CN113429980B - Display material with good low-temperature stability - Google Patents
Display material with good low-temperature stability Download PDFInfo
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- CN113429980B CN113429980B CN202110630837.4A CN202110630837A CN113429980B CN 113429980 B CN113429980 B CN 113429980B CN 202110630837 A CN202110630837 A CN 202110630837A CN 113429980 B CN113429980 B CN 113429980B
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- 239000012769 display material Substances 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 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 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 101100112111 Caenorhabditis elegans cand-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
-
- 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
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Disclosed is a display material comprising at least one compound of formula I, at least one compound of formula II, and at least one compound of formula III. Combinations of different monomers using specific proportions and specific structures, in particular specific cyclic units and pendant groups; compared with the prior art, the low-temperature stability of the display material is better.
Description
Technical Field
The invention belongs to the technical field of display materials, and particularly relates to a display material with good low-temperature stability.
Background
With the rapid development of economy and the improvement of the living standard of people, automobiles have become the main transportation means of ordinary families. As a device for reflecting the operation conditions of various systems of an automobile, an automobile instrument panel is one of the most commonly contacted automobile parts. Conventionally, the rotation speed, the water temperature, the oil quantity and the speed per hour are displayed by a mechanical instrument panel. The mechanical instrument panel has the characteristics of stable technology, maturity and reliability.
However, in recent years, due to the rapid development of automobile, communication and display technologies, more intuitive and modern display devices are required to meet the demands of instant messaging, navigation and entertainment of people, so that all-liquid-crystal dashboards are desired. The novel instrument panel is applied to automobiles to replace the traditional mechanical instrument panel by the characteristics of light weight, low power consumption and colored flowers, realizes a digital display function and is used for displaying the average oil consumption, the instantaneous oil consumption, the outdoor temperature, the average speed, the driving time, the driving mileage, the navigation and the multimedia entertainment of the automobiles. The full liquid crystal instrument panel is safer in driving; the display effect is better, and the sense of science and technology is stronger.
As a liquid crystal display device of an automobile instrument panel, display modes such as TN (twisted nematic), STN (super twisted nematic) and VA (vertical alignment) are more commonly used. The TN and STN display modes have short response times and wide operating temperatures, but the contrast and viewing angle are not ideal. VA display mode has the characteristics of a wide viewing angle and a high contrast ratio, but is easy to crystallize or to develop a smectic phase at a low temperature, while the low temperature response time is slightly long.
Accordingly, there is an urgent need to provide a display material having good low temperature stability against the above-mentioned drawbacks of the prior art.
Disclosure of Invention
The invention aims to provide a display material with good low-temperature stability. Compared with the prior art, the display material has better low-temperature stability.
In order to solve the technical problems, the invention adopts the following technical scheme: a display material comprising at least one compound of formula I, at least one compound of formula II and at least one compound of formula III,
wherein R is 1 And R is 2 Each independently represents an alkyl or alkoxy group of 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms;
wherein R is 3 And R is 4 Each independently represents an alkyl or alkoxy group of 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms;
wherein R is 5 Represents alkenyl of 2 to 8 carbon atoms, preferably 2 to 6 carbon atoms; r is R 6 Represents alkyl or alkoxy groups of 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms.
In the present invention, alkenyl groups are defined as one or more non-adjacent CH' s 2 Alkyl substituted with ch=ch.
The display material according to the invention, wherein the compound of formula I is present in an amount of 6-14%, preferably 8-12%; the content of the compound of formula II is 6-12%, preferably 8-10%; the content of the compound of formula III is 10-20%, preferably 12-18%; based on the total weight of the display material.
The display material according to the invention, wherein it further comprises a compound of formula IV,
wherein R is 7 And R is 8 Each independently represents an alkyl or alkoxy group of 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms.
The display material according to the invention, wherein the compound of formula IV is present in an amount of 4-8%, preferably 5-7%; based on the total weight of the display material.
The display material according to the invention, wherein it further comprises a compound of formula V,
wherein R is 9 Represents alkenyl of 2 to 8 carbon atoms, preferably 2 to 6 carbon atoms; r is R 10 Represents alkyl or alkoxy groups of 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms; ring A represents
The display material according to the invention, wherein the compound of formula V is present in an amount of 4-12%, preferably 6-10%; based on the total weight of the display material.
The display material according to the invention, wherein it further comprises a compound of formula VI,
wherein R is 11 Represents 1-8 carbon atomsSelecting alkyl or alkoxy of 1-6 carbon atoms; r is R 12 Represents alkenyl of 2 to 8 carbon atoms, preferably 2 to 6 carbon atoms.
The display material according to the invention, wherein the compound of formula VI is present in an amount of 22-34%, preferably 26-30%; based on the total weight of the display material.
The display material according to the invention, wherein it further comprises a compound of formula VII,
wherein R is 13 Represents alkenyl of 2 to 8 carbon atoms, preferably 2 to 6 carbon atoms; r is R 14 Represents alkyl or alkoxy groups of 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms.
The display material according to the invention, wherein the compound of formula VII is present in an amount of 10-18%, preferably 12-15%; based on the total weight of the display material.
The display material according to the invention, wherein it further comprises a compound of formula VIII,
wherein R is 15 And R is 16 Each independently represents an alkyl or alkoxy group of 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms.
The display material according to the invention, wherein the compound of formula VIII is present in an amount of 4-9%, preferably 5-8%; based on the total weight of the display material.
In a further preferred embodiment, the display material according to the invention advantageously consists of the compounds of the formulae I to VIII described above.
The inventors have found that the use of different monomers in combination in specific proportions and in specific structures, in particular in specific cyclic units and side groups, results in a display material for an all-liquid-crystal instrument panel of a motor vehicle. Compared with the prior art, the display material has better low-temperature stability.
Detailed Description
The invention is further described below in conjunction with the detailed description.
It should be understood that the description of the specific embodiments is merely illustrative of the principles and spirit of the invention, and not in limitation thereof. Further, it should be understood that various changes, substitutions, omissions, modifications, or adaptations to the present invention may be made by those skilled in the art after having read the present disclosure, and such equivalent embodiments are within the scope of the present invention as defined in the appended claims.
In the present invention, all parts are parts by weight unless otherwise specified; all percentages are by weight; cp represents a clearing point in degrees Celsius.
Δn represents the optical anisotropy value at 25℃and 589 nm.
Delta epsilon represents the dielectric anisotropy values obtained for a 6 μm thick VA test cell at 25℃and 1 kHz.
γ1 represents the rotational viscosity (mPas) measured at 25 ℃.
In the present invention, each monomer compound is represented by a three-stage abbreviation of (cyclic unit+linker) +left side group+right side group. Wherein,,
linking and pendant groups:
n(O)-＝C n H 2n+1 (O)-；
-(O)n＝-(O)C n H 2n+1 ；
Vn-＝CH 2 ＝CHC n H 2n -；
-nV＝-C n H 2n CH＝CH 2 ；
-V＝-CH＝CH 2 ；
-V-＝-CH＝CH-；
-T-＝-C≡C-；
-1O-＝-CH 2 O-；
-Q-＝-CF 2 O-；
n＝C n H 2n+1 ；
n=natural number;
o represents an oxygen atom.
A ring unit:
example 1
Δn＝0.097；Δε＝-4.2；Cp＝81.9；γ1＝84。
Example 2
Example 3
Further, in order to test the low temperature stability of example 1, a 6 μm thick VA test cell (the inner surfaces of the upper and lower substrates having polyimide PI alignment layers) for an automobile all-liquid-crystal instrument panel was filled with a display material, and placed in a refrigerator at-20 ℃ to observe whether crystallization or smectic phase occurs in the VA test cell at regular intervals, and the duration of the low temperature stability, that is, the last time the phase stability was observed (LTS, h) was determined.
On the other hand, the response time (τ, ms) is the sum of the rise time and fall time of the VA test cell at-20deg.C and 6V drive voltage; the former is defined as the time for which the transmittance rises from 10% of the maximum transmittance until 90% is reached; the latter is the time when the transmittance decreases from 90% of the maximum transmittance until reaching 10%.
The results are shown in Table 1.
TABLE 1
| Test box | LTS，h | Response time (τ, ms) |
| Example 1 | >1300h | 12.83 |
As can be seen from Table 1, the display material of example 1 of the present invention is better in low temperature stability.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention are included in the protection scope of the present invention.
Claims (2)
1. A display material comprising at least one compound of formula I, at least one compound of formula II and at least one compound of formula III, and at least one compound of formula IV, at least one compound of formula V, at least one VI, at least one compound of formula VII, and at least one compound of VIII;
the content of the compound of the formula I is 8-12%; the content of the compound II is 8-10%; the content of the compound of the formula III is 12-18%; the content of the compound of the formula IV is 5-7%; the content of the compound of formula V is 6-10%; the content of the compound of the formula VI is 26-30%; the content of the compound of the formula VII is 12-15%, and the content of the compound of the formula VIII is 5-8%; based on the total weight of the host mixture;
wherein R is 1 And R is 2 Each independently represents an alkyl group of 1 to 8 carbon atoms or an alkoxy group;
wherein R is 3 And R is 4 Each independently represents an alkyl group of 1 to 8 carbon atoms or an alkoxy group;
wherein R is 5 Represents alkenyl of 2 to 8 carbon atoms; r is R 6 Represents alkyl or alkoxy of 1 to 8 carbon atoms;
wherein R is 7 And R is 8 Each independently represents an alkyl group of 1 to 8 carbon atoms or an alkoxy group;
wherein R is 9 Represents alkenyl of 2 to 8 carbon atoms; r is R 10 Represents alkyl or alkoxy of 1 to 8 carbon atoms; ring A represents
Wherein R is 11 Represents alkyl or alkoxy of 1 to 8 carbon atoms; r is R 12 Represents alkenyl of 2 to 8 carbon atoms;
wherein R is 13 Represents alkenyl of 2 to 8 carbon atoms; r is R 14 Represents alkyl or alkoxy of 1 to 8 carbon atoms;
wherein R is 15 And R is 16 Each independently represents an alkyl group or an alkoxy group of 1 to 8 carbon atoms.
2. The display material of claim 1, wherein R 1 And R is 2 Each independently represents an alkyl group of 1 to 6 carbon atoms or an alkoxy group; r is R 3 And R is 4 Each independently represents an alkyl group of 1 to 6 carbon atoms or an alkoxy group; r is R 5 Represents alkenyl of 2 to 6 carbon atoms; r is R 6 Represents an alkyl or alkoxy group of 1 to 6 carbon atoms; r is R 7 And R is 8 Each independently represents an alkyl group of 1 to 6 carbon atoms or an alkoxy group; r is R 9 Represents alkenyl of 2 to 6 carbon atoms; r is R 10 Represents an alkyl or alkoxy group of 1 to 6 carbon atoms; r is R 11 Represents an alkyl or alkoxy group of 1 to 6 carbon atoms; r is R 12 Represents alkenyl of 2 to 6 carbon atoms; r is R 13 Represents alkenyl of 2 to 6 carbon atoms; r is R 14 Represents an alkyl or alkoxy group of 1 to 6 carbon atoms; r is R 15 And R is 16 Each independently represents an alkyl group or an alkoxy group of 1 to 6 carbon atoms.
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| CN113429980B true CN113429980B (en) | 2023-09-26 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012077201A (en) * | 2010-10-01 | 2012-04-19 | Dic Corp | Nematic liquid crystal composition and liquid crystal display element using the same |
| CN107142115A (en) * | 2015-02-15 | 2017-09-08 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropy liquid crystal medium and its application containing cyclopropyl |
| CN108728116A (en) * | 2017-04-18 | 2018-11-02 | 江苏和成显示科技有限公司 | A kind of liquid-crystal composition and its display device |
| WO2019021838A1 (en) * | 2017-07-25 | 2019-01-31 | Dic株式会社 | Liquid crystal composition and liquid crystal display device |
| CN111484858A (en) * | 2019-01-29 | 2020-08-04 | 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 |
| CN111484857A (en) * | 2019-01-29 | 2020-08-04 | 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 |
-
2021
- 2021-06-07 CN CN202110630837.4A patent/CN113429980B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012077201A (en) * | 2010-10-01 | 2012-04-19 | Dic Corp | Nematic liquid crystal composition and liquid crystal display element using the same |
| CN107142115A (en) * | 2015-02-15 | 2017-09-08 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropy liquid crystal medium and its application containing cyclopropyl |
| CN108728116A (en) * | 2017-04-18 | 2018-11-02 | 江苏和成显示科技有限公司 | A kind of liquid-crystal composition and its display device |
| WO2019021838A1 (en) * | 2017-07-25 | 2019-01-31 | Dic株式会社 | Liquid crystal composition and liquid crystal display device |
| CN111484858A (en) * | 2019-01-29 | 2020-08-04 | 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 |
| CN111484857A (en) * | 2019-01-29 | 2020-08-04 | 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 |
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