CN110922782A - Dichroic dye and dye-based polarizing film - Google Patents
Dichroic dye and dye-based polarizing film Download PDFInfo
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- CN110922782A CN110922782A CN201911173352.6A CN201911173352A CN110922782A CN 110922782 A CN110922782 A CN 110922782A CN 201911173352 A CN201911173352 A CN 201911173352A CN 110922782 A CN110922782 A CN 110922782A
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- 239000000975 dye Substances 0.000 claims abstract description 129
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- -1 phenylamino, benzoyl Chemical group 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims abstract description 14
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 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 claims abstract 6
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 26
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- UFUQRRYHIHJMPB-DUCFOALUSA-L Sirius red 4B Chemical compound [Na+].[Na+].OS(=O)(=O)c1cc2cc(NC(=O)c3ccccc3)ccc2c([O-])c1\N=N\c1ccc(cc1)\N=N\c1ccc(cc1)S([O-])(=O)=O UFUQRRYHIHJMPB-DUCFOALUSA-L 0.000 claims description 5
- AVERNFJXXRIVQN-XSDYUOFFSA-N 5-[(4-ethoxyphenyl)diazenyl]-2-[(e)-2-[4-[(4-ethoxyphenyl)diazenyl]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C1=CC(OCC)=CC=C1N=NC(C=C1S(O)(=O)=O)=CC=C1\C=C\C1=CC=C(N=NC=2C=CC(OCC)=CC=2)C=C1S(O)(=O)=O AVERNFJXXRIVQN-XSDYUOFFSA-N 0.000 claims description 3
- PBOIUUROGJVVNC-UHFFFAOYSA-L disodium 2-hydroxy-5-[[4-[[2-methoxy-4-[(3-sulfonatophenyl)diazenyl]phenyl]carbamoylamino]phenyl]diazenyl]benzoate Chemical compound [Na+].[Na+].COc1cc(ccc1NC(=O)Nc1ccc(cc1)N=Nc1ccc(O)c(c1)C([O-])=O)N=Nc1cccc(c1)S([O-])(=O)=O PBOIUUROGJVVNC-UHFFFAOYSA-L 0.000 claims description 3
- 238000000862 absorption spectrum Methods 0.000 abstract description 18
- 238000010521 absorption reaction Methods 0.000 abstract description 15
- 238000002360 preparation method Methods 0.000 abstract description 12
- 239000001045 blue dye Substances 0.000 abstract description 9
- 239000010408 film Substances 0.000 description 25
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 230000010287 polarization Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910001385 heavy metal Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 150000001555 benzenes Chemical class 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 230000005856 abnormality Effects 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000011241 protective layer Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- LRSYZHFYNDZXMU-UHFFFAOYSA-N 9h-carbazol-3-amine Chemical compound C1=CC=C2C3=CC(N)=CC=C3NC2=C1 LRSYZHFYNDZXMU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006145 SO3Li Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052730 francium Inorganic materials 0.000 description 1
- KLMCZVJOEAUDNE-UHFFFAOYSA-N francium atom Chemical compound [Fr] KLMCZVJOEAUDNE-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 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 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B19/00—Oxazine dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polarising Elements (AREA)
Abstract
The invention belongs to the technical field of polarizers, and particularly relates to a dichroic dye and a dye-based polarizer. The dichroic dye provided by the invention is used for a dye-based polarizer and comprises at least one of a compound I, a compound II, a compound III and a compound IV; wherein R is1、R2、R3、R4、R6Each independently selected from hydrogen atom, halogen, hydroxyl, alkyl, alkoxy, amino, alkylamino, phenylamino, benzoyl or phenylazo; r5Is selected from hydrogen atom or alkyl; q1、Q2、Q3、Q4Each independently selected from a hydrogen atom, an alkali metal or ammonium; n is selected to be a positive integer of 4 or less. The compounds I-IV have the advantages of wide absorption spectrum, high dichroic ratio and humidity and heat resistance, the maximum absorption wavelength of the compounds is more than 600nm, and the compounds can be used as blue dyes to be applied to preparation of dye-based polarizers.
Description
Technical Field
The invention belongs to the technical field of polarizers, and particularly relates to a dichroic dye and a dye-based polarizer.
Background
A polarizer is a thin film that can pass light vibrating in a specific direction, but hardly pass light vibrating in other vibration directions, and is widely used in LCD liquid crystal displays, polarized sunglasses, OLED displays, and 3D glasses. Currently, there are two main types of polarizers: iodine-based sheets and dye-based polarizers have the advantage of high temperature and high humidity resistance, and compared with iodine-based polarizers, dye-based polarizers are more suitable for being applied to environments with relatively severe conditions such as outdoor, vehicle-mounted, navigation and the like, and therefore are more and more paid attention to in the market.
In the manufacturing process of the dye-based polarizer, a base film of polyvinyl alcohol (PVA) resin needs to use a polarizer high-dichroism dye in a dyeing process, and the currently used dyes are mainly concentrated into polyazo dyes, such as trisazo dyes, which have narrow absorption spectra, generally only 120nm-200 nm. Meanwhile, the dyes have complex structures and higher synthesis difficulty and purification difficulty, for example, heavy metal elements such as copper ions and the like are often required to be introduced in the synthesis process to ensure that the maximum absorption wavelength of the dyes is over 600nm, so that the environment is harmed, and the synthesis cost is high.
Disclosure of Invention
The invention mainly aims to provide a dichroic dye for preparing a dye-based polarizer, so as to solve the problems of narrow absorption spectrum, complex structure and high cost of the existing polyazo dye.
Another object of the present invention is to provide a dye-based polarizer.
In order to achieve the above object, in a first aspect, the present invention provides a dichroic dye for a dye-based polarizer, comprising at least one of a compound i, a compound ii, a compound iii, and a compound iv:
wherein R is1、R2、R3、R4、R6Each independently selected from hydrogen atom, halogen, hydroxyl, alkyl, alkoxy, amino, alkylamino, phenylamino, benzoyl or phenylazo;
R5is selected from hydrogen atom or alkyl;
Q1、Q2、Q3、Q4each independently selected from a hydrogen atom, an alkali metal or ammonium;
n is selected to be a positive integer of 4 or less.
In a second aspect, a dye-based polarizer includes: a film of a polyvinyl alcohol resin or a derivative thereof, and the film of the polyvinyl alcohol resin or the derivative thereof contains a dichroic dye including the above-mentioned dichroic dye.
The dichroic dye provided by the invention comprises at least one of a compound I, a compound II, a compound III and a compound IV, the compounds I-IV have the advantages of wide absorption spectrum, high dichroic ratio and humidity resistance, the maximum absorption wavelength of the dichroic dye is more than 600nm, and the dichroic dye can be used as a blue dye for preparing a dye-based polarizer. Compared with the existing trisazo dyes, the compounds I-IV have simple structure, are easy to synthesize and purify, do not need to introduce heavy metal elements during synthesis, and do not pollute the environment.
Accordingly, the present invention provides a dye-based polarizer, wherein a film of a polyvinyl alcohol resin or a derivative thereof contains a dichroic dye, and the dichroic dye is the above dichroic dye, and the dichroic dye has advantages of wide absorption spectrum, high dichroic ratio, humidity and heat resistance, green safety, and the like, such that the obtained polarizer has high transmittance and high polarization degree, and humidity and heat resistance.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
A dichroic dye for a dye-based polarizer, comprising at least one of a compound I, a compound II, a compound III and a compound IV:
wherein R is1、R2、R3、R4、R5、R6Each independently selected from hydrogen atom, halogen, hydroxyl, alkyl, alkoxy, amino, alkylamino, phenylamino, benzoyl or phenylazo;
R5is selected from hydrogen atom or alkyl;
Q1、Q2、Q3、Q4each independently selected from a hydrogen atom, an alkali metal or ammonium;
n is selected to be a positive integer of 4 or less.
In the present specification, the compounds and derivatives thereof are named according to the IUPAC (international union of pure and applied chemistry) or CAS (chemical abstracts service, colombia, ohio) naming system, and the groups of the compounds are specifically described and illustrated as follows:
"halogen" refers to elements of group VIIA of the periodic Table of the elements, including chlorine (Cl), bromine (Br), iodine (I), and the like.
"hydroxyl" refers to a group consisting of one oxygen atom and one hydrogen atom, denoted as-OH.
"alkyl" refers to a class of saturated hydrocarbon radicals containing only two atoms of carbon and hydrogen, including chain alkyl or cycloalkyl radicals, including but not limited to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl, and the like. In the examples of the present invention, the number of carbon atoms of the alkyl group is preferably 1 to 10, and in specific embodiments, the number of carbon atoms of the alkyl group is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
"alkoxy" refers to a class of alkyl groups directly bonded to an oxygen atom, including but not limited to, methoxy, ethoxy, propoxy, butoxy, isobutoxy, t-butoxy, and the like. In the present embodiment, the number of carbon atoms of the alkoxy group is preferably 1 to 10, and in a specific embodiment, the number of carbon atoms of the alkoxy group is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
"amino" refers to a group consisting of one nitrogen atom and two hydrogen atoms, represented by-NH2。
"ammonium" refers to a group consisting of one nitrogen atom and four hydrogen atoms, denoted NH4 +。
"alkylamino" refers to a class of alkyl groups directly bonded to a secondary or tertiary amino group, including, but not limited to, for example, methylamino, ethylamino, propylamino, butylamino, and the like. In the examples of the present invention, the number of carbon atoms of the alkylamino group is preferably 1 to 10, and in specific embodiments, the number of carbon atoms of the alkylamino group is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
"phenylamino" refers to a class of phenyl groups directly bonded to a secondary or tertiary amino group, the phenyl groups being optionally substituted or unsubstituted benzene, the substituents of which include, but are not limited to, sulfonic acid groups, amino groups, hydroxyl groups, and alkyl groups having from 1 to 8 carbon atoms. In the examples of the present invention, the number of carbon atoms of the phenylamino group is preferably 1 to 20, and in specific embodiments, the number of carbon atoms of the phenylamino group is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.
"benzoyl" refers to a group of phenyl groups bonded directly to a carbonyl group, the phenyl groups being optionally substituted or unsubstituted benzene, the substituents of the substituted benzene including, but not limited to, sulfonic acid groups, amino groups, hydroxyl groups, and alkyl groups having 1 to 8 carbon atoms. In the present embodiment, the number of carbon atoms of the benzoyl group is preferably 1 to 20, and in a specific embodiment, the number of carbon atoms of the benzoyl group is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.
"phenylazo" refers to a group of phenyl groups directly bonded to an azo group (-N ═ N-), the phenyl groups being optionally substituted or unsubstituted benzene, the substituents for substituted benzene including, but not limited to, sulfonic acid groups, amino groups, hydroxyl groups, and alkyl groups having 1 to 8 carbon atoms. In the present embodiment, the number of carbon atoms of the phenylazo group is preferably 1 to 20, and in a specific embodiment, the number of carbon atoms of the phenylazo group is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.
"alkali metal" refers to six metallic elements in group IA of the periodic Table of the elements, i.e., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), francium (Fr), in addition to hydrogen (H). In the present embodiment, the alkali metal is preferably Li, Na or K.
Specifically, compound i has the following general formula:
wherein R is1Selected from hydrogen atom, halogen, hydroxyl, alkyl, alkoxy, amino, alkylamino, phenylamino, benzoyl or phenylazo;
Q1selected from hydrogen atoms, alkali metals or ammonium;
n is selected to be 1, 2, 3 or 4.
In the compound I, a condensed ring aromatic hydrocarbon ring with rigidity is taken as a mother nucleus, a heteroatom N, O is introduced to improve the maximum absorption wavelength of a molecule, and a hydrophilic group such as-SO is introduced on the basis of the heteroatom3H、-SO3Na、-SO3K、-SO3Li and the like are used for improving the dispersibility of the compound in water or a solvent and enabling the compound to have uniform dyeing characteristics, so that the compound I has the advantages of wide absorption spectrum, high dichroic ratio and humidity and heat resistance, the maximum absorption wavelength is more than 600nm, and the compound can be used as a blue dye for preparing dye-based polaroids. Compared with the existing trisazo dye, the compound I has simple structure, is easy to synthesize and purify, does not need to introduce heavy metal elements during synthesis, and does not pollute the environment.
As an embodiment, the R is1Selected from F, Cl or Br, the Q1Is selected from H, Na orK, and n is 2-4. The absorption spectrum width of the compound is about 520nm-730nm through detection, and the maximum absorption peak wavelength is more than 600 nm.
Specifically, compound ii has the following general formula:
wherein R is2And R3Each independently selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, amino, alkylamino, phenylamino, benzoyl or phenylazo;
Q2selected from hydrogen atoms, alkali metals or ammonium;
n is selected to be 1, 2, 3 or 4.
As above, the compound II has the advantages of wide absorption spectrum, high dichroic ratio and humidity and heat resistance, and the maximum absorption wavelength is more than 600nm, so that the compound II can be used as a blue dye for preparing dye-based polaroids. Compared with the existing trisazo dye, the compound II has simple structure, is easy to synthesize and purify, does not need to introduce heavy metal elements during synthesis, and does not pollute the environment.
As an embodiment, the R is2Selected from F, Cl or Br, the R3Selected from phenylamino, benzoyl or phenylazo, said Q2Selected from H, Na or K, and n is 2-4. The absorption spectrum width of the compound is about 500nm-700nm through detection, and the maximum absorption peak wavelength is more than 600 nm.
As an embodiment, the compound ii includes at least one of the following compounds:
the absorption spectrum widths of the compound II 1 and the compound 2 are detected to be about 500nm-700nm, and the maximum absorption peak wavelength is 600 nm. In some embodiments, even if the compound is used alone as a dichroic dye to dye a PVA film, the prepared polarizer can completely absorb light of 500nm-700nm, and the dye is remarkably superior to the existing polyazo dyes.
Specifically, compound iii has the following general formula:
wherein R is4And R5Each independently selected from hydrogen, halogen, hydroxy, alkyl, alkoxy, amino, alkylamino, phenylamino, benzoyl or phenylazo;
Q3selected from hydrogen atoms, alkali metals or ammonium;
n is selected to be 1, 2, 3 or 4.
As above, the compound III has the advantages of wide absorption spectrum, high dichroic ratio and humidity and heat resistance, and the maximum absorption wavelength is more than 600nm, so that the compound III can be used as a blue dye for preparing dye-based polaroids. Compared with the existing trisazo dyes, the compound III has simple structure, is easy to synthesize and purify, does not need to introduce heavy metal elements during synthesis, and does not pollute the environment.
As an embodiment, the R is4Selected from F, Cl or Br, the R5Is selected from hydrogen atom or alkyl, the Q3Selected from H, Na or K, and n is 2-4. The absorption spectrum width of the compound is about 520nm-700nm through detection, and the maximum absorption peak wavelength is more than 600 nm.
As an embodiment, the compound iii includes at least one of the following compounds:
the absorption spectrum width of the compound is detected to be about 520nm-700nm, and the maximum absorption peak wavelength is 605 nm. In some embodiments, even if the compound is used alone as a dichroic dye to dye a PVA film, the prepared polarizer can completely absorb light with the wavelength of 520nm-700nm, and the prepared polarizer is remarkably superior to the existing polyazo dyes.
Specifically, compound iv has the following general formula:
wherein R is6Selected from hydrogen atom, halogen, hydroxyl, alkyl, alkoxy, amino, alkylamino, phenylamino, benzoyl or phenylazo;
Q4selected from hydrogen atoms, alkali metals or ammonium;
n is selected to be 1, 2, 3 or 4.
As above, the compound IV has the advantages of wide absorption spectrum, high dichroic ratio and humidity and heat resistance, and the maximum absorption wavelength is more than 600nm, so that the compound IV can be used as a blue dye for preparing dye-based polaroids. Compared with the existing trisazo dyes, the compound IV has simple structure, is easy to synthesize and purify, does not need to introduce heavy metal elements during synthesis, and does not pollute the environment.
As an embodiment, the R is6Selected from F, Cl or Br, the Q4Selected from H, Na or K, and n is 2-4. The absorption spectrum width of the compound is about 490nm-700nm through detection, and the maximum absorption peak wavelength is above 600 nm.
As an embodiment, the compound iv includes at least one of the following compounds:
wherein, R is6Selected as F, Cl or Br.
In embodiments of the present invention, the dichroic dye may comprise more than one compound, optionally a combination of dye compounds.
As an embodiment, the dichroic dye is selected from at least one of the following compounds:
wherein, R is6Selected as F, Cl or Br.
In some embodiments, the dichroic dye comprises compound ii 1 and/or compound iii 1.
In some embodiments, the dichroic dye comprises: a compound II 1 and/or a compound III 1, and a compound II 2 and/or a compound IV 1.
In some embodiments, the dichroic dye comprises: a compound II 2 and/or a compound IV 1.
Further, the dichroic dye may be a combination of at least one of the compound i, the compound ii, the compound iii, and the compound iv with other dyes, in addition to the compound i, the compound ii, the compound iii, or the compound iv.
As an embodiment, the dichroic dye further includes other dyes; such other dyes include: at least one of direct yellow 12, direct yellow 44, direct orange 39, direct orange 107, direct red 81, direct red 147, and direct red 247. By the combination, the absorption spectrum of the dichroic dye can be flexibly adjusted, so that the prepared polarizing film can meet the requirement of wide color spectrum.
Wherein, the compounds II 1, II 2, III 1 and IV 1 can be selected from commercial products and products synthesized by adopting the conventional technical means in the field. In some embodiments, the preparation of compound ii 1 comprises: taking 0.5mol of 4-aminodiphenylamine disulfonic acid and 0.25mol of chloranil to carry out thermal reflux in 1000ml of water, and carrying out condensation reaction by taking magnesium oxide as an acid-binding agent to obtain a product, taking concentrated sulfuric acid (98%) as a solvent, and carrying out ring-closure reaction at the reaction temperature of 160 ℃. In some embodiments, the preparation of compound iii 1 comprises: taking 0.5mol of 3-aminocarbazole and 0.25mol of tetrachlorobenzoquinone for condensation, taking toluene as a solvent for reflux, taking magnesium oxide as an acid-binding agent for condensation reaction for 10h, heating the obtained intermediate in p-toluenesulfonyl chloride and nitrobenzene at 207 ℃ for ring-closure reaction for 5h, carrying out disulfonation reaction on the obtained product by fuming sulfuric acid, adjusting the pH to 3 after sulfonation at 110 ℃, and carrying out isolation.
In conclusion, the dichroic dye provided by the invention comprises at least one of the compound I, the compound II, the compound III and the compound IV, the compounds I-IV have the advantages of wide absorption spectrum, high dichroic ratio and humidity and heat resistance, the maximum absorption wavelength of the dichroic dye is more than 600nm, and the dichroic dye can be used as a blue dye for preparing a dye-based polarizer. Compared with the existing trisazo dyes, the compounds I-IV have simple structure, are easy to synthesize and purify, do not need to introduce heavy metal elements during synthesis, and do not pollute the environment.
Based on the above-mentioned dichroic dye, the embodiment of the present invention further provides a dye-based polarizer.
Accordingly, a dye-based polarizer includes: a film of a polyvinyl alcohol resin or a derivative thereof, and the film of the polyvinyl alcohol resin or the derivative thereof contains a dichroic dye including the above-mentioned dichroic dye.
The dye-based polarizer provided by the embodiment of the invention has the advantages that the film of the polyvinyl alcohol resin or the derivative thereof contains the dichromatic dye, the dichromatic dye is the dichromatic dye, the dichromatic dye has the advantages of wide absorption spectrum, high dichroism ratio, humidity and heat resistance, green safety and the like, and the obtained polarizer has high transmittance and high polarization degree and humidity and heat resistance.
The structure of the dye-based polarizer may refer to a conventional dye-based polarizer in the art, for example, in some embodiments, a film of polyvinyl alcohol resin or a derivative thereof is used as a substrate, and a protective layer is disposed on one side or both sides of the film of polyvinyl alcohol resin or a derivative thereof.
The preparation method of the dye-based polarizer may refer to conventional processes in the art, and as some embodiments, the preparation method of the dye-based polarizer includes: swelling a film of a polyvinyl alcohol resin or a derivative thereof; subjecting the film of the polyvinyl alcohol resin or the derivative thereof to a dyeing step after the swelling step; a stretching step after the dyeing step; a protective layer is attached to one or both surfaces of the stretched film of the polyvinyl alcohol resin or the derivative thereof.
As one embodiment, the method for preparing the dye-based polarizer includes the steps of:
s01, providing a dichroic dye that is at least one of compound i, compound ii, compound iii, and compound iv, and in combination with other dyes such as direct yellow 12, direct yellow 44, direct orange 39, direct orange 107, direct red 81, direct red 147, direct red 247, etc.; dissolving a dichroic dye, and adjusting the pH value to 6-9 to obtain a dye solution;
s02, sequentially cleaning and swelling the film of the polyvinyl alcohol resin or the derivative thereof, dyeing by using the dye solution prepared in the step S01, and then stretching according to the stretching magnification of 1-6 times to obtain a PVA film;
and S03, attaching a protective layer, such as TAC, to one side or both sides of the PVA film to obtain the polarizer.
Wherein, the concentration of the dichroic dye in the dye solution can be flexibly adjusted according to the actual requirements of products. In some embodiments, the dichroic dye comprises: compound ii 1, or a combination of compound ii 1 with direct red No. 81 and direct orange No. 39; wherein the concentration of the compound II 1 in the dye solution is 0.15 wt%. In some embodiments, the dichroic dye comprises: compound iii 1, or a combination of compound iii 1 with direct red No. 81 and direct orange No. 39; wherein the concentration of the compound III 1 in the dye solution is 0.18 wt%.
In order that the above-described implementation details and operations of the present invention can be clearly understood by those skilled in the art, and the improved performance of a dichroic dye and a dye-based polarizer according to the embodiments of the present invention will be remarkably embodied, the implementation of the present invention will be exemplified by the following examples.
Example 1
The embodiment provides a dye-based polarizer, and a preparation method thereof comprises the following steps:
(1) synthesis of Compound II 1
Taking 0.5mol of 4-aminodiphenylamine disulfonic acid and 0.25mol of chloranil to carry out thermal reflux in 1000ml of water, and carrying out condensation reaction by taking magnesium oxide as an acid-binding agent to obtain a product, taking concentrated sulfuric acid (98%) as a solvent, and carrying out ring-closure reaction at the reaction temperature of 160 ℃ to obtain a compound II 1.
(2) Preparation of PVA film
Taking the compound II 1 prepared in the step (1) as a blue dye, dissolving the blue dye in deionized water, adjusting the pH to 7.5 by adopting sodium hydroxide or hydrochloric acid, and preparing a dye solution with the mass percentage concentration of 0.15%;
the film of polyvinyl alcohol resin or its derivative is sequentially washed in a washing tank, swollen in a swelling tank containing boric acid, dyed in a dyeing tank containing the dye solution prepared in the above step, and then stretched at a stretch ratio of 5 times to obtain a PVA film.
(3) Preparation of dye-based polarizing plate
And attaching a protective layer TAC to one side or two sides of the PVA film to obtain the polarizer.
The polarizer prepared in the embodiment was subjected to transmittance, polarization degree and heat resistance tests, and the transmittance was 47% and the polarization degree was 82%, and no abnormality was observed for 500 hours in an oven with humidity of 85% and temperature of 85%.
Example 2
This example provides a dye-based polarizer, and the preparation method thereof is different from that of example 1 in that: in the step of preparing the PVA film, compounds II 1, No. 81 direct red and No. 39 direct orange are dissolved in the dye solution, and the concentration of the compound II 1 is 0.15 percent, the concentration of the No. 81 direct red is 0.2 percent, and the concentration of the No. 39 direct orange is 0.08 percent; the rest of the process is basically the same as that of embodiment 1, and the description thereof is omitted.
The polarizer prepared in the embodiment is subjected to transmittance, polarization degree and heat resistance tests, and the transmittance is 42%, the polarization degree is 98%, and no abnormality occurs after the test for 500 hours in an oven with humidity of 85% and temperature of 85%.
Example 3
This example provides a dye-based polarizer, and the preparation method thereof is different from that of example 1 in that: the compound III 1 with the mass percent concentration of 0.15% is dissolved in the material solution, and the preparation of the compound III 1 comprises the following steps: condensing 0.5mol of 3-aminocarbazole and 0.25mol of tetrachlorobenzoquinone, refluxing toluene as a solvent, carrying out condensation reaction for 10h by taking magnesium oxide as an acid-binding agent, heating the obtained intermediate in p-toluenesulfonyl chloride and nitrobenzene (207 ℃) to carry out ring-closure reaction for 5h, carrying out disulfonation reaction on the obtained product by using fuming sulfuric acid, adjusting the pH to 3 after sulfonation at the sulfonation temperature of 110 ℃, and carrying out isolation; the rest of the process is basically the same as that of embodiment 1, and the description thereof is omitted.
The polarizer prepared in the embodiment is subjected to transmittance, polarization degree and heat resistance tests, and the transmittance is 52%, the polarization degree is 80%, and no abnormality occurs after the test in an oven with humidity of 85% and temperature of 85% for 500 h.
Example 4
This example provides a dye-based polarizer, and the preparation method thereof is different from that of example 1 in that: in the step of preparing the PVA film, compounds iii 1, direct red 81 and direct orange 39 are dissolved in the dye solution, and the concentration of compound iii 1 is 0.18%, the concentration of direct red 81 is 0.2%, and the concentration of direct orange 39 is 0.08%; the rest of the process is basically the same as that of embodiment 1, and the description thereof is omitted.
The polarizer prepared in the embodiment was subjected to transmittance, polarization degree and heat resistance tests, and the transmittance was 41.5%, the polarization degree was 99%, and no abnormality was observed for 500 hours in an oven with humidity of 85% and temperature of 85%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. A dichroic dye for a dye-based polarizer, comprising at least one of a compound I, a compound II, a compound III and a compound IV:
wherein R is1、R2、R3、R4、R6Each independently selected from hydrogen atom, halogen, hydroxyl, alkyl, alkoxy, amino, alkylamino, phenylamino, benzoyl or phenylazo;
R5is selected from hydrogen atom or alkyl;
Q1、Q2、Q3、Q4each independently selected from a hydrogen atom, an alkali metal or ammonium;
n is selected to be a positive integer of 4 or less.
2. The dichroic dye according to claim 1, wherein the compound ii comprises at least one of the following compounds:
3. the dichroic dye according to claim 1, wherein said compound iii is selected from:
4. the dichroic dye according to claim 1, wherein said compound iv is selected from:
wherein, R is6Selected as F, Cl or Br.
5. The dichroic dye according to claim 1, wherein the dichroic dye is selected from at least one of the following compounds:
wherein, R is6Selected as F, Cl or Br.
6. The dichroic dye according to claim 5, wherein the dichroic dye comprises compound II 1 and/or compound III 1.
7. The dichroic dye according to claim 5, wherein the dichroic dye comprises: a compound II 1 and/or a compound III 1, and a compound II 2 and/or a compound IV 1.
8. The dichroic dye according to claim 5, wherein the dichroic dye comprises: a compound II 2 and/or a compound IV 1.
9. The dichroic dye according to any one of claims 1 to 8, wherein the dichroic dye further comprises other dyes;
such other dyes include: at least one of direct yellow 12, direct yellow 44, direct orange 39, direct orange 107, direct red 81, direct red 147, and direct red 247.
10. A dye-based polarizer comprising: a film of a polyvinyl alcohol resin or a derivative thereof, and the film of the polyvinyl alcohol resin or the derivative thereof contains a dichroic dye, characterized in that the dichroic dye comprises the dichroic dye according to any one of claims 1 to 9.
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| JPS61275703A (en) * | 1985-05-09 | 1986-12-05 | Sumitomo Chem Co Ltd | Highly durable polarizing film |
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| CN103207522A (en) * | 2012-01-11 | 2013-07-17 | 东洋油墨Sc控股株式会社 | Color composition for color filter and color filter |
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| JPS61275703A (en) * | 1985-05-09 | 1986-12-05 | Sumitomo Chem Co Ltd | Highly durable polarizing film |
| CN1218557A (en) * | 1996-04-15 | 1999-06-02 | 奥普蒂瓦公司 | Liquid crystal display and method |
| CN1902529A (en) * | 2004-01-14 | 2007-01-24 | 光学转变公司 | Polarizing devices and methods of making the same |
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