CN114755890A - Low-temperature negative black photoresist composition and black matrix thereof - Google Patents
Low-temperature negative black photoresist composition and black matrix thereof Download PDFInfo
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- CN114755890A CN114755890A CN202210052881.6A CN202210052881A CN114755890A CN 114755890 A CN114755890 A CN 114755890A CN 202210052881 A CN202210052881 A CN 202210052881A CN 114755890 A CN114755890 A CN 114755890A
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- black
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- 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
- G02F1/133512—Light shielding layers, e.g. black matrix
-
- 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
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention relates to a low-temperature negative black photoresist composition and a black matrix thereof, which comprise an organic solvent and solute dissolved in the organic solvent, wherein the solute accounts for 15-60% of the total weight of the composition, and comprises the following components: the light-cured resin comprises light-cured resin containing double bonds and hydroxyl groups, alkali-soluble acrylate photopolymerization monomers, a photoinitiator, a coloring agent and a low-temperature blocked isocyanate crosslinking agent. The photoresist composition disclosed by the invention is initiated to polymerize by a photoinitiator through adding the light-cured resin containing double bonds and hydroxyl groups and the alkali-soluble acrylate photopolymerization monomer, so that the adhesiveness of the photoresist is improved; and the low-temperature closed isocyanate crosslinking agent is added, so that hydroxyl groups in the photocuring resin and the photopolymerization monomer can be subjected to full crosslinking polymerization at a low temperature, the strength and stability of a cured film are further improved, the influence on a color filter is reduced, and the Organic Light Emitting Diode (OLED) and a quantum dot-based display device are more suitable for use.
Description
Technical Field
The invention relates to a low-temperature negative black photoresist composition and a black matrix thereof, belonging to the technical field of semiconductor materials.
Background
A black matrix, a black columnar spacer, and other patterned light-shielding films are generally formed on a panel used for a liquid crystal display device, and a black bank as a light-shielding film is formed on a panel used for an organic EL display device for the purpose of partitioning a light-emitting layer. In such applications, various photoresists for forming a light-shielding film, which contain a light-shielding black pigment and a photopolymerization initiator, have been proposed.
The LCD includes an upper substrate, a lower substrate, and liquid crystal interposed between the substrates. If necessary, a touch screen panel or the like may be connected to the upper substrate. It is typically fabricated after an assembly step in which the color filters and Thin Film Transistors (TFTs) are combined. In order to minimize the influence on the color filter that has been manufactured, the photoresist must be cured at a low temperature to prepare a cured film.
In addition, OLED and Quantum Dot (QD) -based display devices require a photoresist suitable for curing at low temperatures.
However, there are the following problems: the composition was not sufficiently crosslinked when cured at low temperature, a cured film could not be formed, or the strength thereof was insufficient, and the chemical resistance of the sample was poor. Thus, there is a need for compositions that can be cured at low temperatures.
Conventional colored photoresists that are currently curable at low temperatures use an excess of a thermal curing agent (such as an epoxy compound) or an additive for reducing the reaction energy in order to increase the degree of curing at low temperatures.
However, these materials have problems in storage stability, which leads to problems such as peeling and insufficient chemical resistance in the process of preparing a cured film.
There is therefore a need for a photoresist that is suitable for curing at low temperature conditions.
Disclosure of Invention
In order to solve the technical problems, the invention provides a low-temperature negative black photoresist composition, which can be fully crosslinked and cured to form a cured film under a low-temperature condition, and the specific technical scheme is as follows:
a low temperature negative black photoresist composition comprising an organic solvent and solutes dissolved in the organic solvent, the solutes comprising from 15 to 60% by weight of the total composition, wherein the solutes comprise: the light-cured resin contains double bonds and hydroxyl groups, alkali-soluble acrylate light polymerization monomers, a photoinitiator, a coloring agent, a low-temperature blocked isocyanate crosslinking agent and a surfactant;
100 parts by weight of solute, 10 to 35 parts by weight of light-cured resin containing double bonds and hydroxyl groups, 0.01 to 50 parts by weight of photoinitiator,
The alkali-soluble acrylate photopolymerization monomer is one or more of succinic anhydride modified or non-modified pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.
Further, the light-cured resin containing double bonds and hydroxyl groups comprises one or more of an acrylic resin, Cardo resin, polyester resin, polyurethane resin and epoxy resin containing unsaturated double bonds.
Further, the weight average molecular weight of the light-cured resin is in the range of 1000-50000 Da.
Further, the photoinitiator is one or more of OXE-01, OXE-02 and OXE-03 which are commercially available from BASF.
Further, the low-temperature blocked isocyanate crosslinking agent can perform a crosslinking reaction with hydroxyl and carboxyl in the photocurable resin and the monomer at a temperature of 80-120 ℃, and the low-temperature blocked isocyanate crosslinking agent is one of the commercially available MF-K60X, Dutch Tuona FAB or FAC of Japan.
Further, the black colorant is an inorganic black colorant or an organic black colorant or a combination of both.
Further, the inorganic black colorant includes one or more of carbon black, titanium black, synthetic iron black, and metal oxide; the organic black colorant comprises one or more of aniline black, lactam black and perylene black.
Further, the solvent is one of propylene glycol monopropyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, dipropylene glycol methyl ether acetate, propylene glycol butyl ether acetate, toluene, xylene, methyl ethyl ketone, 4-hydroxy-4-methyl-2-pentanone, cyclopentanone, or cyclohexanone.
A black matrix is synthesized by the following steps:
coating a photoresist composition on a substrate, and pre-baking at a temperature of 60 ℃ to 130 ℃ to remove a solvent; then exposing the substrate with a photomask having a desired pattern at a wavelength of 365nm in a wavelength band of 200 to 500nm at a wavelength of 10 to 200mJ/cm2The exposure rate of (a); developing using a developer to form a pattern on the coating layer; the patterned coating is subjected to a post-bake at a temperature of 80 ℃ to 120 ℃ for 10 minutes to 5 hours.
The beneficial effects of the invention are: the photoresist composition disclosed by the invention is added with the light-cured resin containing double bonds and hydroxyl groups and the alkali-soluble acrylate photopolymerization monomer, and polymerization is initiated by the photoinitiator, so that the adhesiveness of the photoresist is improved; and the low-temperature closed isocyanate crosslinking agent is added, so that hydroxyl groups in the photocuring resin and the photopolymerization monomer can be subjected to full crosslinking polymerization at a low temperature, the strength and stability of a cured film are further improved, the influence on a color filter is reduced, and the Organic Light Emitting Diode (OLED) and a display device based on quantum dots are more suitable for use.
Detailed Description
The present invention is further illustrated by the following examples, which are intended to be purely exemplary and are not intended to limit the scope of the invention, which is to be given the full breadth of the claims appended hereto.
The low-temperature negative black photoresist composition comprises an organic solvent and a solute dissolved in the organic solvent, wherein the solute accounts for 15-60% of the total weight of the composition, and comprises the following components: the light-cured resin contains double bonds and hydroxyl groups, alkali-soluble acrylate photopolymerization monomers, a photoinitiator, a black colorant, a low-temperature blocked isocyanate crosslinking agent and a surfactant;
the content of the light-cured resin containing double bonds and hydroxyl groups in 100 parts by weight of solute is 10-35 parts by weight, the content of the photoinitiator is 0.01-50 parts by weight, wherein the light-cured resin containing double bonds and hydroxyl groups comprises one or more of acrylic resin, Cardo resin, polyester resin, polyurethane resin and epoxy resin containing unsaturated double bonds, the weight-average molecular weight of the light-cured resin is in the range of 1000-50000Da, and the adhesion of the obtained cured film to a substrate is excellent, the physical and chemical properties are favorable, and the viscosity is proper;
The photoinitiator is one or more of OXE-01, OXE-02 and OXE-03 commercially available from BASF.
The alkali-soluble acrylate photopolymerization monomer is one or more of succinic anhydride modified or non-modified pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.
The low-temperature blocked isocyanate crosslinking agent can perform crosslinking reaction with hydroxyl and carboxyl in the light-cured resin and the monomer at the temperature of 80-120 ℃, and the low-temperature blocked isocyanate crosslinking agent is one of the commercially available MF-K60X, Dutch Tuonan FAB or FAC of Asahi Kasei.
When the weight of the photocurable resin is 15-35% or 20-35% based on the total weight of the photoresist composition, the adhesion and chemical resistance of the product can be enhanced.
The black colorant is an inorganic black colorant or an organic black colorant or a combination of the two, and the inorganic black colorant comprises one or more of carbon black, titanium black, synthetic iron black and metal oxide; the organic black colorant comprises one or more of aniline black, lactam black, and perylene black.
The organic solvent is one of propylene glycol monopropyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, dipropylene glycol methyl ether acetate, propylene glycol butyl ether acetate, toluene, methyl ethyl ketone, 4-hydroxy-4-methyl-2-pentanone, cyclopentanone or cyclohexanone.
The components of the black photoresist compositions of examples and comparative examples are shown in table 1:
TABLE 1
Example 1:
15G of a photocurable resin (A), 3G of a photopolymerizable monomer (B), dipentaerythritol pentaacrylate, 1G of a photoinitiator (D), a black color paste (E), a low-temperature blocked isocyanate crosslinking agent (F) and 0.02G of a surfactant (G) were uniformly mixed, the mixture was dissolved in propylene glycol monomethyl ether acetate so that the solid content of the mixture was 14 parts by weight, the solution was stirred for 2 hours and filtered through a membrane filter having a pore size of 0.2 μm to obtain a composition solution having a solid content of 14 parts by weight.
Example 2 and comparative example 1:
photoresist compositions were each prepared in the same manner as in example 1 except that the contents of the respective components were changed as shown in table 2:
TABLE 2
Preparing a black matrix:
the photoresist compositions obtained in each of examples and comparative examples were coated on a substrate, and subjected to pre-baking at a temperature of 60 ℃ to 130 ℃ to remove the solvent; then exposing using a photomask having a desired pattern; and subjected to development using a developer, which may be a potassium hydroxide solution, to form a pattern on the coating, the patterned coating Postbaking at a temperature of 80 to 120 ℃ for 10 minutes to 5 hours to produce a desired cured film, exposing to light in a wavelength band of 200 to 500nm at a wavelength of 365nm at a wavelength of 10 to 200mJ/cm2The exposure rate of (2) is increased to obtain a target pattern, and then testing is performed.
Test 1: evaluation of tackiness
The resin compositions prepared in examples and comparative examples were each coated on a glass substrate by spin coating, and then the coated substrate was pre-baked on a hot plate maintained at 110 ℃ for 90 seconds to form a dried film.
A black matrix was obtained in the same manner as in example 1, except that a photomask in which each pattern of 6 lines in the range of 1 μm to 30 μm was separated at 1 μm intervals was used, and then, the degree of the smallest line pattern remaining in the 1 to 30 μm line patterns on the silicon nitride substrate was observed using a microscope, and the pattern of the lowest CD size remaining after the line pattern was separated from the mask during the observation using a microscope was evaluated as development tackiness.
The smaller the minimum residual pattern size, the better the development tack, specifically, when the minimum residual pattern size is 4 μm or less, the mark is high; when the particle size is 5-8 μm, marking as medium; when it is 8 μm or more, it is marked as low.
And (3) testing 2: evaluation of chemical resistance
Cured films having a thickness of 1 (. + -. 0.1) μm, prepared by the same method as in test example 1, were cut into a size of 2cm × 1cm to prepare samples. The chemically resistant container was loaded with 10ml of PGMEA, capped and subjected to a water bath at 90 ℃; the sample was then immersed and soaked for 10 minutes, after which time the sample was removed, cooled to room temperature and washed with running water. The thickness of the sample was measured before and after immersion in the solvent using the SNU apparatus.
When the thickness variation of the sample is not more than 10%, the resistance to chemicals of the sample is excellent;
when the thickness of the sample is changed by more than 10% and not more than 20%, the chemical resistance of the sample is normal;
when the thickness of the sample is changed by more than 20%, the chemical resistance of the sample is unqualified;
the results obtained in test 1 and test 2 for example 1, example 2 and comparative example 1 are shown in table 3:
TABLE 3
| Recipe number | Chemical resistance | Tackiness (pattern size μm) | Tackiness (grade judgment) |
| Example 1 | Is excellent in | 3μm | Height of |
| Example 2 | In general | 7μm | In |
| Comparative example 1 | Fail to be qualified | 15μm | Is low in |
As shown in table 3 above, the photoresist obtained in example 1 was excellent in both of the adhesiveness and the chemical resistance, while comparative example 1 was inferior in both of the adhesiveness and the chemical resistance, and it was found that the composition of the example within the scope of the present invention was excellent in the chemical resistance and the adhesiveness as a whole; in contrast, the compositions of the comparative examples that are not within the scope of the present invention show at least one of these properties to be disadvantageous.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (9)
1. A low-temperature negative black photoresist composition is characterized in that: comprises an organic solvent and a solute dissolved in the organic solvent, wherein the solute comprises, by weight, 15 to 60% of the total composition: the light-cured resin contains double bonds and hydroxyl groups, an alkali-soluble acrylate photopolymerization monomer, a photoinitiator, a black colorant, a low-temperature blocked isocyanate crosslinking agent and a surfactant;
100 parts by weight of solute, 10 to 35 parts by weight of light-cured resin containing double bonds and hydroxyl groups, 0.01 to 50 parts by weight of photoinitiator,
the alkali-soluble acrylate photopolymerization monomer is one or more of succinic anhydride modified or non-modified pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.
2. The low temperature negative black photoresist composition according to claim 1, wherein: the light-cured resin containing double bonds and hydroxyl groups comprises one or more of unsaturated double-bond-containing acrylic resin, Cardo resin, polyester resin, polyurethane resin and epoxy resin.
3. The low temperature negative black photoresist composition according to claim 1, wherein: the weight-average molecular weight of the light-cured resin is in the range of 1000-50000 Da.
4. The low temperature negative black photoresist composition according to claim 1, wherein: the photoinitiator is one or more of OXE-01, OXE-02 and OXE-03 which are commercially available from BASF.
5. The low temperature negative black photoresist composition according to claim 1, wherein: the low-temperature blocked isocyanate crosslinking agent can perform crosslinking reaction with hydroxyl and carboxyl in the light-cured resin and the monomer at the temperature of 80-120 ℃, and is one of Japanese Asahi Kasei-Kasei MF-K60X, Dutch Tuona FAB or FAC.
6. The low temperature negative black photoresist composition according to claim 1, wherein: the black colorant is an inorganic black colorant or an organic black colorant or a combination of both.
7. The low temperature negative black photoresist composition according to claim 6, wherein: the inorganic black colorant comprises one or more of carbon black, titanium black, synthetic iron black and metal oxides; the organic black colorant comprises one or more of aniline black, lactam black and perylene black.
8. The method of claim 1, wherein: the solvent is one of propylene glycol monopropyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, dipropylene glycol methyl ether acetate, propylene glycol butyl ether acetate, toluene, xylene, methyl ethyl ketone, 4-hydroxy-4-methyl-2-pentanone, cyclopentanone or cyclohexanone.
9. A black matrix, comprising: prepared using the low temperature negative black photoresist composition of claim 1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210052881.6A CN114755890A (en) | 2022-01-18 | 2022-01-18 | Low-temperature negative black photoresist composition and black matrix thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210052881.6A CN114755890A (en) | 2022-01-18 | 2022-01-18 | Low-temperature negative black photoresist composition and black matrix thereof |
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| CN114755890A true CN114755890A (en) | 2022-07-15 |
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| CN202210052881.6A Pending CN114755890A (en) | 2022-01-18 | 2022-01-18 | Low-temperature negative black photoresist composition and black matrix thereof |
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