-crystal composition provided by the present invention, not only there is good chemistry and thermostability and the stability to electric field and electromagnetic radiation.And, as thin-film transistor technologies (TFT-LCD) liquid crystal material, also there is the performances such as wider nematic temperature range, suitable degree of birefringence anisotropy, very high resistivity, good anti-ultraviolet property, high electric charge conservation rate and low-steam pressure.
Accompanying drawing explanation
Fig. 1 is the preparation flow of compound shown in formula I.
Fig. 2 is the mass spectrum of embodiment 1 gained target product.
Fig. 3 is the preparation flow of compound shown in formula VI.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Described method is ordinary method if no special instructions.Described starting material all can obtain from open commercial sources if no special instructions.
The preparation method of compound shown in above-mentioned formula I as shown in Figure 1.Wherein, reaction conditions a is BuLi, CF 2br 2, THF ,-70 DEG C; Reaction conditions b is DMFK 2cO 3, 100 DEG C.
The method of compound shown in above-mentioned preparation formula I has the easy advantage of synthesis, and synthesis cost is low, and building-up process waste liquid is easy to process.
This type of Method And Principle, operating process, conventional aftertreatment, the excessively means such as silicagel column, recrystallization purification are known by this area synthesis personnel, according to introduction below, can realize building-up process completely, obtain target product.
Reaction process is generally by the process of TLC monitoring reaction, the aftertreatment that reaction terminates is generally washing, extract, merge dry after organic phase, the lower steaming of decompression desolventizes, and recrystallization, column chromatography, those skilled in the art can both realize the present invention according to description below.
As one of liquid crystal compound component formula VI shown in can according to method shown in Fig. 3 preparation and obtain.This synthetic method has the easy advantage of synthesis, and synthesis cost is very low, and building-up process is pollution-free.One step SUZUKI coupling can be synthesized and obtained formula V I compound, and catalyzer can use four triphenylphosphines to close palladium, Pd/C, Pd-132 etc., in the basic conditions, has in water or water-less environment and realizes building-up process.Alkali can use sodium carbonate, sodium bicarbonate, salt of wormwood, potassiumphosphate etc., solvent can use toluene, ethanol, N, dinethylformamide, water, tetrahydrofuran (THF) etc., reaction conditions is generally completed through 1-6 hour under the condition of backflow, and reaction process can be followed the tracks of by TLC.Reaction process is generally by the process of TLC monitoring reaction, the aftertreatment that reaction terminates is generally washing, extract, merge dry after organic phase, the lower steaming of decompression desolventizes, and recrystallization, column chromatography, those skilled in the art can both realize according to shown description.
Such as, code be 3BB (3F, 5F) BCF2OB (3F, 4F, 5F) formula VI shown in compound can be prepared as follows and obtain:
3.9g (0.014mol) boric acid drops in 250ml there-necked flask together with 5.0g (0.014mol) bromo-derivative, then drops into 2.5g salt of wormwood, 100ml toluene, 30ml water, 0.1g catalyst P d-132, nitrogen replacement air, stirs lower reflux 2 hours.
Separate organic phase, wash 2 times, concentrated, petroleum ether dissolution crosses silicagel column, and sherwood oil recrystallization for several times, obtains the 3.0g. that GC purity is 99.91
MP：123℃。
Per-cent in this specification sheets is mass percent, and temperature is degree Celsius (DEG C), the concrete meaning of other symbols and test condition as follows:
Cp represents clearing point (DEG C), and DSC quantitative method is tested;
S-N represents that the crystalline state of liquid crystal is to nematic fusing point (DEG C);
Δ n represents optical anisotropy, n ofor the specific refractory power of ordinary light, n efor the specific refractory power of extraordinary ray, test condition is 25 ± 2 DEG C, 589nm, and Abbe refractometer is tested;
Δ ε represents dielectric anisotropy, Δ ε=ε ∥-ε ⊥, wherein, ε ∥for being parallel to the specific inductivity of molecular axis, ε ⊥for the specific inductivity perpendicular to molecular axis, test condition is 25 ± 0.5 DEG C, 20 microns of parallel boxes, and INSTEC:ALCT-IR1 tests;
γ 1 represents rotary viscosity (mPas), and test condition is 25 ± 0.5 DEG C, 20 microns of parallel boxes, and INSTEC:ALCT-IR1 tests;
ρ represents resistivity (Ω cm), and test condition is 25 ± 2 DEG C, and testing tool is TOYOSR6517 high resistant instrument and LE-21 liquid electrode.
VHR represents voltage retention (%), and test condition is 20 ± 2 DEG C, voltage is ± 5V, pulse width is 10ms, voltage hold-time 16.7ms.Testing apparatus is TOYOModel6254 liquid crystal property comprehensive tester.
τ represents the time of response (ms), testing tool be DMS-501, test condition is 25 ± 0.5 DEG C, and testing cassete is 3.3 microns of IPS testing cassetes, and interelectrode distance and electrode width are 10 microns, and frictional direction and electrode angle are 10 °.
T (%) represents transmitance, T (%)=100%* on state of (Vop) brightness/light-source brightness, testing apparatus DMS501, test condition is 25 ± 0.5 DEG C, testing cassete is 3.3 microns of IPS testing cassetes, interelectrode distance and electrode width are 10 microns, and frictional direction and electrode angle are 10 °
In the present invention, with in the liquid crystal monomer structure of coded representation, the coded representation method of liquid crystal ring structure, end group, linking group is in table 1 and table 2.
The corresponding code of table 1, ring structure
Table 2, end group and the corresponding code linking group
Citing:
corresponding code is H (5) CCV1;
corresponding code is 3BB (3F) B (3F, 5F) QB (3F, 5F) F;
Embodiment 1:
Step 1
Add 23.2g (0.1mol) 3,5-bis-fluoro-4 ˊ-pentylbiphenyl in 500ml there-necked flask, 100ml tetrahydrofuran (THF), nitrogen replacement air, is cooled to-70 DEG C, drips 0.11molBuLi, drips again and be dissolved with 0.12molCF after adding 2br 210mlTHF solution, be naturally warming up to 0 DEG C, hydrolysis, conventional processing.Obtain (1-a) that 32g purity is 70%.
Step 2
(1-a) 25g (70% is added in 500ml there-necked flask, 0.05mol) 4-(bromo-two fluoro-2-methyl-s)-3, the fluoro-4 '-propyl group-1 of 5-bis-, 1 '-biphenyl, the fluoro-4-thanatol of 8.7g (0.05mol) 3,5 two, 20g (0.15mol) salt of wormwood, 300mlDMF, is heated to 100 DEG C, insulation 3h.Close heating, be down to normal temperature.Feed liquid poured in 300ml water, stir 5min, leave standstill separatory, with ethyl acetate extraction aqueous phase twice, washing organic phase is to neutral.Be spin-dried for solvent.Ethyl alcohol recrystallization three times, GC:99.8%, yield 45%.
MP：37.6℃；
MS: see accompanying drawing 2.
As from the foregoing, this product structure is correct.
The liquid crystal property detected result of this compound is as follows:
Δn[589nm,20℃]：0.140；
Δε[1KHz,20℃]：10；
Cp：18℃。
According to the step identical with embodiment 1, only reactant is carried out corresponding replacement according to the substituting group in product, is belonged to the compound of formula I as follows:
Embodiment 2, liquid crystal compound a
According to table 1 Suo Shi, each component is mixed, obtain liquid crystal compound a provided by the invention.
The composition of table 1, liquid crystal compound a
Classification Liquid crystal monomer code Content (%)
Ⅲ 3CCB(3F,4F) 10
Ⅲ 4CCBOCF3 10
Ⅲ VCCB(3F,4F) 12
Ⅲ 2CCBB(3F,4F) 8
Ⅱ 3CCV 18
Ⅵ 3BB(3F,5F)BCF2OB(3F,4F,5F) 6
Ⅳ 3CCB1 11
Ⅰ 3BB(3F,5F)CF2OB(3F,5F)O2 12
Ⅰ 3BB(3F,5F)CF2OB(3F,5F)4 13
The liquid crystal property detected result of this liquid crystal compound a is as follows:
Δε[1KHz,20℃]：6.3
Δn[589nm,20℃]：0.11
Cp：99℃
γ 1：66mPa.s。
Embodiment 3, liquid crystal compound b
According to table 2 Suo Shi, each component is mixed, obtain liquid crystal compound b provided by the invention.
The composition of table 2, liquid crystal compound b
Classification Liquid crystal monomer code Content (%)
Ⅲ 4CCB(3F,4F) 9
Ⅲ 2CCBOCF3 8
Ⅲ VCCB(3F,4F) 11
Ⅱ 3CCV 20
Ⅱ 3CBO1 5
Ⅵ 3BB(3F,5F)BCF2OB(3F,4F,5F) 5
Ⅵ 3CB(3F,5F)BCF2OB(3F,4F,5F) 7
Ⅳ 3CCB1 6
Ⅳ VCCB1 11
Ⅳ VCBB2 6
Ⅰ 5BB(3F,5F)CF2OB(3F,5F)4 12
The liquid crystal property detected result of this liquid crystal compound b is as follows:
Δε[1KHz,20℃]：5.5
Δn[589nm,20℃]：0.11
Cp：98.5℃
γ 1：62mPa.s。
Embodiment 4, liquid crystal compound c
According to table 3 Suo Shi, each component is mixed, obtain liquid crystal compound c provided by the invention.
The composition of table 3, liquid crystal compound c
Classification Liquid crystal monomer code Content (%)
Ⅲ 4CCB(3F,4F) 7
Ⅲ 2CCBOCF3 7
Ⅲ 3B(3F)BB(-4F) 6
Ⅱ 3CCV 30
Ⅱ 3CCV1 3
Ⅵ 3BB(3F,5F)BCF2OB(3F,4F,5F) 9
Ⅵ 3CB(3F,5F)BCF2OB(3F)OCF3 9
Ⅳ 3CCB1 6
Ⅳ V2CCB1 9
Ⅰ 5BB(3F,5F)CF2OB(3F,5F)4 14
The liquid crystal property detected result of this liquid crystal compound c is as follows:
Δε[1KHz,20℃]：6.5
Δn[589nm,20℃]：0.12
Cp：90℃
γ 1：67mPa.s。
Embodiment 5, liquid crystal compound d
According to table 4 Suo Shi, each component is mixed, obtain liquid crystal compound d provided by the invention.
The composition of table 4, liquid crystal compound d
Classification Liquid crystal monomer code Content (%)
Ⅲ 2CCB(3F,4F) 8
Ⅱ 3CCV 35
Ⅱ 3CBO1 2
Ⅱ 1BB5 5
Ⅵ 3BB(3F,5F)BCF2OB(3F,4F,5F) 8
Ⅵ 4CB(3F,5F)BCF2OB(3F,4F,5F) 7
Ⅵ 3B(3F)B(3F,5F)BCF2OB(3F,5F)O2 8
Ⅳ 3CBB1 8
Ⅰ 5BB(3F,5F)CF2OB(3F,5F)4 10
Ⅰ 5BB(3F,5F)CF2OB(3F,5F)2V 9
The liquid crystal property detected result of this liquid crystal compound d is as follows:
Δε[1KHz,20℃]：9.4
Δn[589nm,20℃]：0.11
Cp：70℃
γ 1：72mPa.s。
Embodiment 6, liquid crystal compound e
According to table 5 Suo Shi, each component is mixed, obtain liquid crystal compound e provided by the invention.
The composition of table 5, liquid crystal compound e
Classification Liquid crystal monomer code Content (%)
Ⅲ 2CCB(3F,4F) 8
Ⅲ 3CCBB(3F,4F) 5
Ⅲ VCCBOCF3 12
Ⅱ 1BB5 5
Ⅱ 3CCV 25
Ⅵ 3BB(3F,5F)BCF2OB(3F,4F,5F) 8
Ⅵ 4CB(3F,5F)BCF2OB(3F,4F,5F) 7
Ⅵ 3B(3F)B(3F,5F)BCF2OB(3F,5F)O2 5
Ⅳ 3CBB1 6
Ⅴ 3BB(2F,3F)O2 11
Ⅰ 5BB(3F,5F)CF2OB(3F,5F)2V 8
The liquid crystal property detected result of this liquid crystal compound e is as follows:
Δε[1KHz,20℃]：7.3
Δn[589nm,20℃]：0.13
Cp：83℃
γ 1：68mPa.s。
Embodiment 7, liquid crystal compound f
According to table 6 Suo Shi, each component is mixed, obtain liquid crystal compound f provided by the invention.
The composition of table 6, liquid crystal compound f
Classification Liquid crystal monomer code Content (%)
Ⅲ 2CCB(3F,4F) 8
Ⅲ 3CCBB(3F,4F) 5
Ⅲ VCCBOCF3 12
Ⅱ 4CCV 5
Ⅱ 3CCV 30
Ⅵ 3BB(3F,5F)BCF2OB(3F,4F,5F) 10
Ⅵ 4CB(3F,5F)BCF2OB(3F,4F,5F) 5
Ⅴ 3CB(2F,3F)O2 7
Ⅰ 5BB(3F,5F)CF2OB(3F,5F)2V 8
Ⅰ 3BB(3F,5F)CF2OB(3F,5F)4 10
The liquid crystal property detected result of this liquid crystal compound f is as follows:
Δε[1KHz,20℃]：6.8
Δn[589nm,20℃]：0.10
Cp：78℃
γ 1：66mPa.s。
Embodiment 8, liquid crystal compound g
According to table 7 Suo Shi, each component is mixed, obtain liquid crystal compound g provided by the invention.
The composition of table 7, liquid crystal compound g
Classification Liquid crystal monomer code Content (%)
Ⅲ 2CCB(3F,4F) 8
Ⅲ 3CCBB(3F,4F) 5
Ⅲ 3CCBOCF3 12
Ⅱ 4CCV 5
Ⅱ 3CCV 35
Ⅱ 3CBO2 5
Ⅰ 5BB(3F,5F)CF2OB(3F,5F)2V 9
Ⅰ 5BB(3F,5F)CF2OB(3F,5F)4 10
Ⅰ 3BB(3F,5F)CF2OB(3F,5F)O2 11
The liquid crystal property detected result of this liquid crystal compound g is as follows:
Δε[1KHz,20℃]：4.3
Δn[589nm,20℃]：0.09
Cp：65℃
γ 1：60mPa.s。

Claims (9)

1. compound shown in formula I,
In described formula I, R 1the alkene oxygen base that expression carbonatoms is the alkyl of 1-9, the carbonatoms of fluorine replacement is the alkyl of 1-9, carbonatoms is the alkoxyl group of 1-9, the carbonatoms of fluorine replacement is the alkoxyl group of 1-9, carbonatoms is the thiazolinyl of 2-9, the carbonatoms of fluorine replacement is the thiazolinyl of 2-9, carbonatoms is 3-8 or the carbonatoms that fluorine replaces are the alkene oxygen base of 3-8;
represent Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene or one or two-CH that Isosorbide-5-Nitrae-phenylene, fluorine replace 2-Isosorbide-5-Nitrae-cyclohexylidene of being replaced by oxygen;
X 1and X 2independently represent hydrogen or fluorine all separately;
X 3represent carbonatoms is the alkyl of 1-9, carbonatoms is 1-9 alkoxyl group, alkene oxygen base that thiazolinyl that carbonatoms is 2-9 or carbonatoms are 2-9;
Q represents 1 or 2.
2. compound according to claim 1, is characterized in that: compound shown in described formula I is compound shown in formula I1 or formula I2:
In described formula I1 and formula I2, R 11all represent that carbonatoms is the alkyl of 2-5;
X 31represent that carbonatoms is the alkyl of 2-5, carbonatoms is 2-5 thiazolinyl or carbonatoms are the alkoxyl group of 2-5.
3. comprise the liquid crystal compound of component A;
Described component A is made up of at least one in compound shown in described formula I arbitrary in claim 1-2.
4. liquid crystal compound according to claim 3, is characterized in that: described liquid crystal compound also comprises B component and component C;
Described B component is made up of at least one in compound shown in formula II;
Described component C is made up of at least one in compound shown in formula III;
In described formula II and formula III, R 2, R 3and R 4all be selected from the alkoxyl group of the alkyl of C1-C6, the alkenyl of C2-C6 or C1-C6;
represent Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene or Isosorbide-5-Nitrae-phenylene independently of one another;
be selected from least one in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene;
P is 2 or 3;
(F) H or F is represented;
X 4for F, Cl or-OCF 3.
5. the liquid crystal compound according to claim 3 or 4, is characterized in that: described liquid crystal compound is made up of described component A, B component and component C.
6. the liquid crystal compound according to claim 4 or 5, is characterized in that: compound shown in described formula II is any one in compound shown in formula II1 to formula II13:
Compound shown in described formula III is any one in the compound of formula III 1 to III23:
In described formula III 1 to III23, R 4all be selected from least one in the alkoxyl group of the alkyl of C1-C6, the thiazolinyl of C2-C6 and C1-C6.
7., according to described liquid crystal compound arbitrary in claim 3-6, it is characterized in that: described liquid crystal compound also comprises at least one in component D, component E and component F;
Described component D is made up of at least one in compound shown in formula IV;
In described formula IV, R 51and R 52be selected from the alkoxyl group of the alkyl of C1-C6, the alkenyl of C2-C6 and C1-C6 any one;
M is 1 or 2;
all be selected from least one in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene;
Described component E is made up of at least one in compound shown in formula V;
In described formula V, R 61and R 62be selected from the alkoxyl group of the alkyl of C1-C6, the thiazolinyl of C2-C6 and C1-C6 any one;
N is 1 or 2;
be selected from least one in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene;
Z is selected from singly-bound ,-CH 2o-,-COO-and-CH 2cH 2-at least one;
Described component F is made up of at least one in compound shown in formula VI;
In described formula VI, R 1the alkene oxygen base that expression carbonatoms is the alkyl of 1-9, the carbonatoms of fluorine replacement is the alkyl of 1-9, carbonatoms is the alkoxyl group of 1-9, the carbonatoms of fluorine replacement is the alkoxyl group of 1-9, carbonatoms is the thiazolinyl of 2-9, the carbonatoms of fluorine replacement is the thiazolinyl of 2-9, carbonatoms is 3-8 or the carbonatoms that fluorine replaces are the alkene oxygen base of 3-8;
R 71represent fluorine ,-OCF 3or carbonatoms is the alkoxyl group of 1-9;
for Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylidene or one or two-CH that Isosorbide-5-Nitrae-phenylene, fluorine replace 2-Isosorbide-5-Nitrae-cyclohexylidene of being replaced by oxygen;
(F) H or F is represented.
8. according to described liquid crystal compound arbitrary in claim 3-7, it is characterized in that: in described liquid crystal compound, the mass parts of each component is as follows respectively:
Component A:5-25 part;
B component: 15-45 part;
Component C:5-45 part;
Component D:5-25 part;
Component E:5-25 part;
Component F:5-25 part.
9. contain liquid crystal display device or the liquid-crystal display of compound or the arbitrary described liquid crystal compound of claim 3-9 shown in the arbitrary described formula I of claim 1-2;
The application in liquid crystal display device or liquid-crystal display prepared by compound shown in the arbitrary described formula I of claim 1-2 or the arbitrary described liquid crystal compound of claim 3-9;
Described liquid crystal display device or liquid-crystal display are specially active array addressing liquid crystal display device or active array addressing liquid-crystal display;
Wherein, described active matrix display element be specially TN-TFT, IPS-TFT or FFS-TFT liquid crystal display device;
Described active array addressing liquid-crystal display is specially TN-TFT, IPS-TFT or FFS-TFT liquid-crystal display.
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