CN107603640A - Liquid-crystal composition and its liquid crystal display device - Google Patents
Liquid-crystal composition and its liquid crystal display device Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 106
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 125000004432 carbon atom Chemical group C* 0.000 claims description 138
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 125000003342 alkenyl group Chemical group 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000004450 alkenylene group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 230000003287 optical effect Effects 0.000 abstract description 9
- 238000012360 testing method Methods 0.000 description 33
- 239000000758 substrate Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 0 *C(CC1)CCC1C1CCC(COC(C2)=CC=C(c3c(*)c(*)c(*)cc3)C(F)=C2F)CC1 Chemical compound *C(CC1)CCC1C1CCC(COC(C2)=CC=C(c3c(*)c(*)c(*)cc3)C(F)=C2F)CC1 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004991 fluoroalkenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- -1 hydrogen Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- Liquid Crystal Substances (AREA)
Abstract
The present invention provides a kind of liquid-crystal composition, and the liquid-crystal composition includes：The compound of at least one formula I；At least one formula II 1 and or II 2 compound；And the compound of at least one general formula III, the liquid-crystal composition has higher clearing point, relatively low viscosity, appropriate high dielectric anisotropy absolute value, suitable big optical anisotropy, wide nematic temperature range and good low-temperature stability, and present invention also offers a kind of liquid crystal display device for including the liquid-crystal composition.
Description
Technical Field
The invention relates to the field of liquid crystal display materials, in particular to a liquid crystal composition with a proper high absolute value of dielectric anisotropy, higher optical anisotropy, higher clearing point and good low-temperature intersolubility and a liquid crystal display device with a faster response speed.
Background
The liquid crystal display device is classified into: phase Change (PC), Twisted Nematic (TN), Super Twisted Nematic (STN), Electrically Controlled Birefringence (ECB), Optically Compensated Bend (OCB), in-plane switching (IPS), Vertical Alignment (VA), Fringe Field Switching (FFS), field-induced photo-reactive alignment (FPA), and the like. The classification of element-based driving methods is: passive Matrix (PM) and Active Matrix (AM). The PM is classified into a static (static), multiplex (multiplex), etc., and the AM is classified into a Thin Film Transistor (TFT), a Metal Insulator Metal (MIM), etc. TFTs are classified into amorphous silicon (amorphous silicon) and polycrystalline silicon (polysilicon). The latter is classified into a high temperature type and a low temperature type according to the manufacturing steps. The light source is classified into a reflection type using natural light, a transmission type using a backlight, and a semi-transmission type using both natural light and backlight.
The liquid crystal display element contains a liquid crystal composition having a nematic phase. The composition has suitable properties. By improving the characteristics of the composition, an AM element having good characteristics can be obtained. The correlation between the two properties is summarized in table 1 below. The properties of the composition are further described based on commercially available AM elements. The temperature range of the nematic phase is associated with the temperature range in which the element can be used. The upper limit temperature of the nematic phase is preferably about 70 ℃ or higher, and the lower limit temperature of the nematic phase is preferably about-10 ℃ or lower. The viscosity of the composition correlates to the response time of the element. In order to display a dynamic image on the device, the response time is preferably short. Ideally shorter than 1 millisecond. Therefore, it is preferable that the viscosity of the composition is small. More preferably, the viscosity is low at low temperature.
TABLE 1 Properties of the compositions and AM elements
The prior art discloses a liquid crystal display device including a liquid crystal composition having low power consumption and fast response, as in patent document CN102858918A, however, it is difficult to obtain a liquid crystal composition having both large optical anisotropy, large absolute value of dielectric anisotropy, good low temperature stability and fast response. When the liquid crystal composition having a large absolute value of dielectric anisotropy is applied to a liquid crystal display device, the threshold voltage is high, the power consumption is high, and the response speed is relatively slow. Therefore, in order to meet the increasing application demands, there is a continuing need in the art for improved liquid crystal compounds of negative dielectric anisotropy.
Disclosure of Invention
The invention aims to provide a liquid crystal composition which has a high clearing point, low viscosity, a suitably high absolute value of dielectric anisotropy, a suitably large optical anisotropy, a wide nematic phase temperature range and good low-temperature stability, and can enable a liquid crystal display device containing the liquid crystal composition to have a fast response speed and a good display effect.
It is another object of the present invention to provide a display device comprising the liquid crystal composition.
In order to accomplish the above object of the invention, the present invention provides a liquid crystal composition comprising:
at least one compound of the general formula I
At least one compound of the general formulae II-1 and/or II-2
And
at least one compound of the formula III
Wherein,
the R is1And R2Each independently represents-H, -F, a linear OR branched alkyl OR alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 12 carbon atoms, -OR1’OR2', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R1' represents an alkylene group of 1 to 12 carbon atoms or an alkenylene group of 2 to 12 carbon atoms, R2' represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms;
the R is3And R4Each independently represents-H, -F, a linear OR branched alkyl OR alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 12 carbon atoms, -OR3’OR4', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R3' represents an alkylene group of 1 to 12 carbon atoms or an alkenylene group of 2 to 12 carbon atoms, R4' represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms;
the R is5And R6Each independently represents a linear or branched, fluorinated or non-fluorinated alkyl or alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a fluorine of 2 to 12 carbon atomsSubstituted or unsubstituted fluoroalkenyl or alkenyloxy;
L1and L2Each independently represents-H, -F, -Cl, -CN or-NCS;
z is1、Z2And Z3Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；
The ringRing (C)Ring (C)And ringEach independently representOr
And a, b, c and d each independently represent 0 or 1.
In some embodiments of the invention, preferably, R is1And R2Each independently represents a linear OR branched alkyl OR alkoxy OR cycloalkyl group of 1 to 12 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 12 carbon atoms, -OR1’OR2', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R1' and R2' each independently represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms.
In some embodiments of the invention, preferably, theR1And R2Each independently represents a linear OR branched alkyl OR alkoxy group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 10 carbon atoms, -OR1’OR2', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R1Represents an alkylene group of 1 to 10 carbon atoms or an alkenylene group of 2 to 10 carbon atoms, R2' represents an alkyl group of 1 to 10 carbon atoms or an alkenyl group of 2 to 10 carbon atoms.
In some embodiments of the invention, preferably, R is1And R2Each independently represents a linear or branched alkyl or alkoxy group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl or alkenyloxy group of 2 to 10 carbon atoms.
In some embodiments of the invention, preferably, R is hydrogen3And R4Each independently represents a linear OR branched alkyl OR alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 12 carbon atoms, -OR3’OR4', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R3' represents an alkylene group of 1 to 12 carbon atoms or an alkenylene group of 2 to 12 carbon atoms, R4' represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms.
In some embodiments of the invention, preferably, R is3And R4Each independently represents a linear OR branched alkyl OR alkoxy group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 10 carbon atoms, -OR3’OR4', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R3' represents an alkylene group of 1 to 10 carbon atoms or an alkenylene group of 2 to 10 carbon atoms, R4' represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms.
In the inventionPreferably, in some embodiments, the R is3And R4Each independently represents a straight or branched, fluorinated or non-fluorinated alkyl or alkoxy group of 1 to 10 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a fluorinated or non-fluorinated alkenyl or alkenyloxy group of 2 to 10 carbon atoms.
In some embodiments of the invention, preferably, R is5And R6Each independently represents a straight or branched, fluorinated or non-fluorinated alkyl or alkoxy group of 1 to 8 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a fluorinated or non-fluorinated alkenyl or alkenyloxy group of 2 to 8 carbon atoms.
In some embodiments of the present invention, the liquid crystal composition further comprises one or more compounds selected from the group consisting of general formulas IV-1 to IV-12:
wherein,
R7and R8Each independently represents a linear OR branched alkyl OR alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 12 carbon atoms, -OR7’OR8', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R7' represents an alkylene group of 1 to 12 carbon atoms or an alkenylene group of 2 to 12 carbon atoms, R8' represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms.
In some embodiments of the invention, preferably, R7And R8Each independently represents a linear or branched alkyl or alkoxy group of 1 to 8 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkene of 2 to 8 carbon atomsRadical OR alkenyloxy, -OR7’OR8', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R7' represents an alkylene group of 1 to 10 carbon atoms or an alkenylene group of 2 to 10 carbon atoms, R8' represents an alkyl group of 1 to 10 carbon atoms or an alkenyl group of 2 to 10 carbon atoms.
In some embodiments of the invention, the compound of formula I comprises 1-50% by weight of the total liquid crystal composition; the compounds of the general formulas II-1 and/or II-2 account for 10-65% of the total weight of the liquid crystal composition; the compound of the general formula III accounts for 20-65% of the total weight of the liquid crystal composition; and one or more compounds of general formulas IV-1 to IV-12 account for 0 to 45 percent of the total weight of the liquid crystal composition.
In some embodiments of the present invention, preferably, the compound of formula i is present in an amount of 1 to 40%, more preferably 2 to 35%, more preferably 3 to 35%, more preferably 5 to 30% by weight of the total weight of the liquid crystal composition.
In some embodiments of the present invention, preferably, the compounds of formula II-1 and/or II-2 comprise 10 to 60%, more preferably 15 to 60%, even more preferably 15 to 55%, even more preferably 15 to 50% of the total weight of the liquid crystal composition.
In some embodiments of the present invention, preferably, the compound of formula iii accounts for 20 to 60%, more preferably 25 to 60%, more preferably 30 to 60%, and more preferably 35 to 60% of the total weight of the liquid crystal composition.
In some embodiments of the present invention, it is preferred that the group consisting of one or more of the compounds of formulae IV-1 to IV-12 is from 0 to 40%, more preferably from 0 to 35%, even more preferably from 0 to 30%, even more preferably from 1 to 30%, even more preferably from 5 to 25% by weight of the total weight of the liquid crystal composition.
In some embodiments of the invention, the compound of formula i is selected from the group consisting of one or more of the following structures:
in some embodiments of the present invention, it is further preferred that the compound of formula i-1 is selected from the group consisting of one or more of the following compounds:
wherein,
R11and R21Each independently represents a linear or branched alkyl or alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl or alkenyloxy group having 2 to 10 carbon atoms, wherein one or more H of the alkyl or alkoxy group and the alkenyl or alkenyloxy group may be substituted by F;
R1' represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R2' represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms. In some embodiments of the present invention, it is further preferred that the compound of formula i-2 is selected from the group consisting of one or more of the following compounds:
wherein,
R12and R22Each independently represents a linear or branched alkyl or alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy groupOne or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
R1' represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R2' represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
In some embodiments of the invention, it is still further preferred that the compound of formula I-1-1 is selected from the group consisting of one or more of the following compounds:
in some embodiments of the present invention, it is still further preferred that the compound of formula I-1-2 is selected from the group consisting of one or more of the following compounds:
wherein,
the R is2' independently represents an alkyl group of 1 to 12 carbon atoms.
In some embodiments of the invention, it is still further preferred that the compound of formula i-1-3 is selected from the group consisting of one or more of the following compounds:
wherein,
the R is2' independently represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms;
the R is2Independently represents an alkyl or alkoxy group of 1 to 12 carbon atoms.
In some embodiments of the present invention, it is still further preferred that the compound of formula I-2-1 is selected from the group consisting of one or more of the following compounds:
in some embodiments of the invention, it is still further preferred that the compound of formula i-2-2 is selected from the group consisting of one or more of the following compounds:
wherein,
the R is2' independently represents an alkyl group of 1 to 12 carbon atoms.
In some embodiments of the invention, it is still further preferred that the compound of formula i-2-3 is selected from the group consisting of one or more of the following compounds:
wherein,
the R is2' independently represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms;
the R is2Independently represents an alkyl or alkoxy group of 1 to 12 carbon atoms.
In some embodiments of the invention, R is2' is preferably an alkyl group of 1 to 10 carbon atoms or an alkenyl group of 2 to 10 carbon atoms.
The compound of the general formula I has large optical anisotropy, large absolute value of dielectric anisotropy, high clearing point, wide nematic phase temperature range and low rotational viscosity, so that a liquid crystal composition containing the compound of the general formula I has the advantages of high clearing point, large optical anisotropy, large absolute value of dielectric anisotropy, low rotational viscosity, fast response time, wide nematic phase temperature range and good low-temperature stability.
In some embodiments of the present invention, the compound of formula II-1 is preferably selected from the group consisting of one or more of the following compounds II-1-1 through II-1-20:
in some embodiments of the invention, the compound of formula II-1 is particularly preferably one or more of II-1-1, II-1-2, II-1-3, II-1-6, II-1-10, II-1-11, II-1-12, II-1-13, II-1-14 or II-1-17.
In some embodiments of the present invention, the compound of formula II-1 is preferably selected from the group consisting of one or more of the following compounds II-2-1 through II-2-27:
in some embodiments of the invention, the compound of formula II-2 is particularly preferably one or more of II-2-2, II-2-3, II-2-4, II-2-7, II-2-8, II-2-12, II-2-13, II-2-14, II-2-15, II-2-16, II-2-19, II-2-20, II-2-22 or II-2-24.
In some embodiments of the invention, the compound of formula III is selected from the group consisting of formula III-1, formula III-2, formula III-3, and combinations thereof:
wherein,
the R is51、R52、R53、R61、R62And R63Each independently represents-H, -F, alkyl or alkoxy of 1-12 carbon atoms, alkenyl or alkenyloxy of 2-12 carbon atoms,Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
z is1、Z2And Z3Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-。
In some embodiments of the invention, the compound of formula III-1 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-2 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-3 is selected from the group consisting of:
wherein,
R51、R52、R53、R61、R62and R63Each independently represents-H, -F, alkyl or alkoxy of 1-7 carbon atoms, alkenyl or alkenyloxy of 2-7 carbon atoms.
In some embodiments of the invention, the compound of formula III-1-1 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-1-2 is selected from the group consisting of:
in some embodiments of the invention, the compounds of formulas III-1-3 are selected from the group consisting of:
in some embodiments of the invention, the compounds of formulas III-1-4 are selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-2-1 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-2-2 is selected from the group consisting of:
in some implementations of the invention, the compound of formula III-2-3 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-2-4 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-2-5 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-3-1 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-3-2 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-3-3 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-3-4 is selected from the group consisting of:
in some embodiments of the invention, the compound of formula III-3-5 is selected from the group consisting of:
in some embodiments of the present invention, preferably, the liquid crystal composition is selected from the group consisting of one or more of the following compounds:
another aspect of the invention provides a liquid crystal composition further comprising one or more additives known to those skilled in the art and described in the literature. For example, pleochroic dyes and/or chiral dopants may be added in an amount of 0 to 15 wt% based on the total weight of the liquid crystal composition.
In some embodiments of the invention, the compound of formula i is preferably selected from the following compounds: i-1-1-2, I-1-1-3, I-1-1-4, I-1-1-7, I-1-1-8, I-1-1-9, I-1-1-10, I-2-1-2, I-2-1-3, I-2-1-4, I-2-1-6 and I-2-1-10.
In some embodiments of the invention, the compound of formula ii is preferably selected from the following compounds: II-1-2, II-1-10, II-1-12, II-1-13, II-1-14, II-2-2, II-2-4, II-2-10, II-2-13, II-2-14 and II-2-15.
In some embodiments of the invention, the compound of formula iii is preferably selected from the following compounds: III-1-3-4, III-1-3-33, III-1-3-37, III-1-1-15, III-1-1-17, III-1-1-19, III-1-2-2, III-2-1-4, III-2-1-8 and III-3-1-5.
In some embodiments of the invention, the compound of formula IV is preferably selected from the following compounds: IV-6 and IV-7.
The following shows possible dopants which are preferably added to the mixtures according to the invention.
In the embodiment of the present invention, it is preferable that the dopant is 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the dopant is present in an amount of 0 to 1 wt% based on the total weight of the liquid crystal composition.
The stabilizers which may be added to the mixtures according to the invention are mentioned below, for example.
Preferably, the stabilizer is selected from the group consisting of the stabilizers shown below.
Wherein n is a positive integer of 1-20.
In the embodiment of the present invention, it is preferable that the stabilizer accounts for 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the stabilizer accounts for 0-1 wt% of the total weight of the liquid crystal composition; as a particularly preferred embodiment, the stabilizer is 0 to 0.1 wt% of the total weight of the liquid crystal composition.
In another aspect, the present invention also provides a liquid crystal display device comprising the above liquid crystal composition.
The terphenyl negative liquid crystal compound containing the general formula I and the cyclohexyl negative liquid crystal compound containing the general formula II-1 and/or the general formula II-2 are used in combination, so that the liquid crystal composition has a high clearing point, a large absolute value of dielectric anisotropy, a low viscosity, a wide nematic phase temperature range and good low-temperature stability, and a liquid crystal display device containing the liquid crystal composition has a high response speed.
Compared with the prior art, the liquid crystal composition provided by the invention has the advantages of higher clearing point, lower viscosity, properly high absolute value of dielectric anisotropy, properly large optical anisotropy, wide nematic phase temperature range and good low-temperature stability, and a liquid crystal display comprising the liquid crystal composition has the advantages of good temperature adaptability, high response speed, low energy consumption and the like, so that the liquid crystal display has a good display effect.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
For convenience of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code listed in Table 2:
TABLE 2 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCCGF, wherein n in the code represents the number of C atoms of the left alkyl group, for example, n is 3, namely, the alkyl group is-C3H7(ii) a C in the code represents cyclohexane, G represents 2-fluoro-1, 4-phenylene, Frepresents-F.
The abbreviated codes of the test items in the following examples are as follows:
wherein,
the optical anisotropy is obtained by testing an Abbe refractometer under a sodium lamp (589nm) light source at 25 ℃;
Δε＝ε‖-ε⊥wherein, epsilon‖Is a dielectric constant parallel to the molecular axis,. epsilon⊥For the dielectric constant perpendicular to the molecular axis, test conditions: the test box is VA type at 25 deg.C and 1KHz, and the thickness of the test box is 6 μm.
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Comparative example 1
The liquid crystal composition of comparative example 1 was prepared with the compounds and weight percentages listed in table 3, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 3 liquid crystal composition formula and its test performance
Example 1
The liquid crystal composition of example 1 was prepared according to the compounds and weight percentages listed in table 4, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Example 2
The liquid crystal composition of example 2 was prepared according to the compounds and weight percentages listed in table 5, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Example 3
The liquid crystal composition of example 3 was prepared with the compounds and weight percentages listed in table 6, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
Example 4
The liquid crystal composition of example 4 was prepared according to the compounds and weight percentages listed in table 7, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 7 liquid crystal composition formulations and their test properties
Example 5
The liquid crystal composition of example 5 was prepared with the compounds and weight percentages listed in table 8, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 8 liquid crystal composition formulations and their test properties
Example 6
The liquid crystal composition of example 6 was prepared with the compounds and weight percentages listed in table 9, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 9 liquid crystal composition formulations and their test properties
Example 7
The liquid crystal composition of example 7 was prepared according to the compounds and weight percentages listed in table 10, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 10 liquid crystal composition formulations and their test properties
Example 8
The liquid crystal composition of example 8 was prepared with the compounds and weight percentages listed in table 11, and filled between two substrates of a liquid crystal display for performance testing, the test data are shown in the following table:
TABLE 11 liquid crystal composition formulations and their test properties
As can be seen from comparative example 1 and examples 1 to 8, the liquid crystal composition of the present invention has a high clearing point, a low viscosity, a suitably high absolute value of dielectric anisotropy, a suitably large optical anisotropy, a wide nematic phase temperature range, and a good low temperature stability, and a liquid crystal display comprising the liquid crystal composition of the present invention has advantages of good temperature adaptability, a fast response speed, low power consumption, and the like, thereby having a good display effect.
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the present invention is not limited thereto, and equivalent changes and modifications made according to the spirit of the present invention should be covered thereby.
Claims (12)
1. A liquid crystal composition, comprising:
at least one compound of the general formula I
At least one compound of the general formulae II-1 and/or II-2
At least one compound of the formula III
Wherein,
the R is1And R2Each independently represents-H, -F, a linear OR branched alkyl OR alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 12 carbon atoms, -OR1’OR2', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R1' represents an alkylene group of 1 to 12 carbon atoms or an alkenylene group of 2 to 12 carbon atoms, R2' represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms;
the R is3And R4Each independently represents-H, -F, a linear OR branched alkyl OR alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 12 carbon atoms, -OR3’OR4', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R3' represents an alkylene group of 1 to 12 carbon atoms or an alkenylene group of 2 to 12 carbon atoms, R4' represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms;
the R is5And R6Each independently represents a straight or branched, fluorinated or non-fluorinated alkyl or alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a fluorinated or non-fluorinated alkenyl or alkenyloxy group of 2 to 12 carbon atoms;
L1and L2Each independently represents-H, -F, -Cl, -CN or-NCS;
z is1、Z2And Z3Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；
The ringRing (C)Ring (C)And ringEach independently represent
And a, b, c and d each independently represent 0 or 1.
2. The liquid crystal composition of claim 1, further comprising at least one compound selected from the group consisting of general formulas iv-1 to iv-12:
wherein,
R7and R8Each independently represents a linear OR branched alkyl OR alkoxy group of 1 to 12 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, an alkenyl OR alkenyloxy group of 2 to 12 carbon atoms, -OR7’OR8', wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted with F, wherein R7' represents an alkylene group of 1 to 12 carbon atoms or an alkenylene group of 2 to 12 carbon atoms, R8' represents an alkyl group of 1 to 12 carbon atoms or an alkenyl group of 2 to 12 carbon atoms.
3. The liquid crystal composition of claim 1, wherein the compound of formula i is selected from the group consisting of one or more of the following structures:
4. the liquid crystal composition of claim 3, wherein the compound of formula i-1 is selected from the group consisting of one or more of the following compounds:
wherein,
R11and R21Each independently represents a linear or branched alkyl or alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl or alkenyloxy group having 2 to 10 carbon atoms, wherein one or more H of the alkyl or alkoxy group and the alkenyl or alkenyloxy group may be substituted by F;
R1' represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R2' represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
5. The liquid crystal composition of claim 3, wherein the compound of formula i-2 is selected from the group consisting of one or more of the following compounds:
wherein,
R12and R22Each independently represents a linear or branched alkyl or alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms,Alkenyl or alkenyloxy containing 2 to 10 carbon atoms, wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
R1' represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R2' represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
6. Liquid crystal composition according to claim 1, characterized in that the compound of formula ii-1 is preferably selected from the group consisting of one or more of the following compounds ii-1-1 to ii-1-20:
7. liquid crystal composition according to claim 1, characterized in that the compound of general formula ii-2 is preferably selected from the group consisting of one or more of the following compounds ii-2-1 to ii-2-27:
8. the liquid crystal composition of claim 1, wherein the compound of formula iii is selected from the group consisting of formula iii-1, formula iii-2, formula iii-3, and combinations thereof:
wherein,
the R is51、R52、R53、R61、R62And R63Each independently represents-H, -F, alkyl or alkoxy of 1-12 carbon atoms, alkenyl or alkenyloxy of 2-12 carbon atoms,Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
z is1、Z2And Z3Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-。
9. The liquid crystal composition of claim 8, wherein the compound of formula iii-1 is selected from the group consisting of:
wherein,
R51and R61represents-H, -F, alkyl or alkoxy of 1-7 carbon atoms, alkenyl or alkenyloxy of 2-7 carbon atoms.
10. The liquid crystal composition of claim 8, wherein the compound of formula iii-2 is selected from the group consisting of:
wherein,
R52and R62represents-H, -F, alkyl or alkoxy of 1-7 carbon atoms, alkenyl or alkenyloxy of 2-7 carbon atoms.
11. The liquid crystal composition of claim 8, wherein the compound of formula iii-3 is selected from the group consisting of:
wherein,
R53and R63represents-H, -F, alkyl or alkoxy of 1-7 carbon atoms, alkenyl or alkenyloxy of 2-7 carbon atoms.
12. A liquid crystal display device comprising the liquid crystal composition of any one of claims 1 to 11.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108587646A (en) * | 2018-06-20 | 2018-09-28 | 烟台丰蓬液晶材料有限公司 | A kind of liquid-crystal compounds containing four fluoro dihydro phenanthrene structures and its application |
| CN113105901A (en) * | 2021-04-07 | 2021-07-13 | 浙江汽车仪表有限公司 | High-reliability display material for automobile full-liquid crystal instrument panel |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103254907A (en) * | 2013-04-23 | 2013-08-21 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition with negative dielectric anisotropy |
| CN104334685A (en) * | 2012-07-04 | 2015-02-04 | Dic株式会社 | Nematic liquid crystal composition and liquid crystal display element using same |
| CN104371740A (en) * | 2013-08-14 | 2015-02-25 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and applications thereof |
| CN104513666A (en) * | 2014-10-10 | 2015-04-15 | 石家庄诚志永华显示材料有限公司 | Liquid crystal medium and application |
| CN104593011A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Cyclopropyl-contained negative dielectric anisotropic liquid crystal medium and application thereof |
| CN105176543A (en) * | 2014-06-17 | 2015-12-23 | 默克专利股份有限公司 | Liquid crystalline medium |
| WO2016184542A1 (en) * | 2015-05-20 | 2016-11-24 | Merck Patent Gmbh | Liquid-crystal medium |
| WO2017098933A1 (en) * | 2015-12-08 | 2017-06-15 | Jnc株式会社 | Liquid crystal composition and liquid crystal display element |
| CN107011922A (en) * | 2011-12-21 | 2017-08-04 | Dic株式会社 | Nematic liquid crystal composition and the liquid crystal display cells using the liquid-crystal composition |
| CN108690635A (en) * | 2017-04-05 | 2018-10-23 | 北京八亿时空液晶科技股份有限公司 | A kind of negative dielectric anisotropy liquid crystal composition and its application |
| CN108728121A (en) * | 2017-04-21 | 2018-11-02 | 北京八亿时空液晶科技股份有限公司 | A kind of negative dielectric liquid crystal composition and its application |
| CN108728113A (en) * | 2017-04-20 | 2018-11-02 | 北京八亿时空液晶科技股份有限公司 | A kind of nematic phase liquid crystal composition containing fluoroethoxy structure and its application |
-
2017
- 2017-09-28 CN CN201710894518.8A patent/CN107603640B/en active Active
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107011922A (en) * | 2011-12-21 | 2017-08-04 | Dic株式会社 | Nematic liquid crystal composition and the liquid crystal display cells using the liquid-crystal composition |
| CN104334685A (en) * | 2012-07-04 | 2015-02-04 | Dic株式会社 | Nematic liquid crystal composition and liquid crystal display element using same |
| CN103254907A (en) * | 2013-04-23 | 2013-08-21 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition with negative dielectric anisotropy |
| CN104371740A (en) * | 2013-08-14 | 2015-02-25 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and applications thereof |
| CN105176543A (en) * | 2014-06-17 | 2015-12-23 | 默克专利股份有限公司 | Liquid crystalline medium |
| CN104513666A (en) * | 2014-10-10 | 2015-04-15 | 石家庄诚志永华显示材料有限公司 | Liquid crystal medium and application |
| CN104593011A (en) * | 2015-02-15 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Cyclopropyl-contained negative dielectric anisotropic liquid crystal medium and application thereof |
| WO2016184542A1 (en) * | 2015-05-20 | 2016-11-24 | Merck Patent Gmbh | Liquid-crystal medium |
| WO2017098933A1 (en) * | 2015-12-08 | 2017-06-15 | Jnc株式会社 | Liquid crystal composition and liquid crystal display element |
| CN108690635A (en) * | 2017-04-05 | 2018-10-23 | 北京八亿时空液晶科技股份有限公司 | A kind of negative dielectric anisotropy liquid crystal composition and its application |
| CN108728113A (en) * | 2017-04-20 | 2018-11-02 | 北京八亿时空液晶科技股份有限公司 | A kind of nematic phase liquid crystal composition containing fluoroethoxy structure and its application |
| CN108728121A (en) * | 2017-04-21 | 2018-11-02 | 北京八亿时空液晶科技股份有限公司 | A kind of negative dielectric liquid crystal composition and its application |
Non-Patent Citations (5)
| Title |
|---|
| 孙贵祥: "新型侧向氟取代负介电各向异性液晶的合成与性质研究", 《中国博士学位论文全文数据库 信息科技辑》 * |
| 孙贵祥: "新型侧向氟取代负介电各向异性液晶的合成与性质研究", 《中国博士学位论文全文数据库 信息科技辑》, no. 03, 15 July 2005 (2005-07-15), pages 135 - 2 * |
| 李耀华: "侧向氟取代负介电各向异性液晶", 《山东化工》 * |
| 李耀华: "侧向氟取代负介电各向异性液晶", 《山东化工》, no. 06, 30 December 2002 (2002-12-30), pages 21 - 24 * |
| 高鸿锦 等: "《液晶与平板显示技术》", 30 June 2007, 北京邮电大学出版社, pages: 96 - 99 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108587646A (en) * | 2018-06-20 | 2018-09-28 | 烟台丰蓬液晶材料有限公司 | A kind of liquid-crystal compounds containing four fluoro dihydro phenanthrene structures and its application |
| CN113105901A (en) * | 2021-04-07 | 2021-07-13 | 浙江汽车仪表有限公司 | High-reliability display material for automobile full-liquid crystal instrument panel |
| CN113105901B (en) * | 2021-04-07 | 2023-02-21 | 浙江汽车仪表有限公司 | High-reliability display material for automobile full-liquid crystal instrument panel |
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