CN107674687B - Liquid crystal composition and liquid crystal display element or liquid crystal display - Google Patents
Liquid crystal composition and liquid crystal display element or liquid crystal display Download PDFInfo
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- CN107674687B CN107674687B CN201610621194.6A CN201610621194A CN107674687B CN 107674687 B CN107674687 B CN 107674687B CN 201610621194 A CN201610621194 A CN 201610621194A CN 107674687 B CN107674687 B CN 107674687B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 118
- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims description 179
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 26
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000005725 cyclohexenylene group Chemical group 0.000 claims description 10
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000004044 response Effects 0.000 abstract description 14
- 230000003287 optical effect Effects 0.000 abstract description 5
- 230000014759 maintenance of location Effects 0.000 abstract description 4
- 230000006750 UV protection Effects 0.000 abstract description 3
- 238000012360 testing method Methods 0.000 description 22
- 239000000463 material Substances 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- 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 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a liquid crystal composition, which comprises one or more compounds shown as formula I-a and/or formula I-b, one or more compounds shown as formula II and one or more compounds shown as formula III,
Description
Technical Field
The invention relates to the technical field of liquid crystal display, in particular to a liquid crystal composition and a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition.
Background
In the development process of the LCD, the liquid crystal for the LCD is developed towards a direction of faster response speed and better reliability, the high-speed response characteristic of the liquid crystal mixture is derived from the corresponding physical parameters of the components, such as rotational viscosity gamma1, elastic constant (K) and the like, the high Δ n is helpful for reducing the thickness of the liquid crystal cell, so as to improve the response speed, and meanwhile, the monomer with high brightness point is also helpful for the combination and matching of mixed crystals. Therefore, the ideal liquid crystal monomer should have the characteristics of low gamma1, high K, proper refractive index, high bright point and the like.
To achieve this feature, a strategy of introducing a double bond into a molecular structure is adopted in designing a molecule, and in general, the double bond is connected with a cyclohexyl group in a rigid core of a liquid crystal, or connected with the cyclohexyl group, a benzene ring through several methylene groups, so as to obtain features of high K, low viscosity, wide nematic phase temperature range, and the like.
Such as:
however, although liquid crystals in which double bonds are directly connected to benzene rings (conjugated olefinic liquid crystals) appear, they have not been applied to the formulation of commercial liquid crystals, since it was found in the test stage that such liquid crystals greatly reduce the charge retention of the liquid crystals, particularly after UV irradiation and heating. However, the liquid crystal in which the double bond is directly connected to the benzene ring is far superior to the liquid crystal constructed by other double bond connection schemes in the characteristics of high K, low viscosity and high clearing point, so that once the defect in reliability is overcome, the response speed level of the existing liquid crystal is greatly improved.
The invention overcomes the defect of low reliability of conjugated olefin liquid crystal by matching the liquid crystal mixture, so that the conjugated olefin liquid crystal can be applied to commercial liquid crystal, and the display speed and the reliability of the liquid crystal can be greatly improved.
Disclosure of Invention
The invention aims to provide a liquid crystal composition and a liquid crystal display element or a liquid crystal display containing the same, wherein the liquid crystal composition has low viscosity, can realize quick response, and simultaneously has moderate dielectric anisotropy delta epsilon, moderate optical anisotropy delta n and high stability to heat and light. The liquid crystal display element or the liquid crystal display comprising the liquid crystal composition has the technical scheme of wide nematic phase temperature range, proper birefringence anisotropy, very high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like. Accordingly, an object of the present invention is to provide a nematic liquid crystal composition comprising a benzene ring-conjugated olefin-based liquid crystal and other liquid crystal compositions in which a benzene ring-conjugated olefin-based liquid crystal compound is present.
Another object of the present invention is to provide a composition scheme which can provide a benzene ring conjugated olefin liquid crystal compound with high reliability.
In order to solve the technical problems, the invention provides a liquid crystal composition which comprises one or more compounds shown as formula I-a and/or formula I-b, one or more compounds shown as formula II and one or more compounds shown as formula III, namely, the liquid crystal composition provided by the invention necessarily comprises the compounds shown as formula II and the compounds shown as formula III, necessarily comprises one of the compounds shown as formula I-a and formula I-b, and also can simultaneously comprise the compounds shown as formula I-a and formula I-b
Wherein,
R1、R2each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group, a cyclobutyl group or a cyclopropyl group;
W1f, H, a C1-5 alkyl group or a fluorine-substituted C1-5 alkyl group;
W2、W3each independently represents F or H;
R21、R22each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and the double bond is not directly bonded to a benzene ring;
R3represents a C1-10 chain alkyl group, a fluorine-substituted C1-10 chain alkyl group, a C1-10 alkoxy group, a fluorine-substituted C1-10 alkoxy group, a C2-10 alkenyl group, a fluorine-substituted C2-10 alkenyl group, a C3-8 alkenyloxy groupOr a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and wherein any of the methylene groups may be replaced by a cyclopentyl group, a cyclobutyl group or a cyclopropyl group, and the double bond is not directly bonded to the benzene ring;
y represents independently F, an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, a carbon-substituted alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
X1-X16each independently represents H or F;
m and n each independently represent 1 or 2;
each independently represents one or two of cyclohexylene, cyclohexenylene, phenylene and/or fluorophenylene, and when m represents 2,
cannot simultaneously represent 2 phenylene groups and a fluorophenylene group, and when n represents 2,
cannot represent 2 phenylene groups and a fluorophenylene group at the same time.
Surprisingly, the liquid crystal composition of the invention can overcome the defect of low reliability, and achieve the purpose of quick response, and simultaneously has less defects of other parameters.
The technical scheme of the invention is further improved in that the compound shown in the formula I-a is preferably a compound shown in a formula I1 to a formula I27; the compounds shown in the formulas I-b are preferably compounds shown in formulas I28 to I41, the one or more compounds shown in the formulas II are preferably one or more compounds shown in formulas II1 to II 8, the one or more compounds shown in the formulas III are preferably one or more compounds shown in formulas III1 to III 8, wherein the total mass content of the compounds shown in the formulas I-a and the compounds shown in the formulas I-b is preferably 1-30%, and more preferably 3-15%;
wherein R is11Represents a C1-C5 linear alkyl group, wherein any methylene group can be replaced by cyclopentyl and cyclopropyl;
the total mass content of the compound shown in the formula II is preferably 1-60%, more preferably 20-55%
Wherein R is211、R221Each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms;
wherein,
R31each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
Y1each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group, a cyclopropyl group or a vinylene group, and the double bond is not directly bonded to a benzene ring.
The liquid crystal composition provided by the invention can also comprise one or more compounds shown as a formula IV,
wherein,
R4represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
each independently represents one or more of cyclohexylene, cyclohexenylene, phenylene and/or fluorophenylene;
(F) each independently represents H or F;
o represents 1, 2 or 3;
r represents 1 or 0;
q denotes F, OCF3、CF3、OCF2H；
P represents methyl or H.
Since the compound represented by the formula I-a has a high elastic constant, which leads to an increase in the threshold voltage of the liquid crystal composition, in the liquid crystal display, it is necessary to increase the dielectric anisotropy value of the mixture system in order to maintain a set target threshold voltage, while the compound represented by the formula IV is an ideal material for increasing the dielectric anisotropy value, and has the characteristics of high dielectric anisotropy, low viscosity, and the like. The liquid crystal composition provided by the invention has higher dielectric anisotropy value when added into the liquid crystal composition.
The one or more compounds shown as the formula IV are preferably one or more compounds shown as the following formulas IV 1 to IV 18, the total mass content of the one or more compounds shown as the formula IV is preferably 2 to 30 percent,
wherein R is41Each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms.
The compounds of formula IV have a relatively large dielectric constant and are used primarily for adjusting the dielectric anisotropy of the liquid-crystal mixtures in a relatively large direction.
The liquid crystal composition provided by the invention can also comprise one or more compounds shown as a formula V,
wherein,
R5each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
p and q each independently represent 0, 1 or 2;
z represents a single bond, -COO-),-CH2O-or CH2CH2-；
U represents F or-OCF3；
In liquid crystal displays, the refractive index of the liquid crystal mixture is required for the display mode used and the optical design of the liquid crystal panel. The compound shown in the formula V is added into the liquid crystal composition provided by the invention, so that the refractive index of the mixture can be adjusted as required, the rotational viscosity is kept low to improve the response speed, and the dielectric anisotropy value provided by the compound can reduce the proportion of high dielectric anisotropy components in the composition to further reduce the response time of the liquid crystal material. The one or more compounds shown as the formula V are preferably one or more compounds shown as the following formulas V1-V15, and the total mass content of the one or more compounds shown as the formula V is preferably 2-40%;
wherein R is51Each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
(F) each independently represents H or F.
The liquid crystal composition provided by the invention can also comprise one or more compounds shown as a formula VI,
wherein,
R61、R62each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
t represents 1 or 2;
s represents 0, 1 or 2;
Z1、Z2each independently represents a single bond, -COO-, -CH2O-or CH2CH2-；
In liquid crystal displays, negative liquid crystals require a liquid crystal component to provide negative dielectric anisotropy, and the compounds of formula VI are such materials. Meanwhile, in a positive IPS display mode, the transmittance of the liquid crystal panel can be improved by adding the negative liquid crystal material, so that the energy loss of the backlight source is reduced, and the effects of energy conservation and environmental protection are achieved.
The one or more compounds shown in the formula VI are preferably one or more compounds shown in the formula VI 1-VI 14, and the total mass content of the one or more compounds shown in the formula VI is preferably 5-50%;
wherein R is611、R621Each independently represents the number of carbon atomsIs an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms.
The compounds of the formula VI can be used in positively anisotropic liquid-crystal mixtures and also in negatively anisotropic liquid-crystal mixtures.
The liquid crystal composition provided by the invention can also comprise one or more compounds shown as the formula VII, the total mass content of the one or more compounds shown as the formula VII is preferably 2-15%,
wherein,
v represents-CH2O-, -O-or-S-;
wherein R is71、R72Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group.
In liquid crystal displays, negative liquid crystals require a liquid crystal component to provide negative dielectric anisotropy, and formula VII is such a material. The difference from formula VI is that in the same ratio, formula VII provides a much higher negative dielectric anisotropy than formula VI.
The one or more compounds represented by the formula VII are preferably one or more compounds represented by the following formulas VII 1 to VII 11,
wherein R is711、R721Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms.
The liquid crystal composition provided by the invention can also comprise one or more compounds shown as the formula VIII, the total mass content of the one or more compounds shown as the formula VIII is preferably 1-20%,
wherein,
R81、R82each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
p 'and q' each independently represent 1 or 2;
z' represents a single bond, -COO-, -CH2O-or CH2CH2-；
and when R is81When an alkyl group is represented, the alkyl group,
represents a phenylene group, p 'represents 1, Z' represents a single bond,
when q' represents 1, R82It does not represent an alkenyl group in which the olefinic bond is directly conjugated to the benzene ring M.
The liquid crystal display material can work in a nematic phase, and when the temperature is higher than a clearing point, the liquid crystal material enters an isotropic state and loses response to an electric field. Therefore, in order to ensure the working temperature range of the liquid crystal material, a material with high clearing point is added, and the material shown in the formula VIII has the characteristic.
The one or more compounds represented by the formula VIII are preferably one or more compounds represented by the formulae VIII1-VIII14,
wherein R is81、R82Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
and R in the formulas VIII1-VIII4 and VIII10-VIII1382Alkenyl groups which are not directly bonded to the benzene ring by an olefinic bond.
The invention also relates to a liquid crystal display element or a liquid crystal display comprising any one of the liquid crystal compositions; the display element or display is an active matrix display element or display or a passive matrix display element or display.
The liquid crystal display element or liquid crystal display is preferably an active matrix addressed liquid crystal display element or liquid crystal display.
The active matrix display element or the display is specifically a TN-TFT or IPS-TFT liquid crystal display element or a display.
Due to the adoption of the technical scheme, the technical progress of the invention is as follows:
the liquid crystal composition provided by the invention has lower viscosity, can realize quick response, and simultaneously has moderate dielectric anisotropy delta epsilon, moderate optical anisotropy delta n and high stability to heat and light. The liquid crystal material containing the liquid crystal composition provided by the invention not only has good chemical and thermal stability, but also has good stability to electric fields and electromagnetic radiation. In addition, the liquid crystal material for thin film transistor technology (TFT-LCD) has the performances of wide nematic phase temperature range, proper birefringence anisotropy, very high resistivity, good ultraviolet resistance, high charge retention rate, low vapor pressure and the like.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples, but the present invention is not limited to the following examples.
The method is a conventional method unless otherwise specified.
The starting materials are commercially available from the open literature unless otherwise specified.
The percentages are not specifically indicated, and are all mass percentages.
The temperature is in degrees centigrade (DEG C), and the specific meanings and test conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
S-N represents the crystalline to nematic melting point (. degree. C.) of the liquid crystal;
delta n represents optical anisotropy, no is the refractive index of ordinary light, ne is the refractive index of extraordinary light, the test conditions are 25 +/-2 ℃, 589nm and the Abbe refractometer tests;
Δ ∈ represents dielectric anisotropy, Δ ∈ ═ ε/ε ×, where ε/is the dielectric constant parallel to the molecular axis, ε × is the dielectric constant perpendicular to the molecular axis, the test conditions were 25 ± 0.5 ℃, 20 μm parallel cell, INSTEC: ALCT-IR1 test;
γ 1 represents rotational viscosity (mPa. multidot.s) at 25. + -. 0.5 ℃ in a 20 μm parallel cell INSTEC: ALCT-IR1 test;
rho represents resistivity (omega cm), the test condition is 25 +/-2 ℃, and the test instrument is a TOYO SR6517 high-impedance instrument and an LE-21 liquid electrode.
VHR represents the voltage holding ratio (%), and the test conditions are 20 +/-2 ℃, voltage +/-5V, pulse width 10ms and voltage holding time 16.7 ms. The testing equipment is a TOYO Model6254 liquid crystal performance comprehensive tester.
Tau represents response time (ms), the test instrument is DMS-501, the test condition is 25 +/-0.5 ℃, the test box is a 3.3-micrometer IPS test box, the electrode spacing and the electrode width are both 10 micrometers, and the included angle between the friction direction and the electrode is 10 degrees.
T (%) represents transmittance, T (%) is 100% bright state (Vop) brightness/light source brightness, the test device DMS501, the test conditions are 25 ± 0.5 ℃, the test cell is a 3.3 μm IPS test cell, the electrode spacing and the electrode width are both 10 μm, and the angle between the rubbing direction and the electrodes is 10 °
The liquid crystal monomer structure of the embodiment of the invention is represented by codes, and the code representation methods of the liquid crystal ring structure, the end group and the connecting group are shown in the following tables (I) and (II)
Table (one): corresponding code of ring structure
Table (ii): corresponding codes for end groups and linking groups
Examples are:
example 1:
example 2:
example 3:
example 4:
example 5:
example 6:
example 7:
example 8:
example 9
Example 10
In example 10, the initial VHR was 97.03% at 166.7ms at a VHR test condition of 60 ℃ at 1V; after UV irradiation of 50mw/cm2 for 100s, the VHR was tested to be 93.13%; the VHR was tested to be 97.19% by heating at 100 ℃ for 1 h.
Comparative example 1
In comparative example 1, where component I was removed compared to example 10, the initial VHR was 97.12% at 166.7ms at VHR test conditions of 60 ℃, 1V; after UV irradiation of 50mw/cm2 for 100s, the VHR was tested to be 93.26%; heating at 100 ℃ for 1h tested a VHR of 92.33%. It can be seen that the high temperature VHR drops significantly by around 5 percentage points when there is no component I in the combination.
Comparative example 2
In comparative example 2, in which the III component was removed and the remaining components were unchanged, the initial VHR was 97.32% at 166.7ms under VHR test conditions of 60 ℃ at 1V, compared to example 10; after UV irradiation of 50mw/cm2 for 100s, the VHR was tested to be 63.33%; the VHR was tested to 57.89% by heating at 100 ℃ for 1 h. It can be seen that the UV VHR drops by 30 percentage points and after heating by 40 percentage points when there is no III component in the combination.
Comparative example 3
In example 10, when 3CBBV1 was replaced with 3CBB3, it was found that CP decreased, γ 1 increased, response speed deteriorated, and liquid crystal phase temperature range narrowed.
It can be seen that: compared with 3CBB3, the 3CBBV1 has the effects of obviously improving the response speed and expanding the use temperature range of the liquid crystal device.
Example 11
Example 12
Example 13
Example 14
Example 15
Example 16
Example 17
Example 18
Example 19
Example 20
Example 21
Example 22
Claims (12)
1. A liquid crystal composition comprising one or more compounds of formula I-a, one or more compounds of formulae I28 to I35, one or more compounds of formulae II1, II 2, II 6 to II 8 and one or more compounds of formula III,
wherein,
R1represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group, a cyclobutyl group or a cyclopropyl group;
W1f, H, a C1-5 alkyl group or a fluorine-substituted C1-5 alkyl group;
W2、W3each independently represents F or H;
R11represents a C1-C5 linear alkyl group, wherein any methylene group can be replaced by cyclopentyl and cyclopropyl;
R211、R221each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms;
R3represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and wherein any of the methylene groups may be replaced by a cyclopentyl group, a cyclobutyl group or a cyclopropyl group, and the double bond is not directly connected to a benzene ring;
y represents independently F, an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, a carbon-substituted alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
X1-X2、X5-X16each independently represents H or F;
m represents 2;
each independently represents one or two of cyclohexylene, cyclohexenylene, phenylene and/or fluorophenylene, and
cannot represent 2 phenylene groups and a fluorophenylene group at the same time;
the sum of the total mass contents of the compound shown in the formula I-a and the compounds shown in the formulae I28 to I35 in the liquid crystal composition is 3-15%; the total mass content of the compounds shown in the formulas II1, II 2, II 6 to II 8 in the liquid crystal composition is 20-55%.
2. The liquid-crystal composition according to claim 1, wherein the compound represented by the formula i-a is a compound represented by the formulae i1 to i 8, i 17 to i 24; the one or more compounds shown in the formula III are one or more compounds shown in formulas III 1-III 8,
wherein R is11Represents a C1-C5 linear alkyl group, wherein any methylene group can be replaced by cyclopentyl and cyclopropyl;
wherein,
R31each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
Y1each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group, a cyclopropyl group or a vinylene group, and the double bond is not directly bonded to a benzene ring.
3. The liquid crystal composition of claim 1 or 2, wherein the liquid crystal composition comprises one or more compounds of formula IV,
wherein,
R4represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
each independently represents one or more of cyclohexylene, cyclohexenylene, phenylene and/or fluorophenylene;
(F) each independently represents H or F;
o represents 1, 2 or 3;
r represents 1 or 0;
q denotes F, OCF3、CF3、OCF2H；
P represents methyl or H.
4. The liquid crystal composition of claim 3, wherein the one or more compounds of formula IV are one or more compounds selected from the group consisting of,
wherein R is41Each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms.
5. The liquid crystal composition of claim 1 or 2, wherein the liquid crystal composition comprises one or more compounds of formula V,
wherein,
R5each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
p and q each independently represent 0, 1 or 2;
z represents a single bond, -COO-, -CH2O-or CH2CH2-；
U represents F or-OCF3；
6. The liquid crystal composition of claim 5, wherein the one or more compounds of formula V are one or more compounds selected from the group consisting of,
wherein R is51Each independently represents a straight-chain alkyl group having 1 to 5 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
(F) each independently represents H or F.
7. The liquid crystal composition of claim 1 or 2, wherein the liquid crystal composition comprises one or more compounds of formula VI
Wherein,
R61、R62each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
t represents 1 or 2;
s represents 0, 1 or 2;
Z1、Z2each independently represents a single bond, -COO-, -CH2O-or CH2CH2-；
8. The liquid crystal composition as claimed in claim 7, wherein the one or more compounds of the formula VI are one or more compounds of the formulae VI 1 to VI 14,
wherein R is611、R621Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms.
9. Liquid crystal composition according to claim 1 or 2, characterized in that the liquid crystal composition comprises one or more compounds of the formula VII,
wherein,
v represents-CH2O-, -O-or-S-;
R71、R72each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group.
10. The liquid crystal composition of claim 1 or 2, wherein the liquid crystal composition comprises one or more compounds of formula VIII,
wherein,
R81、R82each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
p 'and q' each independently represent 1 or 2;
z' represents a single bond, -COO-, -CH2O-or CH2CH2-；
and when R is81When an alkyl group is represented, the alkyl group,
represents a phenylene group, p 'represents 1, Z' represents a single bond,
when q' represents 1, R82It does not represent an alkenyl group in which the olefinic bond is directly conjugated to the benzene ring M.
11. The compound of claim 10, wherein the one or more compounds of formula VIII is one or more of the following compounds,
wherein R is81、R82Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and any of the methylene groups may be replaced by a cyclopentyl group or a cyclopropyl group;
and R in the formulas VIII1-VIII3 and VIII10-VIII1182Alkenyl groups which are not directly bonded to the benzene ring by an olefinic bond.
12. A liquid crystal display element or a liquid crystal display comprising the liquid crystal composition according to any one of claims 1 to 11, wherein the display element or display is an active matrix display element or display or a passive matrix display element or display.
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