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WO2024048893A1 - Composition de résine photosensible, couche de résine photosensible fabriquée à l'aide de celle-ci, et filtre coloré - Google Patents

Composition de résine photosensible, couche de résine photosensible fabriquée à l'aide de celle-ci, et filtre coloré Download PDF

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Publication number
WO2024048893A1
WO2024048893A1 PCT/KR2023/005404 KR2023005404W WO2024048893A1 WO 2024048893 A1 WO2024048893 A1 WO 2024048893A1 KR 2023005404 W KR2023005404 W KR 2023005404W WO 2024048893 A1 WO2024048893 A1 WO 2024048893A1
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Prior art keywords
photosensitive resin
photopolymerizable compound
resin composition
binder resin
weight
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Ceased
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PCT/KR2023/005404
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English (en)
Korean (ko)
Inventor
이상호
김사비나
김광섭
유정호
김지홍
김이주
김익진
조명호
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Samsung SDI Co Ltd
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Samsung SDI Co Ltd
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Priority to JP2024562918A priority Critical patent/JP2025514953A/ja
Priority to CN202380041838.2A priority patent/CN119343634A/zh
Publication of WO2024048893A1 publication Critical patent/WO2024048893A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • 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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
    • H10F39/10—Integrated devices
    • H10F39/12—Image sensors
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
    • H10F39/10—Integrated devices
    • H10F39/12—Image sensors
    • H10F39/18—Complementary metal-oxide-semiconductor [CMOS] image sensors; Photodiode array image sensors
    • H10F39/182—Colour image sensors

Definitions

  • This description relates to a photosensitive resin composition, a photosensitive resin film and a color filter manufactured using the same.
  • CMOS image sensor is a non-memory semiconductor that converts images received by a camera into digital signals and is a collection of pixels such as color filters, photo diodes, and amplifiers.
  • CIS for mobile devices requires more pixels and more cameras, increasing the demand for thinner and smaller image sensors.
  • CIS's photosensitive resin composition Photoresist, PR
  • PR photosensitive resin composition
  • the signal-to-noise ratio becomes an important issue. Since the driving method of CIS is based on the principle that light from the outside is transmitted through a color filter and the transmitted light is converted into an electrical signal while passing through a photo diode, a decrease in the size of the pixel means that the amount of light incident per unit pixel decreases. This means it is decreasing. Additionally, as the size of a pixel decreases, the distance between pixels becomes closer, so light transmitted from adjacent pixels may act as noise.
  • the green photosensitive resin composition is applied first to form a pattern, followed by the blue or red photosensitive resin composition, and finally the red or blue photosensitive resin composition. This is applied to form a pattern.
  • the red or blue photosensitive resin composition is applied between the uneven patterns formed by the lower green photosensitive resin composition, so the degree of filling between the patterns varies depending on the rheological properties of the composition, resulting in the actual red or blue composition pattern formed between the green composition patterns. There may be a large difference in thickness.
  • Thickness is an important factor in forming the signal of the color represented by the pattern because the thicker the color, the darker the color, and the thinner the color, the lighter the color. Therefore, the thickness uniformity of the pattern plays a decisive role in driving the CIS device.
  • One embodiment is to provide a photosensitive resin composition that has a low level difference between the pattern and the resin film when forming a photosensitive resin film on a patterned substrate for the purpose of improving SNR distribution (S. SNR) of CIS.
  • S. SNR SNR distribution
  • Another embodiment is to provide a photosensitive resin film manufactured using the photosensitive resin composition.
  • Another embodiment is to provide a color filter manufactured using the photosensitive resin film.
  • One embodiment includes (A) a binder resin; (B) photopolymerizable compound; (C) photopolymerization initiator; (D) colorant; and (E) a solvent;
  • the weight ratio of the binder resin to the photopolymerizable compound is 60/40 or more;
  • the weight average molecular weight of the binder resin is 4,000 g/mol to 9,000 g/mol;
  • the photosensitive resin composition is provided in which the photopolymerizable compound is a hexafunctional photopolymerizable compound alone or a mixture of a hexafunctional photopolymerizable compound and a bifunctional photopolymerizable compound.
  • the step according to Equation 1 below may be 1,000 ⁇ or less:
  • Equation 1 A is the height of the pattern of the patterned substrate, B is the maximum height of the photosensitive resin film formed in the area where the pattern of the patterned substrate exists, and C is the height of the pattern of the patterned substrate. This is the lowest height of the photosensitive resin film formed in the area not covered.
  • the colorant may include a blue pigment, a purple pigment, or a combination thereof.
  • the photosensitive resin film may be blue, and the pattern of the substrate may be green.
  • the acid value of the binder resin may be 30 KOHmg/g to 100 KOHmg/g.
  • the binder resin may be a hydrophobic acrylic binder resin.
  • the viscosity of the hexafunctional photopolymerizable compound at 25°C may be 5,500 to 8,000 cps.
  • the viscosity of the bifunctional photopolymerizable compound at 25° C. may be 600 to 700 cps.
  • the solvent is propylene glycol monomethyl ether acetate (PGMEA), n-Butyl Acetate (n-BA), ethylene glycol dimethyl ether, or a combination thereof. It can be included.
  • the photosensitive resin composition includes 0.5% by weight to 15% by weight of the (A) binder resin, based on the total amount of the photosensitive resin composition; 0.1% to 10% by weight of the (B) photopolymerizable compound; (C) 0.1% to 10% by weight of photopolymerization initiator; 0.5% to 15% by weight of the (D) colorant; And it may include the remaining amount of the solvent (E).
  • the photosensitive resin composition further contains malonic acid, 3-amino-1,2-propanediol, a silane-based coupling agent containing a vinyl group or (meth)acryloxy group, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof. It can be included.
  • Another embodiment provides a photosensitive resin film manufactured using the photosensitive resin composition.
  • Another embodiment provides a color filter including the photosensitive resin film.
  • Another embodiment is a CMOS image sensor including the color filter.
  • the step difference between the pattern and the resin film is formed to be low, and thus the SNR distribution (S. SNR) of the CIS can be improved.
  • Figure 1 is a schematic diagram for explaining the level difference between the pattern and the resin film.
  • substitution means that at least one hydrogen atom in the compound is a halogen atom (F, Cl, Br, I), hydroxy group, C1 to C20 alkoxy group, nitro group, cyano group, amine group, or already.
  • heterocycloalkyl group refers to cycloalkyl, cycloalkenyl, cycloalkynyl, and cycloalkyl group, respectively. It means that at least one hetero atom of N, O, S or P is present in the ring compound of ren.
  • (meth)acrylate means that both “acrylate” and “methacrylate” are possible.
  • “combination” means mixing or copolymerization. Additionally, “copolymerization” refers to block copolymerization to random copolymerization, and “copolymer” refers to block copolymerization to random copolymerization.
  • One embodiment provides a photosensitive resin composition that has a low level difference between the pattern and the resin film when forming a photosensitive resin film on a patterned substrate for the purpose of improving SNR distribution (S. SNR) of CIS.
  • S. SNR SNR distribution
  • Figure 1 is a schematic diagram for explaining the level difference between the pattern and the resin film.
  • a height (A+B) corresponding to the sum of the pattern height (A) of the substrate and the maximum height (B) of the photosensitive resin film formed in the area where the pattern of the substrate exists is , a difference occurs in the minimum height (C) of the photosensitive resin film formed in the area where the pattern of the substrate does not exist.
  • the level difference between the pattern and the resin film is affected by the type and ratio of transparent materials that contribute to pattern formation, such as binder resin, photopolymerizable compound, and solvent, rather than pigments directly related to color.
  • one embodiment includes (A) a binder resin; (B) photopolymerizable compound; (C) photopolymerization initiator; (D) colorant; and (E) a solvent;
  • the weight ratio of the binder resin to the photopolymerizable compound is 60/40 or more;
  • the weight average molecular weight of the binder resin is 4,000 g/mol to 9,000 g/mol;
  • the photosensitive resin composition is provided in which the photopolymerizable compound is a hexafunctional photopolymerizable compound alone or a mixture of a hexafunctional photopolymerizable compound and a bifunctional photopolymerizable compound.
  • the photosensitive resin film may be blue, and the pattern of the substrate may be green.
  • the colorant may include a blue pigment, a purple pigment, or a combination thereof, and a blue photosensitive resin film can be manufactured using such a colorant.
  • the step difference according to Equation 1 below may be 1,000 ⁇ or less:
  • Equation 1 A is the height of the pattern of the patterned substrate, B is the maximum height of the photosensitive resin film formed in the area where the pattern of the patterned substrate exists, and C is the height of the pattern of the patterned substrate. This is the lowest height of the photosensitive resin film formed in the area not covered.
  • the ⁇ Y (nm) value is the same as the step according to Equation 1 described above.
  • the thickness uniformity of the pattern is important for the CMOS image sensor (CIS). It plays a decisive role in driving.
  • the photosensitive resin composition of one embodiment can control the step according to Equation 1 to 1,000 ⁇ or less, specifically 998 ⁇ or less, 996 ⁇ or less, 994 ⁇ or less, 992 ⁇ or less, or 990 ⁇ or less by controlling the multiple factors. You can.
  • the hexafunctional It essentially includes a photopolymerizable compound, but as a bifunctional photopolymerizable compound is added, the closer the addition amount is controlled to 50/50, the lower the step according to Equation 1 above.
  • SNR can be improved by adjusting the transmission spectrum of the pigment or dye in the visible light region.
  • the overlapping area in the transmission spectrum of red, green, and blue that makes up the color filter is called crosstalk, and since this can act as noise for different colors, it is important to design the transmission spectrum to minimize this. do.
  • Crosstalk can be improved by mixing yellow pigment for red and green, and using violet pigment for blue.
  • the photosensitive resin composition forms a fine pattern
  • the roughness of the surface can affect the decrease in SNR, and after it is applied on a silicon wafer, the thickness deviation between the edge and center of the wafer, the presence or absence of stains and striations, etc. affect the S.SNR. can be given. This can be improved by changing the type, ratio, and content of transparent materials such as resin, monomer, solvent, and additives that contribute to pattern formation rather than pigments directly related to color.
  • the step difference according to Equation 1 becomes lower.
  • the weight ratio of the binder resin/photopolymerizable compound may be 60/40 or more or 70/30 or more, but less than 100/1.
  • the step according to Equation 1 becomes lower.
  • the weight average molecular weight of the binder resin may be 4,000 g/mol or more, but 9,000 g/mol or less, 8,000 g/mol or less, 7,000 g/mol or less, or 6,000 g/mol or less.
  • the weight average molecular weight of the binder resin is within the above range, it has excellent adhesion to the substrate, good physical and chemical properties, and appropriate viscosity.
  • the acid value of the binder resin may be 30 KOHmg/g to 100 KOHmg/g. When the acid value of the binder resin is within the above range, excellent pixel resolution can be obtained.
  • the binder resin may be a hydrophobic acrylic binder resin.
  • the binder resin is a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and may be a resin containing one or more acrylic repeating units.
  • the first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.
  • the first ethylenically unsaturated monomer may be included in an amount of 5% by weight to 50% by weight, for example, 10% by weight to 40% by weight, based on the total amount of the alkali-soluble resin.
  • the second ethylenically unsaturated monomer may include aromatic vinyl compounds such as styrene, ⁇ -methylstyrene, vinyltoluene, and vinylbenzylmethyl ether; Methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxy butyl (meth)acrylate, benzyl (meth)acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth)acrylate and phenyl (meth)acrylate; unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycid
  • binder resin examples include methacrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene copolymer, and methacrylic acid/benzyl methacrylate/2-hydroxyethyl methacrylate copolymer. , methacrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, etc., but is not limited thereto, and these may be used alone or in combination of two or more types.
  • the binder resin may be included in an amount of 0.5% by weight to 15% by weight, for example, 1% by weight to 5% by weight, based on the total amount of the photosensitive resin composition.
  • the binder resin When the binder resin is contained within the above range, developability is excellent when manufacturing a color filter, and crosslinking properties are improved to obtain excellent surface smoothness.
  • the photopolymerizable compound is a hexafunctional photopolymerizable compound alone or a mixture of a hexafunctional photopolymerizable compound (a first photopolymerizable compound) and a bifunctional photopolymerizable compound (a second photopolymerizable compound).
  • the weight ratio of the first/second photopolymerizable compound may be 50/50 or more and 75/25 or less.
  • the functional group included in each of the hexafunctional photopolymerizable compound and the bifunctional photopolymerizable compound may be a (meth)acrylate group.
  • the hexafunctional photopolymerizable compound may be dipentaerythritol hexaacrylate (DPHA), which is represented by the following formula and has a viscosity of 5,500 cps to 8,000 cps at 25°C.
  • DPHA dipentaerythritol hexaacrylate
  • the bifunctional photopolymerizable compound is represented by the following formula and has a viscosity of 600 cps to 700 cps at 25 ° C. )10 Diacrylate).
  • the photopolymerizable compound may be included in an amount of 0.1% by weight to 15% by weight, for example, 0.5% by weight to 5% by weight, based on the total amount of the photosensitive resin composition.
  • the photopolymerizable compound is included within the above range, sufficient curing occurs during exposure to light in the pattern formation process, resulting in excellent reliability and excellent developability in an alkaline developer.
  • the photopolymerization initiator is an initiator commonly used in photosensitive resin compositions, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, an oxime-based compound, or a combination thereof. You can use it.
  • acetophenone-based compounds examples include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyltrichloro acetophenone, p-t -Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropane-1 -one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc.
  • benzophenone-based compounds examples include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4 '-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc.
  • thioxanthone-based compounds examples include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone, etc. can be mentioned.
  • benzoin-based compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyldimethyl ketal.
  • triazine-based compounds examples include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3', 4'- Dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)-4, 6-bis(trichloromethyl)-s-
  • Examples of the oxime-based compounds include O-acyloxime-based compounds, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime) )-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl- ⁇ -oxyamino-1-phenylpropan-1-one etc. can be used.
  • O-acyloxime compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butane- 1-one, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione2 -oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-oneoxime-O-acetate and 1-(4-phenylsulfanylphenyl)-butane-1-oneoxime-O- Acetate, etc. can be mentioned.
  • the photopolymerization initiator may include carbazole-based compounds, diketone-based compounds, sulfonium borate-based compounds, diazo-based compounds, imidazole-based compounds, biimidazole-based compounds, and fluorene-based compounds.
  • the photopolymerization initiator may be used together with a photosensitizer that absorbs light, becomes excited, and then transmits the energy to cause a chemical reaction.
  • photosensitizer examples include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, etc. can be mentioned.
  • the photopolymerization initiator may be included in an amount of 0.1% by weight to 5% by weight, for example, 1% by weight to 3% by weight, based on the total amount of the photosensitive resin composition.
  • the photopolymerization initiator is included within the above range, curing occurs sufficiently during exposure during the pattern formation process to obtain excellent reliability, the heat resistance, light resistance, and chemical resistance of the pattern are excellent, resolution and adhesion are also excellent, and there is no damage from unreacted initiators. Deterioration of transmittance can be prevented.
  • the colorant may include a blue pigment, a purple pigment, or a combination thereof.
  • blue pigment examples include C.I. Blue pigment 15:6, C.I. Blue Pigment 15, C.I. Blue pigment 15:1, C.I. Blue pigment 15:2, C.I. Blue pigment 15:3, C.I. Blue pigment 15:4, C.I. Blue pigment 15:5, C.I. Copper phthalocyanine pigments such as blue pigment 16 and the like can be mentioned.
  • purple pigment examples include C.I. Violet pigment 1, C.I. Violet Pigment 19, C.I. Violet Pigment 23, C.I. Violet Pigment 27, C.I. Violet Pigment 28, C.I. Violet Pigment 29, C.I. Violet Pigment 30, C.I. Violet Pigment 32, C.I. Violet Pigment 37, C.I. Violet Pigment 40, C.I. Violet Pigment 42, C.I. Violet Pigment 50 or a combination thereof may be mentioned.
  • red pigment, green pigment, yellow pigment, black pigment, etc. may be further included.
  • red pigment examples include C.I. Red Pigment 254, C.I. Red Pigment 255, C.I. Red Pigment 264, C.I. Red Pigment 270, C.I. Red Pigment 272, C.I. Red Pigment 177, C.I. Red pigment 89, etc. can be mentioned.
  • green pigment examples include C.I. Green Pigment 7, C.I. Green Pigment 36, C.I. Green Pigment 58, C.I. Green pigment 59, etc. can be mentioned.
  • yellow pigment examples include C.I. Isoindoline pigments such as yellow pigment 139, C.I. Quinophthalone pigments such as yellow pigment 138, C.I. and nickel complex pigments such as yellow pigment 150.
  • black pigment examples include aniline black, perylene black, titanium black, and carbon black.
  • the above pigments can be used alone or in a mixture of two or more.
  • the pigment may be a yellow pigment, a green pigment, or a mixture thereof.
  • the pigment may be included in the photosensitive resin composition for a color filter in the form of a dispersion.
  • This pigment dispersion may be composed of the pigment, solvent, dispersant, dispersion resin, etc.
  • the solvent may be ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, etc.
  • propylene glycol methyl ether acetate is preferred. You can.
  • the dispersant helps the pigment to be uniformly dispersed in the dispersion, and nonionic, anionic, or cationic dispersants can be used.
  • nonionic, anionic, or cationic dispersants can be used.
  • Water, alkyl amine, etc. can be used, and these can be used alone or in a mixture of two or more types.
  • the dispersion resin may be an acrylic resin containing a carboxyl group, which can not only improve the stability of the pigment dispersion but also improve the patterning of the pixel.
  • the colorant may further include an organic solvent-soluble dye.
  • organic solvent-soluble dye examples include triarylmethane-based compounds, anthraquinone-based compounds, benzylidene-based compounds, xanthene-based compounds, phthalocyanine-based compounds, azaporphyrin-based compounds, and indigo-based compounds.
  • the dye and the pigment When the dye and the pigment are mixed and used, they can be mixed at a weight ratio of 1:9 to 9:1, specifically 3:7 to 7:3.
  • chemical resistance, durability, and maximum absorption wavelength can be controlled to an appropriate range, and high luminance and contrast ratio can be expressed at the desired color coordinate.
  • the colorant may be included in an amount of 0.5% by weight to 15% by weight, for example, 1% by weight to 10% by weight.
  • the colorant is included within the above range, the color reproduction rate is excellent, and the curability and adhesion of the pattern are excellent.
  • the solvent may be a material that is compatible with, but does not react with, the colorant, the binder resin, the photopolymerizable compound, and the photopolymerization initiator.
  • the solvent examples include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and
  • N-methylpyrrolidone dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid.
  • High boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, ⁇ -butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate can be mentioned.
  • the solvents include propylene glycol monomethyl ether acetate (PGMEA), n-Butyl Acetate (n-BA), and ethylene glycol dimethyl ether (Ethylene). glycol Dimethyl ether), or a combination thereof may be used.
  • the solvent may be included in the remaining amount, for example, 70% by weight to 90% by weight, for example, 80% by weight to 90% by weight, based on the total amount of the photosensitive resin composition.
  • the photosensitive resin composition has excellent applicability and a coating film with excellent flatness can be obtained.
  • the photosensitive resin composition contains malonic acid to prevent stains or spots upon application, to improve leveling performance, and to prevent the creation of residues due to non-development; 3-amino-1,2-propanediol; A coupling agent containing a vinyl group or (meth)acryloxy group; leveling agent; Surfactants; and at least one additive selected from radical polymerization initiators.
  • the additives can be easily adjusted according to desired physical properties.
  • the coupling agent may be a silane-based coupling agent, and examples of the silane-based coupling agent include trimethoxysilyl benzoic acid, ⁇ methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, ⁇ Examples include isocyanate propyl triethoxysilane, ⁇ glycidoxy propyl trimethoxysilane, and ⁇ epoxycyclohexyl)ethyltrimethoxysilane, and these can be used alone or in a mixture of two or more types.
  • the silane-based coupling agent may be specifically used in an amount of 0.01 to 1 part by weight based on 100 parts by weight of the photosensitive resin composition.
  • the photosensitive resin composition for a color filter may further include a surfactant, such as a fluorine-based surfactant, if necessary.
  • a surfactant such as a fluorine-based surfactant
  • fluorine-based surfactant examples include DIC's F-482, F-484, and F-478, but are not limited thereto.
  • the surfactant is preferably contained in an amount of 0.01 wt% to 5 wt%, and more preferably in an amount of 0.01 wt% to 2 wt%, based on the total amount of the photosensitive resin composition. If it is outside the above range, it is undesirable because it may cause problems with foreign substances occurring after development.
  • antioxidants and stabilizers may be added to the photosensitive resin composition within the range that does not impair the physical properties.
  • a photosensitive resin film manufactured using the photosensitive resin composition according to the embodiment is provided.
  • the manufacturing method of the photosensitive resin film is as follows.
  • a photosensitive resin composition layer is formed by applying the above-described photosensitive resin composition to a thickness of, for example, 0.5 um to 10 um, using an appropriate method such as spin coating, roller coating, or spray coating, on a glass substrate.
  • Baking is performed at 80 to 100°C for 170 to 190 seconds using a hot-plate, exposure is performed at a power of 450 to 470 mJ using an exposure machine, and then the heating plate is heated to 210 to 250°C.
  • the photosensitive resin composition layer can be converted into a photosensitive resin film by baking on a hot-plate for 3 to 10 minutes.
  • the photosensitive resin film may have a transmittance of 85% or more, specifically 97% or more, for example, 90% or more in a wavelength range of 480 to 620 nm.
  • the photosensitive resin film may have a transmittance in a wavelength range of less than 480 nm and a transmittance in a wavelength range of more than 620 nm, respectively, of 15% or less, specifically 13% or less, for example, 10% or less.
  • the photosensitive resin film may have a small thickness while reaching the above spectral target.
  • the thickness of the photosensitive resin film may be 0.5 um or less, specifically 0.45 um or less, more specifically 0.4 um or less, for example, 0.35 um or less.
  • a color filter manufactured using the above-described photosensitive resin composition is provided.
  • the manufacturing method of the color filter is as follows.
  • a photosensitive resin composition layer is formed by applying the above-described photosensitive resin composition to a thickness of, for example, 0.5 um to 10 um, using an appropriate method such as spin coating, roller coating, or spray coating, on a glass substrate.
  • light is irradiated to the substrate on which the photosensitive resin composition layer is formed to form a pattern necessary for a color filter.
  • a light source used for irradiation UV, electron beams, or The above irradiation process can also be performed by further using a photoresist mask.
  • the photosensitive resin composition layer irradiated with the light source is treated with a developer.
  • the non-exposed portion of the photosensitive resin composition layer is dissolved, thereby forming a pattern necessary for the color filter.
  • crack resistance, solvent resistance, etc. can be improved by heating the image pattern obtained through development in the above process again or curing it by irradiation with actinic rays.
  • CMOS image sensor including the above-described color filter is provided.
  • Photosensitive resin compositions according to Reference Examples 1 to 15 were prepared by mixing the compositions shown in Tables 1 to 3 below.
  • the photopolymerization initiator was dissolved in a solvent and stirred at room temperature for 30 minutes, then a binder resin, photopolymerizable compound and additives were added thereto and stirred at room temperature for 60 minutes. Then, the pigment dispersion as a colorant was added to the obtained reaction product and stirred at room temperature for 30 minutes. The product was then filtered twice to remove impurities, thereby preparing a photosensitive resin composition (solid content: 11.4% by weight).
  • B-2 Bifunctional photopolymerizable compound 1 represented by the following formula (viscosity: 600 ⁇ 700 cps @25°C, material name: BPA(EO)10DA Bisphenol A (EO)10 Diacrylate, product name: M2100, manufacturer: Miwon Corporation )
  • a photosensitive resin film was formed on the patterned substrate using each photosensitive resin composition according to Reference Examples 1 to 15, and the step difference and S.SNR between the pattern and the resin film were evaluated.
  • the specific evaluation method is as follows.
  • the ⁇ Y (nm) value is the same as the step according to Equation 1 described above.
  • the pattern and resin film level differ depending on the weight ratio of the binder resin/photopolymerizable compound. Specifically, when other conditions, such as the type of binder resin and the type of photopolymerizable compound, are the same, it can be seen that as the weight ratio of binder resin/photopolymerizable compound increases, the level difference between the pattern and the resin film decreases.
  • the pattern and resin film level differ depending on the weight average molecular weight of the binder resin. Specifically, when other conditions such as the weight ratio of binder resin/photopolymerizable compound and the type of photopolymerizable compound are the same, it can be seen that as the molecular weight of the binder increases, the difference between the pattern and the resin film decreases.
  • the pattern and resin film level difference change depending on the addition of the difunctional photopolymerizable compound or the tetrafunctional photopolymerizable compound. Specifically, when other conditions such as the weight ratio of binder resin/photopolymerizable compound, type of binder resin, and type of hexafunctional photopolymerizable compound are the same, the pattern and It can be seen that the resin film level difference is lowered. Furthermore, when adding a bifunctional photopolymerizable compound rather than a tetrafunctional photopolymerizable compound, the step between the pattern and the resin film is further lowered to less than 1350 ⁇ .
  • the pattern and resin film level difference change depending on the type of hexafunctional photopolymerizable compound. Specifically, when other conditions such as the weight ratio of binder resin/photopolymerizable compound, type of binder resin, and type and addition amount of difunctional photopolymerizable compound are the same, the pattern and resin are changed by changing the type of hexafunctional photopolymerizable compound. It can be seen that the level difference is lowered.
  • Photosensitive resin compositions according to Examples 1 to 4 were prepared by mixing the compositions shown in Table 12 below.
  • the photopolymerization initiator was dissolved in a solvent and stirred at room temperature for 30 minutes, then a binder resin, photopolymerizable compound and additives were added thereto and stirred at room temperature for 60 minutes. Then, the pigment dispersion as a colorant was added to the obtained reaction product and stirred at room temperature for 30 minutes. Then, the product was filtered twice to remove impurities, thereby preparing a photosensitive resin composition.
  • Example 1 Example 2
  • Example 3 Example 4 (A) Binder resin A-1 38.5 - - - - A-2 37.8 4.571 5.333 5.333 5.333 A-3 39.3 - - - - A-4 38.8 - - - - (B) Photopolymerizable compound B-1 100 1.152 0.864 0.648 0.432 B-2 100 - - 0.216 0.432 B-3 100 - - - - B-4 100 - - - - - B-5 100 - - - - - B-6 100 - - - - B-7 100 - - - - - Binder resin/photopolymerizable compound weight ratio - 0/100 60/40 70/30 70/30 (C) Photopolymerization initiator C-1 100 0.547 0.547 0.547 0.547 (D) Colorant D-1 18.04 43.234 43.234 43.234 43.234 (E) Solvent E-1 - 14.70
  • Examples 1 to 4 significantly reduced the step between the pattern and the resin film to 1,000 ⁇ or less by comprehensively considering multiple factors.
  • the binder resin/photopolymerizable compound As the weight ratio becomes larger in the range of 60/40 or more, and as the weight average molecular weight of the binder resin decreases closer to 4,000 g/mol in the range of 9,000 g/mol or less, the hexafunctional photopolymerizable compound is necessarily included, but the bifunctional As the photopolymerizable compound is added and the amount added is controlled closer to 50/50, the difference between the pattern and the resin film is significantly lowered to 1,000 ⁇ or less.

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  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Structural Engineering (AREA)
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Abstract

La présente invention concerne une composition de résine photosensible, une couche de résine photosensible fabriquée à l'aide de celle-ci, et un filtre coloré. Spécifiquement, un mode de réalisation concerne une composition de résine photosensible qui comprend : (A) une résine liante ; (B) un composé photopolymérisable ; (C) un colorant ; (D) un initiateur de photopolymérisation ; et (E) un solvant, le rapport pondéral de la résine liante au composé photopolymérisable (résine liante/composé photopolymérisable) étant de 60/40 ou plus, la masse moléculaire moyenne en poids de la résine liante étant de 4000 g/mol à 9000 g/mol, et le composé photopolymérisable étant un composé photopolymérisable hexafonctionnel seul, ou un mélange d'un composé photopolymérisable hexafonctionnel et d'un composé photopolymérisable bifonctionnel.
PCT/KR2023/005404 2022-08-30 2023-04-20 Composition de résine photosensible, couche de résine photosensible fabriquée à l'aide de celle-ci, et filtre coloré Ceased WO2024048893A1 (fr)

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JP2024562918A JP2025514953A (ja) 2022-08-30 2023-04-20 感光性樹脂組成物、これを用いて製造された感光性樹脂膜、およびカラーフィルタ
CN202380041838.2A CN119343634A (zh) 2022-08-30 2023-04-20 感光性树脂组合物、使用其制造的感光性树脂层和滤色器

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KR20190085232A (ko) * 2018-01-10 2019-07-18 동우 화인켐 주식회사 착색 감광성 조성물, 컬러필터 및 촬상 소자
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JP6703104B2 (ja) * 2016-05-31 2020-06-03 富士フイルム株式会社 転写フィルム
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KR101418026B1 (ko) * 2014-02-06 2014-08-08 동우 화인켐 주식회사 열경화성 잉크 조성물
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US20200369810A1 (en) * 2018-02-21 2020-11-26 Fujifilm Corporation Curable composition, cured product, color filter, method for producing color filter, solid imaging element, and image display device

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