CN110964539B - Liquid crystal composition, high molecular liquid crystal alignment polymer, liquid crystal display element and liquid crystal display - Google Patents
Liquid crystal composition, high molecular liquid crystal alignment polymer, liquid crystal display element and liquid crystal display Download PDFInfo
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Abstract
The invention provides a liquid crystal composition, a high molecular liquid crystal alignment polymer, a liquid crystal display element and a liquid crystal display. The liquid crystal composition of the invention contains one or more compounds shown as a formula I and one or more compounds shown as a formula II as polymerizable components. The polymerizable group can generate polymerization reaction to form a polymer film with vertical alignment effect, so that the traditional alignment layer is replaced to align the liquid crystal molecules, and the liquid crystal molecules are orderly arranged.
Description
Technical Field
The invention relates to the technical field of liquid crystal display. And more particularly, to a liquid crystal composition, a liquid crystal display element, or a liquid crystal display.
Background
With the development of Display technology, flat panel Display devices such as Liquid Crystal Display (LCD) devices have advantages of high image quality, power saving, thin body, and wide application range, and thus are widely used in various consumer electronics products such as mobile phones, televisions, personal digital assistants, digital cameras, notebook computers, and desktop computers, and are becoming the mainstream of Display devices.
Currently, in a commonly used Liquid Crystal Display (LCD), a color filter substrate and a TFT substrate are respectively provided with a layer of thin film material, which is mainly used to align liquid crystal molecules in a certain direction, and is called as an alignment layer. Such alignment layers are mainly classified into a rubbing alignment type and a photo alignment type. The alignment layer has the characteristics of uniformity, adherence and stability.
However, alignment layers also have certain disadvantages. Firstly, the rubbing alignment layer is easy to cause the problems of dust particles, static residues, brush marks and the like in the display process of the liquid crystal display device so as to reduce the manufacturing yield of the liquid crystal display device, while the photo-alignment layer can avoid the problems, but the photo-alignment layer is limited in material characteristics, poor in heat resistance and ageing resistance and weak in liquid crystal molecule anchoring capability, so that the display effect of the liquid crystal display device is influenced; secondly, the process of forming the alignment layer on the TFT-LCD is also complicated, which results in an increase in the production cost of the liquid crystal display device.
Disclosure of Invention
The present inventors have conducted extensive studies in order to obtain a liquid crystal composition for a liquid crystal display device capable of aligning liquid crystal molecules in a certain direction without using an alignment layer, in order to overcome the problem of high manufacturing cost caused by the manufacturing of the alignment layer, and have found that the object can be achieved by the liquid crystal composition of the present invention, thereby completing the present invention. Specifically, the present invention comprises the following:
in a first aspect of the invention, a liquid crystal composition is provided, which comprises one or more compounds of formula I, one or more compounds of formula II,
in the formula I, the compound is shown in the specification,
R 5 represents an alkyl group having 1 to 10 carbon atoms, a fluorine substituentAn alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 5 Any one or more of the radicals indicated being unconnected-CH 2 -may each independently be optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z 3 represents a single bond, -COO-, -CH 2 O-or-CH 2 CH 2 -;
Each independently represents cyclohexylene, phenylene, or phenylene optionally substituted by Cl, F, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, wherein the alkyl group having 1 to 12 carbon atoms or the alkoxy group having 1 to 12 carbon atoms is not adjacent to one or more of-CH 2 The radical-being optionally substituted by-O-, -CH 2 =CH 2 -, -CO-, - -OCO-or-COO-substitution;
Sp 1 each independently represents a spacer;
P 1 each independently represents H or a polymerizable group, and P 1 At least one of them represents a polymerizable group;
m 1 denotes 0 or 1,n 1 Represents 1, 2 or 3,r represents 1, 2 or 3;
in the formula II, the reaction solution is shown in the specification,
Sp 2 、Sp 3 、Sp 4 each independently represents a spacer group, P 2 、P 3 、P 4 Each independently represents a polymerizable group;
R 61 、R 62 、R 63 each independently represents-OH, -NH 2 Or, -CH 3 And at least one represents-OH;
Z 4 、Z 5 each independently represents-CH 2 -, -CH-, or, -C-;
q represents an integer of 0 to 10, r 1 、r 2 、r 3 、r 4 、r 5 、r 6 Each independently represents 0 or 1, and Z 4 represents-CH 2 Time of flight r 1 +r 2 +r 3 =1,Z 4 represents-CH-time r 1 +r 2 +r 3 =2,Z 4 represents-C-time r 1 +r 2 +r 3 =3;Z 5 represents-CH 2 -time r 4 +r 5 +r 6 =1,Z 4 represents-CH-time r 4 +r 5 +r 6 =2,Z 4 represents-C-time r 4 +r 5 +r 6 =3。
In a second aspect of the present invention, a polymer liquid crystal alignment polymer is provided, which is obtained by performing a polymerization reaction on the liquid crystal composition.
In a third aspect of the present invention, a liquid crystal display element or a liquid crystal display is provided, which comprises the above liquid crystal composition or the above polymeric liquid crystal alignment polymer, and the display element or the display is an active matrix display element or a display or a passive matrix display element or a display.
The liquid crystal composition provided by the invention contains the compound shown in the formula I and the compound shown in the formula II, so that a high-molecular liquid crystal alignment polymer with a vertical alignment effect can be formed in a liquid crystal display element or a liquid crystal display through polymerization of the compound shown in the formula I and the compound shown in the formula II, and the traditional alignment layer is replaced to align liquid crystal molecules, so that the liquid crystal molecules are orderly arranged; the liquid crystal display element or the liquid crystal display adopting the liquid crystal composition does not need to be additionally provided with a traditional alignment layer, so that the problems of poor yield, poor heat resistance and poor aging resistance of a liquid crystal display device and the like caused by dust particles, static residues, brush marks and the like caused by the arrangement of the alignment layer can be avoided, and the preparation process of the liquid crystal display element or the liquid crystal display is effectively simplified, thereby improving the production efficiency and reducing the production cost. In addition, the liquid crystal display element or the liquid crystal display obtained by the liquid crystal composition has the characteristics of wide nematic phase temperature range, proper or higher birefringence anisotropy delta n and high charge retention rate.
Detailed Description
[ liquid Crystal composition ]
A liquid crystal composition as one aspect of the present invention comprises one or more compounds represented by formula I, one or more compounds represented by formula II,
in the formula I, the raw materials are mixed,
R 5 represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 5 Any one or more of the radicals indicated being unconnected-CH 2 -may each independently be optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z 3 represents a single bond, -COO-, -CH 2 O-or-CH 2 CH 2 -;
Each independently represents cyclohexylene, phenylene, or phenylene optionally substituted by Cl, F, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, wherein the alkyl group having 1 to 12 carbon atoms or the alkoxy group having 1 to 12 carbon atoms is not adjacent to one or more of-CH 2 The radical-being optionally substituted by-O-, -CH 2 =CH 2 -, -CO-, - -OCO-or-COO-substitution;
Sp 1 each independently represents a spacer;
P 1 each independently represents H or a polymerizable group, and P 1 At least one of themEach represents a polymerizable group;
m 1 denotes 0 or 1,n 1 Represents 1, 2 or 3,r represents 1, 2 or 3;
in the formula II, the reaction mixture is shown in the specification,
Sp 2 、Sp 3 、Sp 4 each independently represents a spacer group, P 2 、P 3 、P 4 Each independently represents a polymerizable group;
R 61 、R 62 、R 63 each independently represents-OH, -NH 2 Or, -CH 3 And at least one represents-OH;
Z 4 、Z 5 each independently represents-CH 2 -, -CH-, or-C-;
q represents an integer of 0 to 10, r 1 、r 2 、r 3 、r 4 、r 5 、r 6 Each independently represents 0 or 1, and Z 4 represents-CH 2 Time of flight r 1 +r 2 +r 3 =1,Z 4 represents-CH-time r 1 +r 2 +r 3 =2,Z 4 represents-C-time r 1 +r 2 +r 3 =3;Z 5 represents-CH 2 Time of flight r 4 +r 5 +r 6 =1,Z 4 represents-CH-time r 4 +r 5 +r 6 =2,Z 4 represents-C-time r 4 +r 5 +r 6 =3。
In the compound shown in the formula II R 61 、R 62 、R 63 The group acts as an anchor group which can be adsorbed to a liquid crystal display element or a liquid crystal display substrate to perform a fixing function, and R in the compound represented by the formula II is used in the manufacturing process of the liquid crystal display element or the liquid crystal display 61 、R 62 、R 63 Can be adsorbed and fixed with the substrate to form a uniform film; and the polymerizable group P at the other end of the compound of the formula II 2 、P 3 、P 4 Can generate copolymerization reaction with the polymerizable group of the compound shown in the formula I to form a polymer film with vertical alignment effect, thereby replacing the traditional alignment layer to carry out liquid crystal molecule polymerizationAnd aligning to make the liquid crystal molecules orderly arranged. Therefore, the problems of poor yield, poor heat resistance and aging resistance and the like of a liquid crystal display device caused by dust particles, static residues, brush marks and the like due to the configuration of an alignment layer can be avoided, and the preparation process of a liquid crystal display element or a liquid crystal display is effectively simplified, so that the production efficiency can be improved, and the production cost can be reduced. In addition, the liquid crystal display element or the liquid crystal display obtained by the liquid crystal composition has the characteristics of wide nematic phase temperature range, proper or higher birefringence anisotropy delta n and high charge retention rate.
The "spacer" in the present invention means a chain-like group, preferably a branched or straight-chain alkyl group having 1 to 10 carbon atoms, wherein-CH is optionally disconnected in the alkyl group 2 -optionally substituted by-O-.
P 1 、P 2 、P 3 、P 4 When representing a polymerizable group, a methacrylate group, an acrylate group, a vinyl group or an ethylene oxide group is preferable. The methacrylate group is more preferable.
In the liquid crystal composition, the total mass percentage of the compound represented by the formula I and the compound represented by the formula II in the liquid crystal composition is preferably 0.1 to 3%, and more preferably 0.5 to 1.5%, in view of obtaining an alignment effect equivalent to that of an alignment layer by the thickness of a polymer liquid crystal alignment polymer film formed by polymerizing the compounds represented by the formulae I and II in the liquid crystal composition being 50nm to 120 nm. In addition, from the viewpoint of obtaining an excellent polymer liquid crystal alignment polymer film, the content ratio of the compound represented by the formula I to the compound represented by the formula II in percentage by mass is preferably 1.5 to 1:1.
In some embodiments of the liquid crystal composition of the present invention, preferably, Z 3 Represents a single bond.
In some embodiments of the liquid crystal compositions of the present invention, optionally,each independently represents a cyclohexylene group or a phenylene group. Starting from the degree of conjugation of the ring structure,more preferably, each independently represents a phenylene group.
When the liquid crystal composition is used in a liquid crystal display device, the compound shown in the formula I and the compound shown in the formula II can be irradiated by energy light to generate a polymerization reaction so as to form a high-molecular liquid crystal alignment polymer, and the energy light reaction can be visible light or ultraviolet light. In view of the relationship between the degree of conjugation of the compound of formula I and the amount of light energy absorbed, the higher the degree of conjugation of the compound of formula I, the more light energy absorbed, the higher the efficiency of light energy conversion, and the easier the compound of formula I polymerizes with the compound of formula II, in which formula I, m 1 And n 1 The sum of (a) and (b) is preferably 2 or more; in addition, from the viewpoint of solubility of the compound represented by the formula I in a liquid crystal composition, the more ring structures the compound represented by the formula I has, the poorer the mutual solubility thereof, and therefore, m 1 And n 1 The sum of (a) and (b) is preferably 4 or less.
In the liquid-crystal compositions of the invention, the aforementioned one or more compounds of the formula I are preferably selected from the group consisting of I1 to I12,
the process for producing a liquid crystal display element or a liquid crystal display using the liquid crystal composition of the present invention needs to be carried out in a vacuum atmosphere, and q is preferably an integer of 2 to 10 from the viewpoint that the compound represented by formula II is not easily volatilized during the production of the liquid crystal display element or the liquid crystal display. The boiling point of the compound represented by the formula II is proportional to the number of carbon atoms thereof, and when q is 2 or more, the compound represented by the formula II is less likely to volatilize.
In the liquid crystal composition of the present invention, preferably, the aforementioned one or more compounds represented by formula II are selected from the group consisting of II1 to II6,
the liquid crystal composition of the invention can optionally further comprise one or more compounds shown in a formula III and one or more compounds shown in a formula IV,
in the formula III, R 1 、R 2 Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 8 carbon atoms;
In the formula IV, R 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more of the groups shown are not linked to-CH 2 -each independently is optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -or-CH 2 O-;
Each independently represents 1,4-phenylene, 1,4-cyclohexylene, fluoro 1,4-phenylene or 1,4-cyclohexenylene;
m represents 1 or 2;
n represents 0, 1 or 2.
The compound shown in the formula III has the characteristics of low rotational viscosity and good intersolubility with other compounds. The lower rotational viscosity is more favorable for improving the response speed of the liquid crystal composition. The compound shown in the formula IV is negative dielectric anisotropy, and the driving voltage of the liquid crystal composition is adjusted by the compound shown in the formula IV.
As R in the aforementioned formula IV 3 、R 4 One or more disconnected-CH in the alkyl with 1-10 carbon atoms 2 Examples of the group substituted with a cyclopropylene, a cyclobutylene or a cyclopentylene group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a methylcyclopropylene group, an ethylcyclopropylene group, a propylcyclopropylene group, an isopropylcyclopropylene group, a n-butylcyclopropylene group, an isobutylcyclopropylene group, a tert-butylcyclopropylene group, a methylcyclobutylene group, an ethylcyclobutylene group, a propylbutylene group, an isopropylcyclobutylene group, a n-butylbutylene group, an isobutylcyclobutylene group, a tert-butylcyclobutylene group, a methylcyclopentylene group, an ethylcyclopentylene group, a propylcyclopentylene group, an isopropylcyclopentylene group, a n-butylcyclopentylene group and an isobutylcyclopentylene group. R 3 、R 4 Among the groups shown, preferred from the viewpoint of rotational viscosity, solubility and clearing point of the liquid crystal compound is cyclopropyl, cyclobutyl or cyclopentyl.
The liquid crystal composition of the present invention is preferably a negative dielectric anisotropic liquid crystal composition.
When the liquid crystal composition of the present invention contains the compound represented by the formula III, the total content of the compound represented by the formula III in the liquid crystal composition of the present invention is preferably 5 to 60% by mass, and more preferably 10 to 40% by mass; when the liquid crystal composition of the present invention contains the compound represented by the formula IV, the total content of the compound represented by the formula IV in the liquid crystal composition of the present invention is preferably 25 to 90% by mass, and more preferably 40 to 65% by mass.
The aforementioned one or more compounds represented by formula III are preferably selected from the group consisting of compounds represented by formulae III 1 to III 16;
the aforementioned one or more compounds of formula IV are preferably selected from the group consisting of compounds of formulae IV1-IV 14;
wherein the content of the first and second substances,
r in the compounds of formulae IV1-IV14 3 、R 4 With R in the compound of the formula IV 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R is 3 、R 4 Any one or more of the radicals indicated being unconnected-CH 2 -optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene.
In one embodiment of the liquid crystal composition of the present invention, optionally, the liquid crystal composition may further include one or more compounds represented by formula V.
Wherein R is 9 、R 10 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 9 、R 10 Any one or more of the radicals indicated being unconnected-CH 2 -each independently is optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
x represents O, S or-CH 2 O-。
By adding the compound shown in the formula V into the liquid crystal composition, the liquid crystal composition has large negative dielectric anisotropy, and is favorable for reducing the driving voltage of a device. When the liquid crystal composition of the present invention contains the compound represented by formula V, the total content of the compounds represented by formula V in the liquid crystal composition is preferably 1 to 20% by mass, and more preferably 5 to 15% by mass.
Preferably, the aforementioned one or more compounds of formula V are selected from the group consisting of compounds of formulae V1-V6,
wherein R is 101 Each independently represents an alkyl group having 2 to 6 carbon atoms.
In some embodiments, the liquid crystal composition of the present invention may optionally further comprise one or more compounds represented by formula vi:
wherein R is 11 、R 12 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 11 、R 12 Any one or more of the radicals indicated being unconnected-CH 2 -each independently is optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
The aforementioned one or more compounds of formula VI are preferably selected from the group consisting of compounds of formulae VI 1 to VI 6,
wherein R is 121 Represents an alkyl group having 1 to 6 carbon atoms, R 122 Represents an alkoxy group having 1 to 6 carbon atoms, R 111 Represents an alkyl group having 2 to 6 carbon atoms, R 112 Represents an alkenyl group having 2 to 6 carbon atoms.
The terminal chain of the compound shown in the formula VI is R 112 When the alkenyl group is represented, the liquid crystal compound has a higher clearing point and an elastic constant, particularly a splay elastic constant K 33 And is beneficial to improving the parameter performance of the liquid crystal composition.
When the liquid crystal composition of the present invention contains the compounds represented by the formula VI, the total content of the compounds represented by the formula VI in the liquid crystal composition is preferably 1 to 40% by mass, and more preferably 5 to 20% by mass.
In some embodiments of the liquid crystal compositions of the present invention, one or more compounds of formula VII may optionally be included:
wherein R is 13 、R 14 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
F 1 、F 2 、F 3 Each independently represents H or F, and F 2 、F 3 Not simultaneously F.
The aforementioned compound represented by the formula VII is preferably one or more compounds selected from the group consisting of compounds represented by the formulae VII 1 to VII 4:
wherein R is 131 、R 141 Each independently represents an alkyl group having 1 to 6 carbon atoms.
The compounds represented by the above formulas VII 1 to VII 4 have high clearing points, generally higher than 200 ℃, and the clearing points of the liquid crystal composition can be improved more remarkably by containing the compounds represented by the formulas VII 1 to VII 4 in the liquid crystal composition.
When the liquid crystal composition of the present invention contains the compound represented by the formula VII, the total content of the compounds represented by the formula VII in the liquid crystal composition is preferably 1 to 10% by mass, and more preferably 2 to 5% by mass.
In some embodiments of the liquid crystal composition of the present invention, optionally, a compound of formula VIII,
in the formula VIII, R 7 、R 8 Each independently represents P 3 -Sp 3 -, H, cl, F, or an alkyl group having 1 to 12 carbon atoms; one or more non-adjacent-CH in the alkyl with the carbon atom number of 1-12 2 The radical-being optionally substituted by-O-, -CH 2 =CH 2 -, -CO-, - -OCO-or-COO-substitution; wherein R is 7 、R 8 At least one of them represents P 3 -Sp 3 -;
Each independently represents phenylene, optionally substituted by P 3 -Sp 3 -, cl, F, alkyl with 1-12 carbon atoms, phenylene or indanyl substituted by alkoxy with 1-12 carbon atoms, wherein one or two non-adjacent-CH in the alkyl with 1-12 carbon atoms and the alkoxy with 1-12 carbon atoms 2 The radical being optionally substituted by-O-, -CH 2 =CH 2 -, -CO-, - -OCO-or-COO-substitution, and isAnd R 7 In thatIs bonded at any position of the first and second substrates,and R 8 In thatBonding at any position of (a);
s represents 0, 1 or 2;
P 3 represents a polymerizable group; sp 3 Represents a spacer group;
Z 4 represents a single bond, -COO-, -CH 2 O-or-CH 2 CH 2 -。
The compound represented by the formula viii is a polymerizable compound and functions as a Reactive Mesogen (RM), and examples of the compound represented by the formula viii include one or a combination of plural kinds of acrylate, acrylate derivative, methacrylate derivative, styrene derivative, and epoxy resin. Under the condition that the compound shown in the formula VIII is a biphenyl or terphenyl structure, because light energy absorbed by the compound is required to be distributed to polymerizable groups at two ends, the polymerization speed of the compound shown in the formula VIII is lower than that of the compound shown in the formula I, namely after the compound shown in the formula I and the compound shown in the formula II are polymerized, the compound shown in the formula VIII is polymerized with the compound shown in the formula I and/or the compound shown in the formula II, the compound shown in the formula I and/or the compound shown in the formula II are further fixed, the continuous stable pre-tilt effect is provided, and the pre-tilt of liquid crystal molecules is very favorable for improving the response speed of liquid crystals under an electric field.
The compound of formula VIII is further preferably selected from the group consisting of compounds of formulae VIII 1 to VIII 8,
in the liquid crystal composition of the present invention, when the compound represented by the formula VIII is contained, the total amount of the compounds represented by the formula VIII is contained in the liquid crystal composition in an amount of 0.01 to 1% by mass, preferably 0.03 to 0.5% by mass. From the viewpoint of further reducing the defective display of afterimages in the liquid crystal display device, the content of the compound represented by the formula viii is preferably 1% or less, and more preferably 0.5% or less. The content of the compound represented by the formula VIII is preferably 0.01% or more, more preferably 0.03% or more, from the viewpoint of forming a polymer thin film by polymerization with a self-aligning agent to align liquid crystal molecules.
In the liquid crystal composition of the present invention, a dopant having various functions may be optionally added, and when a dopant is contained, the content of the dopant is preferably 0.01 to 1% by mass in the liquid crystal composition, and examples of the dopant include an antioxidant, an ultraviolet absorber, and a chiral agent.
Examples of the antioxidant and ultraviolet absorber include:
t represents an integer of 1 to 10.
[ high molecular liquid Crystal alignment Polymer ]
The polymer liquid crystal alignment polymer as one aspect of the present invention is obtained by subjecting the liquid crystal composition of the present invention described above to a polymerization reaction.
The liquid crystal composition contains polymerizable components such as a compound shown in a formula I and a compound shown in a formula II. When a liquid crystal display device is manufactured, a liquid crystal accommodating space is formed between two parallel substrates, the liquid crystal composition is sealed in the accommodating space, and the liquid crystal composition is irradiated by energy light irradiation and the like, so that polymerizable components in the liquid crystal composition are subjected to polymerization reaction to obtain the high molecular liquid crystal alignment polymer. In the process of fabricating a liquid crystal display device, R in the compound of formula II 61 、R 62 、R 63 The group can be used as an anchoring group which can be adsorbed to a liquid crystal display element or a liquid crystal display substrate to play a role in fixing, and is adsorbed and fixed with the substrate to form a uniform film; and the polymerizable group P at the other end of the compound of the formula II 2 、P 3 、P 4 Can generate polymerization reaction with the polymerizable group of the compound shown in the formula I to form a polymer film with vertical alignment effectSo as to replace the traditional alignment layer to align the liquid crystal molecules and make the liquid crystal molecules orderly arranged. Therefore, the problems of poor yield of the liquid crystal display device, poor heat resistance and aging resistance and the like caused by dust particles, static residues, brush marks and the like caused by the configuration of the alignment layer can be avoided, and the preparation process of the liquid crystal display element or the liquid crystal display is effectively simplified, so that the production efficiency can be improved, and the production cost can be reduced.
As mentioned above, the liquid crystal composition of the present invention may further comprise other polymerizable compounds than the compound represented by formula I and the compound represented by formula II, such as the compound represented by formula VIII. In the case of containing other polymerizable compounds such as the compound shown in the formula VIII, the compound shown in the formula VIII is polymerized with the compound shown in the formula I and/or the compound shown in the formula II to further fix the compound shown in the formula I and/or the compound shown in the formula II and provide a continuous stable pretilt effect, and the pretilt of liquid crystal molecules is very favorable for improving the response speed of liquid crystals under an electric field.
As the thickness of the polymeric liquid crystal alignment polymer of the present invention, the thickness of the polymeric liquid crystal alignment polymer film is between 50nm and 120nm in view of obtaining an alignment effect equivalent to that of the alignment layer.
The energy light may be visible light, ultraviolet light, or the like.
[ liquid Crystal display element or liquid Crystal display ]
In another aspect of the present invention, a liquid crystal display device or a liquid crystal display includes the liquid crystal composition or the polymer liquid crystal alignment polymer, and the display device or the display is an active matrix display device or a display or a passive matrix display device or a display.
Preferably, the liquid crystal display element or the liquid crystal display is an active matrix addressed liquid crystal display element or a liquid crystal display.
Preferably, the active matrix display element or display is in particular a liquid crystal display element or a liquid crystal display without alignment layers.
As a method for producing a liquid crystal display element or a liquid crystal display device of the present invention, the following method can be employed: first, two corresponding transparent substrates are disposed in parallel, the transparent substrates may be made of glass, adaptive or soft plastic such as PET, and the two transparent substrates are separated by a plurality of support pillars to form a liquid crystal accommodating space. The liquid crystal composition is sealed in the liquid crystal accommodating space by adopting a pouring method or a liquid crystal dripping method.
Then, the liquid crystal composition is irradiated with energy light rays, and a high molecular liquid crystal alignment polymer is formed on the surface of the transparent substrate corresponding to the liquid crystal accommodating space. The energy light may be visible light, ultraviolet light, or the like. The polymer liquid crystal alignment polymer is a polymer film with a vertical alignment effect, and can replace a traditional alignment layer to align liquid crystal molecules, so that the liquid crystal molecules are arranged in order. Therefore, the problems of poor yield of the liquid crystal display device, poor heat resistance and aging resistance and the like caused by dust particles, static residues, brush marks and the like caused by the configuration of the alignment layer can be avoided, and the preparation process of the liquid crystal display element or the liquid crystal display is effectively simplified, so that the production efficiency can be improved, and the production cost can be reduced.
Examples
In order to more clearly illustrate the present invention, the present invention is further described below in conjunction with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method unless otherwise specified, the used raw materials can be obtained from a public commercial way unless otherwise specified, the percentages refer to mass percentages, the temperature is centigrade (DEG C), the liquid crystal compound also becomes a liquid crystal monomer, and the specific meanings and test conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
Δ n denotes optical anisotropy, Δ n = n e -n o Wherein n is o Refractive index of ordinary light, n e Is remarkable inThe refractive index of light is tested by an Abbe refractometer under the test conditions of 25 +/-2 ℃ and 589 nm;
Δ ε represents the dielectric anisotropy, Δ ε = ε/ε ^ where ε/is the dielectric constant parallel to the molecular axis,. Epsilon. Is the dielectric constant perpendicular to the molecular axis, the test conditions were 25. + -. 0.5 ℃,20 micron parallel cell, INSTEC: ALCT-IR1 test;
γ 1 represents rotational viscosity (mPas) and the test conditions are 25. + -. 0.5 ℃ in 20 μm parallel cells, INSTEC: ALCT-IR1 test.
Examples 1 to 15 and comparative example 1:
the liquid crystal composition was prepared according to the composition and the ratio described below, and a polymer liquid crystal alignment polymer and a liquid crystal display device were produced.
The preparation method of the liquid crystal composition comprises the following steps: weighing each liquid crystal monomer according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker filled with each liquid crystal monomer on a magnetic stirring instrument for heating and melting, adding a magnetic rotor into the stainless steel beaker after most of the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The preparation method of the high-molecular liquid crystal alignment polymer and the liquid crystal display element comprises the following steps: firstly, two transparent glass substrates are arranged in parallel, the two transparent glass substrates are separated by a plurality of support columns to form a liquid crystal accommodating space, and the liquid crystal composition is sealed in the liquid crystal accommodating space by adopting a perfusion method. And then, irradiating the liquid crystal composition by adopting ultraviolet light to enable the polymerizable compound in the liquid crystal composition to generate polymerization reaction, and forming a high-molecular liquid crystal alignment polymer on the surface of the glass transparent substrate corresponding to the liquid crystal accommodating space, thereby obtaining the liquid crystal display element.
Then, the properties of the liquid crystal display element after the polymerization reaction were measured.
The liquid crystal monomer structure used in the embodiment of the invention is represented by codes, and the code representation methods of the liquid crystal ring structure, the end group and the connecting group are shown in the following tables 1 and 2.
Corresponding code of the ring structure of Table 1
TABLE 2 corresponding codes for end groups and linking groups
Examples are:
Example 1:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 3 below.
TABLE 3 formulation of liquid crystal compositions and corresponding Properties
Example 2:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 4 below.
TABLE 4 formulation of liquid crystal compositions and corresponding Properties
Example 3:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 5 below.
TABLE 5 formulation of liquid crystal compositions and corresponding Properties
Example 4:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 6 below.
TABLE 6 formulation of liquid crystal compositions and corresponding Properties
Example 5:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 7 below.
TABLE 7 formulation of liquid crystal compositions and corresponding Properties
Example 6:
the formulation and corresponding properties of the liquid crystal composition are shown in Table 8 below.
TABLE 8 formulation of liquid crystal compositions and corresponding Properties
Example 7:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 9 below.
TABLE 9 formulation of liquid crystal compositions and corresponding Properties
Example 8:
the formulation of the liquid crystal composition and the corresponding properties are shown in table 10 below.
TABLE 10 formulation of liquid crystal compositions and corresponding Properties
Example 9:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 11 below.
TABLE 11 formulation of liquid crystal compositions and corresponding Properties
Example 10:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 12 below.
TABLE 12 formulation of liquid crystal compositions and corresponding Properties
Example 11:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 13 below.
TABLE 13 formulation of liquid crystal compositions and corresponding Properties
Example 12:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 14 below.
TABLE 14 formulation of liquid crystal compositions and corresponding Properties
Example 13:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 15 below.
TABLE 15 formulation of liquid crystal compositions and corresponding Properties
Example 14:
the formulation of the liquid crystal composition and the corresponding properties are shown in Table 16 below.
TABLE 16 formulation of liquid crystal compositions and corresponding Properties
Example 15:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 17 below.
TABLE 17 formulation of liquid crystal compositions and corresponding Properties
Comparative example 1:
the liquid crystal composition of comparative example 1 was obtained in the same manner as in example 15 except that a compound represented by the formula IX was used in place of the compound represented by the formula I3 in example 15.
The formulation and corresponding properties of the liquid crystal composition of comparative example 1 are shown in table 18 below.
TABLE 18 formulation of liquid crystal compositions and corresponding Properties
Since the compound shown in the formula I3 is a compound with a polymerizable group at only one end, after the polymerization group of the compound shown in the formula I3 is polymerized with the polymerization group of the compound shown in the formula II6, the compound shown in the formula I3 can form a larger inclination angle perpendicular to the inner surface of a liquid crystal display element or a liquid crystal display substrate, so that a polymer film formed by polymerizing the compound shown in the formula I3 and the compound shown in the formula II6 has a vertical alignment effect, and a stable pretilt is provided for the liquid crystal composition. However, since the compound of the formula IX is a compound having polymerizable groups at both ends, when the compound of the formula IX is polymerized with the compound of the formula II6, there occurs a high probability that the polymerizable groups at both ends of the compound of the formula IX are respectively polymerized with the polymerizable groups of the compound of the formula II6 so that the compound of the formula IX is parallel to the inner surface of the liquid crystal display element or the liquid crystal display substrate, and thus a polymer film formed by polymerizing the compound of the formula IX with the compound of the formula II6 cannot perform an alignment function or is poor in an alignment effect.
Claims (14)
1. A liquid crystal composition, which comprises one or more compounds represented by formula I, one or more compounds represented by formula II1 to formula II6,
in the formula I, the compound is shown in the specification,
R 5 represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R is 5 Any one or more of the radicals indicated being unconnected-CH 2 -may each independently be optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
Z 3 represents a single bond, -COO-, -CH 2 O-or-CH 2 CH 2 -;
Each independently represents cyclohexylene, phenylene, or phenylene optionally substituted by Cl, F, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, wherein one or more of the alkyl group having 1 to 12 carbon atoms and the alkoxy group having 1 to 12 carbon atoms are not adjacent to each other-CH 2 The radical-being optionally substituted by-O-, -CH 2 =CH 2 -, -CO-, - -OCO-or-COO-substitution;
Sp 1 each independently represents a spacer;
P 1 each independently represents H or a polymerizable group, and P 1 At least one of them represents a polymerizable group;
m 1 denotes 0 or 1,n 1 Represents 1, 2, or 3,r represents 1.
2. The liquid crystal composition of claim 1, further comprising one or more compounds of formula III, one or more compounds of formula IV,
in the formula III, R 1 、R 2 Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 8 carbon atoms;
In the formula IV, R 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more of the radicals indicated being unconnected-CH 2 Each independently of the others is optionally substitutedCyclopentylene, cyclobutyl, or cyclopropylene substitution;
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -or-CH 2 O-;
Each independently represents 1,4-phenylene, 1,4-cyclohexylene, fluoro 1,4-phenylene or 1,4-cyclohexenylene;
m represents 1 or 2;
n represents 0, 1, or 2.
4. the liquid crystal composition of claim 2 or 3, wherein the one or more compounds of formula IV are selected from the group consisting of compounds of formulae IV1-IV14,
wherein R is 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine substituentAn alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more of the groups shown are not linked to-CH 2 -each independently is optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene.
5. The liquid crystal composition of claim 1, further comprising one or more compounds of formula V,
wherein R is 9 、R 10 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 9 、R 10 Any one or more of the radicals indicated being unconnected-CH 2 -each independently is optionally substituted with cyclopentylene, cyclobutyl, or cyclopropylene;
x represents O, S or-CH 2 O-。
7. The liquid crystal composition of claim 1, further comprising one or more compounds of formula VI,
wherein R is 11 、R 12 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 11 、R 12 Any one or more of the radicals indicated being unconnected-CH 2 -each independently is optionally substituted with cyclopentylene, cyclobutyl, or cyclopropylene;
8. The liquid crystal composition of claim 1, further comprising one or more compounds of formula VII,
wherein R is 13 And R 14 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
F 1 、F 2 Or F 3 Each independently represents H or F, and F 2 、F 3 Not simultaneously F.
9. The liquid crystal composition of claim 1, further comprising a compound of formula VIII,
in the formula VIII, R 7 、R 8 Each independently represents P 3 -Sp 3 -, H, cl, F, or an alkyl group having 1 to 12 carbon atoms; one or more non-adjacent-CH in the alkyl with the carbon atom number of 1-12 2 The radical-being optionally substituted by-O-, -CH 2 =CH 2 -, -CO-, - -OCO-or-COO-substitution; wherein R is 7 、R 8 At least one of them represents P 3 -Sp 3 -;
Each independently represents phenylene, optionally substituted by P 3 -Sp 3 -, cl, F, alkyl with 1-12 carbon atoms, phenylene or indanyl substituted by alkoxy with 1-12 carbon atoms, wherein one or two non-adjacent-CH in the alkyl with 1-12 carbon atoms and the alkoxy with 1-12 carbon atoms 2 The radical being optionally substituted by-O-, -CH 2 =CH 2 -, -CO-, - -OCO-or-COO-substitution, and isAnd R 7 In thatIs bonded at any position of the first and second substrates,and R 8 In thatBonding at any position of (a);
s represents 0, 1 or 2;
P 3 represents a polymerizable group; sp 3 Represents a spacer group;
Z 4 represents a single bond, -COO-, -CH 2 O-or-CH 2 CH 2 -。
10. A high molecular liquid crystal alignment polymer obtained by subjecting the liquid crystal composition according to any one of claims 1 to 9 to a polymerization reaction.
11. The polymer liquid crystal alignment polymer according to claim 10, which is obtained by polymerizing the compound represented by formula I and the compound represented by formula II in the liquid crystal composition according to any one of claims 1 to 9.
12. A polymeric liquid crystal alignment polymer according to claim 10 or claim 11, wherein the polymerization is carried out by irradiation with energy light.
13. The polymer liquid crystal alignment polymer according to claim 12, wherein the energy light is visible light or ultraviolet light.
14. A liquid crystal display element or a liquid crystal display comprising the liquid crystal composition according to any one of claims 1 to 9 or the polymeric liquid crystal alignment polymer according to any one of claims 10 to 13, wherein the display element or the display is an active matrix display element or a display or a passive matrix display element or a display.
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