CN104130782B - A kind of dual-frequency liquid crystal material with low threshold frequency - Google Patents
A kind of dual-frequency liquid crystal material with low threshold frequency Download PDFInfo
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- CN104130782B CN104130782B CN201410342234.4A CN201410342234A CN104130782B CN 104130782 B CN104130782 B CN 104130782B CN 201410342234 A CN201410342234 A CN 201410342234A CN 104130782 B CN104130782 B CN 104130782B
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Abstract
The present invention announces a kind of dual-frequency liquid crystal material with low threshold frequency, the component A by 20.0 ~ 25.0%, the B component of 20.0 ~ 25.0%, 17.5 ~ 22.5% component C, component D, the component E of 7.5 ~ 12.5% of 7.5 ~ 12.5%, the component G of the component F of 5.0 ~ 10.0% and 5.0 ~ 10.0% formed by total amount 100% melting mixing; Wherein, component A is the series derivates with hexanaphthene fluoro tolane skeleton structure; B is the series derivates with fluoro tolane skeleton structure; C is the series derivates with hexanaphthene phenyl ring skeleton structure; D is the series derivates with tolane skeleton structure; E is the series derivates with three ring monoesters side fluorine-based end cyano group skeleton structures; F is the series derivates with triple-ring double easter side dicyano skeleton structure.This material has low threshold frequency, wider liquid crystal phase temperature and low viscosity, and the double frequency for the preparation of low-work voltage, response fast drives liquid crystal device.
Description
Technical field
The invention belongs to liquid crystal material technical field, be specifically related to a kind of dual-frequency liquid crystal material and the application thereof with low threshold frequency.
Background technology
The rodlike molecule pattern of liquid crystal determines the anisotropy that liquid crystal has optics, electricity etc., the principal character of dual-frequency liquid crystal is that specific inductivity reduces with the rising of ac frequency, under ac frequency lower (being less than 500Hz), dielectric anisotropy was greater than for zero (being equivalent to positivity liquid crystal), under ac frequency higher (being greater than 100kHz), dielectric anisotropy was less than for zero (being equivalent to negative liquid crystal), make dual-frequency liquid crystal dielectric anisotropy be zero frequency be called threshold frequency.Therefore this type of liquid crystal material is being parallel to molecular long axis and is all having stronger polarity perpendicular to molecular long axis.Therefore liquid crystalline cpd of the present invention has double frequency electric field driven characteristic, and namely under low-frequency ac electric field drives, dielectric anisotropy is greater than zero, and under high-frequency ac electric field drives, dielectric anisotropy is less than zero, is able to practical application on much photoelectricity and display equipment.
Dual-frequency liquid crystal has significant photoelectric characteristic, compared with nematic liquid crystal, it can reach by changing frequency the object that liquid crystal is rotated, and need not in the past by changing the mode of voltage, such dual-frequency liquid crystal just becomes the light valve that can be controlled by frequency, some opticinstruments uses dual-frequency liquid crystal can reduce driving voltage and the time of response of device greatly.Therefore it receives increasing concern in the application in the fields such as optics in recent years.But, current dual-frequency liquid crystal material threshold frequency higher (at more than 50kHz), and dual-frequency liquid crystal material has dielectric loss in high frequency, affects the work-ing life of liquid crystal device.And the higher driving arrangement volume providing high frequency that causes of threshold frequency is excessive, be unfavorable for the use of dual-frequency liquid crystal again on portable equipment.The effective way improving these problems is exactly design the dual-frequency liquid crystal of low threshold frequency.
Summary of the invention
The object of the present invention is to provide a kind of dual-frequency liquid crystal material with low threshold frequency, the threshold frequency≤15kHz of this liquid crystal material, this material is applicable to the photoelectric device, bistable display devices, building energy conservation film etc. of processability excellence.
For reaching above-mentioned purpose, the present invention is the wide temperature range low viscosity prepared and have the dual-frequency liquid crystal material of low threshold frequency (≤15kHz) by mixing various of monomer, the series derivates with hexanaphthene fluoro tolane skeleton structure by 20.0 ~ 25.0% is as component A, the series derivates with fluoro tolane skeleton structure of 20.0 ~ 25.0% is as B component, the series derivates with hexanaphthene phenyl ring skeleton structure of 17.5 ~ 22.5% is as component C, the series derivates with tolane skeleton structure of 7.5 ~ 12.5% is as component D, the series derivates with three ring monoesters side fluorine-based end cyano group skeleton structures of 7.5 ~ 12.5% is as component E, the series derivates with triple-ring double easter side dicyano skeleton structure of 5.0 ~ 10.0% is as component F, the series derivates with three phenyl ring dibasic acid esters side dicyan cardinal extremity cyano group skeleton structures of 5.0 ~ 10.0% is formed by total amount 100.0% melting mixing as component G.
Principle of the present invention is: component A provides the rigidity of molecule and lower ctystallizing point, and fluorine side base can reduce viscosity of material; The fluoro tolane of B component is conducive to improving the polarity of liquid crystal perpendicular to molecular long axis direction; The molecular weight of component C is little, and ctystallizing point is low, can widen nematic phase temperature range; Component D increases molecular conjugation, strengthens the dielectric anisotropy of liquid crystal; Component E provides simultaneously and is parallel to molecular long axis direction and the polarity perpendicular to molecular long axis direction, is conducive to double frequency modulation, and each component intermiscibility is better; Component F and G increases the polarity perpendicular to molecular long axis direction, has widened nematic phase temperature range.The liquid crystal that seven large classes are mixed by different chain length alkyl or alkoxy derivative, can reduce cocrystallization point, and broadening nematic phase temperature range also effectively eliminates smectic phase, finally reaches equilibrium and the optimum of properties, meets the demand of practical application.
Above-mentioned dual-frequency liquid crystal material, further, wherein component A molecular structure is that on tolane, a phenyl ring No. 4 positions are connected with hexanaphthene, and the hydrogen of another phenyl ring 2, No. 3 positions replaced by fluorine, end group R
1for the alkyl containing 1 to 9 carbon, end group R
2for containing the alkoxyl group of 1 to 9 carbon, component A is by any one in said derivative or multiplely mix with arbitrary proportion:
(wherein n is the integer of 1-9)
Further, wherein B component molecular structure is that the hydrogen of a phenyl ring 2, No. 3 positions on tolane replaced by fluorine, end group R
1for the alkyl containing 1 to 9 carbon, end group R
2for containing the alkoxyl group of 1 to 9 carbon, B component is by any one in said derivative or multiplely mix with arbitrary proportion:
(wherein n is the integer of 1-9)
Further, wherein component C molecular structure is that hexanaphthene is directly connected with phenyl ring, end group R
1for the alkyl containing 1 to 9 carbon, end group R
2for containing the alkoxyl group of 1 to 9 carbon, component C is by any one in said derivative or multiplely mix with arbitrary proportion:
(wherein n is the integer of 1-9)
Further, wherein component D molecular structure take tolane as skeleton, end group R
1for the alkyl containing 1 to 9 carbon, end group R
2for containing the alkoxyl group of 1 to 9 carbon, component D is by any one in said derivative or multiplely mix with arbitrary proportion:
(wherein n is the integer of 1-9)
Further, wherein component E molecular structure has three ring monoesters side fluorine, and phenyl ring No. 3 positions replaced by fluorine, and an end group is cyano group, another end group R
1for containing the alkyl of 1 to 9 carbon, component E is by any one in said derivative or multiplely mix with arbitrary proportion:
(wherein n is the integer of 1-9)
Further, wherein component F molecular structure take triple-ring double easter as skeleton, and middle phenyl ring 2, No. 3 positions are replaced by cyano group, two end group R
1for containing the alkyl of 1 to 9 carbon, component F is by any one in said derivative or multiplely mix with arbitrary proportion:
(wherein n is the integer of 1-9)
Further, wherein component G molecular structure is with three phenyl ring dibasic acid esters for skeleton, and middle phenyl ring 2, No. 3 positions are replaced by cyano group, end group R
1for containing the alkyl of 1 to 9 carbon, component G is by any one in said derivative or multiplely mix with arbitrary proportion:
(wherein n is the integer of 1-9)
The above-mentioned threshold frequency with the dual-frequency liquid crystal material of low threshold frequency is for being not more than 15kHz.
The above-mentioned purposes of dual-frequency liquid crystal material as the material of photoelectric display device, two state device and building energy conservation film with low threshold frequency.This liquid crystal material is also applicable to prepare trans PDLC or PSLC etc.
Beneficial effect of the present invention is:
The present invention is the wide temperature range low viscosity prepared and have the dual-frequency liquid crystal material of low threshold frequency (≤15kHz) by mixing A ~ G various ingredients, wherein, component A provides the rigidity of molecule and lower ctystallizing point, and fluorine side base can reduce viscosity of material; The fluoro tolane of B component is conducive to improving the polarity of liquid crystal perpendicular to molecular long axis direction; The molecular weight of component C is little, and ctystallizing point is low, can widen nematic phase temperature range; Component D increases molecular conjugation, strengthens the dielectric anisotropy of liquid crystal; Component E provides simultaneously and is parallel to molecular long axis direction and the polarity perpendicular to molecular long axis direction, is conducive to double frequency modulation, and each component intermiscibility is better; Component F and G increases the polarity perpendicular to molecular long axis direction, has widened nematic phase temperature range.The liquid crystal that seven large classes are mixed by different chain length alkyl or alkoxy derivative, can reduce cocrystallization point, and broadening nematic phase temperature range also effectively eliminates smectic phase, finally reaches equilibrium and the optimum of properties, meets the demand of practical application.
Liquid crystal material provided by the invention has low threshold frequency (≤15kHz), there is the feature of wider liquid crystal phase temperature (-40 ~ 100 DEG C) simultaneously, the double frequency driving liquid crystal device of low-work voltage, response fast can be prepared, be applicable to the Application Areas that display, photoelectric device etc. are wide.
Accompanying drawing explanation
Fig. 1 is the dielectric anisotropic of embodiment one dual-frequency liquid crystal material and the graph of relation of frequency.
Fig. 2 is the dielectric anisotropic of embodiment two dual-frequency liquid crystal material and the graph of relation of frequency.
Embodiment
Below by concrete enforcement, further detailed description is done to the present invention, but the scope do not limited the present invention in any way.
In the examples below, the dual-frequency liquid crystal material with low threshold frequency is formed by total amount 100.0% melting mixing by component A, the B component of 20.0 ~ 25.0%, component C, component D, the component E of 7.5 ~ 12.5% of 7.5 ~ 12.5%, the component G of the component F of 5.0 ~ 10.0% and 5.0 ~ 10.0% of 17.5 ~ 22.5% of 20.0 ~ 25.0%; Wherein, component A is the series derivates with hexanaphthene fluoro tolane skeleton structure; B component is the series derivates with fluoro tolane skeleton structure; Component C is the series derivates with hexanaphthene phenyl ring skeleton structure; Component D is the series derivates with tolane skeleton structure; Component E is the series derivates with three ring monoesters side fluorine-based end cyano group skeleton structures; Component F is the series derivates with triple-ring double easter side dicyano skeleton structure; Component G is the series derivates with three phenyl ring dibasic acid esters side dicyan cardinal extremity cyano group skeleton structures.In the embodiment of the present invention molecular structural formula of each component composition of liquid crystal material and proportional range as follows, wherein end group R
1for alkyl, end group R
2for alkoxyl group, n is the integer of 1-9:
Embodiment one:
Dual-frequency liquid crystal material by 21.63% component A (A-1:R
1=C
3h
7, R
2=OC
2h
5account for 12.38%; A-2:R
1=C
3h
7, R
2=OCH
3account for 9.25%), the B component (B-1:R of 21.78%
1=C
3h
7, R
2=OC
2h
5account for 8.52%; B-2:R
1=C
3h
7, R
2=OCH
3account for 9.38%; B-3:R
1=C
4h
9, R
2=OCH
3account for 3.88%), the component C (C-1:R of 19.84%
1=C
3h
7, R
2=OCH
3account for 12.01%; C-2:R
1=C
3h
7, R
2=OC
2h
5account for 7.83%), the component D (D-1:R of 9.42%
1=C
4h
9, R
2=OC
2h
5account for 4.85%; D-2:R
1=C
5h
11, R
2=OC
2h
5account for 4.57%), the component E (E:R of 11.45%
1=C
5h
11account for 11.45%), the component F (F-1:R of 8.38%
1=C
3h
7account for 4.26%; F-2:R
1=C
5h
11account for 4.12%), the component G (G-1:R of 7.50%
1=C
3h
7account for 3.55%; G-2:R
1=C
5h
11account for 3.95%) melting mixing formation.Each component composition molecular structural formula and ratio are as following table 1.
The molecular structural formula of each component composition of liquid crystal material and ratio in table 1 embodiment one
The physical properties of embodiment one reality test liquid crystal is as follows: clearing point Tc=102.2 DEG C, ctystallizing point Tm=-41.0 DEG C, degree of birefringence Δ n (589nm, 25 DEG C)=0.22, extraordinary ray refractive index n
e(589nm, 25 DEG C)=1.72, ordinary refraction index n
o(589nm, 25 DEG C)=1.50, viscosity γ (25 DEG C)=37.4mm
2/ s.
The relation of dielectric anisotropy and frequency as shown in Figure 1, dielectric anisotropy is first stabilized in about 2.25 in low-frequency range along with the increase of frequency, reduces gradually subsequently, when frequency reaches 14.6kHz, dielectric anisotropy is reduced to zero, so the threshold frequency of dual-frequency liquid crystal material is 14.6kHz; Along with frequency continue increase, dielectric anisotropy increases to zero after being first progressively reduced to-6.98.This is because liquid crystal molecule vibrates the speed having little time to adapt to direction of an electric field change, the specific inductivity being parallel to molecular long axis constantly reduces with the rising of frequency, and it is less by frequency influence in low-frequency range perpendicular to the specific inductivity of molecular long axis, change is little, also constantly reduce with the rising of frequency at high band, the speed reduced is faster, no longer changes with frequency at high frequency range specific inductivity.
Embodiment two:
Dual-frequency liquid crystal material by 21.80% component A (A-1:R
1=C
3h
7, R
2=OC
2h
5account for 11.55%; A-2:R
1=C
3h
7, R
2=OCH
3account for 10.25%), the B component (B-1:R of 20.52%
1=C
3h
7, R
2=OC
2h
5account for 10.43%; B-2:R
1=C
3h
7, R
2=OCH
3account for 10.09%), the component C (C-1:R of 23.36%
1=C
3h
7, R
2=OCH
3account for 13.54%; C-2:R
1=C
3h
7, R
2=OC
2h
5account for 9.82%), the component D (D-1:R of 11.46%
1=C
3h
7, R
2=OC
2h
5account for 5.34%; D-2:R
1=C
5h
11, R
2=OC
2h
5account for 6.12%), the component E (E-1:R of 11.36%
1=C
5h
11account for 5.88%, E-2:R
1=C
3h
7account for 5.48%), the component F (F-1:R of 6.37%
1=C
3h
7account for 3.15%; F-2:R
1=C
5h
11account for 3.22%), the component G (G-1:R of 5.13%
1=C
3h
7account for 2.17%; G-2:R
1=C
5h
11account for 2.96%) melting mixing formation.Each component composition molecular structural formula and ratio are as following table 2.
The molecular structural formula of each component composition of liquid crystal material and ratio in table 2 embodiment two
The physical properties of embodiment two reality test liquid crystal is as follows: clearing point Tc=97.5 DEG C, ctystallizing point Tm=-40.1 DEG C, degree of birefringence Δ n (589nm, 25 DEG C)=0.21, extraordinary ray refractive index n
e(589nm, 25 DEG C)=1.71, ordinary refraction index n
o(589nm, 25 DEG C)=1.50, viscosity γ (25 DEG C)=34.0mm
2/ s.
The relation of dielectric anisotropy and frequency as shown in Figure 2, dielectric anisotropy reduces along with the increase of frequency is first stabilized in about 1.75 subsequently gradually in low-frequency range, when frequency reaches 15.0kHz, dielectric anisotropy is reduced to zero, so the threshold frequency of dual-frequency liquid crystal material is 15.0kHz; Along with frequency continue increase, dielectric anisotropy increases to zero after being first progressively reduced to-0.81.Relative to embodiment one, the present embodiment increases the content of component C, decreases the content of component F and G, and overall dielectric constant is reduced, and viscosity reduces, and threshold frequency increases to some extent.Reason is that component F and G specific inductivity are comparatively large, and viscosity is also comparatively large, and wherein side base dicyanogen methyl isophorone and middle two ester groups have very big contribution to dual frequency characteristics.Embodiment one and embodiment two can be applied in different aspects according to different demand.
The above is only preferred embodiment of the present invention, and be not restriction the present invention being made to other form, any those skilled in the art may utilize the technology contents of above-mentioned announcement to be changed or be modified as the Equivalent embodiments of equivalent variations.But everyly do not depart from technical solution of the present invention content, any simple modification, equivalent variations and the remodeling done above embodiment according to technical spirit of the present invention, still belong to the protection domain of technical solution of the present invention.
Claims (3)
1. one kind has the dual-frequency liquid crystal material of low threshold frequency, it is characterized in that, the component A by 20.0 ~ 25.0%, the B component of 20.0 ~ 25.0%, 17.5 ~ 22.5% component C, component D, the component E of 7.5 ~ 12.5% of 7.5 ~ 12.5%, the component G of the component F of 5.0 ~ 10.0% and 5.0 ~ 10.0% formed by total amount 100.0% melting mixing;
Described component A is the series derivates with hexanaphthene fluoro tolane skeleton structure, and the molecular structural formula of described component A is formula 1:
Wherein end group R
1for alkyl, end group R
2for alkoxyl group, n is the integer of 1 ~ 9; Described component A is that any one or more in the derivative of formula 1 mixes with arbitrary proportion by molecular structural formula;
Described B component is the series derivates with fluoro tolane skeleton structure, and the molecular structural formula of described B component is formula 2:
Wherein end group R
1for alkyl, end group R
2for alkoxyl group, n is the integer of 1 ~ 9; Described B component is that any one or more in the derivative of formula 2 mixes with arbitrary proportion by molecular structural formula;
Described component C is the series derivates with hexanaphthene phenyl ring skeleton structure, and the molecular structural formula of described component C is formula 3:
Wherein end group R
1for alkyl, end group R
2for alkoxyl group, n is the integer of 1 ~ 9; Described component C is that any one or more in the derivative of formula 3 mixes with arbitrary proportion by molecular structural formula;
Described component D is the series derivates with tolane skeleton structure, and the molecular structural formula of described component D is formula 4:
Wherein end group R
1for alkyl, end group R
2for alkoxyl group, n is the integer of 1 ~ 9; Described component D is that any one or more in the derivative of formula 4 mixes with arbitrary proportion by molecular structural formula;
Described component E is the series derivates with three ring monoesters side fluorine-based end cyano group skeleton structures, and the molecular structural formula of described component E is formula 5:
Wherein end group R
1for alkyl, n is the integer of 1 ~ 9; Described component E is that any one or more in the derivative of formula 5 mixes with arbitrary proportion by molecular structural formula;
Described component F is the series derivates with triple-ring double easter side dicyano skeleton structure, and the molecular structural formula of described component F is formula 6:
Wherein end group R
1for alkyl, n is the integer of 1 ~ 9; Described component F is that any one or more in the derivative of formula 6 mixes with arbitrary proportion by molecular structural formula;
Described component G is the series derivates with three phenyl ring dibasic acid esters side dicyan cardinal extremity cyano group skeleton structures, and the molecular structural formula of described component G is formula 7:
Wherein end group R
1for alkyl, n is the integer of 1 ~ 9; Described component G is that any one or more in the derivative of formula 7 mixes with arbitrary proportion by molecular structural formula.
2. have the dual-frequency liquid crystal material of low threshold frequency according to claim 1, it is characterized in that, the threshold frequency of described liquid crystal material is for being not more than 15kHz.
3. there is described in claim 1 purposes of dual-frequency liquid crystal material as the material of photoelectric display device, two state device and building energy conservation film of low threshold frequency.
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| TWI556029B (en) * | 2015-04-17 | 2016-11-01 | 國立臺灣科技大學 | Fabricating method of liquid crystal device |
| CN106701105B (en) * | 2015-11-16 | 2020-01-17 | 北京大学 | Dual-frequency driving liquid crystal mixture with low critical switching frequency |
| CN106433688B (en) * | 2016-09-18 | 2018-08-24 | 陕西师范大学 | One kind tolane liquid crystal molecule of base containing pyridyl end and its preparation method and application |
| CN107338057B (en) * | 2017-07-10 | 2018-05-04 | 深圳市擎亮科技有限公司 | Dual-frequency liquid crystal composition, liquid crystal handwriting device, display device and light modulating device |
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| CN102199431A (en) * | 2010-03-26 | 2011-09-28 | 默克专利股份有限公司 | Liquid crystalline medium and liquid crystal device |
| CN103207469A (en) * | 2013-03-18 | 2013-07-17 | 北京京东方光电科技有限公司 | Liquid crystal display panel and production method thereof and display device |
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| CN102199431A (en) * | 2010-03-26 | 2011-09-28 | 默克专利股份有限公司 | Liquid crystalline medium and liquid crystal device |
| CN103207469A (en) * | 2013-03-18 | 2013-07-17 | 北京京东方光电科技有限公司 | Liquid crystal display panel and production method thereof and display device |
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