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CN114105966A - Liquid crystal compound and preparation method and application thereof - Google Patents

Liquid crystal compound and preparation method and application thereof Download PDF

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Publication number
CN114105966A
CN114105966A CN202010873724.2A CN202010873724A CN114105966A CN 114105966 A CN114105966 A CN 114105966A CN 202010873724 A CN202010873724 A CN 202010873724A CN 114105966 A CN114105966 A CN 114105966A
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liquid crystal
crystal compound
carbon atoms
compound
reaction
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姜卫东
戴雄
唐怡杰
程友文
李程辉
谢佩
侯斌
孙建波
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Beijing Bayi Space LCD Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • 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
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    • C09K19/00—Liquid crystal materials
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
    • C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring

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  • Optics & Photonics (AREA)
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Abstract

The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal compound and a preparation method and application thereof. The liquid crystal compound has a structure shown as a general formula (I), has a higher clearing point Cp while keeping large optical anisotropy Deltan, good rotational viscosity gamma 1, larger negative dielectric anisotropy Deltaepsilon and good liquid crystal intersolubility, improves the working temperature of the liquid crystal composition, and has good performances in thermal stability, chemical stability, optical stability, mechanics and the like, so that the driving voltage can be effectively reduced, and the response speed of a liquid crystal display device is improved.

Description

Liquid crystal compound and preparation method and application thereof
Technical Field
The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal compound and a preparation method and application thereof.
Background
The liquid crystal material has great research value and good application prospect when being used as an environmental material in the fields of information display materials, organic optoelectronic materials and the like. Liquid crystal materials have many advantages as novel display materials, such as extremely low power consumption and low driving voltage. Compared with other materials, the material also has the advantages of small volume, light weight, long service life, large display information amount, no electromagnetic radiation and the like, can almost meet the requirements of various information displays, and is particularly suitable for TFT-LCD (thin film transistor technology) products.
In the TFT active matrix system, there are mainly TN (Twisted Nematic) mode, IPS (In-Plane Switching) mode, FFS (Fringe Field Switching) mode, and VA (Vertical Alignment) mode, which are main display modes.
At present, the TFT-LCD product technology has matured, and successfully solves the technical problems of viewing angle, resolution, color saturation, brightness, etc., and large-size and medium-and small-size TFT-LCD displays have gradually occupied the mainstream status of flat panel displays in respective fields. For a dynamic picture display application, in order to realize high quality display and eliminate afterimage and tailing of a display picture, a liquid crystal material is required to have a fast response speed, and thus the liquid crystal material is required to have a rotational viscosity γ 1 as low as possible. In addition, in order to reduce power consumption of the liquid crystal display device, it is necessary to reduce the driving voltage of the liquid crystal as much as possible, and thus it is required to improve the dielectric anisotropy Δ ∈ of the liquid crystal.
The liquid crystal material is used as a core functional material of a liquid crystal display device, and is required to have a wide variety of performance parameters, particularly the rotary viscosity gamma 1 of the liquid crystal material is reduced and the dielectric anisotropy delta epsilon of the liquid crystal material is improved in order to meet the requirements of various performance parameters of the liquid crystal display device and meet the process requirements of the liquid crystal display device. In order to improve the properties of materials and enable the materials to meet new requirements, the synthesis of novel structure liquid crystal compounds and the research of structure-property relationship become important work in the field of liquid crystal.
Disclosure of Invention
The first object of the present invention is to provide a liquid crystal compound, which has a higher clearing point Cp and an improved operating temperature of a liquid crystal composition while maintaining a large optical anisotropy Δ n, a good rotational viscosity γ 1, a large negative dielectric anisotropy Δ ∈ and a good liquid crystal miscibility, and further has good thermal stability, chemical stability, optical stability, mechanical properties, and the like, thereby effectively reducing a driving voltage and improving a response speed of a liquid crystal display device.
The liquid crystal compound has a structure shown as a general formula (I):
Figure BDA0002651961160000021
wherein Z is1、Z2Each independently represents a single bond, -CH2-、-CH2-CH2-、-CH＝CH-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
r represents H, trifluoromethyl, trifluoromethoxy, difluoromethoxy, alkyl of 1 to 12 carbon atoms or alkoxy of 1 to 12 carbon atoms, wherein when R represents alkyl of 1 to 12 carbon atoms or alkoxy of 1 to 12 carbon atoms, one or more of the hydrogen atoms therein may be substituted by fluorine;
x represents O or S;
a represents a single bond or one of the following groups:
Figure BDA0002651961160000022
Figure BDA0002651961160000031
preferably, the liquid crystal compound has a structural formula:
Figure BDA0002651961160000032
wherein Z is1、Z2Each independently represents-CH2O-，-CH2CH2-，-CF2O-or-COO-;
r represents H, trifluoromethyl, trifluoromethoxy, difluoromethoxy, alkyl of 1 to 7 carbon atoms or alkoxy of 1 to 7 carbon atoms.
A is selected from one of the following groups:
Figure BDA0002651961160000033
as a further preferred embodiment, the liquid crystal compound is preferably selected from one of the following structures:
Figure BDA0002651961160000041
Figure BDA0002651961160000051
Figure BDA0002651961160000061
Figure BDA0002651961160000071
Figure BDA0002651961160000081
Figure BDA0002651961160000091
Figure BDA0002651961160000101
Figure BDA0002651961160000111
the second object of the present invention is to provide a method for preparing the above liquid crystal compound, wherein the synthetic route is as follows:
Figure BDA0002651961160000121
the method specifically comprises the following steps:
(1) to be provided with
Figure BDA0002651961160000122
And
Figure BDA0002651961160000123
by suzuki reaction, obtaining
Figure BDA0002651961160000124
(2)
Figure BDA0002651961160000125
Through the reaction of suzuki reaction with organic lithium reagent and the reaction with bromine to obtain
Figure BDA0002651961160000126
(3)
Figure BDA0002651961160000127
Reaction with ethyl mercaptopropionate to give
Figure BDA0002651961160000128
(4)
Figure BDA0002651961160000131
Through catalytic ring closure to obtain
Figure BDA0002651961160000132
Or, the synthetic route is as follows:
Figure BDA0002651961160000133
the method specifically comprises the following steps:
(1) to be provided with
Figure BDA0002651961160000134
And
Figure BDA0002651961160000135
by suzuki reaction, obtaining
Figure BDA0002651961160000136
(2)
Figure BDA0002651961160000137
Through catalytic ring closure to obtain
Figure BDA0002651961160000138
Z in the compound involved in each step1、Z2The groups A and R are as defined above.
The method of the invention, if necessary, involves conventional post-treatment, such as: extracting with dichloromethane, ethyl acetate or toluene, separating liquid, washing with water, drying, evaporating with vacuum rotary evaporator, and purifying the obtained product by vacuum distillation or recrystallization and/or chromatographic separation.
The liquid crystal compound can be stably and efficiently obtained by the preparation method.
The invention also provides a liquid crystal composition containing the liquid crystal compound. Further, the liquid crystal compound is 1 to 60% by mass, preferably 3 to 50% by mass, and more preferably 5 to 25% by mass of the liquid crystal composition.
The invention also provides the application of the liquid crystal compound and the liquid crystal composition containing the liquid crystal compound in the field of liquid crystal display, preferably the application in a liquid crystal display device. The liquid crystal display device includes, but is not limited to, TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.
The liquid crystal compound provided by the invention has a chemical main structure of dibenzothiophene or dibenzofuran, the dielectric anisotropy of the structure is larger, a tetrahydropyran group is introduced into the molecular structure of the liquid crystal compound provided by the invention, and fluorine atoms are introduced into the 4 th site and the 6 th site of the dibenzothiophene to form a strong synergistic effect, so that the negative dielectric anisotropy of the liquid crystal compound is extremely high, the clearing point is obviously improved, the optical anisotropy is higher, the rotational viscosity is moderate, the liquid crystal intersolubility is good, the low-temperature working effect is excellent, and the performances in the aspects of good thermal stability, chemical stability, optical stability, mechanics and the like are good; therefore, the driving voltage is effectively reduced, the response speed of the liquid crystal display device is improved, and the liquid crystal display device has the characteristics of good charge retention rate and the like.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
This example relates to a liquid crystal compound having the formula:
Figure BDA0002651961160000141
the synthetic route for the preparation of compound BYLC-01 is shown below:
Figure BDA0002651961160000151
the method comprises the following specific steps:
(1) synthesis of Compound BYLC-01-1:
under the protection of nitrogen, 35g of 4-tetrahydropyranylmethoxy-2, 3-difluorophenylboronic acid, 23.3g of 4-bromo-1-propoxy-2-fluorobenzene, 80ml of toluene, 40ml of deionized water, 20ml of ethanol, 23.8g of anhydrous sodium carbonate and 0.7g of tetratriphenylphosphine palladium are added into a reaction flask, and the mixture is heated and refluxed for reaction for 3 hours. Conventional work-up was carried out, and purification by chromatography, elution with n-hexane, and recrystallization with ethanol gave 33.0g of a white solid (compound BYLC-01-1), GC: 99.7%, yield: 86.8 percent.
(2) Synthesis of Compound BYLC-01-2:
under the protection of nitrogen, 31g of BYLC-01-1 and 200ml of tetrahydrofuran are added into a reaction bottle, 0.12mol of n-hexane solution of tert-butyllithium is dripped into the reaction bottle at the temperature of between 70 ℃ below zero and 80 ℃ below zero, the reaction is carried out for 1 hour after dripping, 30.0g of bromine is dripped at the temperature of between 70 ℃ below zero and 80 ℃ below zero, and then the reaction is naturally cooled to 30 ℃ below zero. 400ml of a saturated aqueous sodium sulfite solution was added for hydrolysis destruction, and conventional workup was performed, and ethanol was recrystallized to obtain 30.0g of a pale yellow solid (compound BYLC-01-2), GC: 99.3 percent and the yield is 80.3 percent;
(3) synthesis of Compound BYLC-01-3:
under the protection of nitrogen, 25.0g of compound BYLC-01-2, 10.0g of ethyl mercaptopropionate, 12.9g N, N-diisopropylethylamine, 0.31g of 2-dicyclohexylphosphine-2, 4, 6-triisopropylbiphenyl, 0.25g of tris (dibenzylideneacetone) dipalladium and 100ml of dioxane were added into a reaction flask, and the temperature was controlled at 90 ℃ to 100 ℃ for reaction for 6 hours. Conventional work-up was carried out, purification by chromatography and elution with n-hexane gave 23.0g of a pale yellow liquid (compound BYLC-01-3), GC: 95.8%, yield: 82 percent.
(4) Synthesis of Compound BYLC-01:
under the protection of nitrogen, 20.0g of compound BYLC-01-3, 9.0g of potassium tert-butoxide and 200ml of tetrahydrofuran are added into a reaction flask and reacted for 6 hours at 65-70 ℃. Conventional work-up was carried out, purification by chromatography, elution with n-hexane and crystallization with ethanol gave 12g of a white solid (compound BYLC-01), GC: 99.7%, yield: 78 percent.
The obtained white solid BYLC-01 was analyzed by GC-MS and the M/z of the product was 392.1(M +).
Example 2
This example relates to a liquid crystal compound having the formula:
Figure BDA0002651961160000161
the synthetic route for the preparation of compound BYLC-02 is shown below:
Figure BDA0002651961160000162
the method comprises the following specific steps:
(1) synthesis of Compound BYLC-02-1:
under the protection of nitrogen, 27g of 4-tetrahydropyranylmethoxy-2, 3-difluorophenylboronic acid, 24.3g of 4-bromo-3-hydroxy-2-fluorophenethyl ether, 100ml of toluene, 50ml of deionized water, 25ml of ethanol, 21.2g of anhydrous sodium carbonate and 1g of tetratriphenylphosphine palladium were added to a reaction flask, and the mixture was heated under reflux for 3 hours. Conventional work-up was carried out, and purification by chromatography, elution with n-hexane, and recrystallization with ethanol gave 33g of a white solid (compound BYLC-02-1), GC: 99.2%, yield: 86.4 percent.
(2) Synthesis of Compound BYLC-02:
19.1g (0.05mol) of Compound BYLC-02-1, 12.0g of sodium hydride and 200ml of N, N dimethylformamide were added to a reaction flask under nitrogen atmosphere, and the mixture was reacted at 130 ℃ to 140 ℃ for 6 hours. Conventional work-up was carried out, purification by chromatography, elution with n-hexane and crystallization with ethanol gave 14.8g of a white solid (compound BYLC-02), GC: 99.8%, yield: 81.7 percent.
The obtained white solid BYLC-02 was analyzed by GC-MS and the M/z of the product was 362(M +).
Example 3
Figure BDA0002651961160000171
The resulting white solid BYLC-03 was analyzed by GC-MS and the M/z of the product was 3692(M +).
Example 4
Figure BDA0002651961160000172
The obtained white solid BYLC-04 was analyzed by GC-MS and the M/z of the product was 432.1(M +).
Example 5
Figure BDA0002651961160000173
The obtained white solid BYLC-05 was analyzed by GC-MS and the M/z of the product was 392.1(M +).
Example 6
Figure BDA0002651961160000181
The resulting white solid, BYLC-06, was analyzed by GC-MS and the M/z of the product was 416.1(M +).
Example 7
Figure BDA0002651961160000182
The resulting white solid BYLC-07 was analyzed by GC-MS and the M/z of the product was 402.1(M +).
Example 8
Figure BDA0002651961160000183
The resulting white solid, BYLC-08, was analyzed by GC-MS and the M/z of the product was 376.1(M +).
Comparative example 1
The structure of the compound of this comparative example is:
Figure BDA0002651961160000184
comparative example 2
The structure of the compound of this comparative example is:
Figure BDA0002651961160000185
examples of the experiments
This experimental example relates to the determination of the relevant properties of the compounds described in the examples and in the comparative examples.
According to conventional detection methods in the art, for example, detection of Δ ε is measured using an INSTEC liquid crystal detection instrument, detection of γ 1 is measured using a viscometer, detection of Δ n is measured using an Abbe refractometer, and detection of Cp is measured using a differential thermal scanner.
And obtaining various performance parameters of the liquid crystal compound through linear fitting, wherein the specific meanings of the performance parameters are as follows:
Δ n represents optical anisotropy (25 ℃); Δ ε represents the dielectric anisotropy (25 ℃, 1000 Hz); γ 1 represents rotational viscosity (mpa.s, 25 ℃); cp stands for clearing point.
The liquid crystal compounds of examples 1-8 and comparative examples 1-2 were compared and the results are shown in Table 1.
Table 1: results of Property measurement of liquid Crystal Compound
Figure BDA0002651961160000191
Figure BDA0002651961160000201
As is apparent from the detection results in table 1, compared with the conventional negative dielectric anisotropy compound with a similar chemical structure, the liquid crystal compound provided by the present invention has a higher clearing point Cp while maintaining a large optical anisotropy Δ n, a good rotational viscosity γ 1, and a suitable negative dielectric anisotropy Δ ∈ so as to effectively improve the clearing point of the liquid crystal composition, thereby shortening the response time of the liquid crystal display device and increasing the operating temperature of the liquid crystal composition.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (8)

1. A liquid crystal compound having a structure represented by general formula (I):
Figure FDA0002651961150000011
wherein Z is1、Z2Each independently represents a single bond, -CH2-、-CH2-CH2-、-CH＝CH-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
r represents H, trifluoromethyl, trifluoromethoxy, difluoromethoxy, alkyl of 1 to 12 carbon atoms or alkoxy of 1 to 12 carbon atoms, wherein when R represents alkyl of 1 to 12 carbon atoms or alkoxy of 1 to 12 carbon atoms, one or more of the hydrogen atoms therein may be substituted by fluorine;
x represents O or S;
a represents a single bond or one of the following groups:
Figure FDA0002651961150000012
2. the liquid crystal compound according to claim 1, wherein the structural formula of the liquid crystal compound is:
Figure FDA0002651961150000021
or
Figure FDA0002651961150000022
Wherein Z is1、Z2Each independently represents-CH2O-，-CH2CH2-，-CF2O-or-COO-;
r represents H, trifluoromethyl, trifluoromethoxy, difluoromethoxy, alkyl of 1 to 7 carbon atoms or alkoxy of 1 to 7 carbon atoms;
a is selected from one of the following groups:
Figure FDA0002651961150000023
3. the liquid crystal compound of claim 1, wherein the liquid crystal compound is selected from one of the following structures:
Figure FDA0002651961150000031
Figure FDA0002651961150000041
Figure FDA0002651961150000051
Figure FDA0002651961150000061
Figure FDA0002651961150000071
Figure FDA0002651961150000081
Figure FDA0002651961150000091
Figure FDA0002651961150000101
4. a method for producing a liquid crystal compound according to any one of claims 1 to 3, characterized in that the synthetic route is as follows:
Figure FDA0002651961150000111
the method specifically comprises the following steps:
(1) to be provided with
Figure FDA0002651961150000112
And
Figure FDA0002651961150000113
by suzuki reaction, obtaining
Figure FDA0002651961150000114
(2)
Figure FDA0002651961150000115
Through the reaction of suzuki reaction with organic lithium reagent and the reaction with bromine to obtain
Figure FDA0002651961150000116
(3)
Figure FDA0002651961150000117
Reaction with ethyl mercaptopropionate to give
Figure FDA0002651961150000118
(4)
Figure FDA0002651961150000121
Through catalytic ring closure to obtain
Figure FDA0002651961150000122
Or, the synthetic route is as follows:
Figure FDA0002651961150000123
the method specifically comprises the following steps:
(1) to be provided with
Figure FDA0002651961150000124
And
Figure FDA0002651961150000125
by suzuki reaction, obtaining
Figure FDA0002651961150000126
(2)
Figure FDA0002651961150000127
Through catalytic ring closure to obtain
Figure FDA0002651961150000128
Wherein Z in the compound involved in each step1、Z2The groups A and R are as defined in claim 1 or 2.
5. A liquid crystal composition comprising the liquid crystal compound according to any one of claims 1 to 3.
6. The liquid crystal composition of claim 5, wherein the liquid crystal compound is present in the liquid crystal composition in an amount of 1 to 60% by mass, preferably 3 to 50% by mass, and more preferably 5 to 25% by mass.
7. Use of the liquid crystal compound according to any one of claims 1 to 3 or the liquid crystal composition according to claim 5 or 6 in a liquid crystal display device.
8. Use according to claim 7, wherein the liquid crystal display device is a TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.
CN202010873724.2A 2020-08-26 2020-08-26 Liquid crystal compound and preparation method and application thereof Pending CN114105966A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI808519B (en) * 2020-11-02 2023-07-11 大陸商北京八億時空液晶科技股份有限公司 A liquid crystal composition containing pyran and terphenyl and its application

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105153112A (en) * 2014-04-22 2015-12-16 默克专利股份有限公司 4,6-difluoro dibenzothiophene derivates

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105153112A (en) * 2014-04-22 2015-12-16 默克专利股份有限公司 4,6-difluoro dibenzothiophene derivates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI808519B (en) * 2020-11-02 2023-07-11 大陸商北京八億時空液晶科技股份有限公司 A liquid crystal composition containing pyran and terphenyl and its application

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