CN114958390B - Negative liquid crystal compound and preparation method and application thereof - Google Patents

Negative liquid crystal compound and preparation method and application thereof Download PDF

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CN114958390B
CN114958390B CN202210680362.4A CN202210680362A CN114958390B CN 114958390 B CN114958390 B CN 114958390B CN 202210680362 A CN202210680362 A CN 202210680362A CN 114958390 B CN114958390 B CN 114958390B
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liquid crystal
group
compound
ring
independently selected
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CN114958390A (en
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谢佩
张海威
张九敏
邸庆童
何连贞
姜坤
李程辉
刘殿君
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Beijing Bayi Space LCD Technology Co Ltd
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    • 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
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
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    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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    • C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
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    • 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
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    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
    • C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems

Abstract

The invention relates to the technical field of liquid crystal materials, in particular to a negative liquid crystal compound and a preparation method and application thereof. The liquid crystal compound has a structure shown in a general formula I; the liquid crystal compound has the characteristics of larger vertical dielectric anisotropy, lower optical anisotropy, lower rotational viscosity, good liquid crystal intersolubility and the like, can be widely applied to the field of liquid crystal display, can achieve the application purposes of low power consumption, wide viewing angle and high contrast ratio, effectively improves the display quality, and has important application value.

Description

Negative liquid crystal compound and preparation method and application thereof
Technical Field
The invention relates to the technical field of liquid crystal materials, in particular to a negative liquid crystal compound and a preparation method and application thereof.
Background
In recent years, liquid crystal display devices have been developed more and more rapidly, and various types such as a vehicle-mounted small-sized liquid crystal display device, a portable liquid crystal display device, an ultra-thin liquid crystal display device, and the like have also been developed. Taking television as an example, the portable electronic device is characterized by light weight, small occupied space, convenient movement and the like, and further comprises a notebook type personal computer, a mobile phone and the like.
The liquid crystal material has great research value and good application prospect in the fields of information display materials, organic optoelectronic materials and the like as an environment material. At present, the technology of TFT-LCD products is mature, the technical problems of visual angle, resolution, color saturation, brightness and the like are successfully solved, and large-size and medium-small-size TFT-LCD displays gradually occupy the mainstream position of flat panel displays in the respective fields. However, the requirements for display technology are continuously increasing, and the liquid crystal display is required to realize faster response, lower driving voltage to reduce power consumption, etc., and the liquid crystal material is also required to have low voltage driving, fast response, wide temperature range and good low temperature stability.
The liquid crystal material plays an important role in improving the performance of a liquid crystal display, and in order to improve the performance of the material and enable the material to adapt to new requirements, the research on the synthesis and structure-performance relationship of a novel structure liquid crystal compound becomes an important work in the field of liquid crystals.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims to provide a novel structure negative liquid crystal compound, and the structure of the novel structure negative liquid crystal compound is optimized, so that the display quality can be effectively improved, and the liquid crystal material achieves the excellent performances of low power consumption, wide viewing angle and high contrast ratio, and has important application value.
Specifically, the invention provides the following technical scheme:
the invention provides a liquid crystal compound, which has a structure shown in a general formula I:
in the formula I, the compound (I),
X 1 、X 2 each independently selected from O or S;
z is selected from O, C (R) 5 R 6 ) Or Si (R) 7 R 8 )；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each is identically or differently selected from hydrogen, deuterium, fluorine, cyano, C 1 -C 40 Straight chain alkyl, C 1 -C 40 Straight-chain alkoxy, C 1 -C 40 Straight-chain heteroalkyl, C 1 -C 40 Straight-chain heteroalkoxy radicals C 3 -C 40 Branched or cyclic alkyl, C 3 -C 40 Branched or cyclic alkoxy, C 3 -C 40 Branched or cyclic heteroalkyl radicals, C 3 -C 40 Branched or cyclic heteroalkoxy, C 2 -C 40 Alkenyl or alkynyl, C 6 -C 80 Aryl and C of (2) 2 -C 60 Is selected from the group consisting of heteroaryl groups; and R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Optionally, one or more hydrogen atoms of (c) may be replaced by fluorine atoms.
Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each of which contains the following groups, identically or differently: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each of which contains the following groups, identically or differently: methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy or 2, 2-trifluoroethoxy.
Preferably, at R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 In the above, the C 1 -C 40 Straight chain heteroalkyl of (2)And C 3 -C 40 Branched or cyclic heteroalkyl radicals in (a) are intended to mean both hydrogen atoms alone or-CH 2 -groups which can be substituted by oxygen, sulphur, halogen atoms. More preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each of which contains the following groups, identically or differently: alkoxy, alkylthio, fluoroalkoxy, and fluoroalkylthio. Most preferably, said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each of which contains the following groups, identically or differently: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethoxy, 2-trifluoroethylthio, ethyleneoxy ethylene sulfur, propylene sulfur, butylene oxygen, pentene sulfur, cyclopentene oxygen, cyclopentene sulfur, hexene oxygen, hexene sulfur, cyclohexene oxygen, acetylene sulfur, propynyloxy, propynylsulfur, butynyloxy, butynylsulfur, pentynyloxy, pentynylsulfur, hexynyloxy or hexynylsulfur.
Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each of which contains the following groups, identically or differently: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl or cycloheptenyl, wherein one or more-CH 2 The groups may be replaced by the groups described above; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or cyano groups.
Preferably, the C 6 -C 80 Aryl of (2) is C 6 -C 60 Aryl groups of (a).
Preferably, the aryl group includes a simple aromatic ring, such as benzene or biphenyl, and also includes a fused aromatic ring, such as anthracene or phenanthrene.
Preferably, the C 2 -C 60 And (b) a heteroaryl group containing 2 to 60 carbon atoms and at least one heteroatom, the sum of carbon atoms and heteroatoms being at least 5.
Preferably, the heteroatom is selected from N, O or S.
Preferably, the heteroaryl group includes a simple heteroaromatic ring such as pyridine, pyrimidine or thiophene, and also includes a fused heteroaromatic ring such as quinoline or isoquinoline.
In the present invention, the hydrogen on the aryl or heteroaryl group is simply substituted or substituted to form a substituted aryl or substituted heteroaryl group, such as fluorobenzene, difluorobenzene, trifluorobenzene, tetrafluorobenzene, cyclohexylbenzene, cyclohexylfluorobenzene and the like.
Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each of which may be the same or different and comprises a group of the above groups.
Further, the R 1 、R 2 Each occurrence is independently selected from hydrogen, methyl, ethyl, cyano, trifluoromethyl, trifluoroethyl, pentafluoroethyl, methoxy, or trifluoromethoxy.
Preferably, the R 1 、R 2 Each independently selected from hydrogen, fluoro, methyl, ethyl, cyano, trifluoromethyl or trifluoromethoxy, and R 1 And R is 2 At least one of which is fluorine.
Further, the R 5 、R 6 Is hydrogen or fluorine.
Further, the R 7 、R 8 Each independently selected from methyl or ethyl.
Further, the X 1 、X 2 S.
Preferably, the liquid crystal compound is any one of the following structures:
further, the R 1 、R 2 Each occurrence is independently selected from hydrogen, methyl, ethyl, cyano, trifluoromethyl, trifluoroethyl, pentafluoroethyl, methoxy, or trifluoromethoxy.
Preferably, the liquid crystal compound is selected from the group consisting of formulas I-1, I-2, I-3, I-10, I-11, I-12, I-22, and I-24.
Preferably, the liquid crystal compound of formula I is selected from any one of the following structures:
wherein R, R' are each independently selected from the group consisting of hydrogen, fluorine, chlorine, cyano, C 1 -C 7 Alkyl, C of (2) 3 -C 6 Cycloalkyl or C of (C) 2 -C 12 Alkenyl of (2), wherein any one or more of the non-adjacent-CH 2 Optionally substituted by-c≡c-, COO-, OOC-, O-, or S-, optionally substituted by fluorine or chlorine atoms.
* -and- (x) indicates the position at which the substituents are bonded.
Preferably, the liquid crystal compound has any one of the following structures LS01-LS 222:
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wherein Z is O, si (CH) 3 ) 2 Or CF (CF) 2 。
The invention also provides a preparation method of the liquid crystal compound, wherein:
the synthetic route for Z is O is as follows:
z is Si (CH) 3 ) 2 Or CF (CF) 2 The synthetic route of (2) is as follows:
in the present invention, the starting materials for synthesizing the liquid crystal compounds of formula I can be obtained commercially.
The synthetic method of the invention has the means of principle, operation process, conventional post treatment, column purification, recrystallization purification and the like which are well known to the synthesis personnel in the field, and can completely realize the synthetic process to obtain the target product.
In the present invention, all the above reactions are carried out in a solvent selected from one or more of tetrahydrofuran, 2-methyltetrahydrofuran, N-dimethylformamide, dimethylsulfoxide, 1-methylpyrrolidin-2-one, ethanol, methanol, methylene chloride, acetone, toluene and deionized water.
The invention also provides a liquid-crystalline medium comprising one or more of the liquid-crystalline compounds described above.
Preferably, the liquid-crystalline medium further comprises, as second component, one or more compounds of the formula II:
wherein,
R 7 、R 8 each independently selected from the group consisting of groups defined by a, b, c:
a: with C 1 -C 7 Straight-chain alkyl of (C) 1 -C 7 Straight-chain alkoxy of (a);
b: one or more of the groups in a-CH 2 -a group formed after substitution by-O-, -COO-, -OOC-, or-ch=ch-;
c: one or more hydrogen atoms in any of the groups a are represented by F, cl, -ch=ch 2 or-ch=ch-CH 3 Substituted with a group formed later;
ring B, ring C, ring D, ring E are each independently selected from the group consisting of:
and at least one of the rings B, C, D, E is selected fromOne of the following;
m, n, o are each independently 0 or 1;
Z 1 、Z 2 、Z 3 each independently selected from the group consisting of single bonds, -C 2 H 4 -*、*-CH＝CH-*、*-C≡C-*、*-COO-*、*-OOC-*、*-CH 2 O-*、*-OCH 2 -*、*-CF 2 O-sum-OCF 2 A group consisting of, wherein any H may be replaced by F;
preferably, the liquid-crystalline medium further comprises one or more compounds of the formula III:
wherein,
R 9 、R 10 each independently selected from the group consisting of having C 1 -C 10 Alkyl of (C) and having C 2 -C 10 Alkenyl groups of (2), wherein any of-CH 2 Can be represented by-CH 2 O-*、*-OCH 2 - -C≡ C-instead of, any hydrogen atom may be replaced with a fluorine atom;
ring F, ring G, ring I, ring J are each independently selected from the group consisting of:
p, q, r are each independently 0 or 1;
Z 4 、Z 5 、Z 6 each independently selected from the group consisting of single bonds, -C 2 H 4 -*、*-CH＝CH-*、*-C≡C-*、*-COO-*、*-OOC-*、*-CH 2 O-*、*-OCH 2 -*、*-CF 2 O-sum-OCF 2 A group consisting of wherein any hydrogen atom may be replaced by a fluorine atom.
* -and- (x) indicates the position at which the substituents are bonded.
Preferably, in the liquid crystal medium, the mass percentage of the liquid crystal compound is 1-24%, the mass percentage of the compound with the structural formula II is 35-58%, and the mass percentage of the compound with the structural formula III is 30-46%.
Preferably, the compound of formula II is any one of the compounds of the following formulas II-1 to II-15:
wherein,
R 7 、R 8 each independently selected from the group consisting of groups defined by a, b, c:
a: with C 1 -C 7 Straight-chain alkyl of (C) 1 -C 7 Straight-chain alkoxy of (a);
b: one or more of the groups in a-CH 2 -a group formed after substitution by-O-, -COO-, -OOC-, or-ch=ch-;
c: one or more H in any of the groups in a is F, cl, -ch=ch 2 or-ch=ch-CH 3 Substituted with a group formed later;
the above-mentioned ring H 1 Ring H 2 Each of which is a single pieceIndependently selected from the group consisting of:
* -and- (x) indicates the position at which the substituents are bonded.
Preferably, the compound of formula III is any one of the following formulas III-1 to III-16:
wherein R is 9 、R 10 Each independently selected from the group consisting of having C 1 -C 10 Or have C 2 -C 10 Alkenyl groups of (2), wherein any of-CH 2 Can be represented by-CH 2 O-*、*-OCH 2 - -C≡ C-instead of, any H may be replaced by F; (F) each independently represents F or H.
Preferably, the liquid crystal medium further comprises a functional additive; the functional additive comprises one or more of an antioxidant, a chiral agent, a light stabilizer and an ultraviolet absorber.
The invention also provides a consumer product comprising a liquid crystalline medium as described above.
In the present invention, the consumer products include, but are not limited to, flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual or augmented reality displays, vehicles, video walls comprising a plurality of tiled displays, theatre or gym screens, phototherapy devices, and signs.
Unless otherwise indicated, all starting materials used in the present invention are commercially available, and any ranges recited herein include any number between the endpoints and any subrange formed by any number between the endpoints or any number between the endpoints.
Based on the technical scheme, the invention has the following beneficial effects:
the large plane conjugated rigid structure of dibenzofuran or dibenzothiophene or fluorene molecules makes the response speed and solubility of the compound worse, and limits the application of the compound. Surprisingly, the plane conjugation capability of the dithieno furan or dithieno fluorene is weakened, the solubility is improved, and the liquid crystal compound shows better intersolubility and faster response speed, so that the compound shown in the formula I can improve the intersolubility and response speed of the liquid crystal compound, improve the low-temperature stability of mixed crystals, expand the application range of liquid crystal mixtures, and have important application values.
Detailed Description
The following examples are illustrative of the invention and are not intended to limit the scope of the invention.
The specific techniques or conditions are not identified in the examples and are described in the literature in this field or are carried out in accordance with the product specifications. The reagents or equipment used were conventional products available for purchase by regular vendors without the manufacturer's attention.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the disclosure and percentages such as percentages by mass unless otherwise indicated. The novel series of liquid-crystalline compounds provided by the present invention, all of which are carried out under well-known suitable conditions, involve some simple organic preparation, for example the preparation of phenylboronic acid, which can be synthesised by a skilled operating skill and are not described in detail in the present invention.
Example 1
The preparation of compound LS11 (Z is O) comprises the following steps:
the first step: preparation of Compound Int-1
Under the protection of nitrogen, 30.0mmol of magnesium chips and 80mL of dry ethyl tertiary butyl ether are mixed, 1 particle of iodine is added, the temperature is raised, the mixture is refluxed until red color disappears, 20.0mmol of 5-propyl-4-fluoro-2-bromothiophene solution dissolved in the ethyl tertiary butyl ether is dropwise added, the reflux reaction is continued for 2 hours until the magnesium chips disappear, and 0.6mmol of NiCl is added 2 (dppp) and 36.0mmol of anhydrous lithium bromide, adding 24.0mmol of 5-amyl-4-fluoro-2-bromothiophene, heating and refluxing for reaction for 12 hours, cooling to room temperature, adding 50mL of 2N dilute hydrochloric acid aqueous solution, separating out an organic phase, drying, filtering, concentrating the filtrate under reduced pressure, separating and purifying by a silica gel column, recrystallizing by ethanol to obtain a compound Int-1, and obtaining the yield: 75%.
And a second step of: preparation of Compound Int-2
Under the protection of nitrogen, 20.0mmol of Int-1 is dissolved in 50mL of DMF, 42.0mmol of NBS is added, the reaction is stirred at room temperature for 12 hours, the reaction liquid is poured into 250mL of water, the ethyl acetate is used for extraction, the organic phase is washed with saturated brine, the organic phase is separated and dried, the filtration is carried out, the filtrate is concentrated to dryness under reduced pressure, the silica gel column is used for separation and purification, ethanol recrystallization is carried out, and the compound Int-2 is obtained, the yield is: 87%.
And a third step of: preparation of Compound Int-3
Under the protection of nitrogen, 20.0mmol of Int-2 is dissolved in 50mL of dry THF, the temperature is reduced to minus 78 ℃ by liquid nitrogen, 22.0mmol of 1.5M N-butyllithium N-hexane solution is added dropwise, stirring reaction is carried out for 1 hour, 25.0mmol of trimethyl borate is added dropwise, stirring reaction is carried out for 1 hour at room temperature, 50mL of 2N diluted hydrochloric acid aqueous solution is added, stirring reaction is carried out for 30 minutes, extraction is carried out by ethyl acetate, the organic phase is dried, filtration and filtrate is concentrated to dryness under reduced pressure, petroleum ether is added for dispersion and filtration, and a mixture of the compound Int-3 and the Int-3' is obtained, the yield is: 78%.
Fourth step: preparation of Compound Int-4
20.0mmol of the mixture of Int-3 and Int-3 'is dissolved in 60mL of dichloromethane, the temperature is reduced to 0 ℃, 10.0mL of 30% hydrogen peroxide is added, stirring reaction is carried out for 12 hours, filtration is carried out, an organic phase separated from filtrate is washed by 5% of vitamin C aqueous solution, the organic phase is dried, filtration is carried out, the filtrate is concentrated to dryness under reduced pressure, silica gel column separation and purification are carried out, and the mixture of the compounds Int-4 and Int-4' is obtained, and the yield is: 87%.
Fifth step: preparation of Compound LS11 (Z is O)
20.0mmol of the mixture of Int-4 and Int-4' is dissolved in 50mL of DMF, 40.0mmol of cesium carbonate and 2.0mmol of copper oxide are added, the temperature is raised to 120 ℃, the reaction is carried out for 12 hours under stirring, the temperature is reduced to room temperature, the filtration is carried out, the filtrate is poured into 150mL of water, the extraction is carried out with ethyl acetate, the organic phase is washed with saturated brine, the drying is carried out, the filtration is carried out, the filtrate is concentrated to dryness under reduced pressure, and the compound LS11 (Z is O) is obtained by separation and purification through a silica gel column, off-white solid is obtained in the yield: 74%, HRMS, m/z:329.0783[ M+H ]]。 1 HNMR(δ、CDCl 3 )：2.75～2.68(4H,m)；1.66～1.60(4H,m)；1.37～1.22(4H,m)；1.08(3H,t)；0.90(3H,t)。
With reference to the synthesis method similar to that of example 1 above, compounds LS01 to LS138 were prepared in which Z was O.
Example 2
Compound LS47 (Z is CF) 2 ) Comprises the following steps:
the first step: preparation of Compound Int-5
Referring to the synthetic method of example 1, only the first step of 5-propyl-4-fluoro-2-bromothiophene in example 1 was replaced with 5-ethoxy-4-fluoro-2-bromothiophene, and the 5-pentyl-4-fluoro-2-bromothiophene was replaced with 5-pentoxy-4-fluoro-2-bromothiophene to prepare compound Int-5, yield: 77%.
And a second step of: preparation of Compound Int-6
Referring to the synthetic method of example 1, only the second step of Int-1 in example 1 was replaced with Int-5 to prepare compound Int-6, yield: 90%.
And a third step of: preparation of Compound Int-7
30.0mmol of Int-6 is dissolved in 60mL of dry THF under the protection of nitrogen, liquid nitrogen is cooled to minus 78 ℃, 66.0mmol of 2.5M n-butyllithium n-hexane solution is added dropwise, stirring reaction is carried out for 1 hour, 33.0mmol of dimethylcarbamoyl chloride is added dropwise, stirring reaction is carried out for 12 hours at room temperature, 20mL of saturated ammonium chloride aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is combined and dried, filtering is carried out, the filtrate is concentrated and dried under reduced pressure, silica gel column separation and purification are carried out, ethanol recrystallization is carried out, and the compound Int-7 is obtained, the yield: 76%.
Fourth step: compound LS47 (Z is CF) 2 ) Is prepared from
Under the protection of nitrogen, 20.0mmol of Int-7 is dissolved in 40mL of dry dichloromethane, the temperature is reduced to 0 ℃, 50.0mmol of DAST is added dropwise, the mixture is stirred and reacts for 2 hours, the mixture is warmed to room temperature and stirred and reacts for 12 hours, 50mL of ice water is added dropwise, an organic phase is separated, water is extracted by dichloromethane, the organic phase is collected and washed by saturated brine, the organic phase is dried and filtered, the filtrate is concentrated to dryness under reduced pressure, and is separated and purified by a silica gel column and recrystallized by ethanol to obtain a compound LS47 as a pale yellow solid, the yield is: 92%, HRMS, m/z:381.0612[ M+H ]]。 1 HNMR(δ、CDCl 3 )：4.04～3.79(4H,m)；1.75～1.68(2H,m)；1.39～1.34(7H,m)；0.87(3H,t)。
Preparation of Compounds LS01-LS222 wherein Z is CF by analogy with the Synthesis method described in example 2 above 2 Is a compound of (a).
Example 3
Compound LS125 (Z is SiMe) 2 ) Is prepared from the following steps:
under the protection of nitrogen, 20.0mmol of Int-8 is dissolved in 60mL of dry THF, liquid nitrogen is cooled to minus 78 ℃, 44.0mmol of 2.5M n-butyllithium n-hexane solution is added dropwise, stirring reaction is carried out for 1 hour, 22.0mmol of dimethyl silicon dichloride is added dropwise, stirring reaction is carried out for 1 hour at room temperature, 20mL of saturated ammonium chloride aqueous solution is added, an organic phase is separated, the aqueous phase is extracted by ethyl acetate, the organic phase is combined and dried, filtration and filtrate decompression concentration are carried out, silica gel column separation and purification are carried out, ethanol recrystallization is carried out, and compound LS125 is obtained as a white solid, yield: 79%, HRMS, m/z:499.1906[ M+H ]]。 1 HNMR(δ、CDCl 3 )：3.94～3.91(2H,t)；3.75～3.73(2H,d)；1.92～1.78(3H,m)；1.52～1.39(7H,m)；1.32～1.13(8H,m)；1.08～0.96(2H,m)；0.90～0.85(6H,m)；0.12(6H,s)。
Preparation of Compound LS01 by analogy with the Synthesis method described in example 3 aboveZ in LS138 is SiMe 2 Is a compound of (a).
Examples of mixtures
Examples 4 to 11:
examples 4-11 show the preparation of different liquid-crystalline media, wherein the monomer structure, amount (weight percent) of the specific compounds of each example, and the results of the performance parameter test of the resulting liquid-crystalline media are shown in tables 1-8, respectively.
The temperature units involved in each example are in degrees celsius, and the specific meaning of the other symbols and the test conditions are as follows:
p. represents the clear point (. Degree. C.) of the liquid crystal, test instrument: mettler-Toledo-FP System micro thermal analyzer;
γ1 is the rotational viscosity (mpa·s) and the test conditions are: 25 ℃, INSTEC, ALCT-IR1, 18 micron vertical box;
K 11 to give a torsional spring constant, K 33 For the splay elastic constant, the test conditions were: 25 ℃, INSTEC, ALCT-IR1, 18 micron vertical box;
delta epsilon represents dielectric anisotropy, delta epsilon = epsilon-epsilon, wherein epsilon is the dielectric constant parallel to the molecular axis, epsilon is the dielectric constant perpendicular to the molecular axis, and the test conditions are: 25 ℃, INSTEC, ALCT-IR1, 18 micron vertical box;
Δn represents optical anisotropy, Δn=n o -n e Wherein n is o Refractive index of ordinary ray, n e For the refractive index of the extraordinary ray, test conditions: 589nm, 25.+ -. 0.2 ℃.
In the invention, the compounds of the general formulas I, II and III are respectively weighed according to the proportion to prepare the liquid crystal medium, wherein equipment and instruments used for preparing the liquid crystal medium are as follows:
(1) Electronic precision balance (precision 0.1 mg);
(2) Stainless steel beaker: for weighing the compound raw materials;
(3) Spoon: for adding raw materials;
(4) Magnetic force rotor: for stirring;
(5) Temperature-controlled electromagnetic stirrer.
The preparation method of the liquid crystal medium comprises the following steps:
(1) The raw materials are orderly placed;
(2) Placing a stainless steel beaker on a balance, and placing the compound of the formula I into the stainless steel beaker by using a small spoon;
(3) Sequentially adding other compound raw materials according to the required weight;
(4) Placing the stainless steel beaker with the materials on a magnetic stirring instrument for heating and melting;
(5) After most of the mixture in the stainless steel beaker is melted, adding a magnetic rotor into the stainless steel beaker, uniformly stirring the liquid crystal mixture, and cooling to room temperature to obtain the liquid crystal medium.
And filling the obtained liquid crystal medium between two substrates of the liquid crystal display for performance test.
The composition ratios and the performance parameters of the liquid crystal media of example 4 are shown in table 1;
TABLE 1
The component ratios and the performance parameters of the liquid crystal media of example 5 are shown in Table 2;
TABLE 2
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The composition ratios and the performance parameters of the liquid crystal media of example 6 are shown in Table 3;
TABLE 3 Table 3
The composition ratios and the performance parameters of the liquid crystal media of example 7 are shown in Table 4;
TABLE 4 Table 4
The component ratios and the performance parameters of the liquid crystal media of example 8 are shown in Table 5;
TABLE 5
The component ratios and the performance parameters of the liquid crystal media of example 9 are shown in Table 6;
TABLE 6
The composition ratio and the performance parameters of the liquid crystal medium of example 10 are shown in Table 7;
TABLE 7
The composition ratio of the liquid crystal medium of example 11 and its performance parameters table 8;
TABLE 8
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Comparative example 1
The formulation is shown in Table 9 below, which contains no compound of formula I, but a compound of formula V.
TABLE 9
Conclusion: as is clear from the comparison of example 9 and comparative example 1, the dibenzothiophene liquid crystal after being replaced with the dithieno furan and dithieno fluorene liquid crystal of the present invention shows good intersolubility and low temperature stability, and has a larger negative dielectric constant.
Comparative example 2
The formulation is shown in Table 10 below, and the components do not include a compound of formula I, but include a compound of formula V.
Table 10
Conclusion: as is clear from the comparison of example 10 and comparative example 2, the dithienothiophene liquid crystal was replaced with the dithienothiofuran and dithienothiofluorene liquid crystal of the present invention, which exhibited good intersolubility and low temperature stability, and had a larger negative dielectric constant.
As can be seen from the performance parameters of the liquid crystal compositions of examples 4 to 11, the liquid crystal composition provided by the invention has good intersolubility and larger negative dielectric constant, so that the intersolubility of the liquid crystal compound can be improved by using the compound shown in the formula I provided by the invention, the application range of the liquid crystal mixture is expanded, and the liquid crystal composition has important application value.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.

Claims (8)

1. A liquid crystal compound, characterized in that the liquid crystal compound is any one of the following compounds:
wherein Z is selected from O, C (R 5 R 6 ) Or Si (R) 7 R 8 )；R 5 、R 6 Is fluorine; r is R 7 、R 8 Each independently selected from methyl or ethyl;
r, R' are each independently selected from the group consisting of hydrogen, fluorine, chlorine, cyano, C 1 -C 7 Alkyl, C of (2) 3 -C 6 Cycloalkyl or C of (C) 2 -C 12 Alkenyl of (2), wherein any one or more of the non-adjacent-CH 2 Optionally substituted by-c≡c-, COO-, OOC-, O-, or S-, optionally substituted by fluorine or chlorine atoms;
* -and- (x) indicates the position at which the substituents are bonded.
2. The liquid crystal compound according to claim 1, wherein the liquid crystal compound is one of the following structures LS01-LS 222:
wherein Z is O, si (CH) 3 ) 2 Or CF (CF) 2 。
3. A liquid-crystalline medium, characterized in that it comprises one or more liquid-crystalline compounds as claimed in claim 1 or 2.
4. A liquid crystal medium according to claim 3, characterized in that the liquid crystal medium further comprises one or more compounds of formula II:
wherein,
R 7 、R 8 each independently selected from the group consisting of groups defined by a, b, c:
a：C 1 -C 7 straight-chain alkyl or C 1 -C 7 Straight-chain alkoxy of (a);
b: one or more of the groups in a-CH 2 -a group formed after substitution by-O-, -COO-, -OOC-, or-ch=ch-;
c: one or more hydrogen atoms in any of the groups a are represented by F, cl, -ch=ch 2 or-ch=ch-CH 3 Substituted with a group formed later;
ring B, ring C, ring D, ring E are each independently selected from the group consisting of:
and at least one of the rings B, C, D, E is selected from One of the following;
m, n, o are each independently 0 or 1;
Z 1 、Z 2 、Z 3 each independently selected from the group consisting of single bonds, -C 2 H 4 -*、*-CH＝CH-*、*-C≡C-*、*-COO-*、*-OOC-*、*-CH 2 O-、*-OCH 2 -*、*-CF 2 O-sum-OCF 2 Group of-, Z 1 、Z 2 、Z 3 Any of the hydrogen atoms may be replaced with fluorine atoms.
5. The liquid-crystalline medium according to claim 3 or 4, characterized in that it further comprises one or more compounds of formula III:
wherein R is 9 、R 10 Each independently selected from the group consisting of C 1 -C 10 Alkyl and C of (C) 2 -C 10 Alkenyl group of R 9 、R 10 Any of-CH 2 Can be represented by-CH 2 O-*、*-OCH 2 Instead of-c≡c-, R is R 9 、R 10 Any hydrogen atom in (a) may be replaced with a fluorine atom;
ring F, ring G, ring I, ring J are each independently selected from the group consisting of:
p, q, r are each independently 0 or 1;
Z 4 、Z 5 、Z 6 each independently selected from the group consisting of single bonds, -C 2 H 4 -*、*-CH＝CH-*、*-C≡C-*、*-COO-*、*-OOC-*、*-CH 2 O-*、*-OCH 2 -*、*-CF 2 O-sum-OCF 2 -group of components, Z 4 、Z 5 、Z 6 Any hydrogen atom in (a) may be replaced with a fluorine atom;
* -and- (x) indicates the position at which the substituents are bonded.
6. The liquid crystal medium according to claim 5, wherein the liquid crystal medium comprises 1 to 24% by mass of the liquid crystal compound according to claim 1 or 2, 35 to 58% by mass of the compound of formula II, and 30 to 46% by mass of the compound of formula III.
7. The liquid crystal medium of claim 6, further comprising a functional additive; the functional additive is selected from one or more of antioxidant, chiral agent, light stabilizer and ultraviolet absorber.
8. Consumer product, characterized in that it comprises a liquid-crystalline medium according to any one of claims 3 to 7.
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Citations (4)

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Publication number Priority date Publication date Assignee Title
CN101389634A (en) * 2006-02-22 2009-03-18 住友化学株式会社 Fluorine-containing compound and method for producing same, fluorine-containing polymer, organic thin film, and organic thin film device
CN102898273A (en) * 2012-10-13 2013-01-30 江苏和成显示科技股份有限公司 Novel liquid crystal compound containing hexahydrogen cyclopentadiene, composition containing liquid crystal compound and application of liquid crystal compound
CN109423298A (en) * 2017-08-25 2019-03-05 北京八亿时空液晶科技股份有限公司 A kind of novel dibenzothiophenes liquid-crystal compounds and the preparation method and application thereof
CN113355105A (en) * 2020-03-06 2021-09-07 石家庄诚志永华显示材料有限公司 Liquid crystal compound containing dibenzothiophene and oxygen-containing heterocycle and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101389634A (en) * 2006-02-22 2009-03-18 住友化学株式会社 Fluorine-containing compound and method for producing same, fluorine-containing polymer, organic thin film, and organic thin film device
CN102898273A (en) * 2012-10-13 2013-01-30 江苏和成显示科技股份有限公司 Novel liquid crystal compound containing hexahydrogen cyclopentadiene, composition containing liquid crystal compound and application of liquid crystal compound
CN109423298A (en) * 2017-08-25 2019-03-05 北京八亿时空液晶科技股份有限公司 A kind of novel dibenzothiophenes liquid-crystal compounds and the preparation method and application thereof
CN113355105A (en) * 2020-03-06 2021-09-07 石家庄诚志永华显示材料有限公司 Liquid crystal compound containing dibenzothiophene and oxygen-containing heterocycle and application thereof

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