CN115678572A - Polymerizable liquid crystal composition and liquid crystal display - Google Patents
Polymerizable liquid crystal composition and liquid crystal display Download PDFInfo
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- CN115678572A CN115678572A CN202211137303.9A CN202211137303A CN115678572A CN 115678572 A CN115678572 A CN 115678572A CN 202211137303 A CN202211137303 A CN 202211137303A CN 115678572 A CN115678572 A CN 115678572A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 126
- 239000000203 mixture Substances 0.000 title claims abstract description 108
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 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 description 5
- 125000006850 spacer group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- JXASPPWQHFOWPL-UHFFFAOYSA-N Tamarixin Natural products C1=C(O)C(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 JXASPPWQHFOWPL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000004044 response Effects 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 description 36
- 239000000758 substrate Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
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- Liquid Crystal Substances (AREA)
Abstract
The invention discloses a polymerizable liquid crystal composition and a liquid crystal display, and belongs to the technical field of liquid crystal display. The liquid crystal composition comprises at least one compound shown as a general formula I, at least one compound shown as a general formula P, at least one compound shown as a general formula II and at least one compound shown as a general formula III. The polymerizable liquid crystal composition has the characteristics of less RM residue, stable formed pretilt angle, low rotational viscosity and the like, and can shorten the response time and improve the performance of a liquid crystal display when used as a liquid crystal material.
Description
Technical Field
The invention relates to the technical field of liquid crystal materials, in particular to a polymerizable liquid crystal composition and a liquid crystal display.
Background
Liquid crystal mixtures are widely used in various liquid crystal display devices due to their characteristics such as refractive index anisotropy, dielectric anisotropy, and the like. Among them, VA (vertically aligned) liquid crystals are attracting attention because of their excellent characteristics such as high viewing angle and contrast, but VA liquid crystal displays have certain disadvantages and are a problem of slow response time, and in recent years, a series of VA technologies including MVA, PVA, PSVA and the like have been developed.
The PSVA (polymer stabilized vertical alignment) display technology is that a certain amount of polymerizable liquid crystal compound (RM) is added into a nematic liquid crystal main body, then liquid crystal is filled between two glass substrates with electrodes, a certain voltage is applied, liquid crystal molecules rotate under the action of an electric field to form a certain initial pretilt angle, then ultraviolet irradiation with certain energy is carried out to ensure that polymerizable monomers in the liquid crystal molecules are polymerized to form a cross-linked network, the applied voltage is removed, and the formed pretilt angle is kept due to the left and right of the cross-linked network. In the prior art, after the mixed liquid crystal is irradiated by UV light, a part of the polymerizable monomer is remained, and uncontrolled polymerization occurs under the initiation of environment or backlight in the image display process, so that the pretilt angle of the area is changed, and the transmittance of the area is unexpectedly changed in the process of switching the picture of the liquid crystal display, so that the residual image is generated. Another problem that has been observed in the use of PSVA displays is the stability of the pretilt angle. The reason for this is that the pretilt angle generated by the polymerized RM during the manufacture of the display cannot be maintained constant after a long period of charge and discharge operations, and as a result, the pretilt angle of the liquid crystal display is changed, thereby deteriorating the performance of the liquid crystal display.
Therefore, liquid crystal compositions having the following characteristics are particularly desired: during the UV light irradiation, polymerization of RM in the liquid crystal mixture is controllable, the formed pre-tilt angle is uniform and can be stably maintained, meanwhile, the residue of RM after polymerization is as little as possible, and in addition, the liquid crystal composition has lower rotational viscosity so as to achieve the purpose of reducing the response time.
Disclosure of Invention
The invention aims to provide a polymerizable liquid crystal composition which has the characteristics of less residue of RM, stable formed pretilt angle, low rotational viscosity and the like, can shorten the response time when used as a liquid crystal material, and improves the performance of a liquid crystal display.
In order to solve the technical problems, the invention provides the following technical scheme:
the invention provides a polymerizable liquid crystal composition, which comprises the following components in part by weight:
(1) At least one compound of formula I:
wherein R is A1 Is represented by C 1 -C 12 Alkyl of (C) 1 -C 12 Alkoxy or C 2 -C 12 Alkenyl of (a);
L 1 、L 2 independently of one another, H or-CH 3 ；
Ring A1 and ring A2 independently represent
Ring A3 represents
Or the said
Wherein one or both single bonds are substituted by a double bond;
Z A represents a carbon-carbon single bond, -CH 2 CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CO-O-、-CF 2 CF 2 -or-CF = CF-;
a is 0 or 1;
(2) At least one compound of the general formula P:
wherein ring B1, ring B2 and ring B3 independently represent
Or the said
One or more of H in (a) is/are-F, -Cl or-OCH 3 Substitution;
Z 4 、Z 5 independently of one another, a carbon-carbon single bond, -CH 2 CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CO-O-、CF 2 CF 2 -or-CF = CF-;
b. c are independently of each other an integer from 0 to 4;
P 1 、P 2 represent, independently of each other, a polymerizable group;
Sp 1 、Sp 2 independently of one another, represent a spacer group or a single bond;
(3) At least one compound of formula II:
wherein R is C1 、R C2 Independently of one another represent C 1 -C 12 Alkyl of (C) 1 -C 12 Alkoxy or C 2 -C 12 Alkenyl of (a);
ring C1 and ring C2 independently represent
And at least one of the rings C1 and C2 is
Or the said
At most one H on (a) is substituted by F;
d is 0, 1 or 2; and when d is 2, rings C2 are the same or different;
(4) At least one compound of formula III:
wherein R is D1 、R D2 Independently of one another represent C 1 -C 12 Alkyl of (C) 1 -C 12 Alkoxy or C 2 -C 12 The alkenyl group of (1).
Further, the compound shown in the general formula I is selected from one or more of the following compounds:
in a preferred embodiment of the invention, the compound of formula I is selected from one or more of the following compounds:
in the liquid crystal composition, the content of the compound shown in the general formula I is 1-50% by mass percent. Specifically, the lower limit of the weight percentage of the compound of formula I relative to the total weight of the liquid crystal composition is 1%, 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 16%, 20%, 22%, 24%, or 26%; the upper limit of the weight percentage of the compound of formula I relative to the total weight of the liquid crystal composition is 50%, 48%, 45%, 40%, 38%, 35%, 30%, 28%, 26%, 24%, 20%, 18%, 16%, 15%, 14%, 12% or 10%.
Further, the compound represented by the general formula P is selected from one or more of the following compounds:
wherein Sp represents a spacer group or a single bond.
In a preferred embodiment of the invention, the compound of formula P is selected from one or more of the following compounds:
in the present invention, the compound represented by the general formula P accounts for 0.001 to 5% by weight of the liquid crystal composition, for example, 0.005%, 0.01%, 0.05%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.35%, 0.4%, 0.45%, etc.; preferably, the compound shown in the general formula P accounts for 0.01 to 2 percent of the weight of the liquid crystal composition; further preferably, the compound represented by the general formula P accounts for 0.25 to 0.35 percent of the weight of the liquid crystal composition.
Further, the compound represented by the general formula II is selected from one or more of the following compounds:
in a preferred embodiment of the invention, the compound of formula II is selected from one or more of the following compounds:
in the invention, the proportion of the compound shown in the general formula II in the total mass of the liquid crystal composition is 1-60%. Specifically, the lower limit of the weight percentage of the compound of formula II with respect to the total weight of the liquid crystal composition is 1%, 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 16%, 20%, 22%, 24%, or 26%; the upper limit of the weight percentage of the compound of formula II with respect to the total weight of the liquid crystal composition is 60%, 58%, 56%, 54%, 52%, 50%, 48%, 45%, 40%, 38%, 35%, 30%, 28%, 26%, 24%, 20%, 18%, 16%, 15%, 14%, 12% or 10%.
In a preferred embodiment of the invention, the compound of formula III is selected from one or more of the following compounds:
in the invention, the proportion of the compound shown in the general formula III in the total mass of the liquid crystal composition is 1-60%. Specifically, the lower limit of the weight percentage of the compound of formula III with respect to the total weight of the liquid crystal composition is 1%, 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 16%, 20%, 22%, 24%, or 26%; the upper limit of the weight percentage of the compound of formula III with respect to the total weight of the liquid crystal composition is 60%, 58%, 56%, 54%, 52%, 50%, 48%, 45%, 40%, 38%, 35%, 30%, 28%, 26%, 24%, 20%, 18%, 16%, 15%, 14%, 12% or 10%.
In some embodiments, the polymerizable liquid crystal composition further comprises one or more compounds of formula IV:
wherein R is G1 、R G2 Independently of one another represent C 1 -C 12 Alkyl of (C) 1 -C 12 Alkoxy of (2); or, said C 1 -C 12 Alkyl of (C) 1 -C 12 At least one hydrogen atom in the alkoxy group of (a) is independently substituted by halogen; or, said C 1 -C 12 Alkyl of (C) 1 -C 12 One of alkoxy groups of (2) -CH 2 -or at least two non-adjacent-CHs 2 -independently of each other by-O-, -CH = CH-, -C ≡ C-, -CO-O-or-O-CO-is substituted in a manner not directly linked;
X 1 、X 2 independently of one another denotes-F, -CF 3 。
Further, the polymerizable liquid crystal composition contains the compound of the general formula IV in an amount of 0.1 to 20% by mass, for example, 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, etc. Further preferably, the compound of formula IV accounts for 3-20% of the total weight of the liquid crystal composition.
In a preferred embodiment of the invention, the compound of formula IV is selected from one or more of the following compounds:
in some embodiments of the present invention, the polymerizable liquid crystal composition further comprises one or more compounds represented by formula M:
wherein R is M1 、R M2 Independently of one another represent C 1 -C 12 Alkyl or C 2 -C 12 Alkenyl of (a);
ring M1 and ring M2 independently represent
Z M Represents a carbon-carbon single bond, -CH 2 CH 2 -、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CO-O-、-CF 2 CF 2 -or-CF = CF-;
m is 0, 1 or 2.
The polymerizable liquid crystal composition comprises 1-50% of a compound shown as a general formula M in percentage by mass. Further, the lower limit of the weight percentage of the compound of formula M with respect to the total weight of the liquid crystal composition is 1%, 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 16%, 20%, 22%, 24%, or 26%; the upper limit of the weight percentage of the compound of formula M relative to the total weight of the liquid crystal composition is 50%, 48%, 45%, 40%, 38%, 35%, 30%, 28%, 26%, 24%, 20%, 18%, 16%, 15%, 14%, 12% or 10%.
Further, the compound represented by the general formula M is selected from one or more of the following compounds:
in a preferred embodiment of the invention, the compound of formula M is selected from one or more of the following compounds:
in some embodiments of the present invention, one or more additives, such as stabilizers and the like, are also added to the polymerizable liquid crystal composition.
Preferably, the stabilizer may be selected from one or more of the following compounds:
more preferably, the additive is selected from one or more of the following compounds:
in the above stabilizer compound, n represents an integer of 1 to 12 (e.g., 1, 2,3, 4, 5, 6, 8, 10, or 11).
In the present invention, the amount of the stabilizer is preferably 0 to 5% by weight, more preferably 0 to 1% by weight, and still more preferably 0.01 to 0.2% by weight, based on the total weight of the liquid crystal composition.
The invention also provides a liquid crystal display which comprises the polymerizable liquid crystal composition. Preferably, the liquid crystal display is a VA-type liquid crystal display device such as VA/MVA/PVA/PSVA and/or an IPS, FFS-mode liquid crystal display device; more preferably, the liquid crystal display is an MVA/PVA/PSVA mode liquid crystal display, and even more preferably a PSVA mode liquid crystal display.
Compared with the prior art, the invention has the beneficial effects that:
the polymerizable liquid crystal composition has the characteristics of less RM residue, stable formed pretilt angle, low rotational viscosity and the like, and can shorten the response time and improve the performance of a liquid crystal display when used as a liquid crystal material.
Detailed Description
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
For convenience of expression, in the following examples, the group structures of the liquid crystal compositions are represented by codes listed in Table 1.
TABLE 1
The following compounds are exemplified:
the code of Table 1 is expressed as: 3CPWO2,3 represents cyclohexyl, C represents cyclohexane, P represents-1, 4-diphenyl, W represents 2, 3-difluorobenzene, and 4 represents butyl.
The following steps are repeated:
the code of Table 1 is expressed as: 3CC1OMO1C (5,1V,5O).
The test items in the following examples are abbreviated as follows:
cp (. Degree. C.): clearing point (nematic-isotropic phase transition temperature);
Δ n: refractive index anisotropy (589nm, 25 ℃);
Δ ε: dielectric anisotropy (1KHz, 25 ℃);
t (ms): response time (25 ± 0.5 ℃); liquid crystal was filled between two glass substrates, and measured at t = ton + toff with LCT-5016: ton represents the time required for the relative transmittance to change from 10% to 90%, toff represents the time required for the relative transmittance to change from 90% to 10%;
γ 1 : represents the rotational viscosity [ mPas ] measured at 25 DEG C]Measured in a magnetic field by the spin method;
LTS: the low temperature stable nematic phase transition temperature (measured in a test box, DEG C), the liquid crystal mixture is stored in a glass bottle and stored at low temperature;
K 11 : splay elastic constant (pN, 25 ℃);
K 33 : flexural modulus (pN, 25 ℃);
pretilt angle: the liquid crystal was injected into a test cell with vertical orientation, measured by optipro-micro instrument at 25 ℃.
Wherein Δ ε = ε || -ε ⊥ Wherein epsilon || Is a dielectric constant parallel to the molecular axis,. Epsilon ⊥ For the dielectric constant perpendicular to the molecular axis, test conditions: 25 ℃ and 1KHz.
In each of the following examples and comparative examples, P-1, P-4, P-23, etc. are compounds of the general formula P, and the amount thereof added is relative to the sum (100) of the other components.
Comparative example D1
Liquid crystal is prepared according to the following proportion to obtain a mixture D1, the mixture D1 is filled between two substrates of a liquid crystal device for performance test, and the composition and test data of the mixture D1 are shown in Table 2:
TABLE 2
| Components | Percent by weight% | Performance of | |
| 3CPP2 | 10 | Cp | 74.5 |
| 3CCV1 | 9 | Δn | 0.109 |
| 3CC2 | 9 | ε ∥ | 3.3 |
| 3CC4 | 8 | ε ⊥ | 6.3 |
| 3CCP1 | 8 | Δε | -3.0 |
| 5CCP1 | 5 | γ 1 | 107 |
| 3CCWO2 | 6.5 | LTS | 5 days crystallization at-25 DEG C |
| 3PWO2 | 18 | K 11 | 14.9 |
| 3CPWO2 | 4.5 | K 33 | 15.8 |
| 3CWO2 | 11.5 | ||
| 3CPO1 | 5.5 | ||
| 4CCWO2 | 5 | ||
| P-1 | 0.3 |
Example M1
The liquid crystal was prepared in the following proportions to obtain a mixture M1, which was filled between two substrates of a liquid crystal device for performance testing, and the composition and test data of the mixture M1 are shown in table 3:
TABLE 3
Comparative example D2
The liquid crystal was prepared in the following proportions to obtain a mixture D2, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture D2 are shown in table 4:
TABLE 4
Example M2
The liquid crystal was prepared in the following proportions to obtain a mixture M2, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture M2 are shown in table 5:
TABLE 5
Comparative example D3
The liquid crystal was prepared in the following proportions to obtain a mixture D3, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture D3 are shown in table 6:
TABLE 6
Example M3
The liquid crystal was prepared in the following proportions to obtain a mixture M3, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture M3 are shown in table 7:
TABLE 7
| Components | Percent by weight% | Performance of | |
| 3CWO2 | 18 | Cp | 78.5 |
| 5CWO2 | 10 | Δn | 0.104 |
| 3CCWO2 | 2.5 | ε ∥ | 3.3 |
| 2CPWO2 | 11 | ε ⊥ | 6.4 |
| 2PPWO2 | 10 | Δε | -3.1 |
| 3CC1OW O1C(5,2O) | 8 | γ 1 | 87 |
| 3CCP3 | 18 | LTS | Uncrystallized at-25 ℃ for 10 days |
| 3CC2 | 21 | K 11 | 14.8 |
| 4CC3 | 1.5 | K 33 | 16.7 |
Comparative example D4
The liquid crystal was prepared in the following proportions to obtain a mixture D4, which was filled between two substrates of the liquid crystal display for performance testing, and the composition and test data of the mixture D4 are shown in table 8:
TABLE 8
Example M4
The liquid crystal was prepared in the following proportions to obtain a mixture M4, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture M4 are shown in table 9:
TABLE 9
Example M5
The liquid crystal was prepared in the following proportions to obtain a mixture M5, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture M5 are shown in table 10:
watch 10
Example M6
The liquid crystal was prepared in the following proportions to obtain a mixture M6, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture M6 are shown in table 11:
TABLE 11
Example M7
The liquid crystal was prepared in the following proportions to obtain a mixture M7, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture M7 are shown in table 12:
TABLE 12
Example M8
The liquid crystal was prepared in the following proportions to obtain a mixture M8, which was filled between two substrates of the liquid crystal display for performance testing, and the composition and test data of the mixture M8 are shown in table 13:
watch 13
| Components | Percent% | Performance of | |
| 3CC2 | 23 | Cp | 76.5 |
| 3CC4 | 3 | Δn | 0.119 |
| 3CC5 | 4 | Δε | -3.1 |
| 5PP1 | 14 | γ 1 | 86 |
| 3PWO2 | 6 | t(ms) | 15 |
| 3C1OWO2 | 5 | LTS | Uncrystallized at-25 ℃ for 10 days |
| 3CCP1 | 3 | ||
| 3CPP2 | 4 | ||
| 2CPWO2 | 9 | ||
| 2CC1OWO1C(5,1V,4O) | 8 | ||
| 3CPWO2 | 9 | ||
| 3CC1OWO1C(5,2O) | 12 | ||
| P-49 | 0.27 | ||
| P-43 | 0.005 |
Example M9
The liquid crystal was prepared in the following proportions to obtain a mixture M9, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture M9 are shown in table 14:
TABLE 14
Example M10
The liquid crystal was prepared in the following proportions to obtain a mixture M10, which was filled between two substrates of a liquid crystal display for performance testing, and the composition and test data of the mixture M10 are shown in table 15:
watch 15
Example M11
The liquid crystal was prepared in the following proportions to obtain a mixture M11, which was filled between two substrates of the liquid crystal display for performance testing, and the composition and test data of the mixture M11 are shown in table 16:
TABLE 16
| Components | Percent by weight% | Performance of | |
| 2CPWO2 | 4 | Cp | 112 |
| 3CPWO2 | 7 | Δn | 0.102 |
| 3C1OWO1C(5,2O) | 7 | Δε | -3.2 |
| 2CC1OWO1C(5,3O) | 11 | K 11 | 18.9 |
| 3CC1OWO1C(5,3O) | 10 | K 33 | 19.2 |
| 4CC1OWO1C(5,2O) | 8 | γ 1 | 154 |
| V2MO3 | 3 | t(ms) | 22 |
| 3CPP2 | 6 | Low temperature storage | 10 days at-20 deg.CCrystallization of |
| 3CPPC3 | 4 | ||
| 3CGPC3 | 3 | ||
| 3CC2 | 19 | ||
| 4CC3 | 5 | ||
| 3CCP1 | 9 | ||
| 3PP1 | 4 | ||
| P-25 | 0.3 |
Example M12
To the above mixture of D1-D4, M1-M11 was added 300ppm of each of the following additives:
by UV (313nm 5.5 mw/cm) 2 ) Irradiating for two minutes under a voltage of 20V and then UV (313nm 0.5 mw/cm) 2 ) The pre-tilt angle, threshold voltage and response time and RM residue were measured separately for 90min of irradiation, and the results are shown in table 17.
TABLE 17 test Properties of liquid Crystal compositions
| Pretilt angle (°) | Threshold voltage (V) | Response time (ms) | RM residue (ppm) | |
| D1 | 88.9 | 2.492 | 15.4 | 18 |
| D2 | 88.1 | 2.565 | 14.8 | 22 |
| D3 | 88.0 | 2.695 | 13.8 | 24 |
| D4 | 88.2 | 2.667 | 14.2 | 26 |
| M1 | 88.5 | 2.209 | 11.0 | 3 |
| M2 | 88.2 | 2.352 | 10.2 | 2 |
| M3 | 88.3 | 2.433 | 11.3 | 0 |
| M4 | 88.9 | 2.379 | 12.4 | 4 |
| M5 | 88.0 | 2.562 | 10.2 | 3 |
| M6 | 88.8 | 2.263 | 12.4 | 5 |
| M7 | 88.5 | 2.376 | 12.5 | 7 |
| M8 | 88.4 | 2.545 | 13.2 | 9 |
| M9 | 88.6 | 2.193 | 12.7 | 2 |
| M10 | 88.1 | 2.392 | 11.6 | 0 |
| M11 | 88.3 | 2.603 | 15.4 | 2 |
Pretilt angle stability test
Several of the above test cells were selected, backlit at 60 ℃, aged for 300h, tested for pretilt angle, and evaluated for pretilt angle stability, with the results shown in table 18 below.
TABLE 18 pretilt stability test
As is apparent from the test data of the above examples and comparative examples, the liquid crystal composition of the present invention has a very low rotational viscosity, and at the same time, a liquid crystal mixture having good phase properties and good low temperature properties, is UV-irradiated and capable of forming a pretilt angle which is stable for a long period of time, has less RM residues, a lower threshold voltage and a faster response time. The liquid crystal composition can meet the requirements of liquid crystal display devices on low power consumption and good display effect, and has higher application value in IPS mode, FFS mode and VA mode, particularly PSVA mode liquid crystal displays.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (16)
1. A polymerizable liquid crystal composition, comprising:
(1) At least one compound of formula I:
wherein R is A1 Is represented by C 1 -C 12 Alkyl of (C) 1 -C 12 Alkoxy or C 2 -C 12 Alkenyl of (a);
L 1 、L 2 independently of one another, H or-CH 3 ；
Ring A1 and ring A2 independently represent
Ring A3 represents
Or the said
Wherein one or both single bonds are substituted by a double bond;
Z A represents a carbon-carbon single bond, -CH 2 CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CO-O-、-CF 2 CF 2 -or-CF = CF-;
a is 0 or 1;
(2) At least one compound of the formula P:
wherein ring B1, ring B2 and ring B3 independently represent
Or the said
One or more of H in (a) is-F, -Cl or-OCH 3 Substitution;
Z 4 、Z 5 independently of one another, a carbon-carbon single bond, -CH 2 CH 2 -、-CH＝CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CO-O-、CF 2 CF 2 -or-CF = CF-;
b. c are independently of each other an integer from 0 to 4;
P 1 、P 2 independently of one another, represent a polymerizable group;
Sp 1 、Sp 2 independently of one another, represent a spacer group or a single bond;
(3) At least one compound of formula II:
wherein R is C1 、R C2 Independently of one another represent C 1 -C 12 Alkyl of (C) 1 -C 12 Alkoxy or C 2 -C 12 Alkenyl of (a);
ring C1 and ring C2 independently represent
And at least one of the rings C1 and C2 is
Or the above-mentioned
At most one H on (a) is substituted by F;
d is 0, 1 or 2; and when d is 2, rings C2 are the same or different;
(4) At least one compound of formula III:
wherein R is D1 、R D2 Independently of one another represent C 1 -C 12 Alkyl of (C) 1 -C 12 Alkoxy or C 2 -C 12 The alkenyl group of (1).
2. The polymerizable liquid crystal composition according to claim 1, wherein the compound represented by the general formula I is selected from one or more of the following compounds:
3. the polymerizable liquid crystal composition according to claim 2, wherein the compound represented by the general formula I is selected from one or more of the following compounds:
4. the polymerizable liquid crystal composition according to claim 1, wherein the compound represented by the general formula P is selected from one or more of the following compounds:
wherein Sp represents a spacer group or a single bond.
5. The polymerizable liquid crystal composition according to claim 4, wherein the compound represented by the general formula P is one or more selected from the following compounds:
6. the polymerizable liquid crystal composition according to claim 1, wherein the compound represented by the general formula II is selected from one or more of the following compounds:
7. the polymerizable liquid crystal composition of claim 6, wherein the compound represented by the general formula II is selected from one or more of the following compounds:
8. the polymerizable liquid crystal composition of claim 1, wherein the compound represented by the general formula III is selected from one or more of the following compounds:
9. a polymerizable liquid crystal composition according to any one of claims 1 to 8, wherein the polymerizable liquid crystal composition comprises, by mass, 1 to 50% of the compound represented by the general formula I, 0.001 to 5% of the compound represented by the general formula P, 1 to 60% of the compound represented by the general formula II, and 1 to 60% of the compound represented by the general formula III.
10. The polymerizable liquid crystal composition of any one of claims 1-8, further comprising one or more compounds of formula IV:
wherein R is G1 、R G2 Independently of one another represent C 1 -C 12 Alkyl of (C) 1 -C 12 Alkoxy group of (a); or, said C 1 -C 12 Alkyl of (C) 1 -C 12 At least one hydrogen atom in the alkoxy group of (a) is independently substituted by halogen; or, said C 1 -C 12 Alkyl of (C) 1 -C 12 One of alkoxy groups of (2) -CH 2 -or at least two non-adjacent-CHs 2 -independently of each other by-O-, -CH = CH-, -C ≡ C-, -CO-O-, or-O-CO-in a manner not directly linked;
X 1 、X 2 independently of one another represent-F, -CF 3 ；
The polymerizable liquid crystal composition contains 0.1-20% of the compound shown in the general formula IV by mass percent.
11. The polymerizable liquid crystal composition of claim 10, wherein the compound of formula IV is selected from one or more of the following compounds:
12. the polymerizable liquid crystal composition according to any one of claims 1 to 8, further comprising one or more compounds represented by the general formula M:
wherein R is M1 、R M2 Independently of one another represent C 1 -C 12 Alkyl or C of 2 -C 12 Alkenyl of (a);
ring M1 and ring M2 independently represent
Z M Represents a carbon-carbon single bond, -CH 2 CH 2 -、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-CO-O-、-CF 2 CF 2 -or-CF = CF-;
m is 0, 1 or 2;
the polymerizable liquid crystal composition contains 1-50% of the compound shown in the general formula M by mass percent.
13. The polymerizable liquid crystal composition according to claim 12, wherein the compound represented by the general formula M is one or more selected from the group consisting of:
14. the polymerizable liquid crystal composition of claim 13, wherein the compound of formula M is selected from one or more of the following compounds:
15. the polymerizable liquid crystal composition according to any one of claims 1 to 14, wherein one or more additives are further added to the polymerizable liquid crystal composition, and the addition amount of the additives is 0 to 5% by mass.
16. A liquid crystal display comprising the polymerizable liquid crystal composition according to any one of claims 1 to 15.
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| CN116286024A (en) * | 2022-09-08 | 2023-06-23 | 重庆汉朗精工科技有限公司 | Negative liquid crystal composition and application thereof |
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