CN111394108A - Liquid crystal composition, liquid crystal display element and liquid crystal display - Google Patents
Liquid crystal composition, liquid crystal display element and liquid crystal display Download PDFInfo
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- CN111394108A CN111394108A CN202010352217.4A CN202010352217A CN111394108A CN 111394108 A CN111394108 A CN 111394108A CN 202010352217 A CN202010352217 A CN 202010352217A CN 111394108 A CN111394108 A CN 111394108A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 199
- 239000000203 mixture Substances 0.000 title claims abstract description 156
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 125000004432 carbon atom Chemical group C* 0.000 claims description 109
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 239000011159 matrix material Substances 0.000 claims description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000004979 cyclopentylene group Chemical group 0.000 claims description 9
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 206010047571 Visual impairment Diseases 0.000 abstract description 13
- 230000006750 UV protection Effects 0.000 abstract description 7
- 230000007547 defect Effects 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 description 50
- 230000000875 corresponding effect Effects 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 25
- 238000009472 formulation Methods 0.000 description 24
- 230000032683 aging Effects 0.000 description 19
- -1 methylcyclopropylidene group Chemical group 0.000 description 18
- 238000002834 transmittance Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000008859 change Effects 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 1
- 101100263680 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) VHR2 gene Proteins 0.000 description 1
- 101000803389 Viola hederacea Root cyclotide 1 Proteins 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004976 cyclobutylene group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring 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
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention relates to a liquid crystal composition, a liquid crystal display element comprising the liquid crystal composition and a liquid crystal display, belonging to the field of liquid crystal display. The liquid crystal composition comprises one or more compounds shown as a formula I, one or more compounds shown as a formula II and one or more compounds shown as a formula III, and has the characteristics of good ultraviolet resistance and high temperature resistance⊥And/Δ, and good low temperature solubility, can improve afterimage defects.
Description
Technical Field
The invention belongs to the technical field of liquid crystal display, and particularly relates to a liquid crystal composition and a liquid crystal display element or a liquid crystal display containing the liquid crystal composition.
Background
With the development of Display technology, flat panel Display devices such as liquid Crystal displays (L liquid Crystal displays, L CDs) have advantages of high image quality, power saving, thin body, and wide application range, and thus are widely used in various consumer electronics products such as mobile phones, televisions, personal digital assistants, digital cameras, notebook computers, desktop computers, and the like, and become the mainstream of Display devices.
In the process of using the liquid crystal display, the liquid crystal composition is constantly influenced by light radiation and heat radiation, and meanwhile, in the process of manufacturing the liquid crystal display or the liquid crystal composition, the liquid crystal composition is inevitably contacted by light and heat, and the light and heat contact, especially the light and high temperature in an ultraviolet band, can cause that liquid crystal molecules are negatively influenced on the aspect of impurities, so that the change of anchoring capability of the liquid crystal molecules is influenced, and further the display effect of the liquid crystal display is influenced.
Therefore, how to provide a liquid crystal composition having good uv and high temperature resistance and capable of improving the image sticking defect is a problem to be solved in the art.
Disclosure of Invention
In order to solve the technical problems in the prior art, the invention provides a liquid crystal composition which can improve the defect of afterimage, and has good ultraviolet resistance, high temperature resistance and high performance⊥/Δ。
The invention also provides a liquid crystal display element or a liquid crystal display containing the liquid crystal composition.
Specifically, the present invention comprises the following:
in a first aspect of the invention, there is provided a liquid crystal composition comprising one or more compounds of formula I, one or more compounds of formula II, and one or more compounds of formula III,
in the formula I, Z1Represents a carbon atomAlkylene of a number of 1 to 20, and any one or more H atoms in the aforementioned alkylene is optionally substituted by halogen, any one or more non-adjacent-CH2-optionally substituted by-O-;
in the formula II, R represents alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms or alkenyloxy with 3-8 carbon atoms;
in the formula III, R1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and p represents 0 or 1.
In another aspect of the present invention, there is provided a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition of the present invention, the liquid crystal display element being an active matrix display element or a passive matrix display element, and the liquid crystal display being an active matrix display or a passive matrix display.
The liquid crystal composition has good ultraviolet resistance and high-temperature resistance and high performance⊥And/delta, and the residual image defect can be improved.
The liquid crystal display element and the liquid crystal display have no residual image or the residual image is not obvious, and have high voltage holding ratio, good ultraviolet resistance, high temperature resistance and high transmittance by comprising the liquid crystal composition.
Detailed Description
[ liquid Crystal composition ]
The liquid crystal composition of the present invention comprises: one or more compounds of formula I, one or more compounds of formula II, and one or more compounds of formula III,
in the formula I, Z1Represents an alkylene group having 1 to 20 carbon atoms in which any one or more H atoms are optionally substituted by halogen, any one or more non-adjacent-CH2-optionally substituted by-O-;
in the formula II, R represents alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms or alkenyloxy with 3-8 carbon atoms;
in the formula III, R1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and p represents 0 or 1.
Z of the foregoing1The alkylene group having 1 to 20 carbon atoms may be a linear or branched alkylene group. In addition, the aforementioned alkylene group optionally has a ring structure.
The liquid crystal composition of the invention has good ultraviolet resistance and high temperature resistance and high performance by using the combination of the compound shown in the formula I, the compound shown in the formula II and the compound shown in the formula III⊥And/Δ, and an afterimage defect can be improved.
Optionally, one or more of the compounds of formula I is selected from the group consisting of compounds of formula I1 to formula I13,
optionally, the one or more compounds of formula II are selected from the group consisting of compounds of formula II 1 to formula II 4,
optionally, the one or more compounds of formula III are selected from the group consisting of compounds of formulae III 1 to III 8,
the liquid crystal composition of the present invention is preferably a positive dielectric anisotropic liquid crystal composition.
In the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by formula I added to the liquid crystal composition is not particularly limited, and may be 0.001 to 1%, preferably 0.05 to 0.1%, relative to the total amount of other components of the liquid crystal composition excluding the compound represented by formula I; the amount (mass ratio) of the compound represented by the formula II added to the liquid crystal composition is not particularly limited, and may be 1 to 60%, preferably 1 to 25%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I; the amount (mass ratio) of the compound represented by the formula III added to the liquid crystal composition is not particularly limited, and may be 1 to 60%, preferably 1 to 30%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
The liquid crystal composition of the invention optionally further comprises one or more compounds shown in the following formula IV,
in the formula IV, R2、R3Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
The compound shown in the formula IV has the characteristics of low rotational viscosity and good intersolubility with other compounds. The liquid crystal composition contains the compound shown in the formula IV, so that the response speed of the liquid crystal composition is further improved.
The amount (mass ratio) of the compound represented by the formula IV added to the liquid crystal composition is not particularly limited, and may be, for example, 10 to 70%, preferably 20 to 60%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Optionally, the compound shown in the formula IV is selected from the group consisting of compounds shown in formulas IV 1 to IV 16,
the liquid crystal composition of the present invention may optionally further comprise one or more compounds represented by the following formula V in addition to the aforementioned compounds represented by the formula II or III,
in formula V, R4Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R4Any one or more-CH of the groups shown2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z2Represents a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
X1、X2each independently represents a H atom or a F atom; x3Represents a H atomAn F atom or a methyl group;
Y1represents-F, -CF3、-OCF3、-OCF2H or-OCH2F；
m represents 0, 1 or 2.
The compound shown in the formula V is positive dielectric anisotropy, and the threshold voltage of the liquid crystal composition can be further adjusted by the compound shown in the formula V.
The amount (mass ratio) of the compound represented by the formula V to be added to the liquid crystal composition is not particularly limited, and may be 1 to 50%, preferably 5 to 30%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
As R in the aforementioned formula V4One or more non-adjacent-CH in the alkyl with 1-10 carbon atoms2Examples of the group substituted with a cyclopropylene group, a cyclobutylene group or a cyclopentylene group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a methylcyclopropylidene group, an ethylcyclopropylidene group, a propylcyclopropylidene group, an isopropylcyclopropylidene group, a n-butylcyclopropylidene group, an isobutylcyclopropylidene group, a tert-butylcyclopropylidene group, a methylcyclobutylene group, an ethylcyclobutylidene group, a propylcyclobutylidene group, an isopropylidene group, a n-butylidene group, an isobutylcyclobutylidene group, a tert-butylidene group, a methylcyclopentylene group, an ethylcyclopentylidene group, a propylcyclopentylidene group, an isopropylcyclopentylidene group, a n-butylcyclopentylidene group and an isobutylcyclopentylidene group.
Optionally, the one or more compounds of formula V are selected from the group consisting of compounds of formulae V1-V25,
in the formulae V1-V25, R4With R in the compounds of the formula V4Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R4Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene; (F) in the formula V1-formula V6 each independently represents a H atom or a F atom; - (O) CF in the formula V73represents-CF3or-OCF3。
The liquid crystal composition of the invention optionally further comprises one or more compounds shown in the formula VI,
in formula VI, R5、R6Each independently represents an alkyl group having 1 to 10 carbon atoms, an 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 have a high clearing point and elastic constant, in particular the splay elastic constant K11The liquid crystal composition of the invention contains the compound shown in the formula VI, which is beneficial to improving the clearing point and the splay elastic constant K of the liquid crystal composition11。
When the compound represented by the formula VI is contained in the liquid crystal composition of the present invention, the amount of the compound represented by the formula V to be added (mass ratio) to the liquid crystal composition is not particularly limited, and may be 1 to 30%, preferably 5 to 20%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Optionally, the compound shown in the formula VI is selected from the group consisting of compounds shown in formulas VI 1 to VI 4,
wherein R is51、R61Each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms; among them, examples of the alkenyl group having 2 to 6 carbon atoms include a vinyl group, a 2-propenyl group and a 3-pentenyl group. R62Represents an alkoxy group having 1 to 5 carbon atoms.
The liquid crystal composition of the present invention optionally further comprises one or more compounds represented by the following formula VII,
in the formula VII, R7、R8Each independently represents an alkyl group having 1 to 10 carbon atoms, an 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;
F1、F2、F3Each independently represents a H atom or a F atom, and F2、F3Not simultaneously being F atoms.
The compounds of formula VII have a high clearing point. By containing the compound represented by the formula VII in the liquid crystal composition of the present invention, the clearing point of the liquid crystal composition of the present invention can be significantly improved.
When the liquid crystal composition of the present invention contains the compound represented by the formula VII, the amount (mass ratio) of the compound represented by the formula VII added to the liquid crystal composition is not particularly limited, and may be 1 to 10%, preferably 2 to 5%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Alternatively, the compounds of formula VII mentioned above are selected from the group consisting of compounds of formulae VII 1 to VII 3,
wherein R is71、R81Each independently preferably represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms.
The liquid crystal composition of the invention optionally further comprises one or more compounds shown in the following formula VIII,
in the formula VIII, R9、R10Each independently represents an alkyl group having 1 to 10 carbon atoms, an 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 R9、R10Any one or more non-adjacent-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z3represents a single bond, -CF2O-、-CH2CH2-or-CH2O-；Z4Represents a single bond, -CH2CH2-or-CH2O-；
q represents 1 or 2; n represents 0, 1 or 2.
The compound shown in the formula VIII has larger vertical dielectric constant, the vertical dielectric constant of the liquid crystal composition can be adjusted according to different use conditions, the liquid crystal composition can keep low rotational viscosity, so that the vertical dielectric constant of the liquid crystal composition is further improved on the premise of slightly sacrificing the response speed, and the transmittance of the liquid crystal composition is improved on the basis of maintaining a certain response speed.
In the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula VIII added to the liquid crystal composition is not particularly limited, and may be 1 to 35%, preferably 5 to 30%, relative to the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Optionally, the one or more compounds of formula VIII are selected from the group consisting of compounds of formulae VIII 1 to VIII 21,
wherein R is91、R101Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R91、R101Any one or more of the radicals indicated being unconnected-CH2-optionally each independently substituted with cyclopentylene, cyclobutyl or cyclopropylene.
The liquid crystal composition of the present invention optionally further comprises one or more compounds represented by formula IX,
in the formula IX, R11、R12Each 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 R11、R12Any one or more non-adjacent-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene; w represents-O-, -S-or-CH2O-。
The compound shown in the formula IX has larger vertical dielectric constant compared with the compound shown in the formula VIII, and the larger vertical dielectric constant can be obtained by adding a small amount of the compound shown in the formula IX, so that the transmittance of the liquid crystal composition is further improved.
In the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula IX added to the liquid crystal composition is not particularly limited, and may be, for example, 1 to 15%, preferably 2 to 10%, relative to the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Alternatively, the compound of formula IX is selected from the group consisting of compounds of formula IX 1 through formula IX 8,
wherein R is111、R121Each independently represents an alkyl group having 2 to 6 carbon atoms.
In the liquid crystal composition of the present invention, a dopant having various functions may be optionally added, and when a dopant is contained, the content of the dopant is preferably 0.01 to 1% by mass in the liquid crystal composition, and examples of the dopant include an antioxidant, an ultraviolet absorber, and a chiral agent.
Examples of the antioxidant agent include, but are not limited to,
wherein t represents an integer of 1 to 10.
[ liquid Crystal display element, liquid Crystal display ]
The present invention also relates to a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition of the present invention, wherein the display element is an active matrix display element or a passive matrix display element, and the display is an active matrix display or a passive matrix display.
Optionally, the liquid crystal display element or the liquid crystal display of the invention includes a first substrate and a second substrate, and the first substrate and the second substrate are arranged in parallel relatively. The first substrate comprises a pixel electrode, a first alignment layer is arranged on the pixel electrode, the second substrate comprises a common electrode, and a second alignment layer is arranged on the common electrode. The liquid crystal composition is poured between the first substrate and the second substrate, and a One Drop Fill (ODF) method may be used.
Optionally, the liquid crystal display element or the liquid crystal display comprises an alignment layer formed by a PI with medium and high resistivity. By medium to high resistivity PI is meant a resistivity higher than 1013PI (polyimide) of Ω · m.
The liquid crystal display element and the liquid crystal display provided by the invention do not have residual images or have inconspicuous residual images, and have high voltage holding ratio, good ultraviolet resistance, high temperature resistance, high transmittance and low threshold voltage by comprising the liquid crystal composition provided by the invention.
The liquid crystal display element and the liquid crystal display of the present invention are not limited in structure as long as they contain the liquid crystal composition of the present invention, and those skilled in the art can select an appropriate structure of the liquid crystal display element and the liquid crystal display according to the desired performance.
Examples
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method unless otherwise specified, the used raw materials can be obtained from a public commercial way unless otherwise specified, the percentages refer to mass percentage (the total amount of other components of the liquid crystal composition excluding the compound shown in the formula I is recorded as 100%), the temperature is centigrade (DEG C), the liquid crystal compound is also called as a liquid crystal monomer, and the specific meanings of other symbols and the test conditions are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
Δ n represents optical anisotropy, and Δ n ═ ne-noWherein n isoRefractive index of ordinary light, neThe refractive index of the extraordinary ray is measured under the conditions of 25 +/-2 ℃ and 589nm, and the Abbe refractometer is used for testing;
Δ represents dielectric anisotropy, Δ ═∥-⊥Wherein, in the step (A),∥is the dielectric constant parallel to the molecular axis,⊥the dielectric constant perpendicular to the molecular axis is measured under the conditions of 25 +/-0.5 ℃ and 20-micron antiparallel box, and the INSTEC is A L CT-CUST-4C test;
tr (%) represents transmittance, Tr (%) is 100% bright state (Vop) brightness/light source brightness, the test equipment DMS501, the test conditions are 25 ± 0.5 ℃, the test cell is a 3.2 micrometer FFS test cell, the electrode spacing is 5 micrometers, the electrode width is 3 micrometers, and the angle between the rubbing direction and the electrode is 7 °;
VHR represents the voltage holding ratio (%), and the test conditions are 60 +/-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;
K11the test conditions for the splay elastic constant are 25 +/-2 ℃, INSTEC A L CT-CUST-4C and 20 micron parallel box;
γ1representing rotational viscosity (mPas) at 25. + -. 0.5 ℃ in a 20 micron antiparallel box, INSTEC: A L CT-CUST-4C test.
Afterimage: the residual image of the liquid crystal display device was evaluated by visually observing the residual level of the fixed pattern in the case of performing uniform display in the full screen, on a 4-scale basis as follows, after displaying the fixed pattern for 1000 hours in the display region:
◎ has no residue
○ has very little residue and is acceptable level
△ has residue at an unacceptable level
× remained, quite bad.
The preparation method of the liquid crystal composition comprises the following steps: weighing each liquid crystal monomer according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker filled with each liquid crystal monomer on a magnetic stirring instrument for heating and melting, adding a magnetic rotor into the stainless steel beaker after the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The liquid crystal monomer structure used in 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 1 and 2.
Table 1: corresponding code of ring structure
Table 2: corresponding codes for end groups and linking groups
Examples are:
Example 1:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 3 below.
Table 3: formulation and corresponding Properties of the liquid Crystal composition of example 1
Example 2:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 4 below.
Table 4: formulation and corresponding Properties of the liquid Crystal composition of example 2
Example 3:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 5 below.
Table 5: formulation and corresponding Properties of the liquid Crystal composition of example 3
Example 4:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 6 below.
Table 6: formulation and corresponding Properties of the liquid Crystal composition of example 4
Example 5:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 7 below.
Table 7: formulation and corresponding Properties of the liquid Crystal composition of example 5
Example 6:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 8 below.
Table 8: formulation and corresponding Properties of the liquid Crystal composition of example 6
Example 7:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 9 below.
Table 9: formulation and corresponding Properties of the liquid Crystal composition of example 7
Example 8:
the formulation and corresponding properties of the liquid crystal composition are shown in table 10 below.
Table 10: formulation and corresponding Properties of the liquid Crystal composition of example 8
Liquid crystal compositions obtained by replacing the compound represented by the formula I7 in example 8 with compounds represented by the formulae I2, I6 and I11 in equal amounts were prepared as examples 9, 10 and 11, respectively.
Comparative example 1:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 11 below.
Table 11: formulation and corresponding Properties of the liquid Crystal composition of comparative example 1
In contrast to example 6, the liquid crystal composition of comparative example 1, which did not contain the compound represented by formula I, formula II or formula III, used the compound PGUQU-3-F, PGUQU-4-F in place of the compound DPUQU-3-F, DPUQU-4-F in equal amounts and the compound CPU-3-F, CPU-4-F in place of the compound DPU-3-F, DPU-4-F in equal amounts.
Comparative example 2:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 12 below.
Table 12: formulation and corresponding Properties of the liquid Crystal composition of comparative example 2
In contrast to example 6, comparative example 2 does not contain the compound of formula I, and the compound of formula T-1 below is used in place of the compound of formula I in equal amounts.
Comparative example 3:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 13 below.
Table 13: formulation and corresponding Properties of the liquid Crystal composition of comparative example 3
In contrast to example 6, in comparative example 3, which does not contain the compound of formula II, the compound DGUQU-3-F, DGUQU-4-F is used in equal amounts instead of the compound DPUQU-3-F, DPUQU-4-F of formula II.
Comparative example 4:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 14 below.
Table 14: formulation and corresponding Properties of the liquid Crystal composition of comparative example 4
In comparison with example 6, comparative example 4 did not contain the compound represented by formula III, and the compound CPU-3-F, CPU-4-F was used in place of DPU-3-F, DPU-4-F in equal amounts while keeping the dielectric anisotropy Δ and the optical anisotropy Δ n substantially the same as those of example 6.
The reliability of the liquid crystal composition can be evaluated by testing the change of VHR by ultraviolet and high temperature aging tests. The smaller the VHR data change before and after the ultraviolet and high temperature test of the liquid crystal composition, the stronger the ultraviolet and high temperature resistance of the liquid crystal composition. Therefore, the stronger the capability of the liquid crystal composition to resist the damage of the external environment in the working process, the higher the reliability of the liquid crystal composition. Therefore, the ultraviolet and high temperature resistance can be judged by comparing the change of VHR data of the liquid crystal compositions provided by each example and comparative example before and after the aging test.
First, before the ultraviolet and high-temperature aging test, VHR data of the liquid crystal composition was measured as initial VHR data, and then, the ultraviolet and high-temperature aging test was performed on the liquid crystal composition, and after the test, VHR data of the liquid crystal composition was measured again.
The aging test is divided into two stages,
the first stage aging test conditions are as follows. Ultraviolet aging test: placing the liquid crystal composition at a wavelength of 365nm and an irradiance of 50mw/cm2Under an ultraviolet lamp, irradiating 5000mJ energy; high-temperature aging test: the liquid crystal composition was placed in an oven at 100 ℃ for 1 hour.
The second stage aging test conditions are as follows. Ultraviolet aging test: the liquid crystal composition is placed under 20000nit backlight for 1000 hours; high-temperature aging test: the liquid crystal composition was placed in an oven at 60 ℃ for 120 hours.
The liquid crystal compositions provided in examples and comparative examples were tested for VHR and afterimage after being subjected to the first-stage and second-stage aging tests, respectively.
The liquid crystal compositions provided in examples and comparative examples were poured into liquid crystal test cells containing two different types of PI (polyimide), respectively, to perform an image sticking test.A liquid crystal test cell A contained a PI having a medium-high resistivity, e.g., Nissan SE-7492, Nissan SE-6414, and a liquid crystal test cell B contained a PI having a low resistivity, e.g., Nissan SE-5414, JSR A L16301. the test results are shown in tables 15 and 16 below.
In tables 15 and 16, VHR1 is the test data after the first stage aging test, VHR2 is the test data after the second stage aging test, afterimage a is the afterimage test result of the liquid crystal composition in liquid crystal test cell a, and afterimage B is the afterimage test result of the liquid crystal composition in liquid crystal test cell B.
Table 15: data from the test of reliability of the examples and comparative examples after the first stage aging test
As can be seen from table 15 above, the liquid crystal compositions provided in the examples of the present invention had very small VHR decrease after uv and high temperature aging tests as compared with comparative example 1. In addition, the afterimage defect is improved more obviously. Compared with the comparative example 2, after the first-stage aging test, although the residual image improvement effect is consistent when the middle-high resistivity PI liquid crystal test box is used, the residual image improvement effect is better when the low resistivity PI liquid crystal test box is used.
Table 16: reliability test data of examples and comparative examples after second stage aging test
As can be seen from Table 16, the liquid crystal compositions provided in the examples have less VHR drop after UV and high temperature aging tests and more significant improvement of the afterimage compared with the comparative examples. In particular, the liquid crystal composition of the example using the compound represented by formula I7 can achieve a better afterimage improvement effect in combination with high-resistivity PI.
Table 17 shows the penetration test data of the examples and comparative examples, wherein Tr represents the penetration.
Table 17: penetration test data for examples and comparative examples
| ε⊥/Δε | Tr(％) | |
| Example 6 | 0.39 | 37.28 |
| Comparative example 4 | 0.37 | 35.50 |
Comparing the liquid crystal compositions provided in example 6 and comparative example 4, the liquid crystal composition provided in example 6 has a ratio of vertical dielectric constant to dielectric constant⊥Larger/delta, and the transmittance of the liquid crystal display element or the liquid crystal display and the liquid crystal composition⊥The/delta correlation is that under the premise of keeping the dielectric anisotropy delta and the optical anisotropy delta n basically the same,⊥the larger the/. DELTA.is, the larger the transmittance of the liquid crystal display element or the liquid crystal display is. As can be seen from table 17, the liquid crystal composition of example 6 of the present invention can improve the transmittance by about 5% compared to comparative example 4.
In conclusion, the liquid crystal composition provided by the invention has good ultraviolet resistance and high temperature resistance, can improve the afterimage defect and has high performance⊥And/delta, the transmittance of the liquid crystal display panel can be effectively improved.
Claims (9)
1. A liquid crystal composition comprising one or more compounds of formula I, one or more compounds of formula II, and one or more compounds of formula III,
in the formula I, Z1Represents an alkylene group having 1 to 20 carbon atoms in which any one or more H atoms are optionally substituted by halogen, any one or more non-adjacent-CH2-optionally substituted by-O-;
in the formula II, R represents alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms or alkenyloxy with 3-8 carbon atoms;
in the formula III, R1Representing a carbon number of 1 to 10An alkyl group, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and p represents 0 or 1.
2. The liquid crystal composition of claim 1, further comprising one or more compounds of formula IV,
in the formula IV, R2、R3Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
3. The liquid crystal composition according to any of claims 1 or 2, further comprising one or more compounds of the formula V,
in formula V, R4Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R4Any one or more-CH of the groups shown2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z2Represents a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
X1、X2each independently represents a H atom or a F atom; x3Represents a H atom, a F atom or a methyl group;
Y1represents-F, -CF3、-OCF3、-OCF2H or-OCH2F；
m represents 0, 1 or 2.
4. A liquid-crystal composition according to any one of claims 1 to 3, further comprising one or more compounds of the formula VI,
in formula VI, R5、R6Each independently represents an alkyl group having 1 to 10 carbon atoms, an 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;
5. The liquid crystal composition according to any one of claims 1 to 4, further comprising one or more compounds represented by the following formula VII,
in the formula VII, R7、R8Each independently represents an alkyl group having 1 to 10 carbon atoms, an 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;
F1、F2、F3Each independently represents a H atom or a F atom, and F2、F3Not simultaneously being F atoms.
6. The liquid crystal composition according to any one of claims 1 to 5, further comprising one or more compounds represented by the following formula VIII,
in the formula VIII, R9、R10Each independently represents an alkyl group having 1 to 10 carbon atoms, an 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 R9、R10Any one or more non-adjacent-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z3represents a single bond, -CF2O-、-CH2CH2-or-CH2O-；
Z4Represents a single bond, -CH2CH2-or-CH2O-；
q represents 1 or 2;
n represents 0, 1 or 2.
7. The liquid crystal composition of any one of claims 1 to 6, further comprising one or more compounds of formula IX,
in the formula IX, R11、R12Each 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 R11、R12Any one or more non-adjacent-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
w represents-O-, -S-or-CH2O-。
8. A liquid crystal display element or a liquid crystal display comprising the liquid crystal composition according to any one of claims 1 to 7, the display element or display being an active matrix display element or a passive matrix display element, the display being an active matrix display or a passive matrix display.
9. The liquid crystal display element or the liquid crystal display according to claim 8, wherein the liquid crystal display element or the liquid crystal display comprises an alignment layer formed of a PI with a medium-high resistivity.
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| CN103937508A (en) * | 2014-04-28 | 2014-07-23 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition with stable threshold voltage and application thereof |
| US20180148649A1 (en) * | 2016-11-29 | 2018-05-31 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
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