CN106929036A - A kind of liquid-crystal compounds and its application containing cyclopenta and trifluoromethyl structure - Google Patents
A kind of liquid-crystal compounds and its application containing cyclopenta and trifluoromethyl structure Download PDFInfo
- Publication number
- CN106929036A CN106929036A CN201511020748.9A CN201511020748A CN106929036A CN 106929036 A CN106929036 A CN 106929036A CN 201511020748 A CN201511020748 A CN 201511020748A CN 106929036 A CN106929036 A CN 106929036A
- Authority
- CN
- China
- Prior art keywords
- liquid
- nitrae
- isosorbide
- crystal compounds
- phenylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 C*c1c(C(F)(F)F)c(F)c(*)cc1 Chemical compound C*c1c(C(F)(F)F)c(F)c(*)cc1 0.000 description 2
- QQIUWKSJCNTODY-UHFFFAOYSA-N CC(CCCC(C1CC(F)(F)F)O)C1F Chemical compound CC(CCCC(C1CC(F)(F)F)O)C1F QQIUWKSJCNTODY-UHFFFAOYSA-N 0.000 description 1
- UTTMZVYXMNZXPT-UHFFFAOYSA-N CCC(CC1)CC1C(C)C Chemical compound CCC(CC1)CC1C(C)C UTTMZVYXMNZXPT-UHFFFAOYSA-N 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
Abstract
The present invention relates to a kind of new negative dielectric anisotropic liquid crystal compound containing cyclopenta and trifluoromethyl structure and the liquid-crystal composition including the liquid-crystal compounds.The liquid-crystal compounds has the advantages that negative dielectric anisotropic higher, good liquid crystal intersolubility, relatively low rotary viscosity, and these exactly improve required for liquid crystal material, with important application value.Having used the liquid-crystal compounds or the composition containing the liquid-crystal compounds correspondingly has high negative dielectric anisotropic, rotary viscosity is low, so as to effectively reduce driving voltage, the response speed of liquid crystal display device is improve, while having the features such as optical anisotropy numerical value is moderate, electric charge conservation rate is high.
Description
Technical field
The present invention relates to liquid crystal display material field, more particularly to a kind of liquid-crystal compounds, composition and its application, more
Say body, the present invention relates to a kind of new negative dielectric anisotropic liquid crystal compound containing cyclopenta and trifluoromethyl structure with
And the liquid-crystal composition including the liquid-crystal compounds.
Background technology
Application of the liquid crystal material as environmentally conscious materialses in the fields such as presentation of information material, organic optoelectronic material has pole
Big researching value and fine application prospect.Liquid crystal material has many advantages as new display material, and such as power consumption is extremely low, drives
Dynamic voltage is low.Simultaneously compared with other materials, also with small volume, lightweight, long-life, display information amount it is big, without electromagnetism spoke
The advantages of penetrating, is almost adapted to the requirement of various presentation of information, especially in TFT-LCD (thin-film transistor technologies) product side
Face.
Liquid crystal material requirement possesses good chemically and thermally stability, good to electric field and the stability of electromagnetic radiation,
Nematic temperature range wider, appropriate refractive index, dielectric anisotropy, response speed and voltage high keep faster
Rate.
At present, TFT-LCD product technologies are ripe, successfully solve visual angle, resolution ratio, color saturation and brightness etc.
Technical barrier, large scale and small-medium size TFT-LCD displays have gradually occupied the main flow of flat-panel monitor in respective field
Status.But the requirement to Display Technique is constantly being improved always, it is desirable to which liquid crystal display is realized faster responding, and reduces
Driving voltage, with the development of Display Technique, requirement higher is it is also proposed to liquid crystal material, especially to reduce the aspects such as power consumption
It is, in quick response, to reduce driving voltage, reduces the aspects such as power consumption.
In order to the performance for improving material adapts it to new requirement, the synthesis of new structure liquid-crystal compounds and structure-property
An important process of the research as field of liquid crystals of energy relation.
The content of the invention
The first object of the present invention is to provide a kind of liquid-crystal compounds of new negative dielectric anisotropic, compound tool
There are negative dielectric anisotropic higher, good liquid crystal intersolubility, relatively low rotary viscosity, these exactly improve liquid
Required for brilliant material, with important application value.
Liquid-crystal compounds of the present invention, with following structure：
In formula I, R1Represent H or with the 1-10 alkyl of carbon atom, R2Represent that there is the alkyl of 1-10 carbon atom
Or alkoxy, ring A represents Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms,
Ring B represents Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms, m be 0,1 or
2, n is 0 or 1, and is 0 when m, n difference.
Preferably, in formula I, R1Represent H or with the 1-5 alkyl of carbon atom, R2Represent that there is 1-5 carbon atom
Alkyl or alkoxy, ring A represent Isosorbide-5-Nitrae that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom be replaced by fluorine atoms-
Phenylene, ring B represents Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms, m
Be 0,1 or 2, n are 0 or 1, and m, n it is different when be 0.
As preferred technical scheme, in formula I, R1Represent H or with the 1-5 alkyl of carbon atom, R2Represent tool
There are 1-5 the alkyl or alkoxy of carbon atom, ring A represents that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-2 hydrogen atom are former by fluorine
Isosorbide-5-Nitrae-the phenylene of son substitution, ring B represents what Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-2 hydrogen atom were replaced by fluorine atoms
Isosorbide-5-Nitrae-phenylene, m is 0 or 1, n are 0 or 1, and is 0 when m, n difference.
Used as the preferred embodiment of the present invention, in formula I, ring A represents Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene, ring B
Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-2 hydrogen atom are replaced by fluorine atoms is represented, m is 0 or 1, n are
1。
Used as further preferred technical scheme, the liquid-crystal compounds is selected from one kind of following compound：
In I-1~I-12, R1Represent H or with the 1-5 alkyl of carbon atom, R2Represent that there is the alkane of 1-5 carbon atom
Base or alkoxy.
Used as implementation method still more preferably, in formula I, ring A represents Isosorbide-5-Nitrae-cyclohexylidene, ring B represent Isosorbide-5-Nitrae-
Isosorbide-5-Nitrae-phenylene that phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 2 hydrogen atoms are replaced by fluorine atoms, m is 0 or 1, n are 1.
Used as preferred forms of the invention, the liquid-crystal compounds is selected from one kind of following compound：
The second object of the present invention is to provide the preparation method of the liquid-crystal compounds.
Logical formula (I)Synthetic route is as follows：
Specifically include following steps：
(1)Reduced by reducing agent, obtained
(2)Reacted with organolithium reagent, then reacted with borate, obtained
(3)By oxidation reaction, obtain
(4)WithIt is raw material reaction, obtains
Arrive
Wherein, the R in compound involved by each step1、R2, m, n, ring A, R in ring B and gained liquid-crystal compounds product1、
R2, m, n, ring A, ring B represent group it is corresponding.
Step described in the above method
The step 1) inIt is 1 with the molar ratio of reducing agent:
0.5~3.0, reaction temperature -30~80 DEG C；
Wherein, the reducing agent is selected from one or more in sodium borohydride, potassium borohydride, red aluminum or Lithium Aluminium Hydride.
The step 2) inOrganolithium reagent is 1: 1.0~1.8 with the molar ratio of borate:
1.0~2.0, reaction temperature -50~-100 DEG C；
Wherein, the organolithium reagent is selected from n-BuLi, s-butyl lithium, tert-butyl lithium or n-BuLi and potassium tert-butoxide
In one or more, the borate be selected from trimethylborate, triisopropyl borate ester, butyl borate or the isobutyl ester of boric acid three
In one or more.
The step 3) in,It is 1: 1.0~4.0 with the molar ratio of oxidant, instead
Answer 40~80 DEG C of temperature；
Above-mentioned oxidant may be selected from hydrogen peroxide or metachloroperbenzoic acid, preferably hydrogen peroxide.
The step 4) in, With
The molar ratio of DIAD is 1: 1.0~2.0: 1.0~3.0, reaction temperature -10~50 DEG C.
Method of the present invention, can be related to conventional post processing when necessary, and the conventional post processing is specific such as：Use dichloro
Methane, ethyl acetate or toluene extraction, point liquid, washing are dried, vacuum rotary evaporator evaporation, products therefrom vacuum distillation
Or recrystallization and/or chromatography purification, you can.
Can be stablized using above-mentioned preparation method, be efficiently obtained liquid-crystal compounds of the present invention.
The third object of the present invention is composition of the protection containing the liquid-crystal compounds.The liquid-crystal compounds is in combination
Mass percent in thing is 1~60%, preferably 3~50%, more preferably 5~25%.
The fourth object of the present invention is that the protection liquid-crystal compounds and the composition containing the liquid-crystal compounds exist
The application of field of liquid crystal display, the application preferably in liquid crystal display device.Described liquid crystal display device include but not
It is limited to TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.Use the liquid-crystal compounds or contain the LCD compound
The composition of thing has high negative dielectric anisotropic, and rotary viscosity is low, so as to effectively reduce driving voltage, improves liquid crystal
The response speed of display device, while having the features such as optical anisotropy numerical value is moderate, electric charge conservation rate is high.
Specific embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
The raw material unless otherwise instructed, can be obtained from open commercial sources.
According to the common detection methods of this area, the various performance parameters of liquid-crystal compounds are obtained by linear fit, its
In, the concrete meaning of each performance parameter is as follows：
△ n represent optical anisotropy (25 DEG C)；△ ε represent dielectric anisotropy (25 DEG C, 1000Hz)；γ 1 represents rotation
Turn viscosity (mPa.s, 25 DEG C).
Embodiment 1
The structural formula of liquid-crystal compounds is：
The synthetic line of prepare compound BYLC-01 is as follows：
Comprise the following steps that：
(1) synthesis of compound BYLC-01-1：
Under nitrogen protection, controlled to the 20.8g fluoro- 3- trifluoromethyls phenetoles of 2-, 150ml tetrahydrofurans is added in reaction bulb
- 70~-80 DEG C of hexane solutions of dropwise addition 0.12mol n-BuLis of temperature, drop finishes insulation reaction 1 hour, temperature control -70~-80 DEG C
15.9g trimethylborates are added dropwise, then rise again naturally to -30 DEG C.Add 2M aqueous hydrochloric acid solutions 300ml to be acidified, carry out often
Rule post processing, petroleum ether is recrystallized to give light yellow solid (compound BYLC-01-1) 23.2g, HPLC：98.5%, yield
92%；
(2) synthesis of compound BYLC-01-2：
To 20g compound BYLC-01-1 and 100ml tetrahydrofurans are added in reaction bulb, backflow is lower to be added dropwise 0.16mol dioxygens
Water, drop finishes back flow reaction 1 hour.Conventional post processing is carried out, pale pink solid (compound BYLC-01-2) 16.7g, GC is obtained：
99.2%, yield 94%；
(3) synthesis of compound BYLC-01-3：
To 4.6g lithium aluminium hydride reductions and 300ml tetrahydrofurans is added in reaction bulb, 38.0g cyclopentylbenzoic acids and 80ml is added dropwise
The solution of tetrahydrofuran composition, drop finishes back flow reaction 3 hours, adds aqueous sodium potassium tartrate that reaction is quenched, after carrying out routine
Treatment, obtains white solid (compound BYLC-01-3) 26.4g, HPLC：99.5%, yield 75%；
(4) synthesis of compound BYLC-01：
Under nitrogen protection, to addition 12.2g compounds BYLC-01-3,15.5g BYLC-01-2,21.8g tri- in reaction bulb
Phenylphosphine, 100ml dichloromethane, temperature control -5~5 DEG C are added dropwise the solution of 16.7g DIAD and 30ml dichloromethane composition, and drop finishes protects
Temperature reaction 0.5 hour, is heated up naturally, room temperature reaction 3 hours, and addition 100ml water quenchings are gone out reaction, carry out conventional post processing, are obtained
White solid (compound BYLC-01) 23.1g, GC：99.6%, yield 87.4%；
Gained white solid BYLC-01 is analyzed using GC-MS, the m/z of product is 382.1 (M+).
1H-NMR(300MHz,CDCl3):1.25-2.10(m,11H),2.45-2.94(m,1H),3.75-4.05(m,2H),
5.01-5.63(m,2H),6.25-7.30(m,6H)。
Embodiment 2
The structural formula of liquid-crystal compounds is：
The synthetic line of prepare compound BYLC-02 is as follows：
Comprise the following steps that：
(1) synthesis of compound BYLC-02-1：
To in reaction bulb add 6.8g lithium aluminium hydride reductions and 300ml tetrahydrofurans, be added dropwise 29.4g cyclopentyl cyclohexyls formic acid and
The solution of 80ml tetrahydrofurans composition, drop finishes back flow reaction 3 hours, adds aqueous sodium potassium tartrate that reaction is quenched, and carries out often
Rule post processing, obtains white solid (compound BYLC-02-1) 21.0g, HPLC：99.3%, yield 77%；
(2) synthesis of compound BYLC-02：
Under nitrogen protection, to addition 18.2g compounds BYLC-02-1,22.4g BYLC-01-2,26.2g tri- in reaction bulb
Phenylphosphine, 100ml dichloromethane, temperature control -5~5 DEG C are added dropwise the solution of 20.2g DIAD and 30ml dichloromethane composition, and drop finishes protects
Temperature reaction 0.5 hour, is heated up naturally, room temperature reaction 3 hours, and addition 100ml water quenchings are gone out reaction, carry out conventional post processing, are obtained
White solid (compound BYLC-02) 33.0g, GC：99.5%, yield 85.2%；
Gained white solid BYLC-02 is analyzed using GC-MS, the m/z of product is 388.1 (M+).
1H-NMR(300MHz,CDCl3):1.25-2.13(m,22H),3.75-4.10(m,4H),6.23-6.87(m,2H)。
Embodiment 3
The structural formula of liquid-crystal compounds is：
The synthetic line of prepare compound BYLC-03 is as follows：
Comprise the following steps that：
(1) synthesis of compound BYLC-03-1：
To 4.6g lithium aluminium hydride reductions and 300ml tetrahydrofurans is added in reaction bulb, 27.2g cyclopentyl cyclohexyl benzoic acid is added dropwise
The solution constituted with 80ml tetrahydrofurans, drop finishes back flow reaction 3 hours, adds aqueous sodium potassium tartrate that reaction is quenched, and carries out
Conventional post processing, obtains white solid (compound BYLC-03-1) 20.5g, HPLC：99.6%, yield 79.5%；
(2) synthesis of compound BYLC-03：
Under nitrogen protection, to addition 20.0g compounds BYLC-03-1,19.1g BYLC-01-2,30.5g tri- in reaction bulb
Phenylphosphine, 100ml dichloromethane, temperature control -5~5 DEG C are added dropwise the solution of 23.5g DIAD and 30ml dichloromethane composition, and drop finishes protects
Temperature reaction 0.5 hour, is heated up naturally, room temperature reaction 3 hours, and addition 100ml water quenchings are gone out reaction, carry out conventional post processing, are obtained
White solid (compound BYLC-03) 30.2g, GC：99.7%, yield 84.2%；
Gained white solid BYLC-03 is analyzed using GC-MS, the m/z of product is 464.2 (M+).
1H-NMR(300MHz,CDCl3):1.25-2.03 (m, 21H), 2.45-2.87 (m, 1H), 3.55-4.05 (m, 2H),
5.10-5.45(m,2H),6.13-7.25(m,6H)。
Embodiment 4
The structural formula of liquid-crystal compounds is：
The synthetic line of prepare compound BYLC-04 is as follows：
(1) synthesis of compound BYLC-04-1：
To 3.6g lithium aluminium hydride reductions and 300ml tetrahydrofurans is added in reaction bulb, 33.4g cyclopenta dicyclohexyl formic acid is added dropwise
The solution constituted with 80ml tetrahydrofurans, drop finishes back flow reaction 3 hours, adds aqueous sodium potassium tartrate that reaction is quenched, and carries out
Conventional post processing, obtains white solid (compound BYLC-04-1) 26.1g, HPLC：99.7%, yield 82.3%；
(2) synthesis of compound BYLC-04：
Under nitrogen protection, to addition 25g compounds BYLC-04-1,26g BYLC-01-2,29.8g triphenyl in reaction bulb
Phosphine, 100ml dichloromethane, temperature control -5~5 DEG C are added dropwise the solution of 23.2g DIAD and 30ml dichloromethane composition, and Bi Baowen is anti-for drop
Answer 0.5 hour, heat up naturally, room temperature reaction 3 hours adds 100ml water quenchings to go out reaction, carries out conventional post processing, obtains white
Solid (compound BYLC-04) 36.6g, GC：99.8%, yield 82.7%；
Gained white solid BYLC-04 is analyzed using GC-MS, the m/z of product is 470.2 (M+).
1H-NMR(300MHz,CDCl3):1.25-2.03 (m, 32H), 3.53-4.05 (m, 4H), 6.13-6.95 (m, 2H).
Embodiment 5
According to the technical scheme of embodiment 1,2,3,4, it is only necessary to simply replace corresponding raw material, any substance is not changed
Operation, can synthesize following liquid-crystal compounds.
Experimental example 1
By compound BYLC-01 and comparative example 1, the liquid-crystal compounds performance parameter of comparative example 2 obtained by embodiment 1
Data carry out contrast arrangement, and testing result is as shown in table 1：
Table 1：The performance test results of liquid-crystal compounds
By the testing result of table 1, it is apparent that the liquid-crystal compounds and traditional chemistry similar knot of present invention offer
The negative dielectric anisotropic compound phase ratio of structure, it is relatively small with negative dielectric anisotropic △ ε, rotary viscosity γ 1 higher,
These exactly improve required for liquid crystal material, can effectively improve the dielectric anisotropy △ ε of liquid-crystal composition, reduce and drive
Voltage, the faster liquid-crystal composition of the speed that meets with a response.
Experimental example 2
Compound in embodiment 4 and comparative example 3, the liquid-crystal compounds performance parameter data of comparative example 4 are carried out into contrast whole
Reason, testing result is as shown in table 2：
Table 2：The performance test results of liquid-crystal compounds
By the testing result of table 2, it is apparent that the liquid-crystal compounds and traditional chemistry similar knot of present invention offer
The negative dielectric anisotropic compound phase ratio of structure, it is relatively small with negative dielectric anisotropic △ ε, rotary viscosity γ 1 higher,
These exactly improve required for liquid crystal material, can effectively improve the dielectric anisotropy △ ε of liquid-crystal composition, reduce and drive
Voltage, the faster liquid-crystal composition of the speed that meets with a response.
Additionally, found after herein described compound is particularly applicable in the liquid-crystal composition of conventional system, it can be with
The dielectric anisotropy △ ε of liquid-crystal composition are significantly improved, while the relatively low rotary viscosity γ 1 of holding and appropriate refractive index are each
Anisotropy △ n, gained liquid-crystal composition has significant quick response feature and low voltage drive feature.
Although above the present invention is described in detail with a general description of the specific embodiments,
On the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Cause
This, these modifications or improvements, belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (10)
1. a kind of liquid-crystal compounds of negative dielectric anisotropic, it is characterised in that with following structure：
In formula I, R1Represent H or with the 1-10 alkyl of carbon atom, R2Represent that there is the alkyl or alkane of 1-10 carbon atom
Epoxide, ring A represents Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms, ring B
Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms is represented, m is 0,1 or 2, n
It is 0 or 1, and is 0 when m, n difference.
2. liquid-crystal compounds according to claim 1, it is characterised in that R1Represent H or with the 1-5 alkyl of carbon atom,
R2Represent that there is the alkyl or alkoxy of 1-5 carbon atom, ring A represents that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-2 hydrogen are former
Isosorbide-5-Nitrae-phenylene that son is replaced by fluorine atoms, ring B represents that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-2 hydrogen atom are former by fluorine
Isosorbide-5-Nitrae-the phenylene of son substitution, m is 0 or 1, n are 0 or 1, and is 0 when m, n difference.
3. liquid-crystal compounds according to claim 1, it is characterised in that ring A represents Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-Asia hexamethylene
Base, ring B represents Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-2 hydrogen atom are replaced by fluorine atoms, m be 0 or
1, n is 1.
4. liquid-crystal compounds according to claim 1, it is characterised in that the liquid-crystal compounds is selected from following compound
It is a kind of：
In I-1~I-12, R1Represent H or with the 1-5 alkyl of carbon atom, R2Represent have the alkyl of 1-5 carbon atom or
Alkoxy.
5. liquid-crystal compounds according to claim 1, it is characterised in that ring A represents Isosorbide-5-Nitrae-cyclohexylidene, and ring B represents 1,
Isosorbide-5-Nitrae-phenylene that 4- phenylenes, Isosorbide-5-Nitrae-cyclohexylidene or 2 hydrogen atoms are replaced by fluorine atoms, m is 0 or 1, n are 1.
6. liquid-crystal compounds according to claim 1, it is characterised in that the liquid-crystal compounds is selected from following compound
It is a kind of：
7. one kind has the preparation method of the liquid-crystal compounds of formula (I) structure, it is characterised in that comprise the following steps：
(1)Reduced by reducing agent, obtained
(2)Reacted with organolithium reagent, then reacted with borate, obtained
(3)By oxidation reaction, obtain
(4)WithIt is raw material reaction, obtains
Wherein, the R in compound involved by each step1、R2, m, n, ring A, R in ring B and gained liquid-crystal compounds product1、R2、m、
The group that n, ring A, ring B are represented is corresponding.
8. any liquid-crystal compounds of claim 1-6 in TN, ADS, VA, PSVA, FFS or IPS liquid crystal display should
With.
9. a kind of liquid-crystal composition, it is characterised in that comprising any liquid-crystal compounds of claim 1-6, and the liquid crystal
Compound is 1~60%, preferably 3~50%, more preferably 5~25% in the mass percent of combination species.
10. application of the liquid-crystal composition described in claim 9 in TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201511020748.9A CN106929036A (en) | 2015-12-30 | 2015-12-30 | A kind of liquid-crystal compounds and its application containing cyclopenta and trifluoromethyl structure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201511020748.9A CN106929036A (en) | 2015-12-30 | 2015-12-30 | A kind of liquid-crystal compounds and its application containing cyclopenta and trifluoromethyl structure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106929036A true CN106929036A (en) | 2017-07-07 |
Family
ID=59442429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201511020748.9A Pending CN106929036A (en) | 2015-12-30 | 2015-12-30 | A kind of liquid-crystal compounds and its application containing cyclopenta and trifluoromethyl structure |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106929036A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108690641A (en) * | 2018-07-27 | 2018-10-23 | 烟台丰蓬液晶材料有限公司 | Liquid crystal composition containing bis-trifluoromethyl compound and negative dielectric anisotropy and application thereof |
| CN108795444A (en) * | 2018-07-27 | 2018-11-13 | 烟台丰蓬液晶材料有限公司 | Liquid crystal compound with negative dielectric anisotropy and preparation method and application thereof |
| CN109796990A (en) * | 2017-11-16 | 2019-05-24 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal compounds and liquid crystal compound and its display device containing lateral trifluoromethyl |
| CN113214083A (en) * | 2021-04-06 | 2021-08-06 | 北京八亿时空液晶科技股份有限公司 | Self-alignment polymerizable compound and application thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003024903A1 (en) * | 2001-09-14 | 2003-03-27 | Qinetiq Limited | Liquid crystal compounds with branched or cyclic end groups |
| JP2009007485A (en) * | 2007-06-28 | 2009-01-15 | Mitsubishi Chemicals Corp | Dichroic pigment, and liquid crystal composition, liquid crystal element using the same |
| CN103030534A (en) * | 2012-11-23 | 2013-04-10 | 石家庄诚志永华显示材料有限公司 | Negative liquid crystal compound containing 2,3-difluorophenyl group, and preparation method and application thereof |
| CN103074073A (en) * | 2012-12-20 | 2013-05-01 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropic liquid crystal mixture |
| CN104263383A (en) * | 2014-10-10 | 2015-01-07 | 石家庄诚志永华显示材料有限公司 | Liquid crystal medium and application |
| CN104513666A (en) * | 2014-10-10 | 2015-04-15 | 石家庄诚志永华显示材料有限公司 | Liquid crystal medium and application |
-
2015
- 2015-12-30 CN CN201511020748.9A patent/CN106929036A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003024903A1 (en) * | 2001-09-14 | 2003-03-27 | Qinetiq Limited | Liquid crystal compounds with branched or cyclic end groups |
| JP2009007485A (en) * | 2007-06-28 | 2009-01-15 | Mitsubishi Chemicals Corp | Dichroic pigment, and liquid crystal composition, liquid crystal element using the same |
| CN103030534A (en) * | 2012-11-23 | 2013-04-10 | 石家庄诚志永华显示材料有限公司 | Negative liquid crystal compound containing 2,3-difluorophenyl group, and preparation method and application thereof |
| CN103074073A (en) * | 2012-12-20 | 2013-05-01 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropic liquid crystal mixture |
| CN104263383A (en) * | 2014-10-10 | 2015-01-07 | 石家庄诚志永华显示材料有限公司 | Liquid crystal medium and application |
| CN104513666A (en) * | 2014-10-10 | 2015-04-15 | 石家庄诚志永华显示材料有限公司 | Liquid crystal medium and application |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109796990A (en) * | 2017-11-16 | 2019-05-24 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal compounds and liquid crystal compound and its display device containing lateral trifluoromethyl |
| CN109796990B (en) * | 2017-11-16 | 2022-09-09 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing lateral trifluoromethyl, liquid crystal mixture and display device thereof |
| CN108690641A (en) * | 2018-07-27 | 2018-10-23 | 烟台丰蓬液晶材料有限公司 | Liquid crystal composition containing bis-trifluoromethyl compound and negative dielectric anisotropy and application thereof |
| CN108795444A (en) * | 2018-07-27 | 2018-11-13 | 烟台丰蓬液晶材料有限公司 | Liquid crystal compound with negative dielectric anisotropy and preparation method and application thereof |
| CN113214083A (en) * | 2021-04-06 | 2021-08-06 | 北京八亿时空液晶科技股份有限公司 | Self-alignment polymerizable compound and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106883861B (en) | A kind of liquid-crystal compounds, composition and its application | |
| CN107541220B (en) | A kind of liquid-crystal compounds and the preparation method and application thereof | |
| CN109206400B (en) | Liquid crystal compound containing dibenzothiophene structure and application thereof | |
| CN109423297B (en) | Dibenzothiophene liquid crystal compound and preparation method and application thereof | |
| CN106883862B (en) | A kind of liquid-crystal compounds, composition and its application | |
| CN106811208B (en) | A kind of liquid-crystal compounds, composition and its application | |
| CN106811209B (en) | A kind of liquid-crystal compounds, composition and its application | |
| CN109207160B (en) | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof | |
| CN109423296B (en) | Dibenzothiophene negative dielectric anisotropy compound and preparation method and application thereof | |
| CN106929036A (en) | A kind of liquid-crystal compounds and its application containing cyclopenta and trifluoromethyl structure | |
| CN108728112A (en) | A kind of liquid-crystal compounds of negative dielectric anisotropic and the preparation method and application thereof | |
| CN111825534A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN109082281B (en) | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof | |
| CN107400517B (en) | Cyclopentyl negative dielectric anisotropy liquid crystal compound, composition and application | |
| CN109207158A (en) | A kind of liquid-crystal compounds of the negative dielectric anisotropic containing alkenes and its application | |
| CN107286953B (en) | Cyclopentyl negative dielectric anisotropy liquid crystal compound and composition and application thereof | |
| CN106146250B (en) | A kind of liquid-crystal compounds, composition and its application | |
| CN106398717B (en) | A kind of epoxypentyl class liquid-crystal compounds and preparation method and application | |
| CN107286950A (en) | A kind of cyclopenta liquid-crystal compounds, composition and its application | |
| CN109423298B (en) | Novel dibenzothiophene liquid crystal compound and preparation method and application thereof | |
| CN114105941A (en) | Novel liquid crystal compound and preparation method and application thereof | |
| CN114686242A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN106833676B (en) | Cyclopropyl liquid crystal compound and preparation method and application thereof | |
| CN107345138B (en) | Isobutyl liquid crystal compound, preparation method and application | |
| CN110628439A (en) | High-performance liquid crystal compound and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170707 |