CN109880639B - 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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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 175
- 239000000203 mixture Substances 0.000 title claims abstract description 172
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims description 116
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- -1 fluoro 1, 4-phenylene Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000004044 response Effects 0.000 abstract description 13
- 239000000654 additive Substances 0.000 abstract description 7
- 230000000996 additive effect Effects 0.000 abstract description 5
- 230000003287 optical effect Effects 0.000 abstract description 4
- 230000000875 corresponding effect Effects 0.000 description 52
- 238000009472 formulation Methods 0.000 description 50
- 238000012360 testing method Methods 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 16
- 230000032683 aging Effects 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 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
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
-
- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/062—Non-steroidal liquid crystal compounds containing one non-condensed benzene ring
-
- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
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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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The disclosure relates to a liquid crystal composition, a liquid crystal display element comprising the liquid crystal composition and a liquid crystal display, and belongs to the field of liquid crystal display. The disclosed liquid crystal composition, which comprises at least one compound represented by formula I as an additive and one or more compounds represented by formula II, has a high Clearing Point (CP), suitable optical anisotropy (Δ n), a fast response speed, high stability to ultraviolet light, and high stability to heat.
Description
Technical Field
The present disclosure relates to a liquid crystal composition, and more particularly, to a liquid crystal composition, a liquid crystal display element including the liquid crystal composition, and a liquid crystal display.
Background
Liquid crystal display elements are classified into the following modes according to display modes: twisted Nematic (TN) mode, Super Twisted Nematic (STN) mode, in-plane mode (IPS), Vertical Alignment (VA) mode. The following properties are required for the liquid crystal composition regardless of the display mode:
(1) the chemical and physical properties are stable; (2) the viscosity is low; (3) has a suitable dielectric Δ; (4) suitable refractive indices Δ n; (5) the mutual solubility with other liquid crystal compounds is good.
Early commercial TFT-LCD products basically adopted the TN display mode, and the biggest problem thereof was the narrow viewing angle. With the increase in the size of products, particularly in the application to the TV field, IPS display modes and VA display modes having a wide viewing angle characteristic are developed and applied in sequence.
However, liquid crystal media used for display elements such as FFS mode, IPS mode, and VA mode are not perfect, and liquid crystal materials used for display devices are required to have (i) low driving voltage: the liquid crystal material has proper negative dielectric anisotropy; quick response: the liquid crystal material has proper optical anisotropy; high reliability: high charge retention rate, high specific resistance value, excellent high-temperature stability, strict requirements on the stability of UV light or irradiation by conventional backlight illumination and the like. However, when the basic characteristics (low driving voltage, fast response) required by our liquid crystal material are achieved, the reliability problem is exposed, especially the stability of UV light is deteriorated. Therefore, it is a troublesome problem to solve the reliability of such liquid crystal media, in other words, we have demanded to invent or propose one or more compounds for improving the stability of the liquid crystal media to solve the reliability problem of the liquid crystal media.
Disclosure of Invention
The present inventors have conducted extensive studies in order to solve the problems of the prior art, and as a result, surprisingly found that the UV light stability can be improved when the liquid crystal composition is applied to a liquid crystal display element by using a combination of the compound represented by the formula I as an additive and the compound represented by the formula II, and the present disclosure has been completed.
In addition, the liquid crystal composition of the present disclosure also has a high Clearing Point (CP), suitable optical anisotropy (Δ n), fast response speed, and high stability to heat.
Another object of the present disclosure is to provide a liquid crystal display device comprising the liquid crystal composition of the present disclosure, which has a fast response speed.
It is still another object of the present disclosure to provide a liquid crystal display comprising the liquid crystal composition of the present disclosure, which has a fast response speed.
In order to achieve the purpose, the following technical scheme is adopted in the disclosure:
the present disclosure provides liquid crystal compositions comprising at least one compound of formula I as an additive, and one or more compounds of formula II,
in the formula I, Z1Represents an alkylene group having 1 to 20 carbon atoms, wherein any one or more hydrogen atoms in the alkylene group are optionally substituted by halogen, and any one or more-CH groups2-optionally substituted by-O-;
in the formula II, R1、R2One of them represents an alkyl group having 1 to 10 carbon atoms, and the other represents an alkenyl group having 2 to 10 carbon atoms.
The present disclosure also provides a liquid crystal display element comprising the liquid crystal composition of the present disclosure, the liquid crystal display element being an active matrix addressing display element or a passive matrix addressing display element.
The present disclosure also provides a liquid crystal display comprising the liquid crystal composition of the present disclosure, the liquid crystal display being an active matrix addressed display or a passive matrix addressed display.
Detailed Description
[ liquid Crystal composition ]
The liquid crystal composition disclosed by the invention comprises at least one compound shown as a formula I and one or more compounds shown as a formula II,
in the formula I, Z1Represents an alkylene group having 1 to 20 carbon atoms, wherein at least one hydrogen in the alkylene group is substituted by a halogen atom and at least one-CH2-may be substituted by-O-;
in the formula II, R1、R2One of them represents a carbon atom number of 1 &10 is an alkyl group, and the other represents an alkenyl group having 2 to 10 carbon atoms.
Z of the foregoing1The alkylene group having 1 to 20 carbon atoms may be a straight chain or a branched chain. In addition, the aforementioned alkylene group optionally has a ring structure. The alkylene group is preferably a linear structure.
Examples of the alkyl group having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, and the like.
Examples of the alkenyl group having 2 to 10 carbon atoms include a vinyl group, a 1-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 2-hexenyl group, and a 3-hexenyl group.
In the liquid crystal composition of the present disclosure, preferably, the compound represented by the aforementioned formula I is selected from the group consisting of compounds represented by the following formulae I-1 to I-6:
in the liquid crystal composition of the present disclosure, it is further preferred that the compound represented by the aforementioned formula I is selected from the group consisting of compounds represented by the following formulae I-5 to I-6:
in the liquid crystal composition of the present disclosure, preferably, the compound represented by the above formula ii is selected from the group consisting of compounds represented by the following formulae ii-1 to ii-5:
in the liquid crystal composition of the present disclosure, it is further preferred that the compound represented by the above formula ii is selected from the group consisting of compounds represented by the following formulae ii-1 to ii-2:
in the liquid crystal composition of the present disclosure, the compound represented by the formula I is used as an additive, and the additive is a light stabilizer. The compound shown in the formula I has a blocking amine, and the blocking amine can generate nitroxide free radicals through oxidation of peroxy radicals, and the nitroxide free radicals can capture both hydrocarbyl free radicals and peroxy radicals, so that the compound has an antioxidation effect. Preferably, the content of the compound represented by the aforementioned formula i is 0.001% to 1%, preferably 0.005% to 0.2%, based on 100% by mass of the total of the components other than the additives.
In the liquid crystal composition of the present disclosure, the total content by mass of the compound represented by the formula ii is 1% to 54%, preferably 1% to 20%, with respect to the total of the components other than the additives.
The liquid crystal composition of the present disclosure optionally further comprises one or more compounds represented by formula iii:
wherein:
R3、R4each 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;
R3、R4any one or more of the groups shownA non-connected CH2Optionally substituted with cyclopentyl, cyclobutyl, or cyclopropyl;
Z2、Z3each independently represents a single bond, -CH2CH2-or-CH2O-；
m and n each independently represent 0, 1 or 2 and m + n.ltoreq.2.
In the liquid crystal composition of the present disclosure, preferably, the compound represented by the aforementioned formula iii is selected from the group consisting of compounds represented by the following formulae iii-1 to iii-14:
wherein:
R31、R41each 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;
R31、R41any one or more unconnected CH in the group shown2Optionally substituted with cyclopentyl, cyclobutyl or cyclopropyl.
The liquid crystal compositions of the present disclosure preferably further comprise one or more compounds of formula iv:
wherein,
R5、R6each 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, or a fluorine-substituted alkenyl group having 2 to 10 carbon atoms;
The liquid crystal composition of the present disclosure, preferably, the compound represented by the aforementioned formula iv is selected from the group consisting of compounds represented by the following formulae iv-1 to iv-3:
wherein,
R5、R6represents 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, or a fluorine-substituted alkenyl group having 2 to 10 carbon atoms.
The liquid crystal composition of the present disclosure preferably further comprises one or more compounds represented by formula v:
in the formula V, R7、R8Each 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, or an alkenyl group having 2 to 10 carbon atomsA fluorine-substituted alkenyl group having 2 to 10 carbon atoms;
In the liquid crystal composition of the present disclosure, preferably, the compound represented by the aforementioned formula v is selected from the group consisting of compounds represented by the following formulas v-1 to v-3:
in the formulae V-1 and V-2, R7、R8Each 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, or a fluorine-substituted alkenyl group having 2 to 10 carbon atoms;
in the formula V-3, R7、R8Each 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, or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms.
The liquid crystal composition of the present disclosure preferably further comprises one or more compounds represented by formula vi:
in the formula IV, R9Represents 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, or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, any one or more of these groups being non-connected CH2Optionally substituted with cyclopentyl, cyclobutyl, or cyclopropyl;
R10represents an alkyl group having 1 to 10 atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms;
x represents O or S.
The liquid crystal composition of the present disclosure preferably has the compound represented by the aforementioned formula vi selected from the group consisting of compounds represented by the following formulae vi-1 to vi-12:
wherein R is91、R101Each independently represents an alkyl group having 1 to 10 carbon atoms.
The liquid crystal composition of the present disclosure preferably further comprises one or more compounds represented by formula vii:
in the formula VII, R11Represents an alkyl group having 1 to 10 carbon atoms, and R11Any one or more unconnected CH in the group shown2Optionally substituted with cyclopentyl, cyclobutyl, or cyclopropyl;
m represents 1 or 2, and when m represents 2,
optionally the same or different.
The liquid crystal composition of the present disclosure, preferably, the compound represented by the aforementioned formula VII is selected from the group consisting of compounds represented by the following formulae VII-1 to VII-8:
wherein R is111Represents an alkyl group having 1 to 10 carbon atoms.
The liquid crystal composition of the present disclosure preferably further comprises one or more compounds represented by formula viii:
in the formula VIII, the compound represented by the formula,
R12represents an alkyl group having 1 to 10 carbon atoms; y is1Represents F, or, -OCF3(ii) a (F) Represents F or H;
p represents 1 or 2, and when p represents 2
May be the same or different.
The liquid crystal composition of the present disclosure, preferably, the compound represented by the aforementioned formula viii is selected from the group consisting of compounds represented by the following formulae viii-1 to viii-5:
wherein R is121Represents an alkyl group having 1 to 10 carbon atoms; (F) represents F or H.
The liquid crystal composition of the present disclosure preferably further comprises one or more compounds represented by formula ix:
in the formula IX, R13Represents an alkyl group having 1 to 10 carbon atoms, and R13Any one or more unconnected CH in the group shown2Optionally substituted with cyclopentyl, cyclobutyl, or cyclopropyl;
Y2represents an alkyl group having 1 to 10 carbon atoms or F;
The liquid crystal composition of the present disclosure, preferably, the aforementioned compound represented by the formula IX is selected from the group consisting of compounds represented by the following formulae IX-1 to IX-4:
R131represents an alkyl group having 1 to 10 carbon atoms; y is2Represents an alkyl group having 1 to 10 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 1.5% 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 ultraviolet absorber include,
t represents an integer of 1 to 10.
[ liquid Crystal display element or liquid Crystal display ]
The present disclosure also relates to a liquid crystal display element or a liquid crystal display comprising any of the above liquid crystal compositions; the display element or display is an active matrix display element or display or a passive matrix display element or display.
Optionally, the liquid crystal display element or the liquid crystal display is preferably an active matrix liquid crystal display element or a liquid crystal display.
Optionally, the active matrix display element or display is a PSVA-TFT liquid crystal display element or display.
The liquid crystal display element or the liquid crystal display comprising the compound or the liquid crystal composition has a wider nematic phase temperature range, a faster response speed and a lower cell thickness.
Examples
In order to more clearly illustrate the disclosure, the disclosure 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 present disclosure.
In this specification, unless otherwise specified, the percentages refer to mass percentages, temperatures are in degrees centigrade (° 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;
Δ n represents optical anisotropy, noRefractive 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∥is the dielectric constant parallel to the molecular axis,⊥dielectric constant perpendicular to the molecular axis, at 25 + -0.5 deg.C, 20 μm parallel box, 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;
k11 is a torsional elastic constant, K33 is a splay elastic constant, and the test conditions are as follows: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
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;
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 most of 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 of the embodiment of the disclosure 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.
Corresponding code of the ring structure of Table 1
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
Comparative example 1
The formulation and corresponding properties of the liquid crystal compositions are shown in table 4 below.
TABLE 4 formulation and corresponding Properties of the comparative example 1 liquid Crystal composition
The CPP-3-2V1 in example 1 was replaced with CPP-3-2 and CPP1V-2 with CPP-5-2, and the rest was the same as in example 1 as comparative example 1. Example 1 has a large refractive index, a high clearing point, less γ 1/K33, and a faster response than comparative example 1. Thus, the liquid crystal composition of the present disclosure using the combination of the compound represented by formula I and the compound represented by formula II can be used for developing a low cell thickness, fast response liquid crystal display.
Example 2
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 2
Comparative example 2
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 comparative example 2
CPP-3-2V1 in example 2 was replaced with CPP-3-2, and the remainder was the same as in example 2, as comparative example 2. Example 2 has a large refractive index, a high clearing point, less γ 1/K33, and a faster response than comparative example 2. Thus, the liquid crystal composition of the present disclosure using the combination of the compound represented by formula I and the compound represented by formula II can be used for developing a low cell thickness, fast response liquid crystal display.
Example 3
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 3
Example 4
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 4
Comparative example 3
The formulation and corresponding properties of the liquid crystal compositions are shown in table 9 below.
TABLE 9 formulation and corresponding Properties of comparative example 3 liquid Crystal composition
The CPP-1V-2 in example 4 was replaced with CPP-3-2 and CPP-3-2V1 was replaced with CPP-5-2, and the rest was the same as in example 4 as comparative example 3. Example 4 has a large refractive index, a high clearing point, less γ 1/K33, and a faster response than comparative example 3. Thus, the liquid crystal composition of the present disclosure using the combination of the compound represented by formula I and the compound represented by formula II can be used for developing a low cell thickness, fast response liquid crystal display.
Example 5
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 5
Example 6
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 example 6
Example 7
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 example 7
Example 8
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 example 8
Example 9
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 example 9
Example 10
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 15 below.
TABLE 15 formulation and corresponding Properties of the liquid crystal composition of example 10
Example 11
The formulation of the liquid crystal composition and the corresponding properties are shown in Table 16 below.
TABLE 16 formulation and corresponding Properties of the liquid crystal composition of example 11
Example 12
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 17 below.
TABLE 17 formulation and corresponding Properties of the liquid crystal composition of example 12
Example 13
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 18 below.
TABLE 18 formulation and corresponding Properties of the liquid crystal composition of example 13
Example 14
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 19 below.
TABLE 19 formulation and corresponding Properties of the liquid crystal composition of example 14
Example 15
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 20 below.
TABLE 20 formulation and corresponding Properties of the liquid crystal composition of example 15
Example 16
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 21 below.
TABLE 21 formulation and corresponding Properties of the liquid crystal composition of example 16
Example 17
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 22 below.
TABLE 22 formulation and corresponding Properties of the liquid crystal composition of example 17
Example 18
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 23 below.
TABLE 23 formulation and corresponding Properties of the liquid crystal composition of example 18
Example 19
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 24 below.
TABLE 24 formulation and corresponding Properties of the liquid crystal composition of example 19
Example 20
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 25 below.
TABLE 25 formulation and corresponding Properties of the liquid crystal composition of example 20
Example 21
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 26 below.
TABLE 26 formulation and corresponding Properties of the liquid crystal composition of example 21
Example 22
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 27 below.
TABLE 27 formulation and corresponding Properties of the liquid crystal composition of example 22
TABLE 28 reliability data of examples and comparative examples
The reliability of the liquid crystal composition is tested by ultraviolet and high temperature aging tests and VHR tests, and the smaller the VHR data change before and after the ultraviolet and high temperature tests of the liquid crystal composition is, the stronger the ultraviolet and high temperature resistance is. Therefore, the ultraviolet and high temperature resistance was judged by comparing the difference between the VHR data before and after the test in each of examples and comparative examples.
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.
Ultraviolet aging test: the liquid crystal composition was irradiated with 5000mJ energy under an ultraviolet lamp having a wavelength of 365 nm.
High-temperature aging test: the liquid crystal composition was placed in an oven at 100 ℃ for one hour.
The smaller the change of the VHR data after the aging test relative to the initial VHR data, the stronger the ultraviolet and high temperature resistance of the liquid crystal composition is, so that the stronger the resistance of the liquid crystal composition to the external environment during the working process can be judged, and therefore, the higher the reliability of the liquid crystal composition is.
In addition, the liquid crystal compositions of examples and comparative examples were poured into a liquid crystal cell and an afterimage test was performed, and the test results are shown in table 28.
As can be seen from Table 28, the liquid crystal composition of the present invention using the combination of the compounds represented by formula I and the compounds represented by formula II is very significant in improving the UV and high temperature resistance of the liquid crystal material, and the liquid crystal composition of the present invention has good UV and high temperature resistance, compared to the comparative example not using the combination of the compounds represented by formula I and the compounds represented by formula II.
It should be understood that the above-mentioned examples are for illustrative purposes only and are not intended to limit the embodiments of the present disclosure, and that various other modifications and changes in light thereof will be suggested to persons skilled in the art and are not intended to be exhaustive or to limit the present disclosure to the precise embodiments disclosed herein.
Claims (10)
1. A liquid crystal composition, characterized in that the liquid crystal composition comprises at least one compound shown as a formula I and one or more compounds shown as a formula II,
in the formula I, Z1Represents an alkylene group having 1 to 6 or 10 to 20 carbon atoms, any of the alkylene groupsMeaning that one or more hydrogens are optionally substituted with halogen, any one or more-CH2-optionally substituted by-O-; the total amount of the components except the compound shown in the formula I is 100 percent by mass, and the content of the compound shown in the formula I is 0.001 to 0.2 percent;
in the formula II, R1Represents an alkyl group having 1 to 10 carbon atoms, R2An alkenyl group having 2 to 10 carbon atoms; the total amount of the components except the compound shown in the formula I is 100 mass%, and the content of the compound shown in the formula II is 1-20%.
2. The liquid crystal composition of claim 1, further comprising one or more compounds of formula III,
in the formula III, R3、R4Each 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;
R3、R4any one or more unconnected CH in the group shown2Optionally substituted with cyclopentyl, cyclobutyl, or cyclopropyl;
Z2、Z3each independently represents a single bond, -CH2CH2-or-CH2O-；
m and n each independently represent 0, 1 or 2 and m + n.ltoreq.2.
3. The liquid crystal composition of claim 2, wherein the one or more compounds of formula iii are selected from the group consisting of compounds of formulae iii-1 to iii-14 as follows:
wherein:
R31、R41each 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;
R31、R41any one or more unconnected CH in the group shown2Optionally substituted with cyclopentyl, cyclobutyl or cyclopropyl.
4. The liquid crystal composition of any one of claims 1 to 3, further comprising one or more compounds of formula IV:
in the formula IV, R5、R6Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, or a C1 to C10An alkoxy group having 1 to 10 carbon atoms substituted with fluorine, an alkenyl group having 2 to 10 carbon atoms, or an alkenyl group having 2 to 10 carbon atoms substituted with fluorine;
5. The liquid crystal composition of any one of claims 1 to 3, further comprising one or more compounds of formula V:
in formula V, R7 、R8Each 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, or a fluorine-substituted alkenyl group having 2 to 10 carbon atoms;
6. The liquid crystal composition of any one of claims 1 to 3, further comprising one or more compounds of formula VI:
in formula VI, R9Represents 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, or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, R9Any one or more unconnected CH in the group shown2Optionally substituted with cyclopentyl, cyclobutyl, or cyclopropyl;
R10represents an alkyl group having 1 to 10 atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a fluorine-substituted alkoxy group having 1 to 10 carbon atoms;
x represents O or S.
7. The liquid crystal composition according to any of claims 1 to 3, further comprising one or more compounds of formula VII,
in the formula VII, R11Represents an alkyl group having 1 to 10 carbon atoms, and R11Any one or more unconnected CH in the group shown2Optionally substituted with cyclopentyl, cyclobutyl, or cyclopropyl;
m represents 1 or 2, and when m represents 2,
optionally the same or different.
8. The liquid crystal composition of any one of claims 1 to 3, further comprising one or more compounds of formula VIII,
in the formula VIII, R12Represents an alkyl group having 1 to 10 carbon atoms; y is1Represents F, or, -OCF3(ii) a (F) Represents F or H;
p represents 1 or 2, and when p represents 2
Optionally the same or different.
9. The liquid crystal composition according to any one of claims 1 to 3, further comprising one or more compounds of formula IX,
in the formula IX, R13Represents an alkyl group having 1 to 10 carbon atoms, and R13Any one or more unconnected CH in the group shown2Optionally substituted with cyclopentyl, cyclobutyl, or cyclopropyl;
Y2represents an alkyl group having 1 to 10 carbon atoms or F;
10. a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition according to any one of claims 1 to 9, wherein the liquid crystal display element or the liquid crystal display is an active matrix addressing display element or a display, or a passive matrix addressing display element or a display.
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| CN111040776B (en) * | 2018-10-12 | 2023-04-07 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN112048315B (en) * | 2019-06-06 | 2022-08-05 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device |
| CN112048318B (en) * | 2019-06-06 | 2023-03-31 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
| CN112980457A (en) * | 2019-12-02 | 2021-06-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound, liquid crystal composition, liquid crystal display element, or liquid crystal display |
| CN112940753B (en) * | 2019-12-30 | 2023-07-07 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element or liquid crystal display |
| CN113122276B (en) * | 2019-12-30 | 2023-10-03 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN113122273B (en) * | 2019-12-30 | 2024-05-31 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN112980464A (en) * | 2019-12-30 | 2021-06-18 | 石家庄诚志永华显示材料有限公司 | Negative liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN112980462A (en) * | 2019-12-30 | 2021-06-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN113122272B (en) * | 2019-12-30 | 2024-08-09 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN112961683B (en) * | 2019-12-30 | 2023-07-07 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN112940739A (en) * | 2019-12-30 | 2021-06-11 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN112940754B (en) * | 2019-12-30 | 2023-07-07 | 石家庄诚志永华显示材料有限公司 | Negative liquid crystal composition, liquid crystal display element and liquid crystal display |
| WO2021253621A1 (en) * | 2020-06-16 | 2021-12-23 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element, and liquid crystal display |
| CN113801663B (en) * | 2020-06-16 | 2024-05-31 | 石家庄诚志永华显示材料有限公司 | Negative liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN113046095A (en) * | 2021-03-05 | 2021-06-29 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element or liquid crystal display |
| CN113234448B (en) * | 2021-03-31 | 2024-10-01 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition, liquid crystal display element and liquid crystal display |
| CN113583684A (en) * | 2021-09-07 | 2021-11-02 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and liquid crystal display device |
| CN114265245B (en) * | 2021-11-18 | 2024-04-02 | 浙江晨泰科技股份有限公司 | Smart electric meter display device |
| CN117004409A (en) * | 2023-07-31 | 2023-11-07 | 河北化工医药职业技术学院 | Liquid crystal additive, preparation method thereof, liquid crystal composition, display element and display |
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