CN110272747B - Liquid crystal composition containing self-aligned compound and application thereof - Google Patents

Liquid crystal composition containing self-aligned compound and application thereof Download PDF

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CN110272747B
CN110272747B CN201810215618.8A CN201810215618A CN110272747B CN 110272747 B CN110272747 B CN 110272747B CN 201810215618 A CN201810215618 A CN 201810215618A CN 110272747 B CN110272747 B CN 110272747B
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liquid crystal
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compound represented
crystal composition
compound
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CN110272747A (en
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王杰
邢文丽
陈海光
姜天孟
储士红
未欣
王新颖
田会强
苏学辉
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Beijing Bayi Space LCD Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • 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

Abstract

The invention relates to a negative dielectric anisotropy liquid crystal composition containing a self-alignment compound and application thereof. The liquid crystal composition comprises at least one of the compounds represented by the general formula I and at least one of the compounds represented by the general formula II. The liquid crystal composition contains the self-alignment compound, can be automatically aligned without an alignment film, has low rotational viscosity, can be used for a fast response liquid crystal display device of a display mode without an alignment layer, and can obviously improve the display effect of the liquid crystal display device.

Description

Liquid crystal composition containing self-aligned compound and application thereof
Technical Field
The present invention relates to a liquid crystal composition having negative dielectric anisotropy containing a self-aligning compound, and a liquid crystal display element or a liquid crystal display comprising the same.
Background
Liquid crystals are currently widely used in the field of information display, and have been used in optical communications (s.t.wu, d.k.yang.reflective Liquid Crystal display. wiley, 2001). In recent years, the application fields of liquid crystal compounds have been remarkably widened to various display devices, electro-optical devices, electronic components, sensors, and the like, and nematic liquid crystal compounds have been most widely used in flat panel displays, particularly in systems of TFT active matrix.
Liquid crystal display has experienced a long development route along with the discovery of liquid crystals. In 1888, the first liquid crystal material, cholesterol benzoate, was discovered by the austria phytologist Friedrich reintzer. In 1917, Manguin invented rubbing alignment method to make single domain liquid crystal and study optical anisotropy. The theory of scraping (Swarm) was established by e.bose in 1909 and supported by l.s.ormstein and f.zernike et al (1918), which were later discussed as statistical fluctuations by De Gennes. G.w.oseen and h.zocher created continuum theory in 1933 and was perfected by f.c.frank (1958). M.born (1916) and k.lichtennecker (1926) discovered and studied the dielectric anisotropy of liquid crystals. In 1932, w.kast accordingly classified the nematic phase into two main classes, positive and negative. In 1927, v.freedericksz and v.zolonao found that nematic liquid crystals deformed and had a voltage threshold (freedericksz transition) under the action of an electric or magnetic field. This finding provides the basis for the fabrication of liquid crystal displays.
In 1968, R.Williams, RCA corporation in America, discovered that nematic liquid crystals form fringe domains under the action of an electric field and have a light scattering phenomenon. The g.h.heilmeir was subsequently developed into a dynamic scattering display mode and made the first Liquid Crystal Display (LCD) in the world. In the early seventies, Helfrich and Schadt invented the TN principle, and people made them into display devices (TN-LCD) by using the combination of TN photoelectric effect and integrated circuit, thus developing a broad prospect for the application of liquid crystal. Since the seventies, the application of liquid crystal in display has been developed in a breakthrough due to the development of large-scale integrated circuits and liquid crystal materials, and the Super Twisted Nematic (STN) mode proposed by t.scheffer et al in 1983-1985 and the Active Matrix (AM) mode proposed by p.brody in 1972 were adopted again. Conventional TN-LCD technology has been developed into STN-LCD and TFT-LCD technology, and although the number of scan lines of STN can reach 768 lines or more, problems of response speed, viewing angle, gray scale and the like still exist when the temperature rises, so that the active matrix display mode is mostly adopted for large-area, high-information content and color display. TFT-LCD has been widely used in direct view televisions, large screen projection televisions, computer terminal displays and some military instrument displays, and TFT-LCD technology is believed to have wider application prospects. Where "active matrix" includes two types: 1. OMS (metal oxide semiconductor) or other diodes on a silicon wafer as a substrate. 2. A Thin Film Transistor (TFT) on a glass plate as a substrate. The use of single crystal silicon as a substrate material limits the display size because of the many problems that arise with the assembly of parts of the display device and even the modules at their junctions. Thus, the second type of thin film transistor is a promising type of active matrix, and the photoelectric effect utilized is typically the TN effect. TFTs include compound semiconductors, such as CdSe, or TFTs based on polycrystalline or amorphous silicon.
At present, the technology of LCD products has matured, and the technical problems of viewing angle, resolution, color saturation and the like are successfully solved, and the display performance of the LCD products is close to or exceeds that of CRT displays. Large-sized and medium-sized LCDs have gradually occupied the mainstream position of flat panel displays in their respective fields. The display modes with competitiveness are mainly in-plane switching (IPS), fringe-field switching (FFS), and Vertical Alignment (VA). When the positive liquid crystal is used in an IPS/FFS display mode, a fast response can be obtained and good reliability is obtained; while a negative liquid crystal can obtain a higher transmittance when used in an IPS/FFS display mode, the negative liquid crystal has a longer response time because of its higher viscosity. Therefore, a better liquid crystal material needs to be researched, so that the liquid crystal material not only has the advantage of fast response of positive liquid crystal, but also can effectively improve the penetration rate, and further can greatly reduce the overall power consumption of the liquid crystal display device.
The viscosity, especially the rotational viscosity γ 1, of the liquid crystal composition directly affects the response time of the liquid crystal after power-up, and specifically, the response time of the liquid crystal display depends on d2γ1/Keff(d is the thickness of the liquid crystal layer, γ 1 is the rotational viscosity of the liquid crystal, and Keff is the effective elastic constant), therefore, the purpose of improving the response time can be achieved by reducing the rotational viscosity, reducing the thickness of the liquid crystal layer, and increasing the elastic constant, and the thickness of the liquid crystal layer depends on the design of the liquid crystal display; for liquid crystal compositions, it is most effective to reduce the rotational viscosity and the liquid crystal thickness.
Disclosure of Invention
The invention provides a negative dielectric anisotropy liquid crystal composition containing a self-alignment compound, which comprises at least one compound represented by a general formula I,
Figure BDA0001598501400000021
wherein R is1Represents C1～C12Alkyl or alkoxy of (a), wherein one or more CH2The radicals may each, independently of one another, be-C.ident.C-, -CF2O-、-CH＝CH-、-O-、-CO-O-、-O-CO-、
Figure BDA0001598501400000022
Substituted by a group in which the O atoms are not directly linked to each other, wherein one or more H atoms may be replaced by halogen;
L1、L2and L3Each independently of the others represents H, F, Cl, CF3、CHF2Or has C1～C5Alkyl groups of (a);
m represents 0,1,2,3, 4, 5 or 6;
and at least one compound represented by the general formula II,
Figure BDA0001598501400000023
R2represents C1～C12Linear alkyl, linear alkoxy or C2～C12A linear alkenyl group of (a);
n represents 0 or 1;
A2represents:
Figure BDA0001598501400000024
z represents a single bond, -CH2CH2-or-CH2O-。
The compound represented by the general formula I is a self-alignment compound, and the compound can induce liquid crystal molecules to form alignment. Preferably, the compound of formula I is selected from one or more of formula I1 to formula I36:
Figure BDA0001598501400000025
Figure BDA0001598501400000031
Figure BDA0001598501400000041
wherein R is1Represents C1～C12Alkyl or alkoxy of (a), wherein one or more CH2The radicals may each, independently of one another, be replaced by-C.ident.C-, -CF2O-, -CH-, -O-, -CO-O-, -O-CO-,
Figure BDA0001598501400000042
in which one or more H atoms may be replaced by halogens, by a method in which O atoms are not directly linked to one another.
More preferably, the compounds of formula I provided by the present invention are selected from one or more of formula I1a to formula I3 a:
Figure BDA0001598501400000043
wherein Ra represents a group having C1～C7Linear alkyl radical of (1), preferably C2H5、C3H7、C4H9、C5H11、C6H13Or C7H15Further, C is preferable3H7。
Most preferably, the compounds of formula I provided by the present invention are I2 a-1:
Figure BDA0001598501400000044
in the liquid crystal composition, the self-aligning compound represented by the general formula I is preferably used in an amount of 0.01% or more, more preferably 0.1 to 10%, further preferably 0.1 to 5%, most preferably 0.1 to 4%, especially a compound selected from the group consisting of the compounds of the formulae I1 to I36.
The compound represented by the general formula II is a liquid crystal compound (the terminal group is-OCH) containing 2, 3-difluorobenzene structure2CH2F) The compounds have larger negative dielectric anisotropy and high clearing points, and can improve the negative dielectric anisotropy and the clearing points of the composition when being used in the liquid crystal composition. The end group adopts fluoroethoxyl to greatly improve dielectric anisotropy, and when the fluoroethoxyl is used in the liquid crystal composition, the dielectric anisotropy of the liquid crystal composition can be effectively improved, the use of polar monomers is reduced, the use of low-viscosity monomers is increased, the rotational viscosity of the liquid crystal composition is reduced, and the response time of a display is prolonged.
Preferably, the compound of formula II is selected from one or more of formulae IIA to IIH:
Figure BDA0001598501400000045
wherein R is2Represents C1～C7Straight chain alkyl group of (1), C2～C7Linear alkenyl groups of (a).
More preferably, the compound of formula II is selected from one or more of formula IIA1 to formula IIH 8:
Figure BDA0001598501400000051
Figure BDA0001598501400000061
most preferably, the compound of formula II is selected from one or more of formulae IIA2, IIA3, IIA5, IIB2, IIB3, IIB5, IIC2, IIC3, IIC5, IID2, IID3, IID5, IIE2, IIE3, IIE5, IIF2, IIF3, IIF5, IIG2, IIG3, IIG5, IIH2, IIH3 and IIH 5.
The liquid crystal composition provided by the invention is suitable for a display which does not contain any alignment layer, such as a Vertical Alignment (VA) type. The liquid crystal display device generally has the following structure: the liquid crystal composition is sealed between a pair of insulating substrates (e.g., glass substrates), and alignment films capable of aligning liquid crystal molecules therein in a predetermined direction are provided on both glass substrates on the side close to the liquid crystal. The liquid crystal composition provided by the invention contains the self-alignment compound, and can perform self-alignment without an alignment film.
In a preferred embodiment, the liquid-crystalline composition provided by the present invention additionally also has one or more polymerizable compounds (also referred to as Reactive Mesogens (RMs)). This type of liquid crystal composition is very suitable for use in a Vertically Aligned (VA) type display that does not contain an alignment layer. The liquid crystal molecules are aligned by induction of the self-aligning compound, and the RM may be polymerized to stabilize or adjust the alignment of the liquid crystal molecules by adjusting the UV curing conditions.
The polymerizable compound is represented by the general formula M:
RMa-AM1-(ZM1-AM2)m1-RMb M
wherein R isMaAnd RMbEach independently of the others P, P-Sp-, H, halogen, SF5、NO2Alkyl, alkenyl or alkynyl, where the radical RMaAnd RMbAt least one of (A) preferably represents a group containing POr P-Sp-; wherein P represents a polymerizable group, Sp represents a spacer group or a single bond;
AM1and AM2Each independently of the others represents an aromatic, heteroaromatic, alicyclic or heterocyclic group, preferably having 4 to 25 ring atoms, preferably C atoms, which may also contain or contain fused rings and which may optionally be mono-or polysubstituted by L;
l represents P, P-Sp-, OH, CH2OH、F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(＝O)N(RX)2、-C(＝O)Y1、-C(＝O)RX、-N(RX)2Optionally substituted silyl, optionally substituted aryl having 6 to 20C atoms, or straight or branched chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25C atoms, in which, in addition, one or more H atoms may also be replaced by F, Cl, P or P-Sp-, preferably P, P-Sp-, H, OH, CH2OH, halogen, SF5、NO2An alkyl, alkenyl or alkynyl group,
Y1represents halogen;
ZMlrepresents-O-, -S-, -CO-O-, -OCO-, -O-CO-O-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-(CH2)n1-、-CF2CH2-、-CH2CF2-、-(CF2)n1-、-CH＝CH-、-CF＝CF-、-C≡C-、-CH＝CH-、-COO-、-OCO-CH＝CH-、CR0R00Or a single bond;
R0and R00Each independently of the other represents H or an alkyl group having 1 to 12C atoms;
RXrepresents P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25C atoms, in addition to one or more non-adjacent CH2The radicals may also be interrupted by-O-, -S-, -CO-O-, -O-CO-O-with O and/or S atoms not directly linked to one anotherAnd wherein, in addition, one or more H atoms may also be replaced by F, Cl, P or P-Sp-, an optionally substituted aryl or aryloxy group having 6 to 40C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40C atoms; wherein m1 represents 0,1,2,3 or 4; n1 represents 1,2,3 or 4.
In which the radicals R presentMa、RMbAnd at least one, preferably one, two or three, particularly preferably one or two, of the substituents L represents a group P or P-Sp-or contains at least one group P or P-Sp-.
Particularly preferred compounds of the formula M are those in which:
RMaand RMbEach independently of the others P, P-Sp-, H, F, Cl, Br, I, -CN, -NO2、-NCO、-NCS、-OCN、-SCN、SF5Or straight-chain or branched alkyl having 1 to 25C atoms, in addition to which one or more non-adjacent CH groups2The radicals may also each, independently of one another, be substituted by-C (R)0)＝C(R00)-、-C≡C-、-N(R00) -, -O-, -S-, -CO-O-, -O-CO-O-in such a way that O and/or S atoms are not linked directly to one another, and in addition, one or more H atoms may also be replaced by F, Cl, Br, I, CN, P or P-Sp-, where the radical R isMaAnd RMbAt least one of (a) represents or contains a group P or P-Sp-;
AM1and AM2Each independently of the others, 1, 4-phenylene, cyclohexane-1, 4-diyl, naphthalene-2, 6-diyl, phenanthrene-2, 7-diyl, anthracene-2, 7-diyl, fluorene-2, 7-diyl, coumarin (coumarine), flavone, wherein in these groups one or more CH groups may be replaced by N, wherein one or more non-adjacent CH groups2The radicals being optionally substituted by O and/or S, 1, 4-cyclohexenylene, bicyclo [ l.1.l]Pentane-1, 3-diyl, bicyclo [2.2.2]Octane-1, 4-diyl, spiro [3.3]Heptane-2, 6-diyl, piperidine-1, 4-diyl, decahydronaphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, indane-2, 5-diyl or octahydro-4, 7-methanoindane-2, 5-diyl,wherein all these radicals may be unsubstituted or mono-or polysubstituted by L;
l represents P, P-Sp-, OH, CH2OH、F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、C(＝O)N(RX)2、-C(＝O)Y1、-C(＝O)RX、-N(RX)2Optionally substituted silyl, optionally substituted aryl having 6 to 20C atoms, or straight or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25C atoms, in which, in addition, one or more H atoms may be replaced by F, Cl, P or P-Sp-;
p represents a polymerizable group;
Y1represents halogen;
RXrepresents P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25C atoms, in addition to one or more non-adjacent CH2The radicals may be replaced by-O-, -S-, -CO-O-, -O-CO-O-in such a way that O and/or S atoms are not linked directly to one another, and in addition, one or more H atoms may also be replaced by F, Cl, P or P-Sp-, optionally substituted aryl or aryloxy groups having 6 to 40C atoms, or optionally substituted heteroaryl or heteroaryloxy groups having 2 to 40C atoms.
Very particular preference is given to those in which RMaAnd RMbRepresents P or P-Sp-of the formula M.
The compound of the general formula M provided by the invention is a polymerizable (also called as Reactive Mesogen (RM)) compound, and the structure can be polymerized under the irradiation of ultraviolet light to adjust and stabilize the alignment direction of the compound of the general formula I.
Preferably, the compound represented by the general formula M provided by the present invention is selected from one or more of the formulae M1 to M41:
Figure BDA0001598501400000081
Figure BDA0001598501400000091
Figure BDA0001598501400000101
wherein the radicals have the following meanings:
P1、P2and P3Each independently of the other represents a polymerizable group, preferably having one of the meanings stated above and below for P, particularly preferably an acrylate, methacrylate, fluorinated acrylate, oxetane, vinyl, vinyloxy or epoxy group;
Sp1、Sp2and Sp3Each independently of the others, represents a single bond or a spacer group, preferably having one of the meanings indicated above and below for Sp, and particularly preferably represents- (CH)2)p1-、-(CH2)p1-O-、-(CH2)p1-CO-O-or- (CH)2)p1-O-CO-O-；
Wherein p1 is an integer from 1 to 12, and wherein the connection to the adjacent ring in the latter-mentioned groups occurs through an O atom;
wherein, in addition, the group P1-Sp1-、P2-Sp2-and P3-Sp3One or more of (A) may represent RaaProvided that the group P present1-Sp1-、P2-Sp2-and P3-Sp3At least one of (A) does not represent Raa；
RaaRepresents H, F, Cl, CN or a linear or branched alkyl group having 1 to 25C atoms, wherein, in addition, one or more non-adjacent CH2The radicals may each, independently of one another, be substituted by-C (R)0)＝C(R00)-、-C≡C-、-N(R0) -, -O-, -S-, -CO-O-, -O-CO-O-in such a way that O and/or S atoms are not linked directly to one another, and wherein, in addition, one or more H atoms may also be replaced by F, Cl, CN or P-Sp-,particularly preferred are linear or branched, optionally mono-or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12C atoms (wherein alkenyl and alkynyl have at least two C atoms and the branched group has at least three C atoms);
R0and R00Each independently of the other and identically or differently on each occurrence represents H or alkyl having 1 to 12C atoms;
Ryand RzEach representing H, F, CH independently of each other3Or CF3；
X1、X2And X3Each independently of the others represents-CO-O-, -O-CO-or a single bond;
Z1represents-O-, -CO-, -C (R)yRz) -or-CF2CF2-；
Z2 and Z3 each independently of the other represent-CO-O-, -O-CO-, -CH2O-、-OCH2-、-CF2O-、-OCF2-or- (CH)2)n-, where n is 2,3 or 4;
l represents, identically or differently on each occurrence, F, Cl, CN or a linear or branched, optionally mono-or polyfluoro-substituted alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy group having 1 to 12C atoms, preferably F;
l 'and L' each independently of the other represent H, F or Cl;
r represents 0,1,2,3 or 4;
s represents 0,1,2 or 3;
t represents 0,1 or 2;
x represents 0 or 1.
In the compounds of formula Ml-M41,
Figure BDA0001598501400000111
preferably, it is
Figure BDA0001598501400000112
Figure BDA0001598501400000113
Wherein L, identically or differently on each occurrence, has one of the meanings given above and below, and is preferably F, Cl, CN, NO2、CH3、C2H5、C(CH3)3、CH(CH3)2、CH2CH(CH3)C2H5、OCH3、OC2H5、COCH3、COC2H5、COOCH3、COOC2H5、CF3、OCF3、OCHF2、OC2F5Or P-Sp-, very preferably F, Cl, CN, CH3,C2H5、OCH3、COCH3、OCF3Or P-Sp-, more preferably F, Cl, CH3、OCH3、COCH3Or OCF3In particular F or CH3。
Even more preferably, said compound of general formula M is selected from one or more polymerizable compounds of the following:
Figure BDA0001598501400000114
Figure BDA0001598501400000121
Figure BDA0001598501400000131
Figure BDA0001598501400000141
Figure BDA0001598501400000151
Figure BDA0001598501400000161
Figure BDA0001598501400000171
Figure BDA0001598501400000181
Figure BDA0001598501400000191
the polymerizable compound of the general formula M is provided in the present invention in an amount of 0.1 to 10%, preferably 0.1 to 5.0%, particularly preferably 0.2 to 2.0% by weight based on the total weight of the liquid crystal composition.
Preferably, the liquid crystal composition provided by the present invention further comprises one or more compounds of formula III:
Figure BDA0001598501400000192
wherein R is31、R32Each independently represents C1～C12Linear alkyl, linear alkoxy or C2～C12A linear alkenyl group of (a);
q represents 0 or 1;
A3represents:
Figure BDA0001598501400000193
A4represents:
Figure BDA0001598501400000194
Z1represents a single bond, -CH2CH2-or-CH2O-。
Preferably, the compound of formula III is selected from one or more compounds of formulae III-1 to III-14 in the following list:
Figure BDA0001598501400000195
Figure BDA0001598501400000201
wherein R is31Represents C1～C5Linear alkyl, linear alkoxy or C2～C5A linear alkenyl group of (a); r32Represents C1～C5Linear alkyl or linear alkoxy groups of (1). Further preferably, R31Represents C2H5、C3H7、C4H9、C5H11、C2H3、C3H5Or C4H7；R32Represents CH3、C2H5、C3H7、OC2H5、OC3H7Or OC4H9Preferably OC2H5。
Preferably, the liquid crystal composition provided by the present invention further comprises one or more compounds of formula IV:
Figure BDA0001598501400000202
wherein R is41、R42Each independently represents C1～C12Linear alkyl, linear alkoxy or C2～C12A linear alkenyl group of (a); a. the41、A42Each independently represents trans-1, 4-cyclohexyl or 1, 4-phenylene.
The compound of the general formula IV provided by the invention is a neutral compound with a bicyclic structure, and the structure has low rotational viscosity, so that the rotational viscosity of a liquid crystal mixture can be reduced, and the response speed is accelerated.
Preferably, the compounds represented by formula IV provided by the present invention are selected from one or more of formulae IVA and IVC:
Figure BDA0001598501400000203
wherein R is41Represents C1～C7The linear alkyl group of (1); r42Represents C1～C7Linear alkyl, linear alkoxy or C2～C7Linear alkenyl groups of (a).
Preferably, the compound of formula IV is selected from one or more of IVA1 to IVC 24:
Figure BDA0001598501400000204
Figure BDA0001598501400000211
Figure BDA0001598501400000221
more preferably, the compound of formula IV provided by the present invention is selected from one or more of formulae IVA2, IVA6, IVA14, IVA18, IVA22, IVA23, IVA28, IVB10, IVB14, IVC2, IVC4, IVC15, IVC 20.
In the liquid crystal composition, the compound represented by the general formula IV is used in an amount of 0 to 60%, preferably 9 to 50%, or 5 to 55%, or 28 to 50%, or 5 to 29%, or 20 to 55%, and more preferably 9 to 50%.
Preferably, the liquid crystal composition provided by the present invention further comprises one or more compounds of formula V:
Figure BDA0001598501400000222
wherein R is51Represents C1～C12Straight chain alkyl or C2～C12A linear alkenyl group of (a); r52Represents C1～C12Linear alkyl or linear alkoxy of (a); a. the5Represents
Figure BDA0001598501400000223
The compound of the general formula V provided by the invention is a neutral compound with a tricyclic structure, and the structure has lower rotational viscosity and higher clearing point.
Specifically, the compound represented by the general formula V provided by the invention is selected from one or more compounds in the formula VA-formula VC:
Figure BDA0001598501400000224
wherein R is51Represents C2～C7Linear alkyl or linear alkenyl of R52Represents C1～C7Linear alkyl group of (1).
Preferably, the compound of formula V is selected from one or more of VA 1-VC 30:
Figure BDA0001598501400000225
Figure BDA0001598501400000231
Figure BDA0001598501400000241
more preferably, the compound of formula V is selected from one or more of formulae VA2, VA6, VA10, VA13, VA16, VB2, VB6, VB8, VB15, VB 17.
In the liquid crystal composition, the amount of the compound represented by the general formula V is 0 to 45%, more preferably 0 to 45%, 0 to 30%, 0 to 35%, 0 to 25%, 0 to 22%, 0 to 29%, 4 to 30%, 1 to 35%, 1 to 25%, or 4 to 22%.
Preferably, the liquid crystal composition provided by the present invention further comprises one or more compounds of formula VI:
Figure BDA0001598501400000242
wherein R is61Represents C1～C12Straight chain alkyl or C2～C12A linear alkenyl group of (a); r62Representative F, C1～C12Linear alkyl, linear alkoxy or C2～C12A linear alkenyl group of (a);
L4、L5、L6each independently represents H or F, preferably L4、L5、L6Not simultaneously F.
Preferably, the compound of formula VI is selected from one or more of VIA to VID;
Figure BDA0001598501400000243
wherein R is61Represents C1～C7Straight chain alkyl or C2～C7Linear alkenyl of (3), preferably C1～C5Straight chain alkyl or C2～C5A linear alkenyl group of (a); r63Represents C1～C7Linear alkyl, linear alkoxy or C2～C7Linear alkenyl of (3), preferably C1～C5Linear alkyl, linear alkoxy or C2～C5Linear alkenyl groups of (a).
As a preferred embodiment of the present invention, the compound represented by formula VI is selected from one or more of the formulae VIA 1-VIA 4, VIB 1-VIB 24, VIC 1-VIC 14, VID 1-VID 24:
Figure BDA0001598501400000251
Figure BDA0001598501400000261
in the liquid crystal composition, except the compounds represented by the general formulas I and II, the other components (such as the compounds represented by the general formulas III, IV, V and M) are optional components, and the optional mode can be any combination mode, such as adding one, a plurality of or all of the other components into the optional components.
Specifically, the liquid crystal composition provided by the invention comprises the following compounds in percentage by weight:
(1) 0.1 to 10% of a compound represented by the general formula I;
(2) 1-90% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 0 to 90% of a compound represented by the general formula III;
(5) 0 to 90% of a compound represented by the general formula IV;
(6) 0 to 60% of a compound represented by the general formula V;
(7) 0-40% of a compound represented by the general formula VI.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 1-40% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 30-50% of a compound represented by the general formula III;
(5) 10-60% of a compound represented by the general formula IV;
(6) 0 to 30% of a compound represented by the general formula V.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 1-40% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 30-50% of a compound represented by the general formula III;
(5) 10-50% of a compound represented by the general formula IV;
(6) 0 to 30% of a compound represented by the general formula V.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 40-70% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 0 to 10% of a compound represented by the general formula III;
(5) 10-30% of a compound represented by the general formula IV;
(6) 10-20% of a compound represented by the general formula V.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 40-60% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 0 to 10% of a compound represented by the general formula III;
(5) 10-30% of a compound represented by the general formula IV;
(6) 10-20% of a compound represented by the general formula V.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 4% of a compound represented by the general formula I;
(2) 1-30% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 30-50% of a compound represented by the general formula III;
(5) 20-40% of a compound represented by the general formula IV;
(6) 0 to 20% of a compound represented by the general formula V.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 4% of a compound represented by the general formula I;
(2) 5-30% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 30-50% of a compound represented by the general formula III;
(5) 20-40% of a compound represented by the general formula IV;
(6) 0 to 20% of a compound represented by the general formula V.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 4% of a compound represented by the general formula I;
(2) 10-40% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 20-40% of a compound represented by the general formula III;
(5) 10-30% of a compound represented by the general formula IV;
(6) and 5-20% of a compound represented by the general formula VI.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 4% of a compound represented by the general formula I;
(2) 15-40% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 20-40% of a compound represented by the general formula III;
(5) 10-30% of a compound represented by the general formula IV;
(6) and 5-20% of a compound represented by the general formula VI.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 4% of a compound represented by the general formula I;
(2) 25-55% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 5-55% of a compound represented by the general formula III;
(5) 10-35% of a compound represented by the general formula V;
(6) 0 to 20% of a compound represented by the general formula VI.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 4% of a compound represented by the general formula I;
(2) 25-55% of a compound represented by the general formula II;
(3) 0.1 to 5% of a compound represented by the general formula M;
(4) 15-55% of a compound represented by the general formula III;
(5) 10-35% of a compound represented by the general formula V;
(6) 0 to 20% of a compound represented by the general formula VI.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 5-15% of a compound represented by the general formula II;
(3) 0.1 to 3% of a compound represented by the general formula M;
(4) 40-60% of a compound represented by the general formula III;
(5) 20-40% of a compound represented by the general formula IV;
(6) and 5-20% of a compound represented by the general formula VI.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 5-15% of a compound represented by the general formula II;
(3) 0.1 to 3% of a compound represented by the general formula M;
(4) 40-55% of a compound represented by the general formula III;
(5) 20-40% of a compound represented by the general formula IV;
(6) and 5-20% of a compound represented by the general formula VI.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 25-55% of a compound represented by the general formula II;
(3) 0.1 to 3% of a compound represented by the general formula M;
(4) 20-35% of a compound represented by the general formula V;
(5) and 20-35% of a compound represented by the general formula VI.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 25-45% of a compound represented by the general formula II;
(3) 0.1 to 3% of a compound represented by the general formula M;
(4) 20-35% of a compound represented by the general formula V;
(5) and 20-35% of a compound represented by the general formula VI.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 1-30% of a compound represented by the general formula II;
(3) 0.1 to 3% of a compound represented by the general formula M;
(4) 20-40% of a compound represented by the general formula III;
(5) 35-55% of a compound represented by the general formula IV;
(6) 10-25% of a compound represented by the general formula V.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 1-25% of a compound represented by the general formula II;
(3) 0.1 to 3% of a compound represented by the general formula M;
(4) 20-40% of a compound represented by the general formula III;
(5) 35-55% of a compound represented by the general formula IV;
(6) 10-25% of a compound represented by the general formula V.
Preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 15-45% of a compound represented by the general formula II;
(3) 0.1 to 3% of a compound represented by the general formula M;
(4) 0 to 30% of a compound represented by the general formula III;
(5) 30-60% of a compound represented by the general formula IV;
(6) 0-15% of a compound represented by the general formula V.
More preferably, the liquid crystal composition provided by the invention comprises the following components in percentage by mass:
(1) 0.1 to 5% of a compound represented by the general formula I;
(2) 15-45% of a compound represented by the general formula II;
(3) 0.1 to 3% of a compound represented by the general formula M;
(4) 0 to 30% of a compound represented by the general formula III;
(5) 30-50% of a compound represented by the general formula IV;
(6) 0-15% of a compound represented by the general formula V.
As a preferred embodiment of the present invention, the liquid crystal composition provided by the present invention comprises the following components by mass:
(1) 0.3% of a compound represented by the general formula I;
(2) 26 to 73.5% of a compound represented by the general formula II;
(3) 26 to 73.5% of a compound represented by the general formula III;
(4) 0.2% of a compound represented by the general formula M;
or, the liquid crystal composition comprises the following components in percentage by mass:
(1) 0.1 to 4% of a compound represented by the general formula I;
(2) 10.5 to 50% of a compound represented by the general formula II;
(3) 10.5 to 50% of a compound represented by the general formula III;
(4) 23.6 to 39% of a compound represented by the general formula IV;
(5) 0.4% of a compound represented by the general formula M;
or, the liquid crystal composition comprises the following components in percentage by mass:
(1) 0.7-2% of a compound represented by the general formula I;
(2) 7-44% of a compound represented by the general formula II;
(3) 7.7 to 47.5% of a compound represented by the general formula III;
(4) 28.7 to 42.5% of a compound represented by the general formula IV;
(5) 2-14.5% of a compound represented by the general formula V;
(6) 0.2 to 0.3% of a compound represented by the general formula M.
On the basis of the common knowledge in the field, the above-mentioned preferred conditions can be combined with each other to obtain the preferred embodiments of the present invention.
The compounds referred to in the present invention are all known compounds and are commercially available or available from the company Beijing Baybigos space-time liquid Crystal technology, Inc.
The method for producing the liquid crystal composition of the present invention is not particularly limited, and it can be produced by mixing two or more compounds by a conventional method, such as a method of mixing the different components at a high temperature and dissolving each other, wherein the liquid crystal composition is dissolved and mixed in a solvent for the compounds, and then the solvent is distilled off under reduced pressure; alternatively, the liquid crystal composition of the present invention can be prepared by a conventional method, for example, by dissolving the component having a smaller content in the main component having a larger content at a higher temperature, or by dissolving each of the components in an organic solvent, for example, acetone, chloroform or methanol, and then mixing the solutions to remove the solvent.
The liquid crystal composition contains the self-alignment compound, can be self-aligned without an alignment film, has low rotational viscosity, can be used for a fast response liquid crystal display device of a display mode without an alignment layer (such as a self-aligned vertical alignment (SAVA) type), and can obviously improve the display effect of the liquid crystal display device. Specifically, the liquid crystal display device generally has the following structure: the liquid crystal composition of the present invention is sealed between a pair of insulating substrates (e.g., glass substrates) without alignment films on the two glass substrates, and the self-alignment compound in the liquid crystal mixture can align liquid crystal molecules therein after being irradiated with a UV lamp.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Unless otherwise indicated, percentages in the present invention are weight percentages; the temperature units are centigrade; Δ n represents optical anisotropy(25℃)；||And⊥respectively represent the parallel and perpendicular dielectric constants (25 ℃, 1000 Hz); Δ represents the dielectric anisotropy (25 ℃, 1000 Hz); γ 1 represents rotational viscosity (mpa.s, 25 ℃); cp represents the clearing point (. degree. C.) of the liquid crystal composition; k11、K22、K33Respectively representing the splay, twist and bend elastic constants (pN, 25 ℃).
In the following examples, the structures of the groups in the liquid crystal compounds are represented by codes shown in the tables.
Table: radical structure code of liquid crystal compound
Figure BDA0001598501400000301
Figure BDA0001598501400000311
Take the following compound structure as an example:
Figure BDA0001598501400000312
expressed as: 3C1OWO1
Figure BDA0001598501400000313
Expressed as: 3CWO2F
Figure BDA0001598501400000314
Expressed as: 3GP1OH
In the following examples, the liquid crystal composition was prepared by a thermal dissolution method, comprising the steps of: weighing the liquid crystal compound by a balance according to the weight percentage, wherein the weighing and adding sequence has no specific requirements, generally weighing and mixing the liquid crystal compound in sequence from high melting point to low melting point, heating and stirring at 60-100 ℃ to uniformly melt all the components, filtering, performing rotary evaporation, and finally packaging to obtain the target sample.
In the following examples, the weight percentages of the components in the liquid crystal composition and the performance parameters of the liquid crystal composition are shown in the following tables.
In the following examples, all the components referred to are known liquid-crystalline compounds which can be supplied spatio-temporally from Beijing octabillion.
Example 1
Figure BDA0001598501400000315
Figure BDA0001598501400000321
Example 2
Figure BDA0001598501400000322
Example 3
Figure BDA0001598501400000323
Figure BDA0001598501400000331
Example 4
Figure BDA0001598501400000332
Example 5
Figure BDA0001598501400000333
Comparative example 1
Figure BDA0001598501400000334
Figure BDA0001598501400000341
The following table can be obtained by comparing the values of the performance parameters of the liquid crystal compositions of example 5 and comparative example 1 together:
Cp △n △ε K11 K33 γ1
example 5 76 0.098 -3.3 14.9 16.1 94
Comparative example 1 74 0.098 -3.1 14.8 16.0 106
By comparison, it can be seen that: example 5 provides a liquid crystal composition having a low rotational viscosity, i.e., a faster response time, compared to comparative example 1.
Example 6
Figure BDA0001598501400000342
Example 7
Figure BDA0001598501400000343
Figure BDA0001598501400000351
Example 8
Figure BDA0001598501400000352
Example 9
Figure BDA0001598501400000353
Figure BDA0001598501400000361
Example 10
Figure BDA0001598501400000362
Example 11
Figure BDA0001598501400000363
Example 12
Figure BDA0001598501400000364
Figure BDA0001598501400000371
Example 13
Figure BDA0001598501400000372
Comparative example 2
Figure BDA0001598501400000373
Figure BDA0001598501400000381
The liquid crystal compositions of example 13 and comparative example 2 were compared together in summary to obtain the following table:
Cp △n △ε K11 K33 γ1
example 13 78 0.097 -3.1 14.9 15.2 106
Comparative example 2 75 0.098 -3.0 13.2 13.4 112
By comparison, it can be seen that: example 13 provides a liquid crystal composition having a low rotational viscosity, i.e., having a faster response time, compared to comparative example 2.
Example 14
Figure BDA0001598501400000382
Example 15
Figure BDA0001598501400000383
Figure BDA0001598501400000391
Example 16
Figure BDA0001598501400000392
Example 17
Figure BDA0001598501400000393
Example 18
Figure BDA0001598501400000394
Figure BDA0001598501400000401
The liquid crystal composition described above was filled into a "no alignment" test cell (cell thickness d 3.5 μm, ITO electrodes on both substrates, no alignment layer). The liquid crystal composition showed spontaneous homeotropic alignment to the substrate by UV lamp (10 min, 100 mW/cm)2) After irradiation, the polymerizable compound polymerizes, stabilizing the vertical alignment. The pretilt angle, threshold voltage and response time were measured separately. The results were:
item titl(°) V10(V) T(ms)
Example 18 83.7 2.36 6.3
Comparative example 3
Figure BDA0001598501400000402
The liquid crystal composition described above was filled into a "cell with alignment" (cell thickness d ═ 3.5 μm, ITO electrodes on both substrates, and vertical alignment layers). The liquid crystal composition showed vertical alignment to the substrate, and the pretilt angle, the threshold voltage, and the response time were measured, respectively. The results were:
item titl(°) V10(V) T(ms)
Comparative example 3 89.1 2.69 12.2
A summary comparison of the pretilt angles, threshold voltages and response times of example 18 and comparative example 3 can be made as follows:
item titl(°) V10(V) T(ms)
Example 18 83.7 2.36 6.3
Comparative example 3 89.1 2.69 12.2
By comparison, it can be seen that: example 18 provides a liquid crystal composition having a faster response time than comparative example 3.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (3)

1. A negative dielectric anisotropic liquid crystal composition comprising a self-aligning compound, wherein formula one comprises the following components:
Figure FDA0002674797760000011
or the formula II comprises the following components:
Figure FDA0002674797760000012
or, the third formula consists of the following components:
Figure FDA0002674797760000013
Figure FDA0002674797760000021
the structural codes of all groups of the compounds are as follows:
Figure FDA0002674797760000022
Figure FDA0002674797760000031
wherein, RM17 is:
Figure FDA0002674797760000032
RM1 is:
Figure FDA0002674797760000033
2. use of the liquid crystal composition of claim 1 in a liquid crystal display device having no display mode of an alignment layer.
3. Use according to claim 2, wherein the display mode without alignment layer is of the self-aligned vertical alignment SAVA type.
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