CN103555346B - 1, 3-dioxolane liquid crystal compound as well as preparation method and application thereof - Google Patents
1, 3-dioxolane liquid crystal compound as well as preparation method and application thereof Download PDFInfo
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- CN103555346B CN103555346B CN201310546010.0A CN201310546010A CN103555346B CN 103555346 B CN103555346 B CN 103555346B CN 201310546010 A CN201310546010 A CN 201310546010A CN 103555346 B CN103555346 B CN 103555346B
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Abstract
The invention relates to a 1, 3-dioxolane liquid crystal compound, which has a specific structural formula shown as a formula (I). The invention further provides a preparation method and an application of the 1, 3-dioxolane liquid crystal compound. A liquid crystal composition with the compound provided by the invention is short in response time, moderate in deltan numerical value and high in charge retention rate, and has a low threshold voltage and a wide application prospect.
Description
Technical field
The present invention relates to a kind of liquid crystalline cpd and comprise the liquid-crystal composition of described liquid crystalline cpd, more particularly, the present invention relates to a kind of 1,3-dioxolane class liquid crystalline cpd and preparation method and application.
Background technology
In recent years, the Application Areas of liquid crystalline cpd is more and more wider, has been widely used in various types of display equipment, Electrooptical devices, sensor.Wherein, nematic liquid crystal has the broadest purposes in a display device.Nematic liquid crystal has been widely used in passive TN or STN matrix display and has had in the system of tft active matrix.
Liquid crystal material requires to possess good chemistry and thermostability, the good stability to electric field and electromagnetic radiation, wider nematic temperature range, suitable specific refractory power, dielectric anisotropy, faster response speed and high voltage retention.
Along with the development of technique of display, higher requirement be it is also proposed to liquid crystal material, especially in quick response, reduce driving voltage, reduce the aspects such as power consumption.Therefore, the novel liquid crystal compound of the more improvement performances of exploitation is needed.
Summary of the invention
The object of this invention is to provide a kind of 1,3-dioxolane class liquid crystalline cpd.
Another object of the present invention is to provide a kind of preparation method of 1,3-dioxolane class liquid crystalline cpd.
Another object of the present invention is to provide a kind of application of 1,3-dioxolane class liquid crystalline cpd.
For solving the problem, the present invention adopts following technical scheme:
A kind of 1,3-dioxolane class liquid crystalline cpd, has following general structure (I):
In formula: R
1expression-H, has alkyl or the alkoxyl group of 1-12 carbon atom; Wherein, the H in alkyl or alkoxyl group can be optionally substituted by halogen, one or more-CH
2-can be replaced by-C ≡ C-,-CH=CH-,-CF=CF-,-CF=CH-,-CO-O-,-O-CO-or-O-independently of one another, but require that O atom does not directly connect each other;
R
2expression-H ,-F ,-Cl ,-CN ,-NCS ,-CF
3,-OCF
3,-OCF
2cl, has alkyl or the alkoxyl group of 1-12 carbon atom; Wherein, the H in alkyl or alkoxyl group can be optionally substituted by halogen, one or more-CH
2-can be replaced by-C ≡ C-,-CH=CH-,-CF=CF-,-CF=CH-,-CO-O-,-O-CO-or-O-independently of one another, but require that O atom does not directly connect each other;
A
2represent Isosorbide-5-Nitrae-phenylene or cyclohexyl, wherein, the H in Isosorbide-5-Nitrae-phenylene or cyclohexyl can be replaced by fluorine atoms or 1-2-CH-group can be replaced by nitrogen-atoms;
A
1, A
3, A
4, A
5identical or different, represent Isosorbide-5-Nitrae-cyclohexylidene independently of one another, Isosorbide-5-Nitrae-phenylidene or Isosorbide-5-Nitrae-phenylene; Wherein, 1-4 H in Isosorbide-5-Nitrae-cyclohexylidene and Isosorbide-5-Nitrae-phenylidene can be replaced by fluorine atoms, 1-2-CH
2-group can be replaced by Sauerstoffatom; 1-4 H in Isosorbide-5-Nitrae-phenylene can be replaced by fluorine atoms, and 1-2-CH-group can be replaced by nitrogen-atoms;
Z
1, Z
2, Z
3identical or different, represent carbon-carbon single bond ,-CO-O-,-O-CO-,-CF independently of one another
2o-,-OCF
2-,-CH
2o-,-OCH
2-,-CH
2cH
2-,-C ≡ C-,-CH=CH-,-CF=CF-,-CF=CH-,-CF
2cH
2-,-CH
2cF
2-,-C
2f
4-,-CH
2cHF-,-CHFCH
2-;
A, b, c are identical or different, represent 0,1,2 independently of one another;
In some preferred embodiments, R
1expression-H, has alkyl or the alkoxyl group of 1-8 carbon atom; Wherein, the H in alkyl or alkoxyl group can be optionally substituted by halogen, one or more-CH
2-can be replaced by-CH=CH-or-O-independently of one another, but require that O atom does not directly connect each other;
R
2expression-H ,-F ,-Cl ,-CN ,-CF
3,-OCF
3,-OCF
2cl, has alkyl or the alkoxyl group of 1-8 carbon atom; Wherein, the H in alkyl or alkoxyl group can be optionally substituted by halogen, one or more-CH
2-can be replaced by-CH=CH-or-O-independently of one another, but require that O atom does not directly connect each other;
A
1, A
3, A
4, A
5identical or different, represent independently of one another
Z
1, Z
2, Z
3identical or different, represent carbon-carbon single bond ,-CO-O-,-CF independently of one another
2o-,-CH
2o-,-CH
2cH
2-,-C ≡ C-,-CH=CH-,-CF=CF-,-C
2f
4-.
More preferably, in some embodiments, A
1, A
3, A
4, A
5identical or different, represent independently of one another
Z
1, Z
2, Z
3identical or different, represent carbon-carbon single bond ,-CO-O-,-CF independently of one another
2o-,-CH
2o-,-CH
2cH
2-,-C ≡ C-,-CH=CH-.
A, b, c are identical or different, represent 0,1 independently of one another, and 1≤a+b+c≤3;
In some preferred embodiments, the compound of logical formula I is particularly preferably one or more of following compound:
Wherein R
1represent-H or there is the alkyl of 1-7 carbon atom; R
2expression-H ,-F ,-Cl ,-CN ,-CF
3,-OCF
3, there is alkyl or the alkoxyl group of 1-7 carbon atom; Wherein, the one or more-CH in alkyl or alkoxyl group
2-can be replaced by-CH=CH-independently of one another.
The synthetic route of the compound of general structure of the present invention (I) is as follows:
The synthetic route of said structure general formula (I), specifically comprises the steps:
1) take toluene as reaction solvent, compound 1-1 and compound 1-2, under the effect of catalyzer tosic acid, is heated to back flow reaction 1-3h, by extraction, and washing, dry, suction filtration, cross silicagel column, concentrating under reduced pressure falls solvent and obtains compound 1-3;
2) in nitrogen protection, under-60--90 DEG C of condition, compound 1-3 and n-Butyl Lithium react 0.5-2h in tetrahydrofuran solvent, then react with difluorodibromomethane, are naturally warming up to-30 DEG C of stopped reaction, carry out conventional aftertreatment and obtain compound 1-4;
3) in nitrogen protection, 70-120 DEG C, under Tetrabutyl amonium bromide katalysis; compound 1-4 and compound 1-5 reacts 5-10h through Williamson ether synthesis (Williamson Synthesis) in water, then through hcl acidifying, extraction; washing, drying obtains compound 1-6.
In said synthesis route, in step 1), compound 1-1 and compound 1-2 starts a point water 95 DEG C time, continues substantially no longer to divide water outlet when being warming up to 113 DEG C; Described compound 1-1: compound 1-2: tosic acid molar ratio is 1:0.8-1.2:0.04-0.05;
In step 2) in, temperature of reaction is preferably-75--85 DEG C; Described compound 1-3: n-Butyl Lithium: difluorodibromomethane molar ratio is 1:0.9-1.1:1.0-1.2;
In step 3), temperature of reaction is preferably 80-110 DEG C; Described compound 1-4: compound 1-5: the molar ratio 1:1.0-1.1:0.1-0.15 of Tetrabutyl amonium bromide;
Wherein, R
1, R
2, A
1, A
2, A
3, A
4, A
5, Z
1, Z
2, Z
3, that a, b, c refer to scope is the same.
Above-mentioned
difluorodibromomethane, n-Butyl Lithium etc. all can be obtained by itself known method synthesis in open commercial sources or document.
The present invention also provides a kind of liquid-crystal composition, wherein comprises the compound of the general formula (I) that mass percent is 1-50%, and preferred mass per-cent is the compound of the general formula (I) of 3-25%.
Above-mentioned liquid-crystal composition is applied in TN, IPS, FFS, ADS-TFT Mode panel.
Beneficial effect of the present invention is as follows: the liquid-crystal composition adding the compounds of this invention, and the time of response is short, Δ n numerical value is moderate, electric charge conservation rate is high, and has lower threshold voltage, has a extensive future.
Embodiment
Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.
Described starting material if no special instructions, all can obtain from open commercial sources.
" conventional aftertreatment " refers to, in aqueous, mixed solution methylene dichloride, ethyl acetate or toluene extract, separatory, washing, dry and vacuum rotary evaporator evaporation, then product underpressure distillation or recrystallization and/or chromatography purification.
Embodiment 1
The synthetic line of compound (BYLC-01):
1) add 1.8mol compound 1,1.8mol compound 2,15g tosic acid in 5L there-necked flask, 2L toluene, opens stirring, is heated to back flow reaction 3h.
Aftertreatment: be cooled to less than 60 DEG C, adds 1.5L water in 5L bottle, stirs 5min, separatory, aqueous phase (1L × 3) methylbenzene extraction 3 times, merge organic phase, (1L × 3) washing 3 times, anhydrous sodium sulfate drying, suction filtration, filtrate crosses silicagel column, and 3 times of post height toluene rush post, and concentrating under reduced pressure is spin-dried for, add 190ml ethanol, freeze case (-30 DEG C) 6h, suction filtration, dry to obtain 1.44mol compound 3, GC:99%, yield: 80%.
2) 5L low-temperature reactor; nitrogen protection; add 1.44mol compound 3,2L THF wherein; open liquid nitrogen cooling extremely-75 DEG C after stirring--85 DEG C; start to drip 1.44mol n-Buli(n-Butyl Lithium); process temperature control-75 DEG C--85 DEG C, dropwise the reaction of rear temperature control 1h, rear dropping 1.5molCF
2br
2, process temperature control-75 DEG C--85 DEG C, dropwise, natural temperature reaction is to-30 DEG C of direct aftertreatments.
Aftertreatment: the mixing solutions (PH<5) dripping the dense HCl+0.5L water of 140g to reaction solution, stirs 0.5h, separatory, aqueous phase (0.5L × 2) methylbenzene extraction twice, merges organic phase and is washed to neutrality (2L/ time, about 2 times), organic phase anhydrous sodium sulfate drying, suction filtration, filtrate crosses silicon gel column, 3 times of post height toluene rinse pillars, merged post liquid to concentrate, obtain 1.44mol compound 4, GC content 65.8%(main peak), yield 100%.
3) reaction unit of 5L there-necked flask, adds 2L water, 50g Tetrabutyl amonium bromide, and 1.44mol compound 4,1.6mol compound 5, is warming up to backflow under stirring, and backflow 6h, controls GC(raw material in rear sampling) <2%, start aftertreatment.
Aftertreatment: add toluene 1L in reaction solution, stirs, separatory, aqueous phase (0.5L × 2) methylbenzene extraction twice, merges organic phase (0.5L × 2) washing 2 times, organic phase anhydrous sodium sulfate drying, suction filtration, filtrate crosses silicon gel column, 3 times of post height toluene rinse pillars, cross post liquid concentrating under reduced pressure, 500ml ethanol 80 DEG C is put in refrigerator-freezer recrystallization (freezing 3h), rear suction filtration after dissolving, and dries to obtain 0.63mol compound 6(BYLC-01), GC content 99%, yield 44%.
After measured: GC-MS:582(molecular ion peak), 435(methoxyl group bridged bond fracture);
1h-NMR (300MHz, CDCl
3): 7.0-6.6(m, 5H), 6.3-6.1(m, 2H) and, 6.0-5.7 (m, 1H), 1.5-0.7(m, 21H).
Embodiment 2
The synthetic line of compound (BYLC-02):
1) add 1.8mol compound 1,1.8mol compound 2,15g tosic acid in 5L there-necked flask, 2L toluene, opens stirring, is heated to backflow, reaction 3h.
Aftertreatment: be cooled to less than 60 DEG C, adds 1.5L water in 5L bottle, stirs 5min, separatory, aqueous phase (1L × 3) methylbenzene extraction 3 times, merge organic phase, (1L × 3) washing 3 times, dried over sodium sulfate, crosses silicagel column, 3 times of post height toluene rush post, and concentrating under reduced pressure is spin-dried for, and adds 200ml ethanol, freeze case (-30 DEG C) 6h, suction filtration, dry to obtain 1.26mol compound 3, GC:99%, yield: 70%.
2) 5L low-temperature reactor, nitrogen protection, adds 1.44mol compound 3,2L THF wherein; open and stir lower rear liquid nitrogen cooling to-75 DEG C--85 DEG C, starting to drip 1.44mol n-Buli, process temperature control-75 DEG C--85 DEG C; dropwise the reaction of rear temperature control 1h, rear dropping 1.5molCF
2br
2, process temperature control-75 DEG C--85 DEG C, dropwise, be naturally warming up to-30 DEG C of direct aftertreatments.
Aftertreatment: the mixing solutions (PH<5) dripping the dense HCl+0.6L water of 160g to reaction solution, stirs 0.5h, separatory, aqueous phase toluene 0.5L × 2 extract twice, merge organic phase and are washed to neutrality (2L/ time, about 2 times), organic phase anhydrous sodium sulfate drying, suction filtration, filtrate crosses silicon gel column, cross post complete, with 3 times of post height toluene rinse pillars, merged post liquid and concentrated, obtained 1.44mol compound 4, GC(main peak) content 59%, yield 100%.
3) reaction unit of 5L there-necked flask, adds 2L water, 50g Tetrabutyl amonium bromide, 1.44mol compound 4,1.6mol compound 5, after be warming up to backflow, backflow 6h, control GC raw material <2% in rear sampling, start aftertreatment.
Aftertreatment: add 1L toluene in reaction solution, stirs, separatory, aqueous phase (0.5L × 2) methylbenzene extraction twice, merges organic phase, (0.5L × 2) washing 2 times, organic phase anhydrous sodium sulfate drying, suction filtration, filtrate crosses silicon gel column, 3 times of post height toluene rinse pillars, cross post liquid concentrating under reduced pressure, 600ml ethanol 80 DEG C is put in refrigerator-freezer recrystallization (freezing 3h) after dissolving, rear suction filtration, dry to obtain 0.69mol compound 6(BYLC-02), GC content 99%, yield 48%.
After measured: GC-MS:500(molecular ion peak), 353(methoxyl group bridged bond fracture);
1H-NMR(300MHz,CDCl
3):7.1-6.5（m,7H），6.0-5.8（m,1H）,2.5-0.8(m,11H)。
Embodiment 3
With
replace
, compd B YLC-03 can be obtained according to the method for embodiment 2:
After testing, GC content 99.8%, yield 80.8%.
GC-MS:612(molecular ion peak), 353(methoxyl group bridged bond ruptures);
1H-NMR(300MHz,CDCl
3):6.1-7.0（m,9H），5.6-6.2(m,1H)，0.7-2.6（m,11H）。
Embodiment 4
The liquid crystalline cpd used in following composition is all provided by Beijing Bayi Space LCD Materials Technology Co., Ltd..Except specified otherwise, in embodiment, the content of each component all represents mass percent.
In the present invention, each performance test parameter shorthand is as follows:
△ n is optical anisotropy, n
ofor specific refractory power (589nm, 20 DEG C);
V
10for threshold voltage, be the character voltage (V, 20 DEG C) when transmitance changes 10%, V
90for saturation voltage, be character voltage when transmitance changes 90% (V, 20 DEG C); Liquid crystal comprehensive parameter tester EOT-5016.The polaroid that setting polarizing axis is orthogonal, is attached to testing cassete (4.0 μm) top and bottom being marked with liquid crystal by polaroid.To liquid crystal cell making alive, the voltage when light is reduced to 10% transmitance from the original state of full impregnated is saturation voltage.Light source is halogen light, and the square wave of liquid crystal cell 64HZ drives.
Cp is the clearing point (DEG C) of liquid-crystal composition;
τ on is that τ off is that τ is the τ on+ τ off(time of response until reach time when transmitance 10% is cut off until time when reaching transmitance 90%) (ms).
VHR electric charge conservation rate (%): injected by mixed liquid crystal in liquid crystal cell, put into thermostat container, after temperature DEG C is stablized, enters test procedure, manually gets and a little obtain electric charge conservation rate numerical value.Measuring voltage is 5V, and power-up time is 5ms, Holding Time is 500ms.
Get the liquid crystalline cpd of following parts by weight and prepare liquid-crystal composition, the performance perameter of concrete proportioning and the liquid-crystal composition of gained is by shown in following table.
The application of liquid crystalline cpd of the present invention in IPS, FFS, ADS-TFT pattern, result is as following table:
Table 1.1 adds the weight percent of each component in the liquid-crystal composition 1 of the compounds of this invention
The performance perameter of table 1.2 liquid-crystal composition 1
| Performance perameter | Parameter value |
| △n | 0.1010 |
| Δε | +7.0 |
| V 10 | 1.25 |
| η | 12 |
| Cp | 94 |
| τ | 10 |
| VHR | 99% |
Table 2.1 adds the weight percent of each component in the liquid-crystal composition 2 of the compounds of this invention
The performance perameter of table 2.2 liquid-crystal composition 2
| Performance perameter | Parameter value |
| △n | 0.1020 |
| Δε | +9.3 |
| V 10 | 1.15 |
| η | 12 |
| Cp | 80 |
| τ | 8 |
| VHR | 99% |
Table 3.1 does not add the weight percent of each component of liquid-crystal composition 3 of the compounds of this invention
The performance perameter of table 3.2 liquid-crystal composition 3
| Performance perameter | Parameter value |
| △n | 0.098 |
| Δε | +9.3 |
| V 10 | 1.15 |
| η | 21 |
| Cp | 100 |
| τ | 15 |
| VHR | 97% |
As can be seen from table 1.2, table 2.2, table 3.2: add the liquid-crystal composition 1 of the compounds of this invention, liquid-crystal composition 2 compares the liquid-crystal composition 3 not adding the compounds of this invention, time of response is shorter, Δ n numerical value is moderate, electric charge conservation rate is higher, and there is lower threshold voltage, be particularly useful for the TFT display mode of fast-response.The add-on of the compound of general structure of the present invention (I) is advisable with 1-50%, more preferably 3-35%.
Except the composition that test example exemplifies, other liquid-crystal compositions adding other the compounds of this invention provided by the invention composition can obtain optical property excellent equally.
Although above the present invention is described in detail with a general description of the specific embodiments, on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (10)
1. a dioxolane class liquid crystalline cpd, is characterized in that, has following general structure (I):
In formula: R
1expression-H, has alkyl or the alkoxyl group of 1-12 carbon atom; Wherein, the H in alkyl or alkoxyl group can be optionally substituted by halogen, one or more-CH
2-can be replaced by-C ≡ C-,-CH=CH-,-CF=CF-,-CF=CH-,-CO-O-,-O-CO-or-O-independently of one another, but require that O atom does not directly connect each other;
R
2expression-H ,-F ,-Cl ,-CN ,-NCS ,-CF
3,-OCF
3,-OCF
2cl, has alkyl or the alkoxyl group of 1-12 carbon atom; Wherein, the H in alkyl or alkoxyl group can be optionally substituted by halogen, one or more-CH
2-can be replaced by-C ≡ C-,-CH=CH-,-CF=CF-,-CF=CH-,-CO-O-,-O-CO-or-O-independently of one another, but require that O atom does not directly connect each other;
A
2represent Isosorbide-5-Nitrae-phenylene or cyclohexyl, wherein, the H in Isosorbide-5-Nitrae-phenylene or cyclohexyl can be replaced by fluorine atoms or 1-2-CH-group can be replaced by nitrogen-atoms;
A
1, A
3, A
4, A
5identical or different, represent Isosorbide-5-Nitrae-cyclohexylidene independently of one another, Isosorbide-5-Nitrae-phenylidene or Isosorbide-5-Nitrae-phenylene; Wherein, 1-4 H in Isosorbide-5-Nitrae-cyclohexylidene and Isosorbide-5-Nitrae-phenylidene can be replaced by fluorine atoms, 1-2-CH
2-group can be replaced by Sauerstoffatom; 1-4 H in Isosorbide-5-Nitrae-phenylene can be replaced by fluorine atoms, and 1-2-CH-group can be replaced by nitrogen-atoms;
Z
1, Z
2, Z
3identical or different, represent carbon-carbon single bond ,-CO-O-,-O-CO-,-CF independently of one another
2o-,-OCF
2-,-CH
2o-,-OCH
2-,-CH
2cH
2-,-C ≡ C-,-CH=CH-,-CF=CF-,-CF=CH-,-CF
2cH
2-,-CH
2cF
2-,-C
2f
4-,-CH
2cHF-,-CHFCH
2-;
A, b, c are identical or different, represent 0,1,2 independently of one another.
2. compound according to claim 1, is characterized in that, described R
1expression-H, has alkyl or the alkoxyl group of 1-8 carbon atom; Wherein, the H in alkyl or alkoxyl group can be optionally substituted by halogen, one or more-CH
2-can be replaced by-CH=CH-or-O-independently of one another, but require that O atom does not directly connect each other.
3. compound according to claim 1, is characterized in that, described R
2expression-H ,-F ,-Cl ,-CN ,-CF
3,-OCF
3,-OCF
2cl, has alkyl or the alkoxyl group of 1-8 carbon atom; Wherein, the H in alkyl or alkoxyl group can be optionally substituted by halogen, one or more-CH
2-can be replaced by-CH=CH-or-O-independently of one another, but require that O atom does not directly connect each other.
4. compound according to claim 1, is characterized in that, described A
1, A
3, A
4, A
5identical or different, represent independently of one another
5. compound according to claim 1, is characterized in that, described Z
1, Z
2, Z
3identical or different, represent carbon-carbon single bond ,-CO-O-,-CF independently of one another
2o-,-CH
2o-,-CH
2cH
2-,-C ≡ C-,-CH=CH-,-CF=CF-,-C
2f
4-.
6. compound according to claim 1, is characterized in that, described a, b, c are identical or different, represents 0,1 independently of one another, and 1≤a+b+c≤3.
7. compound according to claim 1, is characterized in that, the compound of described logical formula I is one or more of following compound:
Wherein R
1represent-H or there is the alkyl of 1-7 carbon atom; R
2expression-H ,-F ,-Cl ,-CN ,-CF
3,-OCF
3, there is alkyl or the alkoxyl group of 1-7 carbon atom; Wherein, the one or more-CH in alkyl or alkoxyl group
2-can be replaced by-CH=CH-independently of one another.
8. the preparation method of the compound of the arbitrary described general structure (I) of claim 1-7, it is characterized in that, synthetic route is as follows:
Described synthetic route specifically comprises the steps:
1) take toluene as reaction solvent, compound 1-1 and compound 1-2, under the effect of catalyzer tosic acid, is heated to back flow reaction 1-3h, by extraction, and washing, dry, suction filtration, cross silicagel column, concentrating under reduced pressure falls solvent and obtains compound 1-3;
2) in nitrogen protection, under-60--90 DEG C of condition, compound 1-3 and n-Butyl Lithium react 0.5-2h in tetrahydrofuran solvent, then react with difluorodibromomethane, are naturally warming up to-30 DEG C of stopped reaction, carry out conventional aftertreatment and obtain compound 1-4;
3) in nitrogen protection, 70-120 DEG C, under Tetrabutyl amonium bromide katalysis, compound 1-4 and compound 1-5 reacts 5-10h through Williamson ether synthesis (Williamson Synthesis) in water, then through hcl acidifying, extraction, washing, drying obtains compound 1-6;
Wherein R
1, R
2, A
1, A
2, A
3, A
4, A
5, Z
1, Z
2, Z
3, a, b, c refer to scope with claim 1.
9. a liquid-crystal composition, is characterized in that, comprises the compound that mass percent is the arbitrary described general formula (I) of claim 1-7 of 1-50%.
10. the application of liquid-crystal composition described in claim 9 in TN, IPS, FFS, ADS-TFT pattern.
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| CN1504468A (en) * | 2002-12-02 | 2004-06-16 | 石家庄实力克液晶材料有限公司 | Substituted benzo 1,3-dioxygen pentacyclic ring derivative, preparing process and uses thereof |
| CN103087038A (en) * | 2012-12-24 | 2013-05-08 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing benzo-1, 3-dioxolane and difluoro-methylenedioxy bridge |
| CN103087039A (en) * | 2013-01-22 | 2013-05-08 | 河南师范大学 | Synthesis method of poly-substituted benzene[1,3]meta-ditetrahydrofuran compound |
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