CN115627175A - Liquid crystal composition and liquid crystal optical element - Google Patents
Liquid crystal composition and liquid crystal optical element Download PDFInfo
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- CN115627175A CN115627175A CN202211215908.5A CN202211215908A CN115627175A CN 115627175 A CN115627175 A CN 115627175A CN 202211215908 A CN202211215908 A CN 202211215908A CN 115627175 A CN115627175 A CN 115627175A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 144
- 239000000203 mixture Substances 0.000 title claims abstract description 114
- 230000003287 optical effect Effects 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 147
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 238000002834 transmittance Methods 0.000 abstract description 7
- 230000006872 improvement Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 10
- 239000004983 Polymer Dispersed Liquid Crystal Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000005276 holographic polymer dispersed liquid crystals (HPDLCs) Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 description 3
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000001427 coherent effect Effects 0.000 description 2
- -1 ethoxylated aliphatic alkylamines Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- WTQIZFCJMGWUGZ-UHFFFAOYSA-N 5-methyl-2-(2-phenylpropan-2-yl)cyclohexan-1-ol Chemical compound OC1CC(C)CCC1C(C)(C)C1=CC=CC=C1 WTQIZFCJMGWUGZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Classifications
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- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nonlinear Science (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The application provides a liquid crystal composition, which comprises at least one compound shown in a general formula (1), at least one of compounds shown in a general formula (2), and at least one of compounds shown in a general formula (3) and compounds shown in a general formula (4). The liquid crystal composition provided by the application has higher diffraction efficiency, and the transmittance cannot be reduced due to the improvement of the diffraction efficiency. In addition, the application also provides a liquid crystal optical element.
Description
Technical Field
The application belongs to the technical field of liquid crystal, and particularly relates to a liquid crystal composition and a liquid crystal optical element.
Background
In recent years, liquid crystal materials have been widely used in the display industry and in phase optical elements, and television sets, computer monitors, and mobile phone monitors utilize optical anisotropy and dielectric anisotropy of liquid crystal materials to realize display functions. The liquid crystal material and the polymerizable monomer are mixed to form embedded Polymer Dispersed Liquid Crystal (PDLC) under the conditions of a photosensitizer and UV irradiation, and the embedded PDLC is widely applied to the direction of a light adjusting film.
Meanwhile, the liquid crystal material and the polymerizable material monomer are widely researched and tested to form the holographic body grating and the optical waveguide device under the irradiation of the photosensitizer and the coherent light source. The fabrication of the optical waveguide may include a material system that allows the recording of holographic optical elements within the waveguide. For example, a Polymer Dispersed Liquid Crystal (PDLC) mixture, which is a mixture containing a photopolymerizable monomer and liquid crystal, is included. Also included are Holographic Polymer Dispersed Liquid Crystal (HPDLC) mixtures in which two coherent laser beams can be used to record, for example, the volume phase. During recording, the monomer polymerizes and the mixture undergoes a photo-polymerization induced phase separation to form liquid crystal-rich regions that are filled with a liquid crystal droplet in an enriched state, liquid crystal-poor regions interspersed with a transparent polymer, and the alternating liquid crystal-rich and liquid crystal-poor regions form the striated surface of the grating. The final grating, commonly referred to as a Switchable Bragg Grating (SBG), has all the properties often associated with volume or bragg gratings, and has a higher refractive index modulation range and the ability to electrically tune the grating over a continuous range of diffraction efficiencies (the proportion of incident light that is diffracted into a desired direction) compared to bragg gratings.
The optical waveguide devices described above can be used in a range of display and sensor applications. Waveguides comprising one or more grating layers encoding various optical functions can be implemented in a variety of applications using a variety of waveguide structures and material systems, such as near-eye displays for Augmented Reality (AR) and Virtual Reality (VR), compact head-up displays (HUD) and head-mounted displays (HMD) for road transport, aviation and military applications, and for biometric identification and lidar, among others.
The polymer dispersed liquid crystal structure in the related art has a small viewing angle, and if the viewing angle needs to be increased, other parameters such as diffraction efficiency and the like are reduced, which becomes an obstacle for limiting the application of the liquid crystal material.
Disclosure of Invention
It is an object of the present invention to provide a liquid crystal composition and a liquid crystal optical element, which improve at least some of the above-mentioned technical problems.
The embodiment of the application provides a liquid crystal composition, which comprises at least one of compounds in a general formula (1), at least one of compounds in a general formula (2), at least one of compounds in a general formula (3) and at least one of compounds in a general formula (4);
the compound of the general formula (1) is:
the compound of the general formula (2) is:
wherein R is 1 And R 2 Independently selected from alkyl or alkoxy of 1-12 carbon atoms or alkenyl of 2-12 carbon atoms, and in the compound of the general formula (1) and the compound of the general formula (2), R and R are 1 Or R 2 2,3,5,6 carbon atoms on adjacent benzene rings can be substituted by nitrogen atoms, and any H atom on the benzene ring can be substituted by F;
the compound of the general formula (3) is:
wherein R is 3 Selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, and in the compound of the general formula (3), with R 3 2,3,5,6 carbon atoms on adjacent benzene rings can be replaced by nitrogen atoms, and any carbon atom on a cyclohexane ring can be replaced by an oxygen atom;
the compound of the general formula (4) is:
wherein R is 4 Selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, D represents a cyclohexane or benzene ring, any H atom on D may be substituted by F, n =0 or 1, and when n =1 and D is a cyclohexane ring, 2,3,5,6 carbon atoms on D may be substituted by oxygen atoms.
In some embodiments, the mass percent of the compound of formula (1) in the total mass of the liquid crystal composition is from 1% to 95%; the mass percentage of the compound of the general formula (2) in the total mass of the liquid crystal composition is 1-95%; the mass percentage of the compound of the general formula (3) in the total mass of the liquid crystal composition is 1-65%; the mass percentage of the compound of the general formula (4) in the total mass of the liquid crystal composition is 1-65%.
Preferably, the mass percentage of the compound of the general formula (1) in the total mass of the liquid crystal composition is 1 to 75 percent; the mass percentage of the compound of the general formula (2) in the total mass of the liquid crystal composition is 1-90%; the mass percentage of the compound of the general formula (3) in the total mass of the liquid crystal composition is 1-55%; the mass percentage of the compound of the general formula (4) in the total mass of the liquid crystal composition is 1-50%.
Preferably, the mass percentage of the compound of the general formula (1) in the total mass of the liquid crystal composition is 1 to 65%; the mass percentage of the compound of the general formula (2) in the total mass of the liquid crystal composition is 40-80%; the mass percentage of the compound of the general formula (3) in the total mass of the liquid crystal composition is 1-45%; the mass percentage of the compound of the general formula (4) in the total mass of the liquid crystal composition is 1-40%.
In some embodiments, R 1 、R 2 、R 3 、R 4 Each independently selected from alkyl or alkoxy of 1 to 6 carbon atoms or alkenyl of 2 to 6 carbon atoms.
In some embodiments, the compound of formula (1) is selected from one or more of the following compounds:
in some embodiments, the compound of formula (2) is selected from one or more of the following compounds:
in some embodiments, the compound of formula (3) is selected from one or more of the following compounds:
preferably, the compound of formula (4) is selected from one or more of the following compounds:
in some embodiments, the liquid crystal compound further comprises at least one of an anti-uv agent, an antioxidant, a chiral agent.
The embodiment of the application also provides a liquid crystal optical element, and the liquid crystal optical element is prepared from the liquid crystal composition.
The liquid crystal composition has higher diffraction efficiency, and the transmittance is not reduced while the high diffraction efficiency is realized, so that the purpose of improving the diffraction efficiency while other parameters of the liquid crystal compound are stable is realized. In addition, the liquid crystal composition provided by the application has higher phase transition temperature when the nematic phase is changed into isotropy and wider nematic phase temperature width, so that the liquid crystal compound can have larger working temperature width when being applied to a liquid crystal optical element.
These and other aspects of the present application will be more readily apparent from the following description of the embodiments.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
In related researches, it is found that the field angle VOP of the grating can be effectively increased by reducing the thickness of the polymer dispersed liquid crystal structure, but the diffraction efficiency of the grating is obviously reduced after the thickness of the structure is reduced, and in some researches, it is mentioned that the diffraction efficiency can be increased by increasing the refractive index difference between the liquid crystal material and the polymer material, but in doing so, the scattering of the grating is increased, and the transmittance is reduced.
The application proposes a liquid crystal composition comprising at least one of the compounds of the general formula (1), and at least one of the compounds of the general formula (2) and at least one of the compounds of the general formula (3) and at least one of the compounds of the general formula (4).
That is, the liquid crystal composition includes the compound of the general formula (1), the compound of the general formula (2), the compound of the general formula (3), and the compound of the general formula (4) at the same time. It should be noted that the compound of formula (1) included in the liquid crystal composition may be one or more, and likewise, the compound of formula (2) may be one or more; the compound of the general formula (3) may be one or more; the compound of the general formula (4) may be one or more. It is understood that plural in this application means two or more, i.e. at least two.
The compounds of general formula (1) are:
wherein R is 1 Selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, and in said compounds of general formula (1) and in said compounds of general formula (2), with R 1 The 2,3,5,6 carbon atoms on the adjacent benzene ring can be substituted by nitrogen (N) atoms, and any H (hydrogen) atom on the benzene ring can be substituted by F (fluorine), and it is understood that the H atom substituted by F atom can be mono-substituted or multi-substituted, and is not limited herein. In this application, the 2,3,5,6 carbon atom on the benzene ring refers to the carbon atoms on the benzene ring other than the para-substituted group.
In some embodiments, R 1 May be selected from alkyl or alkoxy groups of 1 to 6 carbon atoms or alkenyl groups of 2 to 6 carbon atoms. R 1 The chain length of (2) is shorter, the molecular polarity can be effectively reduced, the refractive index can be increased, and simultaneously, R 1 Alkyl and alkoxy groups are preferred, which can reduce the degree of unsaturation in the liquid crystal composition and improve the stability of the molecules to ultraviolet light and heat.
The mass percentage of the compound of the general formula (1) in the total mass of the liquid crystal composition may be, for example, 1% to 95%, and the mass ratio of the compound of the general formula (1) to the liquid crystal composition may be, for example, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 85%, 90%, 95%, or the like. Preferably, the mass percentage of the compound of formula (1) in the total mass of the liquid crystal composition can be controlled to be 1% to 75%, such as 8%, 12%, 25%, 28%, 35%, 45%, 50%, 55%, 60%, 70%, 73%, etc., without limitation, and by controlling the proportion of the compound of formula (1) in the liquid crystal composition, the birefringence of the liquid crystal composition can be more precisely controlled, and a more desirable liquid crystal composition can be obtained. More preferably, the mass percentage of the compound of formula (1) in the total mass of the liquid crystal composition may be controlled to be 1% to 65%, for example, 1% to 10%,1% to 25%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, etc., without limitation.
Illustratively, as shown below, the present application shows specific molecular structures of some compounds of formula (1), and one or more of the following compounds may be selected for use in the liquid crystal compound:
it is to be understood that the various compounds described above are exemplary only and should not be construed as limiting the compounds of formula (1). Among them, the compounds represented by the above general formula (1) have a short chain length and a small number of rings, and when one or more of them are added to a liquid crystal composition, they are advantageous in improving the diffraction efficiency of the liquid crystal composition.
The compound of the general formula (2) is:
wherein R is 2 Selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, and in said compounds of general formula (1) and in said compounds of general formula (2), with R 2 The 2,3,5,6 carbon atoms on the adjacent benzene ring can be substituted by nitrogen atoms, any H atom on the benzene ring can be substituted by F, and it is understood that the H atom substituted by F atom can be mono-substituted or multi-substituted, and is not limited herein.
In some embodiments, R 2 May be selected from alkyl or alkoxy groups of 1 to 6 carbon atoms or alkenyl groups of 2 to 6 carbon atoms. R 1 The chain length of (A) is shorter, the molecular polarity can be effectively reduced, the refractive index can be increased, and simultaneously, R 2 Alkyl and alkoxy groups are preferred, which may reduce the degree of unsaturation in the liquid crystal composition and improve the stability of the molecules to ultraviolet light and heat.
The mass percentage of the compound of the general formula (2) in the total mass of the liquid crystal composition may be, for example, 1% to 95%, and the mass ratio of the compound of the general formula (2) to the liquid crystal composition may be, for example, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or the like. Preferably, the mass percentage of the compound of formula (2) in the total mass of the liquid crystal composition can be controlled to be 10% to 90%, for example, 10%, 12%, 25%, 28%, 35%, 45%, 50%, 55%, 62%, 68%, 78%, 82%, 88%, etc., without limitation, and by controlling the proportion of the compound of formula (2) in the liquid crystal composition, the birefringence of the liquid crystal composition can be more precisely controlled, and a more desirable liquid crystal composition can be obtained. More preferably, the mass percentage of the compound of the general formula (2) in the total mass of the liquid crystal composition may be controlled to be 40% to 80%, for example, 40% to 50%,40% to 60%, 50% to 60%, 60% to 80%, 50% to 70%, 70% to 80%, etc., without limitation.
Illustratively, as shown below, the present application shows specific molecular structures of some compounds of formula (2), and one or more of the following compounds may be selected for use in the liquid crystal compound:
when one or more compounds of the general formula (2) are added to the liquid crystal composition, the diffraction efficiency of the liquid crystal composition is improved.
It is to be understood that the various compounds described above are exemplary only and should not be construed as limiting the compounds of formula (2).
The compounds of formula (3) are:
R 3 selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, in the compound of the general formula (3), with R 3 The 2,3,5,6 carbon atoms of the adjacent benzene rings can be substituted by nitrogen atoms, and it is understood that, when the carbon atoms are substituted by the nitrogen atoms, the substitution can be mono-substitution or multi-substitution, and is not limited herein. Meanwhile, any carbon (C) atom on the cyclohexane ring may be substituted by an oxygen (O) atom, wherein O may be mono-substituted, di-substituted or poly-substituted when O is substituted for the C atom, and preferably O may be mono-substituted or di-substituted when O is substituted for the C atom.
In some embodiments, R 3 May be selected from alkyl or alkoxy groups of 1 to 6 carbon atoms or alkenyl groups of 2 to 6 carbon atoms. R 3 The chain length of (A) is shorter, the molecular polarity can be effectively reduced, and the chain length is increasedLarge refractive index, at the same time, R 3 Alkyl and alkoxy groups are preferred, which may reduce the degree of unsaturation in the liquid crystal composition and improve the stability of the molecules to ultraviolet light and heat.
The mass percentage of the compound of the general formula (3) in the total mass of the liquid crystal composition may be, for example, 1% to 65%, and the mass ratio of the compound of the general formula (3) to the liquid crystal composition may be, for example, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 65%, or the like. Preferably, the mass percentage of the compound of formula (3) in the total mass of the liquid crystal composition can be controlled to be 1% -55%, such as 8%, 12%, 25%, 28%, 35%, 45%, 50%, 55%, etc., without limitation, and by controlling the proportion of the compound of formula (3) in the liquid crystal composition, the birefringence of the liquid crystal composition can be more precisely controlled, and thus a more desirable liquid crystal composition can be obtained. More preferably, the mass percentage of the compound of formula (3) in the total mass of the liquid crystal composition may be controlled to be 1% to 45%, for example, 1% to 10%,1% to 25%, 35%, 40%, 45%, etc., without limitation.
Illustratively, as shown below, the present application shows specific molecular structures of some compounds of formula (3), and one or more of the following compounds may be selected for use in the liquid crystal compound:
when one or more compounds of the general formula (3) are added to the liquid crystal composition, the diffraction efficiency of the liquid crystal composition is improved. It is to be understood that the various compounds described above are exemplary only and should not be construed as limiting the compounds of formula (3).
The compound of the general formula (4) is:
wherein R is 4 Selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, and in some embodiments, R 1 May be selected from alkyl or alkoxy groups of 1 to 6 carbon atoms or alkenyl groups of 2 to 6 carbon atoms. R 4 The chain length of (A) is shorter, the molecular polarity can be effectively reduced, the refractive index can be increased, and simultaneously, R 4 Alkyl and alkoxy groups are preferred, which can reduce the degree of unsaturation in the liquid crystal composition and improve the stability of the molecules to ultraviolet light and heat.
D represents a cyclohexane ring or a benzene ring, any H atom on D may be substituted by F, n =0 or 1, and when n =1 and D is a cyclohexane ring, 2,3,5,6 carbon atoms on D may be substituted by oxygen atoms. Wherein O may be mono-substituted, di-substituted or poly-substituted when substituting C atom, preferably O may be mono-substituted or di-substituted when substituting C atom.
The mass percentage of the compound of the general formula (4) in the total mass of the liquid crystal composition may be, for example, 1% to 65%, and the mass ratio of the compound of the general formula (4) to the liquid crystal composition may be, for example, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 65%, or the like. Preferably, the mass percentage of the compound of formula (4) in the total mass of the liquid crystal composition can be controlled to be 1% to 50%, such as 8%, 12%, 25%, 28%, 35%, 45%, 50%, etc., without limitation, and by controlling the proportion of the compound of formula (4) in the liquid crystal composition, the birefringence of the liquid crystal composition can be more precisely controlled, and thus a more desirable liquid crystal composition can be obtained. More preferably, the mass percentage of the compound of formula (4) in the total mass of the liquid crystal composition can be controlled to be 1% to 40%, such as 1% to 10%,1% to 25%, 35%, 40%, etc., without limitation.
Illustratively, as shown below, the present application shows specific molecular structures of some compounds of formula (4), and one or more of the following compounds may be selected for use in the liquid crystal compound:
when one or more compounds of the general formula (4) are added to the liquid crystal composition, the diffraction efficiency of the liquid crystal composition is improved. It is to be understood that the various compounds described above are exemplary only and should not be construed as limiting the compounds of formula (4).
The compound of formula (1) may be combined with any one or more compounds of formula (2) and any one or more compounds of formula (3) and any one or more compounds of formula (4) to obtain a liquid crystal composition, which is not limited herein.
In some more particular embodiments, the mass percentage ratio between the compound of formula (1), the compound of formula (2), the compound of formula (3), and the compound of formula (4) may be (3-4): (3-4): (1-2): (1-2), wherein the mass percentage ratio among the compound of the general formula (2), the compound of the general formula (3), and the compound of the general formula (4) may be (3-4): (1-2): (1-2), under the proportion, the diffraction efficiency of the obtained liquid crystal composition can be improved by about 10%, and the liquid crystal composition has a good application prospect.
In some embodiments, the liquid crystal composition may further include other additives, such as an anti-uv agent, an antioxidant, a chiral agent, and the like, and the liquid crystal compound may further include an antistatic agent, an antifoaming agent, and the like, which are not limited herein. The uvioresistant agent may be, for example, benzophenone, benzotriazole, and the antioxidant may be, for example, BHA (butylhydroxyanisole), BHT (butylated hydroxytoluene), TBHQ (t-butylhydroquinone), etc. The chiral agent may be, for example, oxazolidinone, 8-phenyl menthol, and the like. The defoaming agent may be, for example, a silicone defoaming agent, ethylene oxide, propylene oxide, or the like. The antistatic agent may be, for example, ethoxylated aliphatic alkylamines, sodium alkylsulfonates, and the like.
The addition amount of the additive is preferably 1% by mass or less based on the total mass of the liquid crystal composition, and the addition amount and the addition type of the additive do not affect the properties of the liquid crystal composition.
The liquid crystal composition proposed in the present application will be specifically described below by way of examples.
The liquid crystal composition provided by the invention can be prepared by adopting the known technology in the field, and can be prepared by the following method: the components in the liquid crystal composition are uniformly mixed by stirring or ultrasonic mixing. The liquid crystal compositions in the following examples were mixed with stirring to obtain homogeneous compositions, and physical and chemical properties thereof were measured. For convenience of explanation, the group structures of the liquid crystal compositions in the following examples and comparative examples are represented by codes shown in table 1:
TABLE 1 code comparison Table for each group structure
Take the example of a compound of the formula:
from left to right, the formula is represented by the above code, and can be expressed as PP-5-N.
As shown in table 2, the codes and the component ratios of the liquid crystal compositions in the examples are specifically shown below:
TABLE 2 ingredient composition Table of liquid crystal composition in each of examples and comparative examples
The liquid crystal compositions obtained in examples 1 to 6 and comparative example 1 were subjected to a test, and the following parameters were measured:
tni (. Degree. C.) represents the temperature at which the nematic phase is changed to isotropy and is also expressed as the clearing point temperature;
Δ n represents a refractive index of optical anisotropy at a wavelength of 589nm at 20 ℃;
n o the refractive index of ordinary light in the liquid crystal;
n e the refractive index of the extraordinary ray in the liquid crystal;
t represents the transmittance, T = (I) d +I t )/I 0 ；
η represents the relative diffraction efficiency, η = Id/(I) d +I t )I d To diffract light intensity, I t To transmit light intensity, I 0 Is the light intensity of the light source.
The data obtained from the measurements are shown in table 3:
table 3 table of measurement results of examples 1 to 6 and comparative example 1
As can be seen from the data in Table 3, the Δ n was increased from 0.26 to about 0.29, and the corresponding relative diffraction efficiency was increased from 70% to about 80% and up to 10% for the liquid crystal compositions obtained in comparative examples 1-6 and comparative example 1. Meanwhile, the liquid crystal compositions obtained in examples 1 to 6 did not undergo a significant decrease in transmittance as compared with comparative example 1, and were almost equal to the comparative example, and it was found that this example can improve the relative diffraction efficiency without decreasing the transmittance.
Meanwhile, compared with the comparative example 1 in the prior art, the liquid crystal compositions obtained in the examples 1 to 6 have the advantages that the high temperature Tni in the nematic phase temperature range is improved to be more than 100 ℃, the nematic phase temperature range is wider than that of the conventional liquid crystal composition comparative example, the advantages are achieved, and the excellent effect is achieved in practical application. In summary, the liquid crystal composition obtained in the embodiments of the present application can improve the relative diffraction efficiency without reducing the transmittance.
One of the applications of the liquid crystal composition is to manufacture a liquid crystal optical element, wherein the liquid crystal optical element can be a liquid crystal lens to provide good electric control characteristics of the liquid crystal lens. The liquid crystal optical device may be a phase modulator, a holographic polymer dispersed liquid crystal grating (HPDLC), a Polymer Dispersed Liquid Crystal (PDLC) light modulation element, and the like, which is not limited herein.
The application also provides a liquid crystal optical element which is prepared from the liquid crystal composition.
The above description is only a preferred embodiment of the present application and is not intended to limit the present application, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application shall be included in the protection scope of the present application.
Claims (10)
1. A liquid crystal composition, comprising:
at least one compound of the general formula (1);
and
at least one compound of the general formula (2);
and
at least one compound of the general formula (3);
and
at least one compound of the general formula (4);
the compound of the general formula (1) is:
the compound of the general formula (2) is:
wherein R is 1 And R 2 Independently selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, and compounds of the general formula (1) andin the compound of the general formula (2), with R 1 And R 2 2,3,5,6 carbon atoms on adjacent benzene rings can be substituted by nitrogen atoms, and any H atom on the benzene ring can be substituted by F;
the compound of the general formula (3) is:
wherein R is 3 Selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, and in the compound of the general formula (3), with R 3 The 2,3,5,6 carbon atoms on the adjacent benzene rings can be replaced by nitrogen atoms, and any carbon atom on the cyclohexane ring can be replaced by oxygen atoms;
the compound of the general formula (4) is:
wherein R is 4 Selected from alkyl or alkoxy of 1 to 12 carbon atoms or alkenyl of 2 to 12 carbon atoms, D represents a cyclohexane or benzene ring, any H atom on D may be substituted by F, n =0 or 1, and when n =1 and D is a cyclohexane ring, 2,3,5,6 carbon atoms on D may be substituted by oxygen atoms.
2. The liquid crystal composition according to claim 1, wherein the mass percentage of the compound of the general formula (1) in the total mass of the liquid crystal composition is 1 to 95%;
the mass percentage of the compound of the general formula (2) in the total mass of the liquid crystal composition is 1-95%;
the mass percentage of the compound of the general formula (3) in the total mass of the liquid crystal composition is 1-65%;
the mass percentage of the compound of the general formula (4) in the total mass of the liquid crystal composition is 1-65%.
3. The liquid crystal composition according to claim 2, wherein the mass percentage of the compound of the general formula (1) in the total mass of the liquid crystal composition is 1 to 75%;
the mass percentage of the compound of the general formula (2) in the total mass of the liquid crystal composition is 10-90%;
the mass percentage of the compound of the general formula (3) in the total mass of the liquid crystal composition is 1-55%;
the mass percentage of the compound of the general formula (4) in the total mass of the liquid crystal composition is 1-50%.
4. The liquid crystal composition according to claim 3, wherein the mass percentage of the compound of the general formula (1) in the total mass of the liquid crystal composition is 1 to 65%;
the mass percentage of the compound of the general formula (2) in the total mass of the liquid crystal composition is 40-80%;
the mass percentage of the compound of the general formula (3) in the total mass of the liquid crystal composition is 1-45%;
the mass percentage of the compound of the general formula (4) in the total mass of the liquid crystal composition is 1-40%.
5. The liquid crystal composition of claim 1, wherein R is 1 、R 2 、R 3 、R 4 Each independently selected from alkyl or alkoxy of 1 to 6 carbon atoms or alkenyl of 2 to 6 carbon atoms.
6. Liquid crystal composition according to claim 1, characterized in that the compound of general formula (1) is selected from one or more of the following compounds:
7. liquid crystal composition according to claim 1, characterized in that the compound of general formula (2) is selected from one or more of the following compounds:
8. liquid crystal composition according to claim 1, characterized in that the compound of general formula (3) is selected from one or more of the following compounds:
9. liquid crystal composition according to claim 1, characterized in that the compound of general formula (4) is selected from one or more of the following compounds:
10. a liquid crystal optical element, characterized in that it is made of the liquid crystal composition according to any one of claims 1 to 9.
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