CN110054741A - The preparation method of dispersible pigment dispersion - Google Patents
The preparation method of dispersible pigment dispersion Download PDFInfo
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- CN110054741A CN110054741A CN201910263447.0A CN201910263447A CN110054741A CN 110054741 A CN110054741 A CN 110054741A CN 201910263447 A CN201910263447 A CN 201910263447A CN 110054741 A CN110054741 A CN 110054741A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Abstract
The present invention provides a kind of preparation method of dispersible pigment dispersion, using the covalent organic framework material with network structure as template, pigment molecule is allowed to crystallize in the network structure of covalent organic framework as a solution, so as to control the granular size of crystalline pigment using the sizing grid of covalent organic framework network structure, after pigment sufficient crystallising, crystalline pigment is separated from covalent organic framework in such a way that salt is washed, add surfactant, it can be obtained by polymolecularity and the dispersible pigment dispersion of uniform particle sizes in this way, the dispersible pigment dispersion is post-treated to can be used for preparing colored photoresist, it is kind of the high performance pigments that can be realized display product high-penetration and high contrast, and covalent organic framework material can be used repeatedly.
Description
Technical field
The present invention relates to field of display technology more particularly to a kind of preparation methods of dispersible pigment dispersion.
Background technique
Thin-film transistor LCD device (Thin Film Transistor Liquid Crystal Display,
TFT-LCD) there are many merits such as thin fuselage, power saving, radiationless, be widely used.Liquid crystal on existing market
Showing device is largely backlight liquid crystal display device comprising liquid crystal display panel and backlight module (backlight
module).Usual liquid crystal display panel by color film (Color Filter, CF) substrate, tft array substrate, be sandwiched in color membrane substrates
Liquid crystal (Liquid Crystal, LC) and the sealing frame glue'' (Sealant) composition between tft array substrate；Its moulding process
Generally comprise: leading portion array (Array) processing procedure and CF processing procedure (film, yellow light, etching and stripping), middle section are at box (Cell) processing procedure
(tft array substrate is bonded with CF substrate) and back segment module group assembling (Module) processing procedure (driving IC and printed circuit board press)；
Wherein, leading portion Array processing procedure mainly forms TFT substrate, in order to control the movement of liquid crystal molecule；Leading portion CF processing procedure is mainly
Form CF substrate；Middle section Cell processing procedure mainly adds liquid crystal between TFT substrate and CF substrate；Back segment module group assembling processing procedure master
If driving the integration of IC pressing and printed circuit board, and then liquid crystal molecule rotation is driven, shows image.
CF substrate is the main devices that LCD is used to realize colored display, constitutes and generally includes substantially: glass substrate, black
Colour moment battle array (Black Matrix, BM), chromatic filter layer etc..Wherein, chromatic filter layer is mainly reached by chromatic photoresist
The effect of colour display, the light that backlight issues are incident on CF substrate by the modulation of liquid crystal molecule, are enameled by CF substrate
The filter action of red (R) photoresist, green (G) photoresist and blue (B) photoresist of filter layer, shows red, green, blue three respectively
Kind light, the light of the photoresist difference TEM investigation color bands of different colours, to realize the colored display of display.
Currently, the production method of chromatic filter layer is colored based on pigment (Pigment) dispersion method in TFT-LCD technology
Filter layer is mainly scattered among resin by phthalocyanine, azo, Anthraquinones pigment, is formed by processing procedures such as coating, exposure, developments
R/G/B photoresist pattern.The usual dissolubility of these pigment in organic solvent is all poor, such as chromatic filter layer is common
PGMEA (propylene glycol monomethyl ether acid esters) solvent, so that bad dispersibility, and there is scattering in the pigment of particle habit, to LCD's
Brightness and contrast has a certain impact, so, pigment colour blocking material (Dye) is changed at present, it in this way can be with effective solution
Dissolubility and dispersion problem, conducive to the brightness and contrast for promoting LCD.But the thermal stability of dyestuff is poor, it is difficult to meet
Hot processing procedure (generally up to temperature is 230 DEG C) among the manufacturing process of LCD, many dyestuffs are sent out in hot processing procedure because of stability difference
Heat cracking in this way influences the coloration of chromatic filter layer very big.
With the development of LCD technology, the requirement to performances such as high colour gamut, high-penetration, high comparisons is also higher and higher,
And chromatic filter layer is suffered from colour gamut, penetrance and contrast and is directly contacted, then to face in color film photoresist in industry
The requirement of material is naturally also higher and higher, and the high thermal stability of pigment can satisfy the preparation process temperatures of liquid crystal display, pigment
Particle size and partial size distribution become improve product quality crucial control coefficient.
At present prepare pigment method be all to be obtained by way of " from top to bottom ", i.e., by the method for physics come
Realize the pigment from bulky grain grinding distribution to nanoscale, the particle size dispersion that this method prepares is uneven, and is difficult to
It obtains small size (≤50nm).Therefore, now with LCD technology color domain, penetrate and wanted with the height of contrast etc.
It asks, as the development of pigment in color film photoresist, and restricts the key factor of high-performance liquid crystal display technology development.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation methods of dispersible pigment dispersion, and it is equal to prepare partial size using template
Even, scale is controllable, polymolecularity dispersible pigment dispersion, which is used as when preparing colored photoresist, can meet high color
The liquid crystal display growth requirement in domain, high-penetration and high comparison.
To achieve the above object, the present invention provides a kind of preparation method of dispersible pigment dispersion, include the following steps:
Step S1, covalent organic framework material is prepared, the covalent organic framework material has network structure；
Step S2, pigment is provided, pigment is prepared into pigment solution, covalent organic framework material is placed in pigment solution
In, i.e., using covalent organic framework material as template, allow pigment molecule as a solution in the network knot of covalent organic framework
It is crystallized in structure, forms crystalline pigment；
Step S3, crystalline pigment is separated from the network structure of covalent organic framework in such a way that salt is washed, is added
Enter surfactant, obtains dispersible pigment dispersion.
The method that covalent organic framework material is prepared in the step S1 is, by four (4- Fonnylphenyl) methane class chemical combination
Schiff base reaction occurs under the action of catalyst for object and phenylene diamine compound, obtains covalent organic framework material.
Four (4- Fonnylphenyl) methane compound is four (4- Fonnylphenyl) methane or four (4- formoxyl benzene
Base) methane Derivatives, the phenylene diamine compound is p-phenylenediamine or phenylenediamine derivative；
Wherein, the general structure of described four (4- Fonnylphenyl) methane Derivatives is
Wherein, n is the quantity that internal carbon atoms connect alkane,
N is 1-30；
The general structure of the phenylenediamine derivative isWherein, m is
The number of repeat unit of intermediate phenyl ring, m 1-15.
Catalyst used in the step S1 is bis- ((trifluoromethyl) sulfonyl) acid imides.
The pigment provided in the step S2 is red pigment, viridine green, yellow uitramarine or blue pigment.
The pigment provided in the step S2 is paratonere 254, paratonere 177, pigment Green 7, pigment green 36, naphthol green
58, one of pigment yellow 13 8, pigment yellow 150, pigment yellow 185 and pigment blue B15:1-6 or a variety of.
The network structure of prepared covalent organic framework material has a grid in the step S1, the grid it is equivalent straight
Diameter is 20-60nm.
It is sodium chloride that used salt lotion when salt is washed is carried out in the step S3.
The dispersible pigment dispersion is used to prepare colored photoresist.
The colour photoresist is used to prepare the chromatic photoresist on color membrane substrates.
Beneficial effects of the present invention: the preparation method of dispersible pigment dispersion of the invention, with covalently having with network structure
Machine framework material allows pigment molecule to crystallize in the network structure of covalent organic framework as a solution as template, thus
The sizing grid of covalent organic framework network structure be can use to control the granular size of crystalline pigment, to pigment sufficient crystallising
Later, crystalline pigment is separated in such a way that salt is washed from covalent organic framework, adds surfactant, thus may be used
To obtain the dispersible pigment dispersion of polymolecularity and uniform particle sizes, the dispersible pigment dispersion is post-treated to can be used for preparing colored photoetching
Glue, to can be realized the high performance pigments for showing product high-penetration and high contrast, and covalent organic framework material can be multiple
Recycling.
For further understanding of the features and technical contents of the present invention, it please refers to below in connection with of the invention detailed
Illustrate and attached drawing, however, the drawings only provide reference and explanation, is not intended to limit the present invention.
Detailed description of the invention
With reference to the accompanying drawing, by the way that detailed description of specific embodiments of the present invention, technical solution of the present invention will be made
And other beneficial effects are apparent.
In attached drawing,
Fig. 1 is the flow diagram of the preparation method of dispersible pigment dispersion of the present invention；
Fig. 2 is covalent organic framework material three-dimensional schematic network structure.
Specific embodiment
Further to illustrate technological means and its effect adopted by the present invention, below in conjunction with preferred implementation of the invention
Example is described in detail.
Referring to Fig. 1, the present invention provides a kind of preparation method of dispersible pigment dispersion, which is used to prepare colour
Photoresist, and then be used to prepare the chromatic photoresist on color membrane substrates is that by display product high-penetration and high contrast
High performance pigments.
Embodiment one utilizes the network of covalent organic framework material (Covalent Organic Frameworks, COF)
The dispersible pigment dispersion of structure preparation red pigment
The present embodiment one includes the following steps:
Step S1, covalent organic framework material is prepared, the covalent organic framework material has network structure, preparing
Cheng Zhong, organic construction unit are linked together by covalent bond, form the stephanoporate framework with periodic structure.
Specifically, covalent organic framework material can generate in the following way: by four (4- Fonnylphenyl) methane classes
Schiff base reaction occurs under the action of catalyst for compound and phenylene diamine compound, obtains covalent organic framework material.Wherein,
Four (4- Fonnylphenyl) methane compound is four (4- Fonnylphenyl) methane or four (4- Fonnylphenyl) methane
Derivative, the phenylene diamine compound are p-phenylenediamine or phenylenediamine derivative.
By taking four (4- Fonnylphenyl) methane and p-phenylenediamine as an example, by four (4- Fonnylphenyl) methane and p-phenylenediamine
Under the action of catalyst, schiff base reaction can occur for room temperature, generate the covalent organic framework material with network structure,
Chemical equation is as follows:
In addition, during preparing covalent organic framework material, it can be according to four (4- Fonnylphenyl) methane classes
The structure for closing object and phenylene diamine compound modifies to the structure of COF, as shown in Fig. 2, can regulate and control COF network knot in turn
Sizing grid in structure, will be within the scope of the equivalent diameter control 20-60nm of grid in its network structure.
Wherein, the general structure of described four (4- Fonnylphenyl) methane Derivatives is
Wherein the quantity n of internal carbon atoms connection alkane can be with
For 1-30, the length which connects alkane is 6-36nm.
The general structure of the phenylenediamine derivative isThus can also
Regulate and control to form the bulk of network structure with the length by the repetitive unit of in-between phenyl ring, wherein the weight of intermediate phenyl ring
Multiple unit number m can be 1-15, and the length range of the repetitive unit of the intermediate phenyl ring is in 5-75nm.
Under the action of catalyst by four (4- Fonnylphenyl) methane Derivatives and phenylenediamine derivative, it is anti-that schiff bases occurs
Shown under the COF general structure that should be generated,
Specifically, catalyst used in the step S1 is bis- ((trifluoromethyl) sulfonyl) acid imides.
Step S2, using the network structure of above-mentioned COF as template, red pigment is prepared into pigment solution, wherein
With two kinds of red pigments common in colored photoresist, for paratonere 254 and paratonere 177, by covalent organic framework material
It is placed in pigment solution, the static nanocrystalline structure that can form red pigment for 120 minutes, i.e., with covalent organic framework material
Material is used as template, and pigment molecule is allowed to crystallize in the network structure of covalent organic framework as a solution, forms crystalline pigment.
Wherein, the molecular structural formula of paratonere 254 and paratonere 177 is respectively
Step S3, crystalline pigment is separated from the network structure of covalent organic framework in such a way that salt is washed, i.e.,
Crystalline pigment from the network structure of covalent organic framework is washed away out using salting liquid such as sodium chloride solution, is then added
Surfactant is uniformly dispersed, the dispersible pigment dispersion of the red pigment of uniform particle sizes.
Embodiment two, the dispersible pigment dispersion that viridine green is prepared using the network structure of COF
Using the network structure of the COF in embodiment one as template, viridine green is prepared into pigment solution, wherein with
Three kinds of common viridine greens in colored photoresist, for pigment Green 7, pigment green 36, naphthol green 58, by covalent organic framework material
Material is placed in pigment solution, and the static nanocrystalline structure that can form viridine green for 120 minutes, size can pass through
The size of grid controls in COF network structure, then in such a way that salt is washed by the crystalline pigment of viridine green from the network of COF
Separated in structure, then add surfactant, so that it may obtain high dispersive, uniform particle sizes viridine green pigment point
Dispersion liquid.Wherein, pigment Green 7, pigment green 36, naphthol green 58 molecular structural formula be respectively
Embodiment three, the dispersible pigment dispersion that yellow uitramarine is prepared using the network structure of COF
Using the network structure of the COF in embodiment one as template, yellow uitramarine is prepared into pigment solution, wherein with
Three kinds of common yellow uitramarines in colored photoresist will covalent organic bone for pigment yellow 13 8, pigment yellow 150, pigment yellow 185
Frame material is placed in pigment solution, and the static nanocrystalline structure that can form yellow uitramarine for 120 minutes, size can lead to
The size of grid in COF network structure is crossed to control, then in such a way that salt is washed by the crystalline pigment of yellow uitramarine from COF's
Separated in network structure, add surfactant, so that it may obtain high dispersive, uniform particle sizes yellow uitramarine pigment point
Dispersion liquid.Wherein, pigment yellow 13 8, pigment yellow 150, pigment yellow 185 molecular structural formula be respectively
Example IV, the dispersible pigment dispersion that blue pigment is prepared using the network structure of COF
Using the network structure of the COF in embodiment one as template, blue pigment is prepared into pigment solution, wherein with
For pigment blue B15:1-6, it is molten to be placed in pigment by common a kind of blue pigment in colored photoresist for covalent organic framework material
In liquid, the static nanocrystalline structure that can form blue pigment for 120 minutes, size can be by COF network structure
The size of grid controls, and then separates the crystalline pigment of blue pigment from the network structure of COF in such a way that salt is washed
Out, add surfactant, so that it may obtain high dispersive, uniform particle sizes blue pigment dispersible pigment dispersion.Wherein, pigment
The molecular structural formula of blue B15:1-6 is
The preparation method of dispersible pigment dispersion of the invention, using the covalent organic framework material with network structure as mould
Plate allows pigment molecule to crystallize in the network structure of covalent organic framework as a solution, covalently organic so as to utilize
Then the sizing grid of back bone network structure passes through salt after pigment sufficient crystallising to control the granular size of crystalline pigment
The mode washed separates crystalline pigment from covalent organic framework, adds surfactant, can be obtained by high score in this way
Property and the dispersible pigment dispersion of uniform particle sizes are dissipated, the dispersible pigment dispersion is post-treated to can be used for preparing colored photoresist, and being can
Realize the high performance pigments of display product high-penetration and high contrast, and covalent organic framework material can be used repeatedly.
In conclusion the preparation method of dispersible pigment dispersion of the invention, with the covalent organic framework material with network structure
Material is used as template, allows pigment molecule to crystallize in the network structure of covalent organic framework as a solution, so as to utilize
The sizing grid of covalent organic framework network structure leads to after pigment sufficient crystallising to control the granular size of crystalline pigment
The mode that supersalt is washed separates crystalline pigment from covalent organic framework, adds surfactant, can be obtained by this way
Polymolecularity and the dispersible pigment dispersion of uniform particle sizes, the dispersible pigment dispersion is post-treated to can be used for preparing colored photoresist, is
It can be realized the high performance pigments of display product high-penetration and high contrast, and benefit can be repeated several times in covalent organic framework material
With.
The above for those of ordinary skill in the art can according to the technique and scheme of the present invention and technology
Other various corresponding changes and modifications are made in design, and all these change and modification all should belong to the claims in the present invention
Protection scope.
Claims (10)
1. a kind of preparation method of dispersible pigment dispersion, which comprises the steps of:
Step S1, covalent organic framework material is prepared, the covalent organic framework material has network structure；
Step S2, pigment is provided, pigment is prepared into pigment solution, covalent organic framework material is placed in pigment solution, i.e.,
Using covalent organic framework material as template, pigment molecule is allowed to tie in the network structure of covalent organic framework as a solution
Crystalline substance forms crystalline pigment；
Step S3, crystalline pigment is separated from the network structure of covalent organic framework in such a way that salt is washed, table is added
Face activating agent, obtains dispersible pigment dispersion.
2. the preparation method of dispersible pigment dispersion as described in claim 1, which is characterized in that covalently there is preparation in the step S1
The method of machine framework material is, by four (4- Fonnylphenyl) methane compounds and phenylene diamine compound in catalyst action
Lower generation schiff base reaction, obtains covalent organic framework material.
3. the preparation method of dispersible pigment dispersion as claimed in claim 2, which is characterized in that described four (4- Fonnylphenyl) first
Alkyl compound is four (4- Fonnylphenyl) methane or four (4- Fonnylphenyl) methane Derivatives, the phenylenediamine chemical combination
Object is p-phenylenediamine or phenylenediamine derivative；
The general structure of described four (4- Fonnylphenyl) methane Derivatives is
Wherein, n is the quantity that internal carbon atoms connect alkane, and n is
1-30；
The general structure of the phenylenediamine derivative isWherein, m is middle isophthalic
The number of repeat unit of ring, m 1-15.
4. the preparation method of dispersible pigment dispersion as claimed in claim 2, which is characterized in that urged used in the step S1
Agent is bis- ((trifluoromethyl) sulfonyl) acid imides.
5. the preparation method of dispersible pigment dispersion as described in claim 1, which is characterized in that the pigment provided in the step S2
For red pigment, viridine green, yellow uitramarine or blue pigment.
6. the preparation method of dispersible pigment dispersion as claimed in claim 5, which is characterized in that the pigment provided in the step S2
For paratonere 254, paratonere 177, pigment Green 7, pigment green 36, naphthol green 58, pigment yellow 13 8, pigment yellow 150, pigment yellow 185
And one of pigment blue B15:1-6 or a variety of.
7. the preparation method of dispersible pigment dispersion as described in claim 1, which is characterized in that prepared in the step S1 to be total to
The network structure of valence organic framework material has grid, and the equivalent diameter of the grid is 20-60nm.
8. the preparation method of dispersible pigment dispersion as described in claim 1, which is characterized in that when progress salt is washed in the step S3
Used salt lotion is sodium chloride.
9. the preparation method of dispersible pigment dispersion as described in claim 1, which is characterized in that the dispersible pigment dispersion is used to prepare
Colored photoresist.
10. the preparation method of dispersible pigment dispersion as claimed in claim 9, which is characterized in that the colour photoresist is for making
Chromatic photoresist on standby color membrane substrates.
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| CN201910263447.0A CN110054741B (en) | 2019-04-02 | 2019-04-02 | Method for preparing pigment dispersion liquid |
| PCT/CN2019/101896 WO2020199463A1 (en) | 2019-04-02 | 2019-08-22 | Method for preparing pigment dispersion |
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| WO2020199463A1 (en) * | 2019-04-02 | 2020-10-08 | 深圳市华星光电技术有限公司 | Method for preparing pigment dispersion |
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| CN111367144A (en) * | 2020-04-08 | 2020-07-03 | Tcl华星光电技术有限公司 | Pigment particle template, method for producing same, and method for producing pigment dispersion liquid |
| WO2021203464A1 (en) * | 2020-04-08 | 2021-10-14 | Tcl华星光电技术有限公司 | Pigment particle template, manufacturing method therefor and preparation method for pigment dispersion liquid |
| US11453782B2 (en) | 2020-04-08 | 2022-09-27 | TCL China Star Optoelectronies Technology Co., Ltd. | Pigment particle template and method of fabricating same, and method of fabricating pigment dispersion liquid |
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| CN110054741B (en) | 2020-10-30 |
| WO2020199463A1 (en) | 2020-10-08 |
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