CN109581702B - Liquid crystal display device having a plurality of pixel electrodes - Google Patents
Liquid crystal display device having a plurality of pixel electrodes Download PDFInfo
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- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- 125000005453 2,5-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C(F)=C([H])C([*:2])=C1F 0.000 description 1
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- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- NRHZAVJNUJCQRL-UHFFFAOYSA-N 4-[4-(4-aminophenyl)piperazin-1-yl]aniline Chemical compound C1=CC(N)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 NRHZAVJNUJCQRL-UHFFFAOYSA-N 0.000 description 1
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 1
- QEDHNSAOECJYDI-UHFFFAOYSA-N 4-n-[2-(4-amino-n-methylanilino)ethyl]-4-n-methylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(C)CCN(C)C1=CC=C(N)C=C1 QEDHNSAOECJYDI-UHFFFAOYSA-N 0.000 description 1
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL 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
- G02F1/00—Devices 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
- G02F1/01—Devices 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
- G02F1/13—Devices 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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL 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
- G02F1/00—Devices 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
- G02F1/01—Devices 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
- G02F1/13—Devices 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
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL 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
- G02F1/00—Devices 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
- G02F1/01—Devices 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
- G02F1/13—Devices 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
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
- G02F1/133723—Polyimide, polyamide-imide
Landscapes
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Mathematical Physics (AREA)
- Liquid Crystal (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The present invention provides a liquid crystal display device, comprising: the liquid crystal display device comprises an upper substrate, a liquid crystal material layer and a lower substrate, wherein the liquid crystal material layer is composed of a liquid crystal composition, the liquid crystal composition comprises one or more compounds in a general formula I, and the liquid crystal display device comprising the liquid crystal composition has the advantages of low voltage driving, high charge retention rate, high response speed, slight afterimage and good low-temperature storage property.
Description
Technical Field
The invention relates to the field of liquid crystal display, in particular to a liquid crystal display device which has the characteristics of quick response time, low driving voltage, high charge retention rate, stable low-temperature storage and the like.
Background
In the liquid crystal display device, the operation modes based on the liquid crystal molecules are classified as follows: phase Change (PC), Twisted Nematic (TN), Super Twisted Nematic (STN), Electrically Controlled Birefringence (ECB), Optically Compensated Bend (OCB), in-plane switching (IPS), Vertical Alignment (VA), Fringe Field Switching (FFS), field-induced photo-reactive alignment (FPA), and the like. The classification of element-based driving methods is: passive Matrix (PM) and Active Matrix (AM). The PM is classified into a static (static), multiplex (multiplex), etc., and the AM is classified into a Thin Film Transistor (TFT), a Metal Insulator Metal (MIM), etc. TFTs are classified into amorphous silicon (amorphous silicon) and polycrystalline silicon (polysilicon). The latter is classified into a high temperature type and a low temperature type according to the manufacturing steps. The light source is classified into a reflection type using natural light, a transmission type using a backlight, and a semi-transmission type using both natural light and backlight.
The liquid crystal display element contains a liquid crystal composition having a nematic phase. The composition has suitable properties. By improving the characteristics of the composition, an AM element having good characteristics can be obtained. The correlation between the characteristics of the two is summarized in table 1 below. The properties of the composition are further described based on commercially available AM elements. The temperature range of the nematic phase is associated with the temperature range in which the element can be used. The upper limit temperature of the nematic phase is preferably about 70 ℃ or higher, and the lower limit temperature of the nematic phase is preferably about-10 ℃ or lower. The viscosity of the composition correlates to the response time of the element. In order to display a moving image with the device, the response time is preferably short. Ideally shorter than 1 millisecond response time. Therefore, the viscosity of the composition is preferably low. More preferably, the viscosity at low temperature is low.
TABLE 1 Properties of the compositions and AM elements
A liquid crystal display element may flicker on a display screen after a long period of use. By the presumption: the flicker phenomenon is related to the afterimage of the image, and when the image is driven by the alternating current, the flicker is generated by the potential difference between the potential of the positive frame and the potential of the negative frame. In order to reduce the generation of flicker, improvement is attempted with respect to the structure of the element or the composition of the composition.
In order to provide these liquid crystal display elements with uniform display characteristics, it is necessary to uniformly control the molecular alignment of the liquid crystal. Specifically, the liquid crystal alignment film uniformly aligns liquid crystal molecules on a substrate in one direction, and the liquid crystal molecules have a certain tilt angle (pretilt angle) from the substrate surface. The liquid crystal alignment film is one of important factors relating to the display quality of a liquid crystal display device, and the function of the liquid crystal alignment film has become important year by year as the quality of the display device is improved.
The liquid crystal alignment film is formed using a liquid crystal aligning agent. The liquid crystal aligning agent mainly used at present is a solution (varnish) obtained by dissolving polyamic acid or soluble polyimide in an organic solvent. After the solution is applied to a substrate, a film is formed by heating or the like, thereby forming a liquid crystal alignment film of polyimide. At present, a rubbing method is industrially used in which liquid crystal molecules are aligned by a liquid crystal alignment film, and a uniform alignment of liquid crystal molecules is obtained by rubbing the surface of the liquid crystal alignment film in one direction using a cloth implanted with fibers such as nylon, rayon, and polyester. However, the rubbing method has the following problems: display defects caused by chipping of the alignment Film or adhesion of fibrous impurities, etc. generated in the process, display defects caused by breakdown of Thin-Film Transistor (TFT) elements due to generation of static electricity, etc.
In order to solve this problem, a photoalignment method has been proposed in which the formed film is irradiated with light to perform alignment treatment, and numerous alignment mechanisms such as a photodecomposition method, a photoisomerization method, a photodimerization method, and a photocrosslinking method have been introduced so far. The photoalignment method has the following advantages: the uniformity of alignment is high compared with the rubbing method, and since the non-contact alignment method is used, the film is not scratched, and the problem of poor display of the liquid crystal display device due to dust, static electricity, and the like can be reduced.
In the related art, although research and development personnel have conducted a lot of researches on materials used in a liquid crystal alignment film using a photo-alignment method, the amount of impurity ions in the alignment film manufactured by the photo-alignment method is increased compared to the alignment film using a rubbing method, and thus, the voltage holding ratio is decreased.
On the other hand, the photoalignment method has a smaller anchoring energy and a lower alignment property of liquid crystal molecules than the rubbing method, and thus, the response time of the liquid crystal display device is increased or the probability of image sticking is increased.
Disclosure of Invention
The invention aims to solve the problems of long response time, high afterimage probability and low voltage holding ratio of a liquid crystal display device and the problem of how to strengthen the acting force of a liquid crystal material layer on an alignment film layer after photo-alignment. The invention provides a liquid crystal display device, which preferably adopts a liquid crystal composition containing an oxyalkyl chain as a liquid crystal material layer and is matched with a photoalignment alignment layer of the liquid crystal display device for use, so that the liquid crystal display device has the advantages of low voltage driving, high charge retention rate, high response speed, slight afterimage and good low-temperature storage property.
The technical scheme is as follows: the invention provides a liquid crystal display device with short response time, large voltage holding ratio, large contrast, good low-temperature storage stability and low driving voltage, comprising: an upper substrate, a liquid crystal material layer, a lower substrate, wherein the liquid crystal material layer is composed of a liquid crystal composition comprising one or more compounds of formula I:
wherein,
the R is1Represents H, a substituted or unsubstituted, linear or branched alkyl or alkoxy group of 1 to 12 carbon atoms, a substituted or unsubstituted, linear or branched alkenyl or alkenyloxy group of 2 to 12 carbon atoms, a cycloalkyl group containing 3 to 6 carbon atoms, CH3(CH2)pO(CH2)qO-in which one or more-CH groups in cycloalkyl of 3 to 6 carbon atoms2-may be replaced by-O-;
x represents-H, -F, -CN, -NCS, a halogenated or non-halogenated alkyl or alkoxy group with 1-5 carbon atoms, a halogenated or non-halogenated alkenyl or alkenyloxy group with 2-5 carbon atoms, CH3(CH2)pO(CH2)qO-；
P is an integer of 0-12, and q is a positive integer of 1-12;
the ring
Ring(s)
Ring (C)
Are the same or different and each independently represents
Wherein,
one or more-CH2-may be replaced by-O-,
wherein one or more-H may be substituted with-F;
said X is1、X2、X3And X4The same or different, each independently represent-H, -CH3-F, and when X is1＝X2＝X3＝X4or-H or X1、X2、X3And X4When one of them is-F, X is-F, -CF3、-OCF3、-CN、-NCS、
Or CH3(CH2)pO(CH2)qO-；
Z is1And Z2The same or different, each independently represents a single bond, -CH2O-、-OCH2-、-CH＝CH-、-CH2CH2-、-CF2O-、-OCF2-；
M and n are the same or different and each independently represents 0, 1 or 2;
Z1and Z2When both are single bonds and m and n are both 1, a ring
Ring (C)
Ring (C)
At least one is not
The liquid crystal composition comprises at least one R1And/or X is CH3(CH2)pO(CH2)qO-compounds of the general formula I。
In some embodiments of the present invention, the liquid crystal display device further includes an upper alignment film layer and a lower alignment film layer.
In some embodiments of the present invention, the alignment film in the alignment film layer is formed using photoalignment.
In some embodiments of the present invention, the liquid crystal display device may further include an upper polarizer and a lower polarizer.
In some embodiments of the present invention, the upper polarizer is positioned at an outer side of the upper substrate, and the lower polarizer is positioned at an outer side of the lower substrate.
In some embodiments of the present invention, the upper alignment film layer is located on an inward side of the upper substrate, and the lower alignment film layer is located on an inward side of the lower substrate.
In some embodiments of the present invention, one or two electrode groups may be further included between the upper substrate and the upper alignment film layer, and a plurality of active devices are connected to the electrode groups.
In some embodiments of the present invention, one or two electrode groups may be further included between the lower substrate and the lower alignment film layer, and a plurality of active devices are connected to the electrode groups.
In some embodiments of the invention, the alignment film layer has a polymeric derivative of a polyamic acid that is decomposable or ex-situ upon exposure to light.
In some embodiments of the invention, the liquid crystal material layer is located between upper and lower alignment film layers.
In some embodiments of the present invention, a filter film layer may be further included between the inward side of the upper substrate and the upper alignment film layer, and the filter film layer may further include RGB trichromatic colors.
In some embodiments of the invention, the ring
Ring (C)
Ring (C)
Are the same or different and each independently represents
In some embodiments of the invention, the polymeric derivative of polyamic acid comprises one or more of the following functional groups:
wherein,
the R is2、R3、R4、R5The same or different, each independently represents-H, halogen, alkyl of 1-6 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms or phenyl;
the R is6Independently represents-H, alkyl of 1 to 10 carbon atoms or cycloalkyl of 3 to 10 carbon atoms;
n is1Independently represent an integer of 1 to 4; n is1When is 1, Z3is-SCH2-，n1When 2, 3 or 4, Z3May be the same or different, and Z3Is a single bond, -SCH2-or-CH2S-, and Z3At least one of which is-SCH2-or-CH2S-；
Z is4Is a divalent aromatic radical.
In some embodiments of the invention, the polymeric derivative of polyamic acid is further obtained by reacting a group of the formula:
in some embodiments of the invention, the polymeric derivative of polyamic acid is further obtained by reacting one or more compounds of the group of compounds P1 to P7:
wherein,
k is an integer of 1-12;
the G is21Independently represents a single bond, -NH-, -O-, -S-, -SO2-、-CO-、-CONH-、-CON(CH3)-、-NHCO-、-C(CH3)2-、-C(CF3)2-、-(CH2)m1-、-O-(CH2)m1-O-、-N(CH3)-(CH2)n2-N(CH3) -, -COO-, -COS-or-S- (CH)2)m1-S-；
M1 is an integer of 1-12;
n2 is an integer of 1-5;
the G is22Independently represents a single bond, -O-, -S-, -CO-, -C (CH)3)2-、-C(CF3)2-, or alkyl of 1 to 10 carbon atoms, cyclohexyl or at least one H may be replaced by-F, -CH3、-OH、-CF3、-CO2H、-CONH2Or benzyl substituted phenyl.
In some embodiments of the invention, the liquid crystal composition comprises at least one R1And/or X is CH3(CH2)pO(CH2)qO-compounds of the general formula I.
In some embodiments of the invention, the compound of formula i is selected from one or more of the group consisting of compounds of the following formulae:
wherein,
said R is1Represents a substituted or unsubstituted, linear or branched alkyl or alkoxy group of 1 to 12 carbon atoms, a substituted or unsubstituted, linear or branched alkenyl or alkenyloxy group of 2 to 12 carbon atoms, CH3(CH2)pO(CH2)qO-；
Said X represents-F, -CN, -CF3、-OCF3、
Alkyl or alkoxy of 1 to 5 carbon atoms, alkenyl or alkenyloxy of 2 to 5 carbon atoms, CH3(CH2)pO(CH2)qO-。
In some embodiments of the invention, the liquid crystal composition further comprises one or more compounds of the following formulae II-1 to II-6:
wherein,
the R is7And R8The same or different, each independently represents an alkyl or alkoxy group of 1 to 12 carbon atoms, an alkenyl or alkenyloxy group of 2 to 12 carbon atoms.
In some embodiments of the invention, the compound of formula II-1 is preferably one or more of the following compounds II-1-1 to II-1-21:
in some embodiments of the invention, the compound of formula II-2 is preferably one or more of the following compounds II-2-1 to II-2-42:
in some embodiments of the invention, the compound of formula II-3 is preferably one or more of the following compounds II-3-1 through II-3-18:
in some embodiments of the invention, the compound of formula II-4 is preferably one or more of the following compounds II-4-1 to II-4-20:
in some embodiments of the invention, the compound of formula II-5 is preferably one or more of the following compounds II-5-1 through II-5-17:
in some embodiments of the present invention, the liquid crystal composition further comprises one or more compounds of the following general formulae III-1 to III-8:
wherein,
the R is9And R10The same or different, each independently represents an alkyl or alkoxy group of 1 to 12 carbon atoms, an alkenyl or alkenyloxy group of 2 to 12 carbon atoms.
In some embodiments of the invention, the formula III-1 is preferably one or more of the compounds described by formulas III-1-1 to III-1-10 below:
in some embodiments of the invention, the formula III-2 is preferably one or more of the compounds of the following formulae III-2-1 to III-2-16:
in some embodiments of the invention, the formula III-3 is preferably one or more of the following compounds of formulae III-3-1 to III-3-16:
in some embodiments of the invention, the formula III-4 is preferably one or more of the compounds of the following formulae III-4-1 to III-4-16:
in some embodiments of the invention, the formula III-5 is preferably one or more of the compounds of the following formulae III-5-1 to III-5-16:
in some embodiments of the present invention, the liquid crystal composition may further comprise one or more compounds of the following formula IV:
wherein,
the R is11Independently represent-CF3、-OCF3-F, -CN, -NCS, fluorinated or non-fluorinated alkyl or alkoxy of 1 to 12 carbon atoms, fluorinated or non-fluorinated alkenyl or alkenyloxy of 2 to 12 carbon atoms;
the R is12Independently represent a fluorinated or non-fluorinated alkyl or alkoxy group of 1 to 12 carbon atoms, -CF3、-OCF3、-F、-CN、-NCS；
Said Y is1、Y2、Y3And Y4The same or different, each independently represent-H, -CF3、-OCF3-F or-CN;
and a, b, c and d are the same or different and each independently represents an integer of 0 to 4.
In some embodiments of the present invention, the compound of formula IV is present in an amount of 0 to 5%, preferably 0.1 to 5%, and more preferably 0.1 to 2% by weight of the total liquid crystal composition.
When the compound of the general formula IV is used in a liquid crystal composition, the ultraviolet resistance stability of the liquid crystal composition can be better improved, so that a display device containing the liquid crystal composition has good weather resistance.
In some embodiments of the present invention, the liquid crystal display device comprises a liquid crystal material layer composed of a liquid crystal composition, and the liquid crystal composition may further comprise one or more of additives such as an optically active compound, an antioxidant, an ultraviolet absorber, a dye, an antifoaming agent, a polymerizable compound, a polymerization initiator, a polymerization inhibitor, and the like.
The liquid crystal display device is an AM element which comprises the liquid crystal material layer.
In some embodiments of the present invention, the liquid crystal display device is an AM element of a Polymer Stable Alignment (PSA) type including a polymerizable compound as a liquid crystal material layer.
In some embodiments of the present invention, the display mode of the liquid crystal display device of the present invention is a PC, TN, STN, ECB, OCB, IPS, VA, FFS or FPA mode.
In some embodiments of the present invention, the display mode of the liquid crystal display device of the present invention is an IPS mode or an FFS mode.
In some embodiments of the present invention, the liquid crystal display device is driven in an active matrix driving manner.
In some embodiments of the invention, the liquid crystal display device of the invention is a transmissive element comprising a layer of liquid crystal material of the invention.
In some embodiments of the present invention, the liquid crystal composition contained in the liquid crystal material layer of the present invention is used as a nematic liquid crystal composition.
In some embodiments of the present invention, an optically active compound is added to the liquid crystal composition contained in the liquid crystal material layer of the present invention to be used as an optically active composition.
Compared with the prior art, the liquid crystal display device provided by the invention comprises the liquid crystal composition with the oxygenated alkyl chain as the liquid crystal material layer, and the acting force of the liquid crystal material layer on the alignment film layer of the optical alignment is enhanced, so that the liquid crystal display device has the advantages of low-voltage driving, high charge retention rate, high response speed, slight afterimage and good low-temperature storage property.
In the present invention, the proportions are by weight and all temperatures are in degrees centigrade, unless otherwise specified.
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.
The manufacturing method of the liquid crystal display device comprises the following steps:
the upper and lower substrates including the alignment film layers were bonded in a direction parallel to the polarization direction of ultraviolet rays, and assembled into an FFS device with a pitch of 4 and violet. The main inlet of the liquid crystal composition is provided at a position where the flow direction of the liquid crystal is substantially parallel to the polarization direction of the ultraviolet rays. The liquid crystal composition was injected into the FFS element to form the liquid crystal display device of the present invention, and the performance parameters of the liquid crystal display device were measured.
For convenience of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code listed in Table 2:
TABLE 2 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
the structural formula is represented by the codes listed in table 1, and can be expressed as follows: nCGUF, wherein n in the code represents the number of carbon atoms of the left alkyl group, for example, n is "2", that is, the alkyl group is-C2H5(ii) a C in the code represents "cyclohexyl", G in the code represents "2-fluoro-1,4-phenylene ", U in the code represents" 2, 5-difluoro-1, 4-phenylene ", and F in the code represents a" fluoro substituent ".
The test items in the following examples are abbreviated as follows:
cp: clearing Point (nematic-isotropic phase transition temperature, degree C.)
Δ n: optical anisotropy (589nm, 25 ℃ C.)
Delta epsilon dielectric anisotropy (1KHz, 25 ℃ C.)
γ 1: rotational viscosity (mPas at 25 ℃ C.)
Tcn: lower limit temperature of nematic phase
Vth: threshold voltage (V, 1KHZ, 25 ℃ C.)
VOP: operating voltage
CR: contrast ratio
RT: response time
VHR: voltage holding ratio (5V6HZ 25 ℃ C.)
Wherein the optical anisotropy is measured by using an Abbe refractometer under a sodium lamp (589nm) light source at 25 ℃.
Δε＝ε‖-ε⊥Wherein, epsilon‖Is the dielectric constant, ε, parallel to the molecular axis⊥For the dielectric constant perpendicular to the molecular axis, test conditions: 25 ℃ and 1 KHz.
Gamma 1 is obtained by testing an LCM-2 type liquid crystal physical property evaluation system; the test temperature is 25 ℃, and the test voltage is 300V-400V.
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 in the liquid crystal display device of the present invention and subjected to the performance test, was prepared according to the compounds and weight percentages listed in table 3, and the test data are shown in the following table:
TABLE 3 liquid crystal composition formula and its test performance
Comparative example 2
The liquid crystal composition of comparative example 2, which was filled in the liquid crystal display device of the present invention and subjected to the performance test, was prepared according to the compounds and weight percentages listed in table 4, and the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Example 1
The liquid crystal composition of example 1, which was filled in the liquid crystal display device of the present invention and subjected to the performance test, was prepared according to the compounds and weight percentages listed in table 5, and the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Example 2
The liquid crystal composition of example 2 was prepared according to the compounds and weight percentages listed in table 6, and filled in the liquid crystal display device of the present invention for performance testing, and the test data are shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
Example 3
The liquid crystal composition of example 3, which was filled in the liquid crystal display device of the present invention and subjected to the performance test, was prepared according to the compounds and weight percentages listed in table 7, and the test data are shown in the following table:
TABLE 7 liquid crystal composition formulations and their test performance
Example 4
The liquid crystal composition of example 4 was prepared according to the compounds and weight percentages listed in table 8, and filled in the liquid crystal display device of the present invention for performance testing, and the test data are shown in the following table:
TABLE 8 liquid crystal composition formulations and their test properties
Example 5
The liquid crystal alignment film of example 5 was prepared according to the compounds and weight percentages listed in table 9, and filled in the liquid crystal display device of the present invention for performance test, and the test data are shown in table 9 below:
TABLE 9
The compounds represented by the codes in the table are specifically shown below:
< tetracarboxylic dianhydride >
A1: 1, 2, 3, 4-cyclobutanetetracarboxylic dianhydride
A2: pyromellitic dianhydride
A3: 1, 2, 3, 4-tetramethyl-1, 2, 3, 4-cyclobutanetetracarboxylic dianhydride
< diamine >
D1: n, N '-bis (4-aminophenyl) -N, N' -dimethylethylenediamine
D2: n, N' -bis (4-aminophenyl) piperazine
D3: 4, 4' -diaminodiphenylmethane
< solvent >
N-methyl-2-pyrrolidone: NMP
Butyl cellosolve (ethylene glycol monobutyl ether): BC
< additives >
Additive Ad 1: bis [4- (allylbicyclo [2.2.1] hept-5-ene-2, 3-dicarboxyimide) phenyl ] methane
Additive Ad 2: n, N, N ', N ' -tetraglycidyl-4, 4 ' -diaminodiphenylmethane
Additive Ad 3: 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane
Additive Ad 4: 3-aminopropyltriethoxysilane
< Synthesis of Polyamic acid >
[ Synthesis example 1]
3.397g of diamine (D1) and 40.0g of dehydrated NMP40 were placed in a 100mL four-necked flask equipped with a thermometer, a stirrer, a raw material charge inlet, and a nitrogen inlet, and dissolved by stirring under a dry nitrogen stream. Then, 1.232g of acid dianhydride (A1), 1.370g of acid dianhydride (A2), and 40.0g of dehydrated NMP were added thereto, and stirring was continued at room temperature for 24 hours. 14.0g of BCC was added to the reaction solution to obtain a polyamic acid solution having a polymer solid concentration of 6 wt%. This polyamic acid solution was referred to as PA 1. The weight average molecular weight of the polyamic acid contained in PA1 was 104,500.
The weight average molecular weight of the polyamic acid was determined by GPC method using a 2695 separation module-2414 differential refractometer (manufactured by Waters) and converted to polystyrene. The obtained polyamic acid was diluted with a phosphoric acid-DMF mixed solution (phosphoric acid/DMF 0.6/100: weight ratio) until the polyamic acid concentration became about 2 wt%. The column was measured using HSPgelRTMB-M (manufactured by Waters) using the mixed solution as a developing solvent under conditions that the column temperature was 50 ℃ and the flow rate was 0.40 mL/min. As the standard polystyrene, TSK standard polystyrene manufactured by Tosoh corporation of Japan was used.
[ Synthesis examples 2 to 3]
With reference to tetracarboxylic dianhydride and diamine shown in table 9, a polyamic acid solution (PA2) and a polyamic acid solution (PA3) having a polymer solid content of 6 wt% were prepared based on the procedure of synthesis example 1, and their weight-average molecular weights were measured.
The results of measuring the weight average molecular weight of the obtained polyamic acid, including the results of synthesis example 1, are summarized in table 9.
Alignment film coating method
The liquid crystal alignment agent was coated on the upper and lower glass substrates with ITO electrodes using a rotator. In addition, including comparative examples, the rotation speed of the rotator was adjusted according to the viscosity of the alignment agent so that the alignment film had the following film thickness. After the coating, the film was dried by heating at 70 ℃ for about 1 minute, and then irradiated with linearly polarized ultraviolet light through a polarizing plate from a direction perpendicular to the substrate using a rayleigh comparison color lamp ML-501C/B manufactured by ushioincLight quantity meter UIT-150 (light receiver UVD-S365) measures the quantity of light to an exposure energy of 3.0 + -0.1J/cm at a wavelength of 365nm2The exposure time is adjusted. The whole apparatus was covered with an ultraviolet-ray-blocking film, and ultraviolet irradiation was performed at room temperature in air. Then, heat treatment was performed at 230 ℃ for 15 minutes to form an alignment film having a film thickness of 100. + -.10 nm.
The polyamic acid solutions PA1, PA2, and PA3 described in synthesis examples 1, 2, and 3 were applied to upper and lower glass substrates with ITO electrodes according to the above alignment film coating method, orthogonal upper and lower polarizers were bonded, and a 4 μm spacer and a frame adhesive were used between the upper and lower substrates to control the cell thickness, thereby forming FFS mode devices having alignment films PI1, PI2, and PI 3.
Example 6
The liquid crystal compositions described in comparative example 1, comparative example 2, example 1, example 2, example 3 and example 4 were poured into the cells of PI1, PI2 and PI3 to form liquid crystal display devices, and the performance parameters of each display device were tested, as shown in table 10 below:
watch 10
| Alignment defects | VOP | CR | RT | VHR | Tcn | |
| Comparative example 1+ PI1 | Is provided with | 4.5V | 150 | 40ms | 96.1 | -30 |
| Comparative example 1+ PI2 | Is provided with | 4.5V | 139 | 41ms | 95.9 | -30 |
| Comparative example 1+ PI3 | Is provided with | 4.5V | 122 | 43ms | 96.3 | -30 |
| Comparative example 2+ PI1 | Is provided with | 4.7V | 180 | 38ms | 96.5 | -30 |
| Comparative example 2+ PI2 | Is provided with | 4.7V | 175 | 39ms | 96.6 | -30 |
| Comparative example 2+ PI3 | Is provided with | 4.7V | 163 | 40ms | 96.7 | -30 |
| Example 1+ PI1 | Is free of | 4V | 230 | 41 | 97.1 | -30 |
| Example 1+ PI2 | Is free of | 4V | 221 | 39 | 97.3 | -30 |
| Example 1+ PI3 | Is free of | 4V | 235 | 40 | 97.5 | -30 |
| Example 2+ PI1 | Is free of | 7.5V | 350 | 13 | 97.8 | -30 |
| Example 2+ PI2 | Is composed of | 7.5V | 378 | 11 | 97.4 | -30 |
| Example 2+ PI3 | Is free of | 7.5V | 385 | 14 | 97.5 | -30 |
| Example 3+ PI1 | Is free of | 4V | 265 | 35 | 96.9 | -40 |
| Example 3+ PI2 | Is free of | 4V | 263 | 36 | 97 | -40 |
| Example 3+ PI3 | Is free of | 4V | 275 | 33 | 96.8 | -40 |
| Example 4+ PI1 | Is free of | 5.5v | 300 | 25 | 97.2 | -30 |
| Example 4+ PI2 | Is free of | 5.5v | 325 | 24 | 97.3 | -30 |
| Example 4+ PI3 | Is free of | 5.5v | 337 | 28 | 97 | -30 |
As can be seen from comparative examples 1 and 2 and examples 1 to 6, the liquid crystal display device of the invention, which uses the liquid crystal composition containing the oxygen-containing alkyl chain as the liquid crystal material layer and is matched with the photo-alignment film layer, has the advantages of low voltage driving, high charge retention rate, high response speed, good low-temperature storage property, no alignment defect, high contrast ratio, good voltage retention rate and more excellent ghost shadow performance.
Claims (7)
1. A liquid crystal display device, comprising: an upper substrate, a liquid crystal material layer, a lower substrate, wherein the liquid crystal material layer is composed of a liquid crystal composition comprising one or more compounds of formula I:
wherein,
the R is1Represents H, a substituted or unsubstituted, linear or branched alkyl or alkoxy group of 1 to 12 carbon atoms, a substituted or unsubstituted, linear or branched alkenyl or alkenyloxy group of 2 to 12 carbon atoms, a cycloalkyl group containing 3 to 6 carbon atoms, CH3(CH2)pO(CH2)qO-in which one or more-CH groups in cycloalkyl of 3 to 6 carbon atoms2-may be replaced by-O-;
x represents-H, -F, a halogenated or non-halogenated alkyl or alkoxy group of 1 to 5 carbon atoms, a halogenated or non-halogenated alkenyl or alkenyloxy group of 2 to 5 carbon atoms;
p is an integer of 0-12, and q is a positive integer of 1-12;
the ring
Ring (C)
Or rings
Are the same or different and each independently represents
Wherein,
one or more-CH2-may be replaced by-O-,
wherein one or more-H may be substituted with-F;
said X1、X2、X3And X4The same or different, each independently represent-H, -CH3-F, and when X is1＝X2＝X3＝X4or-H or X1、X2、X3And X4When one of them is-F, X is-F, -CF3、-OCF3；
Z is1And Z2The same or different, each independently represents a single bond, -CH2O-、-OCH2-、-CH＝CH-、-CH2CH2-、-CF2O-、-OCF2-；
M and n are the same or different and each independently represents 0, 1 or 2;
Z1and Z2When both are single bonds and m and n are both 1, a ring
Ring(s)
Or rings
At least one of which is not
The liquid crystal composition comprises at least one R1Is CH3(CH2)pO(CH2)qO-a compound of the general formula I;
the liquid crystal display device also comprises an alignment film layer; and is
The alignment film layer is provided with a polymerization derivative of polyamic acid which can be decomposed or ectopic when exposed to light;
the polymeric derivative of the polyamic acid is obtained by reacting groups of the following general formula:
the polymeric derivative of polyamic acid is also obtained by reacting a compound of P5:
wherein, G is21represents-NH-, -SO2-、-CONH-、-CON(CH3)-、-NHCO-、-(CH2)m1-、-N(CH3)-(CH2)n2-N(CH3) -, -COO-, -COS-or-S- (CH)2)m1-S-; m1 is 1; the n2 is an integer of 1-5.
2. A liquid crystal display device as claimed in claim 1, characterized in that the compound of the formula i is selected from the group consisting of one or more of the following formulae:
wherein,
the R is1Represents a substituted or unsubstituted, linear or branched alkyl or alkoxy group of 1 to 12 carbon atoms, a substituted or unsubstituted, linear or branched alkenyl or alkenyloxy group of 2 to 12 carbon atoms, CH3(CH2)pO(CH2)qO-；
X represents-F, -CF3、-OCF3、
Alkyl or alkoxy of 1 to 5 carbon atoms, alkenyl or alkenyloxy of 2 to 5 carbon atoms;
p is an integer of 0-12, and q is a positive integer of 1-12.
3. The liquid crystal display device of claim 1, wherein the liquid crystal composition further comprises one or more compounds of the following formulae ii-1 to ii-6:
wherein,
the R is7And R8The same or different, each independently represents an alkyl or alkoxy group of 1 to 12 carbon atoms, an alkenyl or alkenyloxy group of 2 to 12 carbon atoms.
4. The liquid crystal display device of claim 1, wherein the liquid crystal composition further comprises one or more compounds of the following general formulae iii-1 to iii-8:
wherein,
the R is9And R10The same or different, each independently represents an alkyl or alkoxy group of 1 to 12 carbon atoms, an alkenyl or alkenyloxy group of 2 to 12 carbon atoms.
5. The liquid crystal display device of claim 1, wherein the liquid crystal composition further comprises one or more compounds of formula iv:
wherein,
the R is11Independently represent-CF3、-OCF3-F, -CN, -NCS, fluorinated or non-fluorinated alkyl or alkoxy of 1 to 12 carbon atoms, fluorinated or non-fluorinated alkenyl or alkenyloxy of 2 to 12 carbon atoms;
the R is12Independently represent a fluorinated or non-fluorinated alkyl or alkoxy group of 1 to 12 carbon atoms, -CF3、-OCF3、-F、-CN、-NCS；
Said Y1、Y2、Y3And Y4The same or different, each independently represent-H, -CF3、-OCF3-F or-CN;
and a, b, c and d are the same or different and each independently represents an integer of 0 to 4.
6. A liquid crystal display device according to any of claims 1-5, characterized in that it comprises a layer of liquid crystal material consisting of a liquid crystal composition, which may further comprise one or more of additives such as optically active compounds, antioxidants, UV absorbers, dyes, defoamers, polymerizable compounds, polymerization initiators, polymerization inhibitors, etc.
7. The liquid crystal display device according to claim 6, wherein a display mode of the liquid crystal display device is a PC, TN, STN, ECB, OCB, IPS, VA, FFS, or FPA mode.
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