CN109913240B - Polymerizable liquid crystal composition and use thereof - Google Patents
Polymerizable liquid crystal composition and use thereof Download PDFInfo
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Abstract
The present invention provides an optically anisotropic polymerizable liquid crystal composition comprising at least one polymerizable liquid crystal compound of the general formula i. The invention also provides application of the polymerizable liquid crystal composition in an optical film. The polymerizable liquid crystal composition disclosed by the invention keeps a nematic phase in a wider temperature range covering normal temperature, has higher optical anisotropy, has alignment capability and simultaneously keeps fluidity, so that a coating process can be carried out at lower temperature according to requirements, and can be operated at relatively lower temperature under the condition of no solvent, and the damage of a polymerizable compound caused by high temperature in the coating process can be effectively avoided or remarkably reduced; meanwhile, the process temperature is controlled at a relatively low temperature, preferably normal temperature, so that energy conservation, emission reduction, safety and environmental protection are facilitated, and the optical functional film with excellent performance is obtained.
Description
Technical Field
The invention relates to the field of liquid crystal materials, in particular to an optically anisotropic polymerizable liquid crystal composition and application thereof in an optical film.
Background
In recent years, with the development of information-oriented society, simple liquid crystal displays have not been able to satisfy the demand of people for display, and there is a need to use optically anisotropic bodies of various functions to help improve the quality of display. The polymerizable liquid crystal has the properties of both liquid crystal and light curing material, can fix the liquid crystal property in the optical film through ultraviolet radiation, expands the application field of the liquid crystal, and plays a unique role in the anisotropic optical film.
In the prior art, a polymerizable part in polymerizable liquid crystal is mostly composed of an acrylate structure, under the irradiation of ultraviolet light, double bonds of the acrylate part can be opened to form free radicals, and the free radicals are polymerized to form macromolecules. When the acrylic ester is heated to a certain temperature, ultraviolet irradiation is not needed, the double bond of the acrylic ester can be initiated to be opened only by heat, and free radical polymerization can be initiated to form a macromolecule. The method only adopts a heating mode for heat curing, and the high temperature can cause other bonds of the polymerizable liquid crystal to be broken, further damage the liquid crystal structure and cause the performance reduction of the formed optical film, so that the existing polymerizable liquid crystal monomer still has a plurality of defects, such as the high melting point of the polymerizable liquid crystal monomer in US6136225, the actual construction temperature is as high as 80-90 ℃, the energy consumption is greatly increased, and the defects of uneven alignment, abnormal polymerization and the like are easily caused at high temperature.
Most of the polymerizable liquid crystals are solid, and in order to retain the liquid crystal properties of the polymerizable liquid crystals after curing, it is necessary to heat the polymerizable liquid crystals to a liquid crystal phase temperature and perform ultraviolet curing or thermal curing at the liquid crystal phase temperature. When heated to the liquid crystal phase temperature, the thermally initiated free radicals begin to initiate polymerization of the polymerizable liquid crystal moieties. In order to retain the liquid crystal properties of the polymerizable liquid crystal, it must be heated to a higher temperature, which tends to cause the liquid crystal to break other bonds under the action of heat, and to begin to undergo a thermally-initiated polymerization phenomenon before the desired liquid crystal phase temperature has been reached, resulting in poor optical film properties.
In order to overcome the defects of thermal initiation polymerization, ultraviolet irradiation polymerization is mostly adopted in common polymerizable liquid crystals, so that the defects caused by thermal initiation are effectively avoided. However, the disadvantage of thermally initiated polymerization cannot be completely avoided because the liquid crystal phase temperature is too high. Therefore, there is a need for a polymerizable liquid crystal composition that can be applied at a relatively low temperature and can maintain a nematic phase at normal temperature.
Disclosure of Invention
The purpose of the invention is as follows: in view of the drawbacks of the prior art, the present invention provides a polymerizable liquid crystal composition that maintains a nematic phase and has high optical anisotropy in a wide temperature range covering normal temperature, maintains fluidity while having alignment ability, allows a coating process to be performed at a low temperature as required, and can be operated at a relatively low temperature without a solvent, and effectively avoids or significantly reduces damage of a polymerizable compound due to high temperature during the coating process; meanwhile, the process temperature is controlled at a relatively low temperature, preferably normal temperature, so that energy conservation, emission reduction, safety and environmental protection are facilitated, and the optical functional film with excellent performance is obtained.
The technical scheme of the invention is as follows:
in order to achieve the above object, the present invention provides an optically anisotropic polymerizable liquid crystal composition comprising:
at least one polymerizable liquid-crystalline compound of the formula I
Wherein the content of the first and second substances,
the Sp1And Sp2The same or different, each independently represents a single bond or an alkyl or alkoxy or alkoxycarbonyl group having 1 to 18 carbon atoms, wherein one or more-CH groups in the alkyl, alkoxy or alkoxycarbonyl group2-may be replaced by-O-or-C ═ O-, with the proviso that oxygen atoms are not directly attached;
said X1And X2The same or different, each independently represent-H or-CH3；
Said L1、L2、L3And L4The same or different, each independently represent-H, -F, -CH3or-OCH3；
Z is1Or Z2The same or different, each independently represent-CH2O-、-OCH2-、-CH2CH2-, -COO-, -OCO-or a single bond;
the ring
Are the same or different and each independently represents
Wherein
One or more of-H on (a) may be replaced by-F, -CH3or-OCH3Substitution;
n represents 0, 1 or 2.
In some embodiments of the present invention, the polymerizable liquid crystal compound of formula I is preferably selected from the group consisting of compounds of formulae I-1 to I-2:
in some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 30% to 100% of the polymerizable liquid crystal compound of formula i.
In some embodiments of the present invention, the polymerizable liquid crystal compound of formula I comprises at least one compound of formula I-1:
in some embodiments of the invention, the compound of formula I-1 is selected from the group consisting of:
wherein said Y is1Independently represent-F, -CH3or-OCH3。
In some embodiments of the present invention, the polymerizable liquid crystal compound of formula I comprises at least one compound of formula I-2:
in some embodiments of the invention, the compound of formula I-2 is selected from the group consisting of:
wherein said R1、R2And R3The same or different, each independently represent-F, -CH3or-OCH3。
In some embodiments of the invention, said Sp1represents-O (CH)2)m-、-OOCO(CH2)a-、-(CH2)b-or a single bond, wherein m, a and b each independently represent a positive integer from 1 to 16, wherein the oxygen atom is attached to the ring structure.
In some embodiments of the invention, said Sp2represents-O (CH)2)m-、-OOCO(CH2)a-、-(CH2)b-or a single bond, wherein m, a and b each independently represent a positive integer from 1 to 16, wherein the oxygen atom is attached to the ring structure.
In some embodiments of the invention, said Sp1represents-O (CH)2)m-, said Sp2represents-OOCO (CH)2)a-. In some implementations of the inventionIn scheme (I), the Sp1represents-OOCO (CH)2)a-, said Sp2represents-O (CH)2)m-or- (CH)2)b-. In some embodiments of the invention, said Sp1And Sp2Each independently represents-O (CH)2)m-. In some embodiments of the invention, said Sp1Is represented by- (CH)2)b-, said Sp2represents-O (CH)2)m-。
In some embodiments of the invention, said Sp1And Sp2Each independently represents-OOCO (CH)2)a-. In some embodiments of the invention, said Sp1And Sp2Each independently represents- (CH)2)b-. In some embodiments of the invention, said Sp1And Sp2All represent single bonds. In some embodiments of the invention, said Sp1And Sp2In which only one is a single bond and the other is-O (CH)2)m-、-OOCO(CH2)a-or- (CH)2)b-。
In some embodiments of the invention, Sp in formula I-1-21And Sp2Each independently represents- (CH)2)b-; or each independently represents-O (CH)2)m-; or both represent a single bond; or the said Sp1Is represented by- (CH)2)b-, said Sp2represents-O (CH)2)m-; or the said Sp2Is represented by- (CH)2)b-, said Sp1represents-O (CH)2)m-; wherein Y is1preferably-CH3or-F.
In some embodiments of the invention, Sp in formula I-1-5, I-1-6, I-1-7, I-1-8, I-1-9, I-1-10, or I-1-111And Sp2Each independently represents- (CH)2)b-; or each independently represents-O (CH)2)m-; or Sp1Is represented by- (CH)2)b-，Sp2represents-O (CH)2)m-; or Sp2Is represented by- (CH)2)b-，Sp1represents-O (CH)2)m-。
In some embodiments of the invention, Sp in formula I-1-141And Sp2Each independently represents-OOCO (CH)2)a-; or each independently represents-O (CH)2)m-; or Sp1represents-OOCO (CH)2)a-，Sp2represents-O (CH)2)m-; or Sp2represents-OOCO (CH)2)a-，Sp1represents-O (CH)2)m-。
In some embodiments of the invention, Sp in formula I-2-11And Sp2Each independently represents- (CH)2)b-; or Sp1Is represented by- (CH)2)b-，Sp2represents-O (CH)2)m-。
In some embodiments of the invention, Sp in said formula I-2-2 or I-2-31And Sp2Each independently represents- (CH)2)b-; or Sp1Is represented by- (CH)2)b-，Sp2represents-O (CH)2)m-; or Sp2Is represented by- (CH)2)b-，Sp1represents-O (CH)2)m-。
In some embodiments of the invention, Sp in formula I-2-4, I-2-5, I-2-6, I-2-7, I-2-8, I-2-9, or I-2-101And Sp2Each independently represents- (CH)2)b-; or Sp1Is represented by- (CH)2)b-，Sp2represents-O (CH)2)m-; or Sp1And Sp2All represent a single bond; or Sp2Is represented by- (CH)2)b-，Sp1represents-O (CH)2)m-。
In some embodiments of the invention, m, a and b represent positive integers from 1 to 16 and are at Sp1And Sp2Wherein m, a and b may represent different positive integers, whichThe central oxygen atom is attached to a ring structure.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 30% to 90% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the polymerizable liquid crystal composition comprises 30% to 85% of the polymerizable liquid crystal compound of formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 30% to 80% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 35% to 80% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 35% to 90% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 35% to 85% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 40% to 90% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 40% to 80% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 45% to 90% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 45% to 80% of the polymerizable liquid crystal compound of the general formula I-1.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 10% to 70% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 10% to 65% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 10% to 60% of the polymerizable liquid crystal compound represented by the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 10% to 55% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 20% to 55% of the polymerizable liquid crystal compound represented by the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 15% to 65% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 15% to 70% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 20% to 70% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 20% to 65% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 20% to 60% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the optically anisotropic polymerizable liquid crystal composition comprises 20% to 55% of the polymerizable liquid crystal compound of the general formula I-2.
In some embodiments of the present invention, the compound of formula I-1 is preferably selected from the group consisting of formula I-1-2, formula I-1-5, formula I-1-6, formula I-1-7, formula I-1-8, formula I-1-9, and formula I-1-14.
In some embodiments of the present invention, the compound of formula I-2 is preferably selected from the group consisting of formula I-2-1, formula I-2-4, formula I-2-5, formula I-2-6, formula I-2-7, and formula I-2-10.
The optically anisotropic polymerizable liquid crystal composition of the present invention has an optical anisotropy in a range of 0.01 to 0.5, preferably 0.03 to 0.35, more preferably 0.05 to 0.25, more preferably 0.09 to 0.25, more preferably 0.10 to 0.25, and more preferably 0.12 to 0.25.
The invention also provides an application of the optically anisotropic polymerizable liquid crystal composition in an optical film.
Has the advantages that:
in the prior art, there are two general coating methods: one is to heat and melt a polymerizable liquid crystal composition and then coat the composition, usually at a temperature of 80 ℃ or higher; the other method is to dissolve the polymerizable liquid crystal composition in an organic solvent, coat the solution, and then heat and evaporate the organic solvent, wherein the temperature for evaporation is usually 80 ℃ or higher; at a high temperature such as 80 ℃, the structure of the acrylate is easily broken, and for example, thermal polymerization occurs, which results in coating abnormality.
The invention provides a polymerizable liquid crystal composition containing the polymerizable liquid crystal compound shown in the general formula I, which can keep a nematic phase in a wider temperature range covering normal temperature (for example, the nematic phase is kept in a range of 0-90 ℃) and has higher optical anisotropy, has alignment capability and keeps fluidity, enables a coating process to be carried out at lower temperature (for example, below 50 ℃ or directly at the normal temperature of 22-27 ℃) according to requirements, can be operated at relatively lower temperature under the condition of no solvent, and can effectively avoid or remarkably reduce the damage of the polymerizable compound caused by high temperature in the coating process; meanwhile, the process temperature is controlled at a relatively low temperature, preferably normal temperature, so that energy conservation, emission reduction, safety and environmental protection are facilitated, and the optical functional film with excellent performance is obtained.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
For convenience of expression, in the following examples, the group structure of the polymerizable liquid crystal compound is represented by the code listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
structural formula 1:
the formula 1, as represented by the code listed in Table 1, can be expressed as: VE4OEPEP (1) EPEO4 EV;
structural formula 2:
the formula 2, as represented by the code listed in Table 1, can be expressed as: v (1) E6C2GP3EV (1);
structural formula 3:
the formula 3, as represented by the code listed in Table 1, can be expressed as: VE3CC2 EV.
The abbreviated codes of the test items in the following examples are as follows:
TN→Iclearing Point (nematic-isotropic phase transition temperature, degree C.)
TS→NLow temperature transformation Point (smectic-nematic transition temperature, deg.C.)
Δ n optical anisotropy (589nm, 20 ℃ C.)
Temperature range of T nematic phase (. degree.C.)
Wherein the content of the first and second substances,
the optical anisotropy is measured by an Abbe refractometer under a sodium lamp (589nm) light source at 25 ℃;
nematic phase temperature range T ═ TN→I～TS→N。
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Example 1
The polymerizable liquid crystal composition of example 1 was prepared with the compounds and weight percentages listed in table 2, and the test data are as follows:
TABLE 2 polymerizable liquid Crystal composition formulations
| Component code | Weight of hundredRatio of division |
| VE3PP3EV | 15 |
| VE3PP2EV | 10 |
| VE4OEPEP(1)EPEO4EV | 40 |
| VE3OPEP(1)EPO3EV | 15 |
| VE6OPEP(1)EPO6EV | 15 |
| VE4OPEP(1)EPO4EV | 5 |
| Total up to | 100 |
Performance parameter test results: t is 12-65 ℃.
Example 2
The polymerizable liquid crystal composition of example 2 was prepared with the compounds and weight percentages listed in table 3, and the test data are as follows:
TABLE 3 polymerizable liquid Crystal composition formulations
| Component code | Weight percent of |
| VE3PP3EV | 15 |
| VE3PP2EV | 10 |
| VE4OPEP(1)EPO4EV | 5 |
| VE4OEPEP(1)EPEO4EV | 36 |
| VE3OPEP(1)EPO3EV | 13 |
| VE6OPEP(1)EPO6EV | 13 |
| VE1C2PPO6EV | 8 |
| Total up to | 100 |
The performance parameter test results are as follows: t is 10-61 ℃.
Example 3
The polymerizable liquid crystal composition of example 3 was prepared with the compounds and weight percentages listed in table 4, and the test data are as follows:
TABLE 4 polymerizable liquid Crystal composition formulations
And (3) performance test results: t is 14-51 ℃.
Example 4
The polymerizable liquid crystal composition of example 4 was prepared with the compounds and weight percentages listed in table 5, and the test data are as follows:
TABLE 5 polymerizable liquid Crystal composition formulations
| Component code | Weight percent of |
| VE4OEPEP(1)EPEO4EV | 28 |
| VE3OPEP(1)EPO3EV | 8 |
| VE6OPEP(1)EPO6EV | 8 |
| VE4OPEP(1)EPO4EV | 5 |
| VE4OPPO4EV | 3 |
| VE6OPPO6EV | 3 |
| VE3PP3EV | 12 |
| VE3PP2EV | 10 |
| VE3CC3EV | 8 |
| VE3CC5EV | 5 |
| VE3CC2EV | 10 |
| Total up to | 100 |
And (3) performance test results: t is 7-43 ℃.
Example 5
The polymerizable liquid crystal composition of example 5 was prepared with the compounds and weight percentages listed in Table 6, and the test data are as follows:
TABLE 6 polymerizable liquid Crystal composition formulations
| Component code | Weight percent of |
| VE3PGP3EV | 10 |
| VE1CC2PO3EV | 10 |
| V(1)E6C2PPO3EV(1) | 10 |
| V(1)E6C2GP3EV(1) | 10 |
| VE3C2CP3EV | 10 |
| VE3C2CPO3EV | 10 |
| VE3CC1OP3EV | 10 |
| VE1C1OPPO6EV | 10 |
| VE3PP3EV | 6 |
| VE3PP2EV | 6 |
| VE3CC3EV | 4 |
| VE3CC2EV | 4 |
| Total up to | 100 |
And (3) performance test results: t is 22-40 ℃.
Example 6
The polymerizable liquid crystal composition of example 6 was prepared with the compounds and weight percentages listed in Table 7, and the test data are as follows:
TABLE 7 polymerizable liquid Crystal composition formulations
| Component code | Weight percent of |
| VE4OEPEP(1)EPEO4EV | 33 |
| VE3OPEP(1)EPO3EV | 33 |
| VEPC3 | 24 |
| VE3PP3EV | 10 |
| Total up to | 100 |
The performance detection result is as follows: t is 15-89 ℃.
Example 7
The optically anisotropic polymerizable liquid crystal composition of example 1 was coated on a horizontally aligned glass surface at 35 ℃ and then polymerized by irradiation with a UV lamp (light intensity: 45mw) to obtain an optically anisotropic film, which was tested to have an optical anisotropy Δ n of 0.135.
As can be seen from the above examples 1 to 7, the polymerizable liquid crystal composition of the present invention has a relatively suitable nematic phase temperature and a relatively high optical anisotropy, maintains a nematic phase within a relatively wide temperature range covering normal temperature, maintains fluidity while having alignment ability, allows a coating process to be performed at a relatively low temperature as required, and can be operated at a relatively low temperature without a solvent, thereby effectively avoiding or significantly reducing damage of a polymerizable compound due to high temperature during the coating process; meanwhile, the process temperature is controlled at a relatively low temperature, preferably normal temperature, so that energy conservation, emission reduction, safety and environmental protection are facilitated, and the optical functional film with excellent performance is obtained.
Claims (2)
1. An optically anisotropic polymerizable liquid crystal composition comprising:
at least one compound selected from the group consisting of compounds of the general formulae I-1-1 to I-1-14:
at least one compound selected from the group consisting of compounds of the general formulae I-2-1 to I-2-10:
wherein the content of the first and second substances,
the Sp1And Sp2Each independently represents-OOCO (CH)2)a-or- (CH)2)bWherein a and b each independently represent a positive integer of 1 to 16 in which an oxygen atom is bonded to a ring structure;
said X1And X2The same or different, each independently represent-H or-CH3；
Said L1、L2And L3The same or different, each independently represent-H-F、-CH3or-OCH3；
Wherein said Y is1represents-F, -CH3or-OCH3；
Wherein said R1、R2And R3The same or different, each independently represent-F, -CH3or-OCH3；
The optically anisotropic polymerizable liquid crystal composition comprises 30% -90% of the polymerizable liquid crystal compound with the general formula I-1-1 to I-1-14;
the optically anisotropic polymerizable liquid crystal composition contains 10% -70% of the polymerizable liquid crystal compound of the general formula I-2-1 to I-2-10.
2. Use of the optically anisotropic polymerizable liquid crystal composition according to claim 1 in an optical film.
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| CN109913240A (en) | 2019-06-21 |
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