CN114967323A - Photoresist composition, optical film and method for manufacturing optical film - Google Patents

Photoresist composition, optical film and method for manufacturing optical film Download PDF

Info

Publication number
CN114967323A
CN114967323A CN202110214392.1A CN202110214392A CN114967323A CN 114967323 A CN114967323 A CN 114967323A CN 202110214392 A CN202110214392 A CN 202110214392A CN 114967323 A CN114967323 A CN 114967323A
Authority
CN
China
Prior art keywords
acrylate
optical film
composition according
temperature
resist composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202110214392.1A
Other languages
Chinese (zh)
Inventor
黄晧伦
吴宜声
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
New Materials Co ltd
Original Assignee
New Materials Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by New Materials Co ltd filed Critical New Materials Co ltd
Priority to CN202110214392.1A priority Critical patent/CN114967323A/en
Publication of CN114967323A publication Critical patent/CN114967323A/en
Pending legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)

Abstract

The disclosure provides a photoresist composition, comprising an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, a thermal initiator, a black colorant and a solvent, wherein the photopolymerizable compound accounts for 15-85 mass% of the composition, and comprises at least one ethylenically unsaturated monomer and at least one epoxy compound. The disclosure also provides an optical film and a method for manufacturing the optical film.

Description

Photoresist composition, optical film and method for producing optical film
Technical Field
The present invention relates to a photoresist composition, and more particularly, to a photoresist composition for low temperature processes, an optical film and a method for manufacturing the optical film.
Background
A light-shielding film patterned with a black matrix (black matrix) or a black column spacer (black column spacer) is generally formed in a display device. The photosensitive composition for forming the light-shielding film contains raw materials such as an adhesive, a colorant, and a photopolymerizable compound. In recent years, display devices have been developed to be flexible, and display devices have been manufactured using flexible substrates instead of glass substrates. The plurality of flexible substrates include organic materials (e.g., plastic films). Since the heat resistance of the plastic substrate is lower than that of the glass substrate, it is necessary to lower the heat curing temperature of the photosensitive composition. However, the resistance to chemical and mechanical properties of the light-shielding film are required, and a catalyst is generally used at a low heat curing temperature. However, the catalyst is often poor in solubility, and foreign matter is generated, and the compatibility with the photosensitive composition is poor.
Disclosure of Invention
It is an object of some embodiments of the present invention to provide a photoresist composition that can be used in low temperature processes.
It is another object of some embodiments of the present invention to provide an optical film prepared by a low temperature process, which has a suitable light transmittance and good chemical and mechanical resistance.
In some embodiments of the present invention, a photoresist composition includes (a) an alkali soluble resin; (B) a photopolymerizable compound; (C) a photoinitiator; (D) a thermal initiator; (E) a black colorant; and (F) a solvent; wherein the photopolymerizable compound (B) accounts for 15-85 mass% of the composition, and comprises at least one ethylenically unsaturated monomer and at least one epoxy compound.
In an embodiment of the invention, the alkali-soluble resin (a) is an acrylic resin and has a molecular weight of 2,000 to 50,000.
In one embodiment of the present invention, the alkali-soluble resin (A) is composed of a monomer structure represented by the following formula i, formula ii, formula iii, formula iv and formula v,
Figure BDA0002953369850000021
in one embodiment of the present invention, the at least one ethylenically unsaturated monomer has a structure represented by formula (I), and the at least one epoxy compound has a structure represented by formula (II), wherein R in formula (I) 1 、R 2 Is alkyl or alkoxy with 1 to 12 carbon atoms, and n is 3 to 12; r 'and R' in formula (II) are the same or different from each other and are each independently hydrogen, hydroxy, C1-C10 alkyl, C1-C10 alkoxy or- (R) a ) n -R b At least 1 of the above R 'and R' is- (R) a ) n -R b (ii) a At this time, R a Is hydrogen, alkylene of C1-C10, -R 5 -O-R 6 -or-R 7 -C(=O)O-R 8 -, in this case, R 5 ~R 8 The alkylene groups are the same or different from each other and are each independently a C1-C10 alkylene group; r b Hydrogen, mercapto, isocyanate group, carboxyl group, hydroxyl group, amino group, carbamido group, carbamate group, (methyl) acrylate group, C1-C10 alkyl group, C1-C10 alkoxy group, C3-C15 cycloalkyl group, C3-C15 heterocycloalkyl group, C6-C20 aryl or heteroaryl of C5 to C20; x is an integer of 1-500; y is an integer of 1 to 500; n is an integer of 0 or 1,
Figure BDA0002953369850000022
(R'SiO1.5)x(R"SiO1.5)y
(II)。
in an embodiment of the present invention, the photopolymerizable compound (B) includes Dipentaerythritol hexaacrylate (DPHA) and an organic-inorganic hybrid resin.
In an embodiment of the invention, the organic-inorganic hybrid resin is a hybrid resin formed by mixing nano-silica into a resin.
In an embodiment of the present invention, the photopolymerizable compound (B) further includes a polyfunctional urethane acrylate.
In an embodiment of the invention, the weight ratio of the at least one ethylenically unsaturated monomer and the at least one epoxy compound ranges from 1:5 to 5: 1.
In an embodiment of the present invention, the photoinitiator (C) is an oxime ester photoinitiator, and the thermal initiator (D) is an ionic thermal acid initiator.
In an embodiment of the invention, the black colorant (E) includes an organic black pigment.
In an embodiment of the present invention, the solvent (F) comprises a compound having a structure represented by formula (III), wherein R is 3 、R 4 Can be a linking group of ethers, alcohols, acetates,
Figure BDA0002953369850000031
in an embodiment of the present invention, the solvent (F) is Propylene Glycol Monomethyl Ether Acetate (PGMEA).
In an embodiment of the invention, the photoresist composition may further include an additive, and the additive may include a fluorine-based surfactant.
Some embodiments of the invention further provide an optical film, which is made of the photoresist composition, and has a transmittance of 2% or less for light with a wavelength of 380-700 nm, and a transmittance of 80% or more for light with a wavelength of 850nm and 940 nm.
In an embodiment of the invention, the optical film further has an optical density not less than 3 and a thickness of 2 ± 0.1 μm.
Several embodiments of the present invention also provide a method of manufacturing an optical film, including the steps of: coating the photoresist composition on a substrate; heating the photoresist composition at a first temperature to form a film layer; patterning the film layer; and heating the film layer at a second temperature to form an optical film, wherein the optical film has a transmittance of 2% or less for light with a wavelength of 380-700 nm and a transmittance of 80% or more for light with wavelengths of 850nm and 940 nm.
In an embodiment of the invention, the step of patterning the film further includes performing exposure and development of the film.
In an embodiment of the invention, the step of heating at the second temperature includes heating the film at a temperature less than 150 ℃ and greater than 90 ℃.
In an embodiment of the invention, the step of heating at the second temperature further includes heating the film layer at a temperature of 120 ℃ for 30 minutes and forming the optical film having a thickness of 2 ± 0.1 μm.
In an embodiment of the invention, the second temperature heating temperature and the first temperature heating temperature are not greater than 120 ℃.
The invention adopts the (B) photopolymerisable compound containing at least one ethylenically unsaturated monomer and at least one epoxy compound, so that the optical film with chemical resistance and mechanical property can be formed by photo-curing and thermal curing at the temperature of not more than 150 ℃ without adding a catalyst.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical means of the present invention more clearly understood, the present invention may be implemented in accordance with the content of the description, and in order to make the above and other objects, features, and advantages of the present invention more clearly understandable, the following specific preferred embodiments are described in detail.
Detailed Description
Unless otherwise defined, the low temperature mentioned in the present disclosure is equal to or less than 170 ℃, preferably 90 to 150 ℃; the high temperature is more than 170 ℃, preferably 200-240 ℃.
The present invention provides a photoresist composition which can be used in a low temperature process. The resist composition of the present invention comprises (A) an alkali-soluble resin, (B) a photopolymerizable compound, (C) a photoinitiator, (D) a thermal initiator, (E) a black colorant and (F) a solvent. (A) The alkali-soluble resin may be an acrylic resin composed of acrylic acid and acrylic acid derivatives as polymerization monomers, and preferably has a molecular weight of 2,000 to 50,000. (B) The photopolymerizable compound accounts for 15-85% of the photoresist composition by mass, and comprises at least one ethylenically unsaturated monomer and at least one epoxy compound, wherein the at least one epoxy compound can react with the (D) thermal initiator.
(A) Alkali soluble resin
The (a) alkali-soluble resin in several embodiments of the present invention is not particularly limited, but may be, for example, benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxy (meth) acrylate, 2-hydroxy (meth) acrylate, and the like, Tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate (2-hydroxypropyl (meth) acrylate), 2-hydroxy-3-chloropropyl (meth) acrylate (2-hydroxy-3-chloropropyl) acrylate, 4-hydroxy (meth) acrylate (4-hydroxybutyl (meth) acrylate), glycerol (meth) acrylate, 2-methoxybutyl (meth) acrylate, 3-methoxybutyl (meth) acrylate (3-methoxybutyl (meth) acrylate), ethoxydiethylene glycol (meth) acrylate, and methoxy (meth) acrylate, Methoxypropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate (phenoxy) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate (p-nonylphenoxypolyethylene glycol) acrylate (acrylate), p-nonylphenoxypolypropylene glycol (meth) acrylate (p-nonylphenoxypolypropylene glycol) (acrylate), glycidyl (meth) acrylate (glycidyl acrylate), dicyclopentyl (meth) acrylate (dicyclopentyl (meth) acrylate), dicyclopentyl (meth) acrylate (dicyclopentyl (methacrylate), dicyclopentyl (methyl) acrylate (dicyclopentyl (methyl) acrylate), and cyclohexyl (methyl) acrylate (dicyclopentyl (methacrylate) acrylate (methyl) acrylate (dicyclopentyl (methacrylate), phenoxydiethylene glycol (meth) acrylate (methacrylate), phenoxydiethylene glycol (methyl) acrylate (dicyclopentyl (methyl) acrylate), and (dicyclopentyl) acrylate (methyl acrylate (dicyclopentyl) acrylate (dicyclopentyl (methyl) acrylate (dicyclopentyl (methyl acrylate) acrylate (dicyclopentyl) acrylate (dicyclopentyl (methyl acrylate) acrylate (dicyclopentyl (methyl acrylate) acrylate (dicyclopentyl (methyl acrylate) acrylate (dicyclopentyl acrylate) acrylate (dicyclopentyl (methyl acrylate) acrylate, and (methyl acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, and (methyl acrylate) acrylate, octadecyl (meth) acrylate, (hexyl (meth) acrylate), (nonyl (meth) acrylate), (decyl (meth) acrylate), (lauryl (meth) acrylate), methyl α -hydroxymethacrylate, ethyl α -hydroxymethacrylate, propyl α -hydroxymethacrylate, butyl α -hydroxymethacrylate, and the like. In one embodiment of the present invention, (A) the alkali-soluble resin may be composed of monomer structures represented by the following formulas i, ii, iii, iv and v,
Figure BDA0002953369850000051
(B) photopolymerizable compound
The photopolymerizable compound (B) in several embodiments of the present invention is not particularly limited, but may preferably include at least one ethylenically unsaturated monomer and at least one epoxy compound. In some embodiments of the present invention, the weight ratio of the at least one ethylenically unsaturated monomer to the at least one epoxy compound may be in the range of 1:5 to 5:1, in other embodiments of the present invention may be in the range of 1:2 to 2:1, and in further embodiments of the present invention may be in the range of 1: 1.
The epoxy compound is not particularly limited, and examples thereof include bisphenol type epoxy resins (biphenol type epoxy resins), novolac type epoxy resins (novolac type epoxy resins), glycidyl ester type epoxy resins (glycidyl ester type epoxy resins), glycidyl amine type epoxy resins (glycidyl amine type epoxy resins), linear type aliphatic epoxy resins (linear aliphatic epoxy resins), alicyclic epoxy resins (alicyclic epoxy resins), biphenyl type epoxy resins (biphenol type epoxy resins), and the like. In one embodiment of the present invention, the epoxy compound may be a siloxane compound, a compound having a structure represented by the following formula (II), wherein R 'and R' are the same or different from each other, and each independently represents hydrogen, hydroxy, alkyl of C1-C10, alkoxy of C1-C10, or- (R) a ) n -R b At least 1 of the above R 'and R' is- (R) a ) n -R b (ii) a At this time, R a Is hydrogen, alkylene of C1-C10, -R 5 -O-R 6 -or-R 7 -C(=O)O-R 8 -, in this case, R 5 ~R 8 The alkylene groups are the same or different from each other and are each independently a C1-C10 alkylene group; r b Hydrogen, mercapto, isocyanate group, carboxyl group, hydroxyl group, amino group, carbamido group, carbamate group, (methyl) acrylate group, C1-C10 alkyl group, C1-C10 alkoxy group, C3-C15 cycloalkyl, C3-C15 heterocycloalkyl, C6-C20 aryl or C5-C20 heteroaryl; x is an integer of 1-500; y is an integer of 1 to 500; n is an integer of 0 or 1. Further, (B) the photopolymerizable compound may comprise an organic-inorganic hybrid resin having an epoxy compound, preferably a hybrid resin in which nanosilica is blended into a resin,
(R'SiO1.5)x(R"SiO1.5)y
(II)。
the ethylenically unsaturated monomer in the photopolymerizable compound (B) in some embodiments of the invention is not particularly limited, for example, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, phenoxyethyl (meth) acrylate, polyoxyethylene (meth) acrylate, polyethylene glycol (meth) acrylate, polypropylene glycol (meth) acrylate, polyoxypropylene (meth) acrylate, trimethylolethane triacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, pentaerythritol diacrylate, pentaerythritol diacetate, and the like. In one embodiment of the present invention, the ethylenically unsaturated monomer has a structure represented by formula (I), wherein R is 1 、R 2 Is alkyl or alkoxy having 1 to 12 carbon atoms, and n is 3 to 12
Figure BDA0002953369850000061
(C) Photoinitiator
The photoinitiator (C) in some embodiments of the present invention is not particularly limited, and may be, for example, an acetophenone-based compound, a diimidazole-based compound, a triazine-based compound, an oxime-based compound, or the like. In some embodiments of the present invention, (C) the photoinitiator may preferably be an oxime-based compound, for example, 1, 2-octanedione-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (1,2-octadione-1- (4-phenylthio) phenyl-2- (o-benzoyloxime)), ethanone-1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -1- (o-acetyloxime) (ethanone-1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -1- (o-acetyloxime)), N-1919(Adeka), OXE-01, OXE-02, OXE-3.
(D) Thermal initiator
The (D) thermal initiator in several embodiments of the present invention is not particularly limited, and any suitable thermal initiator may be used, for example, an ionic thermal acid initiator or a thermal radical initiator. The thermal initiator may include, but is not limited to, a thermally activated curing agent for the epoxy groups, which may release a strong acid at high temperatures to catalyze the crosslinking reaction of the epoxy groups. The thermal acid initiator can be, for example, any onium salt having complex anions of the BF4-, PF6-, SbF6-, CF3SO 3-and (C6F5) 4B-type, such as sulfonium salts and iodonium salts. The thermal acid initiator can be selected from K-PURE, CXC-1612, CXC-1614, TAG-2172, TAG-2179, TAG-2678, TAG2689 (manufactured by King Industries, Inc.), SI-45, SI-60, SI-80, SI-100, SI-110, and SI-150 (manufactured by shin chemical Industries, Ltd.).
(E) Black colorant
The black colorant (E) in some embodiments of the present invention is not particularly limited, and may include carbon black, a black pigment, or a combination thereof, and may further include a color pigment. The black pigment is organic black pigment such as lactam black, aniline black and perylene black pigment. In one embodiment of the present invention, the black pigment is a perylene black pigment. (E) The black colorant preferably imparts high light-shielding properties, low conductivity and good transmittance in the near-infrared region to the photoresist composition and the optical film produced therefrom.
(F) Solvent(s)
The (F) solvent in the several embodiments of the present invention is not particularly limited, and may be one or a mixture of two or more. In one embodiment of the present invention, the solvent (F) comprises a compound having a structure represented by formula (III), wherein R3 and R4 can be ethers, alcohols, and acetates,
Figure BDA0002953369850000071
the photoresist composition of the embodiment of the invention may further include one or more additives such as a surfactant, a dispersant, an antioxidant, an ultraviolet light absorber, a thermal polymerization inhibitor, a leveling agent, and the like. In one embodiment of the present invention, the surfactant used is a fluorine-based surfactant.
As shown in table 1 below, examples 1 to 5 illustrate the components and contents of the photoresist composition of the present invention, wherein the ratio of the ethylenically unsaturated monomer to the epoxy compound may be 5: 1-1: 5, (C) the photoinitiator may be selected from the OXE series.
Table 1: EXAMPLES 1 to 5 Photoresist compositions
Figure BDA0002953369850000081
The resist compositions of comparative examples 1 to 5 were prepared. The differences between comparative examples 1 to 5 and the present invention are mainly in the composition of the photopolymerizable compound (B) (comparative examples 1 to 2 and 4 to 5) and the composition of the colorant (comparative examples 2 to 5), which are shown in Table 2 below.
Table 2: comparative examples 1 to 5 resist compositions
Figure BDA0002953369850000082
Figure BDA0002953369850000091
Some embodiments of the present invention further provide an optical film made of the photoresist composition, and a method for manufacturing the optical film, comprising the steps of: coating the photoresist composition on a substrate; heating the photoresist composition at a first temperature to form a film layer; patterning the film layer; and heating the film layer at a second temperature and forming the optical film, wherein the patterning comprises exposure and development of the film layer. The first temperature is a temperature of no greater than 170 ℃, preferably no greater than 150 ℃, less preferably no greater than 120 ℃, or lower, such as no greater than 90 ℃. The second temperature is not greater than 170 deg.C, more preferably not greater than 150 deg.C. In one embodiment of the present invention, the second heating step includes heating the film at a temperature less than 150 ℃ and greater than 90 ℃, for example, heating the film at a temperature of 120 ℃ for 30 minutes. An optical film having a thickness of 2 ± 0.1 μm can be formed after completion. The following example 6 illustrates a method for producing an optical film of the present invention.
Example 6: method for manufacturing optical film
The photoresist compositions of examples 1 to 5 were spin-coated on a substrate, and the substrate was placed on a heating plate maintained at 90 ℃ for 2 minutes, thereby forming a film layer on the substrate. The substrate may be a glass or plastic substrate. Followed by exposure. The photo mask is placed on the film layer, and then the film layer and the photo mask are irradiated by ultraviolet light. The photomask used in the present example has specification characteristics of 1-50 μm line/space pattern and the pattern has gradually changing transmittance within the range of 1% -100%, the ultraviolet light irradiation is performed at 200 μm intervals under the condition of 200mJ/cm2 using a 1kW high-pressure mercury lamp without any special optical filter, and the mercury lamp contains all g, h and i rays.
In this example, an aqueous KOH solution (0.045%) was used as a developing solution, and the exposed film layer was immersed in the developing solution for 60 seconds. After development, the film layer was washed with distilled water and dried with nitrogen gas, followed by heating in an oven set to 120 ℃ for 30 minutes, to obtain an optical film of the present invention. The compositions of comparative examples 1 to 5 were prepared into optical films by the same method.
The compositions of examples 1 to 5 and the compositions of comparative examples 1 to 5 were further evaluated for each of the optical films. The evaluation content includes: optical film thickness, transmittance, optical density, chemical resistance and mechanical properties. Example 7 below illustrates the method of evaluation and presents the evaluation results of each optical film.
Example 7: evaluation method and evaluation result thereof
Optical film thickness: the obtained optical film was measured by a contact type film thickness meter Alpha step (manufactured by Veeco) and was confirmed to have a thickness of 2. + -. 0.1. mu.m.
Penetration rate: the transmittance at a wavelength of 200 to 1,100nm was confirmed by using a visible light photometer (U-2900 HITACHI). Wherein, when the transmittance of visible light at 380-700 nm is less than or equal to 2%, and the transmittance of infrared light at 850nm and 940nm is greater than or equal to 80%, the value is evaluated as O. Gamma is rated when the transmittance of visible light is more than 2% at 380-700 nm or the transmittance of infrared light is less than 80% at 850nm and 940 nm.
Optical density: an Optical densitometer was used to measure OD (Optical Density), with OD ≧ 3.0 rated O, and OD < 3.0 rated gamma.
Chemical resistance: the resistance was evaluated using an alcohol wiping film in which 50 back and forth wipes with no residual color were rated as O, 50 back and forth wipes with slight residual color were rated as Delta, and 50 back and forth wipes with severe residual color were rated as gamma.
Mechanical property: the mechanical properties were evaluated using a semi-mechanical pencil hardness. The evaluation results of the optical films made from the resist compositions are shown in Table 3 below.
TABLE 3
Figure BDA0002953369850000101
As can be seen from tables 1-3, the photoresist compositions of several embodiments of the present invention have a thickness of 2 + -0.1 μm, and pass the transmittance, optical density, chemical resistance and mechanical property tests under the temperature condition not exceeding 150 ℃. In several embodiments of the present disclosure, the epoxy compound may be reacted with (D) a thermal initiator, thereby imparting sufficient chemical resistance and mechanical properties to the optical film of several embodiments of the present disclosure. In contrast to the comparative examples, even if the amount of the photopolymerizable compound of the ethylenically unsaturated monomer is increased, the effects of the examples of the present invention cannot be achieved under the same production conditions. In some embodiments of the present invention, the organic black pigment can provide the optical film with an optical density OD of 3.0 or more, a transmittance of 2% or less for visible light with a wavelength of 380-700 nm, and a transmittance of 80% or more for infrared light with a wavelength of 850nm and 940 nm. Based on the above, the invention is suitable for various substrates and can be used as a photoresist element of a traditional glass substrate and an organic flexible film material.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (20)

1. A photoresist composition, comprising:
(A) an alkali soluble resin;
(B) a photopolymerizable compound;
(C) a photoinitiator;
(D) a thermal initiator;
(E) a black colorant; and
(F) a solvent;
wherein the photopolymerizable compound (B) accounts for 15-85 mass% of the photoresist composition, and comprises at least one ethylenically unsaturated monomer and at least one epoxy compound.
2. The resist composition according to claim 1, wherein the alkali-soluble resin (A) is an acrylic resin and has a molecular weight of 2,000 to 50,000.
3. The resist composition according to claim 2, wherein the alkali-soluble resin (A) is composed of a monomer structure represented by the following formulae i, ii, iii, iv and v,
Figure FDA0002953369840000011
4. the photoresist composition of claim 1, wherein the at least one ethylenically unsaturated monomer has a structure of formula (I) and the at least one epoxy compound has a structure of formula (II), wherein R of formula (I) 1 、R 2 Is alkyl or alkoxy with 1 to 12 carbon atoms, and n is 3 to 12; r 'and R' in formula (II) are the same or different from each other and are each independently hydrogen, hydroxy, C1-C10 alkyl, C1-C10 alkoxy or- (R) a ) n -R b At least 1 of the above R 'and R' is- (R) a ) n -R b (ii) a At this time, R a Is hydrogen, alkylene of C1-C10, -R 5 -O-R 6 -or-R 7 -C(=O)O-R 8 -, at this time, R 5 ~R 8 The alkylene groups are the same or different from each other and are each independently a C1-C10 alkylene group; r b Is hydrogen, sulfydryl, isocyanate group, carboxyl, hydroxyl, amido, carbamido, carbamate, (methyl) acrylate, C1-C10 alkyl, C1-C10 alkoxy, C3-C15 cycloalkyl, C3-C15 heterocycloalkyl, C6-C20 aryl or C5-C20 heteroaryl; x is an integer of 1 to 500; y is an integer of 1 to 500; n is an integer of 0 or 1,
Figure FDA0002953369840000021
(R'SiO1.5)x(R"SiO1.5)y
(II)。
5. the resist composition according to claim 1, wherein the photopolymerizable compound (B) comprises dipentaerythritol hexaacrylate and an organic-inorganic hybrid resin.
6. The resist composition according to claim 5, wherein the organic-inorganic hybrid resin is a hybrid resin in which nanosilica is blended into a resin.
7. The resist composition according to claim 1, wherein the photopolymerizable compound (B) further comprises a polyfunctional urethane acrylate.
8. The photoresist composition according to claim 1, wherein the weight ratio of the at least one ethylenically unsaturated monomer and the at least one epoxy compound is in a range of 1:5 to 5: 1.
9. The resist composition according to claim 1, wherein the photoinitiator (C) is an oxime ester photoinitiator and the thermal initiator (D) is an ionic thermal acid initiator.
10. The resist composition according to claim 1, wherein the (E) black colorant comprises an organic black pigment.
11. The photoresist composition of claim 1, wherein the solvent (F) comprises a compound having a structure of formula (III), wherein R3 and R4 can be ethers, alcohols, and acetates,
Figure FDA0002953369840000022
12. the resist composition according to claim 11, wherein the solvent (F) is propylene glycol monomethyl ether acetate.
13. The photoresist composition of claim 1, further comprising an additive, wherein the additive comprises a fluorine-based surfactant.
14. An optical film comprising the resist composition according to any one of claims 1 to 13, and having a transmittance of 2% or less for light having a wavelength of 380 to 700nm and a transmittance of 80% or more for light having a wavelength of 850nm and 940 nm.
15. The optical film of claim 14, wherein the optical film further has an optical density of not less than 3 and a thickness of 2 ± 0.1 μm.
16. A method of manufacturing an optical film, comprising:
coating a substrate with the resist composition according to any one of claims 1 to 13;
heating the photoresist composition at a first temperature to form a film;
patterning the film layer; and
and heating the film layer at a second temperature to form the optical film, wherein the optical film has a transmittance of less than or equal to 2% for light with a wavelength of 380-700 nm and a transmittance of more than or equal to 80% for light with wavelengths of 850nm and 940 nm.
17. The method of claim 16, wherein the step of patterning the film further comprises exposing and developing the film.
18. The method of manufacturing of claim 16, wherein the step of heating at the second temperature comprises heating the film layer at a temperature less than 150 ℃ and greater than 90 ℃.
19. The method of claim 18, wherein the second heating step further comprises heating the film layer at a temperature of 120 ℃ for 30 minutes to form the optical film having a thickness of 2 ± 0.1 μm.
20. The method of manufacturing of claim 16, wherein the second temperature heating temperature and the first temperature heating temperature are not greater than 120 ℃.
CN202110214392.1A 2021-02-26 2021-02-26 Photoresist composition, optical film and method for manufacturing optical film Pending CN114967323A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202110214392.1A CN114967323A (en) 2021-02-26 2021-02-26 Photoresist composition, optical film and method for manufacturing optical film

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110214392.1A CN114967323A (en) 2021-02-26 2021-02-26 Photoresist composition, optical film and method for manufacturing optical film

Publications (1)

Publication Number Publication Date
CN114967323A true CN114967323A (en) 2022-08-30

Family

ID=82973859

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110214392.1A Pending CN114967323A (en) 2021-02-26 2021-02-26 Photoresist composition, optical film and method for manufacturing optical film

Country Status (1)

Country Link
CN (1) CN114967323A (en)

Similar Documents

Publication Publication Date Title
CN108137794B (en) Binder resin and photosensitive resin composition containing same
CN101051186B (en) Negative photosensitive resin composition
JP2008031248A (en) Curable resin composition and method for forming cured coating film
KR101369486B1 (en) Positive Photosensitive Resin Composition and Cured Film Obtained Therefrom
JP2013534326A (en) Negative photosensitive resin composition
JP3228193B2 (en) Negative photoresist composition and pattern forming method using the same
CN102591147B (en) Compositions comprising sugar component and processes for photolithography
WO1998055521A1 (en) Light-absorbing polymer, composition forming light-absorbing coatings, light-absorbing coatings, and antireflection coating made by using the same
KR20140104768A (en) Colored photosensitive resin composition comprising the same
CN111032720B (en) Resin, photosensitive resin composition, resin cured film, and image display device
KR20130118450A (en) A photoactive compound including xanthene structure and an organic insulation layer composition comprising the same
KR20180029549A (en) Photosensitive resin composition and photo-cured pattern prepared from the same
CN114967323A (en) Photoresist composition, optical film and method for manufacturing optical film
EP3830153B1 (en) A composition
CN115494697A (en) Chemically amplified photoresist and preparation and use method thereof
KR20190137413A (en) A composition of anti-reflective hardmask
KR20090107022A (en) Process for producing polymer for semiconductor lithography
KR20150011070A (en) A photosensitive resin composition for spacer and a spacer using the same
CN111448517B (en) Adhesive resin and photosensitive resin composition or coating solution containing the same
KR100936998B1 (en) Photosensitive polysilsesquioxane resin composition and method for patterning membranes using the same
KR101535676B1 (en) A colored photosensitive resin composition, color filter and liquid crystal display device having the same
TW202233700A (en) Photoresist composition, optical film thereof, and method for making the optical film
KR20140104766A (en) Alkali soluble resin and photosensitive resin composition comprising the same
KR20090037172A (en) Cholate-based compound and negative-type photoresist resin composition comprising the same
KR20150145414A (en) Oxime ester compound and a photopolymerizable composition comprising the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination