CN110373211B - Liquid crystal composition containing cyclopentanothiophene liquid crystal molecules - Google Patents

Liquid crystal composition containing cyclopentanothiophene liquid crystal molecules Download PDF

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CN110373211B
CN110373211B CN201910724326.1A CN201910724326A CN110373211B CN 110373211 B CN110373211 B CN 110373211B CN 201910724326 A CN201910724326 A CN 201910724326A CN 110373211 B CN110373211 B CN 110373211B
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liquid crystal
group
crystal composition
atom
cyclopentanothiophene
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万丹阳
李建
安忠维
杨晓哲
莫玲超
车昭毅
李娟利
胡明刚
杨志
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Xian Modern Chemistry Research Institute
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked

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Abstract

Hair brushDisclosed is a liquid crystal composition containing cyclopentanothiophene liquid crystal molecules, which is characterized by comprising one or more compounds with a structural general formula (1):
Figure DDA0002158384860000011
wherein R is1Is a linear alkyl group or alkenyl group having 1 to 9 carbon atoms; n and m are 0 and 1 respectively; a. the1、A2、A3Is a hydrogen atom or a fluorine atom; ring B is a benzene ring or trans-cyclohexane; r2Is F atom (F), chlorine atom (Cl), cyano group (CN), isothiocyanato group (NCS), trifluoromethoxy group (OCF)3) Trifluoromethyl (CF)3) And a C1-C9 linear alkyl group. The liquid crystal composition has the characteristics of good low-temperature compatibility, wide liquid crystal phase region, high birefringence and the like, is suitable for liquid crystal display devices in various display modes, and is particularly suitable for liquid crystal displays in TN (twisted nematic), STN (twisted nematic), FFS (fringe field switching) modes and the like. In addition, the liquid crystal composition of the present invention can also be applied to other optical devices using high birefringence liquid crystal materials.

Description

Liquid crystal composition containing cyclopentanothiophene liquid crystal molecules
Technical Field
The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal composition containing cyclopentanothiophene liquid crystal molecules, which is mainly used in the fields of liquid crystal display and non-display liquid crystal materials.
Background
The liquid crystal display has the advantages of lightness, thinness, portability, bright color, low price, low power consumption and the like, and is widely applied to various industries at present, so that the working and living modes of people are changed. Currently, liquid crystal display has become one of the mainstay industries in the field of electronic information in China, and is receiving high attention from the nation and continuously supported by a large amount of funds. The liquid crystal material is the most important component of the liquid crystal display, because the liquid crystal display utilizes the special photoelectric properties of the liquid crystal material to realize the display function. Currently, liquid crystal displays based on various display modes such as a Twisted Nematic (TN) mode, a High Twisted Nematic (HTN) mode, a Super Twisted Nematic (STN) mode, a Thin Film Transistor (TFT) mode, a Polymer Dispersed Liquid Crystal (PDLC) mode, etc. have been developed and used. Among them, a liquid crystal display (TFT-LCD) based on a thin film transistor has advantages of a fast response speed, high image quality, etc. because it can effectively control each pixel point, and is most widely used.
With the continuous development of liquid crystal display modes, liquid crystal materials, which are the most core part of liquid crystal displays, are also being developed. Liquid crystals of Schiff bases, liquid crystals of cyanobiphenyls, liquid crystals of cyanophenylcyclohexanes, fluorine-containing liquid crystal materials which can be used for liquid crystal displays of thin film transistors (TFT-LCDs), and the like have been successively developed. However, more new requirements are put forward to liquid crystal materials in new times: (1) a low driving voltage; (2) the response speed is high; (3) a wide temperature use range; 4) high stability. The requirements for the material properties are that the material has high dielectric anisotropy (delta epsilon), low rotational viscosity (gamma), wide nematic phase temperature range and high optical, electrochemical and chemical stability, and is not easy to react under the action of ultraviolet rays, strong light or various chemical substances. However, the use of a single liquid crystal compound cannot satisfy all the above requirements, and several or more liquid crystal compounds must be mixed to form a mixed liquid crystal to achieve the purpose of making up for the deficiencies of different liquid crystal materials, so as to satisfy the practical requirements of the liquid crystal display.
At present, the market of the traditional indoor liquid crystal display fields such as liquid crystal computer displays, liquid crystal televisions and the like is saturated. As a new application field of liquid crystal materials, outdoor applications such as smart phones, smart glass, vehicle-mounted display screens and the like all need a large amount of high-performance mixed liquid crystal, and the mixed crystal of the existing indoor equipment is difficult to meet the requirements at present. Therefore, the novel mixed liquid crystal material is developed, the performance index of the mixed liquid crystal material is continuously improved, and the mixed liquid crystal material has very important practical significance when being applied to smart phones, smart glass and vehicle-mounted display screens.
Disclosure of Invention
Aiming at the requirements of the liquid crystal display technology on the liquid crystal composition, the invention aims to provide a novel liquid crystal composition which has good low-temperature compatibility, wide liquid crystal phase region, higher birefringence, low preparation cost and easy acquisition. The liquid crystal composition is mainly used in the field of outdoor liquid crystal display such as vehicle-mounted liquid crystal screens, intelligent glass, intelligent vehicle lamps and the like due to the special performance of the liquid crystal composition. In addition, the liquid crystal composition of the present invention can also be applied to other optical devices using high birefringence liquid crystal materials.
In order to realize the task, the invention adopts the following technical solution:
a liquid crystal composition comprises a first component with a structural general formula shown as (1):
Figure BDA0002158384850000021
wherein R is1Is a linear alkyl group or alkenyl group having 1 to 9 carbon atoms; n and m are 0 and 1 respectively; a. the1、A2、A3Is a hydrogen atom or a fluorine atom; ring B is a benzene ring or trans-cyclohexane; r2Is F atom (F), chlorine atom (Cl), cyano group (CN), isothiocyanato group (NCS), trifluoromethoxy group (OCF)3) Trifluoromethyl (CF)3) And a C1-C9 linear alkyl group.
The first component liquid crystal compound is a novel penta-thiophene liquid crystal material, and has the advantages of low melting point, high birefringence, larger dielectric anisotropy, lower rotational viscosity and the like; in addition, the compound has simple synthetic route, easily obtained raw materials and higher yield, thereby reducing the cost of the composition.
The liquid crystal compounds of formula (1) in the compositions of the invention are preferably selected from the following structures:
Figure BDA0002158384850000031
wherein R is1Is a linear alkyl group or alkenyl group having 1 to 9 carbon atoms; r2Is F atom (F), chlorine atom (Cl), cyano group (CN), isothiocyanato group (NCS), trifluoromethoxy group (OCF)3) Trifluoromethyl (CF)3) Straight-chain alkyl and alkenyl with 1-9 carbon atoms.
Wherein (1) -1 is further preferably selected from the following compounds:
Figure BDA0002158384850000041
wherein (1) -2 is further preferably selected from the following compounds:
Figure BDA0002158384850000051
wherein (1) -3 are further preferably selected from the following compounds:
Figure BDA0002158384850000061
wherein (1) -4 are further preferably selected from the following compounds:
Figure BDA0002158384850000071
wherein (1) -5 are further preferably selected from the following compounds:
Figure BDA0002158384850000081
wherein (1) -6 are further preferably selected from the following compounds:
Figure BDA0002158384850000091
wherein (1) -7 are further preferably selected from the following compounds:
Figure BDA0002158384850000101
wherein (1) -8 are further preferably selected from the following compounds:
Figure BDA0002158384850000111
the proportion of the first component of the present invention is 1% to 70% by weight, preferably 1% to 40% by weight, more preferably 5% to 30% by weight.
The composition of the present invention comprises at least one liquid crystal compound selected from the group consisting of liquid crystal compounds represented by the general structural formula (2) as a second component:
Figure BDA0002158384850000112
wherein R is1，R2F, Cl, wherein ring A, ring B and ring C are benzene rings or cyclohexane, the benzene rings can be substituted by 1 or more fluorine atoms, and n is 0, 1. The proportion of the second component of the invention is 0-80%, preferably 10-75%, more preferably 20-70% wt.
Wherein the preferred specific structure of formula (2) is as follows:
Figure BDA0002158384850000113
Figure BDA0002158384850000121
wherein (2) -1 is more preferably of the structure:
Figure BDA0002158384850000122
among them, (2) -2 are more preferably the following specific compounds:
Figure BDA0002158384850000131
among them, (2) -3 are more preferably the following specific compounds:
Figure BDA0002158384850000132
among them, (2) to 4 are more preferably the following specific compounds:
Figure BDA0002158384850000133
among them, (2) to 5 are more preferably the following specific compounds:
Figure BDA0002158384850000141
the liquid crystal composition comprises at least one liquid crystal compound selected from liquid crystal compounds shown in a structural general formula (3) as a third component:
Figure BDA0002158384850000142
wherein R is a straight-chain alkyl group, an alkenyl group, or an alkyl group containing an ethylenic bond, and ring A, ring B, ring C are a benzene ring or cyclohexane, wherein the benzene ring may be substituted with 1 or more fluorine atoms; x1，X2＝H，F；Y＝F，Cl，OCF3，OCF2H, straight-chain alkyl groups or alkyl groups containing an ethylenic bond, etc.; z ═ CF2O，CH2CH2COO, single bond, etc.; n is 0, 1. The proportion of the third component is 0-50%, preferably 5-45% by weight, more preferably 10-40%.
Wherein the general formula (3) is preferably of the following specific structure:
Figure BDA0002158384850000151
Figure BDA0002158384850000161
among them, 3- (1) is preferably a compound:
Figure BDA0002158384850000171
Figure BDA0002158384850000181
Figure BDA0002158384850000191
among them, 3- (2) is preferably a compound:
Figure BDA0002158384850000201
Figure BDA0002158384850000211
among them, 3- (3) is preferably a compound:
Figure BDA0002158384850000221
Figure BDA0002158384850000231
among them, 3- (4) is preferably a compound:
Figure BDA0002158384850000232
Figure BDA0002158384850000241
among them, 3- (5) are preferred compounds:
Figure BDA0002158384850000251
Figure BDA0002158384850000261
among them, 3- (6) are preferred compounds:
Figure BDA0002158384850000262
Figure BDA0002158384850000271
among them, 3- (7) is preferably a compound:
Figure BDA0002158384850000272
Figure BDA0002158384850000281
among them, 3- (8) is preferably a compound:
Figure BDA0002158384850000282
Figure BDA0002158384850000291
among them, 3- (9) is preferably a compound:
Figure BDA0002158384850000292
Figure BDA0002158384850000301
among them, 3- (10) are preferred compounds:
Figure BDA0002158384850000311
among them, 3- (11) is preferably a compound:
Figure BDA0002158384850000321
among them, 3- (12) is preferably a compound:
Figure BDA0002158384850000331
among them, 3- (13) is preferably a compound:
Figure BDA0002158384850000341
among them, 3- (14) are preferred compounds:
Figure BDA0002158384850000351
among them, 3- (15) is preferably a compound:
Figure BDA0002158384850000352
among them, 3- (16) is preferably a compound:
Figure BDA0002158384850000353
the liquid crystal composition can also comprise one or more chiral additives, and the content is 0.01-1%; preferably 0.1% to 0.5%. The chiral additive is preferably selected from the following structures:
Figure BDA0002158384850000361
the liquid crystal composition also comprises a plurality of hindered phenols as antioxidant stabilizers, and the content of the hindered phenols is 1ppm-10000 ppm; preferably from 10ppm to 1000 ppm. The antioxidant stabilizer is preferably selected from the following structures:
Figure BDA0002158384850000362
the liquid crystal composition also comprises one or more ultraviolet light stabilizers with the content of 1ppm to 10000 ppm; preferably from 10ppm to 1000 ppm. The ultraviolet light stabilizer is preferably selected from the following structures:
Figure BDA0002158384850000363
the invention may further comprise one or more liquid crystal components having a polymerizable group in an amount of 1ppm to 10000 ppm; preferably 100ppm to 1000 ppm. The polymerizable liquid crystal component is preferably selected from the following structures:
Figure BDA0002158384850000364
Figure BDA0002158384850000371
the liquid crystal composition has larger dielectric anisotropy, high birefringence, wide temperature use range and lower cost, and is suitable for TFT liquid crystal display technology, especially TN and IPS modes.
Detailed Description
The present invention will be described in further detail with reference to specific examples. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the scope of the present invention.
The preparation method of the liquid crystal formula comprises the following steps: a thermal dissolution method is used. Firstly, weighing monomer liquid crystals with different weight proportions by using a precision balance, heating to 60-100 ℃, and stirring and mixing for 1-2 hours to uniformly dissolve all components. Cooling, filtering, degassing the filtered liquid in high vacuum (less than or equal to 100Pa), and packaging with high-purity nitrogen to obtain the target mixed liquid crystal.
Unless otherwise specified, the liquid crystal compositions according to the invention are prepared according to this process.
And testing the physical property and the photoelectric property of the mixed liquid crystal. The detailed test method of the physical property and the photoelectric property comprises the following steps:
(1) clearing point (Tni):
the polarizing hot stage method: the liquid crystal sample was coated on a glass slide and placed in an orthogonal polarization microscope hot stage with a temperature rise rate of 2 ℃/min. And observing the temperature at which the liquid crystal sample turns black from a bright state in a polarizing microscope, namely the clearing point.
Or by differential scanning calorimetry: the heating rate was set at 2 ℃/min under nitrogen atmosphere.
(2) Low temperature storage temperature (LTS): about 1mL of the mixed liquid crystal was put into a transparent glass bottle and placed in a low-temperature refrigerator. The temperature is set to-20 ℃, 30 ℃ and 40 ℃, and the mixture is stored for 10 days respectively, and whether crystal precipitation or smectic phase exists is observed. If no crystal is precipitated at the temperature of minus 30 ℃, LTS is less than or equal to minus 30 ℃.
(3) Birefringence (Δ n): respectively measuring ordinary rays (n) by using Abbe refractometer at constant temperature of 25 DEG Co) And extraordinary rays(ne) Refractive index of (1), birefringence (Δ n) being equal to ne－no。
(4) Dielectric constant (Δ ∈): and (3) testing by using an LCR (liquid crystal resistance) meter at the constant temperature of 25 ℃. Δ ε ═ ε∥-ε⊥I.e. the dielectric constant (. epsilon.) in the direction of the molecular long axis∥) Dielectric constant (. epsilon.) with respect to the minor axis of the molecule⊥) The difference of (a).
(5) Spring constant (K)11，K33): under the constant temperature condition of 25 ℃, K is obtained by testing a liquid crystal capacitance-voltage (C-V) curve and fitting11And K33。
(6) Rotational viscosity (. gamma.)1): under the constant temperature condition of 25 ℃, the transient current value Ip of the liquid crystal molecules deflected along with the movement of the electric field is tested by applying voltage to the liquid crystal test box, and the rotational viscosity gamma is calculated1。
Code number and description:
(1) physical parameters
(Code) Description of the invention Unit of
Tni Clearing points ℃
TCN Low temperature storage temperature ℃
Δε Dielectric anisotropy constant -
Δn Double refractive index -
γ1 Rotational viscosity mPa·s
K11 Elasticity constant of splay pN
K33 Flexural elastic constant pN
(2) Structural abbreviations
Figure BDA0002158384850000381
For example:
Figure BDA0002158384850000382
Figure BDA0002158384850000391
example 1:
Figure BDA0002158384850000392
example 2:
Figure BDA0002158384850000393
Figure BDA0002158384850000401
example 3:
Figure BDA0002158384850000402
example 4:
Figure BDA0002158384850000411
example 5:
Figure BDA0002158384850000412
Figure BDA0002158384850000421
example 6:
Figure BDA0002158384850000422
the formula in the embodiment has larger dielectric anisotropy, high birefringence, wide temperature use range and lower rotational viscosity, and is suitable for TFT liquid crystal display technology, especially TN and IPS modes.
The liquid crystal composition provided by the invention also needs to be added with proper additives, such as an anti-ultraviolet agent, an antioxidant, a defoaming agent and the like.

Claims (2)

1. A liquid crystal composition containing cyclopentanothiophene liquid crystal molecules is characterized in that the composition contains a liquid crystal compound as a first component, wherein the liquid crystal compound is represented by a structural general formula (1), and the mass percentage of the liquid crystal compound is 1-70%:
Figure FDA0003308738020000011
wherein R is1Is a linear alkyl or alkenyl group having 1 to 9 carbon atoms; n and m are 0 and 1 respectively; a. the1、A2、A3Is a hydrogen atom or a fluorine atom; ring B is a benzene ring or trans-cyclohexane; r2Is F atom, chlorine atom, cyano, isothiocyanato, trifluoromethoxy, trifluoromethyl or C1-C9 linear alkyl.
2. A liquid crystal cell comprising the liquid crystal composition according to claim 1.
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WO2024133363A1 (en) * 2022-12-23 2024-06-27 Merck Patent Gmbh Liquid-crystal medium

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DE102015015108A1 (en) * 2014-12-17 2016-06-23 Merck Patent Gmbh Liquid crystalline medium
CN109321257A (en) * 2018-12-04 2019-02-12 西安瑞立电子材料有限公司 Contain dibenzofurans pentalane class liquid-crystal compounds
CN109762577A (en) * 2019-02-12 2019-05-17 西安近代化学研究所 A kind of liquid-crystal compounds, composition and compounds process for production thereof based on pentamethylene and benzofuran skeleton

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DE102010052810A1 (en) * 2009-12-22 2011-06-30 Merck Patent GmbH, 64293 Liquid crystalline medium

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US4853149A (en) * 1986-10-25 1989-08-01 Merck Patent Gesellschaft Mit Beschrankter Haftung Heterocyclic liquid crystal compounds
DE102015015108A1 (en) * 2014-12-17 2016-06-23 Merck Patent Gmbh Liquid crystalline medium
CN109321257A (en) * 2018-12-04 2019-02-12 西安瑞立电子材料有限公司 Contain dibenzofurans pentalane class liquid-crystal compounds
CN109762577A (en) * 2019-02-12 2019-05-17 西安近代化学研究所 A kind of liquid-crystal compounds, composition and compounds process for production thereof based on pentamethylene and benzofuran skeleton

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