CN104557545B - Polymerizability compound and the application in optically anisotropic body and liquid crystal display cells thereof - Google Patents
Polymerizability compound and the application in optically anisotropic body and liquid crystal display cells thereof Download PDFInfo
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- CN104557545B CN104557545B CN201310471077.2A CN201310471077A CN104557545B CN 104557545 B CN104557545 B CN 104557545B CN 201310471077 A CN201310471077 A CN 201310471077A CN 104557545 B CN104557545 B CN 104557545B
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- 0 *C(CC1)c(cc2)c1cc2-c(cc1)ccc1-c1ccc(*)cc1 Chemical compound *C(CC1)c(cc2)c1cc2-c(cc1)ccc1-c1ccc(*)cc1 0.000 description 12
- OCWXXJVSUSDIRG-UHFFFAOYSA-N CC(CC1)CCC1C(CC1)CCC1C=O Chemical compound CC(CC1)CCC1C(CC1)CCC1C=O OCWXXJVSUSDIRG-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention relates to the polymerizable compound of formula I.The polymerizable liquid crystal compound of the polymerizable compound that the present invention also provides for comprising the present invention and liquid crystal display cells, especially for PS or PSA(" polymer stabilizing " or " polymer-stabilized alignment ") liquid crystal display cells in the liquid crystal display of type.Polymerizable liquid crystal compound of the present invention has good dissolubility, a more preferable orientation effect, and its rate of polymerization faster, polymerization more completely, residual lower, it is thus possible to improve the problem that display is bad largely.
Description
Technical field
The present invention relates to a kind of polymerizability compound, polymerizability liquid-crystal composition containing this polymerizability compound, with
And the application in optically anisotropic body and polymer stabilized liquid crystal display element, especially " poly-at PS or PSA(
Compound is stable " or " polymer-stabilized alignment ") type liquid crystal display in application.
Background technology
In recent years, along with the fast development of informationized society, more gorgeous, more accurate flat panel display technology, three dimensional display
Technology has been born, and may be used for the optical delay sheet (Retarder) of this kind of liquid crystal display, patterned retardation sheet (Patterned
Retarder), the importance of the optically anisotropic body in lens pillar (Lenticular Lens) etc. improves day by day.For requiring
High-durability, multifunction optically anisotropic body for, in addition to optical characteristics, polymerization speed, dissolubility, molten
The character such as point, vitrification point, the transparency of polymer, mechanical strength, case hardness and thermostability also become evaluation optics
The key factor of anisotropic body.
Prior art uses polymerizable liquid crystal material make optically anisotropic body, but its to have long-time stability bad, resistance to
The problems such as time property is the best.
Polymer stabilized liquid crystal Display Technique is the orientation shape that the additional energy using polymer to provide carrys out stabilizing liquid crystal molecule
State or phase, disclosed technology such as polymer stabilizing type cholesteric phase (PSCT, polymer stabilized Cholesteric
Texture), polymer stabilizing nematic phase (PSNP, polymer stabilized nematic phase), polymer stabilizing blue phase
(PSBP, polymer stabilized blue phase), wherein according to the difference of display pattern, polymer stabilizing nematic phase again may be used
Common to be subdivided into polymer stabilizing vertical orientation (PSVA, polymer stabilized vertical alignment), polymer stabilizing
Face conversion (PSIPS, polymer stabilized in-plane switch), the optical compensation curved arrangement of polymer stabilizing (PSOCB,
Polymer stabilized optically compensated birefringence) etc..Inside the above technology, by solidification
Polymerizable compound formation polymer, to provide the support on mechanics, makes liquid crystal molecule be permanently retained in pre-set work
Make in state, thus considerably improve display effect, such as, faster response speed, higher contrast, broader is provided
Operating temperature range etc..
CN03146257 discloses a kind of for polymer stabilizing vertical orientation (PSVA, polymer stabilized vertical
Alignment) liquid crystal media, it is characterised in that comprise liquid-crystal composition and the polymerizable compound of ad hoc structure, but its
Polymerizable compound is only limited to single reaction compound and two reactive compounds, and polymerization speed is relatively slow, polymerizable after polymerization
The residual quantity of compound is higher, has had a strong impact on the reliability of liquid crystal display.
CN101080480 discloses a kind of for polymer stabilizing blue phase (PSBP, polymer stabilized blue phase)
Mesogenic system, is made up of polymer precursor and lower-molecular-weight component, but its polymer precursor is only limitted to single reaction compound
With two reactive compounds, limited mechanical characteristic can only be provided, cause blue phase temperature range the widest, have impact on blue phase
The practicality of liquid crystal.
Accordingly, there exist for the polymerizable in optically anisotropic body and polymer stabilized liquid crystal display element can be applied
The needs of property compound.
Summary of the invention
The goal of the invention of the present invention is to provide a kind of polymerizability compound and preparation method thereof, and containing this polymerizability
The polymerizability liquid-crystal composition of compound and its answering in optically anisotropic body and polymer stabilized liquid crystal device
With, especially at PS or PSA(" polymer stabilizing " or " polymer-stabilized alignment ") in the liquid crystal display of type
Purposes.
The present invention provides the polymerizable compound of a kind of formula I,
Wherein,
Pa and Pb is identical or different, represents that polymerizable groups, described polymerizable groups select free style B-1 extremely independently of one another
The group of formula B-14 composition:
L1And L2Identical or different, represent hydrogen, F or Cl independently of one another；
r1And r2Identical or different, represent 0,1 or 2 independently of one another.
In some embodiments, described polymerizable groups selects free style B-1 to formula B-5, formula B-13 and formula B-14 group
The group become.
In some embodiments it is preferred that described polymerizable groups is selected from formula B-1 or formula B-2.
In embodiments of the invention, described polymerizable compound is preferably the compound that Formulas I-1 represents to I-6:
And
Wherein,
Pa and Pb is identical or different, represents independently of one another
Compound described in the contained I-2-1 of polymerizable compound of the present invention:
The present invention also provides for a kind of polymerizable liquid crystal compound, and described liquid-crystal composition comprises gathering described at least one formula I
Conjunction property compound.
The present invention also provides for a kind of optically anisotropic body being polymerized by the polymerizable composition, polymerizable composition of the present invention and obtaining, and includes institute
State the liquid crystal display cells of optically anisotropic body.
The present invention also provides for a kind of polymer stabilized liquid crystal display element, the liquid crystal material including being prepared by following methods:
The polymerizable compound of at least one present invention is added in the liquid-crystal composition of non-polymerization；
The polymerization of the described polymerizable compound in described liquid-crystal composition is made to obtain described liquid crystal material.
The present invention also provides for a kind of optically anisotropic body, by comprising the polymerizable composition, polymerizable composition of polymerizable compound described in formula I
Polymer constituted.The manufacture method of this optically anisotropic body comprises:
1) dissolve comprising the polymerizable composition, polymerizable composition of polymerizable compound described in formula I with suitable solvent, be configured to solution.
Solvent be can with single solvent or mixed solvent, boiling point below 220 DEG C, available solvent selected from alkane, halogenated alkane,
Ketone, esters, alcohols, alcohol ethers, aromatic hydrocarbons, ring apoplexy due to endogenous wind one or more, preferred solvent selected from normal hexane, chloroform,
Acetone, 2-butanone, methyl iso-butyl ketone (MIBK), isophorone, ethyl acetate, n-propyl acetate, isopropyl acetate, acetic acid are just
Butyl ester, methanol, ethanol, isopropanol, normal propyl alcohol, ethylene glycol monomethyl ether, glycol dimethyl ether, propylene glycol monomethyl ether, propylene glycol
Dimethyl ether, propylene glycol methyl ether acetate, toluene, dimethylbenzene, hexamethylene, cycloheptane, Ketocyclopentane, Ketohexamethylene, γ-Ding Nei
One or more in ester；
2) this solution is coated on base material, keeps irradiating with ultraviolet light under uniform state of orientation making polymerizable composition, polymerizable composition gather
Close, obtain optically anisotropic body.Described coating method is selected from rotary coating, extrusion coated, scraper for coating, slit painting
One in cloth, extrusion slit coating, silk screen printing, intaglio printing, letterpress, flexographic printing, inkjet printing
Or it is several.Base material can be with both alignment layers, it is also possible to without both alignment layers, and base material can be glass or transparent plastic sheeting.
Ultraviolet ray intensity can be 0.5～200mW/cm2, preferably 5～50mW/cm2。
The present invention also provides for a kind of liquid crystal display cells, and described liquid crystal display cells uses above-mentioned optically anisotropic body.
Polymerizable liquid crystal compound of the present invention is compared to prior art, and it is more preferable that it has good dissolubility, orientation effect,
Faster, polymerization is more complete, remains lower, thus improves the problem that display is bad largely for rate of polymerization.
Accompanying drawing explanation
Fig. 1 is compound I-2-11H NMR schemes.
Detailed description of the invention
Following example are used for illustrating the present invention, but are not limited to the scope of the present invention, and all other is taken off without departing from the present invention
The equivalence completed under the spirit shown changes or modifies, and should be included in the scope of the said claims.
The each liquid-crystal compounds used below in an example, all can be synthesized by known method, or logical
Cross and be either commercially available.These synthetic technologys are conventional, and obtained each liquid-crystal compounds meets electrical type compound after tested
Standard.
Embodiment 1
The synthetic route preparing compound I-2-1 is as follows:
Specifically include the following step:
1) synthesis of compound A
In single port bottle add 4g5-bromindion, 120g DMSO(dimethyl sulfoxide), 5.06g join boric acid pinacol ester, 3.72g
Potassium acetate, 0.28g Pd (dppf) Cl2, under nitrogen protection, back flow reaction 3h.
After reaction terminates, sucking filtration, filtrate is poured in frozen water, again sucking filtration, obtain grey black sticky solid, be dried after dissolving,
Slightly cross pillar, obtain 3.19g solid.Petroleum ether is pulled an oar, and obtains 2.5g compound as white solid A.
2) synthesis of compound B
HPGBr:
It is 50% by 5.67g HPGBr(purity), 2.5g compound A and 50g DME(dimethyl ether) add in there-necked flask,
Stirring and dissolving, is sequentially added into aqueous solution and the 4-3-Pd(tetra-triphenylphosphine palladium of sodium carbonate under nitrogen protection), it is heated to 100 DEG C
Back flow reaction 10h.
After reaction terminates, sucking filtration, use EA(ethyl acetate) filter wash cake, and extract filtrate with EA, and washing, anhydrous
Na2SO4It is dried, is spin-dried for obtaining 5g dark yellow solid.DCM(dichloromethane)/EtOH=5/1 pull an oar 2 times, obtain 1.34g purer
Product compound B.
3) synthesis of compound C
By 2.70g compound B, 50g THF(oxolane) it is sequentially added in single port bottle, ice bath, the first of dropping KBH4
Alcoholic solution.Drip off, go to stirred overnight at room temperature.After reaction terminates, partial solvent is removed in rotation, pours remaining reactant liquor into ice
In water, sucking filtration obtains solid, dissolves with THF, and anhydrous sodium sulfate is dried, and silica gel mixed sample crosses post, obtains 0.65g sterling, big portion
Point product residue on pillar, THF drip washing, obtain 1.93g light yellow solid.
4) synthesis of compound I-2-1
By 0.65g compound C, 0.52g methacrylic acid, 200mL THF, 2 BHT(2,6-di-t-butyls are to toluene
Phenol), 0.05g DMAP(4-dimethylamino naphthyridine) it is sequentially added in single port bottle, ice bath, nitrogen is protected, under ice bath stirring,
It is slowly added dropwise DCC(dicyclohexylcarbodiimide) and 100mL THF mixed liquor.Drip off, go to stirred overnight at room temperature.
After reaction terminates, sucking filtration, DCM filter wash cake, filtrate is spin-dried for, and silica gel mixed sample crosses post 2 times, obtains 0.24g white solid
Compound I-2-1.The 1H NMR figure of compound I-2-1 sees Fig. 1.
Embodiment 2
The polymerizable liquid crystal compound LC-1 of composition shown in modulation formula as below, the liquid-crystal compounds of composition and part by weight are such as
Lower described:
The physical property of above-mentioned liquid-crystal composition is: clearing point Cp=80 DEG C, optical anisotropy Δ n=0.102, dielectric constant respectively to
Opposite sex Δ ε=-3.20.
Add the compound (I-2-1) of embodiment 1 of 0.3% in the liquid-crystal composition LC-1 of 99.7%, uniform dissolution,
Obtaining mixture PLC-1, the physical property of the physical property of PLC-1 and above-mentioned LC-1 is almost without difference.Use priming by vacuum method will
PLC-1 inject gap be 4 μm and there is vertical orientation (Homeotropic alignment) testing cassete in, execute
Adding frequency is 60Hz, and driving voltage is the square wave of 16V, with high-pressure mercury uviol lamp to testing cassete irradiation ultraviolet radiation,
The exposure rate being adjusted to box surface is 30mW/cm2, irradiate 600 seconds, obtain vertically joining after polymer compound polymerization
To liquid crystal display cells, use LCT-5016C liquid crystal electro-optic parameter tester test tilt angle, then decompose testing cassete,
High-efficient liquid phase chromatogram HPLC is used to measure the polymer compound of residual in liquid-crystal composition.Result is summarized in Tables 1 and 2
In.
Comparative example 1
In the liquid-crystal composition LC-1 of the compound R M1 to 99.7% adding 0.3%, uniform dissolution, obtain mixture
PLC-2。
RM1:
The method described in patent documentation CN101418220A is used to synthesize RM1.
The physical property of the physical property of PLC-2 and above-mentioned LC-1 is almost without difference.Use priming by vacuum method that PLC-2 is injected gap
It is that in 4 μm and the testing cassete with vertical orientation (Homeotropic alignment), applying frequency is 60Hz,
Driving voltage is the square wave of 16V, with high-pressure mercury uviol lamp to testing cassete irradiation ultraviolet radiation, is adjusted to the photograph on box surface
Penetrating intensity is 30mW/cm2, irradiate 600 seconds, obtain the liquid crystal display cells of the vertical orientation after polymer compound polymerization,
Use LCT-5016C liquid crystal electro-optic parameter tester test tilt angle, then decompose testing cassete, use high performance liquid chromatography
HPLC measures the polymer compound of residual in liquid-crystal composition.Result is summarized in Tables 1 and 2.
Tilt angle before and after table 1UV
| Proportion of composing | Tilt angle (°) before UV | Tilt angle (°) after UV | |
| PLC-1 | 99.7%LC-1+0.3%(I-2-1) | 89.6 | 83.4 |
| PLC-2 | 99.7%LC-1+0.3%RM1 | 89.4 | 85.3 |
Table 2 polymer residue
| UV polymerization time (s) | PLC-1 polymer residue (%) | PLC-2 polymer residue (%) |
| 0 | 0.30 | 0.30 |
| 120 | 0.24 | 0.25 |
| 180 | 0.16 | 0.21 |
| 240 | 0.10 | 0.17 |
| 300 | 0.07 | 0.13 |
| 360 | 0.05 | 0.13 |
Knowable to the correction data of Tables 1 and 2, the polymerizable compound relative polymerization liquid-crystal compounds RM1 of the present invention
For, the orientation effect formed is more preferable, and faster, polymerization is more complete, remains lower for polymeric rate, thus largely
Improve the problem that display is bad.
Claims (7)
1. a polymerizable compound of formula I,
Wherein,
Pa and Pb is identical or different, represents that polymerizable groups, described polymerizable groups select free style B-1 extremely independently of one another
The group of formula B-2 composition:
L1And L2Identical or different, represent hydrogen, F or Cl independently of one another；
r1And r2Identical or different, represent 0,1 or 2 independently of one another.
Polymerizable compound the most according to claim 1, it is characterised in that the choosing of described polymerizable compound is freely led to
Formulas I-1 to formula I-6 compound form group:
And
Wherein,
Pa and Pb is identical or different, represents independently of one another
Polymerizable compound the most according to claim 2, it is characterised in that the contained I-2-1 of described polymerizable compound
Described compound:
4. comprise the polymerizable composition, polymerizable composition of polymerizable compound according to any one of claims 1 to 3.
5. the optically anisotropic body being polymerized to obtain by polymerizable composition, polymerizable composition as claimed in claim 4.
6. the liquid crystal display cells including optically anisotropic body as claimed in claim 5.
7. a polymer stabilized liquid crystal display element, the liquid crystal material including being prepared by following methods:
At least one polymerism chemical combination as described in any one of claims 1 to 3 is added in the liquid-crystal composition of non-polymerization
Thing；
The polymerization of the described polymerizable compound in described liquid-crystal composition is made to obtain described liquid crystal material.
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| CN105219401B (en) * | 2015-09-07 | 2017-12-08 | 江苏和成新材料有限公司 | Polymerizable liquid crystal mixture and its application |
| CN108727195B (en) * | 2017-04-21 | 2023-10-31 | 江苏和成显示科技有限公司 | Polymerizable compound and application thereof |
| CN109207165A (en) * | 2017-06-30 | 2019-01-15 | 江苏和成显示科技有限公司 | Polymerizable liquid crystal compound and its liquid crystal display device |
| CN108084029B (en) * | 2017-12-20 | 2021-08-31 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and liquid crystal display element |
| CN108070386B (en) * | 2017-12-20 | 2021-05-04 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and liquid crystal display element |
| CN108192642B (en) * | 2018-01-30 | 2021-06-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition and display using same |
| CN110527521A (en) * | 2018-05-23 | 2019-12-03 | 北京八亿时空液晶科技股份有限公司 | A kind of polymerizability compound and the preparation method and application thereof containing indane structural |
| CN116814275B (en) * | 2023-08-30 | 2023-12-12 | 南昌虚拟现实研究院股份有限公司 | Liquid crystal composition and liquid crystal optical element comprising same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1356371A (en) * | 2000-11-13 | 2002-07-03 | 大日本油墨化学工业株式会社 | Polymerized compound, polymerized liquid cryseal composition containing it, and process for preparing anisotropic optical part from said liquid crysted composition |
| CN102911673A (en) * | 2012-10-13 | 2013-02-06 | 江苏和成显示科技股份有限公司 | Liquid crystal composite and electro-optical display device comprising same |
| CN103360257A (en) * | 2009-01-23 | 2013-10-23 | Dic株式会社 | Polymerizable biphenyl compound |
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| JP5493416B2 (en) * | 2009-03-23 | 2014-05-14 | Ｄｉｃ株式会社 | Polymerizable biphenyl compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1356371A (en) * | 2000-11-13 | 2002-07-03 | 大日本油墨化学工业株式会社 | Polymerized compound, polymerized liquid cryseal composition containing it, and process for preparing anisotropic optical part from said liquid crysted composition |
| CN103360257A (en) * | 2009-01-23 | 2013-10-23 | Dic株式会社 | Polymerizable biphenyl compound |
| CN102911673A (en) * | 2012-10-13 | 2013-02-06 | 江苏和成显示科技股份有限公司 | Liquid crystal composite and electro-optical display device comprising same |
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