CN106543178A - A kind of compound, liquid-crystal composition and liquid crystal display - Google Patents
A kind of compound, liquid-crystal composition and liquid crystal display Download PDFInfo
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- CN106543178A CN106543178A CN201510590984.8A CN201510590984A CN106543178A CN 106543178 A CN106543178 A CN 106543178A CN 201510590984 A CN201510590984 A CN 201510590984A CN 106543178 A CN106543178 A CN 106543178A
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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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
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- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3483—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a non-aromatic ring
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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Abstract
The invention discloses a kind of compound, liquid-crystal composition and liquid crystal display.Compound of the invention is shown in formula I：Wherein, R1And R2It is independently selected from the alkyl or alkoxyl of hydrogen atom or 1～15 carbon atom；A, B and C are each independently selected from following radicals：Z1And Z2It is each independently selected from：Singly-bound ,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-C2F4-、-(CH2)4- and-CF=CF-；A, b, c, d and e are each independently selected from 0,1 and 2.Liquid-crystal composition of the invention at least includes a kind of compound of the invention.Liquid crystal display of the invention contains liquid-crystal composition of the invention.
Description
Technical field
The present invention relates to field of liquid crystal display, more particularly to a kind of compound, liquid-crystal composition and liquid crystal display
Device.
Background technology
According to different display modes, liquid crystal display be divided into dynamic shine type, distortion type, supertwist type and
Plane conversion type.Although different type liquid crystal display requires that liquid-crystal composition has different qualities, also to
Ask which that there are following general character：Appropriate optical anisotropy, appropriate rotary viscosity and response speed faster.
Liquid-crystal composition is mixed by plurality of liquid crystals compound, therefore the performance of liquid-crystal compoundss monomer shows
Obtain particularly important.Existing liquid-crystal composition is relatively low due to clearing point, it is impossible to meet liquid crystal display in high temperature
The requirement used under state, and there is a problem of using temperature range narrower.
It is therefore desirable to provide a kind of compound that can improve liquid-crystal composition clearing point.
The content of the invention
The invention provides liquid-crystal composition clearing point is not high during a kind of liquid-crystal compoundss solve prior art
Problem；Liquid crystal display is solved there is provided a kind of liquid-crystal composition and liquid crystal display can not be in high temperature shape
Use under state and the narrower problem of operating temperature range.
According to an aspect of the present invention, there is provided a kind of compound, the compound is shown in formula I：
Wherein,
R1And R2It is independently selected from the alkyl or alkoxyl of hydrogen atom or 1～15 carbon atom；
A, B and C are each independently selected from following radicals：
Z1And Z2It is each independently selected from：Singly-bound ,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CF2O-、
-OCH2-、-CH2O-、-OCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-C2F4-、-(CH2)4-
With-CF=CF-；
A, b, c, d and e are each independently selected from 0,1 and 2.
Alternatively, compound of the invention, the one or more-CH in the alkyl or alkoxyl2-
Substituted by-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-O- or Tetramethylene. independently of one another.
Alternatively, compound of the invention, in the alkyl or alkoxyl, one or more hydrogen are each only
On the spot replaced by fluorine and/or chlorine.
Alternatively, compound of the invention, the alkyl or alkoxyl independently of one another by CN, OCN,
OCF3、CHF2、OCHF2, SCN, NCS or SF5Replace.
According to a further aspect in the invention, there is provided a kind of liquid-crystal composition, the liquid-crystal composition at least include
A kind of compound of the invention.
Alternatively, liquid-crystal composition of the invention, the liquid-crystal composition are included by weight percentage
The compound of the invention of 5-40%.
Alternatively, liquid-crystal composition of the invention, the liquid-crystal composition are included by weight percentage
The compound of the 15-30% present invention.
According to a further aspect in the invention, there is provided a kind of liquid crystal display, containing liquid crystal of the invention
Compositionss.
Beneficial effects of the present invention are as follows：
Compound of the invention introduces the rigid structure of azabicyclo-octane, therefore makes chemical combination of the present invention
Thing has high clearing point, and the fusing point of liquid-crystal composition is completely below what is normally used typically below -10 DEG C
Temperature range, so fusing point is on affecting little using temperature, therefore improves clearing point, that is, improves liquid crystal
The operating temperature range of compositionss；The compounds of this invention is applied in liquid-crystal composition, liquid crystal group is improve
The clearing point of compound, also improves the operating temperature range of liquid-crystal composition.The liquid-crystal composition is applied to
In liquid crystal display, meet what liquid crystal display was worked at high temperature as liquid-crystal composition clearing point is improved
Demand, also improves the temperature range of liquid crystal display operation.
Description of the drawings
Nuclear magnetic spectrograms of the Fig. 1 for compound e；
Nuclear magnetic spectrograms of the Fig. 2 for compound j.
Specific embodiment
Specific embodiment is only the description of the invention, and does not constitute the restriction to present invention, below
Accompanying drawing will be combined and specific embodiment will be further described to the present invention and will describe.
The invention provides a kind of compound, the compound is shown in formula I：
Wherein,
R1And R2It is independently selected from the alkyl or alkoxyl of hydrogen atom or 1～15 carbon atom；
A, B and C are each independently selected from following radicals：
Z1And Z2It is each independently selected from：Singly-bound ,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CF2O-、
-OCH2-、-CH2O-、-OCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-C2F4-、-(CH2)4-
With-CF=CF-；
A, b, c, d and e are each independently selected from 0,1 and 2.
Compound of the invention introduces azabicyclo-octane rigid structure, makes the compound have high definition
Bright spot, also improves the operating temperature range of liquid-crystal composition；The compound is applied in liquid-crystal composition,
The clearing point of liquid-crystal composition can be improved, the operating temperature range of liquid-crystal composition is also improved；By liquid crystal group
Compound is applied in liquid crystal display, is met the demand that liquid crystal display is worked at high temperature, be have also been enlarged
The temperature range of liquid crystal display operation.
According to the compound of one embodiment of the present invention, the one or more-CH in alkyl or alkoxyl2-
Substituted by-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-O- or Tetramethylene. independently of one another.
According to the compound of one embodiment of the present invention, in alkyl or alkoxyl, one or more hydrogen are each only
On the spot replaced by fluorine and/or chlorine.
According to the compound of one embodiment of the present invention, alkyl or alkoxyl independently of one another by CN,
OCN、OCF3、CHF2、OCHF2, SCN, NCS or SF5Replace.
Compound of the invention, is expressed as I in preferred table a1-I12Compound：
Table a
In the compound I shown in table a1～I12In, R1For hydrogen or carbon number for 1-10 straight chained alkyl or alkane
Epoxide；(F) represent there is fluorine atom substituent on phenyl ring or for hydrogen；R2It is that hydrogen or carbon number are the straight of 1-10
Alkyl group or alkoxyl, or Cl, F, CN, OCF3、CF3、SCN、CHF2、OCHF2。
Applicant has been carried out synthesizing and has been characterized to compound shown in the application Formulas I, and here enumerates two kinds of materializations
The synthetic method and characterize data of compound.
In the synthetic method of following two kinds of compounds, material therefor is obtained if no special instructions from commercial channels
.Wherein in embodiment disclosed below and embodiment：
GC represents gas chromatographic purity；
MS represents mass spectrum；
MPRepresent fusing point；
CPRepresent clearing point；
△ ε represent dielectric anisotropy；
△ n represent optical anisotropy；
γ1Represent rotary viscosity；
Gained compound mass spectrum obtained by GC-MS and gas chromatogram are come identifying description；
QP2010SE type of the GC-MS analysis determining instruments for Shimadzu Corporation；
The instrument that fusing point is used is the micro- thermal analyzers of WRX-1S, sets heating rate as 3 DEG C/min；Clearly
Bright spot employs conventional method of testing.
The physical property measurement method of compound：
1. optical anisotropy
Using Abbe refractometer, it is measured under 25 DEG C, 589nm wavelength conditions.
The surface of headprism is rubbed in same direction, sample is added drop-wise on headprism after friction.Folding
Penetrate rate n11Determine when polarization direction is parallel with frictional direction；Refractive index n⊥In polarization direction and frictional direction
Determine when vertical；Optical anisotropy △ n pass through formula △ n=n11-n⊥Calculate.
2. dielectric constant anisotropy
It is measured using the instrument of Hewlett-Packard's model HP4284a.
At 25 DEG C, liquid crystal molecule is determined in axial dielectric constant ∑11, and liquid crystal molecule short-axis direction
Dielectric constant ∑⊥, dielectric constant anisotropy is by formula △ ∑s=∑11-∑⊥Calculate.
The particular compound of synthesis just like shown in formula e：
Applicant is designed as to the synthetic route of compound shown in formula e：
Specific synthesis step includes：
Step 1：
The synthesis of 3- (3,5- difluorobenzene) -8- methyl -8- azepines [3.2.1] double-octane -3- alcohol (compound a).
Add in 2L there-necked flasks 28.8g (1.2mol, 1.2eq) brand-new magnesium chips and 200mL dry tetrahydrofurans,
2 iodine are heated to backflow as initiator, and Deca 19.3g (0.1mol) 3,5- difluoro bromobenzenes cause, treat
After causing grignard reaction, reaction gentle reflux is kept, continues Deca 212.3g (1.1mol, common 1.2eq) 3,5-
Difluoro bromobenzene is dissolved in 500mL dry tetrahydrofuran solvents.30 minutes, then Deca are maintained the reflux for after finishing
139.2g (1mol, 1eq) tropinone is dissolved in 500mL dry tetrahydrofuran solvents, keeps reaction slight
Backflow, maintains the reflux for 3 hours again, is down to room temperature, pours reactant liquor into 1000g under stirring after completion of dropping
It is hydrolyzed in the mixed liquor of frozen water and 3mol hydrochloric acid, stirs 30 minutes, point liquid takes upper organic phase,
With 500mL toluene by aqueous extraction twice, merge organic faciess.It is organic with 3 washings of 1L deionizations moisture
Phase, after anhydrous sodium sulfate drying, vacuum water-bath is distilled off solvent, obtains 260g colourless liquids, as
Compound a.
Step 2：
3- (3,5- difluorobenzenes) -8- methyl -8- azepines [3.2.1] double-octane -3- alkene (synthesis of compound b)；
In 2L there-necked flasks, add 260g compound as obtained in step 1 as reactant, 20g to toluene
As dehydrant, 1.2L toluene as solvent, reflux water-dividing stopped after 3 hours sulfonic acid, was down to room temperature, plus
Enter saturated sodium bicarbonate solution 200mL, stirring divides liquid after 10 minutes, takes upper organic phase, use 500mL
Deionized water washs organic faciess at twice, is directly entered by 10 centimetres of silicagel columns with after anhydrous sodium sulfate drying
Row column chromatography, afterwards using 200mL toluene eluting, water-bath vacuum distilling removes neat solvent, adds 200mL
The mixed solvent of toluene and 400mL ethanol carries out recrystallization, and room temperature is separated out, and then freezes 4 in refrigerator
Hour, 207.1g (0.88mol) compound b is filtrated to get, for 88.0%, GC, its yield detects which is pure
Spend for 99.2%.
Step 3：
(compound c) synthesizes 3- (3,5- difluorobenzenes) -8- methyl -8- azepines [3.2.1] double-octanes.
207.1g (0.88mol) compound c, addition 600mL that step 2 is obtained are added in 2L hydriding reactors
Toluene and 300mL ethanol as mixed solvent, 10g palladium carbons as catalyst, after covering the kettle cover of hydriding reactor
With hydrogen air-discharging 5 times, pressure 3.5Mpa is hydrogenated with to kettle, 120 DEG C are warming up to, stir hydrogenation reaction 8
Hour, reaction finishes, is cooled to less than 40 DEG C, is filtered to remove palladium carbon, washs filter cake with 300mL toluene,
Filtrate revolving after merging is removed into solvent, weak yellow liquid 197.5g (0.83mol), as chemical combination is obtained
Thing c, yield are that 94.6%, GC detects that its purity is 99.5%.
Step 4：
3- (4- (bromine difluoro methyl)) -3,5- difluorobenzene -8- methyl -8- azepines [3.2.1] double-octanes (changes
The synthesis of compound d).
To in 2L there-necked flasks, add 197.5g (0.83mol, 1eq) compound c, 600mL to be dried tetrahydrochysene furan
Mutter as solvent, lead to nitrogen protection, be cooled to -60 DEG C, Deca 364ml 2.5M (0.91mol, 1.09eq)
N-BuLi, -55 DEG C～-60 DEG C of Deca process temperature control, drop are finished, and continue temperature control stirring and react 1 hour.Drop
Extremely -70 DEG C of temperature, Deca 261.2g (1.25mol, 1.50eq) difluorodibromomethane, -65 DEG C of Deca process temperature control～
- 70 DEG C, drop finishes, and continues temperature control stirring and reacts 30 minutes, is warming up to room temperature, adds 200mL concentrated hydrochloric acid to adjust
Section pH value, 500mL water are hydrolyzed, and then carry out a point liquid, extract water phase two with 500mL ethyl acetate
It is secondary, merge organic faciess and be washed to neutrality, solvent evaporated obtains weak yellow liquid 212.7g (0.58mol), i.e.,
For compound d, GC detects its purity for 82.6%, and yield is 70.1%.
Step 5：
3- (4- (3,4,5- trifluorophenyls) difluoro-methoxy) -3,5- difluorobenzenes -8- methyl -8- azepines [3.2.1] is double
(compound e) synthesizes cyclooctane.
212.7g (0.58mol, 1eq) compound d is added in reaction bulb, 500ml DMSO are used as molten
Agent, 160.3g (1.16mol, 2eq) Anhydrous potassium carbonate, 3,4,5- trifluoro-benzenes of 103.1g (0.70mol)
Phenol (reactant), is heated with stirring to 65～70 DEG C and reacts 2 hours.Room temperature is cooled to, filter solid is crossed, and
Filter cake is rinsed with 300mL dichloromethane, filtrate adds 1L water, and stirring, point liquid use 500mL dichloros
Methane extracts water layer twice, and washing organic faciess are to neutrality, solvent evaporated.Concentrate is dissolved in 500mL toluene
In, cross silicagel column and decolourize, eluting is carried out with 300mL toluene, collect eluent and solvent is evaporated off, gained
Thing dehydrated alcohol recrystallization 3 times, obtains white crystal 100.5g (0.23mol), as compound e,
GC detects that its purity is 99.5%, yield 42.5%.
The design parameter of compound e of the applicant to obtaining is determined, and measurement result is as follows：
MP：68℃；
CP：121℃；
△ε：21.0；
△n：0.18；
MS：124.11 (1.2%), 414.13 (10.5%), 433.13 (100.0%), 434.13 (23.7%),
435.13 (2.9%)；
Fig. 1 is the nuclear magnetic spectrogram of the compound, and the nuclear magnetic spectrogram is resolved to：
1H NMR(400MHz,d6-DMSO)：δ 6.85 (s, 1H), 6.71 (d, J=10.0Hz, 4H),
6.57 (d, J=14.1Hz, 4H), 3.75 (s, 1H), 2.96 (s, 3H), 2.73 (s, 6H), 2.08 (s, 4H),
1.99 (s, 3H), 1.85～1.60 (m, 5H), 1.53～1.17 (m, 9H), 0.98 (s, 1H).
According to said determination result, it can be seen that：
(1) clearing point CPIt is higher；
(2) clearing point CPWith fusing point MPBetween difference it is larger, be 53 DEG C；
(3) △ ε and △ n are in range of normal value；
(4) prove that its molecular weight is consistent with the molecular weight that compound e should possess according to MS, according to core
Magnetic spectrum elucidation demonstrates the compound for preparing and is the compound shown in structural formula e.
The two of the particular compound of synthesis are as shown in formula j：
Its synthetic route is：
Concrete synthesis step includes：
Step 1：
(compound h) synthesizes 3- (the bromo- phenyl of 4-) -8- methyl -8- aza-bicyclos [3.2.1] octyl- 3- alcohol.
47.2g (0.2mol, 1eq) paradibromobenzene, 300mL tetrahydrofurans are added in 1L there-necked flasks, is opened
Stirring is opened, -75 DEG C are cooled under nitrogen protection, then Deca 0.22mol (1.1eq) butyl lithium, drop finishes protects
- 75 DEG C～-70 DEG C stirring half an hour are held, then Deca 33.4g (0.24mol, 1.2eq) tropinone and 50mL
The mixed solution of tetrahydrofuran, drop warm naturally to -40 DEG C after finishing, and are incubated half an hour.Reactant liquor is poured into
Hydrolyze in the mixed liquor of 200g frozen water and 0.5mol hydrochloric acid, stirring divided liquid after 15 minutes, took upper organic phase,
With 100mL ethyl acetate to aqueous extraction twice, merge organic faciess.With 300mL deionizations moisture 3
Secondary washing organic faciess, after anhydrous sodium sulfate drying, vacuum distillation removes solvent, obtains 50.3g compound h,
GC detection level 92.0%, yield 85.2%.
Step 2：
(compound i) synthesizes 3- (the bromo- phenyl of 4-) -8- methyl -8- aza-bicyclos [3.2.1] octanes.
Compound h, 300mL obtained in 50g (0.17mol, 1.0eq) step 1 is added in 1L there-necked flasks
Dichloromethane, starts stirring, Deca 19.7g (0.17mol, 1.0eq) triethyl group silicon after being cooled to -75 DEG C
Alkane, drop finish after Deca 24.2g boron trifluoride diethyl etherate again, drop finishes and keeps -75 DEG C～-70 DEG C stirring reactions half little
When, -30 DEG C are then heated to, the hydrolysis of 200mL saturated sodium bicarbonate aqueous solutions are added, is stirred 10 minutes,
Stand a point liquid；Water mutually uses 50mL dichloromethane extraction twice, merges organic faciess, during organic faciess are washed to
Property, after crossing silicagel column at ambient pressure, concentration is dry, uses dehydrated alcohol recrystallization, obtains white solid 34.7g, i.e.,
For compound i, GC detection level 98.5%, yield 72.8%.
Step 3：
8- methyl -3- (3,4,5,2'- tetrafluoro terphenyl -4'- bases) -8- aza-bicyclos [3.2.1] octane be (compound j's)
Synthesis.
34g (0.12mol, 1eq) compound i, 32.4g (0.12mol, 1eq) are added in 1L there-necked flasks
Tri- fluoro- 3- fluorine biphenylboronic acid of 3', 4', 5'-, 19.1g (0.18mol, 1.5eq) sodium carbonate, 1g tetra- (triphenylphosphine)
Palladium (catalyst), 100mL toluene (solvent), 100mL ethanol, 100mL water, are heated to reflux anti-
Answer 8 hours, then pour reactant liquor in separatory funnel stratification, water layer extracts two with 50mL toluene
Time, combining methylbenzene phase is washed twice with 100mL.Toluene is evaporated, with petroleum ether recrystallization three times, is obtained
To white crystal 35.7g, as target product compound j, GC detects its purity for 99.8%, and yield is
69.2%.
The design parameter of compound j of the applicant to synthesizing is determined, and measurement result is as follows：
MP：96℃；
CP：129℃；
△ε：13.3；
△n：0.25；
MS：124.11 (0.8%), 406.18 (2.5%), 425.18 (100.0%), 426.18 (29.3%), 427.18
(4.1%)；
Fig. 2 shows the nuclear magnetic spectrogram of the compound, and the spectrogram is resolved to：1H NMR(400MHz,
d6-DMSO)：δ 7.76 (s, 1H), 7.53 (s, 1H), 7.35 (dd, J=25.0,15.0Hz, 7H), 7.14
- 6.97 (m, 3H), 6.82 (d, J=11.2Hz, 2H), 6.37 (s, 1H), 2.90 (s, 3H), 2.58 (s, 6H),
2.08 (s, 4H), 1.90 (d, J=88.9Hz, 6H), 1.34 (d, J=71.0Hz, 6H).
According to said determination result, it can be seen that：
(1) clearing point CPIt is higher；
(2) clearing point CPWith fusing point CPBetween difference it is larger；
(3) △ ε and △ n are in range of normal value；
(4) prove that its molecular weight is consistent with the molecular weight that compound e should possess according to MS, according to nuclear-magnetism
Spectrum elucidation demonstrates the compound for preparing and is the compound shown in structural formula e.
According to a further aspect in the invention, there is provided a kind of liquid-crystal composition, the liquid-crystal composition at least include
A kind of compound of the present invention.
According to the liquid-crystal composition of one embodiment of the present invention, the liquid-crystal composition is included with percentage by weight
The compound of the invention of meter 5-40%.
According to the liquid-crystal composition of one embodiment of the present invention, the liquid-crystal composition is included with percentage by weight
The compound of the invention of meter 15-30%.
Liquid-crystal composition of the invention, not only with appropriate optical anisotropy, low rotary viscosity and
Response speed faster, and there is high clearing point, can be applied not only in liquid crystal display, and the liquid
Crystal display can be used at high temperature, and the temperature range that can be used is wider.
According to a further aspect in the invention, there is provided a kind of liquid crystal display, containing liquid crystal of the invention
Compositionss.
Liquid crystal display of the invention, used the present invention compound group into liquid-crystal composition, by
Possess higher clearing point in compound of the invention, have the liquid-crystal composition containing the compound
Higher clearing point, when the liquid-crystal composition is applied in liquid crystal display, the liquid crystal display can be
Work under hot conditionss；Difference between the clearing point and fusing point of the compounds of this invention is larger, is less than in temperature
During fusing point, compound is solid-state, and when temperature is more than clearing point, compound is liquid, only in fusing point and
Between clearing point, compound could be present with liquid crystal state, thus increase compound clearing point and
Difference between fusing point, also increases the difference between the clearing point of liquid-crystal composition and fusing point, therefore increases
The operating temperature range of the big liquid crystal display using the liquid-crystal composition.
In summary it can be seen, the optional factor of compound of the invention, liquid-crystal composition and liquid crystal display
It is more, different embodiments can be combined into using the claim of the present invention, therefore embodiment is only to this
The explanation of invention, and not as limitation of the present invention.
The present invention is said below in conjunction with the embodiment with regard to liquid-crystal composition and corresponding comparative example
It is bright.Wherein, embodiment 1-6 is compositionss of the invention, and comparative example 1～6 is and does not accordingly contain
In the compositionss of the compound of the with good grounds present invention, wherein embodiment and comparative example, monomer component is weight
Part；And respectively the relevant parameter of corresponding embodiment and the liquid-crystal composition in comparative example is determined, have
Volume data is referring to following embodiments and comparative example.
Embodiment 1 and comparative example 1：
The component of the liquid-crystal composition of embodiment 1 and comparative example 1 is as shown in table 1：
Table 1
A series of performance test, test result have been carried out to the liquid-crystal composition of embodiment 1 and comparative example 1
As shown in table 1-1：
Table 1-1
| Performance parameter | Embodiment 1 | Comparative example 1 |
| Cp | 92℃ | 85℃ |
| Δn | 0.189 | 0.109 |
| Δε | 7.6 | 7.8 |
| γ1 | 73 | 75 |
Can be seen that according to the test result of table 1-1：This is added in liquid-crystal composition in embodiment 1
The compound of invention, which significantly improves liquid crystal combination compared with the comparative example 1 for not adding the compounds of this invention
The clearing point (Cp) of thing, the fusing point of liquid-crystal composition typically below -10 DEG C, comparative example 1 and embodiment
In 1, the fusing point of liquid-crystal composition is sufficiently low, is completely below the temperature range for normally using, so fusing point pair
Affect little using temperature, therefore improve the operating temperature range that clearing point improves liquid-crystal composition；
It is possible to additionally incorporate the compound of the present invention, the rotary viscosity (γ 1) and dielectric constant (Δ ε) to liquid-crystal composition
Impact less, therefore liquid-crystal composition can be made to keep normal use.The chemical combination for adding in embodiment 1
Thing and other monomers interact and also add optical anisotropy (the Δ n), therefore help of liquid-crystal composition
In thickness of liquid crystal layer is reduced to reduce thickness of liquid crystal box, so as to further reduce the thickness of liquid crystal display.
Embodiment 2 and comparative example 2
The component of the liquid-crystal composition of embodiment 2 and comparative example 2 is as shown in table 2：
Table 2
A series of performance test, test result have been carried out to the liquid-crystal composition of embodiment 2 and comparative example 2
As shown in table 2-2：
Table 2-2
| Performance parameter | Embodiment 2 | Comparative example 2 |
| Cp | 92℃ | 85℃ |
| Δn | 0.179 | 0.182 |
| Δε | 7.9 | 7.8 |
| γ1 | 96 | 94 |
Can be seen that according to the test result of table 2-2：The compound of the present invention is added in embodiment 2, with
Do not add the comparative example 2 of the compounds of this invention to compare, improve the clearing point (Cp) of liquid-crystal composition, liquid
The fusing point of crystal composite typically below -10 DEG C, the fusing point of liquid-crystal composition in comparative example 2 and embodiment 2
It is sufficiently low, the temperature range for normally using is completely below, so fusing point is on affecting little using temperature, because
This improves clearing point, that is, improve the operating temperature range of liquid-crystal composition；The optics of liquid-crystal composition is each
Anisotropy (Δ n), dielectric anisotropy (Δ ε) and rotary viscosity (γ1) change is less；Therefore basis
The liquid-crystal composition of the present embodiment improves clearing point (Cp) but does not affect other parameters performance.
Embodiment 3 and comparative example 3
The component of the liquid-crystal composition of embodiment 3 and comparative example 3 is as shown in table 3：
Table 3
A series of performance test, test result have been carried out to the liquid-crystal composition of embodiment 3 and comparative example 3
As shown in table 3-3：
Table 3-3
| Performance parameter | Embodiment 3 | Comparative example 3 |
| Cp | 85℃ | 80℃ |
| Δn | 0.179 | 0.182 |
| Δε | 9.6 | 7.8 |
| γ1 | 160 | 96 |
Can be seen that according to the test result of table 3-3：The compound of the present invention is added in embodiment 3, with
Do not add the comparative example 3 of the compounds of this invention to compare, improve the clearing point (Cp) of liquid-crystal composition, liquid
The fusing point of crystal composite typically below -10 DEG C, the fusing point of liquid-crystal composition in comparative example 3 and embodiment 3
It is sufficiently low, the temperature range for normally using is completely below, so fusing point is on affecting little using temperature, because
This improves clearing point, that is, improve the operating temperature range of liquid-crystal composition；The optics of liquid-crystal composition is each
(Δ n) changes are little for anisotropy；Improve dielectric anisotropy (Δ ε) therefore when which is applied to liquid crystal display
The response speed of liquid crystal display can be improved during device；While rotary viscosity (γ1) increase, but still
In normal use range, and dielectric anisotropy (Δ ε) and rotary viscosity (γ1) to display
In the impact of response speed, dielectric anisotropy (Δ ε) is occupied an leading position, therefore in general, will implement
When the compositionss of example 3 are applied to liquid crystal display, the response speed of liquid crystal display is still improve.
Embodiment 4 and comparative example 4
The component of the liquid-crystal composition of embodiment 4 and comparative example 4 is as shown in table 4：
Table 4
A series of performance test, test result have been carried out to the liquid-crystal composition of embodiment 4 and comparative example 4
As shown in table 4-4：
Table 4-4
| Performance parameter | Embodiment 4 | Comparative example 4 |
| Cp | 95℃ | 85.0℃ |
| Δn | 0.110 | 0.109 |
| Δε | 7.4 | 7.8 |
| γ1 | 72 | 75 |
Can be seen that according to the test result of table 4-4：The compound of the present invention is added in embodiment 4, with
Do not add the comparative example 4 of the compounds of this invention to compare, improve the clearing point of liquid-crystal composition, liquid crystal combination
, typically below -10 DEG C, in comparative example 4 and embodiment 4, the fusing point of liquid-crystal composition is enough for the fusing point of thing
It is low, the temperature range for normally using is completely below, so fusing point is on affecting little using temperature, therefore is improved
Clearing point, that is, improve the operating temperature range of liquid-crystal composition；The optical anisotropy of liquid-crystal composition
(Δ n), dielectric anisotropy (Δ ε) and rotary viscosity (γ1) change is less.It can be seen that
The clearing point of liquid-crystal composition can be improved after the compound for adding the present invention, but does not affect other performances
Parameter.
Embodiment 5 and comparative example 5
The component of the liquid-crystal composition of embodiment 5 and comparative example 5 is as shown in table 5：
Table 5
A series of performance test, test result have been carried out to the liquid-crystal composition of embodiment 5 and comparative example 5
As shown in table 5-5：
Table 5-5
| Performance parameter | Embodiment 5 | Comparative example 5 |
| Cp | 84℃ | 75.3℃ |
| Δn | 0.182 | 0.171 |
| Δε | 9.2 | 7.8 |
| γ1 | 111 | 75 |
Can be seen that according to the test result of table 5-5：The compound of the present invention is added in embodiment 5, with
Do not add the comparative example 5 of the compounds of this invention to compare, improve the clearing point of liquid-crystal composition, liquid crystal combination
, typically below -10 DEG C, in comparative example 5 and embodiment 5, the fusing point of liquid-crystal composition is enough for the fusing point of thing
It is low, the temperature range for normally using is completely below, so fusing point is on affecting little using temperature, therefore is improved
Clearing point, that is, improve the operating temperature range of liquid-crystal composition；The optical anisotropy of liquid-crystal composition
(Δ n) changes are little；Improve dielectric anisotropy (Δ ε) therefore can when which is applied to liquid crystal display
To improve the response speed of liquid crystal display；While rotary viscosity (γ1) be also improved, but still
In normal operating range, and dielectric anisotropy (Δ ε) and rotary viscosity (γ1) display is being reacted
In the impact of speed, dielectric anisotropy (Δ ε) plays a leading role, therefore in general, by embodiment 5
Compositionss when being applied to liquid crystal display, still improve the response speed of liquid crystal display.
Embodiment 6 and comparative example 6
The component of the liquid-crystal composition of embodiment 6 and comparative example 6 is as shown in table 6：
Table 6
A series of performance test, test result have been carried out to the liquid-crystal composition of embodiment 6 and comparative example 6
As shown in table 6-6：
Table 6-6
| Performance parameter | Embodiment 6 | Comparative example 6 |
| Cp | 92℃ | 86℃ |
| Δn | 0.179 | 0.182 |
| Δε | 7.9 | 7.8 |
| γ1 | 96 | 94 |
Can be seen that according to the test result of table 6-6：The compound of the present invention is added in embodiment 6, with
Do not add the comparative example 6 of the compounds of this invention to compare, improve the clearing point (C of liquid-crystal compositionP), liquid
The fusing point of crystal composite typically below -10 DEG C, the fusing point of liquid-crystal composition in comparative example 6 and embodiment 6
It is sufficiently low, the temperature range for normally using is completely below, so fusing point is on affecting little using temperature, because
This improves clearing point, that is, improve the operating temperature range of liquid-crystal composition；The optics of liquid-crystal composition is each
Anisotropy (Δ n), dielectric anisotropy (Δ ε) and rotary viscosity (γ1) change is less.Therefore can be with
Find out the clearing point that liquid-crystal composition can be improved after the compound for adding the present invention, and while do not affect which
Its performance parameters.
The liquid-crystal composition that embodiment 1-6 is obtained comparative example corresponding thereto is compared, and clearing point is obtained
Improve, meet the demand that liquid crystal display is used at high temperature, while the fusing point of liquid-crystal composition typically exists
Less than -10 DEG C, in comparative example and embodiment, the fusing point of liquid-crystal composition is sufficiently low, and being completely below normally makes
Temperature range, so fusing point is on affecting little using temperature, therefore improves clearing point and improves liquid
The operating temperature range of crystal composite.
Obviously, those skilled in the art can carry out various changes and modification without deviating from this to the present invention
Bright spirit and scope.So, if the present invention these modification and modification belong to the claims in the present invention and
Within the scope of its equivalent technologies, then the present invention is also intended to comprising these changes and modification.
Claims (8)
1. a kind of compound, it is characterised in that the compound is shown in formula I：
Wherein,
R1And R2It is independently selected from the alkyl or alkoxyl of hydrogen atom or 1～15 carbon atom；
A, B and C are each independently selected from following radicals：
Z1And Z2It is each independently selected from：Singly-bound ,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CF2O-、
-OCH2-、-CH2O-、-OCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-C2F4-、-(CH2)4-
With-CF=CF-；
A, b, c, d and e are each independently selected from 0,1 and 2.
2. compound as claimed in claim 1, it is characterised in that in the alkyl or alkoxyl
Individual or multiple-CH2- independently of one another by-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-O- or ring fourth
Alkane is substituted.
3. compound as claimed in claim 1, it is characterised in that in the alkyl or alkoxyl
Or multiple hydrogen are replaced by fluorine and/or chlorine independently of one another.
4. compound as claimed in claim 1, it is characterised in that the alkyl or alkoxyl are each only
On the spot by CN, OCN, OCF3、CHF2、OCHF2, SCN, NCS or SF5Replace.
5. a kind of liquid-crystal composition, it is characterised in that the liquid-crystal composition at least includes a kind of claim
1～4 arbitrary compound.
6. liquid-crystal composition as claimed in claim 5, it is characterised in that the liquid-crystal composition include with
The arbitrary compound of 5-40% Claims 1 to 4 of percentage by weight meter.
7. liquid-crystal composition as claimed in claim 6, it is characterised in that the liquid-crystal composition include with
The arbitrary compound of 15-30% Claims 1 to 4 of percentage by weight meter.
8. a kind of liquid crystal display, it is characterised in that containing the arbitrary liquid crystal combination of claim 5～7
Thing.
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