CN115368912B - Liquid crystal composition, reflective film and preparation method thereof - Google Patents
Liquid crystal composition, reflective film and preparation method thereof Download PDFInfo
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- CN115368912B CN115368912B CN202210686544.2A CN202210686544A CN115368912B CN 115368912 B CN115368912 B CN 115368912B CN 202210686544 A CN202210686544 A CN 202210686544A CN 115368912 B CN115368912 B CN 115368912B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 43
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 5
- -1 2-methylpropan-2-enoyl Chemical group 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 13
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 6
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 238000009826 distribution Methods 0.000 abstract description 11
- 230000003098 cholesteric effect Effects 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 230000006340 racemization Effects 0.000 abstract description 3
- 238000004132 cross linking Methods 0.000 abstract description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 7
- ZFAMIWROYLDZIB-UHFFFAOYSA-N 6-(4-benzoylperoxycarbonylphenoxy)hexyl prop-2-enoate Chemical compound C(C1=CC=CC=C1)(=O)OOC(C1=CC=C(C=C1)OCCCCCCOC(C=C)=O)=O ZFAMIWROYLDZIB-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 238000000985 reflectance spectrum Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- ISSYGWIDLYOJEN-UHFFFAOYSA-N [3-methyl-4-[4-(3-prop-2-enoyloxypropoxy)benzoyl]oxyphenyl] 4-(3-prop-2-enoyloxypropoxy)benzoate Chemical compound C=1C=C(OC(=O)C=2C=CC(OCCCOC(=O)C=C)=CC=2)C(C)=CC=1OC(=O)C1=CC=C(OCCCOC(=O)C=C)C=C1 ISSYGWIDLYOJEN-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
-
- 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
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/08—Mirrors
- G02B5/0808—Mirrors having a single reflecting layer
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The application relates to the field of reflective films, in particular to a liquid crystal composition, a reflective film and a preparation method thereof. A liquid crystal composition comprising: 1) At least one polymerizable liquid-crystalline compound I; 2) At least one polymerizable chiral compound; 3) At least one non-polymerizable chiral compound having a different handedness than the polymerizable chiral compound, 4) an initiator; 5) And (3) a solvent. The application uses non-polymerizable chiral compounds and polymerizable chiral compounds with different handedness, can control racemization degree in the thickness direction by adjusting the proportion of the two chiral compounds and concentration gradient distribution of each chiral compound in the thickness direction, is equivalent to a method for forming concentration gradient and pitch gradient distribution of the chiral compounds, can reach the target reflection peak width in the thickness of a thinner cholesteric film, and simultaneously greatly shortens the crosslinking curing time of the thinner film layer, and improves economic benefit and production efficiency.
Description
Technical Field
The invention relates to the field of reflective films, in particular to a liquid crystal composition, a reflective film and a preparation method thereof.
Background
The wide wave reflecting film manufactured based on the cholesteric liquid crystal material has important application in the fields of display, energy conservation and the like. The control of the pitch gradient of cholesteric liquid crystals to achieve broadband reflection is an important method in the field. Broer et al, in "Wide-band reflective polarizers from cholesteric polymer networks with a pitch gradient",Nature volume 378,pages 467–469(1995), propose the mixing of chiral difunctional unsaturated liquid crystals, nematic unsaturated monofunctional liquid crystals and UV absorbers. The ultraviolet absorber is used for forming a light intensity gradient in the thickness direction of the cholesteric liquid crystal film during UV polymerization, so that the unsaturated difunctional liquid crystal in the area with high upper layer light intensity reacts fast and is more enriched; the unsaturated monofunctional liquid crystal is more enriched in the region with weak light intensity of the lower layer, so that gradient distribution of chiral components is formed in thickness. Similarly, le Li et al, in "Novel Super Broadband Reflective Polarizer", proceedings of SPIE, volume 2873 (1) -Aug 16,1996 describe a gradient distribution method that uses inadequate phase separation to control chiral components. I.e. chiral unsaturated difunctional liquid crystal + non-polymerizable small molecule liquid crystal. During UV polymerization, a light intensity gradient is formed in the thickness direction of the cholesteric film, and the unsaturated difunctional liquid crystal in the area with high light intensity on the upper layer reacts fast and is more enriched; the small molecular liquid crystal which is not polymerized migrates downwards and is concentrated below, so that the gradient distribution of chiral components is formed.
In both of the above methods, a chiral unsaturated difunctional liquid crystal is required. However, there are problems in that, on the one hand, in order to obtain a wide reflection spectrum, a large difference in chiral liquid crystal concentration distribution in the thickness direction is required, so that it is necessary to increase the thickness of the cholesteric liquid crystal layer and to lengthen the UV polymerization time; on the other hand, the liquid crystal material has the problems of complex synthesis process, difficult separation, high cost and the like.
Disclosure of Invention
In view of the problems existing in the prior art, a first aspect of the present invention provides a liquid crystal composition, which is characterized by comprising:
1) At least one polymerizable liquid-crystalline compound I;
2) At least one polymerizable chiral compound;
3) At least one non-polymerizable chiral compound having a different chiral orientation than the polymerizable chiral compound,
4) An initiator;
5) And (3) a solvent.
In one embodiment, the polymerizable liquid crystal compound I is a difunctional polymerizable liquid crystal compound I.
Preferably, the difunctional polymerizable liquid crystalline compound I has the following structure:
wherein A and B are the same or different and are each independently hydrogen or methyl;
SP1 and SP2, which are identical or different, are each independently an alkylene chain of C 1-12;
C1, C2, C3 and C4 are identical or different, each independently selected from-O-, -CO-, -OCO-, -COO-or-OCOO-;
C is selected from-O-, -CO-, -OCO-, -COO-or-OCOO-;
m is 0 or 1;
r is halogen substituted or unsubstituted C 1-6 alkyl chain or CN or halogen;
(b) One or more non-polymerizable small molecule compounds, including at least one compound II, Wherein R1 is-CH 2 -, -Ph-or-cyclohexane-;
r2 is-Ph-COO-, -COO-Ph-, -Ph-OCO-or-OCO-Ph-;
R3 is-COOH, -CN or-SO 3 H;
m is any integer from 0 to 6;
(c) An initiator;
(d) And (3) a solvent.
Further preferred, the difunctional polymerizable liquid crystalline compound I is selected from I-1:4- {4- [3- (prop-2-enoyloxy) propoxy ] benzoyloxy } phenyl 4- [3- (prop-2-enoyloxy) propoxy ] benzoate, I-2:4- (4- [6- (prop-2-enoyloxy) butoxy ] benzoyloxy) phenyl 4- [4- (prop-2-enoyloxy) butoxy ] benzoate, I-3:4- (4- [6- (prop-2-enoyloxy) hexyloxy ] benzoyloxy) phenyl 4- [6- (prop-2-enoyloxy) hexyloxy ] benzoate, I-4: 3-methyl-4- {4- [3- (prop-2-enoyloxy) propoxy ] benzoyloxy } phenyl 4- [3- (prop-2-enoyloxy) propoxy ] benzoate, I-5: 3-methyl-4- {4- [3- (prop-2-enoyloxy) butoxy ] benzoyloxy } phenyl 4- [4- (prop-2-enoyloxy) butoxy ] benzoate, I-6: 3-methyl-4- {4- [3- (prop-2-enoyloxy) hexyloxy ] benzoyloxy } phenyl 4- [6- (prop-2-enoyloxy) hexyloxy ] benzoate, I-7: 3-chloro-4- (4- [6- (prop-2-enoyloxy) hexyloxy ] benzoyloxy) phenyl 4- [6- (prop-2-enoyloxy) hexyloxy ] benzoate, I-8:4- (4- {3- [ (2-methylpropan-2-enoyl) oxy ] propoxy } benzoyloxy) phenyl 4- {3- [ (2-methylpropan-2-enoyl) oxy ] propoxy } benzoate, I-9:4- (4- {3- [ (2-methylpropan-2-enoyl) oxy ] butoxy } benzoyloxy) phenyl 4- {4- [ (2-methylpropan-2-enoyl) oxy ] butoxy } benzoate, I-10:4- (4- {3- [ (2-methylpropan-2-enoyl) oxy ] hexyloxy } benzoyloxy) phenyl 4- {6- [ (2-methylpropan-2-enoyl) oxy ] hexyloxy } benzoate, I-11: 3-methyl-4- (4- {3- [ (2-methylprop-2-enoyl) oxy ] propoxy } benzoyloxy) phenyl 4- {3- [ (2-methylprop-2-enoyl) oxy ] propoxy } benzoate, I-12: 3-methyl-4- (4- {3- [ (2-methylpropan-2-enoyl) oxy ] butoxy } benzoyloxy) phenyl 4- {3- [ (2-methylpropan-2-enoyl) oxy ] butoxy } benzoate, I-13: 3-methyl-4- (4- {3- [ (2-methylprop-2-enoyl) oxy ] hexyloxy } benzoyloxy) phenyl 4- {3- [ (2-methylprop-2-enoyl) oxy ] hexyloxy } benzoate, I-14: propyl 2, 5-bis (4- { [6- (prop-2-enoyloxy) hexyl ] oxy } benzoyloxy) benzoate, I-15: butyl 2, 5-bis (4- { [6- (prop-2-enoyloxy) hexyl ] oxy } benzoyloxy) benzoate, I-16: amyl 2, 5-bis (4- { [6- (prop-2-enoyloxy) hexyl ] oxy } benzoyloxy) benzoate, I-17: hexyl 2, 5-bis (4- { [6- (prop-2-enoyloxy) hexyl ] oxy } benzoyloxy) benzoate, I-18: 5-cyano-2, 5-bis (4- { [6- (prop-2-enoyloxy) hexyl ] oxy } benzoyloxy) benzoate, I-19: 3-chloropropyl 2, 5-bis (4- { [6- (prop-2-enoyloxy) hexyl ] oxy } benzoyloxy) benzoate, I-20:4- {4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] propoxy ] carbonyl ] oxy ] benzoyloxy ] phenyl 4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] propoxy ] oxy ] benzoate, I-21:4- {4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] butoxy ] carbonyl ] oxy ] benzoyl oxy ] phenyl 4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] butoxy ] oxy ] benzoate, I-22:4- {4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] hexoxy ] carbonyl ] oxy ] benzoyloxy ] phenyl 4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] hexoxy ] benzoate, I-23:3-methyl-4- {4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] phenoxy ] phenyl ] oxy ] benzoate, I-23:4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] phenyl ] oxy ] benzoate I-24: 3-methyl-4- {4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] butoxy ] carbonyl) oxy ] benzyloxy ] phenyl 4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] butoxy ] oxy ] benzoate, I-25:3-methyl-4- {4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] hexoxy ] carbonyl) oxy ] benzyl ] phenyl 4- ({ 4- [ (2-methylpropan-2-enoyl) oxy ] hexoxy ] oxy ] benzoate, I-26:4- [4- ({ [4- (prop-2-enoyl) propoxy ] carbonyl } oxy) benzyl ] phenyl 4- ({ [4- (prop-2-enoyl) propoxy ] carbonyl } oxy) benzoate, I-27:4- [4- ({ [4- (prop-2-enoxy) butoxy ] phenyl ] 4- ({ 4- (2-enoxy) oxy) benzoate, I-28:4- [4- ({ [4- (prop-2-enyloxy) hexyloxy ] carbonyl } oxy) benzyloxy ] phenyl 4- ({ [4- (prop-2-enyloxy) hexyloxy ] carbonyl } oxy) benzoate, I-29: 3-methyl-4- {4- [ ({ [6- (prop-2-enyloxy) hexyl ] oxy ] carbonyl) oxy ] benzyloxy ] phenyl 4- [ ({ [6- (prop-2-enyloxy) hexyl ] oxy ] carbonyl ] benzoate, I-30:3-ethyl-4- {4- [ ({ [6- (prop-2-enyloxy) hexyl ] oxy ] carbonyl) oxy ] benzyloxy ] phenyl 4- [ ({ [6- (prop-2-enyloxy) hexyl ] oxy ] carbonyl ] benzoate, I-31:3-methyl-4- [4- ([ 4- (prop-2-enyloxy) butoxy ] carbonyl } oxy) benzyl ] phenyl 4- ([ 4- (prop-2-enyloxy) butoxy ] carbonyl } oxy) benzoate, I-32:3-ethyl-4- [4- ([ 4- (prop-2-enyloxy) butoxy ] carbonyl } oxy) benzyl ] phenyl 4- ([ prop-2-enyloxy) butoxy ] carbonyl } oxy) benzoate.
In one embodiment, the polymerizable chiral compound and the non-polymerizable chiral compound each independently have a structure represented by the formulas (Ch-1) to (Ch-4);
Wherein A 1 and A 2 are each independently 1, 4-phenylene, 1, 4-cyclohexylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, naphthalene-2, 6-diyl, naphthalene-1, 4-diyl, tetrahydronaphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1, 3-dioxane-2, 5-diyl, which groups may be unsubstituted or substituted by more than one substituent, and when a 1 and A 2 are present in plural, they may be the same or different.
For non-polymerizable chiral compounds, Z 1 and Z 2 are each independently -O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-N＝N-、-CH＝N-、-N＝CH-、-CH＝N-N＝CH-、-CF＝CF- or a group represented by a single bond, and when there are a plurality of Z 1 and Z 2, they may be the same or different, and m1 and m2 represent an integer of 0 to 6;
For polymerizable chiral compounds, Z 1 and Z 2 are each independently -O-、-S-、-OCH2-、-CH2O-、-CH2＝CH2-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH2＝CH2-、-OCO-CH2＝CH2-、-CH2＝CH2-COO-、-CH2＝CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH＝CH-、-N＝N-、-CH＝N-、-N＝CH-、-CH＝N-N＝CH-、-CF＝CF-、-C≡C- or a group represented by a single bond, and when there are a plurality of Z 1 and Z 2, they may be the same or different, and m1 and m2 represent an integer of 0 to 6;
For non-polymerizable chiral compounds, R 1、R2 and R 3 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, one of which-CH 2 -or two or more non-adjacent-CH 2 -may each independently be substituted with-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-;
For polymerizable chiral compounds, R 1、R2 and R 3 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, one of the straight-chain or branched alkyl groups-CH 2 -or two non-adjacent groups the above-CH 2 -may each independently be substituted by -O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-CH＝CH-、-CF＝CF- or-C.ident.C-, or R 1、R2 and R 3 each independently represent a group represented by the following formula (Ch-R),
P represents a polymerizable group;
Sp represents a spacer group or a single bond, and when there are a plurality of Sp, they may be the same or different.
X represents -O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH2＝CH2-、-OCO-CH2＝CH2-、-CH2＝CH2-COO-、-CH2＝CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH＝CH-、-N＝N-、-CH＝N-N＝CH-、-CF＝CF-、-C≡C- or a single bond, and when a plurality of X's exist, they may be the same or different;
k represents an integer of 0 to 10.
In a preferred embodiment, the polymerizable chiral compound is selected from the group consisting of,
Wherein W 1 and W 2 are each independently a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group, sp 1 and Sp 2 are each independently an alkylene group having 2 to 18 carbon atoms, and R 1 and R 2 are each a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.
In a preferred embodiment, the non-polymerizable chiral compound is selected from the group consisting of,
Wherein R 1、R2、R3 and R 4 represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group.
In one embodiment, the weight ratio of polymerizable chiral compound to non-polymerizable chiral compound is (19:1) - (1:1) or (1:19) - (1:3).
Preferably, the HTP of the polymerizable chiral compound and the non-polymerizable chiral compound is between 20 and 150 μm -1 (25 ℃), preferably between 40 and 120 μm -1 (25 ℃).
Preferably, the polymerizable chiral compound and the non-polymerizable chiral compound account for 1 to 15wt%, preferably 2 to 12wt%, of the solid content of the liquid crystal composition.
The specific liquid crystal composition of the present application is subjected to UV polymerization at a controlled rate after being coated into a film. Because of the high UV intensity received at the air interface of the cholesteric film, the polymerizable chiral compound preferentially polymerizes and enriches, and the non-polymerizable chiral compound is extruded to migrate downwards after polymerization. As the polymerization time increases, the concentration distribution of the two chiral compounds in the film thickness direction exhibits opposite results: from the air interface to the substrate interface, the concentration of polymerizable chiral compounds becomes lower and the concentration of non-polymerizable chiral compounds becomes higher, exhibiting a distributed gradient of this formula.
The initiator of the present application is not particularly limited, and those skilled in the art can make routine selections as desired.
In one embodiment, the liquid crystal composition further comprises an ultraviolet absorber and/or other auxiliary agents.
The ultraviolet absorber includes, but is not limited to, salicylate type, dibenzo-ketone type ultraviolet absorbers, benzotriazole type ultraviolet absorbers, etc., specifically exemplified are materials such as phenyl salicylate in salicylate type, UV-0 in dibenzo-ketone type, UV-9, UV-531, UV-P, UV-326 in benzotriazole type, UV-328, UV-329, etc., the above ultraviolet absorber can directly absorb ultraviolet rays, the above ultraviolet absorber is used in an amount of 0 to 10% by weight based on the total weight of the liquid crystal composition, preferably in an amount of 0.2 to 4%.
The addition of the ultraviolet absorbent can form a light intensity gradient in the thickness direction of the cholesteric liquid crystal film during the UV polymerization in the composition, thereby being beneficial to forming a concentration gradient of chiral compounds, in addition, the functional layer has better ultraviolet resistance after polymerization, the color-changing functional layer of the daily necessities can not fade, crack, fall off and the like after long-term outdoor use,
Examples of other auxiliary agents in the present application include antioxidants, stabilizers, catalysts, sensitizers, lubricants, and the like.
The solvent in the present application is not particularly limited, and those skilled in the art may make routine selections according to actual needs.
In one embodiment, the liquid crystal composition has a solids content of 10 to 65wt%, preferably 20 to 60wt%.
The invention realizes wide wave cholesteric liquid crystal reflection under the conditions of shorter UV polymerization time and thinner cholesteric liquid crystal layer thickness by using common polymerizable liquid crystal material combination and utilizing the concentration distribution difference and racemization characteristics of chiral materials with different handedness.
The second aspect of the present invention provides a reflective film obtained from the liquid crystal composition.
The third aspect of the present invention provides a method for producing the reflective film, comprising the steps of:
(1) Coating a liquid crystal composition on the surface of a substrate;
(2) Drying the solvent;
(3) And (5) ultraviolet irradiation polymerization.
In the method for preparing the reflective film, the manner of coating in the step (1) is not particularly limited, and a person skilled in the art may make routine selections.
Preferably, the wet thickness of the coating in step (1) is from 10 to 50g/m 2, preferably from 15 to 45g/m 2.
Preferably, in the step (2), the drying condition is 50-120 ℃ and the drying time is 0.5-5min.
Preferably, in step (3), the irradiation light source is UV light, preferably an LED-UV lamp. The wavelength of UV light is 350-450nm. The UV light power is 0.1-60mW/cm 2, the polymerization is carried out under UV light irradiation at 30-90 ℃ for 0.5-5min, and the polymerization energy is 0.2-5J/cm 2.
Compared with the prior art, the invention has the following beneficial effects:
The application uses non-polymerizable chiral compounds and polymerizable chiral compounds with different handedness, can control racemization degree in the thickness direction by adjusting the proportion of the two chiral compounds and concentration gradient distribution of each chiral compound in the thickness direction, is equivalent to a method for forming concentration gradient and pitch gradient distribution of the chiral compounds, can reach the target reflection peak width in the thickness of a thinner cholesteric film, and simultaneously greatly shortens the crosslinking curing time of the thinner film layer, and improves economic benefit and production efficiency. Solves the problems that reasonable pitch gradient distribution cannot be formed in the prior art, and only the thickness and the polymerization time of a cholesteric film can be increased, so that the economic cost and the production efficiency are sacrificed.
In addition, the cholesteric layer obtained by the application has better optical performance and wide raw material sources, avoids the synthesis of chiral nematic liquid crystal molecules, and solves the problems of complex synthesis process, difficult separation, high cost and the like of the liquid crystal material.
Drawings
FIG. 1 is a graph showing the reflectance spectrum during polymerization of the cholesteric liquid crystal film of example 4.
Detailed Description
The present invention is illustrated by the following specific embodiments, but is not limited to the specific examples given below.
The components of the liquid crystal composition are shown in Table 1 below, and the unit is parts by weight.
TABLE 1
Wherein the polymerizable dextrorotatory chiral compound is 4- ({ (3 aR,6 aR) -6- [4- (4- {4- [ (2-methylpropan-2-enoyl) oxy ] butoxy } benzoyloxy ] -hexahydrofuro [3,2-b ] furan-3-yl ] oxy } carbonyl) phenyl 4- { (2-methylpropan-2-enoyl) oxy ] butoxy } benzoate.
The non-polymerizable left-handed chiral compound used was 1- (2- {4- [4- (hexyloxy) phenyl ] benzoyloxy ] naphthalen-1-yl) naphthalen-2-yl 4- [4- (hexyloxy) phenyl ] benzoate.
A reflective film is prepared from the liquid crystal composition.
The preparation method of the reflecting film comprises the following steps:
(1) 60g I-1 g,20 g I-9 g, 10.8g I-23 g, 5.9g of dextrorotatory polymerizable chiral compound, 0.1g of levorotatory non-polymerizable chiral compound and 3g Irgacure369,0.2g BHT g of non-polymerizable chiral compound are weighed respectively, poured into a three-necked flask in sequence, and 100g of cyclohexanone is added. Stirring was carried out at 40℃for 1.5 hours until the mixture was sufficiently dissolved, and the mixture was filtered through a 0.45 μm filter to obtain a liquid crystal composition 1. Similarly, liquid crystal compositions 2 to 8 (corresponding to examples 2 to 8, respectively), and comparative example compositions were formulated.
(2) The liquid crystal composition 1 prepared in example 1 was coated on the surface of a PET film using a slit method to a wet thickness of 16. Mu.m, and after drying the wet film at 80℃for 120 seconds, it was subjected to UV photopolymerization at 50℃under a nitrogen atmosphere for 240 seconds by 2.0mW/cm 2 to obtain a reflective film. Similarly, the reflective films of examples 2 to 8 and comparative examples were obtained.
Performance evaluation
1. Reflection spectrum
Reflection spectra were measured every 20 seconds during cholesteric liquid crystal film polymerization using a marine Ocean6000 fiber spectrometer.
The test results of example 4 are shown in FIG. 1, in which the reflection peak width of the cholesteric liquid crystal film is gradually widened from 60nm to 400nm in 240 seconds.
2. Reflection peak width assessment
Reflection spectra of the reflective films in the 380-750nm range were measured using a Shimadzu 3700 spectrophotometer and the reflection peak width W was calculated and defined as follows:
A：W≥300nm
B：300nm＞W≥250nm
C：250nm＞W≥200nm
D：W<200nm
The larger the W value, i.e. the wider the reflection peak width.
3. Reflectivity evaluation
The reflectance spectrum of the reflective film in the 380-750nm range was measured using a Shimadzu 3700 spectrophotometer and the average reflectance R (%) was calculated and defined as follows:
A：R≥35％
B：35％＞R≥30％
C：30％＞R≥25％
D：R<25％
the larger the R value, the greater the reflectance.
4. Haze degree
Haze (H) is the ratio of the scattered light flux to the transmitted light flux, expressed as a percentage, passing through the sample and deviating from the direction of the incident light. Only scattered light fluxes that deviate by more than 2.5 degrees from the direction of the incident light are typically used to calculate haze. Haze of the reflective film was measured using a haze meter TH-09 of hangzhou color spectrum science and technology limited. And is defined as follows.
A：H≤1.0％
B：1.0％<H≤1.2％
C：1.2％<H≤1.5％
D：＞1.5％
The test results are shown in Table 2.
TABLE 2
* The thickness of the reflective film sample of comparative example 2 was measured to be 12.3um.
Claims (6)
1. A liquid crystal composition comprising:
1) At least one polymerizable liquid-crystalline compound I;
2) At least one polymerizable chiral compound;
3) At least one non-polymerizable chiral compound having a different chiral orientation than the polymerizable chiral compound,
4) An initiator;
5) A solvent;
The polymerizable liquid crystal compound I is selected from I-1:4- {4- [3- (prop-2-enoyloxy) propoxy ] benzoyloxy } phenyl 4- [3- (prop-2-enoyloxy) propoxy ] benzoate, I-9:4- (4- {3- [ (2-methylpropan-2-enoyl) oxy ] butoxy } benzoyloxy) phenyl 4- {4- [ (2-methylpropan-2-enoyl) oxy ] butoxy } benzoate, I-23: 3-methyl-4- {4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] propoxy ] carbonyl) oxy ] benzyl ] phenyl 4- [ ({ 4- [ (2-methylpropan-2-enoyl) oxy ] propoxy ] oxy ] benzoate;
The polymerizable chiral compound is 4- ({ (3 ar,6 ar) -6- [4- (4- {4- [ (2-methylpropan-2-enoyl) oxy ] butoxy } benzoyloxy ] -hexahydrofuro [3, 2-b ] furan-3-yl ] oxy } carbonyl) phenyl 4- { (2-methylpropan-2-enoyl) oxy ] butoxy } benzoate;
The non-polymerizable chiral compound is 1- (2- {4- [4- (hexyloxy) phenyl ] benzoyloxy ] naphthalen-1-yl) naphthalen-2-yl 4- [4- (hexyloxy) phenyl ] benzoate;
The weight ratio of polymerizable chiral compound to non-polymerizable chiral compound is (59:1) - (1:1), or (1:19) - (1:3).
2. The liquid crystal composition according to claim 1, wherein the polymerizable chiral compound and the non-polymerizable chiral compound account for 1 to 15wt% of the solid content of the liquid crystal composition.
3. The liquid crystal composition according to claim 1, wherein the liquid crystal composition has a solid content of 10 to 65wt%.
4. A liquid crystal composition according to claim 3, characterized in that the liquid crystal composition further comprises an ultraviolet absorber and/or other auxiliaries.
5. A reflective film obtained from the liquid crystal composition according to any one of claims 1 to 4.
6. The method of producing a reflective film according to claim 5, comprising the steps of:
(1) Coating a liquid crystal composition on the surface of a substrate;
(2) Drying the solvent;
(3) And (5) ultraviolet irradiation polymerization.
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| CN106483730A (en) * | 2016-12-14 | 2017-03-08 | 北京大学 | A kind of have controllable liquid crystal film of total reflection function and preparation method thereof |
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| CN104142587A (en) * | 2014-07-16 | 2014-11-12 | 北京大学 | Dual-reflection zone cholesteric liquid crystal film with reversible light response characteristic and preparation method for dual-reflection zone cholesteric liquid crystal film |
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