CN110386912A - A kind of novel dibenzofurans class can poly- property compound and its application - Google Patents
A kind of novel dibenzofurans class can poly- property compound and its application Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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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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- C09K19/00—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
Abstract
The invention belongs to liquid crystal material technical field, being related to a kind of novel dibenzofurans class can poly- property compound and its application.Compound of the present invention has structure shown in general formula I.Use the liquid-crystal compounds or composition containing the liquid-crystal compounds that there are the performances such as wider nematic temperature range, suitable or higher birefringence anisotropy Δ n, higher resistivity, good anti-ultraviolet property, high charge retention rate and low-steam pressure；And the compound is cheap, performance is stablized, and can be widely used for field of liquid crystal display, has important application value.
Description
Technical field
The invention belongs to liquid crystal material technical field, being related to a kind of novel dibenzofurans class poly- property compound and its can be answered
With.
Background technique
In recent years, liquid crystal display device is widely used in various electronic equipments, such as smart phone, tablet computer, automobile
Navigator, television set etc..Representative liquid crystal display mode has twisted-nematic (TN) type, super twisted nematic (STN) type, face inscribe
Change (IPS) type, fringing field switching (FFS) type and vertical orientation (VA) type.Wherein, when VA mode is due to having quickly decline
Between, the image of high contrast, wide viewing angle and high quality, and receive more and more attention.
However, liquid crystal media used in the display element of the active array addressing mode of VA mode etc., there is not for itself
Foot, if image retention level will be significantly worse than the display element of positive dielectric anisotropy, the response time is slow, and driving voltage is relatively high
Deng.To solve the above-mentioned problems, there are some novel VA display technologies, such as MVA technology, PVA technology, PSVA technology.Its
In, PSVA technology had both realized the similar wide view angle display pattern of MVA/PVA, also simplified CF technique, and realizing reduces CF
While cost, aperture opening ratio is improved, higher brightness can also be obtained, and then obtain higher contrast.Further, since whole
The liquid crystal in face has pre-tilt angle, does not have domino delay phenomenon, can also obtain under the driving voltage maintained like faster
Response time, image retention level will not be affected.
The prior art has been found that the application aspect of LC mixture and RMs in PSA display still has the shortcomings that.It is first
It first, is not up to the present that each desired solvable RM is suitable for PSA display: simultaneously, if it is desired to by means of UV
Light is polymerize (this may be advantageous for certain applications) without adding photoinitiator, then selection becomes smaller: in addition,
LC mixture (hereinafter also referred to as " LC body mixture ") combines " material system " to be formed with selected polymerizable components and answers
With minimum rotary viscosity and best photoelectric properties, for increasing " voltage retention " (VHR) to reach effect.In PSVA
Aspect is very important using the high VHR after the irradiation of (UV) light, otherwise will lead to final display and the problems such as image retention occur.
Up to the present, due to there is no inclination angle to occur or occur deficiency after polymerizable unit is too short for UV sensibility wavelength or illumination
The poor problem of homogeneity after illumination of inclination angle or polymerizable components.Not all LC mixture with polymerizable group
The combination being grouped as is adapted to PSVA display.
Therefore, the synthesis and structure-performance relation of the new structural polymerizable compound with excellent properties are ground
Study carefully an important process as field of liquid crystals.
Summary of the invention
The first object of the present invention is to provide a kind of polymerizability compound for polymer stabilizing technology.Contain the change
The liquid-crystal composition orientation effect for closing object is more preferable, and polymerization is more complete, remains lower.And the compound is cheap, performance is stablized,
It can be widely used for field of liquid crystal display, there is important application value.
Liquid-crystal compounds of the present invention, has the following structure:
Wherein, the P1、P2、P3Each independently represent acrylate-based, methacrylate, fluoro acrylic ester
Base, chloropropene perester radical, ethyleneoxy, oxetanyl or epoxy group；
The Z1、Z2、Z3Each independently represent singly-bound ,-O- ,-S- ,-CO- ,-CO-O- ,-O-CO- ,-O-CO-O- ,-CH
=N- ,-N=CH- ,-N=N- ,-C=C-, C1-C12Alkylidene or C2-C12Alkenyl, wherein the C1-C12Alkylidene or
C2-C12Alkenyl in one or more hydrogen atoms can be replaced each independently by F, Cl or CN, and one or more not phase
Adjacent-CH2Group can be each independently by-O- ,-S- ,-NH- ,-CO-, COO- ,-OCO- ,-OCOO- ,-SCO- ,-COS-
Or ethylene linkage is replaced in a manner of not being connected directly mutually；
The L1, L2, L3, L4Each independently represent-F ,-Cl ,-CN ,-NO2、-CH3、-C2H5、-C(CH3)3、-CH
(CH3)2、-CH2CH(CH3)C2H5、-OCH3、-OC2H5、-COCH3、-COC2H5、-COOCH3、-COOC2H5、-CF3、-OCF3、-
OCHF2Or-OC2F5；
r1、r2、r3、r4Each independently represent 0,1,2 or 3.
M, n each independently represents 0 or 1, and m, n are not 0 simultaneously.
In general formula I, about P1、P2、P3: preferably, P1、P2、P3Indicate methacrylate or acrylate-based.
About Z1、Z2、Z3: preferably, Z1、Z2、Z3Each independently representing indicates singly-bound ,-O-, C1-C8Alkylidene or alkane
Oxygroup；It is highly preferred that Z1、Z2、Z3Each independently represent singly-bound ,-O-, C1-C6Alkylidene or alkoxy.
About L1, L2, L3, L4: preferably, L1, L2, L3, L4Each independently represent-F ,-Cl ,-CH3、-C2H5、-C
(CH3)3、-CH(CH3)2、-CH2CH(CH3)C2H5、-OCH3、-OC2H5、-CF3、-OCF3、-OCHF2Or-OC2F5；It is highly preferred that
L1、L2It is identical or different, each independently represent-F ,-Cl；And/or L3, L4Expression-F ,-Cl ,-CH3、-OCH3、-C2H5、-
OC2H5。
About r1、r2、r3、r4: preferably, r1、r2、r3、r4Each independently represent 0,1 or 2；It is highly preferred that r1、r2Respectively
From independently expression 0 or 1.
Polymerizability compound of the present invention, it is preferable that in general formula I, P1、P2、P3Indicate methacrylate
Or it is acrylate-based；
The Z1、Z2、Z3Each independently represent singly-bound ,-O- ,-S- ,-CO- ,-CO-O- ,-O-CO- ,-O-CO-O- ,-CH
=N- ,-N=CH- ,-N=N- ,-C=C-, C1-C12Alkylidene or C2-C12Alkenyl, wherein the C1-C12Alkylidene or
C2-C12Alkenyl in one or more hydrogen atoms can be replaced each independently by F, Cl or CN, and one or more not phase
Adjacent-CH2Group can be each independently by-O- ,-S- ,-NH- ,-CO-, COO- ,-OCO- ,-OCOO- ,-SCO- ,-COS-
Or ethylene linkage is replaced in a manner of not being connected directly mutually；
The L1, L2, L3, L4Each independently represent-F ,-Cl ,-CH3、-C2H5、-C(CH3)3、-CH(CH3)2、-CH2CH
(CH3)C2H5、-OCH3、-OC2H5、-CF3、-OCF3、-OCHF2Or-OC2F5；
r1、r2、r3、r4Each independently represent 0,1 or 2.
M, n each independently represents 0 or 1, and m, n are not 0 simultaneously；
It is further preferred that in general formula I, P1、P2、P3Indicate methacrylate, acrylate-based；
The Z1、Z2、Z3Each independently represent singly-bound ,-O-, C1-C8Alkylidene or alkoxy；
L1、L2It is identical or different, each independently represent-F ,-Cl；
L3, L4Expression-F ,-Cl ,-CH3、-OCH3、-C2H5、-OC2H5；
r1、r2、r3、r4Each independently represent 0,1 or 2.
M, n each independently represents 0 or 1, and m, n are not 0, m+n=1 simultaneously；
It is further preferred that in general formula I, P1、P2、P3Indicate methacrylate, acrylate-based；
The Z1、Z2、Z3Each independently represent singly-bound ,-O-, C1-C6Alkylidene or alkoxy；
L1、L2It is identical or different, each independently represent-F ,-Cl；
L3, L4Expression-F ,-Cl ,-CH3、-OCH3、-C2H5、-OC2H5；
r1、r2Each independently represent 0 or 1；
r3、r4Each independently represent 0,1 or 2；
M, n each independently represents 0 or 1, and m, n are not 0, m+n=1 simultaneously.
As technical solution still more preferably of the invention, in general formula I, wherein m=0, L1、L2、L4For F or
Cl, r1、r2Each independently represent 0 or 1, r4Indicate 0,1 or 2；
Or, m=0, L1、L2For F or Cl, L4Expression-CH3、-OCH3、-C2H5Or-OC2H5One of, r1、r2It is respectively independent
Ground indicates 0 or 1, r4Indicate 1；
Or, n=0, L1、L2、L3For F or Cl, r1、r2Each independently represent 0 or 1, r3Indicate 0,1 or 2；
Or, n=0, L1、L2For F or Cl, L3Expression-CH3、-OCH3、-C2H5Or-OC2H5One of, r1、r2It is respectively independent
Ground indicates 0 or 1, r3Indicate 1；
Preferably, P1、P2、P3Indicate methacrylate or acrylate-based；Z1、Z2、Z3Each independently represent list
Key ,-O-, C1-C6Alkylidene or alkoxy.
As most preferred technique scheme of the invention, the liquid-crystal compounds is selected from one kind of following compound:
Preferably, in general formula I-1~general formula I-56, P1、P2、P3Indicate methacrylate or acrylate-based；Institute
State Z1、Z2、Z3Each independently represent singly-bound ,-O-, C1-C6Alkylidene or alkoxy.
As preferred forms of the invention, the compound is selected from one of following compound:
Second purpose of invention is the composition that protection contains the liquid-crystal compounds.Preferably, the compound is in group
Closing the mass percent in object is 0.01~10%, more preferably 0.01~5%, further preferably 0.1~3%.
The third object of the present invention is that the protection liquid-crystal compounds and the composition containing the liquid-crystal compounds exist
The application of field of liquid crystal display, the application preferably in liquid crystal display device.The liquid crystal display device includes but not
It is limited to TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.It has used the liquid-crystal compounds or has contained the LCD compound
The composition of object has wider nematic temperature range, suitable or higher birefringence anisotropy A n, higher electricity
The performances such as resistance rate, good anti-ultraviolet property, high charge retention rate and low-steam pressure.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention., all other without departing from the present invention
The lower equivalent change or modification completed of revealed spirit, should be included in the scope of the said claims.
Each liquid-crystal compounds used by below in an example unless otherwise instructed, can pass through well known method
Carry out synthesize or obtained from public commercial source, these synthetic technologys be it is conventional, acquired each liquid-crystal compounds accords with after tested
Close standard for electronic compounds.
According to the common detection methods of this field, the various performance parameters of liquid-crystal compounds are obtained by linear fit,
In, the concrete meaning of each performance parameter is as follows:
△ n represents optical anisotropy (25 DEG C)；△ ε represents dielectric anisotropy (25 DEG C, 1000Hz)；γ 1 represents rotation
Turn viscosity (mPa.s, 25 DEG C)；Cp represents clearing point.
Embodiment 1
The structural formula of liquid-crystal compounds are as follows:
The synthetic line of prepare compound BYLC-01 is as follows:
Specific step is as follows:
(1) synthesis of compound BYLC-01-1:
Bromo- 4, the 6- difluorodiphenyl of 40g 3- benzyloxy -7- and furans, 15.5g 3,4- dihydroxy benzenes boron are added in reaction flask
Acid, 14.0g Anhydrous potassium carbonate, 200ml toluene, 150ml ethyl alcohol, 150ml water, tetra- triphenylphosphine of 0.3g close palladium, are heated to reflux anti-
8h is answered, conventional post-processing is carried out, obtains off-white powder (compound BYLC-01-1) 38.5g, HPLC:99.7%, yield
87.1%；
(2) synthesis of compound BYLC-01-2:
38.5g compound BYLC-01-1,90ml toluene, 60ml ethyl alcohol, 1.5g palladium carbon, hydrogen displacement are added in reaction flask
Three times, 30 DEG C~35 DEG C of temperature control plus the de- benzyl 6h of hydrogen, conventional post-processing is carried out, white solid (compound BYLC-01-2) is obtained:
28.1g, LC:99.6%, yield: 94.1%；
(3) synthesis of compound BYLC-01:
Under nitrogen protection, 28.1g compound BYLC-01-2,28.5g triethylamine and 200mL dichloro are added into reaction flask
Methane is cooled to -10 DEG C, and 29.5g methacrylic chloride is added dropwise in -10 DEG C of temperature control~0 DEG C, is warmed to room temperature reaction 6h and falls reaction solution
Enter in water, neutralized with bicarbonate uranium aqueous solution, carry out conventional post-processing, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization is obtained
To white solid (compound BYLC-01) 34.2g, LC:99.8%, yield: 76.4%.
Gained white solid BYLC-01 is analyzed using GC-MS, the m/z of product is 532.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),5.35-6.65(m,6H),7.25-7.95(m,7H)。
Embodiment 2
The structural formula of liquid-crystal compounds are as follows:
The synthetic line of prepare compound BYLC-02 is as follows:
Specific step is as follows:
The synthesis of compound BYLC-02:
Under nitrogen protection, 35.0g compound BYLC-01-2,32.5g triethylamine and 250mL dichloro are added into reaction flask
Methane is cooled to -10 DEG C, and 28.0g acryloyl chloride is added dropwise in -10 DEG C of temperature control~0 DEG C, is warmed to room temperature reaction 6h for reaction solution and pours into water
In, it is neutralized with bicarbonate uranium aqueous solution, carries out conventional post-processing, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization obtains white
Color solid (compound BYLC-02) 42.3g, LC:99.8%, yield: 83.4%.
Gained white solid BYLC-02 is analyzed using GC-MS, the m/z of product is 490.1 (M+).
1H-NMR(300MHz,CDCl3):5.15-5.75(m,3H),5.85-6.45(m,6H),7.15-7.95(m,7H)。
Embodiment 3
The structural formula of liquid-crystal compounds are as follows:
Bromo- 4, the 6- difluorodiphenyl of 3- benzyloxy -7- and furans are replaced with 3- benzyloxy -7- bromine dibenzofurans, reacts item
Part is the same as embodiment 1,2.
Gained white solid BYLC-03 is analyzed using GC-MS, the m/z of product is 454.1 (M+).
1H-NMR(300MHz,CDCl3):5.15-5.75(m,3H),5.85-6.45(m,6H),7.15-7.95(m,9H)。
Embodiment 4
The structural formula of liquid-crystal compounds are as follows:
Bromo- 4, the 6- difluorodiphenyl of 3- benzyloxy -7- and furans are replaced with 3- benzyloxy -7- bromine dibenzofurans, reacts item
Part is the same as embodiment 1,2.
Gained white solid BYLC-04 is analyzed using GC-MS, the m/z of product is 496.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),5.35-6.65(m,6H),7.25-7.95(m,9H)。
Embodiment 5
The structural formula of liquid-crystal compounds are as follows:
3,4- dihydroxy benzenes boric acid is replaced with 3,5- dihydroxy benzenes boric acid, reaction condition is the same as embodiment 1,2.
Gained white solid BYLC-05 is analyzed using GC-MS, the m/z of product is 532.1 (M+).
1H-NMR(300MHz,CDCl3):1.45-2.25(m,9H),5.25-6.55(m,6H),7.15-8.15(m,7H)。
Embodiment 6
The structural formula of liquid-crystal compounds are as follows:
3,4- dihydroxy benzenes boric acid is replaced with 3,5- dihydroxy benzenes boric acid, reaction condition is the same as embodiment 1,2.
Gained white solid BYLC-06 is analyzed using GC-MS, the m/z of product is 490.1 (M+).
1H-NMR(300MHz,CDCl3):5.05-5.65(m,3H),5.75-6.55(m,6H),7.20-8.15(m,7H)。
Embodiment 7
The structural formula of liquid-crystal compounds are as follows:
3,4- dihydroxy benzenes boric acid is replaced with 3,5- dihydroxy benzenes boric acid, 3- benzyloxy -7- bromine dibenzofurans replaces 3-
Bromo- 4, the 6- difluorodiphenyl of benzyloxy -7- and furans, reaction condition is the same as embodiment 1,2.
Gained white solid BYLC-07 is analyzed using GC-MS, the m/z of product is 454.1 (M+).
1H-NMR(300MHz,CDCl3):5.05-5.65(m,3H),5.75-6.55(m,6H),7.20-8.15(m,9H)。
Embodiment 8
The structural formula of liquid-crystal compounds are as follows:
3,4- dihydroxy benzenes boric acid is replaced with 3,5- dihydroxy benzenes boric acid, 3- benzyloxy -7- bromine dibenzofurans replaces 3-
Bromo- 4, the 6- difluorodiphenyl of benzyloxy -7- and furans, reaction condition is the same as embodiment 1,2.
Gained white solid BYLC-08 is analyzed using GC-MS, the m/z of product is 496.1 (M+).
1H-NMR(300MHz,CDCl3):1.45-2.25(m,9H),5.25-6.55(m,6H),7.15-8.15(m,9H)。
Embodiment 9
The structural formula of liquid-crystal compounds are as follows:
Gained white solid BYLC-09 is analyzed using GC-MS, the m/z of product is 514.1 (M+).
1H-NMR(300MHz,CDCl3):1.45-2.25(m,9H),5.25-6.55(m,6H),7.15-8.15(m,8H)。
Embodiment 10
The structural formula of liquid-crystal compounds are as follows:
Gained white solid BYLC-10 is analyzed using GC-MS, the m/z of product is 510.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,12H),5.35-6.65(m,6H),7.25-8.25(m,
8H)。
Embodiment 11
The structural formula of liquid-crystal compounds are as follows:
Gained white solid BYLC-11 is analyzed using GC-MS, the m/z of product is 546.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,12H),5.35-6.65(m,6H),7.25-8.25(m,
6H)。
Embodiment 12
The structural formula of liquid-crystal compounds are as follows:
Gained white solid BYLC-12 is analyzed using GC-MS, the m/z of product is 562.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,12H),5.35-6.65(m,6H),7.25-8.25(m,
6H)。
Embodiment 13
The structural formula of liquid-crystal compounds are as follows:
Gained white solid BYLC-13 is analyzed using GC-MS, the m/z of product is 546.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,6H),4.55-5.25(m,2H),5.55-6.65(m,6H),
7.25-8.25(m,7H)。
Embodiment 14
Gained white solid BYLC-14 is analyzed using GC-MS, the m/z of product is 546.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,6H),4.55-5.25(m,2H),5.55-6.65(m,6H),
7.25-8.25(m,7H)。
Embodiment 15
Gained white solid BYLC-15 is analyzed using GC-MS, the m/z of product is 496.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,6H),4.55-5.25(m,2H),5.55-6.65(m,8H),
7.25-8.25(m,7H)。
Technical solution according to above embodiments, it is only necessary to which the corresponding raw material of simple replacement does not change any substantive behaviour
Make, following liquid-crystal compounds can be synthesized.
Embodiment 16
The property of liquid crystal compound BHR87800 is listed in Table 1 below:
1 mixed crystal BHR87800 property summary sheet of table
Wherein, mixture BHR87800 is purchased from Bayi Space liquid crystal Science and Technology Co., Ltd..The embodiment of addition 0.3%
In the liquid-crystal composition BHR87800 of polymerizable compound BYLC-01 to 99.7% provided by 1, uniform dissolution is mixed
Object PM-1.
The liquid-crystal composition of polymerizable compound BYLC-02 to 99.7% provided by the embodiment 2 of addition 0.3%
In BHR87800, uniform dissolution obtains mixture PM-2.
The liquid-crystal composition of polymerizable compound BYLC-03 to 99.7% provided by the embodiment 3 of addition 0.3%
In BHR87800, uniform dissolution obtains mixture PM-3.
The liquid-crystal composition of polymerizable compound BYLC-05 to 99.7% provided by the embodiment 5 of addition 0.3%
In BHR87800, uniform dissolution obtains mixture PM-4.
The physical property of PM-1, PM-2, PM-3, PM-4 and the physical property of said mixture BHR87800 are almost without difference.It uses
PM-1, PM-2, PM-3, PM-4 injection gap are 4.0 μm and had in the testing cassete of vertical orientation by priming by vacuum method.On one side
Application frequency is 60HZ, and driving voltage is the square wave of 16V, irradiates ultraviolet light to testing cassete with high-pressure mercury ultraviolet lamp on one side, adjusts
The exposure intensity for saving box surface is 30mW/cm2, irradiates 600s, the liquid crystal display element of the vertical orientation after being polymerize makes
Pre-tilt angle is measured with LCT-5016E liquid crystal electro-optic parameter tester, testing cassete is then decomposed, is surveyed using high-efficient liquid phase chromatogram HPLC
Determine remaining polymerizable compound in liquid-crystal composition, is as a result summarized in table 2 and table 3.
Comparative example
In the liquid-crystal composition BHR87800 of the polymerizable compound to 99.7% of the CP of addition 0.3%, uniform dissolution is obtained
To mixture PM-5.The physical property of PM-5 and the physical property of said mixture BHR87800 are almost without difference.Use priming by vacuum method
PM-5 injection gap is 4.0 μm and had in the testing cassete of vertical orientation.Applying frequency on one side is 60HZ, and driving voltage is
The square wave of 16V, irradiates ultraviolet light to testing cassete with high-pressure mercury ultraviolet lamp on one side, and the exposure intensity adjusted to box surface is
30mW/cm2, irradiates 600s, and the liquid crystal display element of the vertical orientation after being polymerize is joined using LCT-5016E liquid crystal electro-optic
Number tester measures pre-tilt angle, then decomposes testing cassete, using remaining in high-efficient liquid phase chromatogram HPLC measurement liquid-crystal composition
As a result polymerizable compound is summarized in table 2 and table 3.
Pre-tilt angle summary sheet before and after 2 UV of table
3 polymer residue data summary table of table
From the correlation data of table 2 and table 3 it is found that polymerizable compound relative polymerization liquid-crystal compounds CP of the invention,
The orientation effect being formed by is more preferable, and faster, polymerization is more complete for rate of polymerization, and residual is lower, so that biggish improve display
Bad problem.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. a kind of novel dibenzofurans class can poly- property compound, which is characterized in that have structure shown in general formula I:
Wherein, the P1、P2、P3Each independently represent acrylate-based, methacrylate, fluoropropenes acid ester group, chlorine
For acrylate-based, ethyleneoxy, oxetanyl or epoxy group；
The Z1、Z2、Z3Each independently represent singly-bound ,-O- ,-S- ,-CO- ,-CO-O- ,-O-CO- ,-O-CO-O- ,-CH=
N- ,-N=CH- ,-N=N- ,-C=C-, C1-C12Alkylidene or C2-C12Alkenyl, wherein the C1-C12Alkylidene or
C2-C12Alkenyl in one or more hydrogen atoms can be replaced each independently by F, Cl or CN, and one or more not phase
Adjacent-CH2Group can be each independently by-O- ,-S- ,-NH- ,-CO-, COO- ,-OCO- ,-OCOO- ,-SCO- ,-COS-
Or ethylene linkage is replaced in a manner of not being connected directly mutually；
The L1, L2, L3, L4Each independently represent-F ,-Cl ,-CN ,-NO2、-CH3、-C2H5、-C(CH3)3、-CH(CH3)2、-
CH2CH(CH3)C2H5、-OCH3、-OC2H5、-COCH3、-COC2H5、-COOCH3、-COOC2H5、-CF3、-OCF3、-OCHF2Or-
OC2F5；
r1、r2、r3、r4Each independently represent 0,1,2 or 3；
M, n each independently represents 0 or 1, and m, n are not 0 simultaneously.
2. compound according to claim 1, which is characterized in that the Z1、Z2、Z3It is single to each independently represent expression
Key ,-O-, C1-C8Alkylidene or alkoxy；
Preferably, Z1、Z2、Z3Each independently represent singly-bound ,-O-, C1-C6Alkylidene or alkoxy.
3. compound according to claim 1 or 2, which is characterized in that the P1、P2、P3Indicate methacrylate or
It is acrylate-based.
4. compound according to claim 1-3, which is characterized in that the L1, L2, L3, L4Table each independently
Show-F ,-Cl ,-CH3、-C2H5、-C(CH3)3、-CH(CH3)2、-CH2CH(CH3)C2H5、-OCH3、-OC2H5、-CF3、-OCF3、-
OCHF2Or-OC2F5。
5. compound according to claim 1-4, which is characterized in that the L1、L2It is identical or different, respectively solely
On the spot expression-F ,-Cl；And/or L3, L4Expression-F ,-Cl ,-CH3、-OCH3、-C2H5Or-OC2H5One of.
6. compound according to claim 1-5, which is characterized in that the r1、r2、r3、r4Table each independently
Show 0,1 or 2；
Preferably, r1、r2Each independently represent 0 or 1.
7. compound according to claim 1-6, which is characterized in that in general formula I, wherein m=0, L1、L2、
L4For F or Cl, r1、r2Each independently represent 0 or 1, r4Indicate 0,1 or 2；
Or, m=0, L1、L2For F or Cl, L4Expression-CH3、-OCH3、-C2H5Or-OC2H5One of, r1、r2Table each independently
Show 0 or 1, r4Indicate 1；
Or, n=0, L1、L2、L3For F or Cl, r1、r2Each independently represent 0 or 1, r3Indicate 0,1 or 2；
Or, n=0, L1、L2For F or Cl, L3Expression-CH3、-OCH3、-C2H5Or-OC2H5One of, r1、r2Table each independently
Show 0 or 1, r3Indicate 1.
8. compound according to claim 1-7, which is characterized in that one kind selected from following compound:
Preferably, the compound is selected from one of following compound:
9. a kind of liquid-crystal composition, which is characterized in that include the described in any item compounds of claim 1-8；
Preferably, the mass percent of the compound in the composition be 0.01~10%, more preferably 0.01~
5%, further preferably 0.1~3%.
10. the described in any item compounds of claim 1-8 and/or composition as claimed in claim 9 are in field of liquid crystal display
Application；Application preferably in liquid crystal display device；It is highly preferred that the liquid crystal display device include TN, ADS, VA,
PSVA, FFS or IPS liquid crystal display.
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| CN110922985A (en) * | 2018-09-20 | 2020-03-27 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition containing novel dibenzofuran polymerizable monomer and application thereof |
| CN114133938A (en) * | 2020-09-04 | 2022-03-04 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| CN114381279A (en) * | 2022-01-17 | 2022-04-22 | 烟台显华科技集团股份有限公司 | Polymerizable compound, composition, and liquid crystal display device |
| WO2023134598A1 (en) * | 2022-01-13 | 2023-07-20 | 烟台显华科技集团股份有限公司 | Polymerisable compound, composition, and liquid crystal display device |
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| CN104797688A (en) * | 2012-11-21 | 2015-07-22 | 默克专利股份有限公司 | Polymerisable compounds and the use thereof in liquid-crystal displays |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110922985A (en) * | 2018-09-20 | 2020-03-27 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition containing novel dibenzofuran polymerizable monomer and application thereof |
| CN114133938A (en) * | 2020-09-04 | 2022-03-04 | 江苏和成显示科技有限公司 | Liquid crystal composition containing polymerizable compound and liquid crystal display device |
| WO2023134598A1 (en) * | 2022-01-13 | 2023-07-20 | 烟台显华科技集团股份有限公司 | Polymerisable compound, composition, and liquid crystal display device |
| CN114381279A (en) * | 2022-01-17 | 2022-04-22 | 烟台显华科技集团股份有限公司 | Polymerizable compound, composition, and liquid crystal display device |
| TWI810035B (en) * | 2022-01-17 | 2023-07-21 | 大陸商煙台顯華科技集團股份有限公司 | Polymeric compound, composition and liquid crystal display device |
| CN114381279B (en) * | 2022-01-17 | 2024-01-30 | 烟台显华科技集团股份有限公司 | Polymerizable compound, composition, and liquid crystal display device |
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