CN110054741B - Method for preparing pigment dispersion liquid - Google Patents
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- CN110054741B CN110054741B CN201910263447.0A CN201910263447A CN110054741B CN 110054741 B CN110054741 B CN 110054741B CN 201910263447 A CN201910263447 A CN 201910263447A CN 110054741 B CN110054741 B CN 110054741B
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- 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
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- 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 invention provides a preparation method of a pigment dispersion liquid, which takes a covalent organic framework material with a network structure as a template, leads pigment molecules to be crystallized in the network structure of the covalent organic framework in a solution form, thereby controlling the particle size of pigment crystals by utilizing the network size of the network structure of the covalent organic framework, separates the pigment crystals from the covalent organic framework in a salt washing way after the pigment is fully crystallized, adds a surfactant, thus obtaining the pigment dispersion liquid with high dispersibility and uniform particle size, can be used for preparing a color photoresist after being post-treated, is a high-performance pigment capable of realizing high penetration and high contrast of a display product, and can repeatedly utilize the covalent organic framework material for multiple times.
Description
Technical Field
The invention relates to the technical field of display, in particular to a preparation method of a pigment dispersion liquid.
Background
A Thin Film Transistor Liquid Crystal Display (TFT-LCD) has many advantages such as a Thin body, power saving, and no radiation, and is widely used. Most of the existing liquid crystal display devices in the market are backlight liquid crystal display devices, which include a liquid crystal display panel and a backlight module (backlight module). Generally, a Liquid Crystal display panel is composed of a Color Filter (CF) substrate, a TFT array substrate, a Liquid Crystal (LC) and a Sealant (Sealant) sandwiched between the Color Filter substrate and the TFT array substrate; the molding process generally comprises: front Array (Array) process, CF process (film, yellow light, etching and stripping), middle Cell (TFT Array substrate and CF substrate bonding), and back Module assembly (Module) process (driving IC and printed circuit board bonding); wherein, the front-stage Array process mainly forms a TFT substrate to control the movement of liquid crystal molecules; the front CF process mainly forms a CF substrate; the middle Cell process is mainly to add liquid crystal between the TFT substrate and the CF substrate; the back module assembly process mainly drives the integration of IC pressing and printed circuit board, and further drives the liquid crystal molecules to rotate and display images.
The CF substrate is a main device used by the LCD to realize color display, and its basic constitution generally includes: a glass substrate, a Black Matrix (BM), a color filter layer, etc. The color filter layer achieves a color display effect mainly through the color photoresist, light emitted by the backlight source is modulated by liquid crystal molecules and enters the CF substrate, red (R) photoresist, green (G) photoresist and blue (B) photoresist of the color filter layer on the CF substrate are used for filtering, red, green and blue light rays are respectively displayed, and the photoresists of different colors respectively transmit light of corresponding color wave bands, so that the color display of the display is realized.
At present, the manufacturing method of the color filter layer in the TFT-LCD technology mainly uses a Pigment (Pigment) dispersion method, and the color filter layer is mainly formed by dispersing phthalocyanine, azo, anthraquinone pigments in resin, and forming R/G/B photoresist patterns through processes of coating, exposure, development, etc. Generally, the solubility of these pigments in organic solvents is poor, for example, PGMEA (propylene glycol monomethyl ether acetate) solvents commonly used for color filter layers are poor in dispersibility, and the pigments with particle properties are scattered and have certain influence on the brightness and contrast of LCDs, so that the pigment color-resistant dyes (Dye) are converted at present, so that the problems of solubility and dispersibility can be effectively solved, and the brightness and contrast of LCDs can be improved. However, the thermal stability of the dye is poor, and it is difficult to satisfy the thermal process (usually, the maximum temperature is 230 ℃) in the process of LCD, and many dyes are thermally cracked due to the poor stability in the thermal process, thus greatly affecting the chromaticity of the color filter layer.
With the development of liquid crystal display technology, the requirements for high color gamut, high penetration, high contrast and other properties are higher and higher, and the color filter layer is directly connected with the color gamut, the penetration rate and the contrast, so the requirements for the pigment in the color film photoresist in the industry are naturally higher and higher, the high thermal stability of the pigment can meet the temperature of the preparation process of the liquid crystal display, and the particle size and the distribution of the particle size of the pigment become the key card control coefficients for improving the product quality.
The current method for preparing the pigment is obtained in a mode of top-down, namely, the pigment with large particles dispersed to a nanometer scale is realized by a physical method, the particle size prepared by the method is not uniformly dispersed, and the small size (less than or equal to 50nm) is difficult to obtain. Therefore, with the high requirements of the liquid crystal display technology on color gamut, penetration, contrast and the like, the development of the pigment in the color film photoresist is also a key factor for restricting the development of the high-performance liquid crystal display technology.
Disclosure of Invention
The invention aims to provide a preparation method of a pigment dispersion liquid, which utilizes a template method to prepare the pigment dispersion liquid with uniform particle size, controllable scale and high dispersibility, and can meet the development requirements of liquid crystal displays with high color gamut, high penetration and high contrast when the pigment dispersion liquid is used for preparing color photoresists.
In order to achieve the above object, the present invention provides a method for preparing a pigment dispersion, comprising the steps of:
step S1, preparing a covalent organic framework material, wherein the covalent organic framework material has a network structure;
step S2, providing a pigment, preparing the pigment into a pigment solution, placing the covalent organic framework material into the pigment solution, namely, taking the covalent organic framework material as a template, and crystallizing pigment molecules in a network structure of the covalent organic framework in a solution form to form a pigment crystal;
and step S3, separating the pigment crystals from the network structure of the covalent organic framework in a salt washing mode, and adding a surfactant to obtain a pigment dispersion liquid.
The method for preparing the covalent organic framework material in the step S1 is to perform schiff base reaction on the tetra (4-formylphenyl) methane compound and the phenylenediamine compound under the action of the catalyst to obtain the covalent organic framework material.
The tetra (4-formylphenyl) methane compound is tetra (4-formylphenyl) methane or a tetra (4-formylphenyl) methane derivative, and the phenylenediamine compound is p-phenylenediamine or a phenylenediamine derivative;
wherein the structural general formula of the tetra (4-formylphenyl) methane derivative is
the structural general formula of the phenylenediamine derivative is shown in the specification
Wherein m is the number of repeating units of the middle benzene ring, and m is 1-15.
The catalyst used in step S1 is bis ((trifluoromethyl) sulfonyl) imide.
The pigment provided in step S2 is a red pigment, a green pigment, a yellow pigment, or a blue pigment.
The pigment provided in step S2 is one or more of pigment red 254, pigment red 177, pigment green 7, pigment green 36, pigment green 58, pigment yellow 138, pigment yellow 150, pigment yellow 185, and pigment blue B15: 1-6.
The network structure of the covalent organic framework material prepared in the step S1 has a lattice, and the equivalent diameter of the lattice is 20 to 60 nm.
The salt washing agent used in the salt washing in step S3 is sodium chloride.
The pigment dispersion is used for preparing a color photoresist.
The color photoresist is used for preparing a color photoresist on a color film substrate.
The invention has the beneficial effects that: the preparation method of the pigment dispersion liquid uses a covalent organic framework material with a network structure as a template, leads pigment molecules to crystallize in the network structure of the covalent organic framework in a solution form, thereby controlling the particle size of pigment crystals by utilizing the mesh size of the network structure of the covalent organic framework, separates the pigment crystals from the covalent organic framework in a salt washing way after the pigment is fully crystallized, adds a surfactant, thus obtaining the pigment dispersion liquid with high dispersibility and uniform particle size, can be used for preparing color photoresist after post treatment, and can realize high-performance pigment with high penetration and high contrast of a display product, and the covalent organic framework material can be repeatedly utilized for a plurality of times.
For a better understanding of the nature and technical aspects of the present invention, reference should be made to the following detailed description of the invention, taken in conjunction with the accompanying drawings, which are provided for purposes of illustration and description and are not intended to limit the invention.
Drawings
The technical solution and other advantages of the present invention will become apparent from the following detailed description of specific embodiments of the present invention, which is to be read in connection with the accompanying drawings.
In the drawings, there is shown in the drawings,
FIG. 1 is a schematic flow diagram of a process for preparing a pigment dispersion according to the present invention;
FIG. 2 is a schematic diagram of a three-dimensional network structure of a covalent organic framework material.
Detailed Description
To further illustrate the technical means adopted by the present invention and the effects thereof, the following detailed description is given with reference to the preferred embodiments of the present invention.
Referring to fig. 1, the present invention provides a method for preparing a pigment dispersion, which is a high-performance pigment capable of realizing high penetration and high contrast of a display product, and is used for preparing a color photoresist and further preparing a color photoresist on a color film substrate.
EXAMPLE one pigment dispersion of a Red pigment was prepared using a network structure of a Covalent Organic Framework (COF)
The first embodiment includes the following steps:
and S1, preparing a covalent organic framework material, wherein the covalent organic framework material has a network structure, and in the preparation process, organic construction units are connected together through covalent bonds to form a porous framework with a periodic structure.
Specifically, the covalent organic framework material may be generated by: the tetra (4-formylphenyl) methane compound and the phenylenediamine compound are subjected to Schiff base reaction under the action of a catalyst to obtain the covalent organic framework material. Wherein the tetra (4-formylphenyl) methane compound is tetra (4-formylphenyl) methane or a tetra (4-formylphenyl) methane derivative, and the phenylenediamine compound is p-phenylenediamine or a phenylenediamine derivative.
Taking tetrakis (4-formylphenyl) methane and p-phenylenediamine as an example, under the action of a catalyst, the tetrakis (4-formylphenyl) methane and the p-phenylenediamine can generate Schiff base reaction at normal temperature to generate a covalent organic framework material with a network structure, and the chemical reaction formula is shown as follows:
in addition, in the process of preparing the covalent organic framework material, the structure of the COF can be modified according to the structures of the tetra (4-formylphenyl) methane compound and the phenylenediamine compound, as shown in figure 2, so that the size of a grid in a COF network structure can be regulated and controlled, and the equivalent diameter of the grid in the COF network structure is controlled within the range of 20-60 nm.
Wherein the structural general formula of the tetra (4-formylphenyl) methane derivative is
The structural general formula of the phenylenediamine derivative is shown in the specification
Thereby the space size of the network structure can be adjusted and controlled by the length of the repeating unit of the middle benzene ring, wherein the number m of the repeating unit of the middle benzene ring can be 1-15, and the length of the repeating unit of the middle benzene ring ranges from 5-75 nm.
The COF is shown in a structural general formula of a COF generated by Schiff base reaction of a tetra (4-formylphenyl) methane derivative and a phenylenediamine derivative under the action of a catalyst,
specifically, the catalyst used in step S1 is bis ((trifluoromethyl) sulfonyl) imide.
Step S2, using the above COF network structure as a template, preparing a pigment solution from a red pigment, wherein two red pigments, pigment red 254 and pigment red 177, which are commonly found in color photoresists, are used as an example, a covalent organic framework material is placed in the pigment solution, and a nanocrystal structure of the red pigment can be formed after standing for 120 minutes, that is, the covalent organic framework material is used as a template, so that pigment molecules are crystallized in the covalent organic framework network structure in a solution form to form pigment crystals. Wherein the molecular structural formulas of the pigment red 254 and the pigment red 177 are respectively
And step S3, separating the pigment crystals from the network structure of the covalent organic framework in a salt washing mode, namely washing the pigment crystals from the network structure of the covalent organic framework by using a salt solution such as a sodium chloride solution, and then adding a surfactant to obtain the pigment dispersion liquid of the red pigment with uniform dispersion and uniform particle size.
Example two preparation of pigment Dispersion of Green pigment Using network Structure of COF
Taking three green pigments, namely pigment green 7, pigment green 36 and pigment green 58, which are commonly seen in color photoresists as an example, a covalent organic framework material is placed in the pigment solution, standing for 120 minutes can form a nanocrystal structure of the green pigment, the size of the nanocrystal structure can be controlled by the size of a grid in a COF network structure, the pigment crystals of the green pigment are separated from the COF network structure in a salt washing mode, and then a surfactant is added, so that the pigment dispersion liquid of the green pigment with high dispersion and uniform particle size can be obtained. Wherein the molecular structural formulas of the pigment green 7, the pigment green 36 and the pigment green 58 are respectively
EXAMPLE III preparation of pigment Dispersion of yellow pigment Using network Structure of COF
Taking the network structure of the COF in the first embodiment as a template, preparing a yellow pigment into a pigment solution, wherein three common yellow pigments in a color photoresist, namely pigment yellow 138, pigment yellow 150 and pigment yellow 185 are taken as examples, a covalent organic framework material is placed in the pigment solution, standing for 120 minutes can form a nanocrystal structure of the yellow pigment, the size of the nanocrystal structure can be controlled by the size of a grid in the COF network structure, then the pigment crystals of the yellow pigment are separated from the network structure of the COF in a salt washing mode, and a surfactant is added to obtain a pigment dispersion liquid of the yellow pigment with high dispersion and uniform particle size. Wherein the molecular structural formulas of the pigment yellow 138, the pigment yellow 150 and the pigment yellow 185 are respectively
Example four preparation of pigment Dispersion of blue pigment Using network Structure of COF
The network structure of the COF in the first embodiment is used as a template, a blue pigment is prepared into a pigment solution, wherein a blue pigment which is commonly used in a color photoresist is taken as an example, pigment blue B15:1-6, a covalent organic framework material is placed in the pigment solution, a nanocrystal structure of the blue pigment can be formed after standing for 120 minutes, the size of the nanocrystal structure can be controlled by the size of a grid in the COF network structure, then the pigment crystals of the blue pigment are separated from the network structure of the COF in a salt washing mode, and a surfactant is added to obtain a pigment dispersion liquid of the blue pigment with high dispersion and uniform particle size. Wherein the molecular structural formula of the pigment blue B15:1-6 is
The preparation method of the pigment dispersion liquid uses a covalent organic framework material with a network structure as a template, leads pigment molecules to crystallize in the network structure of the covalent organic framework in a solution form, thereby controlling the particle size of pigment crystals by utilizing the mesh size of the network structure of the covalent organic framework, separates the pigment crystals from the covalent organic framework in a salt washing way after the pigment is fully crystallized, adds a surfactant, thus obtaining the pigment dispersion liquid with high dispersibility and uniform particle size, can be used for preparing color photoresist after post treatment, and can realize high-performance pigment with high penetration and high contrast of a display product, and the covalent organic framework material can be repeatedly utilized for a plurality of times.
In summary, the preparation method of the pigment dispersion liquid of the present invention uses the covalent organic framework material with a network structure as a template, and allows the pigment molecules to crystallize in the network structure of the covalent organic framework in the form of solution, so that the size of the network of the covalent organic framework structure can be used to control the particle size of the pigment crystal, after the pigment is sufficiently crystallized, the pigment crystal is separated from the covalent organic framework in a salt washing manner, and a surfactant is added, so that the pigment dispersion liquid with high dispersibility and uniform particle size can be obtained, and the pigment dispersion liquid can be used for preparing a color photoresist after post-treatment, so as to realize high-performance pigment with high penetration and high contrast of the display product, and the covalent organic framework material can be repeatedly used for many times.
As described above, it will be apparent to those skilled in the art that other various changes and modifications may be made based on the technical solution and concept of the present invention, and all such changes and modifications are intended to fall within the scope of the appended claims.
Claims (9)
1. A method for preparing a pigment dispersion, comprising the steps of:
step S1, preparing a covalent organic framework material, wherein the covalent organic framework material has a network structure;
step S2, providing a pigment, preparing the pigment into a pigment solution, placing the covalent organic framework material into the pigment solution, and standing to form a nano-crystal structure of the pigment; the covalent organic framework material is used as a template, and pigment molecules are crystallized in a network structure of the covalent organic framework in a solution form to form pigment crystals;
step S3, separating the pigment crystals from the network structure of the covalent organic framework in a salt washing mode, namely washing the pigment crystals from the network structure of the covalent organic framework by using a salt solution, and adding a surfactant to obtain a pigment dispersion liquid;
the method for preparing the covalent organic framework material in the step S1 is to perform schiff base reaction on the tetra (4-formylphenyl) methane compound and the phenylenediamine compound under the action of the catalyst to obtain the covalent organic framework material.
2. The method for producing a pigment dispersion according to claim 1, wherein the tetrakis (4-formylphenyl) methane compound is tetrakis (4-formylphenyl) methane or a tetrakis (4-formylphenyl) methane derivative, and the phenylenediamine compound is p-phenylenediamine or a phenylenediamine derivative;
the structural general formula of the tetra (4-formylphenyl) methane derivative is
Wherein n is the number of the intermediate carbon atoms connected with the alkane, and n is 1-30;
the structural general formula of the phenylenediamine derivative is shown in the specification
Wherein m is the number of repeating units of the middle benzene ring, and m is 1-15.
3. The method of preparing a pigment dispersion according to claim 1, wherein the catalyst used in step S1 is bis ((trifluoromethyl) sulfonyl) imide.
4. The method of preparing a pigment dispersion according to claim 1, wherein the pigment provided in step S2 is a red pigment, a green pigment, a yellow pigment, or a blue pigment.
5. The method of preparing a pigment dispersion according to claim 4, wherein the pigment provided in step S2 is one or more of pigment Red 254, pigment Red 177, pigment Green 7, pigment Green 36, pigment Green 58, pigment yellow 138, pigment yellow 150, pigment yellow 185, and pigment blue B15: 1-6.
6. The method of preparing a pigment dispersion according to claim 1, wherein the network structure of the covalent organic framework material prepared in step S1 has a lattice with an equivalent diameter of 20 to 60 nm.
7. The method of producing a pigment dispersion according to claim 1, wherein the salt washing agent used in the salt washing in step S3 is sodium chloride.
8. A pigment dispersion liquid for use in the production of a color resist, wherein the pigment dispersion liquid is produced by the method for producing a pigment dispersion liquid according to claim 1.
9. The pigment dispersion according to claim 8, wherein the color photoresist is used for preparing a color photoresist on a color film substrate.
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| CN201910263447.0A CN110054741B (en) | 2019-04-02 | 2019-04-02 | Method for preparing pigment dispersion liquid |
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| CN110054741B (en) * | 2019-04-02 | 2020-10-30 | 深圳市华星光电技术有限公司 | Method for preparing pigment dispersion liquid |
| CN110511357B (en) * | 2019-08-09 | 2022-03-15 | 山东省分析测试中心 | Solid-phase microextraction adsorbent for carbamate pesticide detection and preparation method and application thereof |
| CN110927851A (en) * | 2019-11-13 | 2020-03-27 | Tcl华星光电技术有限公司 | Pure-color membrane, preparation method thereof and display device |
| CN111367144B (en) * | 2020-04-08 | 2021-06-01 | 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 |
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| US6447594B1 (en) * | 2001-06-13 | 2002-09-10 | Wayne Pigment Corporation | Strontium chromate corrosion inhibitor pigment with reduced solubility |
| JP4401047B2 (en) * | 2001-09-26 | 2010-01-20 | 富士フイルム株式会社 | Azomethine yellow dye compound |
| CN1281302C (en) * | 2003-05-28 | 2006-10-25 | 财团法人工业技术研究院 | Submicron-sized dispersed liquid preparing method |
| JP2005008727A (en) * | 2003-06-18 | 2005-01-13 | Toshiba Tec Corp | Processed pigment, pigment dispersion, ink-jet ink, method for producing the processed pigment, and method for producing the pigment dispersion |
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| WO2011108496A1 (en) * | 2010-03-03 | 2011-09-09 | 大日本印刷株式会社 | Pigment dispersion, negative resist composition for color filter, color filter, liquid crystal display device, and organic light-emitting display device |
| CN102504622B (en) * | 2011-11-04 | 2014-01-15 | 湖北鼎龙化学股份有限公司 | Modified pigment and preparation method and application thereof and nanometer pigment dispersoid |
| KR101980236B1 (en) * | 2012-03-28 | 2019-05-20 | 제이에스알 가부시끼가이샤 | Colored composition, color filter, display device and pigment dispersion |
| CN108219158B (en) * | 2018-02-01 | 2020-10-13 | 吉林大学 | Covalent organic framework material and preparation method thereof |
| CN108384329A (en) * | 2018-03-21 | 2018-08-10 | 深圳市华星光电技术有限公司 | Dispersible pigment dispersion and preparation method thereof, colored photoresist |
| CN109180957A (en) * | 2018-08-29 | 2019-01-11 | 复旦大学 | Radical cation type covalent organic frame material and its preparation method and application |
| CN109320734B (en) * | 2018-10-29 | 2021-04-27 | 福州大学 | Spherical covalent organic framework material and preparation method and application thereof |
| CN110054741B (en) * | 2019-04-02 | 2020-10-30 | 深圳市华星光电技术有限公司 | Method for preparing pigment dispersion liquid |
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