CN113980488A - Yellow dye, preparation method thereof, yellow color paste containing yellow dye, color photoresist and optical filter - Google Patents

Yellow dye, preparation method thereof, yellow color paste containing yellow dye, color photoresist and optical filter Download PDF

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CN113980488A
CN113980488A CN202111365355.7A CN202111365355A CN113980488A CN 113980488 A CN113980488 A CN 113980488A CN 202111365355 A CN202111365355 A CN 202111365355A CN 113980488 A CN113980488 A CN 113980488A
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yellow
dye
yellow dye
acid yellow
chloride
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CN113980488B (en
Inventor
豆帆
盛振宏
高政纲
李喆雨
滕福爱
崔亨利
颜俊雄
朱洪维
洪海哲
刘海燕
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Shandong Kairuier Photoelectric Technology Co ltd
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Shandong Kairuier Photoelectric Technology Co ltd
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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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
    • C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes
    • 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
    • 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
    • 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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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optics & Photonics (AREA)
  • Optical Filters (AREA)
  • Paints Or Removers (AREA)

Abstract

The invention discloses a yellow dye, which comprises at least one compound shown in a chemical formula I. The invention also provides a preparation method of the yellow dye, which comprises the following steps: (1) dissolving the acid yellow, and adjusting the pH value of the solution to 1-4; (2) adding benzyl vinyl trimethyl ammonium chloride or acryloyl propyl trimethyl ammonium chloride, and heating for reaction; (3) filtering to obtain a reactant, and drying in vacuum to obtain the yellow dye. The invention also provides yellow color paste, a color photoresist and an optical filter containing the yellow dye. The invention can prepare the dye with excellent tinting strength and heat-resistant and light-resistant performance, and simultaneously improve the brightness and contrast of the optical filter.
Figure DDA0003359720400000011

Description

Yellow dye, preparation method thereof, yellow color paste containing yellow dye, color photoresist and optical filter
Technical Field
The invention relates to the technical field of liquid crystal display, in particular to a yellow dye, a preparation method thereof, yellow color paste containing the yellow dye, a color photoresist and an optical filter.
Background
Liquid Crystal Displays (LCDs) have rapidly grown at the end of the 20 th century and become the leading technology in the display field today due to their advantages of low power consumption, low radiation, high image quality, lightness and portability, and have been developed toward high resolution and large screens. 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 outer coating and an ITO conductive film, wherein the color photoresist layer of the color filter is composed of three-color photoresists of red, green and blue (RGB). To achieve good color reproducibility, color filters must have high color purity and high transmittance, and filters must have high contrast, low reflectance, 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, light-cured resin, a photoinitiator, a solvent and the like. The quality of the color filter mainly depends on the performance of the light resistor and the coating process thereof, wherein the light resistor pigment is one of the main influencing factors as a coloring agent, and in order to fully exert the coloring power and the vividness thereof and obtain good spectral characteristics, pigment particles are required to be dispersed in the pigment light resistor in a fine, uniform and stable state as much as possible, and the high-grade organic pigment variety is mainly selected to obtain the pigment dispersion-color paste with fine and stable particle size through the efficient dispersion treatment process. The dispersion state and particle size of the pigment determine whether the final coating has high transmittance and high contrast.
The color filter can be colored by dye or pigment, the dye has the advantages of bright color, strong color reproduction capability and low cost, and the defects of poor heat resistance and light fastness, and compared with dye dyeing, the pigment dyeing has excellent moisture resistance, light fastness and heat resistance stability. Combining the advantages of both methods, it has become a trend to add dyes in the preparation of pigment process pastes in order to obtain higher contrast and brightness. However, the organic pigments in the prior art still have the technical problems of low transmittance and contrast of the coating, poor heat resistance and poor light resistance.
Disclosure of Invention
The invention aims to solve the technical problems that the particle size of pigment particles in the prior art cannot meet the requirement, the coloring power of a dye is poor, the transmittance and contrast of a coating are low, and the heat resistance and light resistance are poor. The invention provides a yellow dye and a preparation method thereof, and a yellow color paste, a color photoresist and an optical filter containing the yellow dye, wherein the yellow dye can be used for preparing the dye with excellent tinting strength and heat and light resistance, and simultaneously improving the brightness and contrast of the optical filter.
To solve the above technical problems, embodiments of the present invention disclose a yellow dye comprising at least one compound represented by formula I:
Figure BDA0003359720380000021
wherein the content of the first and second substances,
Figure BDA0003359720380000031
represents acid yellow;
p1, P2 and P3 are one or more of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, isohexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, heptyl, isoheptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl;
p4 includes the structure of formula II, III:
Figure BDA0003359720380000032
according to another embodiment of the present invention, there is disclosed a yellow dye, wherein the acid yellow is acid yellow 23 having a formula of C16H9N4Na3O9S2Has a structure shown in a chemical formula II:
Figure BDA0003359720380000033
according to another embodiment of the present invention, there is disclosed a yellow dye comprising one or both of the following formulas:
Figure BDA0003359720380000041
according to another embodiment of the present invention, there is disclosed a yellow dye represented by formula I-1, which is prepared by reacting acid yellow 23 with benzylvinyl trimethyl ammonium chloride; the yellow dye of formula I-2 is prepared by reacting acid yellow 23 with acryloylpropyltrimethylammonium chloride.
The embodiment of the invention also discloses a preparation method of the yellow dye, which comprises the following steps:
(1) dissolving the acid yellow, and adjusting the pH value of the solution to 1-4;
(2) adding benzyl vinyl trimethyl ammonium chloride or acryloyl propyl trimethyl ammonium chloride, and heating for reaction;
(3) filtering to obtain a reactant, and drying in vacuum to obtain the yellow dye.
According to another embodiment of the present invention, the embodiment of the present invention discloses a method for preparing a yellow dye, wherein the molar ratio of acid yellow 23 to benzylvinyltrimethylammonium chloride is 1: 1.5-2.5;
the molar ratio of acid yellow 23 to the acryloylpropyltrimethylammonium chloride is 1: 1.5-2.5;
in the step (2), the reaction temperature is controlled to be 20-100 ℃.
According to another embodiment of the present invention, the embodiment of the present invention discloses a method for preparing a yellow dye, wherein the molar ratio of acid yellow 23 to benzylvinyl trimethyl ammonium chloride is 2;
the molar ratio of the acid yellow 23 to the acryloyl propyl trimethyl ammonium chloride is 2;
in the step (1), adjusting the pH value of the solution to 2.5;
in the step (2), the reaction temperature is controlled to be 30-60 ℃.
The embodiment of the invention also discloses yellow color paste, which comprises the following components in percentage by weight:
Figure BDA0003359720380000051
the embodiment of the invention also discloses a color photoresist which comprises the yellow color paste.
The embodiment of the invention also discloses an optical filter which comprises the color photoresist.
Compared with the prior art, the invention has the following technical effects:
(1) the dye subjected to modification treatment has the advantage of good tinting strength and has the characteristics of heat resistance and light resistance;
(2) according to the invention, the modified dye is added on the basis of the original color paste ingredients, and the modified yellow dye prepared by the method is added on the basis of the original yellow pigment, so that the thermal stability and the light stability of the yellow dye are ensured, the brightness and the contrast of a final product are greatly improved, the raw materials are low in price, the preparation process is simple, and the repeatability is good.
(3) The invention is used together with yellow pigment for preparing color photoresist, is used for improving the brightness of color paste, has good dispersibility, high transparency and high contrast.
Drawings
FIG. 1 shows a MALDI-TOF mass spectrum of the yellow dye S1 of example 1 of the present invention.
Detailed Description
The following description of the embodiments of the present invention is provided for illustrative purposes, and other advantages and effects of the present invention will become apparent to those skilled in the art from the present disclosure. While the invention will be described in conjunction with the preferred embodiments, it is not intended that features of the invention be limited to these embodiments. On the contrary, the invention is described in connection with the embodiments for the purpose of covering alternatives or modifications that may be extended based on the claims of the present invention. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. The invention may be practiced without these particulars. Moreover, some of the specific details have been left out of the description in order to avoid obscuring or obscuring the focus of the present invention. It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The raw materials and the types used in the invention are as follows:
"acid yellow 23" means: C.I.acid Yellow 23, molecular formula C16H9N4Na3O9S2Molecular weight 534.36, CAS number 1934-21-0, formula shown below:
Figure BDA0003359720380000061
"benzylvinyltrimethylammonium chloride": 4-vinylbenzyltrimethylammonium chloride of formula C12H18ClN, molecular weight 211.73, CAS number 26616-35-3, formula shown below:
Figure BDA0003359720380000062
"Acrylopropyltrimethylammonium chloride": (3-acrylamidopropyl) trimethylammonium chloride of formula C9H19ClN2O, molecular weight 206.71, CAS number 45021-77-0, formula shown below:
Figure BDA0003359720380000063
by "solvent" is meant: PMA, propylene glycol methyl ether acetate, CAS number 108-65-6;
"yellow pigment" means: c.i. pigment yellow 138, manufactured by WISECHEM corporation,
resin: benzyl methacrylate/methacrylic acid 70/30, molecular weight 12000, acid number 115, solids content 28%;
dispersant BYK-21116 (40% solids) was a dispersant from Pico Chemicals.
The synthesis reaction equation involved in the invention is as follows:
Figure BDA0003359720380000071
first, Synthesis example of yellow dye
Example 1
The synthesis reaction equation for this example is as follows:
Figure BDA0003359720380000072
reaction of acid yellow 23 with benzylvinyltrimethylammonium chloride:
1L of water was put into a 2L three-necked flask, and 106.87g of yellow 23 dye was added thereto and dissolved by stirring. Adjusting pH to 2.5 with 20% sulfuric acid, controlling temperature to 40 deg.C, adding 86.56g benzyl vinyl trimethyl ammonium chloride, and stirring for 1 hr; the reaction was filtered to obtain a reaction product. The reaction cake was washed with water and dried in a vacuum oven at 40 ℃ for 12h to give 159.83g of yellow dye S1 in 95.03% yield, MALDI-TOF mass spectrum 840.24 (theoretical value 840.94).
Figure BDA0003359720380000081
Example 2
The synthesis reaction equation for this example is as follows:
Figure BDA0003359720380000082
1L of water was put into a 2L three-necked flask, and 106.87g of yellow 23 dye was added thereto and dissolved by stirring. Adjusting pH to 2.5 with 20% sulfuric acid, controlling temperature to 50 deg.C, adding 84.75g of acryloylpropyltrimethylammonium chloride, and stirring for 1 hr; the reaction was filtered to obtain a reaction product. The reaction cake was washed with water and dried in a vacuum oven at 40 ℃ for 12h to give yellow dye S2158.92g, 95.63% yield.
Figure BDA0003359720380000083
Example 3
The synthesis reaction equation of this example is the same as that of example 2;
1L of water was put into a 2L three-necked flask, and 106.87g of yellow 23 dye was added thereto and dissolved by stirring. Adjusting pH to 2.5 with 20% sulfuric acid, controlling temperature to 50 deg.C, adding 103.35g of acryloylpropyltrimethylammonium chloride, and stirring for 1 hr; the reaction was filtered to obtain a reaction product. The reaction cake was washed with water and dried in a vacuum oven at 40 ℃ for 12h to give S2162.43g yellow dye in 97.74% yield.
Comparative example 1
1L of water was put into a 2L three-necked flask, and 106.87g of yellow 23 dye was added thereto and dissolved by stirring. Hydrochloric acid was added dropwise to adjust the pH to 2.5, and stirring was continued for 1 hour. The system after the reaction is separated out in an ice-water bath and filtered. The filter cake was washed with cold water and dried in a vacuum oven at 40 ℃ for 12h to give protonated yellow dye D-297.57 g with a yield of 91.29%.
Application example of yellow color paste
Application example 1
The ingredients are as follows:
Figure BDA0003359720380000091
adding the weighed ingredients into a glass container, adding 120g of 0.3mm zirconium balls, placing into a shaking machine for shaking and dispersing for 6h to obtain a dispersion composition, spin-coating the dispersion composition on glass, placing a coated glass sheet on a 120 ℃ heating plate for heating for 90s, heating for 30min at 230 ℃ in an oven, measuring the chromaticity (x, Y) and the brightness (Y), measuring the contrast by using a contrast instrument, and measuring the brightness (Y) heated for 60min at 230 ℃.
Application example 2
The ingredients are as follows:
Figure BDA0003359720380000092
Figure BDA0003359720380000101
adding the weighed ingredients into a glass container, adding 120g of 0.3mm zirconium balls, placing into a shaking machine for shaking and dispersing for 6h to obtain a dispersion composition, spin-coating the dispersion composition on glass, placing a coated glass sheet on a 120 ℃ heating plate for heating for 90s, heating for 30min at 230 ℃ in an oven, measuring the chromaticity (x, Y) and the brightness (Y), measuring the contrast by using a contrast instrument, and measuring the brightness (Y) heated for 60min at 230 ℃.
Application example 3
The ingredients are as follows:
Figure BDA0003359720380000102
adding the weighed ingredients into a glass container, adding 120g of 0.3mm zirconium balls, placing into a shaking machine for shaking and dispersing for 6h to obtain a dispersion composition, spin-coating the dispersion composition on glass, placing a coated glass sheet on a 120 ℃ heating plate for heating for 90s, heating for 30min at 230 ℃ in an oven, measuring the chromaticity (x, Y) and the brightness (Y), measuring the contrast by using a contrast instrument, and measuring the brightness (Y) heated for 60min at 230 ℃.
Application example 4
The ingredients are as follows:
Figure BDA0003359720380000103
adding the weighed ingredients into a glass container, adding 120g of 0.3mm zirconium balls, placing into a shaking machine for shaking and dispersing for 6h to obtain a dispersion composition, spin-coating the dispersion composition on glass, placing a coated glass sheet on a 120 ℃ heating plate for heating for 90s, heating for 30min at 230 ℃ in an oven, measuring the chromaticity (x, Y) and the brightness (Y), measuring the contrast by using a contrast instrument, and measuring the brightness (Y) heated for 60min at 230 ℃.
Application example 5
The ingredients are as follows:
Figure BDA0003359720380000111
adding the weighed ingredients into a glass container, adding 120g of 0.3mm zirconium balls, placing into a shaking machine for shaking and dispersing for 6h to obtain a dispersion composition, spin-coating the dispersion composition on glass, placing a coated glass sheet on a 120 ℃ heating plate for heating for 90s, heating for 30min at 230 ℃ in an oven, measuring the chromaticity (x, Y) and the brightness (Y), measuring the contrast by using a contrast instrument, and measuring the brightness (Y) heated for 60min at 230 ℃.
Application example 6
The ingredients are as follows:
Figure BDA0003359720380000112
adding the weighed ingredients into a glass container, adding 120g of 0.3mm zirconium balls, placing into a shaking machine for shaking and dispersing for 6h to obtain a dispersion composition, spin-coating the dispersion composition on glass, placing a coated glass sheet on a 120 ℃ heating plate for heating for 90s, heating for 30min at 230 ℃ in an oven, measuring the chromaticity (x, Y) and the brightness (Y), measuring the contrast by using a contrast instrument, and measuring the brightness (Y) heated for 60min at 230 ℃.
Application comparative example 1
The ingredients are as follows:
Figure BDA0003359720380000121
adding the weighed ingredients into a glass container, adding 120g of 0.3mm zirconium balls, placing into a shaking machine for shaking and dispersing for 6h to obtain a dispersion composition, spin-coating the dispersion composition on glass, placing a coated glass sheet on a 120 ℃ heating plate for heating for 90s, heating for 30min at 230 ℃ in an oven, measuring the chromaticity (x, Y) and the brightness (Y), measuring the contrast by using a contrast instrument, and measuring the brightness (Y) heated for 60min at 230 ℃.
Comparative application example 2
The ingredients are as follows:
Figure BDA0003359720380000122
adding the weighed ingredients into a glass container, adding 120g of 0.3mm zirconium balls, placing into a shaking machine for shaking and dispersing for 6h to obtain a dispersion composition, spin-coating the dispersion composition on glass, placing a coated glass sheet on a 120 ℃ heating plate for heating for 90s, heating for 30min at 230 ℃ in an oven, measuring the chromaticity (x, Y) and the brightness (Y), measuring the contrast by using a contrast instrument, and measuring the brightness (Y) heated for 60min at 230 ℃.
The results of the tests and evaluations of application examples 1 to 6 and application comparative examples 1 to 2 are shown in Table 1.
Table 1 comparative test results (y is 0.488)
Figure BDA0003359720380000123
Wherein the content of the first and second substances,
Figure BDA0003359720380000124
in the formula (1), Y is the brightness of 230 ℃ for 30 min;
y' is 230 ℃ and the brightness is 60 min;
x and y are color coordinates of 230 ℃ for 30 min;
x 'y' is the color coordinate at 230 ℃ for 60 min.
As can be seen from Table 1, the yellow paste prepared by the invention has good dispersibility, and has high contrast and high brightness compared with the prior art after being coated on a glass sheet, and can be applied to an optical filter.
As can be seen from table 1 and formula (1), glass sheets coated with mill base prepared with unmodified Y-138 yellow pigment (application comparative example 1) had low contrast and Y values, i.e., poor contrast and brightness, although Δ Eab @ (good thermal stability); the glass sheet coated with the color paste prepared by adding the protonated yellow dye (application comparative example 2) had poor thermal stability (Δ E) although its contrast and brightness were improvedabValue of>3) (ii) a The application examples 1-6 of the invention adopt the yellow color paste added with the modified yellow dye, the contrast and the Y value of the coated glass sheet are obviously improved, and simultaneously, the contrast and the Y value of the coated glass sheet are obviously improved
Figure BDA0003359720380000131
Far less than 3, good thermal stability, good tinting strength, heat resistance and light resistanceIs excellent.
While the invention has been described with reference to certain preferred embodiments thereof, it will be understood by those skilled in the art that the foregoing is a more particular description of the invention than is possible with reference to the specific embodiments, which are not to be construed as limiting the invention. Various changes in form and detail, including simple deductions or substitutions, may be made by those skilled in the art without departing from the spirit and scope of the invention.

Claims (10)

1. A yellow dye comprising at least one compound of formula I:
Figure FDA0003359720370000011
wherein the content of the first and second substances,
Figure FDA0003359720370000012
represents acid yellow;
p1, P2 and P3 are one or more of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, isohexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 2-ethylhexyl, heptyl, isoheptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl;
p4 includes the structure of formula II, III:
Figure FDA0003359720370000013
Figure FDA0003359720370000021
2. such as rightThe yellow dye of claim 1, wherein the acid yellow is acid yellow 23, and the acid yellow 23 has a molecular formula of C16H9N4Na3O9S2The acid yellow has a structure shown in a chemical formula II:
Figure FDA0003359720370000022
3. the yellow dye of claim 2, wherein the yellow dye comprises one or both of the following formulas:
Figure FDA0003359720370000023
4. the yellow dye according to claim 3, wherein the yellow dye of formula I-1 is prepared by reacting the acid yellow 23 with benzylvinyltrimethylammonium chloride; the yellow dye shown in the chemical formula I-2 is prepared by reacting the acid yellow 23 with acryloyl propyl trimethyl ammonium chloride.
5. A process for the preparation of a yellow dye according to claim 3 or 4, comprising the steps of:
(1) dissolving the acid yellow, and adjusting the pH value of the solution to 1-4;
(2) adding benzyl vinyl trimethyl ammonium chloride or acryloyl propyl trimethyl ammonium chloride, and heating for reaction;
(3) filtering to obtain a reactant, and drying in vacuum to obtain the yellow dye.
6. The method of claim 5, wherein the molar ratio of acid yellow 23 to benzylvinyltrimethylammonium chloride is 1: 1.5-2.5;
the molar ratio of the acid yellow 23 to the acryloylpropyltrimethylammonium chloride is 1: 1.5-2.5;
in the step (2), the reaction temperature is controlled to be 20-100 ℃.
7. The method of claim 6, wherein the molar ratio of acid yellow 23 to benzylvinyltrimethylammonium chloride is 2;
the molar ratio of the acid yellow 23 to the acryloylpropyltrimethylammonium chloride is 2;
in the step (1), adjusting the pH value of the solution to 2.5;
in the step (2), the reaction temperature is controlled to be 30-60 ℃.
8. A yellow paste is characterized by comprising:
Figure FDA0003359720370000031
9. a color photoresist comprising the yellow paste according to claim 8.
10. An optical filter comprising the color resist according to claim 9.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104479680A (en) * 2014-12-19 2015-04-01 京东方科技集团股份有限公司 Modified quantum dot, preparation method thereof, coloring agent, photosensitive resin composition, color filter and display device
CN107168012A (en) * 2017-07-11 2017-09-15 深圳市华星光电技术有限公司 A kind of colored photoresist and preparation method thereof
CN110187602A (en) * 2019-05-14 2019-08-30 深圳市华星光电技术有限公司 Colored photoetching compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104479680A (en) * 2014-12-19 2015-04-01 京东方科技集团股份有限公司 Modified quantum dot, preparation method thereof, coloring agent, photosensitive resin composition, color filter and display device
CN107168012A (en) * 2017-07-11 2017-09-15 深圳市华星光电技术有限公司 A kind of colored photoresist and preparation method thereof
CN110187602A (en) * 2019-05-14 2019-08-30 深圳市华星光电技术有限公司 Colored photoetching compositions

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