CN116064048A - Liquid crystal composition and liquid crystal display device comprising same - Google Patents
Liquid crystal composition and liquid crystal display device comprising same Download PDFInfo
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- CN116064048A CN116064048A CN202111283412.7A CN202111283412A CN116064048A CN 116064048 A CN116064048 A CN 116064048A CN 202111283412 A CN202111283412 A CN 202111283412A CN 116064048 A CN116064048 A CN 116064048A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 171
- 239000000203 mixture Substances 0.000 title claims abstract description 123
- 150000001875 compounds Chemical class 0.000 claims abstract description 137
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 34
- 230000003287 optical effect Effects 0.000 abstract description 25
- 230000004044 response Effects 0.000 abstract description 12
- 238000012360 testing method Methods 0.000 description 26
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 238000011056 performance test Methods 0.000 description 7
- 239000000654 additive Substances 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 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 description 1
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 101100208473 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) lcm-2 gene Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 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
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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
The present invention provides a liquid crystal composition and a liquid crystal display device including the same, the liquid crystal composition including at least one compound of formula F and at least one compound selected from the group consisting of compounds of formulae a-1 and a-2, the liquid crystal composition having a large vertical dielectric constant, a large ratio of vertical dielectric constant to dielectric anisotropy, a high transmittance, a small rotational viscosity, a high VHR value while maintaining a proper optical anisotropy, a proper clearing point, a proper dielectric anisotropy, such that the liquid crystal display device including the liquid crystal composition has a proper temperature use range, a proper threshold voltage, a good contrast ratio, a high transmittance, a high response speed, and a high reliability.
Description
Technical Field
The invention relates to the field of liquid crystals, in particular to a liquid crystal composition and a liquid crystal display device comprising the liquid crystal composition.
Background
The liquid crystal display device can be used for various household electrical appliances such as a timepiece and an electronic calculator, a measuring device, an automobile panel, a word processor, a computer, a printer, a television, and the like. The liquid crystal display element may be classified into a type of PC (phase change), TN (twisted nematic), STN (super twisted nematic ), ECB (electrically controlled birefringence, electrically controlled birefringence), OCB (optically compensated bend ), IPS (in-plane switching), VA (vertical alignment), and the like according to the type of display mode. Liquid crystal display elements can be classified into a PM (passive matrix) type and an AM (active matrix) type according to the driving method of the elements. PM is classified into static (static) and multiplex (multiplex) types. AM is classified into TFT (thin film transistor ), MIM (metal insulator metal, metal-insulator-metal) and the like. The types of TFTs include amorphous silicon (amorphous silicon) and polysilicon (polycrystal silicon). The latter is classified into a high temperature type and a low temperature type according to the manufacturing process. The liquid crystal display element can be classified into a reflective type using natural light, a transmissive type using background light, and a semi-transmissive type using both natural light and backlight light sources, according to the type of light source.
The liquid crystal display element contains a liquid crystal composition having a nematic phase, and the liquid crystal composition has appropriate characteristics. By improving the characteristics of the liquid crystal composition, an AM element having good characteristics can be obtained. The correlation between the characteristics of the liquid crystal composition and the characteristics of the AM element is summarized in table 1 below.
TABLE 1 Properties of liquid Crystal composition and AM element
| Numbering device | Characteristics of the liquid Crystal composition | Characteristics of AM element |
| 1 | Wide temperature range of nematic phase | Can be used in a wide temperature range |
| 2 | Low viscosity | Short response time |
| 3 | Proper optical anisotropy | High contrast |
| 4 | Positive or negative dielectric anisotropy with large absolute value | Low threshold voltage, low power consumption, and high contrast |
| 5 | Has a large specific resistance | High voltage holding ratio and contrast ratio |
| 6 | Is stable to ultraviolet rays and heat | Long service life |
| 7 | Large elastic constant | High contrast and short response time |
In order to increase the response speed of the liquid crystal display device, it is necessary to reduce the rotational viscosity of the liquid crystal material as much as possible. However, since a liquid crystal material having a low viscosity generally has a low clearing point, optical anisotropy, and the like, it is necessary to consider other performance requirements in lowering the viscosity when preparing a formulation of a mixed liquid crystal.
The threshold voltage of the mixed liquid crystal mainly depends on the delta epsilon of the liquid crystal, and the delta epsilon is large, so that the threshold voltage of the liquid crystal is reduced, and the delta epsilon of the mixed liquid crystal is modulated to a proper value through the mixing of monomer liquid crystals with different polarities, so that the requirement of the working voltage of a display device is met. However, increasing Δεof the liquid crystal may increase the viscosity of the liquid crystal and decrease the stability of the liquid crystal.
The transmittance is proportional to the ratio of the vertical dielectric constant to the dielectric anisotropy (ε), so the more negative liquid crystal is incorporated, the higher the transmittance of the display device, but the more negative monomer, the response speed of the display device is reduced. Therefore, how to obtain a liquid crystal display device with both higher transmittance and faster response time is still a problem to be solved.
With the improvement of resolution of liquid crystal displays, liquid crystal displays of 4K and 8K type are increasingly emerging, and thus liquid crystal panels are required to have smaller aperture ratios and higher transmittance. The negative liquid crystal composition has higher transmittance, particularly in the PSA mode and the NFFS mode, the advantage of high transmittance is more obvious, but the structure of the negative liquid crystal determines that the negative liquid crystal composition has larger rotational viscosity, high ion concentration and low voltage retention rate, so that the negative liquid crystal afterimage effect is obviously inferior to that of the positive liquid crystal, and therefore, the development of the negative liquid crystal composition with smaller rotational viscosity and higher voltage retention rate is needed to improve the defects of the traditional negative liquid crystal, and the liquid crystal composition meeting the market demand is provided.
The Chinese patent application CN1942461A and the German patent application DE10101022A1 disclose a liquid crystal compound capable of solving the problems to a certain extent, and the Chinese patent application CN107973766A performs ring substitution on the end group structure of the compound on the basis of the prior art, but the compound disclosed at present has the problems of smaller absolute value of dielectric anisotropy, larger rotational viscosity and poorer low-temperature intersolubility of voltage retention rate. Chinese patent applications CN105820824a and CN110577838A disclose a dibenzothiophene/furan liquid crystal composition which solves the above problems to some extent, but still has a higher rotational viscosity, lower VHR, in particular lower VHR (UV). It is known that the liquid crystal panel is required to be irradiated with UV light to some extent during the manufacturing process, and the light measurement of ultraviolet light with a wavelength of 365nm is about 6000 MJ to 1000MJ, whereas the conventional dibenzofuran and dibenzothiophene compounds have lower VHR (UV) after being irradiated with UV light, so that the reliability of the display is reduced, and a ghost is generated.
It is not possible to adjust many physical properties of the liquid crystal at the same time by the preparation of the mixed liquid crystal formulation, and it is possible to adjust one property parameter without affecting the value of the other parameter, and it is still a highly desirable problem in the art to add a certain monomer liquid crystal to adjust a certain property parameter of the mixed liquid crystal, which may be advantageous for one or more other property parameters, but may be disadvantageous for the improvement of some other property parameters, and thus how to obtain a liquid crystal composition, which can solve or partially solve the above-mentioned problems.
Disclosure of Invention
The invention aims to: in view of the drawbacks of the prior art, an object of the present invention is to provide a liquid crystal composition having a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity, and a higher VHR value while maintaining a proper optical anisotropy, a proper clearing point, and a proper dielectric anisotropy.
The invention also aims to provide a liquid crystal display device comprising the liquid crystal composition.
The technical scheme is as follows: in order to achieve the above object, the present invention provides a liquid crystal composition comprising:
At least one compound of the formula F:
At least one compound selected from the group consisting of compounds of the general formula A-1 and the general formula A-2:
wherein,,
R F1 represents-H, halogen, straight-chain or branched alkyl having 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) carbon atoms,
Wherein one or not adjacent two or more-CH groups in the straight-chain or branched alkyl group having 1 to 12 carbon atoms 2 -may each independently be replaced by-c≡c-, -O-, -CO-O-or-O-CO-, and one or more-H in a linear or branched alkyl group containing 1 to 12 carbon atoms may each independently be replaced by-F or-Cl;
R F2 representing replacement of single bonds by double bonds in one or more rings
R A1 And R is A2 Each independently represents a linear or branched alkyl group having 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) carbon atoms,
Wherein one or not adjacent two or more-CH groups in the straight-chain or branched alkyl group having 1 to 12 carbon atoms 2 Can be independently and individually substituted by-CH=CH-, -C≡C-, -O-, -CO-O-or-O-CO-replacementSubstituted, and containing linear or branched alkyl groups of 1 to 12 carbon atoms,
Wherein one or more of-H's may each be independently substituted with-F or-Cl;
Ring(s)
Ring->
Ring->
Ring->
And ring
Each independently represents->
Wherein the method comprises the steps of
One or more of-CH 2 -can be replaced by-O-, one or more single bonds in the ring can be replaced by double bonds, wherein +.>
wherein-H may be independently substituted by-CN, -F or-Cl, and-ch=may be substituted by-n=in one or more rings;
X F representation-O-, O- -S-or-CO-;
X A1 and X A2 Each independently represents halogen, a linear or branched haloalkyl or haloalkoxy group having 1 to 5 carbon atoms, or a linear or branched haloalkenyl or haloalkenoxy group having 2 to 5 carbon atoms;
L F1 and L F2 Each independently represents-H, -F, -Cl, -CF 3 or-OCF 3 ；
L A11 、L A12 、L A13 、L A21 And L A22 Each independently represents-H, an alkyl group having 1 to 3 carbon atoms, or halogen;
Z F1 、Z F2 、Z A11 and Z A21 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -、-(CH 2 ) 4 -、-CF 2 O-or-OCF 2 -；
Z A22 Represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -or- (CH) 2 ) 4 -；
Z F4 Represents a single bond, -O-, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -、-(CH 2 ) 4 -、-CF 2 O-or-OCF 2 -；
n F1 And n F2 Each independently represents 0, 1 or 2, wherein when n F1 When 2 is represented, the ring
May be the same or different, wherein when n F2 When 2 is indicated, the ring->
Z, which may be the same or different F2 May be the same or different;
n F3 an integer of 0 to 4;
n A11 represents 0, 1, 2 or 3, wherein when n A11 When=2 or 3, the ring 
Z, which may be the same or different A11 May be the same or different;
n A12 represents 1 or 2, wherein when n A12 When=2, the ring
May be the same or different; and is also provided with
n A2 Represents 0, 1, 2 or 3, wherein when n A2 When=2 or 3, the ring
Z, which may be the same or different A21 May be the same or different.
In some embodiments of the invention, preferably, L F1 And L F2 Each independently represents-F or-Cl.
In some embodiments of the invention, the compound of formula F is selected from the group consisting of:
Wherein,,
X F1 and X F2 Each independently represents-CH 2 -or-O-.
In some embodiments of the inventionIn embodiments, preferably, n F3 Represents 0 or 1; preferably n F3 And represents 0.
In some embodiments of the invention, preferably, Z F1 And Z F2 Each independently represents a single bond, -CH 2 O-or-OCH 2 -, further preferably, Z F1 And Z F2 All represent a single bond.
In some embodiments of the invention, n F1 And n F2 At least one of them represents 0; preferably n F1 And n F2 All represent 0.
In some embodiments of the invention, preferably, R F1 Represents a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 9 carbon atoms, or a linear or branched alkenyl group having 2 to 10 carbon atoms; further preferably, R F1 Represents a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkoxy group having 1 to 7 carbon atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms.
In some embodiments of the invention, the compound of formula F is selected from the group consisting of a compound of formula F-1, a compound of formula F-2, a compound of formula F-28, a compound of formula F-29, a compound of formula F-24, and a compound of formula F-25 in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity, and a higher VHR value for the liquid crystal composition of the invention.
In some embodiments of the present invention, it is preferred to adjust the content of the compound of formula F such that the liquid crystal composition of the present invention has an appropriate optical anisotropy, an appropriate clearing point, an appropriate dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value.
In some embodiments of the invention, the compound of formula F comprises 0.1% to 30% (including all values therebetween) by weight of the liquid crystal composition, e.g., 0.1%, 0.5%, 1%, 2%, 4%, 5%, 6%, 8%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 27%, 28%, 30% or a range of values between any two thereof.
In some embodiments of the invention, the liquid crystal composition preferably comprises at least two compounds of formula F in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger perpendicular dielectric constant, a larger ratio of perpendicular dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value.
In some embodiments of the present invention, it is preferable to adjust the content of the compound selected from the group consisting of the compounds of the general formulae a-1 and a-2 so that the liquid crystal composition comprising the same has an appropriate optical anisotropy, an appropriate clearing point, an appropriate dielectric anisotropy, a larger perpendicular dielectric constant, a larger ratio of perpendicular dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity, and a higher VHR value.
In some embodiments of the invention, the compounds selected from the group consisting of compounds of formula a-1 and formula a-2 comprise 0.1% to 50% by weight of the liquid crystal composition (including all values therebetween), e.g., 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 17%, 18%, 20%, 22%, 24%, 25%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 41.5%, 42%, 44%, 46%, 48%, 50% or a range of values between any two thereof.
In some embodiments of the invention, the compound of formula a-1 is selected from the group consisting of:
Wherein,,
R A1 represents a linear or branched alkyl group having 1 to 8 carbon atoms,
Wherein one or not adjacent two or more-CH's in the straight-chain or branched alkyl group having 1 to 8 carbon atoms 2 -may each independently be replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-, and one or more-H present in these groups may each independently be substituted by-F or-Cl;
R v and R is w Each independently represents-CH 2 -or-O-;
L A11 、L A12 、L A11 ’、L A12 ’、L A14 、L A15 and L A16 Each independently represents-H or-F;
L A13 and L A13 ' each independently represents-H or-CH 3 ；
X A1 representing-F, -CF 3 or-OCF 3 The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with
v and w each independently represent 0 or 1.
In some embodiments of the present invention, in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value of the liquid crystal composition of the present invention, it is preferred that the compound of formula A-1 is selected from the group consisting of the compound of formula A-1-7, the compound of formula A-1-13, the compound of formula A-1-14, the compound of formula A-1-16, the compound of formula A-1-17 and the compound of formula A-1-21.
In some embodiments of the present invention, it is preferred that the liquid crystal composition of the present invention comprises at least two (e.g., three, four) compounds of formula a-1 in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value of the liquid crystal composition of the present invention.
In some embodiments of the present invention, it is preferred to adjust the content of the compound of formula a-1 such that the liquid crystal composition comprising it has a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a large perpendicular dielectric constant, a large ratio of perpendicular dielectric constant to dielectric anisotropy, a high transmittance, a small rotational viscosity and a high VHR value.
In some embodiments of the invention, the compound of formula a-1 comprises 0.1% to 40% (including all values therebetween) by weight of the liquid crystal composition, e.g., 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 30.5%, 32%, 34%, 36%, 38%, 40% or a range of values between any two thereof.
In the case where the viscosity of the liquid crystal composition of the present invention is kept low and the response speed is high, the preferable content of the compound of the general formula a-1 is preferably set to a low lower limit and the upper limit; further, when the clearing point of the liquid crystal composition of the present invention is kept high and the temperature stability is good, it is preferable to keep the lower limit value slightly low and the upper limit value slightly low; in order to keep the drive voltage low and to increase the absolute value of the dielectric anisotropy, it is preferable to have a slightly higher lower limit value and a slightly higher upper limit value.
In some embodiments of the invention, the compound of formula a-2 is selected from the group consisting of:
Wherein,,
R A2 represents a linear or branched alkyl group having 1 to 8 carbon atoms, wherein one or not adjacent two or more-CH groups in the linear or branched alkyl group having 1 to 8 carbon atoms 2 -may each independently be replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-, and one or more-H present in these groups may each independently be substituted by-F or-Cl;
L A21 、L A22 、L A23 、L A24 and L A25 Each independently represents-H or-F; and is also provided with
X A2 representing-F, -CF 3 、-OCF 3 or-CH 2 CH 2 CH＝CF 2 。
In some embodiments of the present invention, to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger perpendicular dielectric constant, a larger ratio of perpendicular dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value, it is preferred that the compound of formula a-2 is selected from the group consisting of a compound of formula a-2-4, a compound of formula a-2-5, a compound of formula a-2-12, a compound of formula a-2-15 and a compound of formula a-2-16.
In some embodiments of the invention, in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value for the liquid crystal composition of the invention, it is preferred that the liquid crystal composition comprises at least two (e.g. three, four) compounds of formula a-2.
In some embodiments of the present invention, it is preferred to adjust the content of the compound of the formula a-2 such that the liquid crystal composition comprising it has a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a large perpendicular dielectric constant, a large ratio of perpendicular dielectric constant to dielectric anisotropy, a high transmittance, a small rotational viscosity and a high VHR value.
In some embodiments of the invention, the compound of formula a-2 comprises 0.1% to 40% (including all values therebetween) by weight of the liquid crystal composition, e.g., 0.1%, 1%, 4%, 5%, 6%, 8%, 9%, 10%, 11%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40% or a range of values between any two thereof.
In the case where the viscosity of the liquid crystal composition of the present invention is kept low and the response speed is high, the preferable content of the compound of the general formula a-2 is preferably set to a low lower limit and the upper limit; further, when the clearing point of the liquid crystal composition of the present invention is kept high and the temperature stability is good, it is preferable to keep the lower limit value slightly low and the upper limit value slightly low; in order to keep the drive voltage low and to increase the absolute value of the dielectric anisotropy, it is preferable to have a slightly higher lower limit value and a slightly higher upper limit value.
In some embodiments of the invention, the liquid crystal composition further comprises at least one compound of formula M:
wherein,,
R M1 and R is M2 Each independently represents a linear or branched alkyl group having 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) carbon atoms, 
Wherein one or not adjacent two or more-CH groups in the straight-chain or branched alkyl group having 1 to 12 carbon atoms 2 -may each be independently replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
ring(s)
Ring->
And (C) a ring->
Each independently represents->
Wherein->
One or more of-CH 2 -can be replaced by-O-, one or more single bonds in the ring can be replaced by double bonds, wherein +.>
At most one-H of (c) may be substituted by halogen;
Z M1 and Z M2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-C≡C-、-CH＝CH-、-CH 2 CH 2 -or- (CH) 2 ) 4 -; and is also provided with
n M Represents 0, 1 or 2, wherein when n M When=2, the ring
Z, which may be the same or different M2 May be the same or different.
In some embodiments of the invention, preferably, R M1 And R is M2 Each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 9 carbon atoms, or a linear or branched alkenyl group having 2 to 10 carbon atoms; further preferably, R M1 And R is M2 Each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkoxy group having 1 to 7 carbon atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms.
In some embodiments of the invention, preferably, R M1 And R is M2 Each independently represents a linear alkenyl group having 2 to 8 carbon atoms; further preferably, R M1 And R is M2 Each independently represents a linear alkenyl group having 2 to 5 carbon atoms.
In some embodiments of the invention, preferably, R M1 And R is M2 One of which is a linear alkenyl group having 2 to 5 carbon atoms and the other is a linear alkyl group having 1 to 5 carbon atoms.
In some embodiments of the invention, preferably, R M1 And R is M2 Each independently represents a linear alkoxy group having 1 to 8 carbon atoms; further preferably, R M1 And R is M2 Each independently represents a linear alkoxy group having 1 to 5 carbon atoms.
In some embodiments of the invention, preferably, R M1 And R is M2 One of them is a linear alkoxy group having 1 to 5 carbon atoms, and the other isOne is a straight chain alkyl group containing 1 to 5 carbon atoms.
In some embodiments of the invention, R is preferred when reliability is important M1 And R is M2 Are all alkyl groups; in the case where importance is attached to reducing the volatility of the compound, R is preferably M1 And R is M2 Are all alkoxy groups; when importance is attached to the reduction of viscosity, R is preferable M1 And R is M2 At least one of which is alkenyl.
As used herein, the term "containing 1-r carbon atoms" (where r is an integer greater than 1) may be any integer between 1 and r (inclusive of the end values 1 and r) carbon atoms, for example, containing 2 carbon atoms, containing (r-1) carbon atoms, or containing r carbon atoms. For example, "containing 1-12 carbon atoms" may be containing 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.
As used herein, the term "y 1 -y 2 The integer "of (a) may be any integer between the ranges (inclusive of the end value y 1 And y 2 ). For example, an "integer of 0-12" may be, for example, 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.
The alkenyl group in the present invention is preferably selected from the group represented by any one of the formulas (V1) to (V9), and particularly preferably is formula (V1), formula (V2), formula (V8) or (V9). The groups represented by the formulas (V1) to (V9) are as follows:
wherein represents the attachment site in the bonded ring structure.
The alkenyloxy group in the present invention is preferably selected from the group represented by any one of the formulae (OV 1) to (OV 9), and particularly preferably is the formula (OV 1), the formula (OV 2), the formula (OV 8) or the formula (OV 9). The groups represented by the formulas (OV 1) to (OV 9) are as follows:
wherein represents the attachment site in the bonded ring structure.
In some embodiments of the invention, the compound of formula M is selected from the group consisting of:
In some embodiments of the invention, in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value of the liquid crystal composition of the invention, it is preferred that the compound of formula M is selected from the group consisting of a compound of formula M-1, a compound of formula M-2, a compound of formula M-4, a compound of formula M-11, a compound of formula M-13, a compound of formula M-14, a compound of formula M-23 and a compound of formula M-24.
In some embodiments of the present invention, the content of the compound of formula M must be appropriately adjusted according to the desired properties of solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, drop marks, burn-in, dielectric anisotropy, etc.
Regarding the content of the compound of the general formula M, when it is necessary to keep the viscosity of the liquid crystal composition of the present invention low and the response time short, it is preferable that the lower limit value is high and the upper limit value is high; further, when it is necessary to keep the clear point of the liquid crystal composition of the present invention high and the temperature stability is good, it is preferable that the lower limit value is high and the upper limit value is high; in order to keep the drive voltage low and to increase the absolute value of the dielectric anisotropy, it is preferable that the lower limit value and the upper limit value be low.
In some embodiments of the present invention, it is preferred to adjust the content of the compound of formula M such that the liquid crystal composition of the present invention has a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a large vertical dielectric constant, a large ratio of vertical dielectric constant to dielectric anisotropy, a high transmittance, a small rotational viscosity and a high VHR value.
In some embodiments of the invention, the compound of formula M comprises 0.1% to 60% (including all values therebetween) by weight of the liquid crystal composition, e.g., 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 34.5%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60% or a range of values between any two thereof.
In some embodiments of the invention, the liquid crystal composition of the invention further comprises at least one compound of formula N:
wherein,,
R N1 and R is N2 Each independently represents a linear or branched alkyl group having 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) carbon atoms,
Wherein one or not adjacent two or more-CH groups in the straight-chain or branched alkyl group having 1 to 12 carbon atoms 2 -may each be independently replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
ring(s)
And (C) a ring->
Each independently represents->
Wherein the method comprises the steps of
One or more of-CH 2 -can be replaced by-O-, one or more single bonds in the ring can be replaced by double bonds, wherein +. >
In which one or more of-H may be substituted by-F, -Cl or-CN and one or more of-ch=may be substituted by-n=in the ring;
Z N1 and Z N2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -、-(CH 2 ) 4 -、-CF 2 O-or-OCF 2 -；
L N1 And L N2 Independently of each other, -H, alkyl having 1 to 3 carbon atoms or halogen; and is also provided with
n N1 Represents 0, 1, 2 or 3, n N2 Represents 0 or 1, and 0.ltoreq.n N1 +n N2 Not more than 3, wherein when n N1 When=2 or 3, the ring
Z, which may be the same or different N1 May be the same or different.
In some embodiments of the invention, L N1 And L N2 All represent-H.
In some embodiments of the invention, the compound of formula N is selected from the group consisting of:
In some embodiments of the present invention, when it is desired to keep the viscosity of the liquid crystal composition of the present invention low and the response time short, it is preferable that the lower limit value and the upper limit value of the content of the compound of the general formula N be low; further, when it is desired to keep the clearing point of the liquid crystal composition of the present invention high and the temperature stability is good, it is preferable that the lower limit value and the upper limit value of the content of the compound of the general formula N be low; in order to keep the drive voltage low and to increase the absolute value of the dielectric anisotropy, it is preferable that the lower limit value and the upper limit value of the content of the compound of the formula N be high.
In some embodiments of the invention, preferably, R N1 And R is N2 Each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkyl group having 1 to 9 carbon atomsAn oxy group, or a linear or branched alkenyl group containing 2 to 10 carbon atoms; further preferably, R N1 And R is N2 Each independently represents a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkoxy group having 1 to 7 carbon atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms.
In some embodiments of the present invention, preferably, the compound of formula N is selected from the group consisting of a compound of formula N-1, a compound of formula N-2, a compound of formula N-3, a compound of formula N-9, a compound of formula N-12, a compound of formula N-13, a compound of formula N-19, a compound of formula N-21, a compound of formula N-24, a compound of formula N-27, and a compound of formula N-30.
In some embodiments of the present invention, in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value for the liquid crystal composition of the present invention, it is preferred that the compound of formula N is selected from the group consisting of a compound of formula N-2, a compound of formula N-3, a compound of formula N-9, a compound of formula N-12 and a compound of formula N-13; preferably, the liquid crystal composition of the present invention comprises at least one compound of formula N-9.
In some embodiments of the invention, in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value for the liquid crystal composition of the invention, preferably the compound of formula N is selected from the group consisting of a compound of formula N-19, a compound of formula N-21, a compound of formula N-24, a compound of formula N-27 and a compound of formula N-30; preferably, the liquid crystal composition of the present invention comprises at least one compound of formula N-19.
In some embodiments of the present invention, it is preferred to adjust the content of the compound of formula N such that the liquid crystal composition of the present invention has an appropriate optical anisotropy, an appropriate clearing point, an appropriate dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value.
In some embodiments of the invention, the compound of formula N comprises 0.1% to 40% (including all values therebetween) by weight of the liquid crystal composition, e.g., 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 23%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40% or a range of values between any two thereof.
In some embodiments of the invention, the liquid crystal composition of the invention further comprises at least one compound of formula B:
wherein,,
R B1 and R is B2 Each independently represents halogen, -CF 3 、-OCF 3 A linear or branched alkyl group having 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) carbon atoms,
Wherein the alkyl group is a straight-chain or branched alkyl group having 1 to 12 carbon atoms, (-) -a>
One or not adjacent two or more-CH 2 -may each be independently replaced by-c≡c-, -O-, -CO-O-or-O-CO-;
ring(s)
And (C) a ring->
Each independently ofFloor representation->
Wherein->
One or more of-CH 2 -can be replaced by-O-, one or more single bonds in the ring can be replaced by double bonds, wherein +.>
wherein-H may be independently substituted by-CN, -F or-Cl, and-ch=may be substituted by-n=in one or more rings;
X B representation-O-, O- -S-or-CO-;
L B1 and L B2 Each independently represents-H, -F, -Cl, -CF 3 or-OCF 3 ；
Z B1 And Z B2 Each independently represents a single bond, -O-, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -、-(CH 2 ) 4 -、-CF 2 O-or-OCF 2 -; and is also provided with
n B1 And n B2 Each independently represents 0, 1 or 2, wherein when n B1 When 2 is represented, the ring
May be the same or different, wherein when n B2 When 2 is indicated, the ring->
Z, which may be the same or different F2 May be the same or different.
In some embodiments of the invention, the compound of formula B is selected from the group consisting of:
Wherein,,
R B1 ' and R B2 ' each independently represents a straight or branched alkyl group containing 1 to 11 carbon atoms.
In some embodiments of the invention, it is preferred that the liquid crystal composition of the invention comprises at least one compound of formula B-1 in order to obtain a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity and a higher VHR value of the liquid crystal composition of the invention.
In some embodiments of the present invention, it is preferred to adjust the content of the compound of formula B such that the liquid crystal composition of the present invention has a suitable optical anisotropy, a suitable clearing point, a suitable dielectric anisotropy, a large vertical dielectric constant, a large ratio of vertical dielectric constant to dielectric anisotropy, a high transmittance, a small rotational viscosity and a high VHR value.
In some embodiments of the invention, the compound of formula B comprises 0.1% to 30% (including all values therebetween) by weight of the liquid crystal composition, e.g., 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30% or a range of values between any two thereof.
In some embodiments of the invention, the liquid crystal composition further comprises at least one additive.
In addition to the above-mentioned compounds, the liquid crystal composition of the present invention may contain a usual nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, dopant, antioxidant, ultraviolet absorber, infrared absorber, polymerizable monomer, light stabilizer, or the like.
Possible dopants preferably added to the liquid crystal composition according to the invention are shown below:
In some embodiments of the invention, the dopant comprises 0% to 5% by weight of the liquid crystal composition; preferably, the dopant comprises 0.01% to 1% by weight of the liquid crystal composition.
In addition, antioxidants, light stabilizers, ultraviolet absorbers used in the liquid crystal composition of the present inventionEtcThe additives are preferably the following:
wherein n represents a positive integer of 1 to 12.
Preferably, the antioxidant is selected from the compounds shown below:
in some embodiments of the invention, the additive comprises 0% to 5% by weight of the total weight of the liquid crystal composition; preferably, the additive comprises 0.01% to 1% by weight of the total weight of the liquid crystal composition.
In still another aspect, the present invention also provides a liquid crystal display device comprising the above liquid crystal composition.
In some embodiments of the invention, the above-described liquid crystal composition is particularly suitable for use in VA, IPS or FFS type display elements.
The beneficial effects are that: compared with the prior art, the liquid crystal composition has larger vertical dielectric constant, larger ratio of the vertical dielectric constant to the dielectric anisotropy, higher transmittance, smaller rotational viscosity and higher VHR value under the condition of maintaining proper optical anisotropy, proper clearing point and proper dielectric anisotropy, so that a liquid crystal display device comprising the liquid crystal composition has proper temperature use range, proper threshold voltage, better contrast ratio, higher transmittance, faster response speed and higher reliability. .
Detailed Description
The invention will be described below in connection with specific embodiments. The following examples are illustrative of the present invention and are not intended to limit the present invention. Other combinations and various modifications within the spirit of the invention may be made without departing from the spirit or scope of the invention.
For ease of expression, in each of the following examples, the group structure of each compound is represented by the code listed in Table 2:
TABLE 2 group Structure codes for Compounds
Take as an example a compound of the formula:
the structural formula is expressed by codes listed in table 2, and can be expressed as follows: nCCGF, where n in the code represents the number of C atoms in the left-hand alkyl group, e.g., n is "3", i.e., the alkyl group is-C 3 H 7 The method comprises the steps of carrying out a first treatment on the surface of the C in the code represents 1, 4-cyclohexylene, G represents 2-fluoro-1, 4-phenylene and F represents a fluorine substituent.
The shorthand designations for the test items in the following examples are as follows:
cp clearing point (nematic phase-isotropic phase transition temperature, DEG C)
Delta n optical anisotropy (589 nm,20 ℃ C.)
Delta epsilon dielectric anisotropy (1 KHz,20 ℃ C.)
ε ⊥ Vertical dielectric constant (1 KHz,20 ℃ C.)
ε ⊥ Ratio of vertical dielectric constant to dielectric
VHR (initial) initial voltage holding ratio (%)
Voltage holding ratio after VHR (UV) ultraviolet light (UV) irradiation (%)
T r Transmittance (%)
γ 1 Rotational viscosity (mPa.s, 20 ℃ C.)
Wherein,,
cp: obtained by a melting point tester test.
An: the product was obtained by testing at 20℃under a sodium light (589 nm) source using an Abbe refractometer.
Δε：Δε＝ε || -ε ⊥ Wherein ε is || For dielectric constant parallel to the molecular axis ε ⊥ Is the dielectric constant perpendicular to the molecular axis; test conditions: VA type test box with 20 deg.C, 1KHz and box thickness of 6 μm.
VHR (initial): the initial voltage retention rate is tested by using a TOY06254 type liquid crystal physical property evaluation system; the test temperature is 60 ℃, the test voltage is 5V, the test frequency is 6Hz, and the thickness of the TN type test box is 9 mu m.
VHR (UV) was tested using a TOY06254 type liquid crystal physical property evaluation system; using a wavelength of 365nm and an energy of 6000mJ/cm 2 After the UV light of (2) is irradiated to the liquid crystal, the test temperature is 60 ℃, the test voltage is 5V, the test frequency is 6Hz, and the thickness of the TN type test box is 9 mu m.
T r : the V-T curve of the light modulation device is tested by using a DMS 505 photoelectric comprehensive tester, the maximum value of the transmittance on the V-T curve is taken as the transmittance of liquid crystal, and the test box is of a negative IPS type, and the thickness of the box is 3.5 mu m and 20 ℃.
γ 1 : the liquid crystal display is obtained by testing by using an LCM-2 liquid crystal physical property evaluation system; test conditions: 20 ℃, 160-240V and 20 mu m thick test box.
The components used in the examples below were synthesized by known methods or obtained commercially. These synthetic techniques are conventional and the resulting liquid crystal compounds have been tested to meet the electronic class of compound standards.
Liquid crystal compositions were prepared in accordance with the proportions of the respective liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared by mixing the components in proportion by a conventional method in the art, such as heating, ultrasonic wave, suspending and the like.
Comparative example 1
The liquid crystal composition of comparative example 1 was prepared according to each of the compounds listed in table 3 and weight percentages thereof, and was filled between two substrates of a liquid crystal display for performance test.
TABLE 3 formulation of liquid Crystal composition and results of Performance parameter test
Example 1
The liquid crystal composition of example 1 was prepared according to the respective compounds listed in table 4 and weight percentages thereof, and was filled between two substrates of a liquid crystal display for performance test.
TABLE 4 formulation of liquid Crystal composition and results of Performance parameter test
Example 2
The liquid crystal composition of example 2 was prepared according to the respective compounds listed in table 5 and weight percentages thereof, and was filled between two substrates of a liquid crystal display for performance test.
TABLE 5 formulation of liquid Crystal composition and results of Performance parameter test
From comparison of examples 1-2 and comparative example 1, it is apparent that the liquid crystal composition of the present invention has a larger vertical dielectric, a larger ratio of vertical dielectric to dielectric, a higher transmittance, a smaller rotational viscosity, a higher VHR value (VHR (initial) and VHR (UV)) by the synergistic effect of the compound of the general formula F and at least one compound selected from the group consisting of the compound of the general formula a-1 and the compound of the general formula a-2, so that the liquid crystal composition of the present invention maintains a proper optical anisotropy, a proper clearing point, and a proper dielectric anisotropy.
Example 3
The liquid crystal composition of example 3 was prepared according to each of the compounds listed in table 6 and its weight percentage, and was filled between two substrates of a liquid crystal display for performance test.
TABLE 6 formulation of liquid Crystal composition and results of Performance parameter test
Example 4
The liquid crystal composition of example 4 was prepared according to the respective compounds listed in table 7 and weight percentages thereof, and was filled between two substrates of a liquid crystal display for performance test.
TABLE 7 formulation of liquid Crystal composition and results of Performance parameter test
Example 5
The liquid crystal composition of example 5 was prepared according to the respective compounds listed in table 8 and weight percentages thereof, and was filled between two substrates of a liquid crystal display for performance test.
TABLE 8 formulation of liquid Crystal composition and results of Performance parameter test
Example 6
The liquid crystal composition of example 6 was formulated as each of the compounds listed in table 9 and its weight percent, and was filled between two substrates of a liquid crystal display for performance testing.
TABLE 9 formulation of liquid Crystal composition and results of Performance parameter test
Example 7
The liquid crystal composition of example 7 was prepared according to the respective compounds listed in table 10 and weight percentages thereof, and was filled between two substrates of a liquid crystal display for performance test.
TABLE 10 formulation of liquid Crystal composition and results of Performance parameter test
In summary, the liquid crystal composition of the present invention has a larger vertical dielectric constant, a larger ratio of vertical dielectric constant to dielectric anisotropy, a higher transmittance, a smaller rotational viscosity, a higher VHR value (including VHR (initial) and VHR (UV)) while maintaining a proper optical anisotropy, a proper clearing point, and a proper dielectric anisotropy (4 to 6.5), so that the liquid crystal display device including the same has a proper temperature use range, a proper threshold voltage, a better contrast ratio, a higher transmittance, a faster response speed, and a higher reliability.
The above embodiments are only for illustrating the technical concept and features of the present invention, and are intended to enable those skilled in the art to understand the present invention and to implement it, but not limit the scope of the present invention, and all equivalent changes or modifications made according to the spirit of the present invention should be included in the scope of the present invention.
Claims (11)
1. A liquid crystal composition, characterized in that the liquid crystal composition comprises:
at least one compound of the formula F:
at least one compound selected from the group consisting of compounds of the general formula A-1 and the general formula A-2:
Wherein,,
R F1 represents-H, halogen, straight-chain or branched alkyl having 1 to 12 carbon atoms,
Wherein one or not adjacent two or more of the straight-chain or branched alkyl groups having 1 to 12 carbon atoms are-CH 2 -being able to be replaced independently of each other by-c≡c-, -O-, -CO-O-or-O-CO-, and one or more-H of said linear or branched alkyl groups containing 1 to 12 carbon atoms being able to be replaced independently of each other by-F or-Cl;
R F2 representing replacement of single bonds by double bonds in one or more rings
R A1 And R is A2 Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Wherein one or not adjacent two or more of the straight-chain or branched alkyl groups having 1 to 12 carbon atoms are-CH 2 -can be replaced independently of each other by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-, and said containing 1-12 carbonsStraight-chain or branched alkyl radicals of atoms, +.>
Wherein one or more of-H can be independently replaced by-F or-Cl;
ring(s)
Ring->
Ring->
Ring->
And (C) a ring->
Each independently represents->
Wherein the method comprises the steps of
One or more of-CH 2 -can be replaced by-O-, single bonds in one or more rings can be replaced by double bonds, wherein +.>
Wherein-ch=in one or more rings can be replaced by-n=;
X F representation-O-, O- -S-or-CO-;
X A1 and X A2 Each independently represents halogen, a straight or branched haloalkyl or haloalkoxy group having 1 to 5 carbon atoms, or a halogen containing 2 to 5 carbon atomsStraight or branched chain haloalkenyl or haloalkenoxy groups of atoms;
L F1 and L F2 Each independently represents-H, -F, -Cl, -CF 3 or-OCF 3 ；
L A11 、L A12 、L A13 、L A21 And L A22 Each independently represents-H, an alkyl group having 1 to 3 carbon atoms, or halogen;
Z F1 、Z F2 、Z A11 and Z A21 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -、-(CH 2 ) 4 -、-CF 2 O-or-OCF 2 -；
Z A22 Represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -or- (CH) 2 ) 4 -；
Z F4 Represents a single bond, -O-, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -、-(CH 2 ) 4 -、-CF 2 O-or-OCF 2 -；
n F1 And n F2 Each independently represents 0, 1 or 2, wherein when n F1 When 2 is represented, the ring
Identical or different, where when n F2 When 2 is indicated, the ring->
Identical or different, Z F2 The same or different;
n F3 an integer of 0 to 4;
n A11 represents 0, 1, 2 or 3, wherein when n A11 When=2 or 3, the ring
Identical or different, Z A11 The same or different;
n A12 represents 1 or 2, wherein when n A12 When=2, the ring
The same or different; and is also provided with
n A2 Represents 0, 1, 2 or 3, wherein when n A2 When=2 or 3, the ring
Identical or different, Z A21 The same or different.
2. The liquid crystal composition according to claim 1, wherein the compound of formula F is selected from the group consisting of:
Wherein,,
X F1 and X F2 Each independently represents-CH 2 -or-O-.
3. The liquid crystal composition according to claim 1, wherein the compound of formula a-1 is selected from the group consisting of:
Wherein,,
R A1 represents a linear or branched alkyl group having 1 to 8 carbon atoms,
Wherein one or not adjacent two or more of the straight-chain or branched alkyl groups having 1 to 8 carbon atoms are-CH 2 -can be replaced independently of each other by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-, and one or more-H present in these groups can be replaced independently of each other by-F or-Cl;
R v and R is w Each independently represents-CH 2 -or-O-;
L A11 、L A12 、L A11 ’、L A12 ’、L A14 、L A15 and L A16 Each independently represents-H or-F;
L A13 and L A13 ' each independently represents-H or-CH 3 ；
X A1 representing-F, -CF 3 or-OCF 3 The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with
v and w each independently represent 0 or 1.
4. The liquid crystal composition according to claim 1, wherein the compound of formula a-2 is selected from the group consisting of:
Wherein,,
R A2 represents a linear or branched alkyl group having 1 to 8 carbon atoms, wherein one or not adjacent two or more-CH groups in the linear or branched alkyl group having 1 to 8 carbon atoms 2 -can be replaced independently of each other by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-, and one or more-H present in these groups can be replaced independently of each other by-F or-Cl;
L A21 、L A22 、L A23 、L A24 and L A25 Each independently represents-H or-F; and is also provided with
X A2 representing-F, -CF 3 、-OCF 3 or-CH 2 CH 2 CH＝CF 2 。
5. The liquid crystal composition according to claim 1, further comprising at least one compound of formula M:
wherein,,
R M1 and R is M2 Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Wherein one or not adjacent two or more of the straight-chain or branched alkyl groups having 1 to 12 carbon atoms are-CH 2 -can be replaced independently of each other by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
ring(s)
Ring->
And (C) a ring->
Each independently represents->
Wherein->
One or more of-CH 2 -can be replaced by-O-, single bonds in one or more rings can be replaced by double bonds, wherein +.>
Can be substituted by halogen;
Z M1 and Z M2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-C≡C-、-CH＝CH-、-CH 2 CH 2 -or- (CH) 2 ) 4 -; and is also provided with
n M Represents 0, 1 or 2, wherein when n M When=2, the ring
Identical or different, Z M2 The same or different.
6. The liquid crystal composition according to claim 5, wherein the compound of formula M is selected from the group consisting of:
7. The liquid crystal composition of claim 5, further comprising at least one compound of formula N:
wherein,,
R N1 and R is N2 Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Wherein one or not adjacent two or more of the straight-chain or branched alkyl groups having 1 to 12 carbon atoms are-CH 2 -can be replaced independently of each other by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
ring(s)
And (C) a ring->
Each independently represents->
Wherein the method comprises the steps of
One or more of-CH 2 Can be-O-substitution, one or more single bonds in the ring can be replaced by double bonds, wherein +.>
Wherein-ch=in one or more rings can be replaced by-n=;
Z N1 and Z N2 Each independently represents a single bond, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -、-(CH 2 ) 4 -、-CF 2 O-or-OCF 2 -；
L N1 And L N2 Independently of each other, -H, alkyl having 1 to 3 carbon atoms or halogen; and is also provided with
n N1 Represents 0, 1, 2 or 3, n N2 Represents 0 or 1, and 0.ltoreq.n N1 +n N2 Not more than 3, wherein when n N1 When=2 or 3, the ring
Identical or different, Z N1 The same or different.
8. The liquid crystal composition according to claim 7, wherein the compound of formula N is selected from the group consisting of:
9. The liquid crystal composition of claim 5, further comprising at least one compound of formula B:
wherein,,
R B1 and R is B2 Each independently represents halogen, -CF 3 、-OCF 3 A linear or branched alkyl group having 1 to 12 carbon atoms,
Wherein said straight or branched alkyl group having 1 to 12 carbon atoms,/or->
One or not adjacent two or more-CH 2 -can be replaced independently of each other by-c≡c-, -O-, -CO-O-or-O-CO-;
ring(s)
And (C) a ring->
Each independently represents->
/>
Wherein->
One or more of-CH 2 -can be replaced by-O-, single bonds in one or more rings can be replaced by double bonds, wherein +.>
Wherein-ch=may be replaced by-n=in one or more rings, each independently being capable of being replaced by-CN, -F or-Cl;
X B representation-O-, O- -S-or-CO-;
L B1 and L B2 Each independently represents-H, -F, -Cl, -CF 3 or-OCF 3 ；
Z B1 And Z B2 Each independently represents a single bond, -O-, -CO-O-, -O-CO-, -CH 2 O-、-OCH 2 -、-CH＝CH-、-C≡C-、-CH 2 CH 2 -、-CF 2 CF 2 -、-(CH 2 ) 4 -、-CF 2 O-or-OCF 2 -; and is also provided with
n B1 And n B2 Each independently represents 0, 1 or 2, wherein when n B1 When 2 is represented, the ring
Identical or different, where when n B2 When 2 is indicated, the ring->
Identical or different, Z F2 The same or different.
10. The liquid crystal composition according to claim 9, wherein the compound of formula F is 0.1 to 30% by weight of the liquid crystal composition, and the compound selected from the group consisting of the compounds of formula a-1 and formula a-2 is 0.1 to 50% by weight of the liquid crystal composition; the compound of the general formula M accounts for 0.1-60% of the weight of the liquid crystal composition, the compound of the general formula N accounts for 0.1-40% of the weight of the liquid crystal composition, and the compound of the general formula B accounts for 0.1-30% of the weight of the liquid crystal composition.
11. A liquid crystal display device comprising the liquid crystal composition of any one of claims 1-10.
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| CN110023457A (en) * | 2016-11-18 | 2019-07-16 | 默克专利股份有限公司 | Liquid crystal media and liquid crystal display comprising it |
| CN110300746A (en) * | 2017-02-27 | 2019-10-01 | 捷恩智株式会社 | Compound, liquid-crystal composition and liquid crystal display element with dibenzofurans ring |
| CN110396411A (en) * | 2019-08-06 | 2019-11-01 | 晶美晟光电材料（南京）有限公司 | A kind of liquid-crystal composition and its application with negative permittivity |
| JP2021028299A (en) * | 2017-11-30 | 2021-02-25 | Jnc株式会社 | Compound having dibenzothiophene ring, liquid crystal composition and liquid crystal display element |
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| CN110023457A (en) * | 2016-11-18 | 2019-07-16 | 默克专利股份有限公司 | Liquid crystal media and liquid crystal display comprising it |
| CN110300746A (en) * | 2017-02-27 | 2019-10-01 | 捷恩智株式会社 | Compound, liquid-crystal composition and liquid crystal display element with dibenzofurans ring |
| JP2021028299A (en) * | 2017-11-30 | 2021-02-25 | Jnc株式会社 | Compound having dibenzothiophene ring, liquid crystal composition and liquid crystal display element |
| CN110396411A (en) * | 2019-08-06 | 2019-11-01 | 晶美晟光电材料（南京）有限公司 | A kind of liquid-crystal composition and its application with negative permittivity |
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