CN116178989B - Blue pigment dispersion composition for color photoresist and preparation method thereof - Google Patents
Blue pigment dispersion composition for color photoresist and preparation method thereof Download PDFInfo
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- CN116178989B CN116178989B CN202310157615.4A CN202310157615A CN116178989B CN 116178989 B CN116178989 B CN 116178989B CN 202310157615 A CN202310157615 A CN 202310157615A CN 116178989 B CN116178989 B CN 116178989B
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- phthalocyanine blue
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- 239000006185 dispersion Substances 0.000 title claims abstract description 63
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 42
- 239000001055 blue pigment Substances 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims abstract description 61
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims abstract description 17
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 239000000376 reactant Substances 0.000 claims description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 17
- 239000004925 Acrylic resin Substances 0.000 claims description 16
- 229920000178 Acrylic resin Polymers 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 13
- 239000005457 ice water Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 9
- JGHKDVSIFPFNIJ-UHFFFAOYSA-N dodecylsulfanylmethanedithioic acid Chemical group CCCCCCCCCCCCSC(S)=S JGHKDVSIFPFNIJ-UHFFFAOYSA-N 0.000 claims description 9
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 238000005303 weighing Methods 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- 238000009775 high-speed stirring Methods 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 230000001376 precipitating effect Effects 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 230000005587 bubbling Effects 0.000 claims description 4
- 238000007792 addition Methods 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000002245 particle Substances 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 9
- 238000012986 modification Methods 0.000 abstract description 4
- 230000004048 modification Effects 0.000 abstract description 4
- 238000004873 anchoring Methods 0.000 abstract description 3
- -1 polysiloxane Polymers 0.000 abstract description 3
- 229920001296 polysiloxane Polymers 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000000049 pigment Substances 0.000 description 12
- 239000004576 sand Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 238000003801 milling Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0032—Treatment of phthalocyanine pigments
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0069—Non aqueous dispersions of pigments containing only a solvent and a dispersing agent
- C09B67/007—Non aqueous dispersions of phthalocyanines containing only a solvent and a dispersing agent
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
- C09B67/0082—Preparations of disperse dyes or solvent dyes in liquid form
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0091—Process features in the making of dispersions, e.g. ultrasonics
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optical Filters (AREA)
Abstract
The invention relates to a blue pigment dispersion composition for color photoresist and a preparation method thereof. According to the blue pigment dispersion composition provided by the invention, phthalocyanine blue 15:6 is used as a raw material to carry out self-separation modification, and the surface of the phthalocyanine blue 15:6 is effectively coated with polysiloxane containing C=C double bonds by using vinyl triethoxysilane and tetraethyl orthosilicate as raw materials, and then scattering structural substances are further synthesized, so that the prepared self-dispersion phthalocyanine blue 15:6 has smaller particle size, smaller viscosity, larger contact angle, higher temperature stability and centrifugal stability due to the combined action of the scattering structure and an excellent anchoring group, is suitable for the high-precision requirement of photoresist, and expands the application of the phthalocyanine blue raw material in the photoresist.
Description
Technical Field
The invention belongs to the technical field of photoresist, and particularly relates to a blue pigment dispersion composition for color photoresist and a preparation method thereof.
Background
In the age of high-speed development of communication and display technology, a liquid crystal display screen on electronic equipment such as mobile phones, televisions, computers and intelligent wearable equipment provides a large amount of visual information for people, and becomes an indispensable part of daily life of people. The core component of the liquid crystal display screen is a light filter, and the cost of the light filter occupies about one fifth of the cost of the whole liquid crystal display screen. The color resistance layer of the color filter generally comprises a patterned red color resistance unit, a patterned green color resistance unit and a patterned blue color resistance unit, the backlight respectively forms red light, green light and blue light after passing through the red color resistance unit, the green light and the blue light, the liquid crystal display realizes the target color by controlling different brightness combinations of the red light, the green light and the blue light, and the patterned red color resistance unit, the patterned green color resistance unit and the patterned blue color resistance unit are generally manufactured by using color photoresist. The ideal filter should have high contrast, color saturation, high transmittance, and high color purity. Examples of the method for producing the optical filter include a dyeing method, a pigment dispersion method, a transfer method, and an inkjet method.
The current method for producing the optical filter is mainly pigment dispersion method. The color filter produced by the pigment dispersion method has good light resistance and heat resistance, is stable when being irradiated by a backlight source, has high chemical stability and good acid-base tolerance to the technological process, and in addition, the filter manufactured by the pigment dispersion method has high brightness, transmittance and color purity. The pigment dispersing process includes mainly the steps of coating, exposure and development. The pigment dispersing method is to disperse pigment in resin to prepare pigment dispersing liquid, and to add monomer and photoinitiator into the pigment dispersing liquid to prepare photoresist. The pigment molecules have larger specific surface area and higher surface free energy, so that aggregation is easier, and therefore, the particle size and the stability are difficult to be combined. Phthalocyanine blue, pigment blue 15, has bright color and excellent performance, is a 18-electron macrocyclic ring, and has very wide application due to its stable structure. However, the phthalocyanine blue pigment has a very limited application range because of its low polarity and poor dispersibility.
Disclosure of Invention
The invention aims to provide a blue pigment dispersion composition for color photoresist and a preparation method thereof. According to the blue pigment dispersion composition provided by the invention, phthalocyanine blue 15:6 is used as a raw material to carry out self-separation modification, and the surface of the phthalocyanine blue 15:6 is effectively coated with polysiloxane containing C=C double bonds by using vinyl triethoxysilane and tetraethyl orthosilicate as raw materials, and then scattering structural substances are further synthesized, so that the prepared self-dispersion phthalocyanine blue 15:6 has smaller particle size, smaller viscosity, larger contact angle, higher temperature stability and centrifugal stability due to the combined action of the scattering structure and an excellent anchoring group, is suitable for the high-precision requirement of photoresist, and expands the application of the phthalocyanine blue raw material in the photoresist.
The technical problems to be solved by the invention can be realized by the following scheme:
a blue pigment dispersion composition for a color photoresist is prepared by the following preparation method:
(1) Weighing phthalocyanine blue 15:6, cetyl trimethyl ammonium bromide and deionized water, uniformly stirring and mixing, sanding for 2-3 hours, dropwise adding an ammonia water solution, tetraethyl orthosilicate and vinyl triethoxysilane mixed solution under high-speed stirring, and stirring for reaction to obtain pre-dispersed phthalocyanine blue 15:6;
(2) Weighing and sequentially adding 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, dioxane, dimethylaminoethyl methacrylate and azodiisobutyronitrile, bubbling nitrogen for 30min, and then preserving heat in an oil bath; cooling with ice water after the reaction is finished to prepare a pre-reactant;
(3) Adding the pre-reactant, dioxane and azodiisobutyronitrile into pre-dispersed phthalocyanine blue 15:6, bubbling nitrogen for 30min, and then preserving heat in an oil bath; cooling with ice water after the reaction is finished; precipitating with excessive n-hexane solution, and washing for 3-4 times; drying the filtered product for 24 hours to obtain self-dispersed phthalocyanine blue 15:6;
(4) Mixing self-dispersion phthalocyanine blue 15:6, acrylic resin and solvent to prepare a blue pigment dispersion composition for the color photoresist; wherein the self-dispersing phthalocyanine blue 15:6 is 10-15 parts by weight, the acrylic resin is 10-30 parts by weight, and the solvent is 45-55 parts by weight.
As a preferred scheme of the invention, the dosage ratio of the phthalocyanine blue 15:6, the hexadecyl trimethyl ammonium bromide and the deionized water in the step (1) is 1-2g:0.5-1g:100mL.
As a preferable scheme of the invention, the mass fraction of the ammonia water after the completion of the dropwise addition in the step (1) is 0.10-0.12%, the mass fraction of the tetraethyl orthosilicate is 0.7-0.8%, and the mass fraction of the vinyl triethoxysilane is 0.7-0.8%.
As a preferable mode of the invention, the mass ratio of the tetraethyl orthosilicate to the vinyl triethoxysilane in the step (1) is 1:1.
As a preferable mode of the invention, the stirring reaction time in the step (1) is 24 hours, and the stirring temperature is 30 ℃.
As a preferable mode of the invention, in the step (2), the mass ratio of the 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, dioxane, dimethylaminoethyl methacrylate and azodiisobutyronitrile is 0.35-0.4:10.5-11:4-4.5:0.01-0.02.
As a preferable scheme of the invention, the temperature of the oil bath in the steps (2) and (3) is 100-220 ℃, and the heat preservation time is 6-8h.
As a preferable scheme of the invention, the mass ratio of the pre-reactant, the dioxane and the azodiisobutyronitrile in the step (3) is 3.5-4:2-3:0.001.
As a preferred embodiment of the invention, the mass ratio of the pre-reactant to the pre-dispersed phthalocyanine blue 15:6 in the step (3) is 1:2.5-4.
The invention has the beneficial effects that:
1. the blue pigment dispersion composition for the color photoresist provided by the invention uses the phthalocyanine blue 15:6 as a raw material to carry out self-dispersing modification on the blue pigment dispersion composition, and the prepared blue pigment dispersion composition shows good self-dispersing performance in a solvent, so that the application of the phthalocyanine blue raw material in the photoresist is enlarged.
2. According to the invention, vinyl triethoxysilane and tetraethyl orthosilicate are used as raw materials, polysiloxane containing C=C double bonds is effectively coated on the surface of phthalocyanine blue 15:6, when the mass fraction of ammonia water is 0.10% -0.12%, the C=C double bonds coated on the surface of pigment are the largest, the contact angle is the highest and reaches 85 degrees, and at the moment, the dispersion efficiency of phthalocyanine blue 15:6 is the largest.
3. The self-dispersing phthalocyanine blue 15:6 prepared by the method has a scattering structure, small particle size, low viscosity and high stability, and the result of the combined action of the scattering structure and an excellent anchoring group enhances the steric hindrance, and the tertiary amine can be complexed with unreacted pigment particles to improve the dispersing efficiency.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
A blue pigment dispersion composition for a color photoresist is prepared by the following preparation method:
(1) Weighing 15:61.0450g of phthalocyanine blue, 0.5162g of cetyl trimethyl ammonium bromide and 50mL of deionized water, stirring and mixing uniformly, placing into a sand mill for sand milling, adding into a 250mL three-neck flask after 2 hours, and dripping a mixed solution of ammonia water solution, tetraethyl orthosilicate and vinyl triethoxysilane under high-speed stirring; so that the mass fraction of the ammonia water after dripping is 0.10%, the mass fraction of the tetraethyl orthosilicate is 0.7%, and the mass fraction of the vinyl triethoxysilane is 0.7%; reacting for 24 hours at 30 ℃ under stirring to obtain pre-dispersed phthalocyanine blue 15:6;
(2) 0.3170g of 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, 10.6410g of dioxane, 4.0820g of dimethylaminoethyl methacrylate and 0.0124g of azobisisobutyronitrile were weighed into a 50mL three-necked flask in sequence; introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, and preserving heat for 6h at 100 ℃; cooling with ice water after the reaction is finished to prepare a pre-reactant;
(3) Adding the prepared pre-reactant, dioxane, azodiisobutyronitrile and pre-dispersed phthalocyanine blue 15:6 according to the mass ratio of 3.5:2:0.001:8, introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, preserving heat for 6h at 100 ℃, and cooling with ice water after the reaction is finished; precipitating with excessive n-hexane solution, and washing for 3 times; drying the filtered product for 24 hours to obtain self-dispersed phthalocyanine blue 15:6;
(4) Mixing self-dispersion phthalocyanine blue 15:6, acrylic resin and solvent to prepare a blue pigment dispersion composition for the color photoresist; wherein, the self-dispersion phthalocyanine blue 15:6 is 10 weight parts, acrylic resin 10 weight parts, water 45 weight parts.
Example 2
A blue pigment dispersion composition for a color photoresist is prepared by the following preparation method:
(1) Weighing 15:61.5029g of phthalocyanine blue, 0.5241g of cetyl trimethyl ammonium bromide and 50mL of deionized water, uniformly stirring and mixing, placing into a sand mill for sand milling, adding into a 250mL three-neck flask after 2 hours, and dropwise adding an ammonia water solution, tetraethyl orthosilicate and vinyl triethoxysilane mixed solution under high-speed stirring; so that the mass fraction of the ammonia water after dripping is 0.105%, the mass fraction of the tetraethyl orthosilicate is 0.725%, and the mass fraction of the vinyl triethoxysilane is 0.725%; reacting for 24 hours at 30 ℃ under stirring to obtain pre-dispersed phthalocyanine blue 15:6;
(2) 0.3806g of 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, 10.8513g of dioxane, 4.1066g of dimethylaminoethyl methacrylate and 0.0103g of azobisisobutyronitrile were weighed into a 50mL three-necked flask in sequence; introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, and preserving heat for 7h at 140 ℃; cooling with ice water after the reaction is finished to prepare a pre-reactant;
(3) Adding the prepared pre-reactant, dioxane, azodiisobutyronitrile and pre-dispersed phthalocyanine blue 15:6 according to the mass ratio of 3.5:2:0.001:10, introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, preserving heat for 7h at 140 ℃, and cooling with ice water after the reaction is finished; precipitating with excessive n-hexane solution, and washing for 3 times; drying the filtered product for 24 hours to obtain self-dispersed phthalocyanine blue 15:6;
(4) Mixing self-dispersion phthalocyanine blue 15:6, acrylic resin and solvent to prepare a blue pigment dispersion composition for the color photoresist; wherein, the self-dispersion phthalocyanine blue 15:6 is 11 weight parts, the acrylic resin 15 weight parts and the solvent 47 weight parts.
Example 3
A blue pigment dispersion composition for a color photoresist is prepared by the following preparation method:
(1) Weighing 15:61.0142g of phthalocyanine blue, 0.9748g of cetyl trimethyl ammonium bromide and 50mL of deionized water, stirring and mixing uniformly, then placing into a sand mill for sand milling, adding into a 250mL three-neck flask after 3 hours, and dropwise adding an ammonia water solution, tetraethyl orthosilicate and vinyl triethoxysilane mixed solution under high-speed stirring; so that the mass fraction of the ammonia water after dripping is 0.113%, the mass fraction of the tetraethyl orthosilicate is 0.76%, and the mass fraction of the vinyl triethoxysilane is 0.76%; reacting for 24 hours at 30 ℃ under stirring to obtain pre-dispersed phthalocyanine blue 15:6;
(2) 0.3082g of 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, 10.5077g of dioxane, 4.4395g of dimethylaminoethyl methacrylate and 0.0172g of azobisisobutyronitrile were weighed into a 50mL three-necked flask in sequence; introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, and preserving heat for 7h at 180 ℃; cooling with ice water after the reaction is finished to prepare a pre-reactant;
(3) Adding the prepared pre-reactant, dioxane, azodiisobutyronitrile and pre-dispersed phthalocyanine blue 15:6 according to the mass ratio of 3.5:2:0.001:13, introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, preserving heat for 7h at 180 ℃, and cooling with ice water after the reaction is finished; precipitating with excessive n-hexane solution, and washing for 4 times; drying the filtered product for 24 hours to obtain self-dispersed phthalocyanine blue 15:6;
(4) Mixing self-dispersion phthalocyanine blue 15:6, acrylic resin and solvent to prepare a blue pigment dispersion composition for the color photoresist; wherein, the self-dispersion phthalocyanine blue 15:6 is 13 weight parts, the acrylic resin is 20 weight parts, and the solvent is 50 weight parts.
Example 4
A blue pigment dispersion composition for a color photoresist is prepared by the following preparation method:
(1) Weighing phthalocyanine blue 15:6.9635 g, cetyl trimethyl ammonium bromide 0.4976g and deionized water 50mL, stirring and mixing uniformly, then placing into a sand mill for sand milling, adding into a 250mL three-neck flask after 3 hours, and dripping an ammonia water solution, tetraethyl orthosilicate and vinyl triethoxysilane mixed solution under high-speed stirring; so that the mass fraction of the ammonia water after dripping is 0.12%, the mass fraction of the tetraethyl orthosilicate is 0.8%, and the mass fraction of the vinyl triethoxysilane is 0.8%; reacting for 24 hours at 30 ℃ under stirring to obtain pre-dispersed phthalocyanine blue 15:6;
(2) 0.3916g of 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, 10.9230g of dioxane, 4.4172g of dimethylaminoethyl methacrylate and 0.0187g of azobisisobutyronitrile were weighed into a 50mL three-necked flask in sequence; introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, and preserving heat for 8h at 220 ℃; cooling with ice water after the reaction is finished to prepare a pre-reactant;
(3) Adding the prepared pre-reactant, dioxane, azodiisobutyronitrile and pre-dispersed phthalocyanine blue 15:6 according to the mass ratio of 3.5:2:0.001:16, introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, preserving heat for 8h at 220 ℃, and cooling with ice water after the reaction is finished; precipitating with excessive n-hexane solution, and washing for 4 times; drying the filtered product for 24 hours to obtain self-dispersed phthalocyanine blue 15:6;
(4) Mixing self-dispersion phthalocyanine blue 15:6, acrylic resin and solvent to prepare a blue pigment dispersion composition for the color photoresist; wherein, the self-dispersion phthalocyanine blue 15:6 is 15 weight parts, acrylic resin 30 weight parts, solvent 55 weight parts.
Comparative example 1
A blue pigment dispersion composition for a color photoresist is prepared by the following preparation method:
(1) 0.3170g of 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, 10.6410g of dioxane, 4.0820g of dimethylaminoethyl methacrylate and 0.0124g of azobisisobutyronitrile were weighed into a 50mL three-necked flask in sequence; introducing nitrogen to bubble for 30min, transferring into an oil bath pot preheated in advance, and preserving heat for 6h at 100 ℃; cooling with ice water after the reaction is finished to prepare a pre-reactant;
(2) Mixing phthalocyanine blue 15:6, a pre-reactant, acrylic resin and a solvent to prepare a blue pigment dispersion composition for the color photoresist; wherein, the self-dispersion phthalocyanine blue 15:6 is 10 weight parts, the pre-reactant 5 weight parts, the acrylic resin 10 weight parts and the water 45 weight parts.
Comparative example 2
A blue pigment dispersion composition for a color photoresist is prepared by the following preparation method:
mixing phthalocyanine blue 15:6, a commercial dispersing agent DISPERBYK-190, acrylic resin and a solvent to prepare a blue pigment dispersion composition for the color photoresist; wherein, the self-dispersing phthalocyanine blue 15:6 is 10 weight parts, the commercial dispersing agent DISPERBYK-190 is 5 weight parts, the acrylic resin is 10 weight parts, and the water is 45 weight parts.
The blue pigment-dispersion compositions for color photoresists prepared in examples 1 to 4 and comparative examples 1 to 2 were subjected to the following test:
test example 1 particle size test
The blue pigment-dispersion composition was diluted 2000 times, the particle diameter of the dispersion at 25℃was measured using the particle size, and the average value was taken three times for each sample, and the results are shown in Table 1.
Test example 2 viscosity test
The viscosity of the blue pigment dispersion composition was measured using an RVDV-2T type viscometer using a rotor No. R4 at a temperature of 20℃to obtain the results shown in Table 1.
Test example 3 contact angle test
The blue pigment dispersion composition is prepared into 5% chloroform solution, a certain amount of solution is weighed by a dropper and uniformly coated on the surface of a clean glass slide, and the solution is dried in a vacuum drying oven at 45 ℃ to form a film. The contact angle of the polyacrylate dispersant with water was measured by using a DSA100 type contact angle measuring instrument, and the hydrophilicity was judged by the magnitude of the contact angle, and the obtained temperature stability results are shown in table 1.
Test example 4 dispersion stability
The blue pigment dispersion composition was sealed in an oven at 70℃for 24 hours, temperature stability (S r ) The calculation is carried out according to the following formula; 2mL of the sample was centrifuged at 3000r for 30min, and the centrifugation stability (S C ) The results of the temperature stability and the centrifugal stability obtained are shown in Table 1, calculated according to the following formulas.
Wherein d 0 Average particle size of the original sample
dr-average particle diameter of samples placed at different temperatures
d C Average particle size of samples treated with different centrifugation speeds
TABLE 1
As can be seen from table 1, the blue pigment dispersion compositions examples 1 to 4 provided by the present invention have smaller particle diameter, smaller viscosity, larger contact angle, higher temperature stability and centrifugal stability than the commercially available dispersant of comparative example 2 and the composition of comparative example 1 without self-dispersion treatment, which makes the phthalocyanine blue more widely used and applicable in the photoresist field.
In the description of the present specification, the descriptions of the terms "one embodiment," "example," "specific example," and the like, mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present invention. In this specification, schematic representations of the above terms do not necessarily refer to the same embodiments or examples. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is merely illustrative and explanatory of the invention, as various modifications and additions may be made to the particular embodiments described, or in a similar manner, by those skilled in the art, without departing from the scope of the invention or exceeding the scope of the invention as defined in the claims.
Claims (10)
1. A preparation method of a blue pigment dispersion composition for color photoresist is characterized in that: the method comprises the following operation steps:
(1) Weighing phthalocyanine blue 15:6, cetyl trimethyl ammonium bromide and deionized water, uniformly stirring and mixing, sanding for 2-3 hours, dropwise adding an ammonia water solution, tetraethyl orthosilicate and vinyl triethoxysilane mixed solution under high-speed stirring, and stirring for reaction to obtain pre-dispersed phthalocyanine blue 15:6;
(2) Weighing and sequentially adding 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, dioxane, dimethylaminoethyl methacrylate and azodiisobutyronitrile, bubbling nitrogen for 30min, and then preserving heat in an oil bath; cooling with ice water after the reaction is finished to prepare a pre-reactant;
(3) Adding the pre-reactant, dioxane and azodiisobutyronitrile into pre-dispersed phthalocyanine blue 15:6, bubbling nitrogen for 30min, and then preserving heat in an oil bath; cooling with ice water after the reaction is finished; precipitating with excessive n-hexane solution, and washing for 3-4 times; drying the filtered product for 24 hours to obtain self-dispersed phthalocyanine blue 15:6;
(4) Mixing self-dispersion phthalocyanine blue 15:6, acrylic resin and solvent to prepare a blue pigment dispersion composition for the color photoresist; wherein the self-dispersing phthalocyanine blue 15:6 is 10-15 parts by weight, the acrylic resin is 10-30 parts by weight, and the solvent is 45-55 parts by weight.
2. The method for preparing a blue pigment dispersion composition for color photoresists as claimed in claim 1, wherein: the dosage ratio of the phthalocyanine blue 15:6, the cetyl trimethyl ammonium bromide and the deionized water in the step (1) is 1-2g:0.5-1g:100mL.
3. The method for preparing a blue pigment dispersion composition for color photoresists as claimed in claim 1, wherein: after the completion of the dropwise addition in the step (1), the mass fraction of ammonia water is 0.10% -0.12%, the mass fraction of tetraethyl orthosilicate is 0.7% -0.8%, and the mass fraction of vinyltriethoxysilane is 0.7% -0.8%.
4. The method for preparing a blue pigment dispersion composition for color photoresists as claimed in claim 1, wherein: the mass ratio of the tetraethyl orthosilicate to the vinyl triethoxysilane in the step (1) is 1:1.
5. The method for preparing a blue pigment dispersion composition for color photoresists as claimed in claim 1, wherein: the stirring reaction time in the step (1) is 24 hours, and the stirring temperature is 30 ℃.
6. The method for preparing a blue pigment dispersion composition for color photoresists as claimed in claim 1, wherein: the mass ratio of the 2- (dodecyl trithiocarbonate group) -2-methylpropanoic acid, dioxane, dimethylaminoethyl methacrylate and azodiisobutyronitrile in the step (2) is 0.35-0.4:10.5-11:4-4.5:0.01-0.02.
7. The method for preparing a blue pigment dispersion composition for color photoresists as claimed in claim 1, wherein: the temperature of the oil bath in the steps (2) and (3) is 100-220 ℃, and the heat preservation time is 6-8h.
8. The method for preparing a blue pigment dispersion composition for color photoresists as claimed in claim 1, wherein: the mass ratio of the pre-reactant, the dioxane and the azodiisobutyronitrile in the step (3) is 3.5-4:2-3:0.001.
9. The method for preparing a blue pigment dispersion composition for color photoresists as claimed in claim 1, wherein: the mass ratio of the pre-reactant to the pre-dispersed phthalocyanine blue 15:6 in the step (3) is 1:2.5-4.
10. A blue pigment dispersion composition for color photoresists produced by the process for producing a blue pigment dispersion composition for color photoresists as claimed in any one of claims 1 to 9.
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| CN113064323A (en) * | 2021-02-07 | 2021-07-02 | 纳琳威纳米科技南通有限公司 | Photoresist pigment color paste and preparation method thereof |
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| CN113064323A (en) * | 2021-02-07 | 2021-07-02 | 纳琳威纳米科技南通有限公司 | Photoresist pigment color paste and preparation method thereof |
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Denomination of invention: A blue pigment dispersion composition for color photoresist and its preparation method Effective date of registration: 20231103 Granted publication date: 20230801 Pledgee: Bank of China Limited by Share Ltd. Zhongshan branch Pledgor: Best New Material Technology (Zhongshan) Co.,Ltd. Registration number: Y2023980064014 |