CN117024657B - Holographic polymer dispersed liquid crystal material and application thereof - Google Patents
Holographic polymer dispersed liquid crystal material and application thereof Download PDFInfo
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- CN117024657B CN117024657B CN202311278087.4A CN202311278087A CN117024657B CN 117024657 B CN117024657 B CN 117024657B CN 202311278087 A CN202311278087 A CN 202311278087A CN 117024657 B CN117024657 B CN 117024657B
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- 239000005276 holographic polymer dispersed liquid crystals (HPDLCs) Substances 0.000 title claims abstract description 76
- 239000000463 material Substances 0.000 title claims abstract description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 43
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000003999 initiator Substances 0.000 claims abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical group OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical group O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 claims description 3
- 229930187593 rose bengal Natural products 0.000 claims description 3
- 229940081623 rose bengal Drugs 0.000 claims description 3
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 abstract description 9
- -1 acrylic ester Chemical class 0.000 abstract description 8
- 230000000052 comparative effect Effects 0.000 description 17
- 239000011521 glass Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 230000003190 augmentative effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- JZEXORLUKMQOFA-UHFFFAOYSA-N 2-(1-ethoxyethyl)-2-(hydroxymethyl)propane-1,3-diol prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCOC(C)C(CO)(CO)CO JZEXORLUKMQOFA-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3895—Polymers with mesogenic groups in the side chain containing two or more mesogenic groups per monomer unit, e.g. polyitaconates, polymaleates
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/01—Head-up displays
- G02B27/0101—Head-up displays characterised by optical features
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/01—Head-up displays
- G02B27/0101—Head-up displays characterised by optical features
- G02B27/0103—Head-up displays characterised by optical features comprising holographic elements
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/01—Head-up displays
- G02B27/017—Head mounted
- G02B27/0172—Head mounted characterised by optical features
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
- G03H1/0005—Adaptation of holography to specific applications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/01—Head-up displays
- G02B27/017—Head mounted
- G02B27/0172—Head mounted characterised by optical features
- G02B2027/0174—Head mounted characterised by optical features holographic
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
- G03H1/0005—Adaptation of holography to specific applications
- G03H2001/0088—Adaptation of holography to specific applications for video-holography, i.e. integrating hologram acquisition, transmission and display
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
Abstract
The invention discloses a holographic polymer dispersed liquid crystal material and application thereof, wherein the holographic polymer dispersed liquid crystal material comprises a liquid crystal composition, acrylic ester polymerizable monomers, a photoinitiator and a co-initiator; the liquid crystal composition comprises compounds shown in the following formulas I-III, and the acrylic polymerizable monomer comprises a trifunctional polymerizable monomer and a compound shown in the following formula IV. According to the holographic polymer dispersed liquid crystal material, the liquid crystal composition with a specific structural formula and the polymerizable monomer are selected, so that the prepared holographic polymer dispersed liquid crystal material has excellent performance, and the prepared volume holographic grating has high diffraction efficiency and low haze, can be switched between a holographic state and a transparent state, and can meet the application requirements of the volume holographic optical waveguide.
Description
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a holographic polymer dispersed liquid crystal material and application thereof.
Background
Augmented Reality (AR) is a new technology of superimposing real world information and virtual world information in real time to the same picture or space. The prompting information, the virtual object or the virtual scene is generated through the computer and is overlapped in the real world to be perceived by human organs, so that the sense experience of augmented reality is achieved. AR technology is now widely used in the fields of gaming, retail, education, industry, military, and medical.
Waveguide technologies for fabricating ARs are currently divided into three categories: array optical waveguide, surface relief optical waveguide, volume holographic optical waveguide, wherein the volume holographic optical waveguide technology is widely paid attention to at home and abroad due to the advantages of lower cost, suitability for large-scale production and the like.
The holographic polymer dispersed liquid crystal (Holographic polymer dispersed liquid crystal, HPDLC) is a novel holographic material, has the outstanding advantages of low cost, simple manufacturing process, high diffraction efficiency, low haze and the like, and because the liquid crystal material has double refraction, can induce an electric field and can be switched between no and ne, an electric signal can be used for tuning a grating, a large difference value exists between the refractive index of the liquid crystal and the polymer when no voltage is applied, the device presents a holographic state, when the voltage is applied, the liquid crystal deflects, the refractive index of the liquid crystal is similar to that of the polymer, the device does not present the holographic state any more, and the double refractive index of a liquid crystal medium which can be provided on the market at present is still lower, and the requirements of liquid crystal products such as a liquid crystal lens and the like cannot be met.
The holographic polymer dispersed liquid crystal optical material is subjected to polymerization reaction through exposure to form a holographic polymer dispersed liquid crystal grating with polymers and liquid crystals being arranged periodically, efficient phase separation of the polymers and the liquid crystals is a key for preparing the high-refractive-index grating, and regulation and control of the polymerization reaction is an effective method for improving the phase separation degree so as to improve the diffraction efficiency and the light transmittance of the grating.
Disclosure of Invention
The present invention aims to solve at least one of the technical problems existing in the prior art. Therefore, the invention provides a holographic polymer dispersed liquid crystal material and application thereof, wherein the holographic polymer dispersed liquid crystal material is designed, and the prepared holographic polymer dispersed liquid crystal material has excellent performance by selecting a liquid crystal composition with a specific structural formula and a polymerizable monomer, so that the prepared volume holographic grating has high diffraction efficiency and low haze.
A holographic polymer dispersed liquid crystal material according to the first aspect of the present invention, the holographic polymer dispersed liquid crystal material comprising a liquid crystal composition, an acrylic polymerizable monomer, a photoinitiator and a co-initiator;
the liquid crystal composition comprises compounds shown in the following formulas I-III, and the acrylic polymerizable monomer comprises a trifunctional polymerizable monomer and a compound shown in the following formula IV:
a compound of formula i:；
a compound of formula ii:；
a compound of formula iii:；
a compound of formula iv:；
wherein R is 1 And R is 3 Independent representations、/>、/>、/>An alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, an alkenyloxy group having 3 to 7 carbon atoms, wherein at least one hydrogen atom may be substituted with a fluorine atom;
R 2 representation of、/>、/>、/>An alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, wherein at least one hydrogen atom may be substituted with a fluorine atom;
representation->Or->；
X represents F, CF 3 、OCF 3 ；
L 1 ~L 4 Represents a fluorine atom or a hydrogen atom;
n 1 、n 2 and n 3 Each independently represents 1 or 2, and when n 1 When the number of the particles is 2, the particles are mixed,may be the same or different, when n 2 When 2 is, L 1 May be the same or different, when n 3 When 2 is, L 4 May be the same or different;
Sp 1 、Sp 2 each independently represents a single bond or a linear alkyl group having 1 to 6 carbon atoms, at least one or more-CH(s) in the linear alkyl group having 1 to 6 carbon atoms 2 -may be substituted by-O-, -COO-, or-c=c-;
Y 1 represents a fluorine atom, a chlorine atom, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkenyloxy group having 2 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms;
p represents 1, 2, 3, 4 or 5; q represents 0, 1, 2, 3 or 4, and when p is 2, 3, 4 or 5, Y 1 And q may be the same or different.
In some embodiments, the compound of formula I comprises at least one of the compounds of formulas I-1 to I-10:
a compound of formula i-1:；
a compound of formula i-2:；
a compound of formula i-3:；
a compound of formula i-4:；
a compound of formula i-5:；
a compound of formula i-6:；
a compound of formula i-7:；
a compound of formula i-8:；
a compound of formula i-9:；
a compound of formula i-10:。
in some embodiments, the compound of formula II comprises at least one of the compounds of formulas II-1 to II-12:
a compound of formula ii-1:；
a compound of formula ii-2:；
a compound of formula ii-3:；
a compound of formula ii-4:；
a compound of formula ii-5:；
a compound of formula ii-6:；
a compound of formula ii-7:；
a compound of formula ii-8:；
a compound of formula ii-9:；
a compound of formula ii-10:；
a compound of formula ii-11:；
a compound of formula ii-12:。
in some embodiments, the compound of formula III includes at least one of the compounds of formulas III-1 through III-6:
a compound of formula iii-1:；
a compound of formula iii-2:；
a compound of formula iii-3:；
a compound of formula iii-4:；
a compound of formula iii-5:；
a compound of formula iii-6:。
in some embodiments, the compound of formula IV includes at least one of the compounds of formulas IV-1 through IV-4:
a compound of formula iv-1:；
a compound of formula iv-2:；
a compound of formula iv-3:；
a compound of formula iv-4:。
in some embodiments, the trifunctional polymerizable monomer is trimethylolpropane triacrylate, the photoinitiator is rose bengal, and the co-initiator is N-phenylglycine.
In some alternative embodiments, the weight percentage of the compound of formula I is 1% to 10%, the weight percentage of the compound of formula II is 10% to 40%, and the weight percentage of the compound of formula III is 10% to 40%, based on 100% by weight of the holographic polymer dispersed liquid crystal material.
In some alternative embodiments, the weight percentage of the compound of formula IV is 40% to 70% and the weight percentage of the trifunctional polymerizable monomer is 5% to 10% based on 100% weight percentage of the holographic polymer dispersed liquid crystal material.
In some alternative embodiments, the photoinitiator is present in an amount of 0.1% to 1% by weight and the co-initiator is present in an amount of 0.1% to 1% by weight, based on 100% by weight of the holographic polymer dispersed liquid crystal material.
In a second aspect, the present invention provides the use of a holographic polymer dispersed liquid crystal material as described above for the preparation of a volume holographic grating.
Compared with the prior art, the invention has the following beneficial effects:
the holographic polymer dispersed liquid crystal material prepared by designing the holographic polymer dispersed liquid crystal material and selecting the liquid crystal composition with a specific structural formula and the polymerizable monomer has excellent performance, so that the prepared volume holographic grating has high diffraction efficiency and low haze, can be switched between a holographic state and a transparent state, and can meet the application requirements of the volume holographic optical waveguide.
Additional aspects and advantages of the invention will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention.
Detailed Description
To facilitate understanding of the present invention, examples are set forth below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The embodiment of the invention provides a holographic polymer dispersed liquid crystal material, which comprises a liquid crystal composition, an acrylic polymerizable monomer, a photoinitiator and a co-initiator; the liquid crystal composition comprises compounds shown in the following formulas I-III, and the acrylic polymerizable monomer comprises a trifunctional polymerizable monomer and a compound shown in the following formula IV.
Specifically, the compounds of formula I are:wherein R is 1 Representation->、、/>、/>An alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, an alkenyloxy group having 3 to 7 carbon atoms, wherein at least one hydrogen atom may be substituted with a fluorine atom. It is understood that wherein at least one hydrogen atom may be replaced by a fluorine atom means +.>、/>、、/>In the alkyl group having 1 to 7 carbon atoms, the alkoxy group having 1 to 7 carbon atoms, the alkenyl group having 2 to 7 carbon atoms, and the alkenyloxy group having 3 to 7 carbon atoms, a hydrogen atom is not substituted with a fluorine atom, or at least one hydrogen atom is substituted with a fluorine atom.
Further, the method comprises the steps of,representation->Or->；n 1 Represents 1 or 2, and when n 1 When 2, the drug is added>May be the same or different. When n is 1 When 2, two of the compounds of the formula I are +.>May be identical, e.g. twoAll are->Alternatively, two->All are->Two of the compounds of the formula I +.>Can also be different, i.e. two +.>One of them is->The other is +.>。
In the embodiment of the invention, the cycloalkyl in the compound shown in the formula I can improve the solubility among the compound shown in the formula I, the compound shown in the formula II and the compound shown in the formula III, reduce the risk of low-temperature crystallization of liquid crystal, and simultaneously, the olefin end group in the compound shown in the formula I can obviously reduce the rotational viscosity of the liquid crystal.
In an embodiment of the present invention, the compound represented by formula i may be at least one of the following compounds:
a compound of formula i-1:；
a compound of formula i-2:；
a compound of formula i-3:；
a compound of formula i-4:；
a compound of formula i-5:；
a compound of formula i-6:；
a compound of formula i-7:；
a compound of formula i-8:；
a compound of formula i-9:；
a compound of formula i-10:。
the above compounds are only examples of some of the compounds represented by the formula i, and should not be construed as limiting the compounds represented by the formula i.
Meanwhile, the compound shown in the formula II is:wherein R is 2 Representation->、、/>、/>An alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, wherein at least one hydrogen atom may be substituted with a fluorine atom; it is understood that wherein at least one hydrogen atom may be replaced by a fluorine atom means +.>、/>、/>、/>In the alkyl group having 1 to 7 carbon atoms and the alkoxy group having 1 to 7 carbon atoms, a hydrogen atom is not substituted with a fluorine atom, or at least one hydrogen atom is substituted with a fluorine atom.
X represents F, CF 3 、OCF 3 ，L 1 、L 2 And L 3 Each independently represents a fluorine atom or a hydrogen atom, n 2 Represents 1 or 2, and when n 2 When 2 is, L 1 May be the same or different, i.e. at n 2 When 2, two L in the compound shown in the formula II 1 Can be all fluorogenicOr both hydrogen atoms, or two L in the compound shown in the formula II 1 One being a fluorine atom and one being a hydrogen atom.
In the embodiment of the invention, the compound shown in the formula II is a polychlorinated biphenyl compound, and the polychlorinated biphenyl compound has higher conjugation, so that the compound has higher double refractive index, so that the diffraction efficiency of the grating can be improved, the compound shown in the formula II also comprises cycloalkyl, and the polychlorinated biphenyl compound containing cycloalkyl can improve the clear point of the liquid crystal composition, so that the service temperature of the holographic polymer dispersed liquid crystal material can be widened.
In an embodiment of the present invention, the compound represented by formula ii may be at least one of the following compounds:
a compound of formula ii-1:；
a compound of formula ii-2:；
a compound of formula ii-3:；
a compound of formula ii-4:；
a compound of formula ii-5:；
a compound of formula ii-6:；
a compound of formula ii-7:；
a compound of formula ii-8:；
a compound of formula ii-9:；
a compound of formula ii-10:；
a compound of formula ii-11:；
a compound of formula ii-12:。
the above compounds are only examples of the compounds represented by the formula ii, and should not be construed as limiting the compounds represented by the formula ii.
Meanwhile, the compound shown in the formula III is:wherein R is 3 Representation->、、/>、/>An alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, an alkenyloxy group having 3 to 7 carbon atoms, wherein at least one hydrogen atom may be substituted with a fluorine atom. It is understood that wherein at least one hydrogen atom may be replaced by a fluorine atom means +.>、/>、、/>In the alkyl group having 1 to 7 carbon atoms, the alkoxy group having 1 to 7 carbon atoms, the alkenyl group having 2 to 7 carbon atoms, and the alkenyloxy group having 3 to 7 carbon atoms, a hydrogen atom is not substituted with a fluorine atom, or at least one hydrogen atom is substituted with a fluorine atom.
L 4 Represents fluorine or hydrogen atoms, n 3 Represents 1 or 2, and when n 3 When 2 is, L 4 May be the same or different, i.e. at n 3 When 2, two L in the compound shown in the formula III 4 Can be both fluorine atoms or both hydrogen atoms, or can be two L in the compound shown in the formula III 4 One being a fluorine atom and one being a hydrogen atom.
In the embodiment of the invention, the compound shown in the formula III is a poly-biphenyl compound, and the poly-biphenyl compound has higher conjugation, so that the poly-biphenyl compound has higher double refractive index, and the diffraction efficiency of the grating can be improved.
In an embodiment of the present invention, the compound represented by formula iii may be at least one of the following compounds:
a compound of formula iii-1:；
a compound of formula iii-2:；
a compound of formula iii-3:；
a compound of formula iii-4:；
a compound of formula iii-5:；
a compound of formula iii-6:。
it will be appreciated that the above compounds are only examples of some of the compounds of formula III and should not be construed as limiting the compounds of formula III.
Further, the compound shown in the formula IV is:wherein Sp is 1 、Sp 2 Each independently represents a single bond or a linear alkyl group having 1 to 6 carbon atoms, at least one or more of which is-CH 2 -may be substituted by-O-, -COO-, or-c=c-;
Y 1 represents a fluorine atom, a chlorine atom, an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkenyloxy group having 2 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms;
p represents 1, 2, 3, 4 or 5; q represents 0, 1, 2, 3 or 4. When p represents 2, 3, 4 or 5, Y 1 And q may be the same or different, for example, when p represents 2, two (Y 1 ) q structure, two (Y 1 ) The q structures may be identical, i.e. q are each 0, 1, 2, 3 or 4, and Y 1 The radicals indicated are also identical, e.g. Y 1 All are fluorine atoms and the like; alternatively, two (Y 1 ) The q structure may also be different, wherein two Y's are possible 1 And two different from each other, may be two Y 1 Different or two q different. It will be appreciated that when p represents 3, 4 or 5, Y 1 Can be the same or different, q can be the same or different, and is not repeated hereSaid.
In the embodiment of the invention, the compound shown in the formula IV is a polymerizable monomer containing liquid crystal property, so that the phase state of liquid crystal can be maintained, and the compound shown in the formula IV is provided with an acrylic ester polymeric group, so that the polymerization reaction can be carried out.
The diffraction efficiency is determined by the refractive index modulation degree of the holographic polymer dispersed liquid crystal, the haze is determined by the size of the formed liquid crystal droplet, the phase separation rate of the liquid crystal composition and the polymerizable monomer during exposure determines the refractive index modulation degree and the liquid crystal droplet size, the polymerization speed is too high, the liquid crystal droplet size is large, the haze is high, the polymerization speed is too slow, the liquid crystal is wrapped by the polymer, the phase separation cannot be completed, and the refractive index modulation degree is low.
In the embodiment of the invention, the holographic polymer dispersed liquid crystal material comprises the compound shown in the formula I, the compound shown in the formula II, the compound shown in the formula III and the compound shown in the formula IV, and the compound shown in the formula II and the compound shown in the formula III can provide high double refractive indexes, so that the holographic polymer dispersed liquid crystal material has high diffraction efficiency, and the compound shown in the formula I can improve the solubility of each compound of the holographic polymer dispersed liquid crystal material, so that the phase change is not easy to occur, and the risk of low-temperature crystallization of liquid crystal can be reduced. In addition, the compound shown in the formula IV has proper intersolubility with the liquid crystal composition, so that the reaction rate in the polymerization reaction is just high or low, and the formed liquid crystal microdroplets have the right particle size. Thus, the volume hologram grating formed by the holographic polymer dispersed liquid crystal material has high diffraction efficiency and low haze.
In an embodiment of the present invention, the compound represented by formula iv may be at least one of the following compounds:
a compound of formula iv-1:；
a compound of formula iv-2:；
a compound of formula iv-3:；
a compound of formula iv-4:。
it should be noted that the above compounds are only examples of some of the compounds shown in the formula iv, and should not be construed as limiting the compounds shown in the formula iv.
In some embodiments, the trifunctional polymerizable monomer is trimethylolpropane triacrylate (Trimethylolpropane triacrylate, TMPTA), the photoinitiator is Rose Bengal (RB), and the co-initiator is N-phenylglycine (NPG). Of course, the trifunctional polymerizable monomer may also be pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetra-3-mercapto acrylate, ethoxy trimethylolpropane triacrylate, or the like, and the photoinitiator and co-initiator may also be other types of photoinitiators and co-initiators, which are not limited in this embodiment of the invention.
In some alternative embodiments, the weight percent of the compound of formula I is 1% to 10% based on 100% weight percent of the holographic polymer dispersed liquid crystal material, e.g., the weight percent of the compound of formula I may be 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, etc.; the weight percentage of the compound shown in the formula II is 10% -40%, for example, the weight percentage of the compound shown in the formula II can be 10%, 15%, 20%, 25%, 30%, 35%, 40%, etc., the weight percentage of the compound shown in the formula III is 10% -40%, for example, the weight percentage of the compound shown in the formula II can be 10%, 15%, 20%, 25%, 30%, 35%, 40%, etc.
In some alternative embodiments, the weight percent of the compound of formula IV is 40% to 70%, e.g., the weight percent of the compound of formula IV may be 40%, 45%, 50%, 55%, 60%, 65%, 70%, etc., and the weight percent of the trifunctional polymerizable monomer is 5% to 10%, e.g., the weight percent of the trifunctional polymerizable monomer may be 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, 10%, etc., based on 100% weight percent of the holographic polymer dispersed liquid crystal material.
In some alternative embodiments, the weight percent of photoinitiator is 0.1% -1% based on 100% weight percent of holographic polymer dispersed liquid crystal material, e.g., the weight percent of photoinitiator may be 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, etc.; the weight percentage of the co-initiator is 0.1% -1%, and the weight percentage of the co-initiator can be 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1% and the like.
In addition, the holographic polymer dispersed liquid crystal material provided by the embodiment of the invention can be configured by the preparation method: and (3) placing all the components of the holographic polymer dispersed liquid crystal material into a brown glass bottle according to a certain proportion, adding a magnetic rotor into the bottle, stirring for 20-40 min at 35-45 ℃ until the components are uniformly stirred, and cooling to room temperature to obtain the holographic polymer dispersed liquid crystal material.
The holographic polymer dispersed liquid crystal material provided by the embodiments of the present invention is specifically described below by way of a plurality of examples.
Example 1
The embodiment provides a holographic polymer dispersed liquid crystal material, which comprises the following components in percentage by weight:
example 2
The embodiment provides a holographic polymer dispersed liquid crystal material, which comprises the following components in percentage by weight:
example 3
The embodiment provides a holographic polymer dispersed liquid crystal material, which comprises the following components in percentage by weight:
example 4
The embodiment provides a holographic polymer dispersed liquid crystal material, which comprises the following components in percentage by weight:
example 5
The embodiment provides a holographic polymer dispersed liquid crystal material, which comprises the following components in percentage by weight:
comparative example 1
The comparative example provides a holographic polymer dispersed liquid crystal material comprising the following components in percentage by weight:
comparative example 2
The comparative example provides a holographic polymer dispersed liquid crystal material comprising the following components in percentage by weight:
comparative example 3
The comparative example provides a holographic polymer dispersed liquid crystal material comprising the following components in percentage by weight:
comparative example 4
The comparative example provides a holographic polymer dispersed liquid crystal material comprising the following components in percentage by weight:
the performance of the holographic polymer dispersed liquid crystal materials provided in the above examples and comparative examples was tested as follows:
the holographic polymer dispersed liquid crystal materials in the examples and the comparative examples are respectively put into brown glass bottles according to the proportion, a magnetic rotor is added into the bottles, stirring is started at the temperature of 40 ℃, stirring is carried out for 30min until the materials are uniform, and the holographic polymer dispersed liquid crystal materials are obtained after cooling to room temperature.
Then, the glass box is filled under the light-proof state, and the material is slowly sucked into the glass box by utilizing the siphon effect until the glass box is fully filled, wherein the thickness of the cavity of the glass box is 8 mu m. The performance of glass boxes containing the holographic polymer dispersed liquid crystal materials provided in the above examples and comparative examples, respectively, was tested.
Diffraction efficiency: the test was performed using a test light path provided on page 38 of the paper "study of holographic Polymer dispersed liquid Crystal (H-PDLC) gratings" by university of southward, where diffraction efficiency=diffraction intensity/incident light intensity×100%.
Haze test: haze was measured using a WGT-S transmittance/haze meter.
The performance test results of the holographic polymer dispersed liquid crystal materials provided in the above examples and comparative examples are shown in table 1 below:
in comparative example 1, after the laser irradiation phase separation, liquid crystal particles were precipitated, and it was not possible to test the diffraction efficiency and haze because the liquid crystal could not form a nematic phase at room temperature.
From the above, the holographic polymer dispersed liquid crystal material provided by the invention comprises the compound shown in the formula I, the compound shown in the formula II, the compound shown in the formula III and the holographic polymer dispersed liquid crystal material of the compound shown in the formula IV, and the compound shown in the formula II and the compound shown in the formula III can provide high double refractive indexes, so that the holographic polymer dispersed liquid crystal material has high diffraction efficiency, and the compound shown in the formula I can improve the solubility of each compound of the holographic polymer dispersed liquid crystal material, so that phase change is not easy to occur, and the risk of low-temperature crystallization of liquid crystal can be reduced. In addition, the compound shown in the formula IV and the liquid crystal composition have proper intersolubility, so that the reaction rate in the polymerization reaction is just high, the reaction rate is not too high or too low, liquid crystal microdroplets are formed to have the right particle diameter, the liquid crystal composition with a specific structural formula is selected, and the holographic polymer dispersed liquid crystal material prepared from the liquid crystal composition and the acrylic polymerizable monomer has excellent performance, so that the prepared volume holographic grating has high diffraction efficiency and low haze, can be switched between a holographic state and a transparent state, can meet the application requirements of the volume holographic optical waveguide, and has the diffraction efficiency of 65% -72% and the haze of 1.1% -1.5%.
In comparison with examples 1 to 5, if the liquid crystal composition contains only any two of the compound represented by formula I, the compound represented by formula II or the compound represented by formula III (comparative examples 1 to 3), the prepared holographic polymer dispersed liquid crystal material has poor properties, and cannot be used for preparing a volume hologram grating (comparative example 1), or the prepared volume hologram grating has low diffraction efficiency (comparative examples 2 to 3).
Compared with the embodiment 1-embodiment 5, if the polymerizable monomer with other structural formulas is selected (comparative example 4), the prepared holographic polymer dispersed liquid crystal material has poorer performance, and the prepared volume holographic grating has low diffraction efficiency and higher haze.
In summary, the holographic polymer dispersed liquid crystal material prepared by designing the holographic polymer dispersed liquid crystal material, selecting the liquid crystal composition with a specific structural formula and preparing the holographic polymer dispersed liquid crystal material with the acrylate polymerizable monomer has excellent performance, so that the prepared volume holographic grating has high diffraction efficiency and low haze, can be switched between a holographic state and a transparent state, and can meet the application requirements of the volume holographic optical waveguide.
In a second aspect, the present invention provides the use of a holographic polymer dispersed liquid crystal material as described above for the preparation of a volume holographic grating.
In the description of the present invention, it should be understood that the terms "center," "longitudinal," "transverse," "length," "width," "thickness," "upper," "lower," "front," "rear," "left," "right," "vertical," "horizontal," "top," "bottom," "inner," "outer," "clockwise," "counterclockwise," "axial," "radial," "circumferential," etc. are merely for convenience of description and to simplify the description, and do not indicate or imply that the devices or elements referred to must have a particular orientation, be constructed and operated in a particular orientation, and thus should not be construed as limiting the invention.
Furthermore, the terms "first," "second," and the like, are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include one or more such feature. In the description of the present invention, the meaning of "a plurality" is two or more, unless explicitly defined otherwise.
In the present invention, unless explicitly specified and limited otherwise, the terms "mounted," "connected," "secured," and the like are to be construed broadly, and may be, for example, fixedly connected, detachably connected, or integrally formed; the device can be mechanically connected, electrically connected and communicated; can be directly connected or indirectly connected through an intermediate medium, and can be communicated with the inside of two elements or the interaction relationship of the two elements. The specific meaning of the above terms in the present invention can be understood by those of ordinary skill in the art according to the specific circumstances.
In the present invention, unless expressly stated or limited otherwise, a first feature "up" or "down" a second feature may be the first and second features in direct contact, or the first and second features in indirect contact via an intervening medium. Moreover, a first feature being "above," "over" and "on" a second feature may be a first feature being directly above or obliquely above the second feature, or simply indicating that the first feature is level higher than the second feature. The first feature being "under", "below" and "beneath" the second feature may be the first feature being directly under or obliquely below the second feature, or simply indicating that the first feature is less level than the second feature.
In the description of the present specification, a description referring to terms "one embodiment," "some embodiments," "examples," "specific examples," or "some examples," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present invention. In this specification, schematic representations of the above terms are not necessarily directed to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, the different embodiments or examples described in this specification and the features of the different embodiments or examples may be combined and combined by those skilled in the art without contradiction.
While embodiments of the present invention have been shown and described, it will be understood by those of ordinary skill in the art that: many changes, modifications, substitutions and variations may be made to the embodiments without departing from the spirit and principles of the invention, the scope of which is defined by the claims and their equivalents.
Claims (9)
1. A holographic polymer dispersed liquid crystal material, which is characterized by comprising a liquid crystal composition, an acrylic polymerizable monomer, a photoinitiator and a co-initiator;
the liquid crystal composition comprises compounds shown in the following formulas I-III, and the acrylic polymerizable monomer comprises trimethylolpropane triacrylate and at least one compound shown in the following formulas IV-1-IV-4:
a compound of formula i:；
a compound of formula ii:；
a compound of formula iii:；
a compound of formula iv-1:；
a compound of formula iv-2:；
a compound of formula iv-3:；
a compound of formula iv-4:；
wherein R is 1 And R is 3 Independent representations、/>、/>、/>An alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, an alkenyloxy group having 3 to 7 carbon atoms, wherein at least one hydrogen atom may be substituted with a fluorine atom;
R 2 representation of、/>、/>、/>An alkyl group having 1 to 7 carbon atoms and an alkoxy group having 1 to 7 carbon atoms, wherein at least one hydrogen atom may be substituted with a fluorine atom;
representation->Or->；
X represents F, CF 3 、OCF 3 ；
L 1 ~L 4 Represents a fluorine atom or a hydrogen atom;
n 1 、n 2 and n 3 Each independently represents 1 or 2, and when n 1 When the number of the particles is 2, the particles are mixed,may be the same or different, when n 2 When 2 is, L 1 May be the same or different, when n 3 When 2 is, L 4 May be the same or different.
2. The holographic polymer dispersed liquid crystal material of claim 1, in which the compound of formula i comprises at least one of the compounds of formulae i-1 to i-10:
a compound of formula i-1:；
a compound of formula i-2:；
a compound of formula i-3:；
a compound of formula i-4:；
a compound of formula i-5:；
a compound of formula i-6:；
a compound of formula i-7:；
a compound of formula i-8:；
a compound of formula i-9:；
a compound of formula i-10:。
3. the holographic polymer dispersed liquid crystal material of claim 1, in which the compound of formula ii comprises at least one of the compounds of formulae ii-1 to ii-12:
a compound of formula ii-1:；
a compound of formula ii-2:；
a compound of formula ii-3:；
a compound of formula ii-4:；
a compound of formula ii-5:；
a compound of formula ii-6:；
a compound of formula ii-7:；
a compound of formula ii-8:；
a compound of formula ii-9:；
a compound of formula ii-10:；
a compound of formula ii-11:；
a compound of formula ii-12:。
4. the holographic polymer dispersed liquid crystal material of claim 1, in which the compound of formula iii comprises at least one of the compounds of formulae iii-1 to iii-6:
a compound of formula iii-1:；
a compound of formula iii-2:；
a compound of formula iii-3:；
a compound of formula iii-4:；
a compound of formula iii-5:；
a compound of formula iii-6:。
5. the holographic polymer dispersed liquid crystal material of any of claims 1-4, in which the photoinitiator is rose bengal and the co-initiator is N-phenylglycine.
6. The holographic polymer dispersed liquid crystal material of claim 5, in which the weight percentage of the compound of formula i is 1% to 10%, the weight percentage of the compound of formula ii is 10% to 40%, and the weight percentage of the compound of formula iii is 10% to 40%, based on 100% weight percentage of the holographic polymer dispersed liquid crystal material.
7. The holographic polymer dispersed liquid crystal material of claim 5, in which the total weight percentage of the compounds of formulae iv-1 to iv-4 is 40% to 70% and the weight percentage of trimethylolpropane triacrylate is 5% to 10% based on 100% weight percentage of the holographic polymer dispersed liquid crystal material.
8. The holographic polymer dispersed liquid crystal material of claim 5, in which the photoinitiator comprises 0.1% to 1% by weight and the co-initiator comprises 0.1% to 1% by weight, based on 100% by weight of the holographic polymer dispersed liquid crystal material.
9. Use of a holographic polymer dispersed liquid crystal material according to any of claims 1 to 8 for the preparation of a volume holographic grating.
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