CN102838584A - Liquid crystal monomer bicyclohexyl-containing epoxyethane compound and synthetic method thereof - Google Patents
Liquid crystal monomer bicyclohexyl-containing epoxyethane compound and synthetic method thereof Download PDFInfo
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- CN102838584A CN102838584A CN2012103370529A CN201210337052A CN102838584A CN 102838584 A CN102838584 A CN 102838584A CN 2012103370529 A CN2012103370529 A CN 2012103370529A CN 201210337052 A CN201210337052 A CN 201210337052A CN 102838584 A CN102838584 A CN 102838584A
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Abstract
The invention discloses a liquid crystal monomer bicyclohexyl-containing epoxyethane compound and a synthetic method thereof. The liquid crystal monomer bicyclohexyl-containing epoxyethane compound has such structure, wherein R is one of fluorine, chlorine, H, C1-C5 linear chain alkyl and C1-C5 linear chain alkoxy; R' is one of fluorine, chlorine, H, C1-C5 linear chain alkyl, C1-C5 linear chain alkoxy, and cyan; and such compound can be independently or mixed to be used for liquid crystal display in various forms. The liquid crystal monomer bicyclohexyl-containing epoxyethane compound and the synthetic method provided by the invention have the characteristics that the liquid crystal display is achieved, the demands on 3D (three-dimensional) display technology are met, the rotating viscosity of a liquid crystal material is reduced, and the dielectric anisotropy coefficient of the liquid crystal material is improved.
Description
Technical field
The present invention relates to the fine chemical technology field, especially relate to a kind of liquid crystal monomer and contain two hexanaphthene oxane compounds and compound method thereof, this kind contains two hexanaphthene oxane compounds can be used for liquid-crystal display.
Background technology
Lcd technology has been widely used in the daily life; The synthetic of its core material-liquid crystal monomer is the emphasis that the chemist pays close attention to always; Along with the renewal of lcd technology, the 3D technique of display is more and more paid close attention to by people at present, the mainstream technology type that 3D shows; Comprised spectacle 3D technology and bore hole formula 3D technology, wherein spectacle 3D technology comprises aberration formula 3D technology, polarization type 3D technology and initiatively fast gate-type 3D technology; Bore hole formula 3D technology comprises disparity barrier formula 3D technology, lens pillar formula 3D technology, points to light-source type 3D technology etc.Above-mentioned various types of 3D technique of display is because there is different difference in the principle of its demonstration with mode; What the enough liquid crystal panels of ability were realized the 3D demonstration at present mainly is polarization type, initiatively fast gate-type, disparity barrier formula, lens pillar formula and sensing light-source type; For panel producer; What no matter preparation was used is any 3D display mode, reduces the time of response of liquid crystal and make liquid crystal panel have faster that refreshing frequency also is the important goal that producer is constantly pursued.And the dielectric anisotropy coefficient of the rotation viscosity of minimizing liquid crystal material, increase liquid crystal material is the key that reduces the liquid crystal response time.But this structural performance with liquid crystal material own is relevant; Any single liquid crystal material all can not independently satisfy at present; Can only be mixed to satisfy through monomer and show needs; Therefore the liquid crystal material of the low rotation of exploitation viscosity, high dielectric anisotropy coefficient is the field that the monomer developer constantly explores, and the compound new in this field also constantly is developed.
Summary of the invention
The objective of the invention is to improve the performance of existing bis cyclohexane liquid crystal; In the liquid crystal molecule skeleton, introduce oxane structure; The low characteristics of bis cyclohexane liquid crystal viscosity both can have been kept; The characteristics that can send out again and wave that oxane class liquid crystal phase transition temperature is wide, pitch are long, so a kind of needs that are used for liquid-crystal display, satisfy the 3D technique of display be provided, reduce the rotation viscosity of liquid crystal material, the liquid crystal monomer that improves the dielectric anisotropy coefficient of liquid crystal material contains two hexanaphthene oxane compounds and compound method thereof.
The objective of the invention is to realize like this, a kind of liquid crystal monomer contains two hexanaphthene oxane compounds, is characterized in that this compound structure is following:
R is one of the straight chained alkyl of fluorine, chlorine, H, C1-C5, straight chain alkoxyl group of C1-C5 in the formula; R ' is one of straight chain alkoxyl group, cyanic acid of straight chained alkyl, the C1-C5 of fluorine, chlorine, H, C1-C5, and this compounds can be separately or is mixed for the liquid-crystal display of various display formats.
In order to realize the object of the invention, it is to adopt following synthetic route that above-mentioned liquid crystal monomer contains two hexanaphthene oxane compounds:
Ⅰ Ⅱ Ⅲ
Is raw material to alkyl dicyclohexyl formaldehyde and the 2-of structure shown in II to the alkyl phenyl Ucar 35 with structure shown in I, and wherein R, R ' and the R, the R ' that contain in two hexanaphthene oxane compounds III are identical in chemical compounds I, the II, adopt tosic acid to make catalyzer; With the organic solvent is reaction medium, at temperature 35-200 ℃, and reaction 2-12h; Contained two hexanaphthene oxane compounds III accordingly, after having reacted, through washing; Extraction; Recrystallization, its purified ω III>99%, overall yield of reaction is greater than 70%.
In order further to realize the object of the invention, the quality that can be to use the catalyzer tosic acid is the 1%-20% of the quality of starting compound I.
In order further to realize the object of the invention, can be that described organic solvent is a kind of in toluene, YLENE, normal heptane, the normal hexane.
In order further to realize the object of the invention, can be that temperature of reaction is 60-110 ℃, reaction times 3-8h.
The present invention has selected bis cyclohexane with oxane as the main body framework of compound, can reduce liquid crystal molecule viscosity when the design compound structure; Reduce threshold voltage; Improve transformation temperature, purpose makes it can be used as liquid crystal monomer and uses, and the synthetic route of this compounds is simple.
Embodiment
Below in conjunction with embodiment the present invention is done further explain.
Embodiment 1, and a kind of liquid crystal monomer contains two hexanaphthene oxane compounds, it is characterized in that this compound structure is following:
R is one of the straight chained alkyl of fluorine, chlorine, H, C1-C5, straight chain alkoxyl group of C1-C5 in the formula; R ' is one of straight chain alkoxyl group, cyanic acid of straight chained alkyl, the C1-C5 of fluorine, chlorine, H, C1-C5; This compounds can be separately or is mixed for the liquid-crystal display of various display formats, is to adopt following synthetic route:
Ⅰ Ⅱ Ⅲ
Is raw material to alkyl dicyclohexyl formaldehyde and the 2-of structure shown in II to the alkyl phenyl Ucar 35 with structure shown in I, and wherein R, R ' and the R, the R ' that contain in two hexanaphthene oxane compounds III are identical in chemical compounds I, the II, adopt tosic acid to make catalyzer; With the organic solvent is reaction medium, at temperature 35-200 ℃, and reaction 2-12h; Contained two hexanaphthene oxane compounds III accordingly, after having reacted, through washing; Extraction, recrystallization, its purified ω III>99%; Overall yield of reaction is greater than 70%, and using the quality of catalyzer tosic acid is the 1%-20% of the quality of starting compound I, and organic solvent is a kind of in toluene, YLENE, normal heptane, the normal hexane; Optimal reaction temperature is 60-110 ℃, reaction times 3-8h;
Present embodiment contain two hexanaphthene oxane compounds be 5-to ethylphenyl-2-(to propyl group bis cyclohexane base)-1, the 3-diox, a representes with III;
In three mouthfuls of reaction flasks of the 250mL that mechanical stirring, reflux condensing tube, feed hopper are housed, add successively n-propyl dicyclohexyl formaldehyde 24g, 2-is to ethylphenyl Ucar 35 20g, catalyzer tosic acid 3g, toluene 110mL; The beginning stirring heating, 108-110 ℃ of back flow reaction 3-8h, sampling analysis, the result confirms reaction terminating according to gas phase analysis; Cooling adds entry 50mL then in reaction solution, separatory, and water extracts with toluene 20mL; Merge organic phase, washing, is filtered with the dry 8h of anhydrous magnesium sulfate 5g to neutral; Use toluene 10mL drip washing filter cake twice again, sampling analysis is confirmed thick product quality ω III a:76%, after distillation desolventizes, and purifying; Get product III a28.6g, ω III a:99.5%, yield: 70%, product mass spectrum result: ES-MS m/z:398 [M]+.
Embodiment 2, and a kind of liquid crystal monomer contains two hexanaphthene oxane compounds and compound method thereof, present embodiment contain two hexanaphthene oxane compounds be 5-to ethylphenyl-2-(to propyl group bis cyclohexane base)-1, the 3-diox, b representes with III;
In three mouthfuls of reaction flasks of the 250mL that mechanical stirring, reflux condensing tube, feed hopper are housed, add successively n-pentyl dicyclohexyl formaldehyde 29g, 2-is to ethylphenyl Ucar 35 22g, catalyzer tosic acid 4g; Toluene 110mL, beginning stirring heating, 108-110 ℃ of back flow reaction 3-8h; Other conditions are with embodiment 1, and purifying gets product III b33g; ω III b:99.5%, yield: 70.5%, product mass spectrum result: ES-MS m/z:426 [M]+.
The present invention has selected bis cyclohexane and oxane as molecular skeleton, design to contain two hexanaphthene oxane class liquid crystalline cpd III, and with to alkyl dicyclohexyl formaldehyde structure shown in I; With 2-alkyl phenyl Ucar 35 structure such as II are depicted as raw material, wherein R, R ' and the R, the R ' that contain in two hexanaphthene oxane compounds III are identical in chemical compounds I, the II, adopt tosic acid to make catalyzer; With the organic solvent is reaction medium, at 35-200 ℃, and reaction 2-12h; Contained two hexanaphthene oxane compounds III accordingly, structure is wherein confirmed, confirmed that the mass ratio that adopts tosic acid to make catalyzer and starting compound I is 1%-20%; 1%-10% preferably; With the organic solvent is reaction medium, and organic solvent is toluene, YLENE, normal heptane, normal hexane equal solvent preferably, at 35-200 ℃ of reaction 2-12h.Preferably 60-110 ℃ of temperature of reaction system, the system reaction times is 3-8h preferably, is contained two hexanaphthene oxane compounds III accordingly, and through washing, extraction, recrystallization, its purified content is greater than 99%, and overall yield of reaction is greater than 70%.
Instrument and reagent
The SY25000 of Beijing Analytical Instrument Factory type high pressure liquid chromatograph (methyl alcohol is moving phase, and C218 is a stationary phase, flow velocity 1mL/min); Day island proper Tianjin LC-10ATvp type high pressure liquid chromatograph (methyl alcohol: acetonitrile=2:1, flow velocity 1mL/min); Day island proper Tianjin GC-14C, GC-17A gas chromatograph (DB-1 type pillar); 1102 type gas chromatographs (Shanghai analytical instrument factory); The HP5989B of U.S. Hewlett-Packard Corporation type mass spectrograph; Hewlett-Packard HP 5989B type mass spectrograph.
Tosic acid, analytical pure (chemical reagent purchasing station, Shanghai); Toluene, analytical pure (Shanghai reagent one factory); Anhydrous magnesium sulfate, analytical pure (four-way chemical plant, Tianjin); To n-propyl dicyclohexyl formaldehyde, n-pentyl dicyclohexyl formaldehyde and 2-are pressed the open source literature preparation to the ethylphenyl Ucar 35.
The present invention not only is confined to the instrument and the reagent of above-mentioned employing.
Claims (5)
1. a liquid crystal monomer contains two hexanaphthene oxane compounds, it is characterized in that this compound structure is following:
R is one of the straight chained alkyl of fluorine, chlorine, H, C1-C5, straight chain alkoxyl group of C1-C5 in the formula; R ' is one of straight chain alkoxyl group, cyanic acid of straight chained alkyl, the C1-C5 of fluorine, chlorine, H, C1-C5, and this compounds can be separately or is mixed for the liquid-crystal display of various display formats.
2. the said liquid crystal monomer of claim 1 contains the compound method of two hexanaphthene oxane compounds, it is characterized in that adopting following synthetic route:
Ⅰ Ⅱ Ⅲ
Is raw material to alkyl dicyclohexyl formaldehyde and the 2-of structure shown in II to the alkyl phenyl Ucar 35 with structure shown in I, and wherein R, R ' and the R, the R ' that contain in two hexanaphthene oxane compounds III are identical in chemical compounds I, the II, adopt tosic acid to make catalyzer; With the organic solvent is reaction medium, at temperature 35-200 ℃, and reaction 2-12h; Contained two hexanaphthene oxane compounds III accordingly, after having reacted, through washing; Extraction; Recrystallization, its purified ω III>99%, overall yield of reaction is greater than 70%.
3. a kind of liquid crystal monomer according to claim 2 contains the compound method of two hexanaphthene oxane compounds, it is characterized in that using the quality of catalyzer tosic acid is the 1%-20% of the quality of starting compound I.
4. a kind of liquid crystal monomer according to claim 2 contains the compound method of two hexanaphthene oxane compounds, and the described organic solvent of its characteristic is a kind of in toluene, YLENE, normal heptane, the normal hexane.
5. a kind of liquid crystal monomer according to claim 2 contains the compound method of two hexanaphthene oxane compounds, it is characterized in that temperature of reaction is 60-110 ℃, reaction times 3-8h.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201210337052.9A CN102838584B (en) | 2012-09-13 | 2012-09-13 | Liquid crystal monomer bicyclohexyl-containing epoxyethane compound and synthetic method thereof |
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| CN201210337052.9A CN102838584B (en) | 2012-09-13 | 2012-09-13 | Liquid crystal monomer bicyclohexyl-containing epoxyethane compound and synthetic method thereof |
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| CN102838584A true CN102838584A (en) | 2012-12-26 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107573948A (en) * | 2017-09-11 | 2018-01-12 | 陕西莱特光电材料股份有限公司 | A kind of Huan Ji Wan oxanes class liquid crystal monomer compound and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5209868A (en) * | 1989-04-08 | 1993-05-11 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Trifluoromethylcyclohexane derivatives |
| EP1362839A2 (en) * | 1998-06-02 | 2003-11-19 | Chisso Corporation | Liquid crystal composition having a delta-epsilon- of not less than zero and liquid crystal display device |
-
2012
- 2012-09-13 CN CN201210337052.9A patent/CN102838584B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5209868A (en) * | 1989-04-08 | 1993-05-11 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Trifluoromethylcyclohexane derivatives |
| EP1362839A2 (en) * | 1998-06-02 | 2003-11-19 | Chisso Corporation | Liquid crystal composition having a delta-epsilon- of not less than zero and liquid crystal display device |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107573948A (en) * | 2017-09-11 | 2018-01-12 | 陕西莱特光电材料股份有限公司 | A kind of Huan Ji Wan oxanes class liquid crystal monomer compound and preparation method thereof |
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Denomination of invention: The invention relates to a liquid crystal monomer containing bicyclohexane oxane compound and a synthetic method thereof Effective date of registration: 20211209 Granted publication date: 20141231 Pledgee: Yantai Bank Co.,Ltd. Haiyang sub branch Pledgor: SHANDONG SHENGHUA ELECTRONIC NEW MATERIAL CO.,LTD. Registration number: Y2021980014417 |
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Date of cancellation: 20221012 Granted publication date: 20141231 Pledgee: Yantai Bank Co.,Ltd. Haiyang sub branch Pledgor: SHANDONG SHENGHUA ELECTRONIC NEW MATERIAL CO.,LTD. Registration number: Y2021980014417 |
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