CN102888225A - Conjugated separate liquid crystal compound, and preparation method and application thereof - Google Patents
Conjugated separate liquid crystal compound, and preparation method and application thereof Download PDFInfo
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- CN102888225A CN102888225A CN 201210388466 CN201210388466A CN102888225A CN 102888225 A CN102888225 A CN 102888225A CN 201210388466 CN201210388466 CN 201210388466 CN 201210388466 A CN201210388466 A CN 201210388466A CN 102888225 A CN102888225 A CN 102888225A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- -1 p-toluenesulfonyloxy group Chemical group 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 8
- 230000008859 change Effects 0.000 abstract description 2
- 238000013461 design Methods 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 0 *c(ccc(OCC(CC1)CCC1c(cc1)ccc1I)c1[I-]=*)c1I Chemical compound *c(ccc(OCC(CC1)CCC1c(cc1)ccc1I)c1[I-]=*)c1I 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- PKIYFPSPIFCDDB-UHFFFAOYSA-N 4-ethoxy-2,3-difluorophenol Chemical compound CCOC1=CC=C(O)C(F)=C1F PKIYFPSPIFCDDB-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NDYYFARMJFBLRK-UHFFFAOYSA-N [4-(4-propylphenyl)cyclohexyl]methanol Chemical compound C1=CC(CCC)=CC=C1C1CCC(CO)CC1 NDYYFARMJFBLRK-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
The invention provides a conjugated separate liquid crystal compound disclosed as a general formula I, and a preparation method and application thereof. In the general formula I, m is a whole number ranging from 1 to 4. Independent conjugated structures are respectively used at the two ends of the molecule to change the design of the past single conjugated system of liquid crystal molecules. Compared with other liquid crystal compounds in the prior art, the liquid crystal compound provided by the invention has large optical anisotropy and clear bright spots. In the liquid crystal compound preparation process, the raw materials are accessible, the synthetic route is simple and easy to implement, and thus, the preparation method is suitable for large-scale industrial production.
Description
Technical Field
The invention relates to the field of liquid crystal materials, and provides a conjugated separation type liquid crystal compound and a preparation method and application thereof.
Background
Liquid crystal display elements are used in various household electric appliances such as watches and calculators, measuring instruments, automobile panels, word processors, computers, printers, televisions, and the like. Typical examples of the night-view display mode include PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), CSH (color super homeotropic), and the like. The driving method of the element is classified into a PM (passive matrix) type and an AM (active matrix) type. PM is classified into static (static) and multiplex (multiplex) types. AM is classified into a TFT (thin film transistor), an MIM (metal insulator metal), and the like. The types of TFTs are amorphous silicon (amorphous silicon) and polycrystalline silicon (polysilicon). The latter is classified into a high temperature type and a low temperature type according to a manufacturing process. Liquid crystal display elements are classified into a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both light sources of natural light and backlight, depending on the type of light source.
Among these display systems, IPS type, ECB type, VA type, CSH type, and the like are different from TN type or STN type which are commonly used at present in that liquid crystal materials having negative dielectric anisotropy are used for the former. Among these display systems, VA display by AM driving is particularly applied to display elements requiring high speed and wide viewing angle, and among them, liquid crystal elements such as televisions are most expected.
Liquid crystal materials used in VA-type and other display modes are required to have a low driving voltage, a high response speed, a wide operating temperature range, a large absolute value of negative dielectric anisotropy, a high phase transition temperature, and a low viscosity. Among them, in order to realize high-speed response, it is necessary to reduce the cell gap of the display element. However, in order to set the retardation (retadation) expressed by the product (Δ n × d) of the refractive index anisotropy (Δ n) and the cell interval (d) to the optimum, it is necessary to adjust the refractive index anisotropy and the cell interval of the liquid crystal material to the optimum ranges. Therefore, a boundary exists in a narrow cell interval. In order to increase the response speed without changing the cell gap, it is effective to use a liquid crystal composition having a low viscosity. In liquid crystal display devices such as televisions, a high response speed is required, and therefore development of a liquid crystal composition having a particularly low viscosity is required.
Conventionally, as a liquid crystal material having negative dielectric anisotropy, a liquid crystal compound having the following structure is disclosed in patent document US 4637897.
In the formula, R1、R2Represents an alkyl group of 1 to 12 carbon atoms, X, Y is F, Z is-C2H4-、-OCH2-、-COO-、-OCO-。
Patent document CN101128566A discloses a composition containing a compound having the following structure
In the formula, R1Represents an alkenyl group of 2 to 10 carbon atoms, R2Represents an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 10 carbon atoms, and m is 0, 1 or 2.
The liquid crystal composition having a negative dielectric anisotropy cannot achieve a sufficiently low viscosity and a sufficiently high isotropic transition point (clearing point) in a liquid crystal composition requiring a high response speed such as a liquid crystal television, and cannot satisfy the demand for a liquid crystal material for the development of a liquid crystal display element.
Disclosure of Invention
The invention provides a conjugate separation type liquid crystal compound and a preparation method and application thereof.
In one aspect of the present invention, there is provided a conjugated separation type liquid crystal compound having a structure represented by general formula (i):
wherein,
R1and R2The same or different, each independently selected from the group consisting of H, halogen, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 15 carbon atoms and a halogenated or unsubstituted alkenyl or alkenyloxy group having 2 to 15 carbon atoms, wherein, in said R1And R2One or more-CH of2-the groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atoms are not directly attached to each other;
L1、L2identical or different, each independently selected from the group consisting of F, Cl, CN, CF3And OCF3A group of (a);
m is 1, 2,3 or 4.
In some embodiments, R1And R2Each independently selected from the group consisting of H, F, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 10 carbon atoms, and a halogenated or unsubstituted alkenyl or alkenyloxy group having 2 to 10 carbon atoms, wherein in said R1And R2One or more-CH of2The-groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-with the proviso that oxygen atoms are not directly attached to each other.
In some embodiments, R2Selected from the group consisting of halogenated or unsubstituted alkoxy groups having 1 to 10 carbon atoms and halogenated or unsubstituted alkenyloxy groups having 2 to 10 carbon atoms.
In some embodiments, L is1、L2Each independently selected from F,Cl and CN.
In some embodiments, m is 1 or 2.
Preferably, the compounds of the invention are selected from the group consisting of:
more preferably, the compounds of the present invention are selected from the group consisting of:
wherein R is1Selected from the group consisting of halogenated or unsubstituted alkyl or alkoxy groups having 1 to 7 carbon atoms and halogenated or unsubstituted alkenyl or alkenyloxy groups having 2 to 7 carbon atoms.
Another aspect of the invention provides a method of preparing a compound of the invention, comprising the steps of:
step 1) carrying out a substitution reaction on a compound of a general formula Ia to obtain a compound of a general formula IIa, wherein an MG group is selected from the group consisting of an iodine atom, a bromine atom, a p-toluenesulfonyloxy group and a methylsulfonyloxy group;
step 2) reacting the compound of the general formula IIIa with alkali, and then reacting with the compound of the general formula IIa obtained in the step 1) to obtain the compound of the general formula I;
in the step 1), the MG group is an iodine atom or a p-methyl benzenesulfonyloxy group; in the step 2), the base is at least one selected from the group consisting of sodium hydroxide, potassium carbonate, and sodium carbonate.
The reaction flow of the preparation method is as follows:
formula IIIa (I)
In a further aspect of the invention there is provided a liquid crystal composition comprising one or more compounds of formula (I).
It is still another aspect of the present invention to provide a liquid crystal display element comprising the liquid crystal composition as a constituent element.
The invention changes the design of the single conjugated system of the prior liquid crystal molecules by respectively using independent conjugated structures at two ends of the molecules, and compared with other liquid crystal compounds in the prior art, the provided liquid crystal compound with the general formula (I) has large optical anisotropy and clearing point; in the preparation process of the liquid crystal compound with the general formula (I), the raw materials are easy to obtain, the synthetic route is simple and feasible, and the method is suitable for large-scale industrial production.
The abbreviated codes of the test items in the following examples are as follows:
tni: clearing points (nematic-isotropic phase transition temperature)
Eta: bulk viscosity (mPa.s, 20 ℃ C., unless otherwise stated)
Δ n: optical anisotropy (589 nm, 20 ℃ C.)
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
The liquid-crystalline compounds of the formula I prepared in the examples below were tested for optical anisotropy and clearing point and for extrapolation parameters as follows:
a commercial liquid crystal with the serial number of TS023-102, produced by Jiangsu Hecheng display science and technology Limited, is selected as a matrix, a liquid crystal compound shown as a general formula (I) is dissolved in the matrix according to the weight proportion of 10 percent, the optical anisotropy, clearing point and bulk viscosity eta (20 ℃) of the mixture are tested, and the optical anisotropy delta n (20 ℃, 589 nm) and clearing point Tni of the liquid crystal compound shown as the general formula (I) are externally deduced according to the addition proportion of the matrix and a linear relation.
EXAMPLE 1 Compound I-1-2-1 (R)1=C3H7,R2=C2H5) Preparation of
Step 1:
a1000 ml three-necked flask was charged with 27.2g of (4- (4-propylphenyl) cyclohexyl) methanol, 23.7g of triethylamine and 400ml of dichloromethane. After cooling to 0 ℃ a solution of 26.7g of p-toluenesulfonyl chloride in 150ml of dichloromethane was added and the reaction was continued at room temperature for 3 h. The reaction solution was poured into water, extracted with dichloromethane, and the organic layer was washed with water to neutrality, dried over anhydrous sodium sulfate, and then the solvent was removed by rotary evaporation, followed by recrystallization from ethanol to obtain 29g of (4- (4-propylphenyl) cyclohexyl) methyl 4-methylbenzenesulfonate.
Step 2:
a500 ml three-necked flask was charged with 4-ethoxy-2, 3-difluorophenol 8.4g and N, N-dimethylformamide 60ml, cooled to 0 ℃ and added with 1.4g of sodium hydroxide in portions, raised to 60 ℃ and added dropwise with a solution of 15.6g of (4- (4-propylphenyl) cyclohexyl) methyl 4-methylbenzenesulfonate in N, N-dimethylformamide 90ml, and then reacted at that temperature for 3 hours. Pouring the reaction solution into ice water, extracting with ethyl acetate, washing with water, drying and spin-drying to obtain the product. Performing column chromatography with n-hexane, and recrystallizing with n-hexane to obtain 5g of target compound I-1-2-1 (R)1=C3H7,R2=C2H5)。MS m/z：388(M+)。
Testing the synthesized liquid Crystal Compound I-1-2-1 (R)1=C3H7,R2=C2H5) The resulting mixture bulk viscosity η =52.1, extrapolated parameters: Δ n =0.140, η =52.1mpa.s, Tni =171.2 ° c
EXAMPLE 2 Compound I-5-2-1 (R)1=C3H7,R2=C2H5) Preparation of
Step 1:
a1000 ml three-necked flask was charged with 8g of (4'- (4-propylphenyl) - [1,1' -bicyclohexyl ] -4-yl) methanol, 7.1g of triethylamine and 200ml of dichloromethane. After cooling to 0 ℃ a solution of 5.7g of p-toluenesulfonyl chloride in 50ml of dichloromethane was added and the reaction was continued at room temperature for 3 h. The reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with water to neutrality, dried over anhydrous sodium sulfate, and then the solvent was removed by rotary evaporation, followed by recrystallization from ethanol to give 10g of (4'- (4-propylphenyl) - [1,1' -bicyclohexyl ] -4-yl) methyl 4-methylbenzenesulfonate.
Step 2:
adding 4.5g of 4-ethoxy-2, 3-difluorophenol and 60ml of N, N-dimethylformamide into a 500ml three-necked flask, cooling to 0 ℃, adding 1.4g of sodium hydroxide in portions, raising the temperature to 60 ℃, and dropwise adding 10g of (4'- (4-propylphenyl) - [1,1' -dicyclohexyl) into the mixture]-4-yl) methyl 4-methylbenzenesulfonate in 90ml of N, N-dimethylformamide and then reacted at this temperature for 3 h. Pouring the reaction solution into ice water, extracting with ethyl acetate, washing with water, drying and spin-drying to obtain the product. Performing column chromatography with n-hexane, and recrystallizing with n-hexane to obtain 5.1g of target compound I-5-2-1 (R)1=C3H7,R2=C2H5)。MS m/z：470(M+)。
The synthesized liquid-crystalline compound I-5-2-1 (R) was tested1=C3H7,R2=C2H5) The resulting mixture bulk viscosity η =55.1, extrapolated parameters: Δ n =0.151, η =55.1mpa.s, Tni =214 ° c
Comparative example 1
The compounds of the following structures were synthesized and tested as described in the Liquid Crystals (1989),5(1), 159-70.
A comparison of several of the above compounds is made and the results are shown in the following table.
TABLE 1
| Compound (I) | η（mPa.s） | Δn | Tni（℃） |
| I-1-2-1(R1=C3H7,R2=C2H5) | 52.1 | 0.140 | 172 |
| I-5-2-1(R1=C3H7,R2=C2H5) | 55.1 | 0.151 | 214 |
| C-1 | 52.5 | 0.095 | 127 |
| C-2 | 51.4 | 0.107 | 160 |
As can be seen from the above table, the liquid crystal compound shown in the general formula i has a larger optical anisotropy Δ n and a higher clearing point Tni under the condition of the same viscosity η, which brings great convenience to the preparation of the liquid crystal composition, and the liquid crystal composition can have the characteristics of low viscosity, large optical anisotropy and high clearing point at the same time, thereby expanding the performance of the liquid crystal display element.
Claims (11)
1. A compound of the general formula I:
wherein,
R1and R2The same or different, each independently selected from H, halogen, halogenated or unsubstituted alkyl or alkoxy having 1 to 15 carbon atoms and halogenated or unsubstituted alkenyl or alkenyloxy having 2 to 15 carbon atomsWherein in said R1And R2One or more-CH of2-the groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-, with the proviso that the oxygen atoms are not directly attached to each other;
L1、L2identical or different, each independently selected from the group consisting of F, Cl, CN, CF3And OCF3A group of (a);
m is 1, 2,3 or 4.
2. A compound of claim 1, wherein R is1And R2Each independently selected from the group consisting of H, F, a halogenated or unsubstituted alkyl or alkoxy group having 1 to 10 carbon atoms, and a halogenated or unsubstituted alkenyl or alkenyloxy group having 2 to 10 carbon atoms, wherein in said R1And R2One or more-CH of2The-groups may each be independently replaced by-CH = CH-, -O-, -CH = CF-, -CF = CH-, -CF = CF-, -CO-O-or-O-CO-with the proviso that oxygen atoms are not directly attached to each other.
3. A compound of claim 2, wherein R is2Selected from the group consisting of halogenated or unsubstituted alkoxy groups having 1 to 10 carbon atoms and halogenated or unsubstituted alkenyloxy groups having 2 to 10 carbon atoms.
4. The compound of claim 1, wherein L is1、L2Each independently selected from the group consisting of F, Cl and CN.
5. The compound of claim 1, wherein m is 1 or 2.
6. The compound according to any one of claims 1-5, wherein the compound is selected from the group consisting of:
7. the compound of claim 6, wherein the compound is selected from the group consisting of:
wherein,
R1selected from the group consisting of halogenated or unsubstituted alkyl or alkoxy groups having 1 to 7 carbon atoms and halogenated or unsubstituted alkenyl or alkenyloxy groups having 2 to 7 carbon atoms.
8. A process for the preparation of a compound as claimed in any one of claims 1 to 7, comprising the steps of:
step 1) carrying out a substitution reaction on a compound of a general formula Ia to obtain a compound of a general formula IIa, wherein an MG group is selected from the group consisting of an iodine atom, a bromine atom, a p-toluenesulfonyloxy group and a methylsulfonyloxy group;
step 2) reacting the compound of the general formula IIIa with alkali, and then reacting with the compound of the general formula IIa obtained in the step 1) to obtain the compound of the general formula I;
9. the method of claim 8, wherein:
in the step 1), the MG group is an iodine atom or a p-methyl benzenesulfonyloxy group;
in the step 2), the base is at least one selected from the group consisting of sodium hydroxide, potassium carbonate, and sodium carbonate.
10. A liquid crystal composition comprising the liquid crystal compound according to any one of claims 1 to 7.
11. A liquid crystal display element comprising the liquid crystal composition according to claim 10.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103880595A (en) * | 2014-04-10 | 2014-06-25 | 石家庄科润显示材料有限公司 | Flexible liquid crystal intermediate trans p-alkyl dicyclohexyl methanol benzene and preparation method thereof |
| CN110804005A (en) * | 2018-08-04 | 2020-02-18 | 石家庄诚志永华显示材料有限公司 | Compound, liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN115894181A (en) * | 2022-09-30 | 2023-04-04 | 渭南高新区海泰新型电子材料有限责任公司 | Synthetic method of cyclohexenyl cyclohexyl difluorobenzene liquid crystal compound |
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2012
- 2012-10-13 CN CN 201210388466 patent/CN102888225A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880595A (en) * | 2014-04-10 | 2014-06-25 | 石家庄科润显示材料有限公司 | Flexible liquid crystal intermediate trans p-alkyl dicyclohexyl methanol benzene and preparation method thereof |
| CN103880595B (en) * | 2014-04-10 | 2016-01-06 | 石家庄科润显示材料有限公司 | A kind of flexible liquid crystal intermediate trans is to alkylbenzene dicyclohexyl methyl alcohol and preparation method thereof |
| CN110804005A (en) * | 2018-08-04 | 2020-02-18 | 石家庄诚志永华显示材料有限公司 | Compound, liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN115894181A (en) * | 2022-09-30 | 2023-04-04 | 渭南高新区海泰新型电子材料有限责任公司 | Synthetic method of cyclohexenyl cyclohexyl difluorobenzene liquid crystal compound |
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Application publication date: 20130123 |