CN111778040B - Liquid crystal compound and preparation method and application thereof - Google Patents
Liquid crystal compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN111778040B CN111778040B CN201910266906.0A CN201910266906A CN111778040B CN 111778040 B CN111778040 B CN 111778040B CN 201910266906 A CN201910266906 A CN 201910266906A CN 111778040 B CN111778040 B CN 111778040B
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- crystal compound
- compound
- crystal composition
- group
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- 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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
-
- 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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
- C09K2019/0414—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—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
Abstract
The invention relates to a liquid crystal compound and a preparation method and application thereof. The liquid crystal compound has a structural formula shown in a general formula (I). The liquid crystal compound has larger vertical dielectric anisotropy, and the integral dielectric anisotropy is positive and is approximately 0, so that the driving voltage is effectively reduced, and the response speed of a liquid crystal display device is improved; meanwhile, the liquid crystal compound also has the advantages of high penetration rate, moderate optical anisotropy, high bright point, high charge retention rate, moderate rotary viscosity and liquid crystal intersolubility, excellent low-temperature working effect, good thermal stability, chemical stability, optical stability, mechanical property and the like.
Description
Technical Field
The invention belongs to the technical field of liquid crystal materials, and relates to a liquid crystal compound, and a preparation method and application thereof.
Background
In recent years, liquid crystal display devices have been developed more and more rapidly, and various types such as a small liquid crystal display device for vehicles, a portable liquid crystal display device, an ultra-thin liquid crystal display device, and the like have been developed. Developments in the field are progressing, and in the case of a television, for example, it is characterized by light weight, small space occupation, convenience in movement, and also a notebook-type personal computer, a mobile phone, and the like.
The liquid crystal material is used as an environmental material and has great research value and good application prospect in the fields of information display materials, organic optoelectronic materials and the like. 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. However, the requirements for display technology are continuously increasing, and liquid crystal displays are required to achieve faster response, reduce driving voltage to reduce power consumption, and the like, and liquid crystal materials are also required to have low voltage driving, fast response, wide temperature range and good low temperature stability.
The liquid crystal material plays an important role in improving the performance of the liquid crystal display, and in order to improve the performance of the material and enable the material to adapt to new requirements, the synthesis, structure and performance relationship of the liquid crystal compound with a novel structure become an important work in the field of liquid crystal.
Disclosure of Invention
The present invention provides a liquid crystal compound having a large vertical dielectric anisotropy and a positive overall dielectric anisotropy, which is approximately 0, thereby effectively reducing a driving voltage and increasing a response speed of a liquid crystal display device; meanwhile, the liquid crystal compound also has the advantages of high penetration rate, moderate optical anisotropy, high bright point, high charge retention rate, moderate rotary viscosity and liquid crystal intersolubility, excellent low-temperature working effect, good thermal stability, chemical stability, optical stability, mechanical property and the like.
The liquid crystal compound has a structural formula shown as a general formula (I):
in the general formulaIn I, R1Denotes CF3Or OCF3；
R2Represents a (straight or branched) alkyl or alkoxy group having 1 to 10 carbon atoms, a cyclopropyl group, a cyclobutyl group or a cyclopentyl group; wherein H in the alkyl or alkoxy group may be substituted by halogen, one or more-CH2-may each be independently substituted with-CH ═ CH-, or-O-, but requires that the O atoms are not directly attached to each other;
ring A and ring B are the same or different and each independently represents 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-phenylene; wherein 1 to 4 hydrogen atoms of the 1, 4-cyclohexylene group may be substituted with fluorine atoms; 1 to 4 hydrogen atoms in the 1, 4-phenylene group may be substituted by fluorine atoms or 1 to 2-CH-groups may be substituted by nitrogen atoms;
Z1represents a single bond, -CH2-or-CH2CH2；
Z2Represents a single bond, -O-, -CH2-、-CH2CH2-or-CH2O-；
m and n are the same or different and each independently represents 0, 1 or 2, and 0< m + n.ltoreq.3.
Preferably, in the formula (I), R2Represents an alkyl or alkoxy group having 1 to 5 carbon atoms, a cyclopropyl group, a cyclobutyl group or a cyclopentyl group; wherein H in the alkyl or alkoxy group may be substituted by F;
ring A and ring B are the same or different and each independently represents 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-phenylene; wherein 1 to 2 hydrogen atoms in the 1, 4-phenylene group may be substituted with fluorine atoms;
m and n are the same or different and each independently represents 0, 1 or 2, and 0< m + n ≦ 2.
Preferably, the compounds of the present invention have the structural formula:
wherein R1Denotes CF3Or OCF3；R2Represents a group having 1 to 5 carbon atomsAlkyl or alkoxy, cyclopropyl, cyclobutyl or cyclopentyl; wherein H in the alkyl or alkoxy group may be substituted by F;
Z1represents a single bond, -CH2-or-CH2CH2；
Z2Represents a single bond, -O-, -CH2-、-CH2CH2-or-CH2O-。
Further preferably, the compound of the present invention has a structural formula:
another object of the invention is to protect the preparation of the compounds according to the invention, which is prepared by the following route:
the method specifically comprises the following steps:
Wherein X represents I, Br or Cl, and R in the compound involved in each step1、R2、m、n、Z1、Z2Ring A, ring B and R in the general formula (I) of the compound1、R2、m、n、Z1、Z2The groups represented by the ring A and the ring B correspond to each other.
In the above-mentioned method, the first step of the method,
and
the feeding molar ratio of (A) to (B) is 1.0: 1.0 to 1.5;
preferably, the reaction temperature can be 60-140 ℃;
in the above-mentioned method, the first step of the method,
can be synthesized by publicly available commercial methods or by methods known per se in the literature.
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 compound of the invention can be stably and efficiently obtained by the preparation method.
A third object of the invention is to protect compositions containing said compounds. The mass percentage of the compound in the composition is 0.01-60%, preferably 0.1-50%, and more preferably 0.1-40%.
The fourth object of the present invention is to protect the use of said compounds and compositions containing said compounds in the field of liquid crystal displays, preferably in liquid crystal display devices. The liquid crystal display device includes, but is not limited to, a VA, TN, STN, FFS or IPS liquid crystal display.
The invention has the following beneficial effects:
the liquid crystal compound has larger vertical dielectric anisotropy, larger penetration rate, high-definition bright points, moderate rotary viscosity and liquid crystal intersolubility, excellent low-temperature working effect, good thermal stability, chemical stability, optical stability, mechanical property and other properties; 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 moderate optical anisotropy value, high 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.
The starting materials are commercially available from the open literature unless otherwise specified.
According to the conventional detection method in the field, various performance parameters of the liquid crystal compound are obtained through linear fitting, wherein the specific meanings of the performance parameters are as follows:
Δ ε represents the dielectric anisotropy (25 ℃, 1000 Hz); ε ^ represents a dielectric constant (25 ℃ C., 1000Hz) in the vertical molecular axis direction.
Example 1
The structural formula of the liquid crystal compound is as follows:
the synthetic route for the preparation of compound BYLC-01 is shown below:
the method comprises the following specific steps:
synthesis of Compound BYLC-01:
under the protection of nitrogen, 66.6g of compound BYLC-01-1, 32.8g of propylphenylboronic acid, 200ml of N, N-dimethylformamide, 100ml of deionized water, 27.6g of anhydrous potassium carbonate and 0.4g of palladium tetratriphenylphosphine were added into a reaction flask, and the mixture was heated to 70 ℃ for reaction for 3 hours. Conventional work-up was carried out, and purification by chromatography, elution with n-hexane, and recrystallization with ethanol gave 58.4g of a white solid (compound BYLC-01), 99.7% GC, yield: 78.6 percent.
The obtained white solid BYLC-01 was analyzed by GC-MS and the M/z of the product was 372(M +).
1H-NMR(300MHz,CDCl3):0.15-1.85(m,5H),1.95-2.95(m,6H),4.55-5.35(m,1H), 6.25-7.65(m,5H)。
Example 2
The structural formula of the liquid crystal compound is as follows:
synthesis of Compound BYLC-02:
under the protection of nitrogen, 40.5g of compound BYLC-02-1, 21.7g of propylcyclohexylboronic acid, 150ml of N, N-dimethylformamide, 80ml of deionized water, 17.0g of anhydrous potassium carbonate and 0.3g of tetrakistriphenylphosphine palladium were added to a reaction flask, and the mixture was heated to 100 ℃ for reaction for 3 hours. Conventional work-up was carried out, and purification by chromatography, elution with n-hexane, and recrystallization with ethanol gave 37.1g of a white solid (compound BYLC-02), 99.8% GC, yield: 82.5 percent.
The resulting white solid BYLC-02 was analyzed by GC-MS and the M/z of the product was 378(M +).
1H-NMR(300MHz,CDCl3):0.55-1.95(m,17H),2.15-2.95(m,4H),3.25-4.65(m,1H),6.35-7.35( m,1H)。
Example 3
The structural formula of the liquid crystal compound is as follows:
the resulting white solid BYLC-03 was analyzed by GC-MS and the M/z of the product was 376(M +).
1H-NMR(300MHz,CDCl3):0.75-1.85(m,10H),1.95-2.75(m,8H),4.15-4.55(m,1H), 5.25-5.85(m,1H)，6.35-7.15(m,1H)。
Example 4
The structural formula of the liquid crystal compound is as follows:
the obtained white solid BYLC-04 was analyzed by GC-MS and the M/z of the product was 384(M +).
1H-NMR(300MHz,CDCl3):0.05-0.85(m,5H),1.95-2.95(m,6H),4.75-5.35(m,1H), 6.65-7.55(m,5H)。
Example 5
The structural formula of the liquid crystal compound is as follows:
the resulting white solid BYLC-05 was analyzed by GC-MS and the M/z of the product was 400(M +).
1H-NMR(300MHz,CDCl3):0.05-0.85(m,5H),1.95-2.95(m,4H), 3.65-4.15(m,2H),4.75-5.35(m,1H),6.65-7.55(m,5H)。
Example 6
The structural formula of the liquid crystal compound is as follows:
the obtained white solid BYLC-06 was analyzed by GC-MS and the M/z of the product was 356(M +).
1H-NMR(300MHz,CDCl3):0.75-1.85(m,5H),2.15-2.95(m,6H),4.65-5.15(m,1H), 6.85-7.35(m,5H)。
Example 7
The structural formula of the liquid crystal compound is as follows:
the obtained white solid BYLC-07 was analyzed by GC-MS and the M/z of the product was 466(M +).
1H-NMR(300MHz,CDCl3):0.75-1.95(m,20H),2.05-2.95(m,5H),4.65-5.15(m,1H) 7.15-7.65(m,5H)。
Example 8
The structural formula of the liquid crystal compound is as follows:
the resulting white solid BYLC-08 was analyzed by GC-MS and the M/z of the product was 382(M +).
1H-NMR(300MHz,CDCl3):1.55-1.95(m,8H),2.15-2.95(m,5H),4.75-5.25(m,1H), 7.15-7.65(m,5H)。
According to the technical scheme of the above embodiment, the liquid crystal compound mentioned in the summary of the invention can be synthesized only by simply replacing the corresponding raw materials without changing any substantial operation.
Comparative example 1
Comparative example 2
Experimental example 1
The data of the performance parameters of the liquid crystal compounds prepared in examples 1-5 and comparative example 1 (another similar liquid crystal compound known to be common) are compared and the results are shown in table 1:
TABLE 1
The experimental data show that the liquid crystal compound provided by the invention has larger vertical dielectric anisotropy and larger penetration rate, and the integral dielectric anisotropy is positive and is approximately 0, so that the driving voltage is effectively reduced, the response speed of a liquid crystal display device is improved, and the liquid crystal compound has the characteristics of moderate optical anisotropy value, high charge retention rate and the like.
Comparative example 3
Comparative example 4
Experimental example 2
The data of the performance parameters of the liquid crystal compounds prepared in examples 6 to 8 and comparative example 2 (another similar liquid crystal compound known to be common) are compared and the detection results are shown in table 2:
TABLE 2
The experimental data show that the liquid crystal compound provided by the invention has larger vertical dielectric anisotropy and larger penetration rate, and the integral dielectric anisotropy is positive and is approximately 0, so that the driving voltage is effectively reduced, the response speed of a liquid crystal display device is improved, and the liquid crystal compound has the characteristics of moderate optical anisotropy value, high charge retention rate and the like.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may 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 (11)
1. A liquid crystal compound characterized by one selected from the following structural formulae:
wherein:
R1denotes CF3Or OCF3；
R2Represents an alkyl or alkoxy group having 1 to 5 carbon atoms, a cyclopropyl group, a cyclobutyl group or a cyclopentyl group;
Z1represents a single bond;
Z2represents a single bond.
2. The liquid crystal compound of claim 1, wherein the compound is selected from one of the following structural formulas:
3. a process for the preparation of a compound according to claim 1 or 2, comprising:
Wherein, X represents I, Br or Cl;
R1denotes CF3Or OCF3；
R2Represents an alkyl or alkoxy group having 1 to 5 carbon atoms, a cyclopropyl group, a cyclobutyl group or a cyclopentyl group;
Z1represents a single bond;
Z2represents a single bond;
ring A and ring B are the same or different and each independently represents 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-phenylene;
m and n are the same or different and each independently represents 0, 1 or 2, and 0< m + n.ltoreq.3.
4. The production method according to claim 3,
and
the feeding molar ratio of (A) to (B) is 1.0: 1.0 to 1.5;
and/or the reaction temperature is between 60 and 140 ℃.
5. A liquid crystal composition comprising the liquid crystal compound according to claim 1 or 2.
6. The liquid crystal composition according to claim 5, wherein the liquid crystal compound is contained in the liquid crystal composition in an amount of 0.01 to 60% by mass.
7. The liquid crystal composition according to claim 6, wherein the liquid crystal compound is contained in the liquid crystal composition in an amount of 0.1 to 50% by mass.
8. The liquid crystal composition according to claim 7, wherein the liquid crystal compound is contained in the liquid crystal composition in an amount of 0.1 to 40% by mass.
9. Use of the liquid crystal compound according to claim 1 or 2 and the liquid crystal composition according to any one of claims 5 to 8 in the field of liquid crystal displays.
10. Use according to claim 9, in a liquid crystal display device.
11. Use according to claim 10, wherein the liquid crystal display device is a VA, TN, STN, FFS or IPS liquid crystal display.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910266906.0A CN111778040B (en) | 2019-04-03 | 2019-04-03 | Liquid crystal compound and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910266906.0A CN111778040B (en) | 2019-04-03 | 2019-04-03 | Liquid crystal compound and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111778040A CN111778040A (en) | 2020-10-16 |
| CN111778040B true CN111778040B (en) | 2022-03-22 |
Family
ID=72755418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910266906.0A Active CN111778040B (en) | 2019-04-03 | 2019-04-03 | Liquid crystal compound and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111778040B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113214083B (en) * | 2021-04-06 | 2022-04-22 | 北京八亿时空液晶科技股份有限公司 | Self-alignment polymerizable compound and application thereof |
| CN116003361A (en) * | 2022-12-30 | 2023-04-25 | 北京燕化集联光电技术有限公司 | Liquid crystal compound, composition and application |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006151864A (en) * | 2004-11-29 | 2006-06-15 | Dainippon Ink & Chem Inc | Difluorochroman derivative |
| TW200630465A (en) * | 2004-10-07 | 2006-09-01 | Merck Patent Gmbh | Chromane derivatives, process for the preparation thereof, and the use thereof |
| CN1829786A (en) * | 2003-06-30 | 2006-09-06 | 大日本油墨化学工业株式会社 | Chroman derivative and liquid-crystal composition containing the compound |
| CN101346366A (en) * | 2005-12-22 | 2009-01-14 | 默克专利股份有限公司 | Benzochromene derivatives |
| JP2016065149A (en) * | 2014-09-25 | 2016-04-28 | Jnc株式会社 | Liquid crystal composition and liquid crystal display element |
| WO2019048444A1 (en) * | 2017-09-08 | 2019-03-14 | Merck Patent Gmbh | Liquid-crystalline medium and liquid-crystal display comprising the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1491612B1 (en) * | 2003-06-23 | 2006-10-18 | Chisso Petrochemical Corporation | Chroman compound, liquid crystal composition including the compound and liquid crystal display element including the liquid crystal composition |
| WO2011055643A1 (en) * | 2009-11-09 | 2011-05-12 | Jnc株式会社 | Liquid crystal display element, liquid crystal composition, aligning agent, method for producing liquid crystal display element, and use of liquid crystal composition |
-
2019
- 2019-04-03 CN CN201910266906.0A patent/CN111778040B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1829786A (en) * | 2003-06-30 | 2006-09-06 | 大日本油墨化学工业株式会社 | Chroman derivative and liquid-crystal composition containing the compound |
| TW200630465A (en) * | 2004-10-07 | 2006-09-01 | Merck Patent Gmbh | Chromane derivatives, process for the preparation thereof, and the use thereof |
| JP2006151864A (en) * | 2004-11-29 | 2006-06-15 | Dainippon Ink & Chem Inc | Difluorochroman derivative |
| CN101346366A (en) * | 2005-12-22 | 2009-01-14 | 默克专利股份有限公司 | Benzochromene derivatives |
| JP2016065149A (en) * | 2014-09-25 | 2016-04-28 | Jnc株式会社 | Liquid crystal composition and liquid crystal display element |
| WO2019048444A1 (en) * | 2017-09-08 | 2019-03-14 | Merck Patent Gmbh | Liquid-crystalline medium and liquid-crystal display comprising the same |
Non-Patent Citations (2)
| Title |
|---|
| Discovery of EBI-1051: A novel and orally efficacious MEK inhibitor with benzofuran scaffold;Biao Lu et al;《Bioorganic & Medicinal Chemistry》;20171220;第26卷(第3期);第581-589页 * |
| 具有含氧亚甲基中心桥键的含氟液晶化合物的质谱裂解规律研究;张苹 等;《液晶与显示》;20170730;第32卷(第7期);第526-532页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111778040A (en) | 2020-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109206400B (en) | Liquid crystal compound containing dibenzothiophene structure and application thereof | |
| CN111592890B (en) | Liquid crystal compound and preparation method and application thereof | |
| CN111592517A (en) | Liquid crystal compound containing dibenzofuran structure and preparation method and application thereof | |
| CN109423297B (en) | Dibenzothiophene liquid crystal compound and preparation method and application thereof | |
| CN109423296B (en) | Dibenzothiophene negative dielectric anisotropy compound and preparation method and application thereof | |
| CN111778040B (en) | Liquid crystal compound and preparation method and application thereof | |
| CN114517097A (en) | Liquid crystal compound containing cyclohexene structure and preparation method and application thereof | |
| CN111825534A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN108728112A (en) | A kind of liquid-crystal compounds of negative dielectric anisotropic and the preparation method and application thereof | |
| CN109082281B (en) | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof | |
| CN111592889B (en) | Liquid crystal compound and preparation method and application thereof | |
| CN111484475B (en) | Liquid crystal compound and preparation method and application thereof | |
| CN113881443A (en) | Liquid crystal compound containing dibenzothiophene structure and application thereof | |
| CN106398717B (en) | A kind of epoxypentyl class liquid-crystal compounds and preparation method and application | |
| CN114105941B (en) | Novel liquid crystal compound and preparation method and application thereof | |
| CN113816883A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN114105966A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN111718725A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN109423298B (en) | Novel dibenzothiophene liquid crystal compound and preparation method and application thereof | |
| CN114686242A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN111718726B (en) | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof | |
| CN114573550A (en) | Liquid crystal compound and preparation method and application thereof | |
| CN111484853B (en) | Liquid crystal compound and preparation method and application thereof | |
| CN110616074A (en) | Novel liquid crystal compound and preparation and application thereof | |
| 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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |