CN105885871B - A kind of polymerizable liquid crystal compound - Google Patents
A kind of polymerizable liquid crystal compound Download PDFInfo
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- CN105885871B CN105885871B CN201610104896.7A CN201610104896A CN105885871B CN 105885871 B CN105885871 B CN 105885871B CN 201610104896 A CN201610104896 A CN 201610104896A CN 105885871 B CN105885871 B CN 105885871B
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0455—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2CF2-, -CF2CF2CF2CF2- or -CH2CF2CF2CH2- chain
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
- C09K2019/181—Ph-C≡C-Ph
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K2019/2078—Ph-COO-Ph-COO-Ph
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3009—Cy-Ph
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Abstract
The present invention provides a kind of polymerizable liquid crystal compound, it includes the difunctional polymerisable liquid crystal compound that at least one general formula I represents；The simple function group polymerisable liquid crystal compound that at least one general formula II represents；And the fluorine-containing polymerisable liquid crystal compound that at least one general formula III represents.Polymerizable liquid crystal compound provided by the invention, have the advantages that can room temperature coating, surface energy is low, fine and close and corrosion resistance is strong after easy to clean, surface cure, can be used for special optical film field.
Description
Technical field
A kind of application the present invention relates to polymerizable liquid crystal compound and its in optical film.
Background technology
In the preparation process of optical film, surface treatment is always the object of research of concern.Such as PET base material
Cured film, it is different according to the application used, by various forms of processing, there can be different application characteristics, such as have anti-
The characteristics such as reflection, anti-mapping, anti-interference, antifouling, anti-fingerprint, antistatic, release, UV filterings and IR filterings.
In the optics film production of polymerisable liquid crystal, since it is desired that special optical effect, and examined for yield
Consider, optical film can not be directly formed on optics.During optical film is fabricated separately, it is often necessary to carry out surface guarantor
Shield, prevents the pollution of fingerprint, dust and greasy dirt, in order to reuse.
In antifouling anti-fingerprint application field, the fluorine-containing coating of common use or fluorine silicon cladding carry out protection processing, by
There is low surface energy in fluorine-containing coating or fluorine silicon cladding, largely used in optical film field.
However, originally to the polymerisable liquid crystal optical film field of optical dimensions precision, additional one layer of plated film into
Row protection, not only increases the process complexity of production, while the uneven thickness of additional coating, directly affects optical film entirety
Quality.
It is accordingly required in particular to a kind of optics film formulation of the easy convenient coating construction stablized, obtain excellent antifouling anti-
Fingerprint optical film.
The content of the invention
The present invention goal of the invention be to provide a kind of polymerizable liquid crystal composition, have can room temperature coating, surface energy it is low, hold
The advantages that fine and close and corrosion resistance is strong after easy cleaning, surface cure, can be used for special optical film field.
In order to reach foregoing invention purpose, the present invention provides a kind of polymerizable liquid crystal compound, the polymerizable liquid crystal group
Compound includes：
At least one difunctional polymerisable liquid crystal compound；
At least one simple function group polymerisable liquid crystal compound；And
At least one fluorine-containing polymerisable liquid crystal compound.
In embodiments of the invention, the difunctional polymerisable liquid crystal compound accounts for the polymerizable liquid crystal combination
The 40-99% of thing gross weight；The simple function group polymerisable liquid crystal compound accounts for the polymerizable liquid crystal compound gross weight
1-60%；And the fluorine-containing polymerisable liquid crystal compound accounts for the 0.1-5% of the polymerizable liquid crystal compound gross weight.
In embodiments of the invention, the difunctional polymerisable liquid crystal compound is the compound that general formula I represents：
Wherein,
A and B are identical or different, represent hydrogen or methyl independently of one another；
Sp1And Sp2It is identical or different, the alkyl chain of 1-11 carbon is represented independently of one another；
Z1、Z2、Z3And Z4It is identical or different, expression-O- ,-CO- ,-OCO- ,-COO- or-OCOO- independently of one another；
R represents methyl or halogen；
M represents 0 or 1.
In embodiments of the invention, preferably described Sp1And Sp2It is identical or different, 3-7 carbon is represented independently of one another
Alkyl chain；The Z1、Z2、Z3And Z4It is identical or different, expression-O- ,-OCO- ,-COO- or-OCOO- independently of one another；It is described
R represents methyl or F.
In embodiments of the invention, more preferably, the Z1And Z4It is identical or different, independently of one another expression-O- or-
OCOO-；The Z2And Z3It is identical or different, expression-OCO- or-COO- independently of one another；The R represents methyl.
In embodiments of the invention, the compound of preferably described general formula I is selected from the group of following compound composition：
With
And
As particularly preferred scheme, the compound of the general formula I is one or more in the group that following compound forms
Compound：
With
And
In embodiments of the invention, the compound of preferably described general formula I accounts for the polymerizable liquid crystal compound gross weight
The 45-90% of amount.
In embodiments of the invention, monoiunctional polymerizable's liquid-crystal compounds is the compound that general formula II represents：
Wherein,
AS represents hydrogen or methyl；
L and Rd are identical or different, represent the alkyl chain of 1-11 carbon independently of one another；
Z5And Z6It is identical or different, independently of one another represent singly-bound ,-C=C-,-O-、-CO-、-OCO-、-
COO- or-OCOO-；
Represent phenylene or cyclohexyl；
X represents singly-bound ,-O- ,-OCO- ,-COO- or-OCOO-；
N represents 0 or 1.
In embodiments of the invention, preferably described L represents the alkyl chain of 3-7 carbon；The Z5And Z6It is identical or not
Together, independently of one another represent singly-bound orThe X represents singly-bound or-O-.
In embodiments of the invention, the compound of preferably described general formula II is selected from the group of following compound composition：
And
As particularly preferred scheme, the compound of the general formula II is one or more in the group that following compound forms
Compound：
And
In embodiments of the invention, the compound of preferably described general formula II accounts for the liquid-crystal composition gross weight
10-50%.
In embodiments of the invention, the fluorine-containing polymerizable compound is the compound that general formula III represents：
Wherein,
AF represents hydrogen or methyl；
CF represents the fluoro-containing group of non-benzene ring structure.
In embodiments of the invention, the compound of preferably described general formula III accounts for the liquid-crystal composition gross weight
0.1-2%.
In embodiments of the invention, had no particular limits for fluorine-containing polymerizable compound, monomer can be used,
Prepolymer can also be used, the fluorine-containing polymerizable compound can form miscible system with polymerisable liquid crystal.To fluorine-containing chemical combination
The number of functional groups of thing has no particular limits, it is preferred to use the fluorine-containing polymerizability compound of difunctional.
In embodiments of the invention, the compound of preferably described general formula III is the group of following compound composition：
With
And
As particularly preferred scheme, the compound of the general formula III is one or more in the group that following compound forms
Compound：
And
In embodiments of the invention, more preferably, the generalformulaⅰcompound accounts for the polymerizable liquid crystal compound gross weight
The 45-70% of amount；The compound of the general formula II accounts for the 30-50% of the polymerizable liquid crystal compound gross weight；It is and described
The compound of general formula III accounts for the 0.5-2% of the polymerizable liquid crystal compound gross weight.
As particularly preferred scheme, the 49-66% of liquid-crystal composition gross weight described in the compound station of the general formula I；Institute
The compound for stating general formula II accounts for the 33-49.5% of the liquid-crystal composition gross weight；And the compound of the general formula III accounts for institute
State the 0.5-2% of liquid-crystal composition gross weight.
The present invention also provides comprising above-mentioned polymerizable liquid crystal compound the application in special optical film is prepared.
Beneficial effect：The present invention is screened by many experiments, preferably obtains the poly- of optimum structure composition and specified weight ratio
Conjunction property liquid-crystal composition, each component proportioning is scientific and reasonable, and coating is easy for construction, have can room temperature coating, surface energy it is low, easily clear
Wash, the advantages that fine and close after surface cure and corrosion resistance is strong, excellent antifouling anti-fingerprint optical film can be obtained, can extensively hair in
Special optical film field, compared to the prior art, achieves good technological progress.
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.
Embodiment 1
The polymerizable liquid crystal compound for including following structural compounds is prepared, it is as shown in table 1 below：
1 polymerizable liquid crystal compound formula of table
Embodiment 2
The polymerizable liquid crystal compound for including following structural compounds is prepared, it is as shown in table 2 below：
2 polymerizable liquid crystal compound formula of table
Embodiment 3
The polymerizable liquid crystal compound for including following structural compounds is prepared, it is as shown in table 3 below：
3 polymerizable liquid crystal compound formula of table
Embodiment 4
The polymerizable liquid crystal compound for including following structural compounds is prepared, it is as shown in table 4 below：
4 polymerizable liquid crystal compound formula of table
The polymerizable liquid crystal formula that the embodiment of the present invention 1, embodiment 2, embodiment 3 and embodiment 4 provide is applied to
On substrate film, corresponding performance test is carried out.Substrate film has no particular limits, and can use common PET, TAC etc.
Ordinary optical film.Using conventional ultraviolet curing process after coating, irradiated under the ultraviolet light of 365nm, normal temperature cure obtains light
Film is learned, hardening time is 60 seconds.
Anti-fingerprint pollutant performance test is carried out after the completion of curing, which can be characterized by surface energy.Because refer to
The main component of line, that is, human sweat is water and various greases, with this according to the pure water and hexadecane for measuring hardening film surface
Contact angle characterizes surface energy.As shown in the table, film top layer of the invention and the static contact angle of water are at least 90 °, and just
The contact angle of hexadecane is at least 50 °.It is highly preferred that it is at least 100 ° with the static contact angle of water, the contact with hexadecane
Angle is at least 60 °, shows that polymerizable liquid crystal compound provided by the invention can obtain excellent antifouling anti-fingerprint optical film, obtains
Obvious technological progress.
Surface energy characteristic features are as follows：
| Embodiment | Pure water contact angle (°) | Hexadecane contact angle (°) |
| Embodiment 1 | 105 | 64 |
| Embodiment 2 | 106 | 67 |
| Embodiment 3 | 101 | 58 |
| Embodiment 4 | 104 | 61 |
Claims (6)
1. a kind of polymerizable liquid crystal compound, it is characterised in that it includes：
At least one difunctional polymerisable liquid crystal compound；
At least one simple function group polymerisable liquid crystal compound；And
At least one fluorine-containing polymerisable liquid crystal compound；
The difunctional polymerisable liquid crystal compound is the compound that general formula I represents：
Wherein,
A and B are identical or different, represent hydrogen or methyl independently of one another；
Sp1And Sp2It is identical or different, the alkyl chain of 1-11 carbon is represented independently of one another；
Z1、Z2、Z3And Z4It is identical or different, expression-O- ,-CO- ,-OCO- ,-COO- or-OCOO- independently of one another；
R represents methyl or halogen；
M represents 0 or 1；
Monoiunctional polymerizable's liquid-crystal compounds is the compound that general formula II represents：
Wherein,
AS represents hydrogen or methyl；
L and Rd are identical or different, represent the alkyl chain of 1-11 carbon independently of one another；
Z5And Z6It is identical or different, independently of one another represent singly-bound ,-C=C-,- O- ,-CO- ,-OCO- ,-COO- or-
OCOO-；
Represent phenylene or cyclohexyl；
X represents singly-bound ,-O- ,-OCO- ,-COO- or-OCOO-；
N represents 0 or 1；
The fluorine-containing polymerizable compound is the compound that general formula III represents：
Wherein,
AF represents hydrogen or methyl；
CF represents the fluoro-containing group of non-benzene ring structure；
The difunctional polymerisable liquid crystal compound accounts for the 40-99% of the polymerizable liquid crystal compound gross weight；The list
Functional group's polymerisable liquid crystal compound accounts for the 1-60% of the polymerizable liquid crystal compound gross weight；It is and described fluorine-containing polymerizable
Liquid-crystal compounds accounts for the 0.1-5% of the polymerizable liquid crystal compound gross weight.
2. polymerizable liquid crystal compound according to claim 1, it is characterised in that the Sp1And Sp2It is identical or different, respectively
From the alkyl chain for independently representing 3-7 carbon；The Z1And Z4It is identical or different, expression-O- or-OCOO- independently of one another；Institute
State Z2And Z3It is identical or different, expression-OCO- or-COO- independently of one another；The R represents methyl.
3. polymerizable liquid crystal compound according to claim 1, it is characterised in that the L represents the alkyl of 3-7 carbon
Chain；The Z5And Z6It is identical or different, independently of one another represent singly-bound orThe X represents singly-bound or-O-.
4. polymerizable liquid crystal compound according to claim 1, it is characterised in that the compound of the general formula I accounts for described
The 49-66% of polymerizable liquid crystal compound gross weight；The compound of the general formula II accounts for the polymerizable liquid crystal compound gross weight
The 33-49.5% of amount；And the compound of the general formula III accounts for the 0.5-2% of the polymerizable liquid crystal compound gross weight.
5. polymerizable liquid crystal compound according to claim 1, it is characterised in that the liquid-crystal composition includes：
Account for the chemical compounds I -9 of the liquid-crystal composition gross weight 24.75%；
Account for the chemical compounds I -3 of the liquid-crystal composition gross weight 24.75%；
Account for the compound ii -1 of the liquid-crystal composition gross weight 24.75%；
Account for the compound ii -6 of the liquid-crystal composition gross weight 24.75%；And
Compound III -1 of the liquid-crystal composition gross weight 1% is accounted for,
Or the liquid-crystal composition includes：
Account for the chemical compounds I -9 of the liquid-crystal composition gross weight 33%；
Account for the chemical compounds I -3 of the liquid-crystal composition gross weight 33%；
Account for the compound ii -1 of the liquid-crystal composition gross weight 33%；And
Compound III -1 of the liquid-crystal composition gross weight 1% is accounted for,
Or the liquid-crystal composition includes：
Account for the chemical compounds I -9 of the liquid-crystal composition gross weight 29.5%；
Account for the chemical compounds I -3 of the liquid-crystal composition gross weight 30%；
Account for the compound ii -1 of the liquid-crystal composition gross weight 20%；
Account for the compound ii -6 of the liquid-crystal composition gross weight 20%；And
Compound III -2 of the liquid-crystal composition gross weight 0.5% are accounted for,
Or the liquid-crystal composition includes：
Account for the chemical compounds I -9 of the liquid-crystal composition gross weight 24.5%；
Account for the chemical compounds I -3 of the liquid-crystal composition gross weight 24.5%；
Account for the compound ii -1 of the liquid-crystal composition gross weight 24.5%；
Account for the compound ii -6 of the liquid-crystal composition gross weight 24.5%；And
Account for the compound III -4 of the liquid-crystal composition gross weight 2%；
The structural formula of chemical compounds I -9 is：
The structural formula of chemical compounds I -3 is：
The structural formula of compound ii -1 is：
The structural formula of compound ii -6 is：
：
The structural formula of compound III -1 is：
The structural formula of compound III -2 is：
The structural formula of compound III -4 is：
6. application of the claim 1-5 any one of them polymerizable liquid crystal compounds in optical film is prepared.
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| CN115322795A (en) * | 2021-12-29 | 2022-11-11 | 上海先认新材料合伙企业(有限合伙) | Liquid crystal composition and application thereof |
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