CN113881244A - Green pigment synergist for color photoresist, and preparation method and application thereof - Google Patents
Green pigment synergist for color photoresist, and preparation method and application thereof Download PDFInfo
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- CN113881244A CN113881244A CN202010636512.2A CN202010636512A CN113881244A CN 113881244 A CN113881244 A CN 113881244A CN 202010636512 A CN202010636512 A CN 202010636512A CN 113881244 A CN113881244 A CN 113881244A
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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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/42—Ionic groups, e.g. free acid
- C09B68/425—Anionic groups
- C09B68/4253—Sulfonic acid groups
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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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
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- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Optical Filters (AREA)
Abstract
The invention provides a green pigment synergist for a photoresist, which is obtained by sulfonating a green pigment and modifying the green pigment by aluminum ions. Compared with the glass substrate without the pigment green 58 synergist, the performance test of the glass substrate added with the pigment green 58 synergist obviously improves the contrast and effectively improves the dispersion stability of the pigment.
Description
Technical Field
The invention belongs to the field of liquid crystal display materials, and particularly relates to a green pigment synergist for a color photoresist, and a preparation method and application thereof.
Background
Photolithography is a common process in the LCD, LED and OLED industries, and photoresist is a necessary material for photolithography, and can undergo cross-linking curing or degradation reaction under the irradiation of light beams. Since the photoresist has the characteristic of being not eroded by the etching solution after the photo-crosslinking curing reaction, it can be used as a direct material in the patterning etching process of the display panel, such as a black matrix on the CF substrate side, a color filter layer RGB color resist, an organic cover layer (OC) and a spacer (PS), and further such as an organic insulating planarization layer (PFA) on the TFT array substrate side
Organic pigments are widely used in the fields of inks, paints, plastics coloring, etc., and in recent years, in the fields of color filters, inks for inkjet, etc., and therefore, organic pigments are more strictly required to have properties such as high transparency, high contrast, good dispersibility, etc.
In order to improve color reproducibility and brightness, it is generally desirable that a colored layer formed of colored patterns of three primary colors of red, green, and blue in a color filter have high density and good light transmittance. However, a coloring composition containing an organic pigment at a high concentration must be used for a colored layer at a high concentration, and when the content of the organic pigment is increased, the content of other components of the coloring composition needs to be relatively reduced, which leads to problems that the dispersion stability of the organic pigment is not good and the coloring composition cannot be stably stored, and on the contrary, the light transmittance of the colored layer is decreased. Therefore, the dispersion stability of organic pigments is the first improvement to increase the light transmittance.
The pigment green 58 is a polyhalogenated zinc phthalocyanine pigment which has excellent coloring power and can further realize high luminance when used as a pixel portion of a color filter.
Wherein the CAS number of pigment green 58 is: 1143572-73-9. The structural formula is shown as the following formula 1:
wherein X independently represents a hydrogen atom, a chlorine atom or a bromine atom, and 10 to 15 of all X are bromine atoms and 1 to 6 are chlorine atoms. The actual pigment green 58 is a mixture of mostly fully substituted bromochlorine products and also partially incompletely substituted products which still contain small amounts of H.
As a characteristic required of such a liquid crystal display, high definition of a screen can be cited. In order to achieve higher definition, the pixel density needs to be increased, but the aperture ratio of the screen is reduced, which causes a problem of reduction in luminance. The decrease in luminance can be compensated for by an increase in the amount of backlight light, but a new problem arises in that the power consumption increases. Therefore, improvement of color filters has been carried out by using pigments having high transmittance for backlight light, such as pigment green 58. However, the single use pigment green 58 has many problems and its performance is not good.
Conventionally, there have been known methods of improving the dispersion stability of an organic pigment, such as modifying a pigment and using a pigment dispersion auxiliary (also called a synergist). At present, the pigment green 58 has the problems of poor dispersibility and unstable polymerization, and has urgent need for a dispersion auxiliary agent.
Disclosure of Invention
Therefore, the present invention aims to overcome the defects in the prior art and provide a green pigment synergist for a color photoresist, a preparation method and an application thereof.
The first aspect of the present invention provides a green pigment synergist for a color photoresist, which is obtained by sulfonating a green pigment and modifying the green pigment with aluminum ions.
The green pigment synergist according to the first aspect of the present invention, wherein the green pigment is pigment green 58;
preferably, the green pigment synergist has a chemical formula shown in formula 2:
wherein X independently represents a chlorine atom or a bromine atom, 10 to 15 of all X are bromine atoms, and 1 to 6 are chlorine atoms.
A second aspect of the present invention provides a method for preparing the green pigment synergist described in the first aspect, comprising the steps of:
(1) carrying out sulfonation reaction on the green pigment by using concentrated sulfuric acid and a sulfonation reagent;
(2) adding metal aluminum salt into the product obtained in the step (1), and heating for reaction;
(3) and (3) washing the product obtained in the step (2), and drying to obtain the green pigment synergist.
The production method according to the second aspect of the present invention, wherein, in the step (1), the sulfonating agent is selected from one or more of: chlorosulfonic acid, sulfur trioxide, sulfamic acid, sulfites;
preferably, the sulfonating agent is chlorosulfonic acid;
more preferably, the mass ratio of the sulfonation reagent to the green pigment is 1-1.5: 1, preferably 1.2: 1.
The preparation method according to the second aspect of the present invention, wherein, in the step (1), the heating temperature of the sulfonation reaction is 100 to 260 ℃, preferably 100 to 180 ℃, and most preferably 130 ℃; and/or
The sulfonation reaction time is 2-12 hours, preferably 6-10 hours, and most preferably 8 hours.
The production method according to the second aspect of the present invention, wherein, in the step (2), the metal aluminum salt is selected from one or more of: aluminum sulfate, aluminum chloride, aluminum nitrate;
preferably, the metal aluminum salt is aluminum chloride.
The preparation method according to the second aspect of the present invention, wherein, in the step (2), the heating temperature of the heating reaction is 120 to 280 ℃, preferably 150 to 200 ℃, and most preferably 180 ℃; and/or
The heating reaction time is 6-20 hours, preferably 8-12 hours, and most preferably 10 hours.
The production method according to the second aspect of the present invention, wherein, in the step (3), the washing method is selected from one or more of: acid washing, water washing and acetone washing.
A third aspect of the present invention provides a color photoresist composition comprising a resin, a dispersant, a solvent, a green pigment synergist according to the first aspect or a green pigment synergist prepared according to the method of the second aspect;
preferably, in the color photoresist composition, the mass parts of the raw materials comprise 10-20 parts of resin, 5-15 parts of dispersant, 65-70 parts of solvent, 10-15 parts of green pigment and 0.1-0.5 part of green pigment synergist;
more preferably, the mass parts of the raw materials are 14-15 parts of resin, 8-10 parts of dispersant, 60-65 parts of solvent, 10-15 parts of green pigment and 0.2-0.4 part of green pigment synergist;
further preferably, the color photoresist composition further comprises a photoinitiator, and the mass fraction of the photoinitiator in the color photoresist composition is preferably 0.2-0.5%.
A fourth aspect of the present invention provides an optical filter comprising a substrate and the photoresist composition of the third aspect coated on the substrate and cured.
The invention aims to provide a synergist suitable for combination of pigment green 58.
The invention provides a pigment synergist, which has a chemical formula as shown in formula 2:
the synthesis process method comprises the following steps: 1mol of pigment green 58 is added into a reaction vessel, and then 1.2mol of sulfonation reagent such as concentrated sulfuric acid (including fuming sulfuric acid), chlorosulfonic acid, sulfur trioxide, sulfamic acid and sulfite are used for sulfonation, the reaction temperature is 100-260 ℃, and the reaction lasts for 2-12 hours; then adding metal aluminum salt such as aluminum sulfate, aluminum chloride, aluminum nitrate and the like into the reaction kettle, reacting at the reaction temperature of 120-280 ℃ for 6-20 hours, cooling, carrying out acid washing, water washing and acetone washing, and drying to obtain the final product, namely the pigment green 58 synergist, wherein the reaction yield is over 80%.
Compared with the prior art, the green pigment synergist of the invention can have the following beneficial effects:
compared with the glass substrate without the pigment green 58 synergist, the performance test of the glass substrate added with the pigment green 58 synergist obviously improves the contrast and effectively improves the dispersion stability of the pigment.
Drawings
Embodiments of the invention are described in detail below with reference to the attached drawing figures, wherein:
FIG. 1 shows the nuclear magnetic hydrogen spectrum of the green pigment synergist prepared in example 1.
Detailed Description
The invention is further illustrated by the following specific examples, which, however, are to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.
This section generally describes the materials used in the testing of the present invention, as well as the testing methods. Although many materials and methods of operation are known in the art for the purpose of carrying out the invention, the invention is nevertheless described herein in as detail as possible. It will be apparent to those skilled in the art that the materials and methods of operation used in the present invention are well within the skill of the art, provided that they are not specifically illustrated.
The reagents and instrumentation used in the following examples are as follows:
reagent:
pigment green 58 (japan DIC), chlorosulfonic acid, aluminum chloride, propylene glycol methyl ether acetate, zirconium spheres, benzyl methacrylate, methacrylic acid, purchased from national pharmaceutical agents;
BYK-21116 from Pico.
The instrument comprises the following steps:
nuclear magnetic resonance apparatus available from Bruker, switzerland, model Avance Neo 600;
shaker, available from Lau, germany, model DAS 200;
a spin coater, available from Beijing, Tongde Chuangye science and technology Limited, model KW-4B;
a baking machine, available from Beijing Fine measurement electronics technologies, Inc., model number LH3-HP 6;
a drying oven, available from Shanghai North Engineers, model 101-1 SB;
spectrocolorimeter, available from KONICA, model CM-5;
contrast instrument, available from Japanese Kebang Motor, model CT1STB 1.
Example 1
This example serves to illustrate the process for the synthesis of the pigment synergist of the present invention:
1 part of pigment green 58 is added into a reaction vessel, and 0.1 part of 98% concentrated sulfuric acid is added for mixing, wherein the concentrated sulfuric acid plays a part in dechlorination and debromination and also plays a role in promoting sulfonation. Then, sulfonating by using 1.2 parts of sulfonating agent such as chlorosulfonic acid, sulfur trioxide, sulfamic acid, sulfite and the like, wherein the reaction temperature is 180-260 ℃, and reacting for 2-12 hours; then adding 1 part of metal aluminum salt such as aluminum sulfate, aluminum chloride, aluminum nitrate and the like into the reaction kettle, reacting at the reaction temperature of 120-280 ℃ for 6-20 hours, cooling, carrying out acid washing, water washing and acetone washing, and drying to obtain the final product, namely the pigment green 58 synergist, wherein the reaction yield is over 60 percent. Wherein the parts are parts by mass.
In one embodiment, 1 part of pigment green 58 is added into a reaction vessel, 0.1 part of 98% concentrated sulfuric acid is added, and then sulfonation is carried out by using 1.2 parts of sulfonating agent chlorosulfonic acid, wherein the reaction temperature is 120 ℃ and the reaction time is 8 hours; then adding 1 part of metal aluminum salt aluminum chloride into a reaction kettle, reacting for 6 hours at the reaction temperature of 180 ℃, cooling, carrying out acid washing, water washing and acetone washing, and then drying to obtain the final product, namely the pigment green 58 synergist, wherein the reaction yield is 73.6%. Wherein the parts are parts by mass.
Product analysis and detection:
the nuclear magnetic hydrogen spectrum is shown in figure 1. In the nuclear magnetic spectrum, the peak of the DMSO deuteration reagent is δ of 2.495ppm, the peak of the DMSO deuteration reagent is δ of 3.291min, and since all hydrogen atoms on the benzene ring are substituted by halogen atoms and sulfonic acid groups, no peak is substantially present between δ of 6 and 8, which is determined to be consistent with the actual product.
Test example 1
A comparison was made between mill base compositions without the addition of the synergist synthesized in example 1 and with the addition of the synergist synthesized in example 1.
TABLE 1 application evaluation Green color paste composition
The preparation method of the resin comprises the following steps: separately, 10.00g of benzyl methacrylate was weighed into a beaker and stirred, and then 4.29g of methacrylic acid was slowly added with stirring and mixed for 30 minutes to prepare a mixture.
To a stainless steel container were added 0.3g of the synergist obtained in example 1, 10g of BYK-LPN-21116 dispersant, 14.29g of resin (70: 30 molar ratio of benzyl methacrylate to methacrylic acid, 15,000 molecular weight, 35% solid content), 13g of pigment green 58a110, and 64.41g of propylene glycol methyl ether acetate. 150g of 0.3mm zirconium balls were additionally added, and the mixture was dispersed in a shaker for 4 hours to obtain the composition. The composition for evaluation was spin-coated on a glass plate at a spin-coating rate of 1000r/min in an amount of 1ml, and dried at 120 ℃ for 1 minute. The glass substrate was then heated at a temperature of 230 ℃ for 30 hours, and the chromaticity and luminance (Y) were measured together, and the contrast was measured in a contrast meter.
In the same manner, a comparative glass substrate was prepared as described above without the addition of the pigment green 58 synergist composition.
As a result of analysis, the performance of the glass substrate added with the pigment green 58 synergist is detected, and other indexes are consistent, but the contrast ratio detected by a contrast meter is between 14000-15000, and the contrast ratio detected without the synergist is only about 8000-9000.
TABLE 2 Green pigment Properties of this test example 1 and comparative example 1
| Test example 1 | Comparative example 1 | |
| Chroma (x y) | (0.248,0.500) | (0.248,0.500) |
| Luminance (Y) | 60 | 52 |
| Contrast ratio | 12408 | 8573 |
Although the present invention has been described to a certain extent, it is apparent that appropriate changes in the respective conditions may be made without departing from the spirit and scope of the present invention. It is to be understood that the invention is not limited to the described embodiments, but is to be accorded the scope consistent with the claims, including equivalents of each element described.
Claims (10)
1. A green pigment synergist for a color photoresist, characterized in that the green pigment synergist is obtained by sulfonating a green pigment and modifying the green pigment with aluminum ions.
2. A green pigment synergist according to claim 1, wherein said green pigment is pigment green 58;
preferably, the green pigment synergist has the formula:
wherein X independently represents a chlorine atom or a bromine atom, 10 to 15 of all X are bromine atoms, and 1 to 6 are chlorine atoms.
3. A process for the preparation of a green pigment synergist according to claim 1 or 2, characterized in that said process comprises the steps of:
(1) carrying out sulfonation reaction on the green pigment by using concentrated sulfuric acid and a sulfonation reagent;
(2) adding metal aluminum salt into the product obtained in the step (1), and heating for reaction;
(3) and (3) washing the product obtained in the step (2), and drying to obtain the green pigment synergist.
4. The process of claim 3, wherein in step (1), the sulfonating agent is selected from one or more of the following: chlorosulfonic acid, sulfur trioxide, sulfamic acid, sulfites;
preferably, the sulfonating agent is chlorosulfonic acid;
more preferably, the mass ratio of the sulfonation reagent to the green pigment is 1-1.5: 1, preferably 1.2: 1.
5. The method according to claim 3 or 4, wherein in the step (1), the sulfonation reaction is heated at a temperature of 100 to 260 ℃, preferably 100 to 180 ℃, and most preferably 130 ℃; and/or
The sulfonation reaction time is 2-12 hours, preferably 6-10 hours, and most preferably 8 hours.
6. The process according to any one of claims 3 to 5, wherein in step (2), the metal aluminium salt is selected from one or more of: aluminum sulfate, aluminum chloride, aluminum nitrate;
preferably, the metal aluminum salt is aluminum chloride.
7. The method according to any one of claims 3 to 6, wherein in the step (2), the heating reaction heating temperature is 120-280 ℃, preferably 150-200 ℃, and most preferably 180 ℃; and/or
The heating reaction time is 6-20 hours, preferably 8-12 hours, and most preferably 10 hours.
8. The process according to any one of claims 3 to 7, wherein in step (3), the washing method is selected from one or more of: acid washing, water washing and acetone washing.
9. A color photoresist composition comprising a resin, a dispersant, a solvent, a green pigment synergist according to claim 1 or 2 or a green pigment synergist prepared according to any one of claims 3 to 8;
preferably, in the color photoresist composition, the mass parts of the raw materials comprise 10-20 parts of resin, 5-15 parts of dispersant, 65-70 parts of solvent, 10-15 parts of green pigment and 0.1-0.5 part of green pigment synergist;
more preferably, the mass parts of the raw materials are 14-15 parts of resin, 8-10 parts of dispersant, 60-65 parts of solvent, 10-15 parts of green pigment and 0.2-0.4 part of green pigment synergist;
further preferably, the color photoresist composition further comprises a photoinitiator, and the mass fraction of the photoinitiator in the color photoresist composition is preferably 0.2-0.5%.
10. An optical filter comprising a substrate and the color photoresist composition of claim 9 coated on the substrate and cured.
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| CN202010636512.2A CN113881244B (en) | 2020-07-03 | 2020-07-03 | Green pigment synergist for color photoresist, preparation method and application thereof |
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| CN202010636512.2A CN113881244B (en) | 2020-07-03 | 2020-07-03 | Green pigment synergist for color photoresist, preparation method and application thereof |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5922123A (en) * | 1997-12-17 | 1999-07-13 | Bayer Corporation | Method for conditioning organic pigments |
| CN103513513A (en) * | 2012-06-20 | 2014-01-15 | 阪田油墨股份有限公司 | A green colored composition for a color filter |
| CN107043555A (en) * | 2016-02-05 | 2017-08-15 | 阪田油墨股份有限公司 | Colored filter viridine green dispersion |
| CN107586469A (en) * | 2016-07-07 | 2018-01-16 | 住友化学株式会社 | Color compositions, coloured composition and cured composition for color |
-
2020
- 2020-07-03 CN CN202010636512.2A patent/CN113881244B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5922123A (en) * | 1997-12-17 | 1999-07-13 | Bayer Corporation | Method for conditioning organic pigments |
| CN103513513A (en) * | 2012-06-20 | 2014-01-15 | 阪田油墨股份有限公司 | A green colored composition for a color filter |
| CN107043555A (en) * | 2016-02-05 | 2017-08-15 | 阪田油墨股份有限公司 | Colored filter viridine green dispersion |
| CN107586469A (en) * | 2016-07-07 | 2018-01-16 | 住友化学株式会社 | Color compositions, coloured composition and cured composition for color |
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