CN104513129A - Intermediate for preparing liquid crystal compound containing terminal difluoroethylene group and preparation method of the intermediate - Google Patents
Intermediate for preparing liquid crystal compound containing terminal difluoroethylene group and preparation method of the intermediate Download PDFInfo
- Publication number
- CN104513129A CN104513129A CN201310462122.8A CN201310462122A CN104513129A CN 104513129 A CN104513129 A CN 104513129A CN 201310462122 A CN201310462122 A CN 201310462122A CN 104513129 A CN104513129 A CN 104513129A
- Authority
- CN
- China
- Prior art keywords
- compound
- formula
- organic solvent
- hour
- reaction
- 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.)
- Granted
Links
- RXZJWVPNFPPSEM-UHFFFAOYSA-N O=CCCc(cc1)ccc1Br Chemical compound O=CCCc(cc1)ccc1Br RXZJWVPNFPPSEM-UHFFFAOYSA-N 0.000 description 3
- 0 *c(cc1)ccc1Br Chemical compound *c(cc1)ccc1Br 0.000 description 1
- DNVWPCDGQBZHBM-UHFFFAOYSA-N CC(C=C(C1=C)F)=CC1F Chemical compound CC(C=C(C1=C)F)=CC1F DNVWPCDGQBZHBM-UHFFFAOYSA-N 0.000 description 1
- HBXFIXSFKULBOG-UHFFFAOYSA-N Cc1cc(F)c(C)c(F)c1 Chemical compound Cc1cc(F)c(C)c(F)c1 HBXFIXSFKULBOG-UHFFFAOYSA-N 0.000 description 1
- HRJHDOKEFMLOAW-UHFFFAOYSA-N FC(F)=CCCc(cc1)ccc1-c(cc1)ccc1Br Chemical compound FC(F)=CCCc(cc1)ccc1-c(cc1)ccc1Br HRJHDOKEFMLOAW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides an intermediate for preparing a liquid crystal compound containing terminal difluoroethylene groups and a preparation method of the intermediate. The intermediate has a structure represented as the formula I. The preparation method is simple in processes, is low in cost and is high in yield. The product is easy to purify and is suitable for being industrially produced.
Description
Technical field
The present invention relates to the preparation method for the preparation of the intermediate containing end position difluoroethylene group liquid crystal liquid crystal compound and this intermediate.
Background technology
In recent years, liquid crystalline cpd and liquid crystal material become one of focus of applied chemistry and materials chemistry research, electronics, optics, acoustics, biotechnology, chemical industry etc. respectively fermentation be widely used, and wherein extensive and the most final be its application in electronical display.Along with the development of information industry, to the requirement of liquid crystal material also in continuous raising.Although the report about liquid crystal material aspect is existing a lot, but they are not all suitable in indicating meter, because the liquid crystal material of display must meet the requirement such as wider operating temperature range, lower operating voltage, low viscosity, fast response, high stability.
CN102337139A discloses containing end position difluoroethylene liquid crystalline cpd, and this compounds has the characteristic that viscosity is low, dielectric is large, specific refractory power is high, in mixed liquid crystal formula, significantly can improve the performance of mixed liquid crystal.The method of preparation containing end position difluoroethylene liquid crystalline cpd is also reveal that in this patent.But these methods can not be entirely satisfactory, because in building-up process, Compound C
Yield lower, and technique is unstable, and cause final product to be difficult to purify like this, production cost raises, and is not suitable for industrialization, therefore needs to find new synthetic technology.
In order to solve problems of the prior art, the object of the invention is to provide a kind of preparation method for the preparation of the intermediate and this intermediate that contain end position difluoroethylene group liquid crystal liquid crystal compound newly, the method with to bromobenzyl chlorine for raw material, shorten reaction scheme, often walk reaction intermediate to be all easy to purify, and reaction temperature and, yield is high, is applicable to suitability for industrialized production.
Summary of the invention
One aspect of the present invention relates to the compound of a kind of formula I:
Wherein,
X represent Br or
represent
M represents 0 or 1.
In some embodiments, the compound of formula I is selected from any one in the compound of formula I-1 to formula I-4:
and
Wherein,
represent
In embodiments of the invention, the compound of preferred described formula I-3 is selected from one or more compounds in the group be made up of following compound:
and
and
The compound of described formula I-4 is selected from one or more compounds in the group be made up of following compound:
and
Another aspect of the present invention provides the method for the compound of a kind of preparation formula I-1, comprises the steps:
1), under alkaline condition, in organic solvent, 0.5-10 hour is reacted at 0-100 DEG C of temperature to bromobenzyl chlorine and acetaldehyde, obtains the compound of formula A
2) by the compound of formula A and difluorodibromomethane, triphenylphosphine and zinc powder, in organic solvent and under nitrogen protection condition, reaction 0.5-10 hour, obtains the compound of formula I-1
Another aspect of the present invention provides the method for the compound of a kind of preparation formula I-2, comprises the steps:
1), under alkaline condition, in organic solvent, 0.5-10 hour is reacted at 0-100 DEG C of temperature to bromobenzyl chlorine and acetaldehyde, obtains the compound of formula A
2) by the compound of formula A and difluorodibromomethane, triphenylphosphine and zinc powder, in organic solvent and under nitrogen protection condition, reaction 0.5-10 hour, obtains the compound of formula I-1
3) in the basic conditions, the compound of formula I-1 is at Pd (dppf) Cl
2catalysis under, with duplex boric acid pinacol ester in organic solvent and under nitrogen or argon, 20-150 DEG C of reaction 2-25 hour, obtain the compound of formula I-2
Another aspect of the present invention provides the method for the compound of a kind of preparation formula I-3, comprises the steps:
1), under alkaline condition, in organic solvent, 0.5-10 hour is reacted at 0-100 DEG C of temperature to bromobenzyl chlorine and acetaldehyde, obtains the compound of formula A
2) by the compound of formula A and difluorodibromomethane, triphenylphosphine and zinc powder, in organic solvent and under nitrogen protection condition, reaction 0.5-10 hour, obtains the compound of formula I-1
3) in the basic conditions, the compound of formula I-1 is at Pd (dppf) Cl
2catalysis under, with duplex boric acid pinacol ester in organic solvent and under nitrogen or argon, 20-150 DEG C of reaction 2-25 hour, obtain the compound of formula I-2
4) in the basic conditions, the compound of formula I-2 and the compound of formula B
Under the catalysis of four-triphenyl phosphorus palladium, in organic solvent and under nitrogen or argon shield condition, at 0-100 DEG C of temperature, reaction 0.5-30 hour, obtains the compound of formula I-3
Wherein,
represent
Y represents Br or I.
Another aspect of the present invention provides the method for the compound of a kind of preparation formula I-4, comprises the steps:
1), under alkaline condition, in organic solvent, 0.5-10 hour is reacted at 0-100 DEG C of temperature to bromobenzyl chlorine and acetaldehyde, obtains the compound of formula A
2) by the compound of formula A and difluorodibromomethane, triphenylphosphine and zinc powder, in organic solvent and under nitrogen protection condition, reaction 0.5-10 hour, obtains the compound of formula I-1
3) in the basic conditions, the compound of formula I-1 is at Pd (dppf) Cl
2catalysis under, with duplex boric acid pinacol ester in organic solvent and under nitrogen (or argon gas) is protected, 20-150 DEG C of reaction 2-25 hour, obtain the compound of formula I-2
4) in the basic conditions, the compound of formula I-2 and the compound of formula B
Under the catalysis of four-triphenyl phosphorus palladium, in organic solvent and under nitrogen or argon shield condition, at 0-100 DEG C of temperature, reaction 0.5-30 hour, obtains the compound of formula I-3
Wherein,
represent
Y represents Br or I;
5) in the basic conditions, the compound of formula I-3 is at Pd (dppf) Cl
2catalysis under, with duplex boric acid pinacol ester in organic solvent and under nitrogen or argon, 20-150 DEG C of reaction 2-25 hour, obtain the compound of formula I-4
Wherein,
represent
In some embodiments, organic solvent is selected from least one in methyl alcohol, ethanol, toluene, tetrahydrofuran (THF), glycol dimethyl ether, Isosorbide-5-Nitrae-dioxane, methyl-sulphoxide and N,N-dimethylacetamide.
In some embodiments, alkali is selected from least one in sodium hydroxide, potassium hydroxide, salt of wormwood, sodium carbonate, sodium bicarbonate, sodium acetate, choline (Choline) reagent, sodium hydride, potassiumphosphate, potassium primary phosphate and Potassium ethanoate.
Another aspect of the present invention also provides compound of the present invention to be application in the liquid crystalline cpd of vinylidene fluoride as intermediate at synthesis end group.
Compared with prior art, preparation method's tool of the present invention has the following advantages:
1. shorten reaction scheme, production cost is low;
2. ensureing that under the prerequisite that optical purity is good, yield is good;
3. reaction conditions is gentle, yield is high, and simple to operate, be suitable for suitability for industrialized production.
Accompanying drawing explanation
Fig. 1 is the MS figure of compd A;
Fig. 2 is the MS figure of Compound I-1;
Fig. 3 is the MS figure of Compound I-2;
Fig. 4 is the MS figure of Compound I-3-1;
Fig. 5 is the MS figure of Compound I-3-2;
Fig. 6 is the MS figure of Compound I-4-1;
Fig. 7 is the MS figure of Compound I-5;
Fig. 8 is the MS figure of Compound I-6;
Fig. 9 is the MS figure of Compound I-7; And
Figure 10 is the MS figure of Compound I-8.
Embodiment
Below with reference to specific embodiments, the present invention is described.It should be noted that, the following examples are example of the present invention, are only used for the present invention is described, and are not used for limiting the present invention.
In following examples, except the compound of being correlated with except compd A, general formula I and sub-general formula thereof and the liquid crystal monomer of synthesis thereof, all the other compound monomers used and related reagent all can be buied from market.The title of concrete reagent and No. CAS are listed in the following table:
Table 1: reagent name and No. CAS
Embodiment 1
1) synthesis of compd A
Take 2.632g choline reagent, 15mL H
2o, 2mL tetrahydrofuran (THF), 8.4mL toluene, in 100mL there-necked flask, are heated to 75 DEG C.25.08g is dissolved in 12mL tetrahydrofuran (THF) to bromobenzyl chlorine and 4.4g acetaldehyde, slowly in instillation reaction flask.React 5h under continuing this temperature, TLC display reaction terminates.
Reaction solution is chilled to room temperature, adds 50mL water, extraction into ethyl acetate three times, merges oil reservoir, anhydrous sodium sulfate drying, and concentrated dry solvent, column chromatography obtains 18.24g pale yellow transparent oily liquids compd A.MS m/z:212 (M
+), yield: 70%.
The MS figure of compd A is see Fig. 1.
2) synthesis of Compound I-1
Take 4.9g triphenylphosphine, measure 30mL DMF(dimethyl formamide), be placed in 100mL there-necked flask.Drip difluorodibromomethane (being dissolved in 10mL DMF) under nitrogen protection, drip off, stirring at room temperature 40min.Drip the DMF solution (2g is dissolved in 10mL DMF) of compd A, after dropwising, disposablely add 1.2g zinc powder.Heat up obviously, continue stirring reaction 2h, TLC display reacts completely.
Add 30mL water, extraction into ethyl acetate three times, merge organic layer, once, anhydrous sodium sulfate drying, concentrated dry solvent, column chromatography obtains 1g colourless transparent liquid Compound I-1 in washing.MS m/z:246 (M+), yield: 54%.
The MS figure of Compound I-1 is see Fig. 2.
Embodiment 2
The synthesis of Compound I-2
Take Compound I-1,10g duplex boric acid pinacol ester, 0.48g Pd (dppf) Cl that 8g is synthesized by embodiment 1
2, 3.2g Glacial acetic acid potassium, measure 100mL dimethyl sulfoxide (DMSO).Above-mentioned all materials join in 250mL single port bottle, nitrogen replacement three times, are warming up to 90 DEG C of reaction 20h, TLC displays and also have micro material.
Poured into by reaction solution in 50mL water, extraction into ethyl acetate three times, merge organic layer, be washed to neutrality, anhydrous sodium sulfate drying, concentrated dry solvent, slightly cross pillar, concentrated dry solvent, oil pump draws and dryly obtains 9g greenish transparent shape fluid cpds I-2.MS m/z:294 (M+), yield 90%.
The MS figure of Compound I-2 is see Fig. 3.
Embodiment 3
The synthesis of Compound I-3-1
Take the Compound I-2 of the 2-in-1 one-tenth of 3g embodiment, 2.89g to bromo-iodobenzene, 0.2g tetra--triphenyl phosphorus palladium, 2.8g salt of wormwood, measure 30mL toluene, 15mL ethanol, 15mL water.Above-mentioned all materials add in 250mL there-necked flask, nitrogen replacement three times, are heated to 80 DEG C of back flow reaction 14h, TLC displays and react completely.
Reaction solution is chilled to room temperature, adds 20mL water, extraction into ethyl acetate three times, merges organic layer, is washed to neutrality, anhydrous sodium sulfate drying, concentrated dry solvent, and thick pillar excessively, gained crude product ethyl acetate adds sherwood oil recrystallization and obtains 2.6g white solid I-3-1.MS m/z:322 (M
+), yield: 80%.
The MS figure of Compound I-3-1 is see Fig. 4.
Embodiment 4
1) synthesis of Compound I-3-2
Take the Compound I-2 of the 2-in-1 one-tenth of 3g embodiment, the fluoro-4-iodobenzene of the bromo-3-of 3.06g1-, 0.2g tetra--triphenyl phosphorus palladium, 2.8g salt of wormwood, measure 30mL toluene, 15mL ethanol, 15mL water.Above-mentioned all materials add in 250mL there-necked flask, nitrogen replacement three times, are heated to 80 DEG C of back flow reaction 14h, TLC displays and react completely.
Reaction solution is chilled to room temperature, adds 20mL water, extraction into ethyl acetate three times, merges organic layer, is washed to neutrality, anhydrous sodium sulfate drying, concentrated dry solvent, and thick pillar excessively, gained crude product ethyl acetate adds sherwood oil recrystallization and obtains 2.7g white solid I-3-2.MS m/z:340 (M
+), yield: 80%.
The MS figure of Compound I-3-2 is see Fig. 5.
2) synthesis of Compound I-4-1
Take 2g Compound I-3-2,1.5g duplex boric acid pinacol ester, 0.09g Pd (dppf) Cl
2, 1.1g Glacial acetic acid potassium, measure 20mL dimethyl sulfoxide (DMSO).Above-mentioned all materials join in 100mL single port bottle, nitrogen replacement three times, are warming up to 90 DEG C of reaction 20h, TLC displays and also have micro material.
Poured into by reaction solution in 20mL water, extraction into ethyl acetate three times, merge organic layer, be washed to neutrality, anhydrous sodium sulfate drying, concentrated dry solvent, slightly cross pillar, concentrated dry solvent, oil pump draws and dryly obtains 2g light green transparence fluid cpds I-4-2.MS m/z:388 (M+), yield: 90%.
The MS figure of Compound I-4-1 is see Fig. 6.
Embodiment 5
The synthesis of Compound I-5
Take Compound I-1,9.3g compd B, 0.9g tetra--triphenyl phosphorus palladium, the 11g salt of wormwood of 10g embodiment 1 synthesis, measure 60mL toluene, 30mL ethanol, 30mL water.Above-mentioned all materials add in 250mL there-necked flask, nitrogen replacement three times, are heated to 80 DEG C of back flow reaction 4h, TLC display reactions and terminate.
Reaction solution is chilled to room temperature, adds 50mL water, extraction into ethyl acetate three times, merges oil reservoir, anhydrous sodium sulfate drying, concentrated dry solvent, and thick pillar excessively, concentrated dry solvent, ethanol and re crystallization from toluene obtain 12g white crystalline Compound I-5.MS m/z:352 (M
+), yield: 85%.
The MS figure of Compound I-5 is see Fig. 7.
The liquid crystal property of Compound I-5:
Δn：0.2622；
Δε：129；
Cp：2.211。
Embodiment 6
The synthesis of Compound I-6
Take the Compound I-2 of the 2-in-1 one-tenth of 8.6g embodiment, 5g Compound C, 0.3g Pd (dppf) Cl
2, 5.7g Glacial acetic acid potassium, measure 50mL dimethyl sulfoxide (DMSO).Above-mentioned all materials add in 100mL there-necked flask, nitrogen replacement three times, are heated to 80 DEG C of reaction 7h, TLC display reactions and terminate.
Reaction solution is chilled to room temperature, adds 50mL water, extraction into ethyl acetate three times, merges oil reservoir, anhydrous sodium sulfate drying, concentrated dry solvent, and thick pillar excessively, concentrated dry solvent, ethanol and re crystallization from toluene obtain 6.5g white crystal.MS m/z:258 (M
+), yield: 85%.
The MS figure of Compound I-6 is see Fig. 8.
The liquid crystal property of Compound I-6:
Δn：0.1541；
Δε：1；
Cp：9.6。
Embodiment 7
1) synthesis of Compound I-7
Take Compound I-3-2,8g Compound D, 0.9g tetra--triphenyl phosphorus palladium, the 9.2g salt of wormwood of 11.3g embodiment 4 synthesis, measure 60mL toluene, 30mL ethanol, 30mL water.Above-mentioned all materials add in 250mL there-necked flask, nitrogen replacement three times, are heated to 80 DEG C of back flow reaction 4h, TLC display reactions and terminate.
Reaction solution is chilled to room temperature, adds 50mL water, extraction into ethyl acetate three times, merges oil reservoir, anhydrous sodium sulfate drying, concentrated dry solvent, and thick pillar excessively, concentrated dry solvent, ethanol and re crystallization from toluene obtain 10.3g white crystal.MS m/z:366 (M
+), yield: 85%.
The MS figure of Compound I-7 is see Fig. 9.
The liquid crystal property of Compound I-7:
Δn：0.2602；
Δε：123；
Cp：2.101。
Embodiment 8
1) synthesis of Compound I-8
Take Compound I-4-1,5g compd E, 0.7g Pd (dppf) Cl that 9.8g embodiment 4 is synthesized
2, 4.9g Glacial acetic acid potassium, measure 50mL dimethyl sulfoxide (DMSO).Above-mentioned all materials add in 100mL there-necked flask, nitrogen replacement three times, are heated to 80 DEG C of back flow reaction 7h, TLC display reactions and terminate.
Reaction solution is chilled to room temperature, adds 50mL water, extraction into ethyl acetate three times, merges oil reservoir, anhydrous sodium sulfate drying, concentrated dry solvent, and thick pillar excessively, concentrated dry solvent, ethanol and re crystallization from toluene obtain 8.2g white crystal.MS m/z:380 (M
+), yield: 85%.
The MS figure of Compound I-8 is see Figure 10.
The liquid crystal property of Compound I-8:
Δn：0.2622；
Δε：131；
Cp：2.061。
Claims (10)
1. the compound of a formula I:
Wherein,
X represent Br or
represent
M represents 0 or 1.
2. compound according to claim 1, is characterized in that, the compound of described formula I be selected from the compound of formula I-1 to formula I-4 any one:
and
Wherein,
represent
3. compound according to claim 2, is characterized in that, the compound of described formula I-3 is selected from one or more compounds in the group be made up of following compound:
and
and
The compound of described formula I-4 is selected from one or more compounds in the group be made up of following compound:
and
4. a method for the compound of preparation formula I-1, comprises the steps:
1), under alkaline condition, in organic solvent, 0.5-10 hour is reacted at 0-100 DEG C of temperature to bromobenzyl chlorine and acetaldehyde, obtains the compound of formula A
2) by the compound of formula A and difluorodibromomethane, triphenylphosphine and zinc powder, in organic solvent and under nitrogen protection condition, reaction 0.5-10 hour, obtains the compound of formula I-1
5. a method for the compound of preparation formula I-2, comprises the steps:
1), under alkaline condition, in organic solvent, 0.5-10 hour is reacted at 0-100 DEG C of temperature to bromobenzyl chlorine and acetaldehyde, obtains the compound of formula A
2) by the compound of formula A and difluorodibromomethane, triphenylphosphine and zinc powder, in organic solvent and under nitrogen protection condition, reaction 0.5-10 hour, obtains the compound of formula I-1
3) in the basic conditions, the compound of formula I-1 is at Pd (dppf) Cl
2catalysis under, with duplex boric acid pinacol ester in organic solvent and under nitrogen or argon, 20-150 DEG C of reaction 2-25 hour, obtain the compound of formula I-2
6. a method for the compound of preparation formula I-3, comprises the steps:
1), under alkaline condition, in organic solvent, 0.5-10 hour is reacted at 0-100 DEG C of temperature to bromobenzyl chlorine and acetaldehyde, obtains the compound of formula A
2) by the compound of formula A and difluorodibromomethane, triphenylphosphine and zinc powder, in organic solvent and under nitrogen protection condition, reaction 0.5-10 hour, obtains the compound of formula I-1
3) in the basic conditions, the compound of formula I-1 is at Pd (dppf) Cl
2catalysis under, with duplex boric acid pinacol ester in organic solvent and under nitrogen or argon, 20-150 DEG C of reaction 2-25 hour, obtain the compound of formula I-2
4) in the basic conditions, the compound of formula I-2 and the compound of formula B
Under the catalysis of four-triphenyl phosphorus palladium, in organic solvent and under nitrogen or argon shield condition, at 0-100 DEG C of temperature, reaction 0.5-30 hour, obtains the compound of formula I-3
Wherein,
represent
Y represents Br or I.
7. a method for the compound of preparation formula I-4, comprises the steps:
1), under alkaline condition, in organic solvent, 0.5-10 hour is reacted at 0-100 DEG C of temperature to bromobenzyl chlorine and acetaldehyde, obtains the compound of formula A
2) by the compound of formula A and difluorodibromomethane, triphenylphosphine and zinc powder, in organic solvent and under nitrogen protection condition, reaction 0.5-10 hour, obtains the compound of formula I-1
3) in the basic conditions, the compound of formula I-1 is at Pd (dppf) Cl
2catalysis under, with duplex boric acid pinacol ester in organic solvent and under nitrogen (or argon gas) is protected, 20-150 DEG C of reaction 2-25 hour, obtain the compound of formula I-2
4) in the basic conditions, the compound of formula I-2 and the compound of formula B
Under the catalysis of four-triphenyl phosphorus palladium, in organic solvent and under nitrogen or argon shield condition, at 0-100 DEG C of temperature, reaction 0.5-30 hour, obtains the compound of formula I-3
Wherein,
represent
Y represents Br or I;
5) in the basic conditions, the compound of formula I-3 is at Pd (dppf) Cl
2catalysis under, with duplex boric acid pinacol ester in organic solvent and under nitrogen or argon, 20-150 DEG C of reaction 2-25 hour, obtain the compound of formula I-4
Wherein,
represent
8. the method according to any one of claim 3-6, it is characterized in that, wherein said organic solvent is selected from least one in methyl alcohol, ethanol, toluene, tetrahydrofuran (THF), glycol dimethyl ether, Isosorbide-5-Nitrae-dioxane, methyl-sulphoxide and N,N-dimethylacetamide.
9. the method according to any one of claim 3-6, it is characterized in that, wherein said alkali is selected from least one in sodium hydroxide, potassium hydroxide, salt of wormwood, sodium carbonate, sodium bicarbonate, sodium acetate, choline reagent, sodium hydride, potassiumphosphate, potassium primary phosphate and Potassium ethanoate.
10. compound according to claim 1 and 2 is application in the liquid crystalline cpd of vinylidene fluoride as intermediate at synthesis end group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310462122.8A CN104513129B (en) | 2013-09-30 | 2013-09-30 | Preparation is containing the intermediate and the preparation method that hold position two vinyl fluoride group liquid crystalline cpd |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310462122.8A CN104513129B (en) | 2013-09-30 | 2013-09-30 | Preparation is containing the intermediate and the preparation method that hold position two vinyl fluoride group liquid crystalline cpd |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104513129A true CN104513129A (en) | 2015-04-15 |
| CN104513129B CN104513129B (en) | 2016-06-08 |
Family
ID=52789038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310462122.8A Active CN104513129B (en) | 2013-09-30 | 2013-09-30 | Preparation is containing the intermediate and the preparation method that hold position two vinyl fluoride group liquid crystalline cpd |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104513129B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1170352A2 (en) * | 2000-07-07 | 2002-01-09 | Chisso Corporation | Diflourovinyl compound, liquid crystal composition and liquid crystal display |
| US20070228329A1 (en) * | 2006-03-30 | 2007-10-04 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
| CN102337139A (en) * | 2011-08-02 | 2012-02-01 | 江苏和成化学材料有限公司 | Liquid crystal composition and liquid crystal display comprising same |
| CN103205265A (en) * | 2013-03-14 | 2013-07-17 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
-
2013
- 2013-09-30 CN CN201310462122.8A patent/CN104513129B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1170352A2 (en) * | 2000-07-07 | 2002-01-09 | Chisso Corporation | Diflourovinyl compound, liquid crystal composition and liquid crystal display |
| US20070228329A1 (en) * | 2006-03-30 | 2007-10-04 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
| CN102337139A (en) * | 2011-08-02 | 2012-02-01 | 江苏和成化学材料有限公司 | Liquid crystal composition and liquid crystal display comprising same |
| CN103205265A (en) * | 2013-03-14 | 2013-07-17 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104513129B (en) | 2016-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103254903B (en) | Liquid crystalline cpd containing difluoro methylene key bridge and preparation method thereof and composition | |
| KR20170121152A (en) | Liquid crystal compound containing difluoromethoxy bridging, composite, and application thereof | |
| CN103194242A (en) | Liquid crystal compound containing deuterium and preparation method as well as application thereof | |
| CN109423297B (en) | Dibenzothiophene liquid crystal compound and preparation method and application thereof | |
| CN103641742B (en) | A kind of novel liquid crystal luminescent material and preparation method thereof | |
| CN103773386B (en) | Liquid crystal compound containing 1,4-dioxane and pentafluoro-allyloxy structure and liquid crystal composition thereof | |
| CN104513145A (en) | 2,3,5-Trifluoro-4-difluoro(3,4,5-trifluorophenylol)methyl-benzaldehyde, its synthetic method and its application in preparation of liquid crystal compound | |
| CN101768447B (en) | Polyfluoric terphenyl liquid crystal compound and synthesis method and use thereof | |
| CN101119954A (en) | Trifluoronaphthalene derivative and liquid crystal composition comprising the same compound | |
| IT201800000667A1 (en) | PROCEDURE FOR THE PREPARATION OF DISPLACED DIARYLOXYHETERODIAZOLIC COMPOUNDS | |
| CN103756688B (en) | Pentafluoropropylene ether liquid crystal compound as well as preparation method and application thereof | |
| CN101580716A (en) | Terminal isothiocyano liquid-crystal compound containing pyrimidine ring and preparation method thereof | |
| CN103773384B (en) | Liquid crystal compound containing cyclopentyl and pentafluoro-allyloxy and liquid crystal composition thereof | |
| CN104513129B (en) | Preparation is containing the intermediate and the preparation method that hold position two vinyl fluoride group liquid crystalline cpd | |
| CN104513140B (en) | Contain the liquid crystalline cpd and preparation method and application of holding position difluoroethylene group | |
| CN104046366A (en) | Liquid crystal compound containing 2-oxo-bicyclo[2, 2, 1] heptane structure, preparation method and application thereof | |
| CN103553872B (en) | A kind of containing bicyclic group [2,2,1] iieptanes compound and application | |
| CN109423298B (en) | Novel dibenzothiophene liquid crystal compound and preparation method and application thereof | |
| CN106905133B (en) | Spiro-fluorene-indene diketone compound and preparation method and application thereof | |
| CN104046367B (en) | A kind of liquid crystalline cpd containing 2,6-dioxygen generation-bicyclic group-[2.2.1] heptane structure and its preparation method and application | |
| CN104387245B (en) | Liquid crystal compound, preparation method and applications thereof | |
| CN103614145B (en) | Tetrahydrofuran structure containing liquid crystal compound and preparation method and applications thereof | |
| CN103664539B (en) | Spiral shell [3,5] nonane derivatives and preparation method thereof and application | |
| JP5708994B2 (en) | Compound having fluorinated oxabicyclononane structure and liquid crystal composition thereof | |
| CN104370864B (en) | A kind of 2-(6-hydroxyl-2,3-Dihydrobenzofuranes-3-base) cyanide compound and prepare the method for TAK-875 medicine with this compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |