CN103409145A - Polymerizable liquid crystal composition and application thereof - Google Patents
Polymerizable liquid crystal composition and application thereof Download PDFInfo
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- CN103409145A CN103409145A CN2013103290143A CN201310329014A CN103409145A CN 103409145 A CN103409145 A CN 103409145A CN 2013103290143 A CN2013103290143 A CN 2013103290143A CN 201310329014 A CN201310329014 A CN 201310329014A CN 103409145 A CN103409145 A CN 103409145A
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Abstract
The invention provides a polymerizable liquid crystal composition. The polymerizable liquid crystal composition comprises at least one compound conforming to a general formula I and including two polymerizable groups, which serving as a first component, and at least one compound conforming to a general formula II and including one polymerizable group, which serving as a second component. Compared with other polymerizable liquid crystal compositions in the prior art, the polymerizable liquid crystal composition provided by the invention has a lower melting point, larger optical anisotropy and longer supercooling time, and can be used for optical anisotropic bodies. The invention also provides application of the polymerizable liquid crystal composition in the aspect of the optical anisotropic bodies.
Description
Technical field
The present invention relates to a kind of polymerizable liquid crystal compound and the application aspect optically anisotropic body thereof.
Background technology
In recent years, along with the development of informationized society, simple liquid-crystal display can not meet the pursuit of people to showing, needs to use the optically anisotropic body of various functions to help improve the quality of demonstration.For example can carry out optical compensation to improve viewing angle characteristic with polarizer, can carry out the light recycling to improve optical efficiency by brightness enhancement film, can use patterned retardation film (Patterned Retarder) or lens pillar film (Lenticular Lens film) to change the conversion of optical parametric to realize that two-dimensional/three-dimensional shows.
Optically anisotropic body can carry out mechanical workout by the polymkeric substance common to be made, and for example can carry out polycarbonate film mechanical stretching and obtain polarizer, can carry out modeling hot pressing to polyester film and obtain the lens pillar film.But common polymkeric substance not designs for optics, so exist such as thickness is too large, the optical delay amount is too little, can not control the defect such as microstructure with the optically anisotropic body that this materials and methods is made.
Report has been arranged the making of polymerizable liquid crystal for optically anisotropic body, polymerizable liquid crystal has significant anisotropy, larger optical delay amount can be provided with less thickness, and can control by the known method such as mechanical friction or light orientation the arrangement mode of polymerizable liquid crystal, thereby control accurately microstructure, realize the optical effect strengthened.
Regrettably, also there are a lot of defects in current polymerizable liquid crystal monomer, for example the fusing point of the polymerizable liquid crystal monomer of U.S. Pat 6136225 records is too high, in actual production, need under the temperature condition of 80～90 ℃, just can operate, this has increased energy consumption greatly, and also causes easily that at high temperature orientation inequality, abnormal polymerization etc. have a strong impact on the defect of optical quality.
Also adopt the method for making polymerizable liquid crystal compound to improve the performance of polymerizable liquid crystal.It is a kind of than the polymerizable liquid crystal compound of low melting point that Japanese Patent JP2003193053 provides, but have the problem of serious orientation inequality.It is a kind of than the polymerizable liquid crystal compound of low melting point that U.S. Pat 6090308 provides, but the problems such as existence and stability is poor, easy crystallization.
Therefore, need to obtain the better polymerizable liquid crystal compound of performance, have lower fusing point, larger optical anisotropy and the cool time excessively of growing.The long cool time of crossing helps to improve the stability of polymerizable liquid crystal compound in the nematic liquid crystal state, is conducive to the constructing operation such as coating, orientation.
Summary of the invention
The purpose of this invention is to provide a kind of polymerizable liquid crystal compound with excellent properties.
The present inventor has been found that by using specific polymerizable liquid crystal compound, can address the above problem, thereby complete the present invention.
One aspect of the present invention provides a kind of polymerizable liquid crystal compound, comprises:
At least a compound that meets formula I that comprises two polymerizable groups as the first component
At least a compound that meets the general formula II that comprises a polymerizable groups as second component
Wherein,
P
1, P
2And P
3Identical or different, mean independently of one another
Sp
1And Sp
2Identical or different, mean that independently of one another carbonatoms is spacer groups or the singly-bound of 1-12;
R
1Mean that H, carbonatoms are alkyl or the alkoxyl group of 1-7, or carbonatoms is thiazolinyl or the alkene oxygen base of 2-7;
X
1And X
2Identical or different, independently of one another expression-O-,-COO-,-OCO-,-OCO-O-or singly-bound;
Identical or different, mean independently of one another
One or more hydrogen atoms on described ring can be replaced by fluorine atom;
Z
1, Z
2, Z
3, Z
4, Z
5And Z
6Identical or different, mean independently of one another singly-bound ,-O-,-CH
2CH
2-,-CH=CH-,-COO-,-OCO-,-OCOO-,-CH
2-,-CH
2O-,-OCH
2-or-C ≡ C-;
L, when occurring, means that independently of one another H, F or carbonatoms are the alkyl of 1-3 at every turn;
M and n are identical or different, mean independently of one another 0,1 or 2.
Polymerizable liquid crystal compound of the present invention, at least a form of described the first component in compound shown in formula I a:
Wherein,
P
1And P
2Identical or different, mean independently of one another
Sp
1And Sp
2Identical or different, mean that independently of one another carbonatoms is spacer groups or the singly-bound of 1-12;
X
1And X
2Identical or different, independently of one another expression-O-,-COO-,-OCO-,-OCO-O-or singly-bound;
Z
1And Z
2Identical or different, mean independently of one another singly-bound ,-CH
2CH
2-,-COO-,-OCO-,-CH
2O-,-OCH
2-or-C ≡ C-;
L means H, F or CH
3.
Polymerizable liquid crystal compound of the present invention, at least a form of described second component in the compound shown in formula II a:
Wherein,
R
1Mean that H, carbonatoms are alkyl or the alkoxyl group of 1-7, or carbonatoms is thiazolinyl or the alkene oxygen base of 2-7;
P
3Mean
Identical or different, mean independently of one another
One or more hydrogen atoms on described ring can be replaced by fluorine atom;
Z
4And Z
5Identical or different, mean independently of one another singly-bound ,-CH
2CH
2-,-CH=CH-,-COO-,-OCO-,-CH
2O-,-OCH
2-or-C ≡ C-;
N means 0 or 1.
Polymerizable liquid crystal compound of the present invention, described the first component accounts for 30～70% of described polymerizable liquid crystal compound gross weight; And described second component accounts for 30～70% of described polymerizable liquid crystal compound gross weight.
In some embodiments, preferred at least a composition of described the first component in the compound shown in formula I a-1 and I a-2:
Wherein,
P, q, r and s are identical or different, mean independently of one another the integer of 1-6.
In some embodiments, preferred at least a composition of described the first component in the compound shown in formula II a-1 and II a-2:
Wherein,
U and v are identical or different, mean independently of one another the integer of 0-6.
Polymerizable liquid crystal compound of the present invention comprises:
Account at least a compound of the formula I a-1 of described polymerizable liquid crystal compound gross weight 15～35%
Account at least a compound of the formula I a-2 of described polymerizable liquid crystal compound gross weight 15～35%
Account at least a compound of the general formula II a-1 of described polymerizable liquid crystal compound gross weight 15～35%
Account at least a compound of the general formula II a-2 of described polymerizable liquid crystal compound gross weight 15～35%
Wherein,
P, q, r and s are identical or different, mean independently of one another the integer of 1-6;
U and v are identical or different, mean independently of one another the integer of 0-6.
Another aspect of the present invention provides the purposes of described polymerizable liquid crystal compound aspect optically anisotropic body.
With other polymerizable liquid crystal compounds of prior art, compare, polymerizable liquid crystal compound of the present invention has lower fusing point, larger optical anisotropy and the cool time excessively of growing, can be for the purposes of optically anisotropic body.
Embodiment
Following examples are for illustrating the present invention, but are not used for limiting the scope of the invention, and all other do not break away from the equivalence completed under disclosed spirit and change or modify, and all should be included in the scope of the said claims.
Reference literature Makromol.Chem., the described method of (1989) 190,2255-2268, US6136225 and JPH083111A has been synthesized polymerizable liquid crystal compound involved in the present invention:
Reagent used in the present invention and other raw materials are commercially available commercial materials.
Polymerizable liquid crystal compound in following embodiment is all prepared as follows, and carries out fusing point (Mp, ℃), clearing point (Cp, ℃) and the test of degree of birefringence (Δ n) and the mensuration of extrapolation parameter:
1) preparation of composition
According to formula rate, each polymerizable compound is packed among same vessel, keep 60 ℃ to stir half an hour, obtain milky white liquid.
2) parameter testing
With the heating curve figure of dsc (DSC) test resulting composition, and the judgement fusing point (Mp, ℃) and clearing point (Cp, ℃).
Choose the commodity liquid crystal that is numbered TS023-102 of Jiangsu Hecheng Display Technology Co., Ltd.'s production as parent, the composition of gained is dissolved in parent with 10% part by weight, the degree of birefringence of test mixing thing, and according to the ratio of the composition added in parent, according to the degree of birefringence Δ n(20 ℃ of the extrapolated polymerizable liquid crystal compound of linear relationship, 589nm).
3) cross the cool time test
The composition just prepared is placed in vial and sealing, lucifuge is placed under the environment of 20 ℃, after after a while, starts to have a small amount of crystal to separate out on the bottle wall.To start to separate out the time consumed be cool time from preparing crystal.
Comparative Examples 1
The current known polymerizable liquid crystal monomer that can directly use:
The performance parameter test result:
Mp：65℃；
Cp：122℃；
Δn：0.151；
Cross cool time: 4 hours
The fusing point of this polymerizable liquid crystal monomer is higher, therefore needs higher construction temperature (80～90 ℃), and polymerization easily meets accident; In addition, cross cool time and only have 4 hours, therefore be very easy to occur the abnormal bad phenomenon of orientation.
Embodiment 1:
The liquid-crystal composition formula is as described below:
The performance parameter test result:
Mp：37℃；
Cp：86℃；
Δn：0.183；
Cross cool time: 30 days.
Polymerizable liquid crystal compound provided by the invention has lower fusing point, so construction temperature lower (usually at 40 ℃); Have higher degree of birefringence, therefore can use material still less just can reach optical effect; And have the longer cool time of crossing, and greatly promoted the stability of polymerizable liquid crystal compound, can avoid the generation of the bad phenomenon such as orientation is abnormal.
Claims (9)
1. polymerizable liquid crystal compound comprises:
At least a compound that meets formula I of two polymerizable groups that comprises is as the first component
At least a compound that meets the general formula II of a polymerizable groups that comprises is as second component
Wherein,
P
1, P
2And P
3Identical or different, mean independently of one another
Sp
1And Sp
2Identical or different, mean that independently of one another carbonatoms is spacer groups or the singly-bound of 1-12;
R
1Mean that H, carbonatoms are alkyl or the alkoxyl group of 1-7, or carbonatoms is thiazolinyl or the alkene oxygen base of 2-7;
X
1And X
2Identical or different, independently of one another expression-O-,-COO-,-OCO-,-OCO-O-or singly-bound;
Z
1, Z
2, Z
3, Z
4, Z
5And Z
6Identical or different, mean independently of one another singly-bound ,-O-,-CH
2CH
2-,-CH=CH-,-COO-,-OCO-,-OCOO-,-CH
2-,-CH
2O-,-OCH
2-or-C ≡ C-;
L, when occurring, means that independently of one another H, F or carbonatoms are the alkyl of 1-3 at every turn;
M and n are identical or different, mean independently of one another 0,1 or 2.
2. polymerizable liquid crystal compound according to claim 1, is characterized in that, at least a form of described the first component in compound shown in formula I a:
Wherein,
P
1And P
2Identical or different, mean independently of one another
Sp
1And Sp
2Identical or different, mean that independently of one another carbonatoms is spacer groups or the singly-bound of 1-12;
X
1And X
2Identical or different, independently of one another expression-O-,-COO-,-OCO-,-OCO-O-or singly-bound;
Z
1And Z
2Identical or different, mean independently of one another singly-bound ,-CH
2CH
2-,-COO-,-OCO-,-CH
2O-,-OCH
2-or-C ≡ C-;
L means H, F or CH
3.
3. polymerizable liquid crystal compound according to claim 1, is characterized in that, at least a form of described second component in the compound shown in formula II a:
Wherein,
R
1Mean that H, carbonatoms are alkyl or the alkoxyl group of 1-7, or carbonatoms is thiazolinyl or the alkene oxygen base of 2-7;
P
3Mean
Z
4And Z
5Identical or different, mean independently of one another singly-bound ,-CH
2CH
2-,-CH=CH-,-COO-,-OCO-,-CH
2O-,-OCH
2-or-C ≡ C-;
N means 0 or 1.
4. according to the described polymerizable liquid crystal compound of claims 1 to 3 any one, it is characterized in that, described the first component accounts for 30～70% of described polymerizable liquid crystal compound gross weight; And described second component accounts for 30～70% of described polymerizable liquid crystal compound gross weight.
5. polymerizable liquid crystal compound according to claim 4, is characterized in that, at least a form of described the first component in the compound shown in formula I a-1 and I a-2:
Wherein,
P, q, r and s are identical or different, mean independently of one another the integer of 1-6.
6. polymerizable liquid crystal compound according to claim 4, is characterized in that, at least a form of described the first component in the compound shown in formula II a-1 and II a-2:
Wherein,
U and v are identical or different, mean independently of one another the integer of 0-6.
7. according to the described polymerizable liquid crystal compound of claim 5 or 6, it is characterized in that, described polymerizable liquid crystal compound comprises:
Account at least a compound of the formula I a-1 of described polymerizable liquid crystal compound gross weight 15～35%
Account at least a compound of the formula I a-2 of described polymerizable liquid crystal compound gross weight 15～35%
Account at least a compound of the general formula II a-1 of described polymerizable liquid crystal compound gross weight 15～35%
Account at least a compound of the general formula II a-2 of described polymerizable liquid crystal compound gross weight 15～35%
Wherein,
P, q, r and s are identical or different, mean independently of one another the integer of 1-6;
U and v are identical or different, mean independently of one another the integer of 0-6.
8. polymerizable liquid crystal compound according to claim 7, is characterized in that, described polymerizable liquid crystal compound comprises:
Account for the compound of described polymerizable liquid crystal compound gross weight 25%
Account for the compound of described polymerizable liquid crystal compound gross weight 25%
Account for the compound of described polymerizable liquid crystal compound gross weight 25%
Account for the compound of described polymerizable liquid crystal compound gross weight 25%
9. according to the described polymerizable liquid crystal compound of claim 1～8 any one, preparing the application of optically anisotropic body.
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Cited By (5)
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| CN105441089A (en) * | 2015-01-26 | 2016-03-30 | 江苏和成新材料有限公司 | Polymeric liquid crystal composition and application thereof |
| CN105885871A (en) * | 2016-02-25 | 2016-08-24 | 江苏和成新材料有限公司 | Polymerizable liquid crystal composition |
| WO2018047806A1 (en) * | 2016-09-09 | 2018-03-15 | Dic株式会社 | Polymerizable liquid crystal composition and optical film using same |
| CN109913240A (en) * | 2017-12-12 | 2019-06-21 | 江苏和成显示科技有限公司 | Polymerizable liquid crystal compound and its application |
| TWI673349B (en) * | 2014-05-13 | 2019-10-01 | 日商迪愛生股份有限公司 | Nematic liquid crystal composition and liquid crystal display element using same |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI673349B (en) * | 2014-05-13 | 2019-10-01 | 日商迪愛生股份有限公司 | Nematic liquid crystal composition and liquid crystal display element using same |
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