CN103409145B - Polymerizable liquid crystal compound and application thereof - Google Patents
Polymerizable liquid crystal compound and application thereof Download PDFInfo
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- CN103409145B CN103409145B CN201310329014.3A CN201310329014A CN103409145B CN 103409145 B CN103409145 B CN 103409145B CN 201310329014 A CN201310329014 A CN 201310329014A CN 103409145 B CN103409145 B CN 103409145B
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Abstract
The invention provides a kind of polymerizable liquid crystal compound, comprise: at least one comprises the compound meeting formula I of two polymerizable groups as the first component; And at least one comprises the compound meeting general formula II of a polymerizable groups as second component.Compared with other polymerizable liquid crystal compounds of prior art, polymerizable liquid crystal compound of the present invention has lower fusing point, larger optical anisotropy and longer cool time excessively, may be used for the purposes of optically anisotropic body.The present invention also provides the application of polymerizable liquid crystal compound in optically anisotropic body.
Description
Technical field
The present invention relates to a kind of polymerizable liquid crystal compound and the application in 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 display, needs to use the optically anisotropic body of various function to help improve the quality of display.Polarizer such as can be used to carry out optical compensation to improve viewing angle characteristic, brightness enhancement film can be used to recycle to improve optical efficiency to carry out light, patterned retardation film (Patterned Retarder) or lens pillar film (Lenticular Lens film) can be used to change optical parametric to realize the conversion of two-dimensional/three-dimensional display.
Optically anisotropic body can be made by common polymkeric substance is carried out mechanical workout, such as, polycarbonate film can be carried out mechanical stretching and obtain polarizer, polyester film can be carried out modeling hot pressing and obtain lens pillar film.But common polymkeric substance not designs for optics, so also exist such as with the optically anisotropic body that this materials and methods is made, thickness is too large, optical delay amount is too little, can not control the defects such as microstructure.
There is report 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 the arrangement mode of polymerizable liquid crystal can be controlled by the known method such as mechanical friction or light orientation, thus control microstructure accurately, realize the optical effect strengthened.
Regrettably, also there is a lot of defect in current polymerizable liquid crystal monomer, the fusing point of the polymerizable liquid crystal monomer that such as US Patent No. 6136225 is recorded is too high, need in actual production just to operate under the temperature condition of 80 ~ 90 DEG C, this considerably increases energy consumption, and at high temperature also easily cause orientation inequality, abnormal polymerization etc. to have a strong impact on the defect of optical quality.
Also the method making polymerizable liquid crystal compound is adopted to improve the performance of polymerizable liquid crystal.Japanese Patent JP2003193053 provides a kind of polymerizable liquid crystal compound compared with low melting point, but there is the problem of serious orientation inequality.US Patent No. 6090308 provides a kind of polymerizable liquid crystal compound compared with low melting point, but the problems such as existence and stability is poor, easy crystallization.
Therefore, need to obtain the better polymerizable liquid crystal compound of performance, there is lower fusing point, larger optical anisotropy and longer cool time excessively.Long cool time of crossing contributes to improving polymerizable liquid crystal compound in the stability of nematic liquid crystal state, is conducive to the constructing operation such as coating, orientation.
Summary of the invention
The object 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 solve the problem, thus complete the present invention.
One aspect of the present invention provides a kind of polymerizable liquid crystal compound, comprises:
At least one as the first component comprises the compound meeting formula I of two polymerizable groups
At least one as second component comprises the compound meeting general formula II of a polymerizable groups
Wherein,
P
1, P
2and P
3identical or different, represent independently of one another
Sp
1and Sp
2identical or different, represent that carbonatoms is spacer groups or the singly-bound of 1-12 independently of one another;
R
1expression 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, represent-O-,-COO-,-OCO-,-OCO-O-or singly-bound independently of one another;
identical or different, represent independently of one another
one or more hydrogen atoms on described ring can be replaced by fluorine atoms;
Z
1, Z
2, Z
3, Z
4, Z
5and Z
6identical or different, represent singly-bound ,-O-,-CH independently of one another
2cH
2-,-CH=CH-,-COO-,-OCO-,-OCOO-,-CH
2-,-CH
2o-,-OCH
2-or-C ≡ C-;
L, when occurring at every turn, represents that H, F or carbonatoms are the alkyl of 1-3 independently of one another;
M and n is identical or different, represents 0,1 or 2 independently of one another.
Polymerizable liquid crystal compound of the present invention, described first component is made up of at least one in compound shown in formula I a:
Wherein,
P
1and P
2identical or different, represent independently of one another
Sp
1and Sp
2identical or different, represent that carbonatoms is spacer groups or the singly-bound of 1-12 independently of one another;
X
1and X
2identical or different, represent-O-,-COO-,-OCO-,-OCO-O-or singly-bound independently of one another;
Z
1and Z
2identical or different, represent singly-bound ,-CH independently of one another
2cH
2-,-COO-,-OCO-,-CH
2o-,-OCH
2-or-C ≡ C-;
L represents H, F or CH
3.
Polymerizable liquid crystal compound of the present invention, described second component is made up of at least one in the compound shown in formula II a:
Wherein,
R
1expression H, carbonatoms are alkyl or the alkoxyl group of 1-7, or carbonatoms is thiazolinyl or the alkene oxygen base of 2-7;
P
3represent
identical or different, represent independently of one another
one or more hydrogen atoms on described ring can be replaced by fluorine atoms;
Z
4and Z
5identical or different, represent singly-bound ,-CH independently of one another
2cH
2-,-CH=CH-,-COO-,-OCO-,-CH
2o-,-OCH
2-or-C ≡ C-;
N represents 0 or 1.
Polymerizable liquid crystal compound of the present invention, described 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, preferably described first component is made up of at least one in the compound shown in formula I a-1 and I a-2:
Wherein,
P, q, r and s are identical or different, represent the integer of 1-6 independently of one another.
In some embodiments, preferably described first component is made up of at least one in the compound shown in formula II a-1 and II a-2:
Wherein,
U and v is identical or different, represents the integer of 0-6 independently of one another.
Polymerizable liquid crystal compound of the present invention comprises:
Account at least one compound of the formula I a-1 of described polymerizable liquid crystal compound gross weight 15 ~ 35%
Account at least one compound of the formula I a-2 of described polymerizable liquid crystal compound gross weight 15 ~ 35%
Account at least one compound of general formula II a-1 of described polymerizable liquid crystal compound gross weight 15 ~ 35%
Account at least one compound of 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, represent the integer of 1-6 independently of one another;
U and v is identical or different, represents the integer of 0-6 independently of one another.
Another aspect of the present invention provides the purposes of described polymerizable liquid crystal compound in optically anisotropic body.
Compared with other polymerizable liquid crystal compounds of prior art, polymerizable liquid crystal compound of the present invention has lower fusing point, larger optical anisotropy and longer cool time excessively, may be used for the purposes of optically anisotropic body.
Embodiment
Following examples for illustration of the present invention, but are not used for limiting the scope of the invention, and under all other does not depart from disclosed spirit, the equivalence that completes changes or modifies, and all should be included in the scope of the said claims.
Reference literature Makromol.Chem., the method described in (1989) 190,2255-2268, US6136225 and JPH083111A has 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 prepared all as follows, and carries out fusing point (Mp, DEG C), clearing point (Cp, DEG C) 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 loaded among same vessel, keep 60 DEG C to stir half an hour, obtain milky white liquid.
2) parameter testing
Test the heating curve figure of resulting composition by dsc (DSC), and judge fusing point (Mp, DEG C) and clearing point (Cp, DEG C).
Choose the commodity liquid crystal being numbered TS023-102 of Jiangsu Hecheng Display Technology Co., Ltd.'s production as parent, by the composition of gained with 10% part by weight be dissolved in parent, 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 DEG C of the extrapolated polymerizable liquid crystal compound of linear relationship, 589nm).
3) cool time test is crossed
The composition just prepared to be placed in vial and to seal, under lucifuge is placed on the environment of 20 DEG C, through after a period of time, bottle wall starting have a small amount of crystal to separate out.From preparing crystal, separate out the time consumed was cool time.
Comparative example 1
The known polymerizable liquid crystal monomer that can directly use at present:
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, and therefore need higher construction temperature (80 ~ 90 DEG C), easily meet accident polymerization; In addition, cross cool time and only have 4 hours, be therefore very easy to the bad phenomenon that orientation exception occurs.
Embodiment 1:
Liquid crystal combination composition formula is as described below:
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, therefore construction temperature lower (usually at 40 DEG C); There is higher degree of birefringence, less material therefore can be used just can to reach optical effect; And there is longer cool time excessively, greatly improve the stability of polymerizable liquid crystal compound, the generation of the bad phenomenon such as orientation exception can be avoided.
Claims (3)
1. a polymerizable liquid crystal compound, is characterized in that, described polymerizable liquid crystal compound comprises:
Account at least one compound of the formula I a-1 of described polymerizable liquid crystal compound gross weight 15 ~ 35%
Account at least one compound of the formula I a-2 of described polymerizable liquid crystal compound gross weight 15 ~ 35%
Account at least one compound of general formula II a-1 of described polymerizable liquid crystal compound gross weight 15 ~ 35%
and
Account at least one compound of 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, represent the integer of 1-6 independently of one another;
U and v is identical or different, represents the integer of 0-6 independently of one another.
2. polymerizable liquid crystal compound according to claim 1, 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%
and
Account for the compound of described polymerizable liquid crystal compound gross weight 25%
3. the polymerizable liquid crystal compound described in any one of claim 1 ~ 2 is preparing the application of optically anisotropic body.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5971448B2 (en) * | 2014-05-13 | 2016-08-17 | Dic株式会社 | Nematic liquid crystal composition and liquid crystal display device using the same |
| CN105441089B (en) * | 2015-01-26 | 2018-06-26 | 江苏和成新材料有限公司 | Polymerizable liquid crystal compound and its application |
| CN105885871B (en) * | 2016-02-25 | 2018-05-08 | 江苏和成新材料有限公司 | A kind of polymerizable liquid crystal compound |
| CN109715761A (en) * | 2016-09-09 | 2019-05-03 | Dic株式会社 | Polymerizable liquid crystal compound and the optical film for using it |
| CN109913240B (en) * | 2017-12-12 | 2022-03-11 | 江苏和成显示科技有限公司 | Polymerizable liquid crystal composition and use thereof |
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| JP2003193053A (en) * | 2001-12-26 | 2003-07-09 | Dainippon Ink & Chem Inc | Polymerizable liquid crystal composition and optical anisotropic object using the same |
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| CN102911052A (en) * | 2012-10-13 | 2013-02-06 | 江苏和成显示科技股份有限公司 | Polymerized star compound and polymerized product and application thereof in liquid crystal device |
| CN103059036A (en) * | 2011-10-21 | 2013-04-24 | Dic株式会社 | Polymerizable chiral compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI659091B (en) * | 2009-02-20 | 2019-05-11 | 迪愛生股份有限公司 | Polymeric liquid crystal composition |
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| US6136225A (en) * | 1995-09-01 | 2000-10-24 | Basf Aktiengesellschaft | Polymerizable liquid-crystalline compounds |
| JP2003193053A (en) * | 2001-12-26 | 2003-07-09 | Dainippon Ink & Chem Inc | Polymerizable liquid crystal composition and optical anisotropic object using the same |
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Address after: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Address before: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Patentee before: Jiangsu Hecheng Display Technology Co.,Ltd. |
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Address after: 2/F, Sino Japan Cooperation Innovation Park, No. 16 Zidan Road, Qinhuai District, Nanjing, Jiangsu Province, 210014 Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Address before: 212212 East Side of Yangzhong Yangtze River Bridge, Zhenjiang City, Jiangsu Province Patentee before: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. |
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