CN109749755A - A kind of liquid-crystal compounds and composition improving liquid crystal material environmental suitability - Google Patents
A kind of liquid-crystal compounds and composition improving liquid crystal material environmental suitability Download PDFInfo
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Abstract
The invention discloses a kind of nematic phase liquid crystal compositions, it is characterised in that the compound comprising one or more general structures (1):Wherein R is straight chained alkyl, alkenyl, the alkoxy of carbon number 1~9；X1~X4For methyl, chlorine atom, fluorine atom or hydrogen atom, and wherein X1~X4At least one is methyl or chlorine atom.The present invention has the characteristics that high environmental suitability, mesophase range are wide, is suitable for the liquid crystal display modes such as TFT liquid crystal display, especially TN, IPS, FFS, OCB, blue phase.
Description
Technical field
The invention belongs to liquid crystal material technical fields, and in particular to a kind of liquid-crystalization for improving liquid crystal material environmental suitability
Close object and composition.
Background technique
Liquid crystal display has many advantages, such as panelized, low in energy consumption, light-weight, radiationless, develops in field of information display fast
Speed.Liquid crystal display realizes display function using the optical anisotropy of liquid crystal material and the characteristic of dielectric anisotropy.It presses
Classify according to display pattern, there is twisted-nematic formula (TN), super twisted nematic formula (STN), dynamic scattering mode (DSP), film crystal
Pipe drive mode (TFT) etc..Full color, high-resolution, wide viewing angle, quick response etc. may be implemented in TFT liquid crystal display, has obtained
It is most important display technology currently on the market to extensive use.
Liquid crystal material used in liquid crystal display in use environment temperature range, usually -20 DEG C~+70 DEG C have to
Column phase；Must have chemical stability with height simultaneously, the birefringence of lower viscosity and suitable purposes, dielectric respectively to
The physics of liquid crystals property such as the opposite sex, resistivity.It is to be unable to satisfy whole use conditions with a kind of liquid-crystal compounds, it is necessary to will be several
Kind, even ten several above liquid-crystal compounds carry out compounding and form mixed liquid crystal material, can meet actually making for display device
With requiring.
TFT LCD technology requires used liquid crystal material that must have high resistivity and high voltage holding ratio, contains
The liquid-crystal compounds that fluorine atom replaces can satisfy above-mentioned requirements, be widely applied in TFT liquid crystal.To further decrease driving
Voltage shortens the response time, needs the liquid crystal material of larger dielectric anisotropy and low rotary viscosity.In addition it is also necessary to liquid
Brilliant material has the stability of height, especially after being irradiated for a long time by sunlight or backlight, still has in height
Stability.
For the photostability for improving liquid crystal material, patent US2008128653 discloses structural formula quaterphenyl as follows
Class liquid-crystal compounds improves the photostability of liquid-crystal composition:
But this kind of fluorine-containing quaterphenyl liquid-crystal compounds fusing point with higher, cause its in mixed liquid crystal dissolubility compared with
It is low, partial crystallization phenomenon is easy to produce under low temperature.
Summary of the invention
For LCD technology to liquid-crystal composition demand, the object of the present invention is to provide a kind of raising liquid crystal materials
Material environmental suitability and the quaterphenyl class liquid-crystal compounds that makes moderate progress of low temperature intermiscibility, and have wider mesophase range and
Liquid-crystal composition with high environmental suitability.
In order to realize that above-mentioned task, the present invention take following technical solution:
A kind of quaterphenyl class liquid-crystal compounds, it is characterized in that structure such as general formula such as (1) is shown:
Wherein R is straight chained alkyl, alkenyl, the alkoxy of carbon number 1~9；L1~L4It is former for methyl, chlorine atom, fluorine atom or hydrogen
Son, and L1~L4Wherein at least one is methyl or chlorine atom.
A kind of liquid-crystal composition, it is characterized in that the first component structure general formula is such as shown in (1), mass ratio is 0.5~
30%.
Present composition formula of (1) liquid-crystal compounds, preferably is selected from flowering structure:
Wherein R is preferably the straight chained alkyl of carbon number 1~7.
The first component ratio of composition of the invention is 0.5%~30%wt, preferably 1%-20%wt, more preferable 2%-
15%wt.
Composition of the invention includes that at least one is selected from liquid-crystal compounds shown in general structure (2) as second group
Point:
Wherein R1, R2For straight chained alkyl, alkoxy, alkenyl or alkyl, F, Cl containing ethylene linkage, ring A, ring B, ring C are benzene
Ring or hexamethylene, wherein phenyl ring can be replaced by one or more fluorine atoms, n=0, and 1.Second component ratio of the invention is 0-
80%, preferably 10%-75%, more preferable 20%~70%wt.
The preferred specific structure of its formula of (2) is as follows:
Wherein (2) -1 more preferably with flowering structure:
Wherein (2) -2 more preferable compounds in detail below:
Wherein (2) -3 more preferable compounds in detail below:
Wherein (2) -4 more preferable compounds in detail below:
Wherein (2) -5 more preferable compounds in detail below:
Liquid-crystal composition of the present invention includes that at least one is selected from liquid-crystal compounds shown in general structure (3) as third group
Point:
Wherein R be straight chained alkyl, alkenyl or the alkyl containing ethylene linkage, ring A, ring B, ring C be phenyl ring or hexamethylene, wherein
Phenyl ring can be replaced by one or more fluorine atoms；X1, X2=H, F；Y=F, Cl, OCF3, OCF2H, straight chained alkyl or contains ethylene linkage
Alkyl etc.；Z=CF2O, CH2CH2, COO, singly-bound etc.；N=0,1.Third component ratio of the present invention be 0-50%, preferably 5%~
45%wt, more preferable 10%-40%.Its formula of (3) preferably structure in detail below:
Wherein 3- (1) preferred compound:
Wherein 3- (2) preferred compound:
Wherein 3- (3) preferred compound:
Wherein 3- (4) preferred compound:
Wherein 3- (5) preferred compound:
Wherein 3- (6) preferred compound:
Wherein 3- (7) preferred compound:
Wherein 3- (8) preferred compound:
Wherein 3- (9) preferred compound:
Wherein 3- (10) preferred compound:
Wherein 3- (11) preferred compound:
Wherein 3- (12) preferred compound:
Wherein 3- (13) preferred compound:
Wherein 3- (14) preferred compound:
Wherein 3- (15) preferred compound:
Wherein 3- (16) preferred compound:
Liquid-crystal composition of the present invention also may include one or more chiral additives, content 0.01%-1%；It is preferred that
0.1%-0.5%.The chiral additives preferably are selected from flowering structure:
Liquid-crystal composition of the present invention also includes one kind of multiple hindered phenols as antioxidative stabilizer, content 1ppm-
10000ppm；It is preferred that 10ppm-1000ppm.The antioxidative stabilizer preferably is selected from flowering structure:
Liquid-crystal composition of the present invention also includes one or more light stabilizers, content 1ppm-10000ppm；It is preferred that 10ppm-
1000ppm.The light stabilizer preferably is selected from flowering structure:
The present invention also may include one or more liquid crystal components with polymerizable groups, content 1ppm-10000ppm；It is excellent
Select 100ppm-1000ppm.The polymerisable liquid crystal component preferably is selected from flowering structure:
Advantages of the present invention: quaterphenyl class liquid-crystal compounds of the invention has conjugation quaterphenyl structure, has to ultraviolet light
There is higher absorbability, the photostability of liquid crystal material can be promoted；The biggish methyl of volume or chlorine atom are introduced as side
To substituent group, the intermolecular active force of quaterphenyl stiffening ring is weakened, therefore fusing point is big compared with known quaterphenyl liquid-crystal compounds
Width reduces, and significantly improves in the dissolubility mixed in liquid crystal；Meanwhile such compound also have compared with high birefringence rate, compared with
The advantages of big dielectric constant.Liquid-crystal composition of the invention, photostability with higher, biggish dielectric anisotropy, compared with
Fast response speed is suitable for the display patterns such as TFT LCD technology, especially TN, IPS, FFS.
Specific embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.
Dispensing liquid crystal preparation method: heat of solution method is used.The monomer of different weight ratio is weighed with precision balance first
Liquid crystal is heated to 60 DEG C~100 DEG C, and being stirred 1~2 hour is uniformly dissolved each component.It is filtered after cooling, filters institute
Liquid is obtained in high vacuum (≤100Pa) degassing process, is finally encapsulated with high pure nitrogen, obtains target mixed liquid crystal.
Unless otherwise specified, liquid-crystal composition of the present invention is prepared in this way.
The liquid crystal mixed carries out physical property and photoelectric properties test.The present invention relates to physical property and photo electric
Energy detailed test method is as follows:
(1) clearing point (Tni):
Polarisation thermal station method: liquid crystalline sample being coated on glass slide and is placed in cross-polarized light microscopic heating stand, setting heating speed
Rate is 2 DEG C/min.The temperature of liquid crystalline sample blackening by illuminated state, as clearing point are observed in petrographic microscope.
Or use differential scanning calorimetry: under nitrogen atmosphere, setting heating rate is 2 DEG C/min.
(2) low temperature storage temperature (LTS): the mixed liquid crystal of 1mL or so is fitted into transparent vial, is placed in Low-temperature Ice
In case.- 20 DEG C of temperature setting, -30 DEG C, -40 DEG C store 10 days respectively, and observation is precipitated whether there is or not crystal or smectic phase.If -30
DEG C without crystal be precipitated, LTS≤- 30 DEG C.
(3) (Δ n): using abbe's refractometer to birefringence, under 25 DEG C of constant temperatures, measures ordinary light (n respectivelyo) and it is non-
Ordinary light (ne) refractive index, birefringence Δ n=ne- no。
(4) it under dielectric constant (Δ ε): 25 DEG C of constant temperatures, is tested using LCR table.Δ ε=ε∥-ε⊥, i.e. molecular long axis side
To dielectric constant (ε∥) and molecular short-axis direction dielectric constant (ε⊥) difference.
(5) elastic constant (K11, K33): under 25 DEG C of constant temperatures, by testing liquid crystal capacitance-voltage (C-V) curve, intend
Conjunction obtains K11And K33。
(6) rotary viscosity (γ1): under 25 DEG C of constant temperatures, by applying voltage to liquid crystal test box, test liquid crystal molecule
With the transient current value Ip of electric field movement deflection, rotary viscosity γ is calculated1。
Code name and explanation:
(1) physical parameter
| Code name | Explanation | Unit |
| Tni | Clearing point | ℃ |
| TCN | Low temperature storage temperature | ℃ |
| Δε | Dielectric anisotropy constant | |
| Δn | Birefringence | |
| γ1 | Rotary viscosity | mPa·s |
| K11 | Splay elastic constant | pN |
| K33 | Bend elastic constant | pN |
(2) structure is abridged
Such as:
Embodiment 1:
3,4,5- tri- fluoro- 2 "-methyl -4 " '-amyl -1,1':4', the synthesis of 1 ": 4 ", 1 " '-quaterphenyl
Specific structure is as follows:
Preparation process is as follows:
The synthesis of bromo- 3- methyl -4'- amyl -1, the 1'- biphenyl of step 1:4-
Under nitrogen protection, burnt to tri- mouthfuls of round bottoms of 1L equipped with mechanical stirring, reflux condensing tube, thermometer, nitrogen gas-guide tube
The bromo- 5- iodotoluene (59.4g, 0.2mol) of 4- amyl phenyl boric acid (38.4g, 0.2mol), 2-, Anhydrous potassium carbonate are sequentially added in bottle
(82.8g, 0.6mol), tetrabutylammonium bromide (6.4g, 0.02mol), toluene (200mL), ethyl alcohol (200mL), water (200mL),
Bis- (triphenylphosphine) palladium chlorides (2.1g, 3mmol) are eventually adding, nitrogen is replaced three times.Heating is opened, system rises to interior temperature 60
DEG C, 4~6h of insulation reaction stops reaction.It is down to room temperature, stratification, water phase is extracted with toluene, is incorporated into organic phase, is washed
To neutrality, anhydrous magnesium sulfate is dry, filters, is spin-dried for obtaining rufous oily liquids.Crude product carries out high vacuum distillation, obtains colorless oil
Shape liquid product 35g, G/C content 96.6%, yield 55.2%.
Step 2:3,4,5- tri- fluoro- 2 "-methyl -4 " '-amyl -1,1':4', the synthesis of 1 ": 4 ", 1 " '-quaterphenyl
Under nitrogen protection, bromo- 3- methyl -4'- amyl -1, the 1'- biphenyl of 4- is sequentially added in 250mL single necked round bottom flask
(10g, 0.03mol), 3,4,5- trifluoro-biphenyl boric acid (7.6g, 0.03mol), Anhydrous potassium carbonate (12.4g, 0.09mol), four fourths
Base amine bromide (0.97g, 0.003mol), toluene (60mL), ethyl alcohol (60mL), water (60mL), is eventually adding bis- (triphenylphosphines)
Palladium chloride (0.32g, 0.45mmol), nitrogen are replaced three times, and heating is opened, and back flow reaction 5h stops reaction.Room temperature is down to,
Stratification, water phase are extracted with toluene, are incorporated into organic phase, are washed to neutrality, and anhydrous magnesium sulfate is dry, filters, is spin-dried for slightly
Product.Crude product is eluted with V (normal heptane)/V (toluene)=10/1, carries out column chromatography for separation purification, collects eluent, and concentration is done molten
Agent is recrystallized to give white crystal product 5.8g, G/C content 99.8%, yield 43.5% with normal heptane.
Structural Identification data:1H NMR (δ, CDCl3): 7.577~7.552 (m, 4H), 7.522 (s, 1H), 7.501~
7.482 (m, 1H), 7.470~7.454 (m, 2H), 7.329~7.313 (d, 1H, J=8Hz), 7.285~7.245 (m, 4H),
2.679~2.647 (t, 2H, J=8Hz), 2.382 (s, 3H), 1.705~1.645 (m, 2H), 1.396~1.341 (m, 4H),
0.935~0.908 (t, 3H, J=7Hz)；MS (70eV) m/z (%): 444.5 (M+, 71.06), 387.4 (100), 371.3
(8.44)。
The above Structural Identification is statistics indicate that synthesized compound out is strictly the fluoro- 2 "-methyl-of compound 3,4,5- tri-
4 " '-amyls -1,1':4', 1 ": 4 ", 1 " '-quaterphenyl.
The phase transition temperature of the compound is tested with the condition heating of 5 DEG C/min with DSC, as a result are as follows: C 82.78N
128.52I。
Embodiment 2:
2 "-chloro- 3,4,5- tri- fluoro- 4 " '-propyl -1,1':4', the synthesis of 1 ": 4 ", 1 " '-quaterphenyl
Specific structure is as follows:
Preparation process is as follows:
(1) synthesis of chloro- 4'- propyl -1, the 1'- biphenyl of the bromo- 3- of 4-
Under nitrogen protection, burnt to tri- mouthfuls of round bottoms of 1L equipped with mechanical stirring, reflux condensing tube, thermometer, nitrogen gas-guide tube
The chloro- 4- bromo-iodobenzene (54g, 0.17mol) of 4- propyl phenyl boric acid (27.9g, 0.17mol), 3-, Anhydrous potassium carbonate are sequentially added in bottle
(70.4g, 0.51mol), tetrabutylammonium bromide (5.5g, 0.017mol), toluene (180mL), ethyl alcohol (180mL), water
(180mL), is eventually adding bis- (triphenylphosphine) palladium chlorides (1.2g, 1.7mmol), and nitrogen is replaced three times.Open heating, reflux
4~6h is reacted, reaction is stopped.It is down to room temperature, stratification, water phase is extracted with toluene, is incorporated into organic phase, it is washed to neutrality,
Anhydrous magnesium sulfate is dry, filters, is spin-dried for obtaining crude product.Crude product is dissolved with normal heptane, crosses silicagel column, and elution is collected in normal heptane elution
Liquid is spin-dried for, and obtains shallow orange solid product 43g, G/C content 97.4%, yield 81.7% with ethyl alcohol recrystallization.
(2) synthesis of (the chloro- 4'- propyl-of 3- [1,1'- biphenyl] -4- base) boric acid
Under nitrogen protection, to equipped with mechanical stirring, thermometer, constant pressure funnel, nitrogen gas-guide tube tri- mouthfuls of circles of 500mL
Chloro- 4'- propyl -1, the 1'- biphenyl (43g, 0.139mol) of the bromo- 3- of 4-, dry THF (150mL) are added in the flask of bottom, stirs molten
Solution completely, with liquid nitrogen cooling to -78 DEG C, starts that n-BuLi (hexane solution of 0.167mol, 70mL, 2.4M) is added dropwise, drop
THF (50mL) solution of the triisopropyl borate ester (31.4g, 0.167mol) freezed in advance, drop is added dropwise in insulation reaction 1h after complete
Complete subsequent continuous insulation reaction 1h, rises again naturally, and 10% dilute hydrochloric acid solution is added into reaction system, stirs 0.5h, stands and divides
Liquid separates organic phase, is washed to neutrality, is concentrated under reduced pressure and does, is recrystallized to give white crystal product 29.3g, yield with petroleum ether
76.8%.
(3) 2 "-chloro- 3,4,5- tri- fluoro- 4 " '-propyl -1,1':4', the synthesis of 1 ": 4 ", 1 " '-quaterphenyl
Under nitrogen protection, (3- chloro- 4'- propyl-[1,1'- biphenyl] -4- is sequentially added in 250mL single necked round bottom flask
Base) boric acid (3.5g, 0.0126mol), 4'- bromo- 3,4,5- tri- fluoro- 1,1'- biphenyl (3.44g, 0.012mol), Anhydrous potassium carbonate
(5g, 0.036mol), tetrabutylammonium bromide (0.39g, 1.2mmol), toluene (35mL), ethyl alcohol (35mL), water (35mL), finally
Bis- (triphenylphosphine) palladium chlorides (0.13g, 0.18mmol) are added, nitrogen is replaced three times.Heating is opened, back flow reaction 6h stops
Only heat.It is down to room temperature, stratification, water phase is extracted with toluene, is incorporated into organic phase, is washed to neutrality, and anhydrous magnesium sulfate is dry
It is dry, it filters, is spin-dried for obtaining crude product.Crude product V(normal heptane)/V(toluene)=5/1 elution, carries out column chromatographic purifying, collects eluent, is spin-dried for,
White crystal product 3g, G/C content 99.6%, yield 57.2% are recrystallized to give with the mixed solvent of toluene and ethyl alcohol.
Structural Identification data:1H NMR (δ, CDCl3): 7.723~7.720 (m, 1H), 7.583~7.530 (m, 7H),
7.426~7.410 (d, 1H, J=8Hz), 7.293~7.239 (m, 4H), 2.664~2.633 (t, 2H, J=7.5Hz),
1.732~1.657 (m, 2H), 0.999~0.970 (t, 3H, J=7.5Hz).
MS (70eV) m/z (%): 438.2 (28.8), 437.3 (24.61), 436.2 (M+, 78.93), 409.2
(34.45), 408.2 (26.87), 407.2 (100), 371.2 (13.52), 203.5 (36.14).
The above Structural Identification is statistics indicate that synthesized compound out is strictly compound 2 "-chloro- 3,4,5- tri- fluoro- 4 " '-
Propyl -1,1':4', 1 ": 4 ", 1 " '-quaterphenyl.The phase transition temperature of the compound is tested with the condition heating of 5 DEG C/min with DSC,
As a result are as follows: C 99.24N 126.62I.
Embodiment 3:
2 "-chloro- 2', 3,4,5- tetra- fluoro- 4 " '-propyl -1,1':4', the synthesis of 1 ": 4 ", 1 " '-quaterphenyl
Specific structure is as follows:
Using bromo- 2,3', the 4' of 4-, fluoro- 1, the 1'- biphenyl of 5'- tetra- replaces the 4'- bromo- 3,4,5- in 1 step of embodiment (3)
Three fluoro- 1,1'- biphenyl can synthesize the chloro- 2' of target compound 2 "-, 3,4,5- tetra- fluoro- 4 " '-propyl-according to same method
1,
1':4', 1 ": 4 ", 1 " '-quaterphenyl.
Structural Identification data:1H NMR (δ, CDCl3): 7.726~7.723 (m, 1H), 7.568~7.528 (m, 3H),
7.467~7.403 (m, 2H), 7.375~7.324 (m, 2H), 7.297~7.241 (m, 4H), 2.666~2.635 (t, 2H, J
=7.5Hz), 1.733~1.658 (m, 2H), 0.999~0.970 (t, 3H, J=7Hz).
MS (70eV) m/z (%): 456.2 (26.9), 455.3 (22.65), 454.3 (M+, 75.14), 427.2
(35.83), 426.2 (28.87), 425.2 (100), 389.2 (15.31), 212.6 (43.45).
For the above Structural Identification statistics indicate that synthesized compound out is strictly the chloro- 2' of compound 2 "-, 3,4,5- tetra- is fluoro-
4 " '-propyl -1,1':4', 1 ": 4 ", 1 " '-quaterphenyl.
The phase transition temperature of the compound is tested with the condition heating of 5 DEG C/min with DSC, as a result are as follows: C 90.62N
101.83I。
Composition embodiment 1:
Composition embodiment 2:
Composition embodiment 3:
Composition embodiment 4:
Composition has larger dielectric anisotropy and extremely low rotary viscosity and higher stability in above embodiments, fits
Together in displays applications such as TN type, IPS type, FFS.
Comparative example 1:
Patent US2008128653 discloses structural formula quaterphenyl class liquid-crystal compounds as follows:
The liquid-crystal phase-transition temperature and solubility of the compound see the table below with the compounds of this invention comparison:
Wherein dissolubility test is to be added to every kind of compound in basic components by a certain percentage, is placed at room temperature
120hr has seen whether crystal precipitation phenomenon.Basic components are made of three kinds of monomer liquid crystals (2CCGF, 3CCGF, 5CCGF),
Mass ratio is 2CCGF:3CCGF:5CCGF=1:1:1.
As can be seen from the table, not only fusing point reaches 111 DEG C to tetrad benzene compound in comparative example, but also presence is wider
Smectic phase；Quaterphenyl melting point compound of the present invention is below 100 DEG C, and only shows nematic phase；Dissolubility test can be seen
Out, the compounds of this invention dissolubility substantially improves.
Comparative example 2:
Implement 1 identical monomer composition with composition, but does not include tetrad benzene compound 3PP of the invention wherein1PUF and
5PP1PUF。
The liquid-crystal composition of comparative example 2 and composition embodiment 1 is poured into the TN testing cassete that box thickness is 5 μm respectively
In, with 365nm ultraviolet light (energy density 100mw/cm2) 60min is irradiated, test voltage conservation rate (VHR) is as a result seen below
Table:
| Composition | VHR(60℃,16.67ms) |
| Composition embodiment 1 | 97.1% |
| Comparative example 2 | 95.7% |
As can be seen from the table, the composition VHR value with higher of quaterphenyl liquid-crystal compounds of the present invention, this table are added
Such bright compound has the function of being obviously improved photostability.
Claims (5)
1. a kind of quaterphenyl class liquid-crystal compounds, structure feature is general structure such as shown in (1):
Wherein R is straight chained alkyl, alkenyl, the alkoxy of carbon number 1~9；X1~X4For methyl, chlorine atom, fluorine atom or hydrogen atom,
And X1~X4One of them is methyl or chlorine atom.
2. a kind of nematic phase liquid crystal composition, which is characterized in that the composition includes general structure LCD compound as shown in (1)
For object as the first component, mass ratio is 0.5~30%.
3. a kind of liquid-crystal composition according to claim 2, which is characterized in that the composition includes 0~80% structure
General formula liquid-crystal compounds as shown in (2) is as the second component:
Wherein R1, R2Respectively straight chained alkyl, alkoxy, alkenyl or alkyl, F or Cl containing ethylene linkage, ring A, ring B, ring C are
Phenyl ring or hexamethylene, wherein phenyl ring can be replaced by one or more fluorine atoms, n=0 or 1.
4. a kind of liquid-crystal composition according to claim 3, which is characterized in that the composition includes 0~50% structure
General formula liquid-crystal compounds as shown in (3) is as third component:
Wherein R is straight chained alkyl, alkenyl or the alkyl containing ethylene linkage, and ring A, ring B, ring C are phenyl ring or hexamethylene, wherein phenyl ring
It can be replaced by one or more fluorine atoms；X1, X2=H or F；Y=F, Cl, OCF3, OCF2H, straight chained alkyl or contain
The alkyl etc. of ethylene linkage；Z=CF2O, CH2CH2, COO or singly-bound etc.；N=0 or 1.
5. a kind of liquid crystal display element with high environmental suitability, it is characterised in that include liquid crystal described in claim 1-4
Composition or compound.
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Cited By (4)
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|---|---|---|---|---|
| CN110746981A (en) * | 2019-10-31 | 2020-02-04 | 武汉轻工大学 | Liquid crystal composition and application thereof |
| CN110760311A (en) * | 2019-10-31 | 2020-02-07 | 武汉轻工大学 | Lateral methyl poly-biphenyl liquid crystal compound, liquid crystal composition and application thereof |
| CN110776396A (en) * | 2019-10-31 | 2020-02-11 | 武汉轻工大学 | Side ethyl quaterphenyl liquid crystal compound, preparation method thereof, liquid crystal composition and microwave device |
| CN114262614A (en) * | 2021-12-27 | 2022-04-01 | 苏州汉朗光电有限公司 | Positive liquid crystal composition and application |
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| CN110776396B (en) * | 2019-10-31 | 2022-09-09 | 武汉轻工大学 | Side ethyl quaterphenyl liquid crystal compound, preparation method thereof, liquid crystal composition and microwave device |
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