CN114350379A - Novel liquid crystal compound and preparation method and application thereof - Google Patents

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

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CN114350379A
CN114350379A CN202210132206.4A CN202210132206A CN114350379A CN 114350379 A CN114350379 A CN 114350379A CN 202210132206 A CN202210132206 A CN 202210132206A CN 114350379 A CN114350379 A CN 114350379A
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group
branched
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liquid crystal
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曹建华
冯静
郭文龙
边坤
唐怡杰
邸庆童
刘赛赛
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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
    • C09K19/04—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
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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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
    • C09K19/06—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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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • G—PHYSICS
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    • 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
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    • 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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Abstract

The invention relates to the technical field of liquid crystal materials, in particular to a novel liquid crystal compound and a preparation method and application thereof. The liquid crystal compound has a structure shown as 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, effectively improves the display quality, and has important application value.

Description

Novel 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 novel 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 been developed. Taking a television as an example, the television has the characteristics of light weight, small occupied space, convenience in movement and the like, and is also provided with 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 environmental material. At present, the TFT-LCD product technology has matured, and successfully solves the technical problems of viewing angle, resolution, color saturation, brightness, etc., and large-size and medium-and small-size TFT-LCD displays have gradually occupied the mainstream status of flat panel displays in respective fields. However, the requirements for display technology are continuously increasing, and liquid crystal displays are required to achieve faster response, reduce driving voltage to reduce power consumption, and the like, and thus liquid crystal materials are 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 the liquid crystal display, and in order to improve the performance of the material and enable the material to adapt to new requirements, the synthesis of a novel structure liquid crystal compound and the research of the structure-performance relationship become important work in the field of liquid crystal.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The invention aims to provide a liquid crystal compound with a novel structure, which has the characteristics of larger vertical dielectric anisotropy, lower optical anisotropy, lower rotational viscosity, good liquid crystal intersolubility and the like, can be widely used in the field of liquid crystal display, can achieve the application purposes of low power consumption, wide viewing angle and high contrast, effectively improves the display quality, and has important application value; the invention also aims to provide a preparation method and application of the liquid crystal compound.
Specifically, the invention provides the following technical scheme:
the invention provides a liquid crystal compound, which has a structure shown as a general formula I:
Figure BDA0003503161720000011
in the formula I, the compound is shown in the specification,
X1selected from O, S or C (R)5R6)；
R1、R2、R3、R4、R5、R6Each, identically or differently, being selected from hydrogen, deuterium, fluorine, nitrile groups, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl of (a), aryl having 5 to 80, preferably 5 to 60 carbon atoms or heteroaryl having 2 to 60 carbon atoms, and R1And R2Not being simultaneously fluorine, R3And R4Not being fluorine at the same time.
Aryl in the sense of the present invention contains from 5 to 60 carbon atoms and heteroaryl in the sense of the present invention contains from 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl herein is considered to mean a simple aromatic ring, i.e. benzene, biphenyl, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. 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, referred to as aryl or heteroaryl.
Alkyl, alkenyl or alkynyl groups having 1 to 40 carbon atoms in the sense of the present invention are preferably to be understood as meaning the following groups: 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. The alkoxy group, preferably an alkoxy group having 1 to 40 carbon atoms, is considered to mean a methoxy group, a trifluoromethoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a n-pentyloxy group, a sec-pentyloxy group, a 2-methylbutyloxy group, a n-hexyloxy group, a cyclohexyloxy group, a n-heptyloxy group, a cycloheptyloxy group, a n-octyloxy group, a cyclooctyloxy group, a 2-ethylhexyloxy group, a pentafluoroethoxy group and a 2,2, 2-trifluoroethoxy group. The heteroalkyl group is preferably an alkyl group having 1 to 40 carbon atoms, meaning a hydrogen atom or-CH alone2The radicals-which may be substituted by oxygen, sulfur or halogen atoms-are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular 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, 2,2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, propenylthio, butenyloxy, cyclohexenylthio, ethynyloxy, Ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, cycloalkyl radicals according to the inventionCycloalkenyl can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
Preferably, the liquid crystal compound comprises one or more of the structures shown below:
Figure BDA0003503161720000021
Figure BDA0003503161720000031
wherein the content of the first and second substances,
R1、R2、R3、R4each, identically or differently, being selected from hydrogen, deuterium, nitrile, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a), aryl groups having 5 to 80, preferably 5 to 60 carbon atoms or heteroaryl groups having 2 to 60 carbon atoms, in which substituents one or more hydrogen atoms may be replaced by fluorine atoms; and R in the formulae I-2, I-3, I-6, I-7, I-10, I-111And R2Not being simultaneously fluorine, R3And R4Not being fluorine at the same time;
R5、R6each, identically or differently, is selected from hydrogen, deuterium, methyl or ethyl.
Further, the liquid crystal compound is selected from one or more of formulas I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-10, I-11 and I-12.
Preferably, R1、R4Each, identically or differently, being selected from hydrogen, deuterium, nitrile, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a);
R2、R3each, identically or differently, being selected from hydrogen, deuterium, fluorine, nitrile groups, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a);
R5、R6each, identically or differently, is selected from hydrogen, deuterium, methyl or ethyl.
Preferably, when R is1、R4Each, the same or different, is selected from the group consisting of1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Is supported byChain or cyclic alkoxy having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40In the group consisting of alkenyl or alkynyl, R2、R3Each, identically or differently, is selected from hydrogen, fluorine, nitrile groups or methyl groups;
when R is1、R4R, each identically or differently selected from the group consisting of hydrogen, deuterium, fluorine or nitrile groups2、R3Each, the same or different, is selected from the group consisting of1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a).
Further, R5、R6Is hydrogen or methyl; r1And R2Or R3And R4Not simultaneously hydrogen or fluorine, each independently selected from fluorine, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a).
Preferably, the liquid crystal compound comprises one or more of structures LS01-LS294 as shown below:
Figure BDA0003503161720000032
Figure BDA0003503161720000041
Figure BDA0003503161720000051
Figure BDA0003503161720000061
Figure BDA0003503161720000071
Figure BDA0003503161720000081
Figure BDA0003503161720000091
Figure BDA0003503161720000101
Figure BDA0003503161720000111
Figure BDA0003503161720000121
Figure BDA0003503161720000131
Figure BDA0003503161720000141
Figure BDA0003503161720000151
Figure BDA0003503161720000161
the present invention also provides a method for producing the liquid crystal compound described above, wherein:
X1the synthetic route to O is as follows:
Figure BDA0003503161720000162
X1the synthetic route for S is as follows:
Figure BDA0003503161720000163
X1is CR5R6The synthetic route of (2) is as follows:
Figure BDA0003503161720000164
wherein R is1-R6R is methyl or ethyl propylacetate, X is Cl, Br, I or OD; the strong acid is selected from one or more of concentrated sulfuric acid, polyphosphoric acid, methane sulfonic acid, trifluoromethanesulfonic acid and boron trifluoride diethyl etherate; the base is selected from sodium hydroxide, potassium hydroxide, lithium hydroxide, potassium carbonate, sodium carbonate, cesium carbonate, sodium tert-butoxide, potassium tert-butoxide, butyllithium, sodium hydride, potassium hydride, sodium amide, potassium amide, lithium hexamethyldisilazide, sodium hexamethyldisilazide, hexakisOne or more of methyldisilamido potassium.
The raw materials for synthesizing the compound shown in formula I can be purchased from commercial sources, and can also be prepared by referring to the synthesis method of similar compounds provided in org.biomol.chem.,2003, P1609-1624, the method principle, the operation process, the conventional post treatment, the column purification, the recrystallization purification and other means are well known by synthesis personnel in the field, and the synthesis process can be completely realized to obtain the target product.
The reactions of all the steps of all the above processes are carried out in a solvent; the solvent is at least one selected from tetrahydrofuran, 2-methyltetrahydrofuran, N-dimethylformamide, dimethyl sulfoxide, 1-methylpyrrolidin-2-one, ethanol, methanol, dichloromethane, acetone, toluene and deionized water.
The invention also provides a liquid crystal medium which comprises one or more liquid crystal compounds.
Preferably, the liquid-crystalline medium further comprises, as a second component:
Figure BDA0003503161720000165
wherein the content of the first and second substances,
R7、R8each independently selected from the group consisting of the groups defined by A, B, C:
a: having a structure of C1-C7Has a straight-chain alkyl group or has C1-C7Straight chain alkoxy of (a);
b: one or more-CH in any group in A2A group formed after being substituted by-O-, -COO-, -OOC-, or-CH ═ CH-;
c: one or more hydrogen atoms in any group in A are F, Cl, - (CH-CH ═ CH)2or-CH ═ CH-CH3Replacing the latter formed group;
ring B, ring C, ring D, ring E are each independently selected from the group consisting of:
Figure BDA0003503161720000171
Figure BDA0003503161720000172
and at least one of the ring B, the ring C, the ring D and the ring E is selected from
Figure BDA0003503161720000173
One of (1);
m, n, o are each independently 0 or 1;
Z1、Z2、Z3each independently selected from the group consisting of a single bond, — C2H4-*、*-CH＝CH-*、
Figure BDA0003503161720000174
*-COO-*、*-OOC-*、*-CH2O-*、*-OCH2-*、*-CF2O-and-OCF2Any H may be replaced by F;
-and-indicate the position to which the substituent is bonded;
preferably, the liquid-crystalline medium further comprises one or more compounds of the formula III:
Figure BDA0003503161720000175
wherein the content of the first and second substances,
R9、R10each independently selected from the group consisting of1-C10Or with C2-C10Wherein any of-CH2Can be-CH2O-、-OCH2-、
Figure BDA0003503161720000176
Instead, any H atom may be replaced by F;
ring F, ring G, ring I, ring J are each independently selected from the group consisting of:
Figure BDA0003503161720000177
p, q, r are each independently 0 or 1;
Z4、Z5、Z6each independently selected from the group consisting of a single bond, — C2H4-*、*-CH＝CH-*、
Figure BDA0003503161720000178
*-COO-*、*-OOC-*、*-CH2O-*、*-OCH2-*、*-CF2O-and-OCF2Any H may be replaced by F;
and indicates the position to which the substituent is 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%.
Further, the compounds of formula II include compounds represented by the following formulas II-1 to II-15:
Figure BDA0003503161720000179
Figure BDA0003503161720000181
wherein the content of the first and second substances,
R7、R8each independently selected from the group consisting of the groups defined by A, B, C:
a: having a structure of C1-C7Has a straight-chain alkyl group or has C1-C7Straight chain alkoxy of (a);
b: one or more-CH in any group in A2-O-, -COO-, -H-O-, -O-OOC-or-CH-substituted with the radical formed;
c: one or more hydrogen atoms in any group in A are F, Cl, - (CH-CH ═ CH)2or-CH ═ CH-CH3Replacing the latter formed group;
the above ring H1Ring H2Each independently selected from the group consisting of:
Figure BDA0003503161720000182
further, the compounds of formula III include compounds of formulae III-1 to III-16 below:
Figure BDA0003503161720000183
Figure BDA0003503161720000191
wherein R is9、R10Each independently selected from the group consisting of1-C10Or with C2-C10Wherein any of-CH2Can be-CH2O-、-OCH2-、
Figure BDA0003503161720000192
Instead, any H atom may be replaced by F; (F) each independently represents F or H.
Preferably, the liquid-crystalline medium further comprises one or more functional additives; the functional additive comprises an antioxidant, a chiral agent, a light stabilizer or an ultraviolet absorber.
The invention also provides a consumer product comprising a liquid crystalline medium as described above.
The consumer products include, but are not limited to, flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablets, phablets, Personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays less than 2 inches diagonal, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls containing multiple displays tiled together, theater or sports screens, phototherapy devices, and signs.
Unless otherwise specified, all starting materials for use in the present invention are commercially available and any range recited herein includes any endpoints and any numerical values therebetween and any subranges therebetween.
The invention has the following beneficial effects:
due to the rigid structure in the 4, 6-difluoro-substituted or 4-fluoro-substituted or 6-fluoro-substituted dibenzofuran, or dibenzothiophene or fluorene molecule, the liquid crystal molecule bends inwards at the fluoro-substituted side, so that the response speed and solubility of the compound are poor, and the application of the compound is limited. Surprisingly, after difluoro is introduced into 1,9 sites of dibenzofuran or dibenzothiophene or introduced into 4,5 sites of fluorene, fluorine atoms are positioned at the outer sides, so that the liquid crystal compound shows better intersolubility and faster response speed, and the compound shown in the formula I provided by the invention 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 the liquid crystal compound and has important application value.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The examples do not show the specific techniques or conditions, according to the technical or conditions described in the literature in the field, or according to the product specifications. The reagents or instruments used are conventional products available from regular distributors, not indicated by the manufacturer.
In the present invention, the preparation methods are all conventional methods unless otherwise specified. The starting materials used are available from published commercial sources unless otherwise specified, and the percentages are by mass unless otherwise specified. The novel liquid crystal compounds provided by the present invention all reactions are carried out under well-known suitable conditions, and some involve simple organic preparations, for example, the preparation of phenylboronic acid can be synthesized by skilled operating skills, and are not described in detail in the present invention.
Example 1
A process for the preparation of compound LS05, comprising the steps of:
the first step is as follows: preparation of Compound Int-1
Figure BDA0003503161720000201
50.0mmol of 1, 3-difluoro-2-iodo-5- (4-propylcyclohexyl) benzene was dissolved in 80mL of toluene, 55.0mmol of 4-cyclopentyl-2, 3-difluorophenylboronic acid was added, and 1.5mol of anhydrous sodium carbonate and 0.2mmol of Pd (PPh) were added3)4Stirring, heating, refluxing and reacting for 10 hours by 40mL of ethanol and 40mL of water, cooling to room temperature, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-1, namely a white solid, wherein the yield is as follows: 92 percent.
The second step is that: preparation of Compound Int-2
Figure BDA0003503161720000202
Dissolving 20.0mmol of Int-1 in 80mL of dry THF, cooling to-100 ℃ under the protection of nitrogen, dropwise adding 22.0mmol of 2.5M n-butyllithium n-hexane solution, stirring for reacting for 1 hour, further dropwise adding 25.0mmol of triisopropyl borate, stirring and heating to room temperature, adding 20mL of 30% hydrogen peroxide saturated ammonium chloride solution, stirring and reacting for 12 hours at room temperature, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-2, a white solid, and the yield: 87 percent.
The third step: preparation of Compound LS05
Figure BDA0003503161720000203
Under the protection of nitrogen, dissolving 20.0mmol of Int-2 and 50.0mmol of potassium tert-butoxide in 50mL of DMF, heating to 120 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 250mL of water, extracting with ethyl acetate, collecting an organic phase, washing with saturated salt water, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, separating and purifying with a silica gel column, and recrystallizing with ethanol to obtain a compound LS05, which is a white solid and has the yield: 90%, HRMS, m/z: 414.2159[ M ]+]，1HNMR(δ、CDCl3)：7.16～7.14(2H,d)；7.09～7.07(1H,d)；3.78～3.68(1H,m)；2.72～2.63(1H,m)；1.97～1.48(13H,m)；1.46～1.17(8H,m)；0.89(3H,s)。
With reference to the above synthesis method, liquid crystal compounds shown in the following table 1 were prepared:
TABLE 1
Figure BDA0003503161720000204
Figure BDA0003503161720000211
Figure BDA0003503161720000221
Figure BDA0003503161720000231
Example 2
Preparation of compound LS41, comprising the following steps:
the first step is as follows: preparation of Compound Int-4
Figure BDA0003503161720000232
0.11mol of Int-3 prepared in the first and second steps of example 1 was dissolved in 300mL of dry dichloromethane, 0.22mol of triethylamine was added, 0.17mol of N, N-dimethylaminothiocarbonyl chloride was added, the reaction was stirred at room temperature for 12 hours, 500.0mL of saturated saline solution was added, extraction was performed with dichloromethane, the organic phase was collected, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, separated and purified with a silica gel column, and recrystallized from petroleum ether to obtain intermediate Int-4, yield: 85 percent.
The second step is that: preparation of Compound Int-5
Figure BDA0003503161720000233
40.0mmol of intermediate Int-4 was dissolved in 150mL of toluene, and 0.4mmol of Pd (P) was added under nitrogen protectiontBu3)2Heating the catalyst to 100 ℃, stirring and reacting for 10 hours, cooling to room temperature, adding 200.0mL of saturated saline solution, extracting with toluene, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying by using a silica gel column, and recrystallizing in petroleum ether to obtain an intermediate Int-5 with yield: 82 percent.
The third step: preparation of Compound LS41
Figure BDA0003503161720000241
Dissolving 80.0mmol of intermediate Int-5 in 100mL of dimethyl sulfoxide, adding 0.22mol of 60% sodium hydride under the protection of nitrogen, heating to 100 ℃, stirring for reaction for 5 hours, cooling to room temperature, pouring the reaction liquid into 300mL of ice water, filtering, washing a filter cake with water, separating and purifying by using a silica gel column, and recrystallizing in toluene and petroleum ether to obtain a compound LS41 as a white solid, wherein the yield is as follows: 65%, HRMS, m/z:418.1766[M+]，1HNMR(δ、CDCl3)：7.59(2H,s)；7.22(1H,s)；4.22～4.13(1H,m)；4.08～4.05(2H,m)；1.96～1.88(4H,m)；1.82～1.42(9H,m)；1.33～1.19(3H,m)；0.95(3H,s)；0.92(3H,s)。
with reference to the above synthesis method, liquid crystal compounds shown in the following table 2 were prepared:
TABLE 2
Figure BDA0003503161720000242
Figure BDA0003503161720000251
Figure BDA0003503161720000261
Figure BDA0003503161720000271
Figure BDA0003503161720000281
Figure BDA0003503161720000291
Figure BDA0003503161720000301
Example 3
Preparation of compound LS53, comprising the following steps:
the first step is as follows: preparation of Compound Int-7
Figure BDA0003503161720000302
50.0mmol of Int-6, 5.0mmol of palladium acetate, 125.0mmol of NIS and 250mL of dichloroethane are dissolved by stirring, 0.5mol of trifluoroacetic acid and 20.0mmol of 2, 5-bis (trifluoromethyl) aniline are added, the temperature is raised to 60 ℃, the reaction is stirred for 24 hours, the mixture is cooled to room temperature, the mixture is filtered (diatomite), 100mL of saturated aqueous sodium bicarbonate solution is added, an organic layer is separated, an aqueous layer is extracted by dichloromethane, the organic layers are combined, dried and concentrated under reduced pressure, and a residue is separated and purified by a silica gel column to obtain an Int-7 intermediate, a yellow solid, yield: 60 percent.
The second step is that: preparation of Compound Int-8
Figure BDA0003503161720000303
50.0mmol of Int-7 was dissolved in 80mL of toluene, 55.0mmol of 4-ethyl-2-fluorobenzeneboronic acid was added, and 1.5mol of anhydrous sodium carbonate and 0.2mmol of Pd (PPh) were added3)4Stirring, heating, refluxing and reacting for 10 hours by 40mL of ethanol and 40mL of water, cooling to room temperature, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-8, namely a yellow solid, wherein the yield is as follows: 89 percent.
The third step: preparation of Compound Int-9
Figure BDA0003503161720000311
Dissolving 60.0mmol of sodium chlorite and 60.0mmol of hydrated sodium dihydrogen phosphate in 50mL of water, dropwise adding a solution of 20.0mmol of Int-8 in 50mL of tert-butyl alcohol at room temperature, stirring for reaction for 2 hours, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, washing with saturated salt water, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain an intermediate Int-9, namely a white solid, wherein the yield is as follows: 87 percent.
The fourth step: preparation of Compound Int-10
Figure BDA0003503161720000312
Adding 20.0mmol of boric acid into 50mL of concentrated sulfuric acid, cooling to 0 ℃, adding 20.0mmol of Int-9 in batches, stirring for reacting for 2 hours, heating to 55 ℃, stirring for reacting for 2 hours, cooling to room temperature, pouring the reaction liquid into 250mL of ice water, filtering, washing a filter cake with water, and separating and purifying by using a silica gel column to obtain an intermediate Int-10, namely a yellow solid, wherein the yield is as follows: 85 percent.
The fifth step: preparation of Compound LS53
Figure BDA0003503161720000313
20.0mmol of intermediate Int-10 was dissolved in 100mL of dichloromethane, and 5mL of trifluoroacetic acid and 60.0mmol of triethylhydrosilane were added, followed by stirring for 16 hours, concentration under reduced pressure to dryness, separation and purification with silica gel column, and recrystallization with ethanol to obtain compound LS53 as a white solid in yield: 95%, HRMS, m/z: 340.1985[ M ]+]，1HNMR(δ、CDCl3)：7.34(1H,s)；7.22(1H,s)；7.07(1H,s)；6.71(1H,s)；3.79(2H,s)；2.45～2.34(3H,m)；1.85～1.78(4H,m)；1.64～1.23(5H,m)；1.19～1.07(5H,m)；0.86(3H,s)。
With reference to the above synthesis method, liquid crystal compounds shown in the following table 3 were prepared:
TABLE 3
Figure BDA0003503161720000314
Figure BDA0003503161720000321
Figure BDA0003503161720000331
Figure BDA0003503161720000341
Figure BDA0003503161720000351
Examples of mixtures
Examples 4 to 11:
examples 4 to 11 show the preparation methods of different liquid crystal media, wherein the monomer structures, the amounts (weight percentage) of the specific compounds of each example, and the results of the performance parameter tests of the obtained liquid crystal media are respectively shown in the following tables 4 to 11.
The temperature units involved in the examples are, and the specific meanings of the other symbols and the test conditions are as follows:
p. shows the clearing point (. degree. C.) of the liquid crystal, the test apparatus: a Mettler-Toledo-FP System micro thermal analyzer;
γ 1 is rotational viscosity (mPa · s) and the test conditions are: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
K11is a torsional elastic constant, K33For the splay spring constant, the test conditions were: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
Δ ∈ denotes dielectric anisotropy, Δ ∈/∈ where ∈/is the dielectric constant parallel to the molecular axis, ∈ ×) is the dielectric constant perpendicular to the molecular axis, test conditions: at 25 ℃, INSTEC, ALCT-IR1 and 18 micron vertical box;
Δ n represents optical anisotropy, and Δ n ═ no-neWherein n isoRefractive index of ordinary light, neFor the refractive index of extraordinary rays, test conditions: 589nm, 25 + -0.2 deg.C.
In the invention, compounds of general formulas I, II and III are weighed according to the proportion respectively to prepare the liquid crystal medium, wherein the equipment and the instrument 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) a magnetic rotor: is used for stirring;
(5) and (5) controlling the temperature of the electromagnetic stirrer.
The preparation method of the liquid crystal medium comprises the following steps:
(1) the raw materials are orderly placed;
(2) placing the stainless steel beaker on a balance, and placing the compound of formula I into the stainless steel beaker with a small spoon;
(3) sequentially adding other compound raw materials according to the required weight;
(4) placing the stainless steel beaker added with the materials on a magnetic stirring instrument for heating and melting;
(5) and 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.
Table 4 for the component ratios and their performance parameters of the liquid-crystalline medium of example 4;
TABLE 4
Figure BDA0003503161720000361
Figure BDA0003503161720000371
Table 5 shows the component ratios and their performance parameters of the liquid-crystalline medium of example 5;
TABLE 5
Figure BDA0003503161720000372
Table 6 for the component ratios and their performance parameters of the liquid-crystalline medium of example 6;
TABLE 6
Figure BDA0003503161720000373
Figure BDA0003503161720000381
Table 7 for the component ratios and their performance parameters of the liquid-crystalline medium of example 7;
TABLE 7
Figure BDA0003503161720000382
Figure BDA0003503161720000391
Table 8 for the component ratios and their performance parameters of the liquid-crystalline medium of example 8;
TABLE 8
Figure BDA0003503161720000392
Figure BDA0003503161720000401
Table 9 for the component ratios and their performance parameters of the liquid-crystalline medium of example 9;
TABLE 9
Figure BDA0003503161720000402
Figure BDA0003503161720000411
Table 10 for the component ratios and their performance parameters of the liquid-crystalline medium of example 10;
watch 10
Figure BDA0003503161720000412
Table 11 for the component ratios and their performance parameters of the liquid-crystalline medium of example 11;
TABLE 11
Figure BDA0003503161720000413
Figure BDA0003503161720000421
Comparative example 1
The formulation is shown in table 12 below, and the composition does not contain the compound of formula I, but contains the compound of formula IV.
TABLE 12
Figure BDA0003503161720000422
Figure BDA0003503161720000431
As can be seen from the comparison of example 9 with comparative example 1, the compound of the present invention exhibits good miscibility and a very negative dielectric constant as compared with IV, and low temperature stability is improved.
Comparative example 2
The formulation is shown in Table 13 below, which contains not the compound of formula I but the compound of formula V.
Watch 13
Figure BDA0003503161720000432
Figure BDA0003503161720000441
As is clear from the comparison of example 9 with comparative example 2, the compound of the present invention exhibits good miscibility and extremely negative dielectric constant as compared with the conventional liquid crystal having fluorine atoms on the inner side, and low temperature stability is improved.
And (4) conclusion: from the performance parameters of the liquid crystal compositions of the embodiments 4 to 11, the liquid crystal composition provided by the invention has good intersolubility and larger negative dielectric constant, and from the comparison of the comparative example 1 and the comparative example 2, the liquid crystal obtained by transferring the fluorine atom of the 4, 6-difluorodibenzofuran or 4, 6-difluorodibenzothiophene liquid crystal to the 1,9 position or the fluorine atom of the 9, 9-difluorofluorene or 1, 8-difluorofluorene to the 4,5 position shows good intersolubility and low-temperature stability and has larger negative dielectric constant, so that the compound shown in the formula I provided by the invention can be used for improving the intersolubility of the liquid crystal compound, expanding the application range of the liquid crystal mixture and having important application value.
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 (10)

1. A liquid crystal compound having a structure represented by formula I:
Figure FDA0003503161710000011
in the formula I, the compound is shown in the specification,
X1selected from O, S or C (R)5R6)；
R1、R2、R3、R4、R5、R6Each, identically or differently, being selected from hydrogen, deuterium, fluorine, nitrile groups, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl of (a), aryl having 5 to 80, preferably 5 to 60 carbon atoms or heteroaryl having 2 to 60 carbon atoms, and R1And R2Not being simultaneously fluorine, R3And R4Not being fluorine at the same time.
2. The liquid crystal compound of claim 1, comprising one or more of the following structures:
Figure FDA0003503161710000012
Figure FDA0003503161710000021
wherein the content of the first and second substances,
R1、R2、R3、R4each, identically or differently, being selected from hydrogen, deuterium, nitrile, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic chains ofAlkoxy group having the form of C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a), aryl groups having 5 to 80, preferably 5 to 60 carbon atoms or heteroaryl groups having 2 to 60 carbon atoms, in which substituents one or more hydrogen atoms may be replaced by fluorine atoms; and R in the formulae I-2, I-3, I-6, I-7, I-10, I-111And R2Not being simultaneously fluorine, R3And R4Not being fluorine at the same time;
R5、R6each, identically or differently, is selected from hydrogen, deuterium, methyl or ethyl.
3. The liquid crystal compound according to claim 1 or 2, wherein R is1、R4Each, identically or differently, being selected from hydrogen, deuterium, nitrile, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a);
R2、R3each, identically or differently, being selected from hydrogen, deuterium, fluorine, nitrile groups, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Branched or cyclicHeteroalkoxy radical having C2-C40Alkenyl or alkynyl groups of (a);
R5、R6each, identically or differently, is selected from hydrogen, deuterium, methyl or ethyl.
4. The liquid crystal compound according to any one of claims 1 to 3, wherein when R is1、R4Each, the same or different, is selected from the group consisting of1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40In the group consisting of alkenyl or alkynyl, R2、R3Each, identically or differently, is selected from hydrogen, fluorine, nitrile groups or methyl groups;
when R is1、R4R, each identically or differently selected from the group consisting of hydrogen, deuterium, fluorine or nitrile groups2、R3Each, the same or different, is selected from the group consisting of1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a).
5. The liquid crystal compound according to claim 4, wherein R is5、R6Is hydrogen or methyl；R1And R2Or R3And R4Not simultaneously hydrogen or fluorine, each independently selected from fluorine, having C1-C40Straight chain alkyl of (2) having C1-C40Linear alkoxy of (2) having C1-C40Linear heteroalkyl group of (A) having C1-C40Linear heteroalkoxy having C3-C40A branched or cyclic alkyl group having C3-C40Branched or cyclic alkoxy of (2), having C3-C40A branched or cyclic heteroalkyl group of (A) having C3-C40Has C as a branched or cyclic heteroalkoxy group2-C40Alkenyl or alkynyl groups of (a).
6. The liquid crystal compound of any one of claims 1-5, comprising one or more of structures LS01-LS294 as shown below:
Figure FDA0003503161710000031
Figure FDA0003503161710000041
Figure FDA0003503161710000051
Figure FDA0003503161710000061
Figure FDA0003503161710000071
Figure FDA0003503161710000081
Figure FDA0003503161710000091
Figure FDA0003503161710000101
Figure FDA0003503161710000111
Figure FDA0003503161710000121
Figure FDA0003503161710000131
Figure FDA0003503161710000141
Figure FDA0003503161710000151
Figure FDA0003503161710000161
7. a liquid-crystalline medium, characterized in that it comprises one or more liquid-crystalline compounds according to any one of claims 1 to 6;
preferably, the liquid-crystalline medium further comprises one or more compounds of the formula II:
Figure FDA0003503161710000162
wherein the content of the first and second substances,
R7、R8each independently selected from the group consisting of the groups defined by A, B, C:
a: having a structure of C1-C7Has a straight-chain alkyl group or has C1-C7Straight chain alkoxy of (a);
b: one or more-CH in any group in A2A group formed after being substituted by-O-, -COO-, -OOC-, or-CH ═ CH-;
c: one or more hydrogen atoms in any group in A are F, Cl, - (CH-CH ═ CH)2or-CH ═ CH-CH3Replacing the latter formed group;
ring B, ring C, ring D, ring E are each independently selected from the group consisting of:
Figure FDA0003503161710000163
Figure FDA0003503161710000164
and at least one of the ring B, the ring C, the ring D and the ring E is selected from
Figure FDA0003503161710000165
One of (1);
m, n, o are each independently 0 or 1;
Z1、Z2、Z3each independently selected from the group consisting of a single bond, — C2H4-*、*-CH＝CH-*、
Figure FDA0003503161710000166
*-COO-*、*-OOC-*、*-CH2O-*、*-OCH2-*、*-CF2O-and-OCF2Any H may be replaced by F;
-and-indicate the position to which the substituent is bonded;
more preferably, the liquid-crystalline medium further comprises one or more compounds of formula III:
Figure FDA0003503161710000171
wherein the content of the first and second substances,
R9、R10each independently selected from the group consisting of1-C10Or with C2-C10Wherein any of-CH2Can be-CH2O-、-OCH2-、
Figure FDA0003503161710000172
Instead, any H atom may be replaced by F;
ring F, ring G, ring I, ring J are each independently selected from the group consisting of:
Figure FDA0003503161710000173
p, q, r are each independently 0 or 1;
Z4、Z5、Z6each independently selected from the group consisting of a single bond, — C2H4-*、*-CH＝CH-*、
Figure FDA0003503161710000174
*-COO-*、*-OOC-*、*-CH2O-*、*-OCH2-*、*-CF2O-and-OCF2Any H may be replaced by F;
and indicates the position to which the substituent is bonded.
8. The liquid crystal medium of claim 7, wherein the liquid crystal compound is present in an amount of 1-24% by weight, the compound of formula II is present in an amount of 35-58% by weight, and the compound of formula III is present in an amount of 30-46% by weight.
9. Liquid-crystalline medium according to claim 7 or 8, characterized in that it further comprises one or more functional additives; the functional additive comprises an antioxidant, a chiral agent, a light stabilizer or an ultraviolet absorber.
10. A consumer product, characterized in that it comprises a liquid-crystalline medium according to any one of claims 7 to 9.
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