CN109825307A - A kind of low melting point, high Jie's low consumption liquid-crystal composition and comprising high frequency assembly - Google Patents
A kind of low melting point, high Jie's low consumption liquid-crystal composition and comprising high frequency assembly Download PDFInfo
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Abstract
A kind of liquid-crystal composition of the present invention and the high frequency assembly comprising it, liquid-crystal composition include the first component and the second component, and the first component includes one of compound shown in formula I or a variety of, and the second component includes one of formula II and formula III or a variety of；
Description
Technical field
The invention belongs to liquid crystal material technical fields, and in particular to a kind of liquid-crystal composition and the high frequency assembly comprising it.
Background technique
The liquid crystal that microwave device uses can realize phase adjusted under high frequency condition, and research starts from the end of the 20th century, high speed
It is developed in the beginning of this century；Global extensive concern had especially been obtained in recent years, and German Darmstadt university is in this field
Research be in it is advanced in the world, tunable filter, reconfigurable antenna, adjustable frequency selector and adjustable shifting are covered in research work
The key areas such as phase device, Lim K.C. in 1993 et al. use commercial liquid crystals K15, and according to electro-optic birefringent effect, it is inclined to apply 16V
Voltage obtains 20 ° of phase shift in 10.5GHz frequency, realizes that microwave phase is adjustable, and Germany reports a kind of plane within 2002
Integrated liquid crystal tunable phase shifter, obtains 53 ° near 18GHz frequency of phase shift, by world's colleague's most attention, France in 2004
Rectangular patch antenna is developed using liquid crystal BL037, obtains the frequency of 140MHz between 4.74~4.6GHz by applying bias-voltage
It moves, Frequency Adjustable amount reaches 5.5%, and Spain in 2013 develops tri- dipoles of 53*54 of working frequency 96GHz~104GHz
Unit reflective array column paster antenna, realizes 165 ° of phase change, and Germany developed the deflection of adjustable two dimension wave beam in 2015
LCD phased array column brush patch antenna, realizes that 300 ° of amount of phase shift of 17.5GHz frequency range, variable bias 15V, return loss are lower than 15dB.
Report the message that Kymeta company, the U.S. develops LCD phased array antenna prototype on September 20th, 2017 " space flight news ", it is quasi-
It is standby to load transmitting-receiving satellite communication system traffic information and access internet etc. on aircarrier aircraft and automobile, it is seen then that microwave liquid crystal moves
Phase device research and development is rapid.
Nevertheless, but in related key technical, such as liquid crystal material, orientation, encapsulation, wiring, device design and menu
Sign etc. is many-sided all to have basic problem anxious to be resolved, and the research report especially in terms of liquid crystal material is less；It is most German
Merck Products have been developed that a variety of optical anisotropies i.e. birefringence be greater than 0.3 liquid crystal material, but so far without
Method solves the problems, such as that dielectric loss is big；Herman J. et al. reported the lateral second of isothiocyano-at 2013 and 2015 respectively
Four benzene diethyl alkynes liquid crystal compounds of base (i.e. birefringence is greater than >=0.6), microwave phase-shift phase obviously increases, but dielectric loss is inclined
Greatly, material melting point is high, takes into account that birefringence is high, microwave phase-shift phase is obvious but dielectric loss is small, low-melting material so far
It reports less.
In addition, be difficult to find in existing liquid crystal material ReuterM. in 2013 et al. report the p- F of high frequency ,-CN ,-
The influence of the different end groups such as NCS suction wave；It is NCS, CN, F, OCF that Dziaduszek J in 2017 et al., which reports end group,3Deng lateral
The △ n=0.45 liquid crystal material that fluorodiphenyl acetylene class series compound is prepared, analysis compare these end groups to GHz and THz
The influence of wave band dielectric anisotropy, Kowerdziej R. in 2018 et al. report fluorine-containing tolans isothiocyanic acid
Ester liquid crystal composition finds that this kind of liquid crystal can to microwave phase in the optic tunable variation with temperature situation of 6GHz frequency range
Arranging property (τ) and dielectric properties vary with temperature unobvious, show that the structural units such as isothiocyano and acetenyl compare microwave
Stablize, nearest Lapanik V. et al. is mixed on the basis of Kowerdziej R. works using the more aromatic ring classes of isothiocyano-
Dielectric loss is not only reduced to 0.003 by liquid crystal material, also increases microwave amount of phase shift, and the humorous coefficient of phase-adjustable (τ) increases
To 0.34, the stability of group in molecular structure, bridged bond is disclosed to the influence of dielectric loss, but its material melting point still exists
0 DEG C or more, it is not also able to satisfy the requirement of outdoor limit low temperature condition, and so far to the low temperature photoelectricity of microwave liquid crystal
There is not been reported for the research of performance influence aspect.
Summary of the invention
In order to solve the above technical problems, the present invention provides a kind of low-melting point liquid crystal composition and the high frequency assembly comprising it.
Specific technical solution is as follows:
A kind of liquid-crystal composition, the difference is that, the liquid-crystal composition includes the first component and the second component, institute
Stating the first component includes one of compound shown in formula I or a variety of, and second component includes one of formula II and formula III
Or it is a variety of, first component accounts for the 1%~30% of the liquid-crystal composition gross mass；
Wherein, R1With R2Respectively indicate alone H, 2~7 carbon atoms containing 1~2 fluorine alkyl, contain methyl substituents
The alkyl of 2~7 carbon atoms contains alkenylalkyl, X1、X2、 X3And X4H, F or Cl are respectively indicated alone；
Wherein, R3With R4The straight chained alkyl containing 2~7 carbon atoms, Y are respectively indicated alone1Indicate methyl or F atom, Y2Table
Show H or F；
Wherein, R5With R6The alkyl chain containing 2~7 carbon atoms, Y are respectively indicated alone3With Y4H or F, Y are respectively indicated alone5
Indicate H or F.
In above-mentioned technical proposal, the liquid-crystal composition further includes third component, and the third component is as shown in formula IV:
Wherein, Z1Be represented as singly-bound orR7Represent the alkyl chain containing 2~7 carbon atoms, Y6Represent H or
F, Y7Represent F,R8Represent the alkyl chain containing 2~7 carbon atoms.
In above-mentioned technical proposal, compound shown in the formula I is by one of chemical compounds I -1~I -11 or a variety of forms:
Wherein, R1With R2Respectively indicate alone H, 2~7 carbon atoms containing 1~2 fluorine alkyl, contain methyl substituents
The alkyl of 2~7 carbon atoms contains alkenylalkyl.
In above-mentioned technical proposal, compound shown in the formula II is by one of compound ii -1~II -3 or a variety of groups
At:
Wherein, R3With R4The straight chained alkyl containing 2~7 carbon atoms is respectively indicated alone.
In above-mentioned technical proposal, compound shown in the formula III is by one of compound III -1~III -4 or a variety of groups
At:
Wherein, R5With R6The alkyl chain containing 2~7 carbon atoms is respectively indicated alone.
In above-mentioned technical proposal, compound shown in the formula IV is by one of compounds Ⅳ -1~IV -4 or a variety of groups
At:
Wherein, R7Represent the alkyl chain containing 2~7 carbon atoms, R8Represent the alkyl chain containing 2~7 carbon atoms.
In above-mentioned technical proposal, 4 kinds~14 kinds of compound shown in the second component compound as shown in formula II or formula III
Composition, the content of each compound in the composition account for 3%~24%.
In above-mentioned technical proposal, 4~8 kinds in compound shown in selecting type II, each compound is in the composition
Content 3%~16% obtains composition M1；
Then 4~6 kinds of compound in compound shown in selecting type III, it is hybridly prepared into composition M2, each compound
Content in the composition accounts for 3%~16%；
Composition M1 and composition M2 are finally configured to the second component in proportion, it will be in the second component and the first component
2~5 kinds of progress mixed preparings obtain liquid-crystal composition, the composition M1 and composition M2 content in the second component
It is not simultaneously zero.
In above-mentioned technical proposal, the liquid-crystal composition is by following combination:
Compound shown in formula I, compound shown in compound and formula III shown in formula II；
Or
Compound shown in compound shown in formula I and formula III；
Or
Compound shown in formula I, compound and formula IV shown in compound, formula III shown in formula II
Shown compound；
Or
Compound shown in formula I, compound shown in compound and formula IV shown in formula II.
Each component compound in the liquid-crystal composition is the compound after the purification of electric field absorption method.
High frequency assembly containing above-mentioned liquid-crystal composition.
Compared with prior art, the beneficial effects of the present invention are (1) to be hybridly prepared into anisotropy i.e. birefringence value
The liquid-crystal composition material in 0.35~0.40 range, improves microwave phase modulation amount, reduces the dielectric damage of microwave device
Consumption；(2) low-melting point liquid crystal component is used, the job requirement of limit low temperature outside microwave device room is met, keeps its total freezing point minimum
It can reach -40 DEG C, microwave device open air low-temperature working is advantageous to solving.
Specific embodiment
Technical solution of the present invention is explained in detail below with reference to embodiment.
Every detection parameters is as follows in embodiment:
Δ ε indicates dielectric anisotropy；
△ n is optical anisotropy, that is, birefringence (589nm, 25 DEG C)；It Iso. is the limpid of the phase of liquid-crystal composition
Point temperature (DEG C)；
Dielectric anisotropy in microwave range is defined as:
Δεr=(εr,||-εr,⊥)；Component " the ε of parallel liquid crystal long axisr∥", the long axis component " ε of vertical liquid crystalr⊥”
Tunability (τ) is defined as: τ=(Δ εr/εr,||)。
Material quality (η) is defined as: η ≡ (τ/tan δ εr,max.),
Wherein maximum dielectric is lost are as follows: tan δ εr,max.≡max.{tanδεr,⊥；tanδεr,||}。
" birefringence " described in term: liquid-crystal compounds and the anisotropic expression of mixed liquid crystal materials optical refer to
After light passes through liquid crystal material, by liquid crystalline refractive and scattering, ordinary light and extraordinary ray are formed, ordinary refraction index indicates "
no", extraordinary ray refractive index indicates " ne", birefringence is indicated with " Δ n ", " Δ n=no-ne", microwave high-frequency requirement on devices Δ
Value >=0.30 n or more, the Δ n value the high more is conducive to improve microwave amount of phase shift.
" microwave liquid crystal " described in term: microwave phase shifter Nematic phase liquid crystal material can realize phase under high frequency condition
Position is adjusted；
The wave frequency that " dielectric loss " described in term refers to that microwave (4~40GHz) irradiation or across liquid crystal material when generate is inhaled
The loss of microwave wave frequency caused by receipts, is usually microwave Insertion Loss；
" dielectric constant " Δ ε described in termr, dielectric constant is divided into the component " ε of parallel liquid crystal long axisr∥ ' " and vertical component
“εr⊥' ", dielectric constant values are Δ ε r=εr∥-εr⊥；It is to the quantitative expression of microwave " dielectric loss " physically: dielectric loss
Tangent value (tan δ εr⊥Or tan δ ε rrmax), it is main performance index parameter of the reflecting liquid crystal material in microwave field, generally wants
Seek tan δ εr⊥(or tan δ εrrmax) value≤0.03 or so, tan δ εr//≤ 0.005 or so.
" high Jie's low consumption " liquid crystal material described in term: refer to high dielectric anisotropy, high optical anisotropy, low dielectric damage
The liquid crystal material of consumption；Microwave is after liquid crystal material irradiation, dielectric loss very little, tan δ εr⊥(or tan δ ε rmax) value is lower than
0.015 or so, tan δ εr‖'Value is lower than 0.004.
" phase modulation coefficient " described in term, is expressed as " τ ", phase-modulation ability of the reflecting liquid crystal material to microwave frequency
Parameter, 0.15≤τ≤0.5, τ (=Δ εr/εr,||)；
" quality factor " described in term (η or FOM) refers to the microwave dielectric properties overall merit knot later by liquid crystal
Fruit reflects the performance and quality of liquid crystal material, generally requires η >=15 or more, η=(τ/tan δ εr,max)。
For convenient for expressing, in following embodiment, bloc framework code listed by table 1 of liquid-crystal composition is indicated:
The group structure code of 1 liquid-crystal compounds of table
Arabic numerals shown in compound code are alkyl chain carbon atomicity.
Embodiment one
General formula compound preparation route is as follows:
The synthetic method (preparation step) is as follows:
(1) step 1: under inert gas shielding, the fluoro- 4- alkyl phenyl boric acid of 2-, 2- ethyl-are sequentially added into reaction flask
4- Iodoaniline, tetra-triphenylphosphine palladium, K2CO3, ethyl alcohol, toluene and water, heating stirring, reaction reflux temperature are 65 DEG C~85 DEG C；Instead
It is reacted after 4~8h with TCL detecting and tracking between seasonable, after reacting completion, stops stirring, carried out purification processes and obtain solid
Intermediate (b)；
(2) step 2: sequentially adding intermediate (b) into three-necked flask, the concentrated sulfuric acid and tetrahydrofuran (THF), then into
NaNO is added dropwise after dropping to -5 DEG C~3 DEG C in row ice salt bath, temperature2Aqueous solution is added dropwise (anti-in the process in 0.5 hour~2 hours
Answer liquid temperature no more than 20 DEG C), after keeping the temperature 0 DEG C~8 DEG C stirring 1h, then KI aqueous solution is added dropwise, temperature controls during dropwise addition
At 0~5 DEG C or so, no more than 10 DEG C；Naturally it is warmed to room temperature reaction 1h after being added dropwise, is post-processed to obtain intermediate
(c)；
(3) step 3: under inert gas shielding, intermediate (c), 3 '-fluoro- 4 '-alkyls are sequentially added into reaction flask
Biphenylboronic acid, tetra-triphenylphosphine palladium, K2CO3, ethyl alcohol, toluene and water, heating stirring, reaction reflux temperature are 65 DEG C~80 DEG C, instead
6~8h between seasonable is reacted with TCL detecting and tracking；After fully reacting, stopping stirring, reaction solution is naturally cooling to room temperature, into
Row post-processing obtains the fluorine-containing quaterphenyl of side chain ethyl (I).
5GP (2) PP4 molecular structure identification data are as follows:
1H-NMR(CDCl3, 400MHz) and δ (ppm): 7.31~7.68 (m, 14H), 2.65~2.68 (t, 4H), 2.51~
2.54 (m, 2H), 1.68~1.82 (m, 4H), 1.45~1.49 (m, 6H), 0.99~1.26 (t, 9H)；
13C-NMR (100MHz, CDCl3) δ (ppm): 14.050,14.132,15.273,22.478,22.656,
26.490,31.267,31.663；33.665,35.390,35.690,113.73, 122.36,124.33,126.88,
127.35,128.88,129.07,130.81,132.04,133.73, 137.02,138.46,141.15,142.21,
158.84,161.28；
19F-NMR (376.29MHz, CDCl3) δ (ppm): -114.34.
5UP (2) PP4, molecular structure identification data are as follows:
1H-NMR(CDCl3, 400MHz) and δ (ppm): 7.25~7.88 (m, 13H), 2.71~2.73 (t, 2H), 2.64~
2.67 (t, 2H), 2.53~2.56 (m, 2H), 1.61~1.65 (m, 4H), 1.45~1.54 (m, 6H), 0.98~1.25 (m,
9H)；
13C-NMR (100MHz, CDCl3) δ (ppm): 14.050,14.132,15.273,22.478,22.656,
26.490,31.267,31.663；33.665,35.390,35.690,113.73, 122.36,124.33,126.88,
127.35,128.88,129.07,130.81,132.04,133.73, 137.02,138.46,141.15,142.21,
158.84,161.28；
19F-NMR (376.29MHz, CDCl3) δ (ppm): -115.45.
Embodiment two
II compounds process for production thereof of formula is documented in Zhang Sihan, Liu Keqing, Zhang Zhiyong, fluorine-containing two alkyne type liquid crystal of triphen of et al.
Compound synthesis and its property research [J] liquid crystal and display, 2015 (05): 769-776.
Fluorine-containing two alkynes liquid crystal compounds of the triphen synthesis of Zhang Sihan, Liu Keqing, Zhang Zhiyong, et al. and its property research
[J] liquid crystal and display, 2015,30 (5)
Embodiment three:
Compounds process for production thereof shown in formula III is documented in Hsu C S, Shyu K F, Chuang Y Y, et
al.Synthesis of laterally substituted bistolane liquid crystals[J]. Liquid
Crystals, 2000,27 (2): in 283-287 text.
Example IV:
Microwave liquid crystal combination is made by weight percent listed in table 2 in general formula I, general formula II and general formula III compound
Object A, and carried out performance detection.
2 liquid-crystal composition A of table formula and performance test
Embodiment five:
Microwave liquid-crystal composition B is made by weight percent listed in table 3 in general formula I and general formula III compound, and
Carried out performance detection.
3. liquid-crystal composition B of table formula and performance test
Embodiment six:
Microwave liquid crystal combination is made by weight percent listed in table 4 in formula I, formula II, formula III and IV compound of formula
Object C, and carried out performance detection.
4. liquid-crystal composition C of table formula and performance test
Embodiment seven:
Microwave liquid crystal combination is made by weight percent listed in table 5 in general formula I, general formula II and general formulae IV compound
Object D, and carried out performance detection.
5. liquid-crystal composition D of table formula and performance test
Embodiment eight:
Microwave liquid-crystal composition E is made by weight percent listed in table 6, and is carried out performance detection.
6. liquid-crystal composition E of table formula and performance test
Embodiment nine:
Microwave liquid crystal combination is made by weight percent listed in table 7 in general formula I, general formula II and general formulae IV compound
Object F, and carried out performance detection.
7. liquid-crystal composition F of table formula and performance test
Comparative example one:
Microwave liquid-crystal composition G is made by weight percent listed in table 8, and is carried out performance detection.
8. liquid-crystal composition G of table formula and performance test
It should be noted that embodiment described above is some embodiments of the present invention.For the technology of this field
For personnel, without departing from the concept of the premise of the invention, various modifications and improvements can be made, these belong to this
The protection scope of invention.
Claims (10)
1. a kind of liquid-crystal composition, which is characterized in that the liquid-crystal composition include the first component and the second component, described first
Component includes one of compound shown in formula I or a variety of, and second component includes one of formula II and formula III or a variety of,
First component accounts for the 1%~30% of the liquid-crystal composition gross mass；
Wherein, R1With R2H, the alkyl of 2~7 carbon atoms containing 1~2 fluorine, 2~7 containing methyl substituents are respectively indicated alone
The alkyl of a carbon atom contains alkenylalkyl, X1、X2、X3And X4H, F or Cl are respectively indicated alone；
Wherein, R3With R4The straight chained alkyl containing 2~7 carbon atoms, Y are respectively indicated alone1Indicate methyl or F atom, Y2Indicate H or
F；
Wherein, R5With R6The alkyl chain containing 2~7 carbon atoms, Y are respectively indicated alone3With Y4H or F, Y are respectively indicated alone5Indicate H
Or F.
2. a kind of liquid-crystal composition according to claim 1, which is characterized in that the liquid-crystal composition further includes third group
Point, the third component is as shown in formula IV:
Wherein, Z1Be represented as singly-bound orR7Represent the alkyl chain containing 2~7 carbon atoms, Y6Represent H or F, Y7
Represent F,R8Represent the alkyl chain containing 2~7 carbon atoms.
3. a kind of liquid-crystal composition according to claim 1, which is characterized in that compound shown in the formula I is by chemical compounds I -1
One of~I -11 or a variety of compositions:
Wherein, R1With R2H, the alkyl of 2~7 carbon atoms containing 1~2 fluorine, 2~7 containing methyl substituents are respectively indicated alone
The alkyl of a carbon atom contains alkenylalkyl.
4. a kind of liquid-crystal composition according to claim 1, which is characterized in that compound shown in the formula II is by compound
One of II -1~II -3 or a variety of compositions:
Wherein, R3With R4The straight chained alkyl containing 2~7 carbon atoms is respectively indicated alone.
5. a kind of liquid-crystal composition according to claim 1, which is characterized in that compound shown in the formula III is by compound
One of III -1~III -4 or a variety of compositions:
Wherein, R5With R6The alkyl chain containing 2~7 carbon atoms is respectively indicated alone.
6. a kind of liquid-crystal composition according to claim 2, which is characterized in that compound shown in the formula IV is by compound
One of IV -1~IV -4 or a variety of compositions:
Wherein, R7Represent the alkyl chain containing 2~7 carbon atoms, R8Represent the alkyl chain containing 2~7 carbon atoms.
7. according to any one of claim 4 or 5 a kind of liquid-crystal composition, which is characterized in that second component is by formula II
4 kinds~14 kinds of compound shown in shown compound or formula III compositions, the content of each compound in the composition accounts for 3%~
24%.
8. a kind of liquid-crystal composition according to claim 1, which is characterized in that 4~8 in compound shown in selecting type II
Kind, the content 3%~16% of each compound in the composition obtains composition M1；
Then 4~6 kinds of compound in compound shown in selecting type III, it is hybridly prepared into composition M2, each compound is in group
The content closed in object accounts for 3%~16%；
Composition M1 and composition M2 are finally configured to the second component in proportion, by 2~5 in the second component and the first component
Kind carries out mixed preparing, obtains liquid-crystal composition, the content in the second component is different from the composition M2 by the composition M1
When be zero.
9. according to claim 1 or a kind of any one of 2 liquid-crystal compositions, which is characterized in that the liquid-crystal composition by with
Lower combination:
Compound shown in formula I, compound shown in compound and formula III shown in formula II；
Or
Compound shown in compound shown in formula I and formula III；
Or
Compound shown in formula I, compound shown in compound and formula IV shown in compound, formula III shown in formula II；
Or
Compound shown in formula I, compound shown in compound and formula IV shown in formula II.
Each component compound in the liquid-crystal composition is the compound after the purification of electric field absorption method.
10. the high frequency assembly containing the described in any item liquid-crystal compositions of claim 1~6.
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| CN110699091A (en) * | 2019-10-31 | 2020-01-17 | 武汉轻工大学 | Liquid crystal composition with high dielectric constant and low consumption and application thereof |
| CN110746982A (en) * | 2019-10-31 | 2020-02-04 | 武汉轻工大学 | Achiral side methyl alkyl tetrabiphenyl liquid crystal compound, preparation method thereof, liquid crystal composition and microwave communication device |
| CN110746983A (en) * | 2019-10-31 | 2020-02-04 | 武汉轻工大学 | Achiral side methyl alkyl terphenyl liquid crystal compound, preparation method, liquid crystal composition and application |
| 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 |
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