CN109370610A - Liquid-crystal composition and its application containing dibenzofurans and six ring class of an oxygen - Google Patents
Liquid-crystal composition and its application containing dibenzofurans and six ring class of an oxygen Download PDFInfo
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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
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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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- 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
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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Abstract
The present invention relates to a kind of liquid-crystal composition containing dibenzofurans and six ring class of an oxygen and its applications.Liquid-crystal composition includes compound representated by least one excessively a variety of general formula I；Liquid-crystal composition provided by the invention have high contrast, low viscosity, high resistivity, good cryogenic property, fast response speed and with excellent light transmission rate, it is suitable for the displays in VA, ECB, PALC, FFS or IPS mode.
Description
Technical field
The invention belongs to liquid-crystal compounds Material Field, it is related to a kind of liquid-crystal composition, more particularly to a kind of containing dibenzo
The liquid-crystal composition and its application of furans and six ring class of an oxygen.
Background technique
Liquid crystal material is mainly used in the dielectric of liquid crystal display, this is because applied voltage can change this kind of object
The optical property of matter.Electrooptical devices based on liquid crystal are well-known to those skilled in the art.This kind of device is mainly used in
Liquid crystal cell, DPA (orientation mutually deforms) liquid crystal cell with dynamic scattering, guest/principal mode liquid crystal cell, the TN with twisted-nematic structure
Box, STN (super twisted nematic) liquid crystal cell, SBE (super birefringence effect) liquid crystal cell and OMI (light film concerns) liquid crystal cell.It is most common
Display be based on Schadt-Helfrich effect and have twisted-nematic structure.In addition, there is also for be parallel to substrate and
The liquid crystal cell of the electric field operation of liquid crystal surface, such as the novel coplanar switched liquid crystal of display pattern shows (IPS), FFS (Fringe
Field Switching, fringe field switching technique) liquid crystal cell, there are also optical compensation bending mode (OCB), vertical alignment modes
(VA), axial symmetry micro-structure liquid crystal display (ASM), multidomain twisted liquid crystal are shown.
The liquid crystal cell design of various display modes is different, driving method is different, liquid crystal molecule director and glass substrate side
To difference, optical compensation bending mode (OCB), coplanar switched liquid crystal show (IPS) liquid crystal director and glass substrate direction is
Parallel, and vertical alignment mode (VA), axial symmetry micro-structure liquid crystal display (ASM) liquid crystal molecule under no electric field status are directed toward
Resultant glass substrate direction is vertical.
The IPS of parallel arrangement mode, the dielectric anisotropy of liquid crystal molecule can be positive, be also possible to negative；Vertically
Alignment mode (VA) all liquid crystal molecules are when no electric field applies and glass substrate direction is vertical, with vertical incidence light ray parallel.
When polarizing film is orthogonal, can show good dark-state, so such device has good contrast, use the dielectric of liquid crystal respectively to
The opposite sex must be negative.Due to the liquid crystal molecule ratio that in vertically oriented liquid-crystal composition, dielectric anisotropy is negative
(40%~80%) relative to the ratio (10%~60%) of positive liquid crystal molecules in positivity liquid crystal be it is relatively high, which results in
Polarity monocrystalline ingredient is excessively high, and causes the charge conservation rate of VA device etc. and do not reach requirement, and the response time is slower, then having
The liquid crystal monomer of higher dielectric anisotropy absolute value be exactly there is an urgent need to.
Summary of the invention
In order to solve the above technical problems in background technology, the present invention provides one kind have biggish polarity,
Low viscosity, response are fast, have positive effect for the quick response of display device, are very suitable for containing for the allotment of mixed liquid crystal
The liquid-crystal composition and its application of dibenzofurans and six ring class of an oxygen.
To achieve the goals above, the present invention adopts the following technical scheme:
It is a kind of containing dibenzofurans and the liquid-crystal composition of six ring class of an oxygen, it is characterised in that: comprising at least one or
Compound representated by a variety of general formula I；
The general formula I specifically:
In the general formula I, R1、R2It is independent for any one of the group of H, F, Cl, CN or 1.~3.；
1. the group is C1~C12Alkyl or alkoxy, C2~C12Alkenyl or alkenyloxy group；
2. the group is the-CH in the 1. group2By one or more-CH=CH- ,-C ≡ C- ,-COO- ,-
OOC-, cyclopropane, cyclobutane, pentamethylene ,-O- or-S- substitution, and formed after substituting in the form that oxygen atom is not connected directly
Group；
3. the group is the 1. group or 2. the hydrogen atom in group is replaced by one or more fluorine atoms, chlorine atom
After be formed by group；
Z1、Z2Independent is singly-bound or group-CH2CH2,-C ≡ C- ,-CH=CH- ,-O- ,-CF2-CF2-、-CF2-
CH2-、-CH2-CF2,-CF=CF- ,-CH2-、-(CH2)3-、-(CH2)4-、-CH2O-、-OCH2-、-CF2O-、-CH2One in O-
Kind；
Ring A1, ring A2Independent is singly-bound or following group:
M, n is respectively 0,1,2, and m+n≤2.
Compound representated by above-mentioned general formula I is selected from one of I-a of formula, I-b, I-c or I-d or a variety of；
R in the formula I-a~I-d1、R2Independent is H, F, C1~C7Alkyl, alkoxy, C2~C7Alkenyl,
Alkenyloxy group；Wherein, R1、R2In the alkyl, the H atom in alkoxy can replace by one or more fluorine；
Z1、Z2Independent is singly-bound ,-CH2-CH2- ,-CH=CH- ,-OCH2- ,-CH2O- ,-CF2O-、-OCF2In
One kind；
Ring A1, ring A2Independent is singly-bound or following group:
M, n is respectively 1 or 2.
The above-mentioned liquid-crystal composition containing dibenzofurans and six ring class of an oxygen further includes one or more by general formula II institute
The compound of representative；
The general formula II specifically:
Wherein:
R3, R4Independent is C1~C8Alkyl or alkoxy, C2~C8Alkenyl or alkenyloxy group；Wherein, the R3,
R4In one or more hydrogen atoms can be replaced by fluorine atoms；
A3、A4、A5、A6Independent is following group:
I, it is 0 or 1 that j, k are independent, and i+j+k >=1；
Z3、Z4、Z5Independent is singly-bound ,-CH2CH2,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CH2O-、-
OCH2-、-CF2O- ,-OCF2-；Wherein, the Z3、Z4、Z5In one or more hydrogen atoms may be replaced by fluorine atoms；
The weight of the compound as representated by general formula I in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen
Measuring percentage is 1%-60%, and the weight percent of the compound as representated by general formula II is 40%-99%.
In II -1~formula II -10 of formula, R3、R4Independent is C1~C8Alkyl or alkoxy, C2~C8Alkenyl
Or alkenyloxy group；Wherein, the R3、R4In hydrogen atom can be replaced by one or more fluorine atoms；Wherein, (F) is F or H.
The above-mentioned liquid-crystal composition containing dibenzofurans and six ring class of an oxygen further includes one or more by general formula III institute
The compound of representative；
The general formula III specifically:
In the general formula III, R5、R6Independent is C1~C7Alkyl or alkoxy, C2~C7Alkenyl or alkene oxygen
Base；Wherein, the R5、R6In one or more hydrogen atoms can be replaced by fluorine atoms；
A7、A8、A9Independent is following group:
And the A7、A8、A9In at least one expression
P, q respectively indicate 0 or 1, and p+q >=1；
Z6、Z7It is independent to represent singly-bound ,-CH2CH2,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CH2O-、-
OCH2-、-CF2O- ,-OCF2-；Wherein, the Z6、Z7In one or more hydrogen atoms can be replaced by a fluorine atom；
The weight of the compound as representated by general formula I in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen
Measuring percentage is 1%-40%, and the weight percent of the compound as representated by general formula II is 40%-70%, by general formula III institute
The weight percent of the compound of representative is 1~50%.
Include following components in percentage by weight in the above-mentioned liquid-crystal composition containing dibenzofurans and six ring class of an oxygen:
The compound 1~30% as representated by general formula I, the compound 40~70% as representated by general formula II；As representated by general formula III
Compound 5~40%；
It preferably, include following weight percent in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen
Component: the compound 1~30% as representated by general formula I, the compound 45~70% as representated by general formula II；By general formula III
Representative compound 10~30%.
Include following components in percentage by weight in the above-mentioned liquid-crystal composition containing dibenzofurans and six ring class of an oxygen:
The compound 1~25% as representated by general formula Ia, the compound 0~15% as representated by general formula Ib, as representated by general formula II
Compound 45~70%, the compound 10~25% as representated by general formula III；
It preferably, include following weight percent in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen
Component: the compound 1~15% as representated by general formula Ia, the compound 1~15% as representated by general formula Ib, by general formula II institute
The compound 45~70% of representative, the compound 10~25% as representated by general formula III.
Liquid-crystal composition as previously described containing dibenzofurans and six ring class of an oxygen is preparing liquid crystal display device material
Application in material or electro-optical display material, is especially preparing answering in VA, ECB, PALC, FFS or IPS mode display
With.
The invention has the advantages that the liquid-crystal composition provided by the present invention containing dibenzofurans and six ring class of an oxygen,
Those skilled in the art can be according to professional knowledge and device parameter requirements, can after liquid-crystal compounds of the present invention is added
The performance of prediction composition significantly improves, and being embodied in composition has biggish polarity, low viscosity, response fast, right
There is positive effect in the quick response of display device, be very suitable for the allotment of mixed liquid crystal.The present patent application protection simultaneously
The application of above compound and compound in VA, ECB, PALC, FFS or IPS mode.
Specific embodiment
The present invention provides a kind of comprising dibenzofurans and the liquid-crystal composition of six ring class of an oxygen, the liquid-crystal composition packet
Containing compound representated by least one or more of general formula I；
General formula I specifically:
In general formula I, R1、R2It is independent for any one of the group of H, F, Cl, CN or 1.~3.；1. group is
C1~C12Alkyl or alkoxy, C2~C12Alkenyl or alkenyloxy group；2. group is the-CH in 1. group2By one or more
A-CH=CH- ,-C ≡ C- ,-COO- ,-OOC-, cyclopropane, cyclobutane, pentamethylene ,-O- or-S- substitution, and with oxygen after substitution
The group that the form that atom is not connected directly is formed；3. group be 1. group or 2. the hydrogen atom in group by one or more fluorine
Atom, chlorine atom are formed by group after replacing；
Z1、Z2Independent is singly-bound or group-CH2CH2,-C ≡ C- ,-CH=CH- ,-O- ,-CF2-CF2-、-CF2-
CH2-、-CH2-CF2,-CF=CF- ,-CH2-、-(CH2)3-、-(CH2)4-、-CH2O-、-OCH2-、-CF2O-、-CH2One in O-
Kind；
Ring A1, ring A2Independent is singly-bound or following group:
M, n is respectively 0,1,2, and m+n≤2.
Wherein, A1、A2、Z1、Z2There are it is multiple when, can be identical or different；
Due to dibenzofurans and six ring structure of an oxygen itself has mutual restriction effect, and fluorine atom and oxygen atom are fixed on
The side of molecule so that entire molecule has biggish dipole moment, and then shows biggish negative dielectric anisotropic.In addition by
In the introducing of fluorine atom, but also entire molecule have relatively mild clearing point and between other liquid-crystal compounds it is good
Intersolubility.
Compound representated by general formula I has very high dielectric anisotropy absolute value；In addition, change representated by general formula I
Object is closed with the conjugation between biphenyl, therefore is had very high birefringent.Liquid crystal comprising compound representated by general formula I
Composition has biggish dielectric anisotropy absolute value, and suitable optical anisotropy value, wider nematic phase range is low
Rotary viscosity (quick response time) and good UV, visible light photostability, thermal stability and voltage stability, Yi Jiliang
Good low temperature intersolubility.
The present invention is it is further preferred that compound representated by general formula I is selected from one of I-a of formula, I-b, I-c or I-d
Or it is a variety of；
In formula I-a~I-d, R1、R2Independent is H, F, C1~C7Alkyl, alkoxy, C2~C7Alkenyl, alkene oxygen
Base；Wherein, R1、R2In alkyl, the H atom in alkoxy can replace by one or more fluorine；Z1、Z2Independent is single
Key ,-CH2-CH2- ,-CH=CH- ,-OCH2- ,-CH2O- ,-CF2O-、-OCF2One of；
Ring A1, ring A2Independent is singly-bound or following group:
M, n is respectively 1,2.
A1、A2、Z1、Z2There are it is multiple when, can be identical or different；
The present invention is it is further preferred that general formula I is selected from Formulas I-a-1, Formulas I-b-1~Formulas I-b-21, Formulas I-c-1~Formulas I-c-
28, one of compound representated by Formulas I-d-1~Formulas I-d-9 or a variety of；
In Formulas I-a-1, Formulas I-b-1~Formulas I-b-21, Formulas I-c-1~Formulas I-c-29, Formulas I-d-1~Formulas I-d-10, R1、R2
Independent is C1~C7Alkyl, alkoxy, C2~C7Alkenyl, alkenyloxy group.
Usual manner synthesis can be used in compound representated by general formula I of the present invention, it is preferred to use following synthetic route, it is other
Similar structure can also be synthesized with such method.Such as I-a-1 synthetic route are as follows:
Present invention further propose that, liquid-crystal composition leads to also comprising compound representated by one or more general formula II
Formula II specifically:
In general formula II, R3, R4Independent is C1~C8Alkyl or alkoxy, C2~C8Alkenyl or alkenyloxy group；Its
In, R3, R4In one or more hydrogen atoms can be replaced by fluorine atoms；
A3、A4、A5、A6Independent is following group:
I, it is 0 or 1 that j, k are independent, and i+j+k >=1；
Z3、Z4、Z5Independent is singly-bound ,-CH2CH2,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CH2O-、-
OCH2-、-CF2O- ,-OCF2-；Wherein, Z3、Z4、Z5In one or more hydrogen atoms may be replaced by fluorine atoms.
The present invention is it is further preferred that general formula II is selected from one of compound representated by II -1~formula II -10 of formula or more
Kind:
In II -1~formula II -10 of formula, R3、R4Independent is C1~C8Alkyl or alkoxy, C2~C8Alkenyl or alkene
Oxygroup；Wherein, R3、R4In hydrogen atom can be replaced by one or more fluorine atoms；Wherein, (F) is F or H.
Present invention further propose that, liquid-crystal composition further includes compound representated by one or more general formula IIIs；
In general formula III, R5、R6Independent is C1~C7Alkyl or alkoxy, C2~C7Alkenyl or alkenyloxy group；Its
In, R5、R6In one or more hydrogen atoms can be replaced by fluorine atoms；
A7、A8、A9Independent is following group:
And A7、A8、A9In at least one expression
P, q respectively indicate 0 or 1, and p+q >=1；
Z6、Z7It is independent to represent singly-bound ,-CH2CH2,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CH2O-、-
OCH2-、-CF2O- ,-OCF2-；Wherein, Z6、Z7In one or more hydrogen atoms can be replaced by a fluorine atom.
Present invention further propose that, general formula III is selected from one of compound representated by III -1~formula III -11 of formula or more
Kind:
In III -1~formula III -11 of formula, R5、R6Independent is C1~C7Alkyl or alkoxy, C2~C7Alkenyl or
Alkenyloxy group；Wherein, R5、R6In one or more hydrogen atoms can be replaced by fluorine atoms；
A7、A8、A9It is solely independent to represent any one in following group:
Present invention further propose that, it include following components in percentage by weight: 1~40% general formula I in liquid-crystal composition
Representative compound；Compound representated by 40~70% general formula II；Compound representated by 1~50% general formula III；It is preferred that
Ground includes following components in percentage by weight: compound representated by 1~30% general formula I in liquid-crystal composition；40~70% is logical
Compound representated by Formula II；Compound representated by 5~40% general formula IIIs；It is highly preferred that comprising following in liquid-crystal composition
The component of weight percent: compound representated by 1~30% general formula I；Compound representated by 45~70% general formula II；10~
Compound representated by 30% general formula III.
It include following components in percentage by weight: compound representated by 1~25% general formula Ia in liquid-crystal composition；0~
Compound representated by 15% general formula Ib；Compound representated by 45~70% general formula II；Representated by 10~25% general formula IIIs
Compound；It preferably, include following components in percentage by weight: chemical combination representated by 1~15% general formula Ia in liquid-crystal composition
Object；Compound representated by 1~15% general formula Ib；Compound representated by 45~70% general formula II；10~25% general formula III institutes
The compound of representative.
Compound representated by general formula I provided by the invention is preparing liquid crystal compound, liquid crystal display device material or electricity
Application and the liquid crystal compound comprising Formulas I liquid-crystal compounds, liquid crystal display device material or electricity in optical display material
Optical display material, also belongs to protection scope of the present invention.
The other compositions of liquid-crystal composition of the present invention, those skilled in the art can join according to professional knowledge and device
Number requires, and after liquid-crystal compounds of the present invention is added, can appreciate that the performance of composition significantly improves, is embodied in combination
Object has biggish polarity, low viscosity, response fast, has positive effect for the quick response of display device, is very suitable for
The allotment of mixed liquid crystal.The present patent application protection above compound and compound are in VA, ECB, PALC, FFS or IPS mode simultaneously
In application.
Liquid-crystal composition of the present invention, in the dopants of various functions, the preferred 0.01-1% of dopant content can also be added
Between, these dopants are mainly antioxidant, ultraviolet absorbing agent.
Antioxidant, ultraviolet absorbing agent are preferred:
The integral multiple of S expression 1-10
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
In following embodiment, the preparation of liquid-crystal composition is all made of heat of solution method, comprising the following steps: uses balance
Precentagewise weigh liquid-crystal compounds, wherein weigh addition sequence without particular requirement, usually with liquid-crystal compounds fusing point by as low as
High sequence successively weighs mixing, antipyretic at 60~100 DEG C so that each component sufficiently dissolves, and using filter, revolving, finally seals
It fills up to target sample.
Unless otherwise indicated, percentage is weight percentage in the present invention；Temperature unit is DEG C；Δ n represent optics respectively to
Anisotropic (20 DEG C)；Vth represents threshold voltage, is the characteristic voltage (V, 25 DEG C) when relative permeability changes 10%, and RT is represented
Response time is that (ms, 25 DEG C) is measured under the conditions of same as threshold value；Tni represents the clearing point (DEG C) of liquid-crystal composition；
In following embodiment, unit structure code shown in table 1 is indicated in liquid-crystal compounds.
Table 1: the group structure code of liquid-crystal compounds
By taking following compound structure as an example:
It indicates are as follows: 3CCV
It indicates are as follows: 2OM3
It indicates are as follows: 3CPYO2
It indicates are as follows: 2P2M3
Embodiment 1
The structural formula of compound of embodiment 1 such as following formula (a):
Compound a can be synthesized according to conventional mode, the specific steps are as follows:
1) under nitrogen protection, 2- fluorine resorcinol 25.6g, acetic acid the synthesis of 1-1: are sequentially added into 100mL there-necked flask
Reaction solution is acidified by 12.0g, zinc chloride 13.6g, 140 DEG C of reaction 0.5h with dilute hydrochloric acid, and ethyl acetate extraction, concentration obtains pale yellow
Color solid a-1,19.3g, Y=56.8%, GC=98.02%.
2) synthesis of 1-2: sequentially adding a-1 17.0g, n-butanal 8.6g, ethyl alcohol 50mL into 80mL hydrothermal reaction kettle,
Reaction solution is acidified by nafoxidine 7.1g, 150 DEG C of reaction 1h with dilute hydrochloric acid, and toluene extraction is washed to neutrality, dry, crosses silica gel
Column, concentration, obtains light yellow solid a-2,20.3g, Y=90.6%, LC=97.38%.
3) under nitrogen protection, a-2 22.4g, methanol 100mL, boron the synthesis of 1-3: are sequentially added into 250mL there-necked flask
Sodium hydride 5.7g reacts at room temperature 10h, and ammonium chloride solution washed once, and toluene extraction is washed to neutrality, is concentrated, and 2 times of ethyl alcohol are low
Temperature recrystallization, obtains white solid a-3,22.6g, Y=100%, LC=98.52%.
4) under nitrogen protection, a-3 22.6g, toluene 100mL, to toluene the synthesis of 1-4: are added into 250mL there-necked flask
Sulfonic acid 25.8g, reflux water-dividing 2h, reaction solution are washed to neutrality, directly cast single step reaction.
5) under nitrogen protection, the a-4 toluene solution of previous step the synthesis of 1-5: is sequentially added into 250ml single port bottle about
110mL (theory 20.8g containing a-4), ethyl alcohol 50mL, 5%Pd/C 1.0g lead to hydrogen, 30 DEG C of magnetic agitation 10h, by reaction solution
Filtering, concentration, obtains colourless liquid a-5 19.3g, Y=91.9%, GC=98.83%.
6) synthesis of 1-6: a-5 10.5g is sequentially added into 100ml there-necked flask, DMF 50mL, NBS 9.8g, 60 DEG C anti-
4h is answered, reaction solution is poured into water, ethyl acetate extraction is concentrated, and 1 times of ethyl alcohol recrystallization obtains light yellow solid a-6,12.4g, Y
=85.5%, GC=98.27%.
7) under nitrogen protection, a-6 14.5g, 4- ethyoxyl -2,3- the synthesis of 1-7: are sequentially added into 100ml there-necked flask
Difluoro phenyl boric acid 12.1g, potassium carbonate 10.4g, TBAB 1.0g, Pd (0) 0.2g, ethyl alcohol 30mL, water 30mL, back flow reaction 3h, will
Reaction solution is acidified with dilute hydrochloric acid, toluene extraction, concentration, and 4 times of ethyl alcohol recrystallizations obtain white solid a-7,10.8g, Y=59.0%,
GC=99.35%.
8) under nitrogen protection, a-7 18.3g, DMF 60mL, potassium carbonate the synthesis of a: are sequentially added into 100ml there-necked flask
13.8g, back flow reaction 2h, reaction solution is poured into water, toluene extraction, concentration, and 5 times of normal heptanes recrystallize 2 times, excessively silicagel column, and 5
Times normal heptane weighs 1 time again, obtains white solid a, 6.6g, Y=38.2%, GC=99.9%.
Embodiment 2
Technical solution according to embodiment 1, it is only necessary to simply replace corresponding raw material, not change any substantive operations
Following liquid-crystal compounds can be synthesized:
Embodiment 3
The weight percent of each component when performance parameter in 2 liquid crystal compound of table
Embodiment 4
The weight percent of each component when performance parameter in 3 liquid crystal compound of table
Embodiment 5
The weight percent of each component when performance parameter in 4 liquid crystal compound of table
Embodiment 6
The weight percent of each component when performance parameter in 5 liquid crystal compound of table
Embodiment 7
The weight percent of each component when performance parameter in 6 liquid crystal compound of table
Embodiment 8
The weight percent of each component when performance parameter in 7 liquid crystal compound of table
Embodiment 9
The weight percent of each component when performance parameter in 8 liquid crystal compound of table
Comparative example 1
The weight percent of each component when performance parameter in 9 liquid crystal compound of table
The performance parameter of the liquid-crystal composition as shown in embodiment 3-9 can see, LCD compound provided by the present invention
Object and its derivative have good intersolubility and great negative dielectric constant, and the use of negativity monocrystalline can be greatly reduced
Amount, and then substituted with non-polar single crystalline, so as to improve its response time；Due to the conjugation of its biphenyl structural, provide very
Big optical anisotropy, therefore the intersolubility for improving liquid-crystal compounds reduce threshold value, increase birefringent suffer from well
Effect, have important application value and application prospect, can be used in liquid crystal display device.
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 liquid-crystal composition containing dibenzofurans and six ring class of an oxygen, it is characterised in that: comprising at least one or more
Compound representated by kind general formula I；
The general formula I specifically:
In the general formula I, R1、R2It is independent for any one of the group of H, F, Cl, CN or 1.~3.；
1. the group is C1~C12Alkyl or alkoxy, C2~C12Alkenyl or alkenyloxy group；
2. the group is the-CH in the 1. group2By one or more-CH=CH- ,-C ≡ C- ,-COO- ,-OOC-, ring
Propane, cyclobutane, pentamethylene ,-O- or-S- substitution, and the group formed after substituting in the form that oxygen atom is not connected directly；
3. group institute after the hydrogen atom in group is replaced by one or more fluorine atoms, chlorine atom for the 1. group or 2.
The group of formation；
Z1、Z2Independent is singly-bound or group-CH2CH2,-C ≡ C- ,-CH=CH- ,-O- ,-CF2-CF2-、-CF2-
CH2-、-CH2-CF2,-CF=CF- ,-CH2-、-(CH2)3-、-(CH2)4-、-CH2O-、-OCH2-、-CF2O-、-CH2One in O-
Kind；
Ring A1, ring A2Independent is singly-bound or following group:
M, n is respectively 0,1,2, and m+n≤2.
2. the liquid-crystal composition according to claim 1 containing dibenzofurans and six ring class of an oxygen, it is characterised in that: institute
It states compound representated by general formula I and is selected from one of I-a of formula, I-b, I-c or I-d or a variety of；
R in the formula I-a~I-d1、R2Independent is H, F, C1~C7Alkyl, alkoxy, C2~C7Alkenyl, alkene oxygen
Base；Wherein, R1、R2In the alkyl, the H atom in alkoxy can replace by one or more fluorine；
Z1、Z2Independent is singly-bound ,-CH2-CH2- ,-CH=CH- ,-OCH2- ,-CH2O- ,-CF2O-、-OCF2In one
Kind；
Ring A1, ring A2Independent is singly-bound or following group:
M, n is respectively 1 or 2.
3. the liquid-crystal composition according to claim 2 containing dibenzofurans and six ring class of an oxygen, which is characterized in that institute
General formula I is stated to be selected from representated by Formulas I-a, Formulas I-b-1~Formulas I-b-21, Formulas I-c-1~Formulas I-c-29, Formulas I-d-1~Formulas I-d-9
One of compound is a variety of:
R in the Formulas I-a, Formulas I-b-1~Formulas I-b-21, Formulas I-c-1~Formulas I-c-29 and Formulas I-d-1~Formulas I-d-101、R2
Independent is C1~C7Alkyl, alkoxy, C2~C7Alkenyl or alkenyloxy group.
4. the liquid-crystal composition according to claim 1 or 2 or 3 containing dibenzofurans and six ring class of an oxygen, feature
Be: the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen further includes one or more as representated by general formula II
Compound；
The general formula II specifically:
Wherein:
R3, R4Independent is C1~C8Alkyl or alkoxy, C2~C8Alkenyl or alkenyloxy group；Wherein, the R3, R4In
One or more hydrogen atoms can be replaced by fluorine atoms；
A3、A4、A5、A6Independent is following group:
I, it is 0 or 1 that j, k are independent, and i+j+k >=1；
Z3、Z4、Z5Independent is singly-bound ,-CH2CH2,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CH2O-、-
OCH2-、-CF2O- ,-OCF2-；Wherein, the Z3、Z4、Z5In one or more hydrogen atoms may be replaced by fluorine atoms；
The weight hundred of the compound as representated by general formula I in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen
Dividing ratio is 1%-60%, and the weight percent of the compound as representated by general formula II is 40%-99%.
5. the liquid-crystal composition according to claim 4 containing dibenzofurans and six ring class of an oxygen, it is characterised in that: institute
It states general formula II and is selected from one of compound representated by II -1~formula II -10 of formula or a variety of:
In II -1~formula II -10 of formula, R3、R4Independent is C1~C8Alkyl or alkoxy, C2~C8Alkenyl or alkene
Oxygroup；Wherein, the R3、R4In hydrogen atom can be replaced by one or more fluorine atoms；Wherein, (F) is F or H.
6. the liquid-crystal composition according to claim 5 containing dibenzofurans and six ring class of an oxygen, it is characterised in that: institute
Stating the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen further includes one or more chemical combination as representated by general formula III
Object；
The general formula III specifically:
In the general formula III, R5、R6Independent is C1~C7Alkyl or alkoxy, C2~C7Alkenyl or alkenyloxy group；Its
In, the R5、R6In one or more hydrogen atoms can be replaced by fluorine atoms；
A7、A8、A9Independent is following group:
And the A7、A8、A9In at least one expression
P, q respectively indicate 0 or 1, and p+q >=1；
Z6、Z7It is independent to represent singly-bound ,-CH2CH2,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CH2O-、-
OCH2-、-CF2O- ,-OCF2-；Wherein, the Z6、Z7In one or more hydrogen atoms can be replaced by a fluorine atom；
The weight hundred of the compound as representated by general formula I in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen
Dividing ratio is 1%-40%, and the weight percent of the compound as representated by general formula II is 40%-70%, as representated by general formula III
The weight percent of compound be 1~50%.
7. the liquid-crystal composition according to claim 6 containing dibenzofurans and six ring class of an oxygen, it is characterised in that: institute
It states general formula III and is selected from one of compound representated by III -1~formula III -11 of formula or a variety of:
In III -1~formula III -11 of formula, R5、R6Independent is C1~C7Alkyl or alkoxy, C2~C7Alkenyl or alkene oxygen
Base；Wherein, the R5、R6In one or more hydrogen atoms can be replaced by fluorine atoms；
A7、A8、A9It is solely independent to represent any one in following group:
8. the liquid-crystal composition according to claim 7 containing dibenzofurans and six ring class of an oxygen, it is characterised in that: institute
It states in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen comprising following components in percentage by weight: by general formula I institute
The compound 1~30% of representative, the compound 40~70% as representated by general formula II；The compound 5 as representated by general formula III~
40%；
It preferably, include the group of following weight percent in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen
Point: the compound 1~30% as representated by general formula I, the compound 45~70% as representated by general formula II；By general formula III institute's generation
The compound 10~30% of table.
9. the liquid-crystal composition according to claim 8 containing dibenzofurans and six ring class of an oxygen, it is characterised in that: institute
It states in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen comprising following components in percentage by weight: by general formula Ia institute
The compound 1~25% of representative, the compound 0~15% as representated by general formula Ib, the compound 45 as representated by general formula II~
70%, the compound 10~25% as representated by general formula III；
It preferably, include the group of following weight percent in the liquid-crystal composition containing dibenzofurans and six ring class of an oxygen
Point: the compound 1~15% as representated by general formula Ia, the compound 1~15% as representated by general formula Ib, as representated by general formula II
Compound 45~70%, the compound 10~25% as representated by general formula III.
10. the liquid-crystal composition according to any one of claims 1 to 9 containing dibenzofurans and six ring class of an oxygen is in preparation solution
Application in crystal display device material or electro-optical display material, especially in preparation VA, ECB, PALC, FFS or IPS mode
Application in display.
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| CN115746871A (en) * | 2022-11-16 | 2023-03-07 | Tcl华星光电技术有限公司 | Liquid crystal composition and liquid crystal display panel |
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