CN115124889B - Red color paste for color photoresist and preparation method thereof - Google Patents
Red color paste for color photoresist and preparation method thereof Download PDFInfo
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- CN115124889B CN115124889B CN202211050899.9A CN202211050899A CN115124889B CN 115124889 B CN115124889 B CN 115124889B CN 202211050899 A CN202211050899 A CN 202211050899A CN 115124889 B CN115124889 B CN 115124889B
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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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
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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
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Abstract
The invention belongs to the technical field of display materials, and relates to a red color paste for a color photoresist and a preparation method thereof, wherein the red color paste for the color photoresist comprises the following components in percentage by mass: 12% of red pigment; 3.5 to 5.5 percent of synthetic resin; 3.5 to 5.5 percent of dispersant; 0.1 to 1 percent of synergist; 76 to 80.9 percent of solvent; the acid value of the synthetic resin is 145 to 165mgKOH/g, the synthetic resin is acrylic resin, and the synergist is a triazine synergist. The red color paste of the color photoresist adopts the synthetic resin with high acid value and the synergist with high polarity, the polarity is close to water, the synthetic resin and the synergist are attached to the surface of the pigment, and under the combined action of the synthetic resin and the synergist, the pigment is not easy to sublimate after being heated, no sublimation foreign matters are generated, the surface quality of the photoresist is improved, the generation of poor products is reduced, and the yield is improved.
Description
Technical Field
The invention belongs to the technical field of display materials, and particularly relates to red paste for a color photoresist and a preparation method thereof.
Background
The color of a liquid crystal display is achieved by Color Filters (CF), which directly determine the quality of the color image of the display. The filter comprises a transparent substrate such as glass, a black matrix, a color photoresist layer, an overcoat layer and an Indium Tin Oxide (ITO) conductive film, wherein the color photoresist layer of the color filter comprises three-color photoresists of red, green and blue (RGB). To achieve good color reproducibility, color filters must have high color purity, high transmittance, high contrast, low reflectance, and high thermal, light and chemical resistance. The preparation technology of photoresist (photoresist) is the core technology of color filter preparation.
The photoresist comprises color paste made of pigment, light-cured resin, photoinitiator, solvent and the like. The quality of the color filter is mainly determined by the performance of the photoresist and the coating process thereof, and the preparation process of the red, green and blue pixels comprises repeated pre-baking, exposure and development, and finally, post-baking at 220-240 ℃. Pigment color paste of making often can appear sublimating the foreign matter in the postbaking after the development, we call bloming, this kind of sublimating the foreign matter not only can fall on the pixel of self, still can fall on in the pixel that closes on, influence light filter surface quality, the subliming foreign matter that produces moreover sometimes can grow out the micro-burr, this kind of micro-burr can pierce through follow-up technology ITO membrane, cause revealing of liquid crystal, perhaps puncture the circuit, so need one kind to avoid this kind of color paste and the preparation method that sublimating the foreign matter phenomenon and appear.
Disclosure of Invention
The invention provides a red color paste for a color photoresist and a preparation method thereof, aiming at the technical problem that the color paste made of red pigment has the phenomenon of subliming foreign matters in post-baking after development.
The specific technical scheme of the invention is as follows:
in order to solve the technical problems, a first object of the present invention is to provide a red paste for a color photoresist, which comprises the following components by mass percent:
12% of red pigment; 3.5 to 5.5 percent of synthetic resin; 3.5 to 5.5 percent of dispersant; 0.1 to 1 percent of synergist; 76 to 80.9 percent of solvent;
the acid value of the synthetic resin is 145 to 165mgKOH/g, and the synthetic resin is acrylic resin;
the synergist is a triazine synergist, and the molecular structural formula of the triazine synergist is as follows:
further, the synthetic resin has a solid content of 25 to 35% and a weight average molecular weight of 7500 to 9500.
Generally, the higher the weight average molecular weight, the higher the viscosity, and the viscosity required in the preparation of color paste can be achieved by reasonably controlling the weight average molecular weight of the resin and the viscosity of the resin.
Further, the preparation method of the triazine synergist comprises the following steps:
cyanuric chloride, p-phenylenediamine and water are stirred to react for 0.5 to 2 hours at the temperature of 5 to 30 ℃, p-aminobenzenesulfonic acid and 3-diethylaminopropylamine are respectively added, the stirring is continued for 2 to 4 hours at the temperature of 5 to 30 ℃ to obtain an intermediate product, N-phthaloyl glycinyl chloride is added into the intermediate product system, the reaction is carried out for 1.5 to 3 hours at the temperature of 70 to 100 ℃, the filtering is carried out, and the product is washed and dried to obtain the triazine synergist;
the reaction formula is as follows:
further, the molar ratio of cyanuric chloride to p-phenylenediamine to p-aminobenzenesulfonic acid to 3-diethylaminopropylamine to N-phthaloyl glycinyl chloride is 1: (0.5-2): (0.5-2): (0.5-2): (0.5-3).
Further, the red pigment is preferably a red pigment 291 (R-291), and the red pigment 291 is BASF C.I 291, BASF, germany.
Further, the dispersant is Byk-21116, germany Bick chemical; the solvent is propylene glycol methyl ether acetate (PMA).
The invention also aims to provide a preparation method of the red color paste for the color photoresist, which comprises the following steps:
(1) Preparing synthetic resin;
(2) Preparing color paste: weighing the materials according to the mass percent to prepare color paste, grinding and dispersing the color paste, putting into a zirconium ball of 0.1-0.3mm/100 g, and grinding for 10-1693 h to prepare red dispersion liquid, namely the red color paste for the color photoresist.
Further, the preparation method of the synthetic resin comprises the following steps:
blowing a reaction device provided with a magnetic stirring device, a condensing device and a constant pressure titration device by using nitrogen for 5 to 20 minutes; adding a solvent into the reaction device, starting stirring, and heating to 70-90 ℃; dropwise adding a mixture of a monomer for synthesizing the synthetic resin and an initiator into the reaction device, stirring for 12 hours after dropwise adding is completed within 4 hours; after the reaction is finished, adding propylene glycol methyl ether acetate into the reaction system to adjust the solid content of the resin; thus obtaining the synthetic resin.
Further, the solvent is propylene glycol methyl ether acetate, the initiator is 2,2' -azobisisobutyronitrile, and the monomer is one or more of methacrylic acid, acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, fatty alkyl group-containing (meth) acrylate, alicyclic group-containing (meth) acrylate, ether group-containing (meth) acrylate, and benzyl (meth) acrylate.
Further, the (meth) acrylate containing a fatty alkyl group is, for example, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, octadecyl (meth) acrylate, stearyl (meth) acrylate, and the like.
Further, the (meth) acrylate containing an alicyclic group is cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, or the like.
Further, the ether group-containing (meth) acrylate is methoxytriethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, methoxypropylene glycol (meth) acrylate, hexylcarbitol (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylphenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, or the like.
The red color paste of the color photoresist adopts the synthetic resin with high acid value and the synergist with high polarity, the polarity is close to water, the synthetic resin and the synergist are attached to the surface of the pigment, and under the combined action of the synthetic resin and the synergist, the pigment is not easy to sublimate after being heated after post-baking, sublimation foreign matters do not appear, the surface quality of the photoresist is improved, the generation of poor products is reduced, and the yield is improved.
Drawings
FIG. 1 is a mass spectrum of triazine synergist prepared by the present invention;
FIG. 2 is a GPC chart of the synthetic resin 1 of the present invention;
FIG. 3 is a GPC chart of synthetic resin 2 of the present invention;
FIG. 4 is a GPC chart of the synthetic resin 3 of the present invention;
FIG. 5 is a microscopic view showing the state of sublimed foreign matter in example 1 of the present invention;
FIG. 6 is a microscope observation view showing a state where foreign substances are sublimated in example 2 of the present invention;
FIG. 7 is a microscopic view showing the condition of sublimed foreign matters in example 3 of the present invention;
FIG. 8 is a microscopic observation view showing a case of subliming foreign substances according to comparative example 1 of the present invention;
FIG. 9 is a microscopic observation view showing the state of sublimed foreign matters in comparative example 2 of the present invention.
Detailed Description
The principles and features of this invention are described below in conjunction with examples, which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Preparation of triazine synergist:
cyanuric chloride (0.92g, 5 mmol), p-phenylenediamine (0.55g, 5.05mmol) and 100g of water are added into a 250mL three-neck flask, after stirring and reacting for 1h at 20 ℃, p-aminobenzenesulfonic acid (0.44g, 2.55mmol) and 3-diethylaminopropylamine (0.33g, 2.55mmol) are respectively added, stirring is continued for 2h at 20 ℃ to obtain an intermediate product, N-phthaloyl glycinyl chloride (1.13g, 5.05mmol) is added into the intermediate product system, reaction is continued for 2h at 90 ℃, filtering is carried out, the product is washed, and drying is carried out at 120 ℃ to obtain 2.40g of triazine synergist, and the quality spectrum of the prepared triazine synergist is shown in figure 1.
Example 1:
a preparation method of red paste for color photoresist comprises the following steps:
(1) Preparation of synthetic resin 1:
purging a three-neck flask with a magnetic stirring device, a condensing device and a constant pressure titration device for 10 minutes by using nitrogen; adding 200 parts of propylene glycol methyl ether acetate solvent into a flask, starting stirring, and heating to 80 ℃; dropwise adding a mixture consisting of 76 parts of benzyl methacrylate, 24 parts of methacrylic acid and 1.5 parts of 2,2' -azobisisobutyronitrile into the flask, completing dropwise adding for 4h, and continuously stirring for 12h at 80 ℃; after the reaction is finished, adding propylene glycol methyl ether acetate into the reaction system to adjust the solid content of the resin to be 30 percent, and obtaining the synthetic resin 1, wherein the weight average molecular weight of the synthetic resin 1 is 8200, and the acid value is 156mgKOH/g; the GPC image of synthetic resin 1 is shown in fig. 2;
(2) Preparing color paste:
weighing 12g of red pigment 291,3.5g of synthetic resin 1,5.5g of dispersant Byk-21116,0.6g of triazine synergist and 78.4g of PMA, adding the color slurry into a grinding tank, adding a zirconium ball of 0.3mm/100g, and grinding for 16h to obtain a red dispersion liquid, namely the red color paste for the color photoresist.
Example 2:
a preparation method of red color paste for color photoresist comprises the following steps:
(1) Preparation of synthetic resin 2:
purging a three-neck flask with a magnetic stirring device, a condensing device and a constant pressure titration device for 10 minutes by using nitrogen; adding 200 parts of propylene glycol monomethyl ether acetate solvent into a flask, starting stirring, and heating to 80 ℃; dropwise adding a mixture consisting of 75 parts of benzyl methacrylate, 25 parts of methacrylic acid and 1.5 parts of 2,2' -azobisisobutyronitrile into the flask, finishing dropwise adding for 4 hours, and continuously stirring for 12 hours at 80 ℃; after the reaction is finished, adding propylene glycol methyl ether acetate into the reaction system to adjust the solid content of the resin to be 30 percent, and obtaining synthetic resin 2, wherein the weight-average molecular weight of the synthetic resin 2 is 9100, and the acid value is 162mgKOH/g; the GPC image of synthetic resin 2 is shown in fig. 3;
(2) Preparing color paste:
12g of red pigment 291,4.2g of synthetic resin 2,4.6g of dispersant Byk-21116,0.8g of triazine synergist and 78.6g of PMA are weighed, the color slurry is added into a grinding tank, and is put into a zirconium ball of 0.3mm/100g for grinding for 16h to obtain red dispersion liquid, namely the red color paste for the color photoresist.
Example 3:
a preparation method of red color paste for color photoresist comprises the following steps:
(1) Preparation of synthetic resin 3:
purging a three-neck flask with a magnetic stirring device, a condensing device and a constant pressure titration device for 10 minutes by using nitrogen; adding 200 parts of propylene glycol monomethyl ether acetate solvent into a flask, starting stirring, and heating to 80 ℃; dripping a mixture consisting of 56.97 parts of benzyl methacrylate, 18.03 parts of hydroxyethyl methacrylate and 1.5 parts of 2,2' -azobisisobutyronitrile into the flask, finishing dripping for 4 hours, and continuously stirring for 12 hours at 80 ℃; after the reaction is finished, adding propylene glycol methyl ether acetate into the reaction system to adjust the solid content of the resin to be 30 percent, and obtaining the synthetic resin 3, wherein the weight average molecular weight of the synthetic resin 3 is 7900, and the acid value is 156mgKOH/g; the GPC image of synthetic resin 3 is shown in fig. 4;
(2) Preparing color paste:
weighing 12g of red pigment 291,5.5g of synthetic resin 3,4g of dispersing agent Byk-21116,0.2g of triazine synergist and 78.3g of PMA, adding the color slurry into a grinding tank, and putting 0.3mm/100g of zirconium balls for grinding for 16h to obtain red dispersion liquid, namely the red color paste for the color photoresist.
Comparative example 1:
weighing 12g of red pigment 291,4.2g of acrylic resin (with an acid value of 100mgKOH/g and a weight average molecular weight of 8000), 5.2g of dispersant Byk-21116 and 78.6g of PMA, adding the color slurry into a grinding tank, and putting 0.3mm/100g of zirconium balls into the grinding tank to grind for 16 hours to obtain a red dispersion liquid, namely the red color paste for the color photoresist.
Comparative example 2:
weighing 12g of red pigment 291,3.5g of acrylic resin (with an acid value of 100mgKOH/g and a weight average molecular weight of 8000), 5.5g of dispersant Byk-21116,0.6g of triazine synergist and 78.4g of PMA, adding the color slurry into a grinding tank, putting 0.3mm/100g of zirconium balls into the grinding tank, and grinding the mixture for 16 hours to obtain a red dispersion liquid, namely obtaining the red color paste for the color photoresist.
Smear detection evaluation: examples 1 to 3, comparative examples 1 to 2 were each prepared by adding a stock solution (the stock solution comprising 86.6% of PMA as a solvent, 5% of an acrylic resin, 8% of a trimethylolpropane triacrylate monomer, and 0.4% of a photoinitiator) to the red dispersion obtained in examples 1 to 3 and comparative examples 1 to 2 to prepare a resist solution, coating the resist solution on a spin coater, and after coating the resist solution, the resist solution was prebaked at 120 ℃ for 90 seconds, exposed to light, developed, placed in an airless incubator at 230 ℃ for 30 minutes, and then at 240 ℃ for 2 hours, and observed under a microscope, and the microscope observation patterns of examples 1 to 3 and comparative examples 1 to 2 were shown in FIGS. 5 to 9.
In summary, as can be clearly seen from the microscope observation images of the examples 1 to 3 and the comparative examples 1 to 2, the red paste for color photoresist and the preparation method thereof provided by the invention can effectively solve the technical problem that the sublimation foreign matters appear in the post-baking of the red pixel formed after the development of the photoresist made of the red paste by using the synthesized acrylic resin with the acid value of 145 to 165mgkoh/g in combination with the synergist, thereby being beneficial to improving the surface quality of the photoresist, reducing the generation of defective products and improving the yield.
It is to be understood that the present invention has been described with reference to certain embodiments, and that various changes in the features and embodiments, or equivalent substitutions may be made therein by those skilled in the art without departing from the spirit and scope of the invention. In addition, many modifications may be made to adapt a particular situation or material to the teachings of the invention without departing from the essential scope thereof. Therefore, it is intended that the invention not be limited to the particular embodiment disclosed, but that the invention will include all embodiments falling within the scope of the appended claims.
Claims (5)
1. The red paste for the color photoresist is characterized by comprising the following components in percentage by mass:
12% of red pigment; 3.5 to 5.5 percent of synthetic resin; 3.5 to 5.5 percent of dispersant; 0.1 to 1 percent of synergist; 76 to 80.9 percent of solvent;
the acid value of the synthetic resin is 145 to 165mgKOH/g, and the synthetic resin is acrylic resin; the solid content of the synthetic resin is 25-35%, and the weight average molecular weight is 7500-9500;
the preparation method of the synthetic resin comprises the following steps: purging a reaction device provided with a magnetic stirring device, a condensing device and a constant pressure titration device for 5 to 20 minutes by using nitrogen; adding a solvent into the reaction device, starting stirring, and heating to 70-90 ℃; dropwise adding a mixture of a monomer for synthesizing the synthetic resin and an initiator into the reaction device, stirring for 12 hours after dropwise adding is completed within 4 hours; after the reaction is finished, adding propylene glycol methyl ether acetate into the reaction system to adjust the solid content of the resin;
the solvent is propylene glycol methyl ether acetate, the initiator is 2,2' -azobisisobutyronitrile, and the monomer is one or more of methacrylic acid, acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, fatty alkyl-containing (meth) acrylate, alicyclic group-containing (meth) acrylate, ether-containing (meth) acrylate and benzyl (meth) acrylate;
the synergist is a triazine synergist, and the molecular structural formula of the triazine synergist is as follows:
the preparation method of the triazine synergist comprises the following steps:
cyanuric chloride, p-phenylenediamine and water are stirred and react for 0.5 to 2 hours at the temperature of 5 to 30 ℃, p-aminobenzenesulfonic acid and 3-diethylaminopropylamine are respectively added, the stirring is continued for 2 to 4 hours at the temperature of 5 to 30 ℃ to obtain an intermediate product, N-phthaloyl glycinyl chloride is added into the intermediate product system, the reaction is carried out for 1.5 to 3 hours at the temperature of 70 to 100 ℃, the filtration is carried out, and the product is washed and dried to obtain the triazine synergist;
wherein the molar ratio of cyanuric chloride to p-phenylenediamine to p-aminobenzenesulfonic acid to 3-diethylaminopropylamine to N-phthaloyl glycinoyl chloride is 1: (0.5-2): (0.5-2): (0.5-2): (0.5-3);
the reaction formula is as follows:
2. the red paste for color photoresists according to claim 1, wherein the red pigment is red pigment 291; the dispersant is Byk-21116; the solvent is propylene glycol methyl ether acetate (PMA).
3. A method for preparing a red paste for a color photoresist according to any one of claims 1 to 2, comprising the steps of:
(1) Preparing synthetic resin;
(2) Preparing color paste: weighing the materials according to the mass percent to prepare color paste, grinding and dispersing the color paste, putting the color paste into a zirconium ball with the diameter of 0.1 to 0.3mm/100g, and grinding the mixture for 10 to 169h to prepare red dispersion liquid, namely the red color paste for the color photoresist.
4. The method of claim 3, wherein the (meth) acrylate containing an aliphatic alkyl group is n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, dodecyl (meth) acrylate (lauryl (meth) acrylate), or octadecyl (meth) acrylate (stearyl (meth) acrylate).
5. The method of claim 4, wherein the (meth) acrylate containing an alicyclic group is cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate; the (meth) acrylate containing an ether group is methoxy triethylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, methoxy dipropylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, methoxy polypropylene glycol (meth) acrylate, hexyl carbitol (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, phenoxy diethylene glycol (meth) acrylate, p-nonylphenoxyethyl (meth) acrylate, p-phenoxy polyethylene glycol (meth) acrylate.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1854202A (en) * | 2005-04-19 | 2006-11-01 | 大日精化工业株式会社 | Pigment dispersants and their use |
| CN101541898A (en) * | 2007-06-21 | 2009-09-23 | 三菱化学株式会社 | Pigment dispersion, coloring composition for color filter, color filter, liquid crystal display and organic EL display |
| US20100159371A1 (en) * | 2008-12-19 | 2010-06-24 | Boe Technology Group Co., Ltd. | Pigment dispersion solution, pigment photoresist and color filter |
| CN105934712A (en) * | 2014-01-17 | 2016-09-07 | 三星Sdi株式会社 | Photosensitive resin composition for color filter and color filter using same |
| CN114105896A (en) * | 2021-11-17 | 2022-03-01 | 山东凯瑞尔光电科技有限公司 | Pigment synergist and preparation method thereof, photoresist composition and optical filter |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1854202A (en) * | 2005-04-19 | 2006-11-01 | 大日精化工业株式会社 | Pigment dispersants and their use |
| CN101541898A (en) * | 2007-06-21 | 2009-09-23 | 三菱化学株式会社 | Pigment dispersion, coloring composition for color filter, color filter, liquid crystal display and organic EL display |
| US20100159371A1 (en) * | 2008-12-19 | 2010-06-24 | Boe Technology Group Co., Ltd. | Pigment dispersion solution, pigment photoresist and color filter |
| CN105934712A (en) * | 2014-01-17 | 2016-09-07 | 三星Sdi株式会社 | Photosensitive resin composition for color filter and color filter using same |
| CN114105896A (en) * | 2021-11-17 | 2022-03-01 | 山东凯瑞尔光电科技有限公司 | Pigment synergist and preparation method thereof, photoresist composition and optical filter |
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