CN113881246B - Modified red color sinking pigment for photoresist, preparation method and application thereof - Google Patents
Modified red color sinking pigment for photoresist, preparation method and application thereof Download PDFInfo
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- CN113881246B CN113881246B CN202010635496.5A CN202010635496A CN113881246B CN 113881246 B CN113881246 B CN 113881246B CN 202010635496 A CN202010635496 A CN 202010635496A CN 113881246 B CN113881246 B CN 113881246B
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- 239000000049 pigment Substances 0.000 title claims abstract description 80
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 14
- 238000004898 kneading Methods 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000001054 red pigment Substances 0.000 claims abstract description 19
- 239000002270 dispersing agent Substances 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 22
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 10
- 239000001055 blue pigment Substances 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000000227 grinding Methods 0.000 claims description 7
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 6
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 claims description 5
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical group [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 description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000004062 sedimentation Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 4
- 230000004048 modification Effects 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000002245 particle Substances 0.000 abstract description 31
- 239000000463 material Substances 0.000 abstract description 12
- 230000000052 comparative effect Effects 0.000 description 20
- 238000010586 diagram Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- AMVQGJHFDJVOOB-UHFFFAOYSA-H aluminium sulfate octadecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O AMVQGJHFDJVOOB-UHFFFAOYSA-H 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- JSPKFLGISILEDM-UHFFFAOYSA-N phenol;styrene Chemical compound OC1=CC=CC=C1.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 JSPKFLGISILEDM-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
-
- 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
- C09B63/00—Lakes
-
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0002—Grinding; Milling with solid grinding or milling assistants
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- 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
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Optical Filters (AREA)
Abstract
The present invention provides a modified red color sink pigment for a photoresist, the modified red color sink pigment including a red color sink pigment and TSP. In comparison with the conventional kneading pigment treatment, the present invention adopts the addition of the dispersant TSP in kneading, so that the particle size of the kneaded red pigment is small. The invention can obtain the red pigment which is easy to grind and disperse, further can ensure that the prepared color paste has smaller granularity, obtains high brightness and contrast and has good thermal stability. The invention can greatly improve the performance of the finished product by only adding one material in the original kneading process, and has the advantages of low cost of raw materials, low cost and good repeatability.
Description
Technical Field
The invention belongs to the field of liquid crystal display materials, and particularly relates to a modified red color sinking pigment for photoresist, a preparation method and application thereof.
Background
In the field of flat panel displays, TFT-LCDs (thin film transistor liquid crystal displays) are the mainstream of the market, and Color Filters (CF) are key devices for realizing color display by TFT-LCDs, which directly determine the quality of color images of the display. In the preparation of color filters, pigment dispersion is the most common, and color photoresists (photoresists) are the most important materials in the process.
The quality of the color filter mainly depends on the performance of the pigment photoresist and the coating process thereof, wherein the quality of the pigment serving as a colorant is one of main influencing factors, and in order to fully exert the tinting strength and vividness of the pigment and obtain good spectral characteristics, pigment particles must be dispersed in the pigment photoresist in a fine, uniform and stable state as far as possible, mainly high-grade organic pigment varieties are selected, and pigment dispersion-color paste with fine and stable particle size is obtained through an efficient dispersion treatment process. The dispersion state of the pigment and the particle size determine whether the final coating has high transmittance and high contrast.
The pigments should be selected based on obtaining a high definition spectrum, eliminating unnecessary wavelength spectra, and retaining only the necessary color light. The color filter can also be improved in chromaticity and transmittance by selecting the organic pigment variety meeting the requirements. The basic colors are red, green and blue, and for a blue coating, the expected brightness (Y) and contrast are difficult to obtain only by using a blue pigment alone, so that a small amount of red pigment is required to be added to adjust the spectrum, but the final optical requirement cannot be met by adopting a common red pigment and a common kneading formula; if the B02 (Acid red 52) dye is directly used, the transmittance can be improved, but the thermal stability cannot meet the requirement.
Disclosure of Invention
Therefore, the invention aims to overcome the defects in the prior art and provide a modified red color sink pigment for photoresist, a preparation method and application thereof.
Before setting forth the present disclosure, the terms used herein are defined as follows:
the term "TSP" refers to: tristyrene phenol polyoxyethylene ether, tristyrylphenol polyoxyethylene ether, CAS number 99734-09-5.
The term "DEG" means: diethylene glycol, CAS number 111-46-6.
The term "PMA" refers to: propylene glycol methyl ether acetate.
The term "B02-L" means: b02 color sinking pigment lake pigment.
The term "Blue 15:6" refers to: pigment blue 15:6.
To achieve the above object, a first aspect of the present invention provides a modified red color sink pigment for a photoresist, the modified red color sink pigment including a red color sink pigment and TSP.
The modified red color shade pigment according to the first aspect of the present invention, wherein the red color shade pigment is a B02-L red color shade pigment;
preferably, the B02-L red color counterstain is prepared by the following method: dissolving Acid red 52 dye in methanol, and dripping Al 2 (SO4) 3 .18H 2 And (3) reacting the O solution, filtering and drying to obtain a precipitate substance which is the B02-L red pigment.
A second aspect of the present invention provides the method for producing a modified red color sink pigment according to the first aspect, which is a kneading modification treatment method;
preferably, the preparation method may comprise the steps of:
(1) Adding a red color counterstain, naCl, DEG and TSP into a kneader, and heating and grinding;
(2) Washing the product obtained in the step (1);
(3) And (5) centrifugally drying to obtain the modified red color sinking pigment.
According to the preparation method of the second aspect of the invention, in the step (1), the weight part ratio of the raw materials is 1 part of red color sedimentation raw materials, 7-15 parts of NaCl, 1.5-3 parts of DEG and 0.05-0.1 part of TSP;
preferably, 1 part of red color sedimentation raw material, 10-12.5 parts of NaCl, 2-3 parts of DEG and 0.075-0.1 part of TSP.
The preparation method according to the second aspect of the present invention, wherein in the step (1), the heating temperature is 30 to 60 ℃, preferably 40 ℃; and/or
The grinding time is 8 to 14, preferably 10 to 12 hours.
The preparation method according to the second aspect of the present invention, wherein, in the step (2), the product obtained in the step (1) is washed with water to a conductivity of less than 0.1us/cm, preferably less than 0.08us/cm.
The preparation method according to the second aspect of the present invention, wherein, in the step (3), the drying temperature is 60 to 100 ℃, preferably 70 to 90 ℃, and most preferably 80 ℃.
A third aspect of the present invention provides a photoresist composition comprising a resin, a dispersant, a solvent, a blue pigment, a modified red pigment according to the first aspect or a modified red pigment prepared according to the method of the second aspect;
preferably, the blue pigment is pigment blue 15:6.
The photoresist composition according to the second aspect of the invention, wherein, in the photoresist composition, the mass part ratio of each raw material is 10-20 parts of resin, 5-10 parts of dispersing agent, 65-70 parts of solvent, 10-15 parts of blue pigment and 0.1-0.5 part of modified red pigment;
preferably, the raw materials comprise, by mass, 14-15 parts of resin, 7-8 parts of dispersing agent, 67-68 parts of solvent, 10-13 parts of blue pigment and 0.3-0.5 part of modified red pigment;
further preferably, the photoresist composition further comprises a photo-curable resin, a photoinitiator and an additive.
A fourth aspect of the present invention provides a color filter comprising a substrate and a photoresist composition according to the third aspect coated on the substrate and cured.
The invention relates to a kneading modification treatment technology of a red pigment for a color photoresist blue paste for a liquid crystal display color filter. Aiming at the defects of the prior art, the invention adopts B02-L color sinking pigment based on the prior kneading process, and the B02-LN color sinking pigment with low cost and simple process is obtained by adding TSP for kneading, so that the prepared color paste smear has good thermal stability and high brightness (Y) and contrast, and can be used as red color sinking pigment for color filter blue color paste.
The invention provides a kneading modification treatment technology of red pigment for color photoresist blue color paste, which comprises the following ingredients:
the mixture ratio of the kneading materials is as follows:
the common kneading materials are pigment, naCl and DEG, and the TSP is added in the invention, so that the TSP can be well adhered to the surface of the pigment crushed by NaCl in the kneading process, the inter-particle repulsive stability is increased, the particle size of the kneaded pigment is more uniform and stable, the particle size of the prepared color paste is further ensured to be smaller, and the contrast ratio measured after tabletting is higher than that of the pigment without adding the TSP.
The invention adds dispersant TSP in kneading, the proportion of TSP is 1/10-1/20 of B02 color sinking pigment.
The technical scheme adopted by the invention is as follows:
1) The mixture ratio of the kneading materials is as follows:
2) Kneading;
3) Vibrating and dispersing;
4) And (5) smear evaluation.
The kneader is a 1 liter kneader, and the power of the oscillator is 0.55KW.
The modified red color sink pigments of the present invention may have, but are not limited to, the following
The beneficial effects are that:
1. in the present invention, the pigment B02-L is used as a pigment sedimentation pigment, and the dispersant TSP is added during kneading, so that the particle size of the pigment after kneading is small, compared with the conventional kneading pigment treatment.
2. The invention can obtain the red pigment which is easy to grind and disperse, further can ensure that the prepared color paste has smaller granularity, obtains high brightness and contrast and has good thermal stability.
3. The invention can greatly improve the performance of the finished product by adding one material in the original kneading process, has low cost of raw materials and good repeatability,
drawings
Embodiments of the present invention are described in detail below with reference to the attached drawing figures, wherein:
FIG. 1 shows TEM photographs of red color sink pigments B02-L prepared in comparative example 2.
FIG. 2 shows a TEM photograph of the modified red color sink pigment B02-LN-1 after kneading prepared in example 1.
FIG. 3 shows a TEM photograph of the modified red color sink pigment B02-LN-2 after kneading prepared in example 2.
Fig. 4 shows a particle size diagram of the color paste prepared in comparative example 1.
Fig. 5 shows a particle size diagram of the color paste prepared in comparative example 2.
Fig. 6 shows a particle size diagram of the color paste prepared in example 1.
Fig. 7 shows a particle size diagram of the color paste prepared in example 2.
Detailed Description
The invention is further illustrated by the following specific examples, which are, however, to be understood only for the purpose of more detailed description and are not to be construed as limiting the invention in any way.
This section generally describes the materials used in the test of the present invention and the test method. Although many materials and methods of operation are known in the art for accomplishing the objectives of the present invention, the present invention will be described in as much detail herein. It will be apparent to those skilled in the art that in this context, the materials and methods of operation used in the present invention are well known in the art, if not specifically described.
The reagents and instrumentation used in the following examples were as follows:
reagent:
blue 15:6, purchased from DIC; acid red 52 (B02), purchased from Clariant; al2 (SO 4) 3.18H2O, methanol, purchased from bulk chemicals; DEG, purchased from Shandong Rui Kong chemical; TSP, purchased from chinese medicine; BYK 2001, available from Pick chemistry; resins from comprehensive research chemistry; PMA, purchased from Jiangsu Yida chemistry; salt, from Weifang Dakang chemical industry, zirconium ball, from Tosoh Co.
Instrument:
kneader, purchased from gao flight machinery, model NH-1;
vibration machine, purchased from Shenzhen star instrument model: KSF-370;
spin coater, available from Analysis, model EZ-6;
heating plate, purchased from beijing, chinese and western distal science and technology TH48SYBP;
oven, model BPG-9050AH, purchased from Shanghai Yiheng
A spectrocolorimeter, commercially available from KONICA, model CM-5;
contrast instrument, model CT1STB1, purchased from japan pot motor;
transmission electron microscope, model JEM-1400, japan electronics Co;
particle sizer, available from bruexploiting model 90Plus Pals.
The following examples were prepared from the following raw materials:
wherein the comparative example differs from the example only in the kind of red pigment.
Synthesis example 1
This synthesis example is used to illustrate the preparation of a B02-L color-sinking pigment (lake pigment):
dissolving B02 (Acid red 52) dye in methanol, and dripping Al 2 (SO4) 3 .18H 2 The solution of O is prepared from the solution of O,the precipitate obtained is filtered and dried- -B02-L pigment.
The specific synthesis method comprises the following steps:
100g of Acid red 52 (B02) is taken and dissolved in 1500g of methanol, and 15 percent of Al is dripped 2 (SO4) 3 .18H 2 590g of O solution. Filtering and drying the precipitate to obtain the B02-L color precipitate pigment.
Example 1
The method for kneading and modifying the red color counterstain pigment provided by the embodiment comprises the following specific steps:
1. kneading
1-1 into a kneader having a capacity of 1L, 80g of B02-L color pigment (lake pigment), 1000g of salt (NaCl), 160g of DEG,8g of TSP obtained in Synthesis example 1 were charged, and the mixture was ground for 12 hours at a temperature of 40 ℃. The salt functions to break up the pigment during kneading; DEG has the effect of wetting the pigment and salt to break it up in the wet state, while DEG also has the effect of inhibiting crystal growth.
1-2. Washing the kneaded material with water to a conductivity of less than 0.08uS/cm, wherein the salt and DEG in the kneaded material are removed during the washing, and TSP is grafted onto the red pigment during the kneading.
And 1-3, drying at 80 ℃ after centrifugation to obtain the modified red color sink pigment-B02-LN-1 after kneading. 2. And (3) pigment dispersion:
into a stainless steel vessel were charged 0.3g of B02-LN-1 pigment obtained by the above kneading process, 7.5g of BYK dispersant product BYK-2001, 14.1g of acrylic resin (solid content NV% = 35%), 11g of pigment blue 15:6, 67.1g of solvent PMA. 150g of 0.3mm zirconium ball is added and put into a vibration machine to be dispersed for 4 hours, thus obtaining an evaluation composition, namely color paste.
3.1 ml of the composition color paste for evaluation prepared in the step 2 was spin-coated on a glass sheet at 800rpm, the coated glass sheet was placed on a heating plate at 120℃for 1min, and after heating at 230℃in an oven for 30min, chromaticity (x, Y) and luminance (Y) were measured by a spectrocolorimeter, and contrast was measured by a contrast meter. Then the coated glass sheet is put into an oven at 230 ℃ for 1h, and the color change before and after the measurement is carried out
ΔEab, and their thermal stability was compared.
TABLE 1 kneading modified red color sink pigment Properties prepared in example 1
| Comparative example 1 | Comparative example 2 | Example 1 | |
| x | 0.1345 | 0.1347 | 0.1349 |
| y | 0.1034 | 0.1034 | 0.1034 |
| Brightness (Y) | 11.5 | 11 | 12.5 |
| Contrast ratio | 7686 | 7257 | 8800 |
| Chromaticity change DeltaEab (230 ℃ C. 1 h) | 3.4 | 0.55 | 0.5 |
FIG. 1 shows TEM photographs of the kneaded red color sink pigments B02-L prepared in comparative example 2. FIG. 2 shows a TEM photograph of the modified red color sink pigment B02-LN-1 after kneading prepared in example 1.
Fig. 4 shows a particle size diagram of the color paste prepared in comparative example 1. Fig. 5 shows a particle size diagram of the color paste prepared in comparative example 2. Fig. 6 shows a particle size diagram of the color paste prepared in example 1.
As can be seen from TEM photographs of FIGS. 1 and 2, the particle size (about 100 nm) of comparative example 2 (FIG. 1) is much larger than that (about 50 nm) of example 1 (FIG. 2), indicating that the particle size of color-sink pigment B02-LN is greatly reduced after the addition of TSP and kneading; as can be seen from the graphs of particle sizes of FIGS. 4, 5 and 6, under the same grinding and dispersing conditions, the D50 of example 1 is 52.81nm, which is smaller than the particle size (63.51 nm) of comparative example 1 and is far smaller than the particle size (75.30 nm) of comparative example 2, which shows that the addition of the color sink pigment B02-LN after TSP kneading has an obvious effect on the reduction of the particle size of the blue color paste, and further shows that the brightness and contrast of the final film layer are greatly improved.
Example 2
The method for kneading and modifying the red color counterstain pigment provided by the embodiment comprises the following specific steps:
1. kneading
1-1 into a kneader having a capacity of 1L, 80g of B02-L color pigment (clay pigment), 800g of salt (NaCl), 120g of DEG,7g of TSP obtained in Synthesis example 1 were charged, and the mixture was ground for 13 hours at a temperature of 40 ℃. The salt functions to break up the pigment during kneading; DEG has the effect of wetting the pigment and salt to break it up in the wet state, while DEG also has the effect of inhibiting crystal growth.
1-2, washing the kneaded material with water until the conductivity is less than 0.08uS/cm. The water washing process removes the salt and DEG from the kneadate, and TSP is grafted onto the red pigment during kneading.
1-3, and drying at 80 ℃ after centrifugation to obtain the kneaded modified red color sink pigment-B02-LN-2.
2. And (3) pigment dispersion:
into a stainless steel vessel were charged 0.3g of B02-LN-2 pigment obtained by the above kneading process, 7.5g of BYK dispersant product BYK-2001, 14.1g of acrylic resin (solid content NV% = 35%), 11g of pigment blue 15:6, 67.1g of solvent PMA. 150g of zirconium balls with the diameter of 0.3mm are added, and the mixture is placed into an oscillating machine for dispersing for 4 hours, so as to obtain an evaluation composition, namely color paste.
3.1 ml of the composition color paste for evaluation prepared in the step 2 was spin-coated on a glass sheet at 800rpm, the coated glass sheet was placed on a heating plate at 120℃for 1min, and after heating at 230℃in an oven for 30min, chromaticity (x, Y) and luminance (Y) were measured by a spectrocolorimeter, and contrast was measured by a contrast meter. And putting the coated glass sheet into an oven at 230 ℃ for 1h, measuring the chromaticity change delta Eab before and after, and comparing the thermal stability.
TABLE 2 Properties of the kneading modified Red color base pigment prepared in this example 2
| Comparative example 1 | Comparative example 2 | Example 2 | |
| x | 0.1345 | 0.1347 | 0.135 |
| y | 0.1034 | 0.1034 | 0.1034 |
| Brightness (Y) | 11.5 | 11.0 | 12.3 |
| Contrast ratio | 7686 | 7257 | 8643 |
| Chromaticity change DeltaEab (230 ℃ C. 1 h) | 3.4 | 0.55 | 0.5 |
FIG. 1 shows TEM photographs of the kneaded red color sink pigments B02-L prepared in comparative example 2. FIG. 3 shows a TEM photograph of the modified red color sink pigment B02-LN-2 after kneading prepared in example 2.
Fig. 4 shows a particle size diagram of the color paste prepared in comparative example 1. Fig. 5 shows a particle size diagram of the color paste prepared in comparative example 2. Fig. 7 shows a particle size diagram of the color paste prepared in example 2.
As can be seen from the TEM photographs of FIGS. 1 and 3, the particle size (about 100 nm) of comparative example 2 (FIG. 1) is much larger than that (about 50 nm) of example 2 (FIG. 3), indicating that the particle size of the color sink pigment B02-LN is greatly reduced after the TSP is added and kneaded; as can be seen from the graphs of particle sizes of FIGS. 4, 5 and 7, under the same grinding and dispersing conditions, the D50 of example 2 is 53.70nm, which is smaller than the particle size (63.51 nm) of comparative example 1 and is far smaller than the particle size (75.30 nm) of comparative example 2, which shows that the addition of the color sink pigment B02-LN after TSP kneading has an obvious effect on the reduction of the particle size of the blue color paste, and further shows that the brightness and contrast of the final film layer are greatly improved.
Although the present invention has been described to a certain extent, it is apparent that appropriate changes may be made in the individual conditions without departing from the spirit and scope of the invention. It is to be understood that the invention is not to be limited to the described embodiments, but is to be given the full breadth of the claims, including equivalents of each of the elements described.
Claims (18)
1. A modified red color sink pigment for photoresist, characterized in that the modified red color sink pigment comprises a red color sink pigment and tristyrylphenol polyoxyethylene ether;
the red color counterstain is B02-L red color counterstain;
the B02-L red color counterstain is prepared by the following method: dissolving Acid red 52 dye in methanol, and dripping Al 2 (SO 4 ) 3 .18H 2 And (3) reacting the O solution, filtering and drying to obtain a precipitate substance which is the B02-L red pigment.
2. The method for producing a modified red color sink pigment according to claim 1, wherein the production method is a kneading modification treatment method.
3. The method for preparing the modified red color sink pigment according to claim 2, wherein the preparation method comprises the following steps:
(1) Adding a red pigment, naCl, DEG and tristyrylphenol polyoxyethylene ether into a kneader, and heating and grinding;
(2) Washing the product obtained in the step (1);
(3) And (5) centrifugally drying to obtain the modified red color sinking pigment.
4. The preparation method of claim 3, wherein in the step (1), the weight ratio of the raw materials is 1 part of red color sedimentation raw material, 7-15 parts of NaCl, 1.5-3 parts of DEG and 0.05-0.1 part of tristyrylphenol polyoxyethylene ether.
5. The preparation method according to claim 4, wherein in the step (1), 1 part of red color sedimentation raw material, 10-12.5 parts of NaCl, 2-3 parts of DEG and 0.075-0.1 part of tristyrylphenol polyoxyethylene ether.
6. The method according to claim 3, wherein in the step (1), the heating temperature is 30 to 60 ℃; and/or
The grinding time is 8-14 hours.
7. The method of claim 6, wherein in step (1), the heating temperature is 40 ℃; and/or
The grinding time is 10-12 hours.
8. A process according to claim 3, wherein in step (2), the product obtained in step (1) is washed with water to a conductivity of less than 0.1us/cm.
9. The method according to claim 8, wherein in step (2), the product obtained in step (1) is washed with water to a conductivity of less than 0.08us/cm.
10. The method according to claim 3, wherein in the step (3), the drying temperature is 60 to 100 ℃.
11. The method according to claim 10, wherein in the step (3), the drying temperature is 70 to 90 ℃.
12. The method according to claim 11, wherein in the step (3), the drying temperature is 80 ℃.
13. A photoresist composition comprising a resin, a dispersant, a solvent, a blue pigment, a modified red color sink pigment according to claim 1 or a modified red color sink pigment prepared according to the method of any one of claims 2 to 12.
14. The photoresist composition according to claim 13, where the blue pigment is pigment blue 15:6.
15. The photoresist composition according to claim 13, wherein the photoresist composition comprises, by mass, 10-20 parts of resin, 5-10 parts of dispersant, 65-70 parts of solvent, 10-15 parts of blue pigment, and 0.1-0.5 part of modified red pigment.
16. The photoresist composition according to claim 15, wherein the photoresist composition comprises, by mass, 14-15 parts of resin, 7-8 parts of dispersant, 67-68 parts of solvent, 10-13 parts of blue pigment, and 0.3-0.5 part of modified red pigment.
17. The photoresist composition according to claim 13, further comprising a photocurable resin, a photoinitiator, and an additive.
18. A color filter comprising a substrate and a photoresist composition of any one of claims 13 to 17 coated on the substrate and cured.
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| CN107501990A (en) * | 2017-08-22 | 2017-12-22 | 南通市争妍新材料科技有限公司 | A kind of preparation method of high transparency, easily scattered quinacridone pigment |
| CN109212900A (en) * | 2018-09-11 | 2019-01-15 | 深圳市华星光电技术有限公司 | Photoetching compositions and colored filter |
| CN110643201A (en) * | 2019-10-15 | 2020-01-03 | 河北捷虹颜料化工有限公司 | Preparation method of blue organic pigment for liquid crystal color filter material |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107501990A (en) * | 2017-08-22 | 2017-12-22 | 南通市争妍新材料科技有限公司 | A kind of preparation method of high transparency, easily scattered quinacridone pigment |
| CN109212900A (en) * | 2018-09-11 | 2019-01-15 | 深圳市华星光电技术有限公司 | Photoetching compositions and colored filter |
| CN110643201A (en) * | 2019-10-15 | 2020-01-03 | 河北捷虹颜料化工有限公司 | Preparation method of blue organic pigment for liquid crystal color filter material |
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