CN110194901A - A kind of preparation method and optical diaphragm of dyestuff - Google Patents
A kind of preparation method and optical diaphragm of dyestuff Download PDFInfo
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- CN110194901A CN110194901A CN201910405059.1A CN201910405059A CN110194901A CN 110194901 A CN110194901 A CN 110194901A CN 201910405059 A CN201910405059 A CN 201910405059A CN 110194901 A CN110194901 A CN 110194901A
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- alkane
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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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
- 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
-
- 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
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Abstract
The present invention provides the preparation method and optical diaphragm of a kind of dyestuff, the preparation method of the dyestuff includes: that dye stuff of rhodamine kinds is added in thionyl chloride to react, the first reaction solution is obtained, and the thionyl chloride in first reaction solution is removed, obtains the first reactant;First reactant, acrylic acid 4- hydroxyl R ester are added in anhydrous tetrahydro furan and reacted, the second reaction solution is obtained;By the anhydrous tetrahydro furan removal in second reaction solution, the second reactant is obtained;Second reactant is washed using methylene chloride and methanol, and used chromatography post separation, obtains dye monomer.The preparation method and optical diaphragm of dyestuff of the invention can be improved the thermal stability of dyestuff, and then reduce the luminance loss of display.
Description
[technical field]
The present invention relates to field of display technology, more particularly to the preparation method and optical diaphragm of a kind of dyestuff.
[background technique]
With the development of display technology, the colour gamut of display is also constantly being promoted.High colour gamut means that display can be shown
More colourful color is shown, there is stronger color to show ability, occur during display to be effectively prevented from
The case where distortion and color lump.Since the type of color increases, so that the color switching of picture can be more naturally, make in display
The level for obtaining picture is more clearly demarcated, can show more details and closer true effect.
For liquid crystal display, since screen itself does not have spontaneous light attribute, promotes colour gamut and mainly pass through three originals
The color fim filter of color (red, green, blue) is realized;In addition it is also possible to carry out the promotion of colour gamut by the adjustment of backlight, at present
There are two types of the main modes for promoting backlight purity: using the backlight of blue led and red green fluorescence material;Using quantum dot (QD)
Backlight technology.
However, due to not purified to red green blue tricolor light during promoting colour gamut, namely exist dark green
Light and yellow orange light, therefore above two colour gamut method for improving makes the red green blue tricolor light finally issued impure.With
The promotion of colour gamut, penetrating for light also decline therewith, to be difficult to realize realize the promotion of brightness while colour gamut is promoted.
Although being absorbed at present by rhodamine material to the veiling glare except RGB, dye stuff of rhodamine kinds is most
There is an acromion on the left of big absorption peak, the blue and green light of part can be absorbed, since dye stuff of rhodamine kinds is easy to produce reunion,
Cause the influx and translocation of acromion, and green portions directly affect penetrance, so as to cause penetrance decline.
Therefore, it is necessary to the preparation method and optical diaphragm of a kind of dyestuff be provided, to solve to ask present in the prior art
Topic.
[summary of the invention]
The purpose of the present invention is to provide a kind of preparation method of dyestuff and optical diaphragms, can improve primaries
While purity, brightness is improved.
In order to solve the above technical problems, the present invention provides a kind of preparation method of dyestuff comprising:
Dye stuff of rhodamine kinds is added in thionyl chloride and is reacted, the first reaction solution is obtained;
By the thionyl chloride removal in first reaction solution, the first reactant is obtained;
First reactant, acrylic acid 4- hydroxyl R ester are added in anhydrous tetrahydro furan and reacted, the second reaction is obtained
Liquid;
By the anhydrous tetrahydro furan removal in second reaction solution, the second reactant is obtained;
Second reactant is washed using methylene chloride and methanol, and used chromatography post separation, obtains dyestuff
Monomer.
The present invention also provides a kind of optical diaphragms, optical film layer, material includes dye monomer, resin, photoinitiator;
The dye monomer includes:
Wherein R6Structure include linear paraffin, the alkane for having branch, the straight chain of alkoxy, branch alkane, contain ester
The chain object of base, F alkane substitute derivative, the conjugated structure being connected by alkoxy and ester group and containing the change of heterocycle
Close at least one of object;The range of carbon chain lengths in the F alkane substitute derivatives group is 1~30.
The preparation method and optical diaphragm of dyestuff of the invention, it is anti-in thionyl chloride by the way that dye stuff of rhodamine kinds to be added
It answers, obtains the first reaction solution, and the thionyl chloride in first reaction solution is removed, obtain the first reactant;By institute
State the first reactant, acrylic acid 4- hydroxyl R ester is added in anhydrous tetrahydro furan and reacts, obtain the second reaction solution, and by described the
Anhydrous tetrahydro furan removal in two reaction solutions, obtains the second reactant;Using methylene chloride and methanol to described second
Reactant is washed, and used chromatography post separation, obtains dye monomer.Due to carrying out singulation to dye stuff of rhodamine kinds, and
The stability of dye stuff of rhodamine kinds after singulation is stronger, to avoid that polymerization reaction occurs, reduces and absorbs energy that is blue, filtering
Amount improves brightness while improving the purity of primaries.
[Detailed description of the invention]
Fig. 1 is the structural schematic diagram of optical diaphragm of the invention.
[specific embodiment]
The explanation of following embodiment is to can be used to the particular implementation of implementation to illustrate the present invention with reference to additional schema
Example.The direction term that the present invention is previously mentioned, such as "upper", "lower", "front", "rear", "left", "right", "inner", "outside", " side "
Deng being only the direction with reference to annexed drawings.Therefore, the direction term used be to illustrate and understand the present invention, rather than to
The limitation present invention.The similar unit of structure is to be given the same reference numerals in the figure.
The preparation method of dyestuff of the invention includes:
S101, dye stuff of rhodamine kinds is added in thionyl chloride and is reacted, obtain the first reaction solution;
For example, in one embodiment, thionyl chloride SOCl is added in dye stuff of rhodamine kinds2In solvent, make the two pre-
If a period of time is reacted at a temperature of, obtains the first reaction solution.
S102, the thionyl chloride in first reaction solution is removed, obtains the first reactant.
The thionyl chloride solvent in first reaction solution is removed by vacuum distillation later, obtains the first reaction
Object.It should be understood that the mode of removal thionyl chloride solvent can be other modes, it is not limited to vacuum distillation mode.
Wherein, the molar range of the dye stuff of rhodamine kinds is 15mmol -30mmol.
Wherein, the range of capacity of the thionyl chloride is 20ml -60ml.
Wherein, the molar range of the acrylic acid 4- hydroxyl R ester is 10mmol -40mmol.
Wherein, the range of capacity of the anhydrous tetrahydro furan is 50ml -150ml.
The temperature range that the dye stuff of rhodamine kinds is reacted with the thionyl chloride is 80 DEG C -100 DEG C, preferably 90 DEG C.
For example, the dye stuff of rhodamine kinds includes rhodamine B, rhodamine 6G, rhodamine 19, Rhodamine 101 and Luo Dan
Bright 110 at least one of derivative, the chemical structural formula of the derivative of rhodamine 6G are as follows:
The chemical structural formula of the derivative of rhodamine 19 is as follows:
The chemical structural formula of the derivative of Rhodamine 101 is as follows:
The chemical structural formula of the derivative of rhodamine 110 is as follows:
Wherein X- includes but is not limited to F-, Cl-, Br-, CF3SO3-、CF2HSO3And CFH2SO3-;Wherein R1~R5And
R7~R11Structure include linear paraffin, the alkane for having branch, the straight chain of alkoxy, the alkane of branch, the chain containing ester group
In shape object, F alkane substitute derivative, the conjugated structure being connected by alkoxy and ester group and compound containing heterocycle
At least one;The range of carbon chain lengths in the F alkane substitute derivatives group is 1~30;
R7It may also include but be not limited to F, Cl, Br, I and CN substituent group;
R8~R11It further include at least one of-F ,-Cl ,-Br and-I substituent group and including amino-NH2, carboxylic
Base-COOH, hydroxyl-OH, sulfate-SH, aldehyde root-COH, ester-COO-, acyl group-COCl ,-COBr, nitrile-CN, nitro-NO2, ammonia
Base-NH2At least one of ,=NH, ≡ N, benzene and phenol ring.
Namely R1~R5And R7~R11Structure can be unconjugated structure (linear paraffin, or have the alkane of branch
Hydrocarbon, the alkane of the straight chain of alkoxy or branch, the chain object containing ester group;F alkane substitute derivative, the model of carbon chain lengths
Enclosing can be 1~30 equal length and differs), R1~R5Be also possible to the conjugated structure being connected by alkoxy and ester group or
Compound containing heterocycle.Heterocyclic compound can be five yuan and hexa-member heterocycle and Benzoheterocyclic compounds etc..Five-ring heterocycles
Closing object includes but is not limited to furans, thiophene, pyrroles, thiazole, imidazoles etc.;6-membered heterocyclic compound includes but is not limited to pyridine, pyrrole
Piperazine, pyrimidine, pyridazine etc. and fused ring heterocycle compound: indoles, quinoline, pteridine, acridine etc..
S103, first reactant, acrylic acid 4- hydroxyl R ester are added in anhydrous tetrahydro furan and reacted, obtain second
Reaction solution;
It is reacted for example, first reactant, acrylic acid 4- hydroxyl R ester are added in anhydrous tetrahydro furan, is setting it
Determine reaction at temperature and obtains the second reaction solution for a period of time.
S104, the anhydrous tetrahydro furan in second reaction solution is removed, obtains the second reactant;
For example, cleaning second reaction solution with saturated brine, and the second reaction solution is washed with saturated sodium bicarbonate solution,
To remove the anhydrous tetrahydro furan, the second reactant is obtained.
Wherein, the chemical structural formula of the acrylic acid 4- hydroxyl R ester is as follows:
Wherein R6Structure include linear paraffin, the alkane for having branch, the straight chain of alkoxy, branch alkane, contain ester
The chain object of base, F alkane substitute derivative, the conjugated structure being connected by alkoxy and ester group and containing the change of heterocycle
Close at least one of object;The range of carbon chain lengths in the F alkane substitute derivatives group is 1~30.
S105, second reactant is washed using methylene chloride and methanol, and used chromatography post separation, is obtained
Dye stuff of rhodamine kinds monomer.
For example, using methylene chloride DCM: methanol MeOH detergent washs the second reactant, and used chromatographic column
Available dye monomer is separated, which is dye stuff of rhodamine kinds monomer.
The dye monomer includes:
Wherein R6Structure include linear paraffin, the alkane for having branch, the straight chain of alkoxy, branch alkane, contain ester
The chain object of base, F alkane substitute derivative, the conjugated structure being connected by alkoxy and ester group and containing the change of heterocycle
Close at least one of object;The range of carbon chain lengths in the F alkane substitute derivatives group is 1~30.
Wherein, the volume ratio of the methylene chloride and the methanol is 1:2.
By taking rhodamine B as an example, the preparation method of above-mentioned dyestuff is specifically included:
S201, thionyl chloride SOCl is added in rhodamine B2In solvent, both make to react 6 hours at 90 DEG C, obtains the
One reaction solution;The thionyl chloride solvent in first reaction solution is removed by vacuum distillation later, it is anti-to obtain first
Answer object.
Wherein the chemical structural formula of rhodamine B is as follows:
S202, first reactant, acrylic acid 4- hydroxyl R ester are added in anhydrous tetrahydro furan and reacted, make it 20
It is reacted at DEG C for 24 hours, obtains the second reaction solution;
S203, second reaction solution is cleaned with saturated brine, and wash the second reaction solution with saturated sodium bicarbonate solution,
To remove the anhydrous tetrahydro furan, the second reactant is obtained.
S204, using methylene chloride DCM: methanol MeOH detergent washs the second reactant, and used chromatographic column
Isolated rhdamine B monomer.
The simplification chemical equation of above-mentioned S201 to S204 is as follows:
The present invention also provides a kind of optical diaphragms comprising optical film layer, material include: above-mentioned dye monomer, resin
And photoinitiator;It additionally include solvent and additive.The production method of the optical diaphragm the following steps are included:
S301, above-mentioned dye monomer, resin, photoinitiator, solvent, additive are mixed, obtains optical film layer
Material, as shown in table 1:
The main constituent of material and content of table 1, optical film layer
Wherein resin mainly uses transparent acrylic resin comprising dimethylaminoethyl methacrylate, methyl-prop
One of olefin(e) acid butyl ester, hydroxyethyl methacrylate, cyclohexyl methacrylate and isooctyl methacrylate etc. are more
Kind.
Photoinitiator can be acetophenone derivs: α, α-diethoxy acetophenone, 2- methyl -2- morpholino -1- (4- first
Base thiophenyl) one of propane -1- ketone and HMPP or a variety of.
Solvent can be one in PGMEA (propylene glycol methyl ether acetate), PGME propylene glycol monomethyl ether and MEA ethanol amine
Kind or a variety of mixtures.
Additive can be the substances such as silane coupling agent.
S302, by optical film material through being coated on substrate, it is exposed and heat toast, obtain containing Luo Dan
The optical film layer of bright class dye monomer.
For example, as shown in Figure 1, above-mentioned optical film material is coated on substrate 21, later using the light shield of exposure
(Mask) it is exposed, above-mentioned optical film material is made to crosslink reaction, hot baking is carried out to it later, is obtained containing rhodamine
The optical film layer 22 of class dye monomer.Substrate 21 can be polaroid, protective layer (over coat, OC), organic planarization layer (material
One of material is perfluoroalkoxy resin, PFA) and color film color blocking.
Due to that can be sponged veiling glare (yellow orange light and dark green light) according to the selection of dye stuff of rhodamine kinds, to promote color
Domain, namely while improving the purity of primaries, improve penetrance.
Since dyestuff of the invention is to carry out singulation (Monomer) to rhodamine structure to obtain, after singulation
Dye stuff of rhodamine kinds stability it is stronger, to avoid the reunion of rhodamine molecule and cause the enhancing of acromion, reduce because of shoulder
It peak can be excessive to avoid the luminance loss of display while improving the purity of primaries to blue, green light absorption intensity
It reduces and absorbs energy that is blue, filtering, namely while improving the purity of primaries, improve brightness.
Further, since dyestuff of the invention is to carry out singulation (Monomer) to rhodamine structure to obtain, then
It is mixed with transparent resin and light initiator, and brings it about exposure cross-linking reaction, and then make rhodamine monomer polymerization, in this way
Rhodamine monomer can be made to form monodisperse structure, the reunion of rhodamine molecule is avoided and cause the enhancing of acromion, drop
It is low that blue, green light absorption intensity can be damaged while improving the purity of primaries to avoid the brightness of display because of acromion
It loses excessive.In addition, the thermal stability of dyestuff can be promoted using the polymerization of rhodamine monomer.
The preparation method and optical diaphragm of dyestuff of the invention, it is anti-in thionyl chloride by the way that dye stuff of rhodamine kinds to be added
It answers, obtains the first reaction solution, and the thionyl chloride in first reaction solution is removed, obtain the first reactant;By institute
State the first reactant, acrylic acid 4- hydroxyl R ester is added in anhydrous tetrahydro furan and reacts, obtain the second reaction solution, and by described the
Anhydrous tetrahydro furan removal in two reaction solutions, obtains the second reactant;Using methylene chloride and methanol to described second
Reactant is washed, and used chromatography post separation, obtains dye monomer.It is single due to carrying out singulation to dye stuff of rhodamine kinds
The stability of dye stuff of rhodamine kinds after body is stronger, to avoid that polymerization reaction occurs, reduces and absorbs energy that is blue, filtering,
While improving the purity of primaries, brightness is improved.
In conclusion although the present invention has been disclosed above in the preferred embodiment, but above preferred embodiment is not to limit
The system present invention, those skilled in the art can make various changes and profit without departing from the spirit and scope of the present invention
Decorations, therefore protection scope of the present invention subjects to the scope of the claims.
Claims (10)
1. a kind of preparation method of dyestuff characterized by comprising
Dye stuff of rhodamine kinds is added in thionyl chloride and is reacted, the first reaction solution is obtained;
By the thionyl chloride removal in first reaction solution, the first reactant is obtained;
First reactant, acrylic acid 4- hydroxyl R ester are added in anhydrous tetrahydro furan and reacted, the second reaction solution is obtained;
By the anhydrous tetrahydro furan removal in second reaction solution, the second reactant is obtained;
Second reactant is washed using methylene chloride and methanol, and used chromatography post separation, obtains dye monomer.
2. the preparation method of dyestuff according to claim 1, which is characterized in that the dye stuff of rhodamine kinds includes followingization
Learn structural formula:
At least one of;
Wherein X-Including but not limited to F-、Cl-、Br-、CF3SO3 -、CF2HSO3 -And CFH2SO3 -;Wherein R1~R5And R7~R11
Structure include linear paraffin, the alkane for having branch, the straight chain of alkoxy, the alkane of branch, chain object, F containing ester group
In alkane substitute derivative, the conjugated structure being connected by alkoxy and ester group and compound containing heterocycle at least
It is a kind of;The range of carbon chain lengths in the F alkane substitute derivatives group is 1~30;
R7It may also include but be not limited to-F ,-Cl ,-Br ,-I and-CN substituent group;
R8~R11It further include at least one of-F ,-Cl ,-Br and-I substituent group and including amino-NH2, carboxyl-
COOH, hydroxyl-OH, sulfate-SH, aldehyde root-COH, ester-COO-, acyl group-COCl ,-COBr, nitrile-CN, nitro-NO2, amino-
NH2At least one of ,=NH, ≡ N, benzene and phenol ring.
3. the preparation method of dyestuff according to claim 1, which is characterized in that the mole model of the dye stuff of rhodamine kinds
It encloses for 15mmol -30mmol.
4. the preparation method of dyestuff according to claim 1, which is characterized in that the range of capacity of the thionyl chloride is
20ml—60ml。
5. the preparation method of dyestuff according to claim 1, which is characterized in that mole of the acrylic acid 4- hydroxyl R ester
Amount range is 10mmol -40mmol.
6. the preparation method of dyestuff according to claim 1, which is characterized in that the range of capacity of the anhydrous tetrahydro furan
For 50ml -150ml.
7. the preparation method of dyestuff according to claim 1, which is characterized in that the body of the methylene chloride and the methanol
Product is than being 1:2.
8. the preparation method of dyestuff according to claim 1, which is characterized in that the dye stuff of rhodamine kinds and the dichloro
The temperature range of sulfoxide reaction is 80 DEG C -100 DEG C.
9. the preparation method of dyestuff according to claim 1, which is characterized in that
The chemical structural formula of the acrylic acid 4- hydroxyl R ester is as follows:
Wherein R6Structure include linear paraffin, the alkane for having branch, the straight chain of alkoxy, the alkane of branch, the chain containing ester group
In shape object, F alkane substitute derivative, the conjugated structure being connected by alkoxy and ester group and compound containing heterocycle
At least one;The range of carbon chain lengths in the F alkane substitute derivatives group is 1~30.
10. a kind of optical diaphragm characterized by comprising
Optical film layer, material include dye monomer, resin, photoinitiator;The dye monomer includes:
Wherein R6Structure include linear paraffin, the alkane for having branch, the straight chain of alkoxy, the alkane of branch, the chain containing ester group
In shape object, F alkane substitute derivative, the conjugated structure being connected by alkoxy and ester group and compound containing heterocycle
At least one;The range of carbon chain lengths in the F alkane substitute derivatives group is 1~30.
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CN201910405059.1A CN110194901A (en) | 2019-05-14 | 2019-05-14 | A kind of preparation method and optical diaphragm of dyestuff |
PCT/CN2019/104468 WO2020228191A1 (en) | 2019-05-14 | 2019-09-05 | Preparation method for dye and optical film |
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CN111077698A (en) * | 2019-12-17 | 2020-04-28 | Tcl华星光电技术有限公司 | Backlight module and liquid crystal display device |
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US10988619B2 (en) * | 2019-07-19 | 2021-04-27 | Tcl China Star Optoelectronics Technology Co., Ltd. | Manufacturing method of rhodamine dye oligomer, solid color material and liquid crystal display device |
WO2021093009A1 (en) * | 2019-11-13 | 2021-05-20 | Tcl华星光电技术有限公司 | Pure-color membrane and preparation method therefor, and display device |
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