CN106565487B - A kind of terphenyl compound and the liquid-crystal composition comprising it - Google Patents
A kind of terphenyl compound and the liquid-crystal composition comprising it Download PDFInfo
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- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
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- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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Abstract
The present invention relates to a kind of terphenyl compound and comprising the liquid-crystal composition including it, belong to technical field of liquid crystal display.Terphenyl compound of the invention can be used in IPS display pattern as a kind of polymerizable smooth orientation compound, it can be also used in OCB (Optically compensated bend, optics self compensation bending), VA (Vertical Alignment liquid crystal, homeotropic alignment liquid crystal), TN (Twist Nematic, twisted nematic liquid crystals) etc. display patterns, the light alignment liquid crystal composition of preparation, neither reduce the quality of protoplasm product, the response speed that product can be improved again, improves the contrast of product.
Description
Technical field
The present invention relates to a kind of terphenyl compound and comprising its liquid-crystal composition, belong to technical field of liquid crystal display.
Background technique
FPD is due to its lighting, and low energy consumption, display effect is good, is rapidly developed, and liquid crystal display is aobvious in plate
Occupy leading position in showing, core material of the liquid crystal material as liquid crystal display, in the case where the development of FPD industry drives, fastly
Speed increases, and is increased every year with 10% or more speed, TFT-LCD (Thin Film Transistor-Liquid Crystal
Display, thin film transistor liquid crystal display) it shows as the high-end display pattern in liquid crystal display, account for entire liquid crystal display
95% or more, TFT-LCD display pattern have TN (Twist Nematic, twisted nematic), IPS (In-Plane
Switching, plane conversion), VA (Vertical Alignment liquid crystal vertical arrangement), OCB
(Optically compensated bend, optics self compensation bending), FFS (Fringe Field Switching, novel side
The switching of boundary's electric field) etc. display patterns, TN mode with fast response time, stability is good, formula is simple and first develops, but this
TN liquid crystal technology has some defects, and most important one is exactly when applying voltage, and liquid crystal molecule will be distorted to 90 degree and could be hidden
Be in the light, but virtually completely realize and be vertically not easy to completely, thus full black state relatively difficult to achieve, also thus contrast compared with
It is low；In addition Liquid Crystal Molecules Alignment mode, so that visible angle is lower.It is not able to satisfy the demand to visual angle and display resolution, mesh
Follow-on liquid crystal technology of preceding mainstream includes VA and two kinds of IPS, and IPS is realized fast using horizontally arranged liquid crystal molecule is rotated
Door movement fundamentally avoids liquid crystal from vertically to the spinning movement of tilt angle, therefore visible angle is IPS intrinsic most
Big advantage；VA is then that liquid crystal is exactly plumbness (opaque, completely black) under unpowered state, and it is excellent to bring inborn contrast
Gesture, and the tilt angle of improvement liquid crystal molecule has also reached the visible angle close to IPS later.The feature of IPS panel maximum
Be exactly it the two poles of the earth all on the same face, change the arrangement mode of liquid crystal molecule particle, using level conversion technology, dynamic
Clearly super steady, environmental protection and energy saving, big visible angle, color color are true to nature for picture, and picture reduction is true etc., especially in image quality side
Face is remarkably than other display panels.Response time is the place that IPS panel is uniquely not so good as TN panel, handle in the present invention
Polymerizable smooth orientation compound is added in IPS liquid-crystal composition, on the basis of not influencing product display performance, hence it is evident that improve
The response speed and contrast of IPS liquid crystal compensate for the disadvantage that IPS liquid crystal response speed is slow, contrast is low.
Summary of the invention
The present invention provides a kind of terphenyl compound and packet for deficiency existing in terms of existing IPS panel response time
Containing its liquid-crystal composition.
The technical scheme to solve the above technical problems is that
A kind of terphenyl compound, which is characterized in that its general structure is as follows:
Wherein, X1, X2, X3Expression O, OC (O) independently, one of 0 or singly-bound C (O)；Sp1,Sp2,Sp3Respectively
Independent expression singly-bound ,-(CH2)n-,-(CH2)n-O-,-(CH2) n-OCO- or-(CH2) one of n-OCOO-, wherein n
For 1 to 12 integer；P1,P2,P3Expression group acrylic acid independently, methyl acrylate, one of oxetanes；L
For it is non-can poly- group, indicate one of the linear or branched alkyl groups of F, Cl, 1-25 carbon atoms, alkoxy, alkenyl, t 0
Or 1.
Further, structural formula is as follows:
The wherein integer that p is 0~12.
Further, structural formula is as follows:
The synthetic route of terphenyl compound of the invention is as follows:
Using terphenyl as core, in the case where DMAP (4- (N, TMSDMA N dimethylamine base) pyridine) is the alkaline environment of solvent, corresponding acid
Or the derivative of acid carries out esterification or etherification reaction, preparation contains the light orientation compound of polymerizable group.Select meta position enterprising
The substitution reaction of row group needs strict control reaction condition and catalyst in the synthesis process, reduces the life of by-product to the greatest extent
At on the one hand the quality of guarantee product, on the other hand improves the yield of product.When group is replaced, because being had in group
Polymerizable group, needs certain safeguard measure, and reaction condition needs strict control.With can poly- base macromolecular compound pure
Also there is comparable difficulty when change, individual compound molecule is poor to light and heat stability, improves purity and separation impurity cannot
Using usual way, in separation impurity and in terms of improving purity, using the method for being protected from light molecular distillation, quality side is being improved
Face selects compound adsorbent to carry out column chromatography, and double solvents is recrystallized, and reaches the quality of product needs.HPLC purity >
99.5%, resistivity is greater than 1E+12 Ω .cm.
The beneficial effects of the present invention are:
Terphenyl compound of the invention can be used in IPS display pattern as a kind of polymerizable smooth orientation compound, can also
Used in OCB (Optically compensated bend, optics self compensation bending), VA (Vertical Alignment
Liquid crystal, homeotropic alignment liquid crystal), the display patterns such as TN (Twist Nematic, twisted nematic liquid crystals), preparation
Light alignment liquid crystal composition, neither reduce the quality of protoplasm product, and the response speed of product can be improved, improve pair of product
Degree of ratio.
The liquid-crystal composition comprising above-mentioned terphenyl compound is also claimed in the present invention.
Further, the additive amount of the terphenyl compound is 0.05~3wt% of other components total weight.
Further, the liquid-crystal composition further includes the compound as described in general formula I~VI:
Wherein, the integer that n, m are 1-20；X, y are 0 or 1；Y is F ,-OCF3,-CF3,-OCHF2, OCH2F, straight chain alcoxyl
One of base group；[A]-is phenylene or cyclohexylidene；Z is-CH2CH2,-CH2O- or singly-bound；Q is in 0,1,2,3
Any one；
The ratio of each component is as follows in above-mentioned composition: score meter by weight, one or more chemical combination with general formula I
Object: 8~48wt%；One or more compounds with general formula II: 12~50wt%；One or more changes with general formula III
Close object: 0~25wt%；One or more compounds with general formulae IV: 7~19wt%；It is one or more with general formula V
Compound: 0~13wt%；One or more compounds with general formula VI: 6~29wt%.
Further, the structural formula of compound with general formula I are as follows:
Further, the compound with general formula II are as follows:
Further, the compound with general formula III are as follows:
Further, the compound with general formulae IV are as follows:
Further, the structural formula of compound with general formula V are as follows:
Further, the structural formula of compound with general formula VI are as follows:
The beneficial effect of liquid-crystal composition provided by the invention is:
1) use temperature range is wide (- 40 DEG C --- 90 DEG C), has high clearing point (110 DEG C), ultralow S-N point (- 50 DEG C),
Ranges of indices of refraction is wide (0.100-0.125), the wide 1.25V-3.00V of voltage range；
2) this liquid-crystal composition stability is high, displays contrast height, adapts to the need of the ultralow superhigh temperature variation of automotive environment
It asks.
The terphenyl compound is also claimed and comprising its liquid-crystal composition in liquid crystal display systems in the present invention
Application.
Specific embodiment
Principles and features of the present invention are described below in conjunction with example, the given examples are served only to explain the present invention, and
It is non-to be used to limit the scope of the invention.
One, the synthesis of terphenyl compound
1,1 ', 1 " 27.8 grams of trihydroxy terphenyl compound (0.1mol), 41.2 grams of phosphorus trichloride (0.3mol), DMAP
(4-dimethylaminopyridine) 200ml, 30.0 grams of acrylic acid (0.42mol), 1% polymerization inhibitor MTBHQ is added, and (2- tert-butyl is to benzene
Diphenol) 0.17 gram, stirring slowly heats up, and when temperature arrives 50--55 DEG C, reaction 1.5 hours continues to be heated to flow back, separates water
Point, reaction no moisture generates reaction terminating, and normal pressure steams excessive acrylic acid, and product is dissolved by heating with toluene, filtering, filtrate by
Gradually decrease temperature crystalline, obtains three acrylic acid terphenyl ester of product, and product is obtained by the purifying of the methods of column chromatography, vacuum distillation, recrystallization
To 16.7 grams, product yield 37.9%.HPLC purity is 99.5%, and resistivity is greater than 1E+12 Ω .cm.
Embodiment 2:
Product:
1,1 ', 1 " -27.8 grams of trihydroxy terphenyl compound (0.1mol), 50.65 grams of dibromo triphenylphosphine
(0.12mol), methylene chloride 100ml, is added in there-necked flask, is heated to flowing back while stirring, and reaction, it is anti-that TLC detects raw material
It should finish, steam solvent, petroleum ether is added in acetonitrile dissolution, filtering, the solid was filtered I crude product of object, 1,1 ', 1 "-tribromo terphenyl
28.6 grams, yield 61.2%.4.45 grams of magnesium chips, with the dried TFT50ml of sodium, a small amount of crude product I, a small amount of iodine, 35 DEG C -- 40
DEG C initiation reaction is added dropwise into reaction mixture while stirring with the crude product I of 150ml dried THF dilution remainder,
It maintains the reflux for, TLC is detected after completion of the reaction, and dilute hydrochloric acid hydrolysis, filtering crystallizes to obtain II crude product, 1,1 ', 1 "-bromoform terphenyl
15.06g yield 48.5%.15.06 grams and 3.5 grams (0.093mol) sodium borohydride solids of upper step product are added to there-necked flask
In, DMF (dimethylformamide) 200ml is added, is heated to 50--60 DEG C while stirring, 18 hours of insulation reaction, TLC is examined
It surveys, no raw material steams solvent, recrystallizes, obtains 1,1 ', 1 "-three III 6.51 grams of methanol terphenyl product, yield 68.7%.1,
1 ', 1 "-three 6.51 grams of methanol terphenyl (0.0203mol), 4.53 grams of acrylic acid (0.063mol), 1% polymerization inhibitor MTBHQ
0.035 gram, DMAP 100ml is heated to flowing back while stirring, maintains the reflux for 3 hours, separates moisture, continues the 1 hour nothing that flows back
Moisture generates, and in reflux 0.5 hour, reaction terminated, and adds water, and organic phase is collected in liquid separation, and concentration steams solvent, crosses alchlor
Column recrystallizes to obtain 8.97 grams of trimethylene phenyl ester of three acrylic acid of product connection, yield 91.6%, HPLC purity 99.61%, resistivity
Greater than 1E+12 Ω .cm.
Embodiment 3:
Product:
1,1 ', 1 " -27.8 grams of trihydroxy terphenyl compound (0.1mol), 21.96 grams of sodium tetrafluoroborate (0.2mol),
0.31 gram, acetic acid 20ml, carbon tetrachloride 150ml of 6 ether of phendioxin 8- crown- is passed through argon gas in the reaction, heats while stirring, instead
Answer temperature control 45 --- it 50 DEG C, reacts 2 hours, stops reaction, sampling washing, isopropanol is added in layering, and filtering is tied again
Crystalline substance obtains 2,6- bis- fluoro- 1,1 ', 1 " -10.7 grams of trihydroxy terphenyl compound, yield 33.8%.Methylene chloride is added
110ml, DMAP 20ml, 15.3 grams of phosphorus trichloride (0.11mol), heating reflux reaction 6 hours, TLC detected fully reacting, drop
To room temperature, organic phase is collected in water on the rocks, 0 DEG C of liquid separation, is added anhydrous magnesium sulfate dry, is transferred in three mouthfuls of reactors, propylene is added
8.04 grams (0.11mol) of acid, is added DMAP30ml, is heated to flowing back while stirring by 0.1 gram of 1%MTBHQ polymerization inhibitor, TLC detection
Fully reacting was in heat preservation 0.5 hour, cooling, concentration removal solvent and unreacted acrylic acid, obtained product 2,6- bis- fluoro- 1,1 ',
1 "-acrylic acid terphenyl ester, by purification process such as column chromatography, recrystallization, vacuum distillation, recrystallizations, obtaining HPLC purity is
99.63%, resistivity is 13.45 grams of 2.1E+12 Ω .cm product, this step yield is 83.2%.
Two, liquid-crystal composition
The code for the group being related in embodiment is illustrated first:
V--- represents alkenylF----- representative-F substituent group
E--- represents ethylene group-CH2CH2- M---- represents methylene oxygroup-CH2O-n--- represents end group alkyl
H---- represents bis- substituted cyclohexyl of 1,4-
B---- represents 1,4- di-substituted-phenyl
U----- represents difluoro-methoxy diphenyl
P------ represents difluoro-methoxy cyclohexyl phenyl
The used test equipment of the resulting test data of embodiment are as follows: liquid chromatograph LC-20A, megger 6517B, it is comprehensive
Light combination electric tester LCT-5016, dielectrometer are Agilent 4284A, clearing point tester WPX-1, birefringent test
The test of instrument DR-M2, S-N point is plum Teller DSC tester, and testing cassete is IPS liquid crystal cell, box thickness step-by-step path difference 300nm.
Embodiment 4:
The formula of liquid-crystal composition is as shown in the table:
| Serial number | Compound | Proportion |
| 1 | 3HHV | 24 |
| 2 | 1HHV1 | 7 |
| 3 | B(2F)HHV | 7 |
| 4 | 1BHHV | 10 |
| 5 | 1BHH3V | 15 |
| 6 | 3HHB(3F) | 4 |
| 7 | 3HB(F)B(3F) | 8 |
| 8 | 3HBB(3F) | 7 |
| 9 | 3B(F,F)UF | 8 |
| 10 | 3BB(F)B(3F) | 4 |
| 11 | 3HHB(F)B(3F) | 6 |
| It is total | 100 |
The liquid-crystal composition test data of above-mentioned formula is as follows:
A certain amount of 1 resulting product of embodiment is added into above-mentioned liquid-crystal composition, with additive amount it is different its
Specific test data is as follows:
Embodiment 5:
The formula of liquid-crystal composition is as shown in the table:
| Serial number | Compound | Proportion |
| 1 | 3HHV | 45 |
| 2 | 1HH1V | 5 |
| 3 | 1BHHV | 7 |
| 4 | 1BHH3V | 12 |
| 5 | B(2F)HHV | 7 |
| 6 | 3HHUF | 8 |
| 7 | 5HHUOCF3 | 10 |
| 8 | 3HHB(2F) | 6 |
| It is total | 100 |
The liquid-crystal composition test data of above-mentioned formula is as follows:
A certain amount of 2 resulting product of embodiment is added into above-mentioned liquid-crystal composition, with additive amount it is different its
Specific test data is as follows:
Embodiment 6:
The formula of liquid-crystal composition is as follows:
| Serial number | Compound | Proportion |
| 1 | 3HHV | 12 |
| 2 | 3HHEB(3F) | 7 |
| 3 | 5HHMB(2F)OCF3 | 5 |
| 4 | 3B(F,F)UF | 8 |
| 5 | 4BB(F)(F,F)UF | 13 |
| 6 | 3BB(F)B2 | 5 |
| 7 | B(3F)HHV | 15 |
| 8 | 2BB(F)B3 | 8 |
| 9 | 3BB(F)(F,F)UF | 10 |
| 10 | 2B(F,F)UF | 7 |
| 11 | 3B(F,F)UF | 10 |
| It is total | 100 |
The liquid-crystal composition test data of above-mentioned formula is as follows:
A certain amount of 3 resulting product of embodiment is added into above-mentioned liquid-crystal composition, with additive amount it is different its
Specific test data is as follows:
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and
Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (7)
1. a kind of liquid-crystal composition, which is characterized in that including the compound as described in general formula I~VI:
Wherein, the integer that n, m are 1-20；X, y are 0 or 1；Y is F ,-OCF3,-CF3,-OCHF2, OCH2F, unbranched alkoxy group
One of；[A]-is phenylene or cyclohexylidene；Z is-CH2CH2,-CH2O- or singly-bound；Q is any one in 0,1,2,3
It is a；
The ratio of each component is as follows in above-mentioned composition: score meter by weight, one or more compounds with general formula I: 8~
48wt%；One or more compounds with general formula II: 12~50wt%；One or more compounds with general formula III: 0
~25wt%；One or more compounds with general formulae IV: 7~19wt%；One or more compounds with general formula V:
0~13wt%；One or more compounds with general formula VI: 6~29wt%；
It further include terphenyl compound in the liquid-crystal composition, the additive amount of the terphenyl compound is other components gross weight
0.05~3wt% of amount, general structure are as follows:
Wherein, X1, X2, X3Expression O, OC (O) independently, one of 0 or singly-bound C (O)；Sp1,Sp2,Sp3Independently
Expression singly-bound ,-(CH2)n-,-(CH2)n-O-,-(CH2) n-OCO- or-(CH2One of) n-OCOO-, wherein n is 1
To 12 integer；P1,P2,P3Expression group acrylic acid independently, methyl acrylate, one of oxetanes；L is
It is non-can poly- group, indicate one of the linear or branched alkyl groups of F, Cl, 1-25 carbon atoms, alkoxy, alkenyl, t be 0 or
1。
2. a kind of liquid-crystal composition, which is characterized in that including the compound as described in general formula I~VI:
Wherein, the integer that n, m are 1-20；X, y are 0 or 1；Y is F ,-OCF3,-CF3,-OCHF2, OCH2F, unbranched alkoxy group
One of；[A]-is phenylene or cyclohexylidene；Z is-CH2CH2,-CH2O- or singly-bound；Q is any one in 0,1,2,3
It is a；
The ratio of each component is as follows in above-mentioned composition: score meter by weight, one or more compounds with general formula I: 8~
48wt%；One or more compounds with general formula II: 12~50wt%；One or more compounds with general formula III: 0
~25wt%；One or more compounds with general formulae IV: 7~19wt%；One or more compounds with general formula V:
0~13wt%；One or more compounds with general formula VI: 6~29wt%；
It further include terphenyl compound in the liquid-crystal composition, the additive amount of the terphenyl compound is other components gross weight
0.05~3wt% of amount, the structural formula of the terphenyl compound are as follows:
The wherein integer that p is 0~12.
3. a kind of liquid-crystal composition, which is characterized in that including the compound as described in general formula I~VI:
Wherein, the integer that n, m are 1-20；X, y are 0 or 1；Y is F ,-OCF3,-CF3,-OCHF2, OCH2F, unbranched alkoxy group
One of；[A]-is phenylene or cyclohexylidene；Z is-CH2CH2,-CH2O- or singly-bound；Q is any one in 0,1,2,3
It is a；
The ratio of each component is as follows in above-mentioned composition: score meter by weight, one or more compounds with general formula I: 8~
48wt%；One or more compounds with general formula II: 12~50wt%；One or more compounds with general formula III: 0
~25wt%；One or more compounds with general formulae IV: 7~19wt%；One or more compounds with general formula V:
0~13wt%；One or more compounds with general formula VI: 6~29wt%；
It further include terphenyl compound in the liquid-crystal composition, the additive amount of the terphenyl compound is other components gross weight
0.05~3wt% of amount, the structural formula of the terphenyl compound are as follows:
4. liquid-crystal composition described in any one of claim 1 to 3, which is characterized in that the chemical combination with general formula I
Object structural formula are as follows:
5. liquid-crystal composition described in any one of claim 1 to 3, which is characterized in that the change with general formulae IV
Close object are as follows:
6. liquid-crystal composition described in any one of claim 1 to 3, which is characterized in that the change with general formula VI
Close object structural formula are as follows:
7. application of the liquid-crystal composition according to any one of claims 1 to 6 in liquid crystal display systems.
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| CN109593040B (en) * | 2017-09-30 | 2023-03-07 | 石家庄诚志永华显示材料有限公司 | Polymerizable compound containing propenyl tetrapolymerized group and composition comprising the same |
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| CN103305231A (en) * | 2013-06-13 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composite containing difluorooxymethylene bridge polar monomer compound |
| CN105238416A (en) * | 2015-10-10 | 2016-01-13 | 烟台显华化工科技有限公司 | Production method of high-purity electronic materials |
| CN105315157A (en) * | 2014-07-30 | 2016-02-10 | 默克专利股份有限公司 | Polymerisable compounds and use thereof in liquid-crystal displays |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103305231A (en) * | 2013-06-13 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composite containing difluorooxymethylene bridge polar monomer compound |
| CN105315157A (en) * | 2014-07-30 | 2016-02-10 | 默克专利股份有限公司 | Polymerisable compounds and use thereof in liquid-crystal displays |
| CN105238416A (en) * | 2015-10-10 | 2016-01-13 | 烟台显华化工科技有限公司 | Production method of high-purity electronic materials |
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