CN109575952B - Liquid crystal composition with high transmittance and liquid crystal display device thereof - Google Patents

Liquid crystal composition with high transmittance and liquid crystal display device thereof Download PDF

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CN109575952B
CN109575952B CN201710894136.5A CN201710894136A CN109575952B CN 109575952 B CN109575952 B CN 109575952B CN 201710894136 A CN201710894136 A CN 201710894136A CN 109575952 B CN109575952 B CN 109575952B
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liquid crystal
crystal composition
carbon atoms
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compound
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CN109575952A (en
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马文阳
王立威
徐海彬
韩文明
张文琦
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Jiangsu Hecheng Display Technology Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/46Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells

Abstract

Disclosure of the inventionA liquid crystal composition is provided, the liquid crystal composition comprising: at least one compound of the general formula I; and at least one polymerizable compound of the general formula II. The liquid crystal composition provided by the invention has suitable optical anisotropy and dielectric anisotropy, maintains a relatively high clearing point, and has higher maximum penetration rate and higher contrast. When the liquid crystal composition is applied to a PSVA type liquid crystal display, the liquid crystal composition has an excellent display effect. The invention also provides a liquid crystal display device comprising the liquid crystal composition.

Description

Liquid crystal composition with high transmittance and liquid crystal display device thereof
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition with high transmittance and a liquid crystal display device thereof.
Background
Liquid Crystal Displays (LCDs) have been rapidly developed due to their small size, light weight, low power consumption and excellent Display quality, and are widely used particularly in portable electronic information products, among which active Thin Film Transistor Liquid Crystal displays (TFT-LCDs) are widely used. As for the TFT-LCD display panel currently on the mainstream market, there are three types, which are a Twisted Nematic (TN) or Super Twisted Nematic (STN) type, an In-Plane Switching (IPS) type, and a Vertical Alignment (VA) type.
In the application of liquid crystal display devices, the influence of contrast on visual effect is very critical, generally, the higher the contrast is, the clearer and more striking the image is, and the more vivid and gorgeous the color is; and if the contrast is low, the whole picture is gray. The high contrast ratio is very helpful for the definition, the detail expression and the gray level expression of the image. High contrast products have advantages in black and white contrast, clarity, integrity, etc. The contrast also has a large influence on the display effect of the dynamic video, and because the bright-dark conversion in the dynamic image is relatively fast, the higher the contrast is, the easier the eyes of people can distinguish the conversion process. Among the TFT-LCD display panels, the VA type LCD has a very high Contrast Ratio (CR) compared with other types of LCDs, generally reaching 4000-.
The VA-mode lcd panel has very high contrast because in the dark state without applying electricity, the liquid crystal molecules are aligned perpendicular to the substrate surface, no retardation is generated, the light leakage is very low, the off-state brightness is very low, and the contrast ratio is calculated according to the formula (CR ═ L)255/L0X 100%, wherein L255Is at on-state brightness, L0Off state luminance) is known: the lower the off-state brightness, the higher the contrast. In order to align the liquid crystal molecules in the VA mode lcd panel perpendicular to the substrate surface, a vertical alignment process is required to be performed on the liquid crystal molecules, and the most common practice is to coat a vertical alignment agent (Polyimide, PI solution) on specific areas of the upper and lower substrate surfaces, and then bake the substrate at a certain temperature for a long time to dry the solvent in the alignment agent, thereby forming a PI alignment layer on the substrate surface. Since the VA-mode liquid crystal display panel uses vertically rotating liquid crystals, the difference of birefringence of liquid crystal molecules is large, which causes a problem of color shift (color shift) at a large viewing angle to be serious.
In order to obtain better wide viewing angle characteristics and improve the color shift problem of the VA-type liquid crystal display panel, a multi-domain VA (MVA) technique is generally adopted, in which a sub-pixel is divided into a plurality of regions, and the liquid crystal in each region is tilted in different directions after a voltage is applied, so that the viewing effects in the respective directions tend to be even and uniform. With the development of technology, there has emerged a liquid crystal display panel of the MVA type, called polymer-stabilized vertical alignment (PSVA) type, which does not require the use of a PI alignment layer, by adding a small amount (e.g. 0.3 wt%, more typically < 1 wt%) of one or more polymerizable compounds to the liquid crystal composition and polymerizing or crosslinking it in situ (typically by UV photopolymerization) with or without the application of a voltage between the electrodes after charging the liquid crystal cell. The polymerization is carried out at a temperature at which the liquid-crystalline composition exhibits a liquid-crystalline phase, generally at room temperature. It has proved to be particularly suitable to add polymerizable liquid-crystalline compounds to the liquid-crystalline composition.
The luminance of the liquid crystal display panel is in a linear relationship with the transmittance (T), and the higher the luminance is, the more light is transmitted, that is, the higher the transmittance is, so the above-mentioned contrast calculation formula can be converted into: CR ═ Tmax/TminX 100%, wherein, TmaxDenotes the maximum penetration, TminRepresenting the minimum penetration. As can be seen from the contrast formula, there are two methods for improving the contrast: 1: hoisting Tmax(ii) a 2: reduction of Tmin. While for a PSVA type display device, there is a small TminIs one of the characteristics, TminThe space for further reduction is relatively limited, so by raising TmaxIs a more effective means to improve contrast.
Disclosure of Invention
The purpose of the invention is as follows: in view of the defects of the prior art, the present invention aims to provide a liquid crystal composition having a suitable optical anisotropy, a suitable dielectric anisotropy, and a relatively high maximum transmittance and a higher contrast ratio while maintaining a relatively high clearing point, and a liquid crystal display device comprising the liquid crystal composition.
The technical scheme of the invention is as follows:
one aspect of the present invention provides a liquid crystal composition comprising:
at least one compound of the general formula I
Figure BDA0001421806380000021
At least one polymerizable compound of the general formula II
Figure BDA0001421806380000022
Wherein the content of the first and second substances,
R1and R2Each independently represents-H, -F, alkyl OR alkoxy containing 1-12 carbon atoms, alkenyl OR alkenyloxy containing 2-12 carbon atoms, -OR5OR6
Figure BDA0001421806380000023
Or
Figure BDA0001421806380000024
Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F, and R1And R2At least one of them is-OR5OR6
R5Represents an alkylene group having 1 to 12 carbon atoms or an alkenylene group having 2 to 12 carbon atoms, R6Represents an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms;
L1、L2、L3and L4Each independently represents-F, -Cl, -CN or-NCS;
P1and P2Each independently represent
Figure BDA0001421806380000031
Figure BDA0001421806380000032
Figure BDA0001421806380000033
or-SH;
r1represents 1, 2 or 3;
r2and r3Each independently represents a positive integer of 0 to 6;
r4and r5Each independently represents 0, 1, 2, 3 or 4;
Z1represents a single bond, -CH2CH2-, -COO-, -OCO-, -CH2O-, -OCH 2-or-CH-COO-;
Zp1and Zp2Each independently selected from the group consisting of a single bond, -O-, -S-, -NH-, -NHCOO-, -OCONH-, -CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CF=CH-、-CH=CF-、-CF=CF-、-CO-、-COO-、-OCO-、-OCOO-、-CH2-、-OCH2-、-SCH2-、-CH2S-, -CH ═ CH-, -C ≡ C-, -CH ═ CH-COO-, and-OCO-CH ═ CH-;
Y1and Y2Each independently represents H, halogen, alkyl or alkoxy having 1 to 3 carbon atoms.
In some embodiments of the invention, the compound of formula I comprises 0.01 to 15 wt% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula I accounts for 0.01-10% of the total weight of the liquid crystal composition.
In some embodiments of the present invention, the compound of formula II comprises 0.001 to 5 wt% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula II accounts for 0.01-1% of the total weight of the liquid crystal composition.
Preferably, the compound of formula i is selected from the group consisting of:
Figure BDA0001421806380000034
wherein R is11Represents an alkyl OR alkoxy group having 1 to 10 carbon atoms, an alkenyl OR alkenyloxy group having 2 to 10 carbon atoms, -OR5OR6
R51Represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms, R61Represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
Still further, the compound of I-1 is selected from the group consisting of:
Figure BDA0001421806380000035
Figure BDA0001421806380000036
wherein, if R11represents-OR51OR61Then R is51Is not- (CH)2)2-;
Figure BDA0001421806380000041
Wherein, if R11represents-OR51OR61Then R is51Is not- (CH)2)2-or- (CH)2)3-;
Figure BDA0001421806380000042
Wherein, if R11represents-OR51OR61Then R is51Is not- (CH)2)2-、-(CH2)3-or- (CH)2)4-;
Figure BDA0001421806380000043
Wherein, if R11represents-OR51OR61Then R is51Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-or- (CH)2)5-;
Figure BDA0001421806380000044
Wherein, if R11represents-OR51OR61Then R is51Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-or- (CH)2)6-;
And
Figure BDA0001421806380000045
wherein, if R11represents-OR51OR61Then R is51Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-、-(CH2)6-or- (CH)2)8-。
Preferably, in the general formula II, P is1And P2Each independently represent
Figure BDA0001421806380000046
Or
Figure BDA0001421806380000047
Still further preferably, the compound of formula ii is selected from the group consisting of:
Figure BDA0001421806380000048
Figure BDA0001421806380000051
Figure BDA0001421806380000061
Figure BDA0001421806380000071
Figure BDA0001421806380000081
Figure BDA0001421806380000091
Figure BDA0001421806380000101
Figure BDA0001421806380000111
Figure BDA0001421806380000121
Figure BDA0001421806380000131
further, the liquid crystal composition further comprises at least one compound of formula III and/or at least one compound of formula IV:
Figure BDA0001421806380000132
wherein the content of the first and second substances,
R3and R4Each independently represents-H, -F, alkyl OR alkoxy containing 1-12 carbon atoms, alkenyl OR alkenyloxy containing 2-12 carbon atoms, -OR5OR6
Figure BDA0001421806380000133
Or
Figure BDA0001421806380000134
Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
Z2represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-;
L5And L6Each independently represents-F, -Cl, -CN or-NCS;
R7and R8Each independently represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, an alkenyl or alkenyloxy group having 2 to 12 carbon atoms;
ring (C)
Figure BDA0001421806380000135
To represent
Figure BDA0001421806380000136
Or
Figure BDA0001421806380000137
Wherein the content of the first and second substances,
Figure BDA0001421806380000138
in one or more-CH2-can be replaced by-O-,
Figure BDA0001421806380000139
wherein at most one-H may be substituted by-F;
ring (C)
Figure BDA00014218063800001310
And ring
Figure BDA00014218063800001311
Each independently represent
Figure BDA00014218063800001312
Or
Figure BDA00014218063800001313
n represents 0, 1 or 2, and when n is 2, a ring
Figure BDA00014218063800001314
May be the same or different, Z2May be the same or different;
m represents 1, 2 or 3, and when m is 2 or 3, a ring
Figure BDA0001421806380000141
May be the same or different.
Further preferably, the compound of formula iii is selected from the group consisting of:
Figure BDA0001421806380000142
wherein the content of the first and second substances,
R31and R41Each independently represents-H, -F, alkyl OR alkoxy containing 1-7 carbon atoms, alkenyl OR alkenyloxy containing 2-7 carbon atoms, -OR5OR6
Figure BDA0001421806380000143
Or
Figure BDA0001421806380000144
Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F.
In some embodiments of the invention, the compound of formula III is 20 to 60 wt% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula III accounts for 35-60% of the total weight of the liquid crystal composition.
Further preferably, the compound of formula iv is selected from the group consisting of:
Figure BDA0001421806380000145
Figure BDA0001421806380000151
wherein the content of the first and second substances,
R71and R81Each independently represents H,Alkyl or alkoxy having 1 to 7 carbon atoms, alkenyl or alkenyloxy having 2 to 7 carbon atoms.
In some embodiments of the present invention, the compound of formula IV comprises 20 to 70 wt% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula IV accounts for 40-65 wt% of the total weight of the liquid crystal composition.
In some embodiments of the invention, the compound of formula I is preferably selected from the group consisting of: i-3-2, I-3-3 and I-3-4.
In some embodiments of the invention, the compound of formula II is preferably selected from the group consisting of: II-24, II-64, II-20 and II-148.
In some embodiments of the invention, the compound of formula III is preferably selected from the group consisting of: III-2, III-9, III-6, III-3, III-7 and III-4.
In some embodiments of the invention, the compound of formula III is preferably selected from the group consisting of: IV-2, IV-6, IV-1, IV-3, IV-5, IV-9 and IV-10.
In another aspect, the present invention provides a liquid crystal composition further comprising one or more additives known to those skilled in the art and described in the literature. For example, pleochroic dyes and/or chiral dopants may be added in an amount of 0 to 15 wt% based on the total weight of the liquid crystal composition.
The following shows possible dopants which are preferably added to the composition according to the invention.
Figure BDA0001421806380000161
Figure BDA0001421806380000171
In some embodiments of the present invention, preferably, the dopant comprises 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the dopant constitutes 0-1 wt% of the total weight of the liquid crystal composition.
The stabilizers which may be added to the compositions according to the invention are mentioned below, for example.
Figure BDA0001421806380000172
Figure BDA0001421806380000181
Figure BDA0001421806380000191
Preferably, the stabilizer is selected from the group consisting of the stabilizers shown below.
Figure BDA0001421806380000192
In some embodiments of the present invention, preferably, the stabilizer comprises 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the stabilizer is 0-1 wt% of the total weight of the liquid crystal composition; as a particularly preferred embodiment, the stabilizer is 0 to 0.1 wt% of the total weight of the liquid crystal composition.
In another aspect, the present invention also provides a liquid crystal display device comprising the above liquid crystal composition.
Has the advantages that:
the liquid crystal composition provided by the invention has suitable optical anisotropy and dielectric anisotropy, maintains a relatively high clearing point, and has higher maximum penetration rate and higher contrast. When the liquid crystal composition is applied to a PSVA type liquid crystal display, the liquid crystal composition has an excellent display effect.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that 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 or scope of the present invention may be made without departing from the spirit or scope of the present invention.
For convenience of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Figure BDA0001421806380000201
Compounds of the following formula are exemplified:
Figure BDA0001421806380000202
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCCGF, wherein n in the code represents the number of C atoms of the left alkyl group, for example, n is 3, namely, the alkyl group is-C3H7(ii) a C in the code represents cyclohexane, G represents 2-fluoro-1, 4-phenylene and F represents fluorine.
The abbreviated codes of the test items in the following examples are as follows:
Figure BDA0001421806380000211
wherein the content of the first and second substances,
the optical anisotropy is obtained by testing an Abbe refractometer under a sodium lamp (589nm) light source at 25 ℃;
Δε=εwherein, epsilonIs a dielectric constant parallel to the molecular axis,. epsilonFor the dielectric constant perpendicular to the molecular axis, test conditions: the temperature is 25 ℃, the temperature is 1KHz, the test box is TN90 type, and the box thickness is 7 μm;
Tmaxand (3) testing: the penetration rate of the dimming device is tested by using the DMS 505 under the voltage of 0-5V (step is 0.1V), the maximum value is selected and recorded, and the thickness of the box of the dimming device is 5.2 mu m.
The UV process conditions in the following examples: 16V drive, 80mw cm-2And 365nm irradiation for 150s, the test cell being of the VA type, the cell thickness being 3 μm.
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Comparative example 1
The liquid crystal composition of comparative example 1, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared by using the respective compounds and weight percentages listed in tables 2 and 3.
TABLE 2 liquid crystal composition formula
Figure BDA0001421806380000212
Figure BDA0001421806380000221
To 100 parts by weight of the above liquid crystal composition, polymerizable components in table 3 were added:
TABLE 3 polymerizable Components
Figure BDA0001421806380000222
The results of the performance parameter tests of the resulting composition are given in table 4 below:
table 4 performance parameter testing
Δn 0.094
Δε -3.1
Cp 73.7
Tmax(%) 27.2
Example 1
The liquid crystal composition of example 1 was prepared by replacing 3CWO4 in comparative example 1 with 3OWWO3O1, and filled between two substrates of a liquid crystal display for performance test as shown in table 5.
TABLE 5 liquid Crystal composition formulations
Component code Weight percent (wt.%) of
3CWO4O1 6
5CWO2 8
2CPWO2 7
3CPWO4 9
3OWWO3O1 7
3CCWO2 14
4CCWO2 5
3CPO2 9
3CPP2 6
3CC2 20
4CC3 9
Total of 100
The contents and components of the polymerizable components were the same as in comparative example 1.
The results of the performance parameter tests of the resulting composition are given in table 6 below:
TABLE 6 Performance parameter testing
Δn 0.097
Δε -3.3
Cp 74.7
Tmax(%) 28.4
As can be seen from the comparison of comparative example 1 and example 1, the maximum penetration rate is significantly increased after the components of the general formula I of the present invention are introduced.
Comparative example 2
The liquid crystal composition of comparative example 2, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared by using the respective compounds and weight percentages listed in tables 7 and 8.
TABLE 7 liquid crystal composition formulations
Component code Weight percent (wt.%) of
3CC2 23
4CC3 3
5PP1 11
3PWO2 10
5CC3 4
3C1OWO2 4
3CCP1 3
3CPP2 15
3CPWO2 9
2CC1OWO2 7
3CC1OWO2 11
Total of 100
To 100 parts by weight of the above liquid crystal composition, polymerizable components in table 8 were added:
TABLE 8 polymerizable Components
Figure BDA0001421806380000231
Figure BDA0001421806380000241
The results of the performance parameter tests of the resulting composition are given in table 9 below:
TABLE 9 Performance parameter testing
Δn 0.109
Δε -3.2
Cp 75.6
Tmax(%) 29.1
Example 2
The liquid crystal composition of example 2, in which 3C1OWO2 in comparative example 2 was replaced with 2OWWO4O1, respectively, was filled between two substrates of a liquid crystal display for performance test, as shown in table 10.
TABLE 10 liquid crystal composition formulations
Component code Weight percent (wt.%) of
3CC2 23
4CC3 3
5PP1 11
3PWO2 10
5CC3 4
2OWWO4O1 4
3CCP1 3
3CPP2 15
3CPWO2 9
2CC1OWO2 7
3CC1OWO2 11
Total of 100
The contents and components of the polymerizable components were the same as in comparative example 2.
The results of the performance parameter tests of the resulting composition are given in table 11 below:
TABLE 11 Performance parameter testing
Figure BDA0001421806380000242
Figure BDA0001421806380000251
As can be seen from the comparison between comparative example 2 and example 2, the maximum penetration rate is significantly improved after the components of the general formula I of the present invention are introduced.
Comparative example 3
The liquid crystal composition of comparative example 3, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared by using the respective compounds and weight percentages listed in tables 12 and 13.
TABLE 12 liquid crystal composition formulations
Component code Weight percent (wt.%) of
2CPWO2 4
3CPWO2 5
3C1OWO2 7
2CC1OWO2 10
3CC1OWO2 10
4CC1OWO2 10
3CPO2 3
3CPP2 6
3CPPC3 3
3CGPC3 4
3CC2 18
4CC3 6
3CCP1 10
5PP1 4
Total of 100
To 100 parts by weight of the above liquid crystal composition were added polymerizable components in table 13:
TABLE 13 polymerizable Components
Figure BDA0001421806380000252
The results of the performance parameter tests of the resulting composition are given in table 14 below:
TABLE 14 Performance parameter testing
Δn 0.109
Δε -3.3
Cp 110
Tmax(%) 29.3
Example 3
The liquid crystal compositions of example 3 were prepared by replacing 3C1OWO2 and 3CPO2 in comparative example 3 with 2OWWO5O1 and 3OWWO4O2, respectively, and filled between two substrates of a liquid crystal display for performance testing, as shown in table 15.
TABLE 15 liquid crystal composition formulations
Component code Weight percent (wt.%) of
2CPWO2 4
3CPWO2 5
2OWWO5O1 7
2CC1OWO2 10
3CC1OWO2 10
4CC1OWO2 10
3OWWO4O2 3
3CPP2 6
3CPPC3 3
3CGPC3 4
3CC2 18
4CC3 6
3CCP1 10
5PP1 4
Total of 100
The contents and components of the polymerizable components were the same as in comparative example 3.
The results of the performance parameter tests of the resulting composition are given in table 16 below:
TABLE 16 Performance parameter testing
Δn 0.115
Δε -3.6
Cp 108.6
Tmax(%) 29.8
As can be seen from the comparison of comparative example 3 and example 3, the maximum penetration rate is significantly increased after the components of the general formula I of the present invention are introduced.
Comparative example 4
The liquid crystal composition of comparative example 4, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared by using the respective compounds and weight percentages listed in tables 17 and 18.
TABLE 17 liquid Crystal composition formulations
Component code Weight percent (wt.%) of
3CPO2 2
3CPP2 12
3C1OWO2 11
2CC1OWO2 5
3CC1OWO2 9
3CCWO2 7
3CC2 22
4CC3 4
5PP1 9
2C1OWO2 4
4C1OWO2 4
3CPP1 5
2CPP1 6
Total of 100
To 100 parts by weight of the above liquid crystal composition were added polymerizable components in table 18:
TABLE 18 polymerizable Components
Figure BDA0001421806380000271
The results of the performance parameter tests of the resulting composition are given in table 19 below:
TABLE 19 Performance parameter testing
Figure BDA0001421806380000272
Figure BDA0001421806380000281
Example 4
The liquid crystal composition of example 4, in which 3% of 3C1OWO2 in comparative example 4 was replaced with 2OWWO4O1, was filled between two substrates of a liquid crystal display device for performance test as shown in table 20.
TABLE 20 liquid Crystal composition formulations
Component code Weight percent (wt.%) of
3CPO2 2
3CPP2 12
3C1OWO2 8
2OWWO4O1 3
2CC1OWO2 5
3CC1OWO2 9
3CCWO2 7
3CC2 22
4CC3 4
5PP1 9
2C1OWO2 4
4C1OWO2 4
3CPP1 5
2CPP1 6
Total of 100
The contents and components of the polymerizable components were the same as in comparative example 4.
The results of the performance parameter tests of the resulting composition are given in table 21 below:
TABLE 21 Performance parameter testing
Δn 0.100
Δε -3.0
Cp 75.6
Tmax(%) 29.5
As can be seen from the comparison of comparative example 4 and example 4, the maximum penetration rate is significantly increased after the components of the general formula I of the present invention are introduced.
Comparative example 5
The liquid crystal composition of comparative example 5, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared by using the respective compounds and weight percentages listed in tables 22 and 23.
TABLE 22 liquid crystal composition formulations
Component code Weight percent (wt.%) of
3CC1 17
3CCV1 11
3CWO2 12
3PWO2 13
3CWO4 2
3CPP2 9
2CPWO2 9
3CCWO2 6
3CPWO2 11
3CC1OC3 3
5CPP2 3
4CC1OC3 4
Total of 100
To 100 parts by weight of the above liquid crystal composition were added polymerizable components in table 23:
TABLE 23 polymerizable Components
Figure BDA0001421806380000291
The results of the performance parameter tests of the resulting composition are given in table 24 below:
TABLE 24 Performance parameter testing
Δn 0.108
Δε -3.3
Cp 74.9
Tmax(%) 28.2
Example 5
The liquid crystal composition of example 5, in which 2% of 3CWO4 in comparative example 5 was replaced with 3OWWO4O1, was filled between two substrates of a liquid crystal display device to perform a performance test, as shown in table 25.
TABLE 25 liquid crystal composition formulations
Component code Weight percent (wt.%) of
3CC1 17
3CCV1 11
3CWO2 12
3PWO2 13
3OWWO4O1 2
3CPP2 9
2CPWO2 9
3CCWO2 6
3CPWO2 11
3CC1OC3 3
5CPP2 3
4CC1OC3 4
Total of 100
The contents and components of the polymerizable components were the same as in comparative example 5.
The results of the performance parameter tests of the resulting composition are given in table 26 below:
TABLE 26 Performance parameter testing
Δn 0.109
Δε -3.4
Cp 75.2
Tmax(%) 29.1
As can be seen from the comparison of comparative example 5 and example 5, the maximum penetration rate is significantly increased after the components of the general formula I of the present invention are introduced.
From the above examples and comparative examples, it can be seen that the liquid crystal composition of the present invention has suitable optical anisotropy, suitable dielectric anisotropy, and higher maximum transmittance and higher contrast ratio while maintaining a relatively high clearing point. When the liquid crystal composition is applied to a PSVA type liquid crystal display, the liquid crystal composition has an excellent display effect.
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the present invention is not limited thereto, and equivalent changes and modifications made according to the spirit of the present invention should be covered thereby.

Claims (4)

1. A liquid crystal composition, comprising:
at least one compound of the formula I-1
Figure FDA0003237518850000011
At least one polymerizable compound of the general formula II
Figure FDA0003237518850000012
And
at least one compound of formula iii and at least one compound of formula iv:
Figure FDA0003237518850000013
Figure FDA0003237518850000014
and is
The compound of formula iv is selected from the group consisting of:
Figure FDA0003237518850000015
Figure FDA0003237518850000016
and
Figure FDA0003237518850000017
wherein the content of the first and second substances,
R11represents an alkyl OR alkoxy group having 1 to 10 carbon atoms, an alkenyl OR alkenyloxy group having 2 to 10 carbon atoms, -OR5OR6
R51Represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms, R61Represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms;
R5represents an alkylene group having 1 to 12 carbon atoms or an alkenylene group having 2 to 12 carbon atoms, R6Represents an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms;
P1and P2Each independently represent
Figure FDA0003237518850000018
Figure FDA0003237518850000021
Figure FDA0003237518850000022
or-SH;
r1represents 1, 2 or 3;
r2and r3Each independently represents a positive integer of 0 to 6;
r4and r5Each independently represents 0, 1, 2, 3 or 4;
Z1represents a single bond, -CH2CH2-、-COO-、-OCO-、-CH2O-、-OCH2-or-CH ═ CH-COO-;
Zp1and Zp2Each independently selected from the group consisting of a single bond, -O-, -S-, -NH-, -NHCOO-, -OCONH-, -CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CF=CH-、-CH=CF-、-CF=CF-、-CO-、-COO-、-OCO-、-OCOO-、-CH2-、-OCH2-、-SCH2-、-CH2S-, -CH ═ CH-, -C ≡ C-, -CH ═ CH-COO-, and-OCO-CH ═ CH-;
Y1and Y2Each independently represents H, halogen, alkyl or alkoxy with 1-3C atoms;
R3and R4Each independently represents-H, -F, alkyl OR alkoxy containing 1-12 carbon atoms, alkenyl OR alkenyloxy containing 2-12 carbon atoms, -OR5OR6
Figure FDA0003237518850000023
Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
Z2represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-;
L5And L6Each independently represents-F, -Cl, -CN or-NCS;
R7and R8Each independently represents H, an alkyl or alkoxy group having 1 to 12 carbon atoms, an alkenyl or alkenyloxy group having 2 to 12 carbon atoms;
R71and R81Each independently represents H, an alkyl or alkoxy group having 1 to 7 carbon atoms, an alkenyl or alkenyloxy group having 2 to 7 carbon atoms;
ring (C)
Figure FDA0003237518850000024
To represent
Figure FDA0003237518850000025
Wherein the content of the first and second substances,
Figure FDA0003237518850000026
in one or more-CH2-can be replaced by-O-,
Figure FDA0003237518850000027
wherein at most one-H may be substituted by-F;
ring (C)
Figure FDA0003237518850000028
And ring
Figure FDA0003237518850000029
Each independently represent
Figure FDA00032375188500000210
Figure FDA00032375188500000211
n represents 0, 1 or 2, and when n is 2, a ring
Figure FDA00032375188500000212
May be the same or different, Z2May be the same or different;
m represents 1, 2 or 3, and when m is 2 or 3, a ring
Figure FDA00032375188500000213
Which may be the same or different from each other,
and is
The compound of the general formula I-1 accounts for 1-15 wt% of the total weight of the liquid crystal composition;
the compound of the general formula II accounts for 0.001-5 wt% of the total weight of the liquid crystal composition;
the compound of the general formula III accounts for 20-60 wt% of the total weight of the liquid crystal composition;
the compound of the general formula IV accounts for 20-70 wt% of the total weight of the liquid crystal composition.
2. The liquid crystal composition of claim 1, wherein in the formula II, P is1And P2Each independently represent
Figure FDA0003237518850000031
3. The liquid crystal composition of claim 2, wherein the compound of formula ii is selected from the group consisting of:
Figure FDA0003237518850000032
Figure FDA0003237518850000041
Figure FDA0003237518850000051
Figure FDA0003237518850000061
Figure FDA0003237518850000071
Figure FDA0003237518850000081
Figure FDA0003237518850000091
Figure FDA0003237518850000101
Figure FDA0003237518850000111
Figure FDA0003237518850000121
and
Figure FDA0003237518850000122
4. a liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 3.
CN201710894136.5A 2017-09-28 2017-09-28 Liquid crystal composition with high transmittance and liquid crystal display device thereof Active CN109575952B (en)

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