CN105219401B - Polymerizable liquid crystal mixture and its application - Google Patents
Polymerizable liquid crystal mixture and its application Download PDFInfo
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- CN105219401B CN105219401B CN201510564198.0A CN201510564198A CN105219401B CN 105219401 B CN105219401 B CN 105219401B CN 201510564198 A CN201510564198 A CN 201510564198A CN 105219401 B CN105219401 B CN 105219401B
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- 0 CC(C)(C)C1=CC(*)C(*)=C(C(C)(C)c2c(*)c(*)*(C)c(*)*2)C(*)=C1C Chemical compound CC(C)(C)C1=CC(*)C(*)=C(C(C)(C)c2c(*)c(*)*(C)c(*)*2)C(*)=C1C 0.000 description 2
- DYMKGQRODFWYQX-UHFFFAOYSA-N COC(C(N)=C)=O Chemical compound COC(C(N)=C)=O DYMKGQRODFWYQX-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention provides a kind of polymerizable liquid crystal composition, including：The polymerisable liquid crystal compound with cinnamic acid structure shown at least one formula I, and the polymerisable liquid crystal compound shown at least one formula II, the polymerisable liquid crystal compound has good stability, and in situ in the case where being not added with initiator can progressively it polymerize, the good photo orientated film of stability is obtained, the polymerisable liquid crystal compound can be used for light orientation field.
Description
Technical field
A kind of application the present invention relates to polymerizable liquid crystal compound and its in optical field.
Background technology
Liquid crystal molecule is uniformly directed the prerequisite that arrangement is liquid crystal display device (LCD).LCD oriented material should
Meet claimed below：(1) there is good orientation effect to liquid crystal；(2) processing characteristics is good, is formed in substrate surface uniform thin
Film；(3) do not chemically reacted with liquid crystal molecule；(4) it is big with base material adhesive force, it is not likely to produce pin hole；(5) there is hydrophobicity.
The orientation technology industrially used has two major classes, and one kind is traditional friction orientation technology, because technique is simple, quilt
It is widely used.One kind is the non-model control orientation technology to grow up this year, especially photo orientated technology, to overcome friction orientation
Technology easily produce chip cut, can only single and planar orientation the shortcomings that.
Photo orientated technology, two classes can be divided into according to processing procedure difference：One kind is compound system, it is not necessary to is located in advance on surface
Reason, the liquid crystal layer directly with light orientation mixed with photosensitive high molecular；Another kind of is non-compound system, and polymer is pre-processed with polarised light
Substrate, then liquid crystal molecule is aligned on substrate, this is to use more method at present.
Photo orientated technology, according to the difference of oriented material, it is divided into again：
(1) light heterogeneous：Polymer containing the photic cis-trans isomerism group such as azo group or talan.This kind of polymer
Under action of ultraviolet light, change of configuration can occur, so as to produce anisotropy, trigger liquid crystal molecule to be orientated on its surface and arrange
Row.
By taking azobenzene polymer as an example.It is divided into the polymer of doping azo-compound, side chain containing azo and azo main chain again.Mix
The polymer film orientational order parameter number of miscellaneous azo-compound and the side chain containing azo is larger, and effect is preferable, but because the light of azo is different
Structure turns to reversible change, and heat endurance and photostability are poor.The polymer of azo main chain, heat endurance and photostability compared with
It is good, but orientational order parameter number is smaller, use range is restricted.
(2) light degradation type：Photosensitive polyimide.Polyimides has excellent heat endurance and processing characteristics, photosensitive
Property polyimides, light degradation that can be by selectivity and light degradation cross-linking reaction again, trigger surface anisotropy, cause liquid crystal
Orientations.
However, either light degradation or light degradation be crosslinked again after polyimides, or decompose generate polyimides
Small molecule monomer, or the hydroxyl with active hydrogen is formd, great interference is caused to the stability of liquid crystal display device,
It has impact on device lifetime.
(3) photo-crosslinking type：Cinnamic acid derivative, coumarin derivative, chalcone derivative.In linear polarizing light irradiation
Under, it can occur to generate the axle selective light cross-linking reaction of cyclobutane on these derivative side chains, thus it is each to different in surface generation
Property so that liquid crystal molecule is along face uniaxial orientation.Different intensity of illumination and light application time are controlled, different pre-tilt angles can be obtained
Liquid crystal aligning arranges.
Although photo-crosslinking type derivative has good orientation characteristic, liquid crystal property is not had an impact, these spread out
The stability of biology still has to be hoisted.This is mostly polymeric derivative when being mainly photo-crosslinking type derivative use, derivative
Monomer is mostly the monomer of esters of acrylic acid.By taking cinnamic acid derivative as an example, simultaneously containing double in acrylate group in monomer
Double bond in key and cinnamate group, in order to obtain light alignment film, the first step selectively triggers the double bond in acrylate group,
Then reselection triggers the double bond in cinnamate group.In order to reduce the interference of two-step reaction as far as possible, because second step
Polarization must be used light-initiated, so the first step uses thermal initiation more.
In order to improve efficiency of initiation, thermal initiator (such as benzoyl peroxide, azodiisobutyronitrile) is commonly incorporated into, and light draws
Send out agent (such as 1- hydroxycyclohexyl phenyl ketones, 2- methyl isophthalic acids-(4- methyl mercaptos phenyl) -2- morpholine -1- acetone).But these trigger
Agent does not remove from product after completing to trigger, the catabolite after the initiator of residual and initiation, reduces material
Stability.
Therefore, there is still a need for exploitation is with stability good light control orientation material and photo orientated film.
The content of the invention
Goal of the invention：The purpose of the present invention is overcome the deficiencies in the prior art, there is provided it is a kind of for light orientation field can
Polymerisable liquid crystal composition, the polymerizable liquid crystal composition have good stability, it is not necessary to additionally add thermal initiator.This hair
The polymerizable liquid crystal composition of bright offer utilizes influence of the end functional group of double bond two to double bond reactivity, creative to combine
A kind of polymerisable liquid crystal of visible absorption response is added in thing, it is in situ in the case where being not added with initiator progressively to polymerize, obtain stability
Good photo orientated film.
Technical scheme, in order to complete foregoing invention purpose, the invention provides a kind of polymerizable liquid crystal composition, and it is wrapped
Include：
The polymerisable liquid crystal compound with cinnamic acid structure shown at least one formula I
And
Polymerisable liquid crystal compound shown at least one formula II
Wherein,
The R1Expression-H or-CH3；
The R2Represent alkyl, phenyl, the tolyl of 1-6 carbon atom, methoxyphenyl；
The L represents the alkylidene of singly-bound, 1-11 carbon atom；
The A1And A2It is identical and different, it is each independent to representWith
The Ar is represented
The X1、X2、X3、X4、X5、X6、X7And X8Can be with identical and different, respective independent expression-H or-F；
The Y1、Y2And Y3It is identical and different, respective independent expression-H ,-F ,-Cl or-CH3；
Described a, b are identical and different with c, each independent to represent 0 or 1；
Described m, n and k are identical and different, each independent to represent 0,1 or 2.
In certain embodiments of the present invention, one or more of the compound of the formula I in following structure：
And
Wherein,
The R1Expression-H or-CH3；
The R2Represent alkyl, phenyl, the tolyl of 1-6 carbon atom, methoxyphenyl；
The L represents the alkylidene of 1-11 carbon atom；
The X1、X2、X3、X4、X5、X6、X7And X8Can be with identical and different, respective independent expression-H or-F；The b represents 0
Or 1.
In certain embodiments of the present invention, one or more of the compound of the formula I in following structure：
And
In certain embodiments of the present invention, one or more of the compound of the formula I in following structure：
And
In certain embodiments of the present invention, one or more of the compound of the formula I in following structure：
And
In certain embodiments of the present invention, one or more of the compound of the formula I in following structure：
And
In certain embodiments of the present invention, the one kind or more of the compound of the formula II in following structure
Kind：
And
In certain embodiments of the present invention, compound shown in formula II accounts for the polymerizable liquid crystal composition weight hundred
It is 0.01%-2% to divide ratio.
Preferably, in certain embodiments of the present invention, compound shown in formula II accounts for the polymerizable liquid
Crystal composite percentage by weight is 0.01%-1%.
In certain embodiments of the present invention, compound shown in formula I accounts for the polymerizable liquid crystal composition weight hundred
It is 98-99.9% to divide ratio.
Preferably, in certain embodiments of the present invention, compound shown in formula I accounts for the polymerisable liquid crystal
Composition weight percentage is 99-99.9%.
In certain embodiments of the present invention, compound shown in formula I -2 accounts for the polymerizable liquid crystal composition weight
Percentage is 0-70%, preferably 30-70%.
In certain embodiments of the present invention, compound shown in formula I -5 accounts for the polymerizable liquid crystal composition weight
Percentage is 0-40%, preferably 20-40%.
In certain embodiments of the present invention, compound shown in formula I -7 accounts for the polymerizable liquid crystal composition weight
Percentage is 0-99.9%, preferably 30-99.9%.
Present invention also offers a kind of application of polymerizable liquid crystal composition in light orientation field.
In the prior art, applied to the material in photo orientated technology, entered using the high polymer material after thermal initiation
Row spin-coating film, orientation layer adhesion are inadequate；Catabolite after the initiator of first step thermal initiation process residual and initiation, with
Light alignment materials poor compatibility, reduces the stability of material, have impact on device lifetime.Polymerisable liquid crystal group of the present invention
Compound compared with prior art, has more superior stability.Shadow using the end functional group of double bond two to double bond reactivity
Ring, creative adds polymerisable liquid crystal (wherein compound shown in a kind of formula II of visible absorption response in the composition
II -2 uv absorption spectra is as shown in Figure 1), polymerisation is carried out in the case where need not additionally add initiator, is a kind of non-
The often good composition available for light orientation field.Visible light-responded polymerisable liquid crystal is also assisted in polymerisation itself,
The problem of being not in light alignment materials poor compatibility.Because visible light-responded polymerisable liquid crystal addition is seldom, difunctionality
The presence of group high molecular to chain will not be formed and had an impact, thus not influence the stability of photo orientated film.And propylene
Acid ester functionality widely applies in adhesive, and the film forming speed after initiation is fast, has good adhesiving effect to various substrates,
In-situ polymerization after coating, there is very good adhesion.
The preparation method of polymerizable liquid crystal composition of the present invention, weigh one or more generalformulaⅰcompounds and corresponding
The compound of formula II of ratio, sufficient physical agitation blending is carried out under dark conditions, that is, obtains of the present invention can be used for
The liquid-crystal composition of light orientation.
Visible light solidifying performance is tested：Under feux rouges environment, composition is dissolved in corresponding solvent, with spin coating mode
Film forming, after removing solvent, it is placed in visible ray lower 30 minutes.With the film after the above-mentioned solidification of acetone solution, occur gluey or cotton-shaped
Insoluble matter, illustrate that composition can solidify under visible light.
Linear cross-linking properties test：Under feux rouges environment, composition is dissolved in corresponding solvent, with spin coating mode into
Film, after removing solvent, it is placed in visible ray lower 30 minutes.The film after above-mentioned solidification is dissolved with methylene chloride acetone, it is saturating to clarify
Bright shape liquid, illustrates that composition does not form cross-linked structure, is linear polymeric.
Orientation characteristic is tested：Under the conditions of feux rouges, composition is dissolved in corresponding solvent, mass concentration is made as 1%
Solution, in glass baseplate surface, with 100 rpms of rotating speed spin coating 30 seconds, form required film.It is visible to be placed in room temperature
Lower 30 minutes of light.Using the linearly polarized light of certain angle, irradiate 30 seconds.The substrate of the coated film of irradiation will be completed, using liquid
The brilliant general preparation method of testing cassete, irrigate nematic liquid crystal and seal.Under petrographic microscope, the dark of uniform compact is such as observed
State, without obvious light leak.Illustrate that composition can reach light orientation orientation characteristic.
Brief description of the drawings
Fig. 1 represents the uv absorption spectra of compound ii -2.
Embodiment
Illustrate the present invention below with reference to specific embodiment.It should be noted that the following examples are the present invention
Example, be only used for illustrating the present invention, and be not limited to the present invention.In the case of without departing from present subject matter or scope,
Other combinations in present inventive concept and various improvement can be carried out.
Embodiment 1
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 2
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 3
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 4
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 5
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 6
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 7
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 8
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 9
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 10
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 11
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 12
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 13
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Embodiment 14
1. polymerizable liquid crystal composition, it is made up of following materials：
2. performance test：
Visible light solidifying performance is tested：It can solidify under visible light, pass through；
Linear cross-linking properties test：For linear polymeric, pass through；
Orientation characteristic is tested：It can be orientated, pass through.
Above example shows that polymerizable liquid crystal composition provided by the invention need not additionally add thermal initiator, tool
Have good stability, the good photo orientated film of stability can be prepared, can overcome the deficiencies in the prior art, achieve very
Good technique effect.
The above described is only a preferred embodiment of the present invention, any formal limitation not is made to the present invention, though
So the present invention is disclosed above with preferred embodiment, but is not limited to the present invention, any to be familiar with this professional technology people
Member, without departing from the scope of the present invention, when the technology contents using the disclosure above make a little change or modification
For the equivalent embodiment of equivalent variations, as long as being the technical spirit pair according to the present invention without departing from technical solution of the present invention content
Any simple modification, equivalent change and modification that above example is made, in the range of still falling within technical solution of the present invention.
Claims (8)
1. a kind of polymerizable liquid crystal composition, including：
The polymerisable liquid crystal compound with cinnamic acid structure shown at least one formula I
And
Polymerisable liquid crystal compound shown at least one formula II
Wherein,
The R1Expression-H or-CH3；
The R2Represent the alkyl of 1-6 carbon atom；
The L represents the alkylidene of singly-bound, 1-11 carbon atom；
The A1And A2It is identical and different, it is each independent to represent
The Ar is represented
The X1、X2、X3、X4、X5、X6、X7And X8Can be with identical and different, respective independent expression-H or-F；
The Y1、Y2And Y3It is identical and different, respective independent expression-H ,-F ,-Cl or-CH3；
Described a, b are identical and different with c, each independent to represent 0 or 1；
Described m, n and k are identical and different, each independent to represent 0,1 or 2；
It is 98-99.9% that compound shown in formula I, which accounts for polymerizable liquid crystal composition percentage by weight, and compound shown in formula II accounts for
Polymerizable liquid crystal composition percentage by weight is 0.01%-2% ".
2. polymerizable liquid crystal composition according to claim 1, it is characterised in that the compound of the formula I is selected from such as
One or more in lower structure：
Wherein,
The R1Expression-H or-CH3；
The R2Represent the alkyl of 1-6 carbon atom；
The L represents the alkylidene of 1-11 carbon atom；
The X1、X2、X3、X4、X5、X6、X7And X8Can be with identical and different, respective independent expression-H or-F；
The b represents 0 or 1.
3. polymerizable liquid crystal composition according to claim 2, it is characterised in that the compound of the formula I is selected from such as
One or more in lower structure：
4. polymerizable liquid crystal composition according to claim 2, it is characterised in that the compound of the formula I is selected from such as
One or more in lower structure：
5. polymerizable liquid crystal composition according to claim 2, it is characterised in that the compound of the formula I is selected from such as
One or more in lower structure：
6. polymerizable liquid crystal composition according to claim 2, it is characterised in that the compound of the formula I is selected from such as
One or more in lower structure：
7. polymerizable liquid crystal composition according to claim 1, it is characterised in that the compound of the formula II is selected from such as
One or more in lower structure：
8. according to the polymerizable liquid crystal composition any one of claim 1-7, it is characterised in that the polymerisable liquid crystal
Composition is applied to light orientation field.
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| KR20190042065A (en) * | 2016-08-31 | 2019-04-23 | 닛산 가가쿠 가부시키가이샤 | Retardation film having water vapor barrier property and manufacturing method thereof |
| 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 |
| JPWO2020008826A1 (en) * | 2018-07-04 | 2021-07-08 | Jnc株式会社 | Compounds, liquid crystal compositions and liquid crystal display devices |
| CN110713838B (en) * | 2018-07-13 | 2022-07-08 | 石家庄诚志永华显示材料有限公司 | Polymerizable liquid crystal composition and liquid crystal display device |
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| CN101354459A (en) * | 2008-09-22 | 2009-01-28 | 北京科技大学 | Method for preparing liquid-crystal film material capable of reflecting circle polarized light and non-polarized light |
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