CN111123648A - Low-temperature curing type photosensitive resin composition, quantum dot color film and display device - Google Patents

Low-temperature curing type photosensitive resin composition, quantum dot color film and display device Download PDF

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Publication number
CN111123648A
CN111123648A CN201911348338.5A CN201911348338A CN111123648A CN 111123648 A CN111123648 A CN 111123648A CN 201911348338 A CN201911348338 A CN 201911348338A CN 111123648 A CN111123648 A CN 111123648A
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low
quantum dot
resin composition
resin
photosensitive resin
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岳爽
李琳
吴京玮
赵明
王淼
贾刚刚
王雪岚
陆金波
梁珂
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Fuyang Sineva Material Technology Co Ltd
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Fuyang Sineva Material Technology Co Ltd
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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
    • G03F7/027—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
    • 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
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Abstract

The invention belongs to the technical field of display, and particularly relates to a low-temperature curing type photosensitive resin composition, a quantum dot color film and a display device. The low-temperature curable photosensitive resin composition according to the present invention includes a quantum dot and an alkali-soluble resin including a silicone resin having a silane group and at least one additional resin; the weight percentage of the silicone resin is 20-50 wt% relative to the alkali-soluble resin.

Description

Low-temperature curing type photosensitive resin composition, quantum dot color film and display device
Technical Field
The invention belongs to the technical field of display, and particularly relates to a low-temperature curing type photosensitive resin composition, a quantum dot color film and a display device.
Background
The quantum dot photoresist is a photosensitive resin composition prepared by dispersing a quantum dot material in the photoresist instead of a conventional pigment. The quantum dot color film is a quantum dot microstructure which is obtained by using quantum dot photoresist through a photoetching process and is arranged in a pixelization mode. Compared with the traditional color filter, the quantum dot color film can effectively improve the brightness and widen the color gamut range.
By utilizing the color conversion characteristic of the quantum dot color film, a novel QD-OLED display technology combining quantum dots (high color gamut) and OLEDs (high contrast) can be realized. The technology only needs a blue OLED light source, the cost is reduced compared with that of an RGB OLED, the quantum efficiency of red and green quantum dots is effectively improved and is close to 100%, the technology is more energy-saving, the brightness is higher, the color gamut is wider, and the self-luminous characteristic of OLED pixel points is kept.
In order to make the quantum dot color film have better adhesion and chemical resistance, the quantum dot photoresist needs to be subjected to a post-baking process at a high temperature to fully cure the color film. However, the high temperature post-baking process has two problems: firstly, the high temperature can damage the surface ligand structure of the quantum dot material, thereby reducing the stability of the quantum dot material in a color film and causing the deactivation of quantum dots; second, it is difficult to be compatible with OLED display device structures that are not resistant to high temperatures.
Therefore, there is a need for development of a low-temperature curable photosensitive resin composition that can be sufficiently cured under low-temperature post-baking conditions and exhibits good adhesion and chemical resistance.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a low-temperature curing type photosensitive resin composition, a preparation method thereof, a quantum dot color film and a display device.
According to an aspect of the present invention, there is provided a low-temperature curable photosensitive resin composition including quantum dots and an alkali-soluble resin including a silicone resin having a silane group and at least one additional resin; the weight percentage of the silicone resin is 20-50 wt% relative to the alkali-soluble resin.
According to an embodiment of the present invention, the weight percentage of the quantum dots is 3 to 40 wt% and the weight percentage of the alkali-soluble resin is 5 to 40 wt% based on the total weight of the low-temperature curable photosensitive resin composition.
According to one embodiment of the invention, the further resin is selected from acrylic resins, epoxy resins, fluorene resins.
According to one embodiment of the present invention, the silicone resin is selected from at least one of methacryloxypropyltrimethoxysilane, methylvinyldimethoxysilane, dimethoxymethylvinylsilane, methylphenyldimethoxysilane, polyphenylmethylsiloxane.
When the weight percentage of the silicone resin is within this range, the low-temperature curable photosensitive resin composition has excellent low-temperature curability, and the chemical resistance of the resulting film after curing is good. If the organic silicon resin proportion is too low, after the surface of the membrane cured at low temperature is coated with the color photoresist, even if no obvious damage is observed by naked eyes, local damage can be found when a pixel is observed by a microscope. If the silicone resin content exceeds 50 wt%, the luminous efficiency of the quantum dot is affected.
According to one embodiment of the invention, the silicone resin has a weight average molecular weight of no more than 15000 and an acid number of from 50 to 140 mg KOH/g, and the further resin has a weight average molecular weight of no more than 15000 and an acid number of from 50 to 140 mg KOH/g.
The weight average molecular weight and the acid value of the resin influence the developability, and the higher the molecular weight, the smaller the acid value, the longer the development time, so that the soaking time of the quantum dots in a developing solution is increased, and the influence on the luminescent performance of the quantum dots is caused. When the weight average molecular weight and the acid value are within this range, normal development in a quantum dot photoresist lithography process is facilitated.
According to an embodiment of the present invention, the photosensitive resin composition further includes a photopolymerizable monomer, a dispersion resin, scattering particles, a photoinitiator, a leveling agent, and a solvent.
According to an embodiment of the present invention, the weight percentage of the quantum dots is 3 to 40 wt%, the weight percentage of the alkali-soluble resin is 5 to 40 wt%, the weight percentage of the photopolymerizable monomer is 5 to 40 wt%, the weight percentage of the dispersion resin is 1 to 10 wt%, the weight percentage of the scattering particles is 0.01 to 20 wt%, the weight percentage of the photoinitiator is 0.01 to 2 wt%, the weight percentage of the leveling agent is 0.01 to 0.1 wt%, and the weight percentage of the solvent is 10 to 40 wt%, based on the total weight of the low-temperature curable photosensitive resin composition.
According to one embodiment of the present invention, the mass ratio of the photopolymerizable monomer to the alkali-soluble resin is (0.5-2): 1; the mass ratio of the dispersion resin to the alkali-soluble resin is 1: (1-5).
The photopolymerizable monomer and the alkali-soluble resin in the components have an influence on the film-forming property during photocuring, and when the mass ratio of the two is within this range, the film-forming property of the photosensitive resin composition after curing at low temperature is facilitated.
The dispersion resin is mainly used to disperse the scattering particles into a dispersion first, and therefore, the content in the entire system is relatively low.
According to one embodiment of the present invention, the viscosity of the low-temperature curable photosensitive resin composition is 5 to 10 cp.
When the viscosity of the low-temperature curable photosensitive resin composition is within this range, dispersion stability of the quantum dots in the entire system is facilitated.
According to another aspect of the present invention, there is provided a method for preparing a low temperature curable photosensitive resin composition according to the present invention, comprising the steps of:
and mixing and dispersing the components to obtain the low-temperature curing type photosensitive resin composition.
According to one embodiment of the present invention, the method for preparing the low temperature curable photosensitive resin composition comprises the steps of:
s101: mixing and dispersing quantum dots, alkali-soluble resin, a photopolymerizable monomer, a photoinitiator, a flatting agent and a solvent to obtain a first dispersion liquid;
s102: mixing and dispersing the scattering particles and the dispersion resin to obtain a second dispersion liquid;
s103: and mixing and stirring the first dispersion liquid and the second dispersion liquid to obtain the curable photosensitive resin composition.
According to an embodiment of the present invention, in step S102, the mixing and dispersing are performed by a high shear grinding method.
According to another aspect of the invention, a quantum dot color film is provided, and the quantum dot color film comprises the low-temperature curing type photosensitive resin composition.
According to one embodiment of the invention, the thickness of the quantum dot color film is 3-10 μm.
According to another aspect of the present invention, there is provided a method for preparing a quantum dot color film, including the following steps: and preparing the quantum dot color film from the low-temperature curing type photosensitive resin composition by a photoetching patterning process.
According to one embodiment of the invention, the lithographic patterning process includes a post-bake operation, wherein the post-bake temperature does not exceed 100 ℃.
According to one embodiment of the invention, the lithographic patterning process includes spin coating, pre-baking, exposure, development and post-baking.
According to another aspect of the invention, a display device is provided, which includes the quantum dot color film.
The quantum dot photoresist provided by the invention can be fully cured at a lower temperature (85 ℃), the postbaking temperature of a photoetching patterning process is effectively reduced, and the quantum dot photoresist has good adhesion and chemical resistance and can be applied to an OLED display technology.
Drawings
FIG. 1 is a microscopic view of the surface of the low-temperature curable quantum dot color film coated with a color photoresist of example 1;
FIG. 2 is a macroscopic view of the quantum dot color film of comparative example 1 after the surface is coated with a color photoresist;
FIG. 3 is a microscopic view of the quantum dot color film of comparative example 3 after the surface is coated with a color photoresist;
fig. 4 is a microscopic view of the quantum dot color film of comparative example 4 after the surface is coated with a color photoresist.
Detailed Description
The invention provides a low-temperature curing type photosensitive resin composition, a preparation method thereof, a quantum dot color film and a display device.
According to an aspect of the present invention, there is provided a low-temperature curable photosensitive resin composition including quantum dots and an alkali-soluble resin including a silicone resin having a silane group and at least one additional resin; the weight percentage of the silicone resin is 20-50 wt% relative to the alkali-soluble resin.
The quantum dot photoresist provided by the invention comprises organic silicon resin, wherein silane group can be bonded with the photopolymerizable monomer and the other resin in the quantum dot photoresist through silicon-oxygen bond at low temperature to form a structure with more sufficient curing, so that the structure can be fully cured at low temperature (85 ℃), the postbaking temperature of a photoetching patterning process is effectively reduced, and the quantum dot photoresist has good adhesion and chemical resistance and can be applied to OLED display technology.
According to one embodiment of the invention, the alkali-soluble resin comprises a silicone resin having silane groups and one additional resin.
According to an embodiment of the present invention, the weight percentage of the quantum dots is 3 to 40 wt% and the weight percentage of the alkali-soluble resin is 5 to 40 wt% based on the total weight of the low-temperature curable photosensitive resin composition.
According to one embodiment of the present invention, the quantum dots are red light emitting quantum dots or green light emitting quantum dots, that is, red quantum dots or green quantum dots. The quantum dots comprise at least one of II-VIA group compounds, IV-VIA group compounds, III-VA group compounds and I-VIA group compounds. The structure of the quantum dot comprises one of a single-core structure, a core-single-layer shell structure, a core-multi-layer shell structure and an alloy structure.
According to one embodiment of the present invention, the surface of the quantum dot is modified with a ligand so as to be more compatible with a solvent. The ligand of the quantum dot can be selected from polymeric groups containing carboxyl, sulfydryl, amino, double bonds and the like.
According to one embodiment of the invention, the further resin is selected from acrylic resins, epoxy resins, fluorene resins. The acrylic resin may be selected from, for example, acrylic resins, methacrylic resins, derivatives thereof, and the like. The epoxy resin may be selected from, for example, bisphenol a type epoxy resin, bisphenol F type epoxy resin, novolac epoxy resin, and the like. The fluorene resin is a resin having a fluorene ring structure in the skeleton.
According to one embodiment of the present invention, the silicone resin has silane groups, non-limiting examples of which include: methacryloxypropyltrimethoxysilane, methylvinyldimethoxysilane, dimethoxymethylvinylsilane, methylphenyldimethoxysilane, polyphenylmethylsiloxane and the like.
According to an embodiment of the present invention, the weight percentage of the silicone resin with respect to the alkali-soluble resin may be, for example, 20 wt%, 21 wt%, 22 wt%, 23 wt%, 24 wt%, 25 wt%, 27 wt%, 29 wt%, 30 wt%, 32 wt%, 34 wt%, 36 wt%, 38 wt%, 40 wt%, 41 wt%, 42 wt%, 44 wt%, 45 wt%, 46 wt%, 47 wt%, 48 wt%, 49 wt%, 50 wt%, etc.
When the weight percentage of the silicone resin is within this range, the low-temperature curable photosensitive resin composition has excellent low-temperature curability, and the chemical resistance of the resulting film after curing is good. If the organic silicon resin proportion is too low, after the surface of the membrane cured at low temperature is coated with the color photoresist, even if no obvious damage is observed by naked eyes, local damage can be found when a pixel is observed by a microscope. If the silicone resin content exceeds 50 wt%, the luminous efficiency of the quantum dot is affected.
According to one embodiment of the invention, the values of the relevant parameters of each resin constituting the alkali-soluble resin are within the following ranges: the weight average molecular weight is no more than 15000, and the acid value is 50-140KOH mg/g. That is, the silicone resin has a weight average molecular weight of no more than 15000 and an acid number of 50-140KOH mg/g, and the additional resin has a weight average molecular weight of no more than 15000 and an acid number of 50-140KOH mg/g.
The weight average molecular weight and the acid value of the resin influence the developability, and the higher the molecular weight, the smaller the acid value, the longer the development time, so that the soaking time of the quantum dots in a developing solution is increased, and the influence on the luminescent performance of the quantum dots is caused. When the weight average molecular weight and the acid value are within this range, normal development in a quantum dot photoresist lithography process is facilitated.
According to an embodiment of the present invention, the photosensitive resin composition further includes a photopolymerizable monomer, a dispersion resin, scattering particles, a photoinitiator, a leveling agent, and a solvent.
In the present invention, a dispersion resin is used to disperse the scattering particles. The dispersing resin is typically an acrylic resin, having a viscosity in the range of 0.1-2cp and a molecular weight of not more than 7000.
The scattering particles may be TiO2、SiO2、Al2O3Inorganic nano particles, the size of scattering particles is 50-500 nm.
The photopolymerizable monomer may be selected from acrylate monomers, and may be, for example, a monofunctional acrylate monomer, a bifunctional acrylate monomer, a multifunctional acrylate monomer, and the like.
The monofunctional acrylate monomer may be selected from at least one of hydroxyethyl acrylate, hydroxypropyl acrylate, lauryl acrylate, stearyl acrylate, 2-ethylhexyl acrylate, butyl acrylate, ethoxylated cyclohexanol acrylate, isobornyl acrylate, epoxy acrylate, ethyl ethoxyacrylate, neopentyl glycol benzoate acrylate, 2-phenoxyethyl methacrylate, and nonylphenoxy polyethylene glycol acrylate.
The difunctional acrylate monomer may be selected from the group consisting of tricyclo basket for holding earth alkanedimethanol diacrylate, polyethylene glycol (200) diacrylate, polyethylene glycol (400) diacrylate, polyethylene glycol (600) diacrylate, tripropylene glycol diacrylate, dipropylene glycol diacrylate, propylene glycol diacrylate, neopentyl glycol diacrylate, propoxylated (2) neopentyl glycol diacrylate, 1, 3-butanediol diacrylate, at least one of diethylene glycol diacrylate phthalate, tripropylene glycol diacrylate phthalate, ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, 1, 6-hexanediol diacrylate, ethoxylated-1, 6-hexanediol diacrylate, 1, 4-butanediol diacrylate and ethoxylated (4) bisphenol A diacrylate.
The multifunctional acrylate monomer may be at least one selected from the group consisting of isocyanuric acid triacrylate, trimethylolpropane triacrylate, ethylene oxide-modified trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated (3) glycerol triacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, and dipentaerythritol pentaacrylate.
The photopolymerizable monomers in the present invention may also be urethane acrylate oligomers.
The photoinitiator may be selected from benzoin isobutyl ether, benzoin ethyl ether, 2, 4-diethylacetophenone, 2-isopropylacetophenone, diethyl 2,4, 6-trimethylbenzoyl phosphate, 2,4, 6-trimethylbenzoyl diphenylphosphine oxide, 2-phenyl-2, 2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, methyl o-benzoylbenzoate, bis (2,4, 6-trimethylbenzoyl) phenylphosphine oxide, bis (2, 6-dimethoxybenzoyl) - (4 ', 4' -dimethyloctyl-2) phosphine oxide, bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethylpentylphosphine oxide, hydrogen peroxide, hydrogen, 1-hydroxy-cyclohexylphenylketone, phenyldimethyl ketal, 2-hydroxy-2-methylphenylacetone, 2-hydroxy-2-methyl-p-hydroxyethyletherphenylacetone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropylacetone, 4-p-tolylmercaptobenzophenone, 2-methyl-1- (4-methylmercaptophenyl) -2-morpholin-1-one, 2-dimethoxy-phenylketone, 2-isopropylthioxanthone, benzophenone, 2,4, 6-trimethylbenzophenone, 4-methylbenzophenone, 4-phenylbenzophenone, 4' -bis (dimethylamino) benzophenone, 4, 4' -bis (diethylamino) benzophenone, 2-methyl formate benzophenone, 2, 4-diethylthioxanthone, 2-chlorothioxanthone and 2-ethylanthraquinone.
The leveling agent may be selected from an acrylic leveling agent (e.g., BYK358N), a silicon-based leveling agent (e.g., BYK333, BYK354), or a fluorine-based leveling agent (e.g., F563, 361N, 432).
The solvent may be selected from alcohols such as methanol, ethanol, isopropanol, n-butanol, ethylene glycol, propylene glycol, glycerol, etc.; ethers such as ethylene glycol ethyl ether, ethylene glycol butyl ether, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol butyl ether, dipropylene glycol methyl ether; glycol ether acetates such as ethylene glycol ethyl ether acetate, propylene glycol methyl ether acetate; at least one of acetonitrile, dimethyl sulfoxide, dimethylformamide and the like. According to one embodiment of the invention, the solvent is selected from propylene glycol methyl ether acetate.
According to an embodiment of the present invention, the weight percentage of the quantum dots is 3 to 40 wt%, the weight percentage of the alkali-soluble resin is 5 to 40 wt%, the weight percentage of the photopolymerizable monomer is 5 to 40 wt%, the weight percentage of the dispersion resin is 1 to 10 wt%, the weight percentage of the scattering particles is 0.01 to 20 wt%, the weight percentage of the photoinitiator is 0.01 to 2 wt%, the weight percentage of the leveling agent is 0.01 to 0.1 wt%, and the weight percentage of the solvent is 10 to 40 wt%, based on the total weight of the low-temperature curable photosensitive resin composition.
According to one embodiment of the present invention, the mass ratio of the photopolymerizable monomer to the alkali-soluble resin is (0.5-2): 1; the mass ratio of the dispersion resin to the alkali-soluble resin is 1: (1-5).
The photopolymerizable monomer and the alkali-soluble resin in the components have an influence on the film-forming property during photocuring, and when the mass ratio of the two is within this range, the film-forming property of the photosensitive resin composition after curing at low temperature is facilitated.
The dispersion resin is mainly used to disperse the scattering particles into a dispersion first, and therefore, the content in the entire system is relatively low.
According to one embodiment of the present invention, the viscosity of the low-temperature curable photosensitive resin composition is 5 to 10 cp.
When the viscosity of the low-temperature curable photosensitive resin composition is within this range, dispersion stability of the quantum dots in the entire system is facilitated.
According to another aspect of the present invention, there is provided a method for preparing a low temperature curable photosensitive resin composition according to the present invention, comprising the steps of:
and mixing and dispersing the components to obtain the low-temperature curing type photosensitive resin composition.
According to one embodiment of the present invention, the method for preparing the low temperature curable photosensitive resin composition comprises the steps of:
s101: mixing and dispersing quantum dots, alkali-soluble resin, a photopolymerizable monomer, a photoinitiator, a flatting agent and a solvent to obtain a first dispersion liquid;
s102: mixing and dispersing the scattering particles and the dispersion resin to obtain a second dispersion liquid;
s103: and mixing and stirring the first dispersion liquid and the second dispersion liquid to obtain the curable photosensitive resin composition.
According to an embodiment of the present invention, in step S102, the mixing and dispersing are performed by a high shear grinding method.
According to another aspect of the invention, a quantum dot color film is provided, and the quantum dot color film comprises the low-temperature curing type photosensitive resin composition.
According to one embodiment of the invention, the thickness of the quantum dot color film is 3-10 μm.
According to another aspect of the present invention, there is provided a method for preparing a quantum dot color film, including the following steps: and preparing the quantum dot color film from the low-temperature curing type photosensitive resin composition by a photoetching patterning process.
According to one embodiment of the invention, the lithographic patterning process includes a post-bake operation, wherein the post-bake temperature does not exceed 100 ℃.
According to one embodiment of the present invention, the post-baking temperature is, for example, not more than 98 ℃, not more than 97 ℃, not more than 95 ℃, not more than 93 ℃, not more than 92 ℃, not more than 90 ℃, not more than 89 ℃, not more than 88 ℃, not more than 86 ℃, not more than 85 ℃ or the like.
According to one embodiment of the invention, the lithographic patterning process includes spin coating, pre-baking, exposure, development and post-baking.
According to another aspect of the invention, a display device is provided, which includes the quantum dot color film.
The present invention will be further described with reference to the following specific examples.
Preparation of photosensitive resin compositions of examples 1 to 6 and comparative examples 1 to 4
Mixing and dispersing quantum dots, alkali-soluble resin, a photopolymerizable monomer, a photoinitiator, a flatting agent and a solvent to obtain a first dispersion liquid;
mixing and dispersing the scattering particles and the dispersion resin to obtain a second dispersion liquid;
and mixing and stirring the first dispersion liquid and the second dispersion liquid to obtain the curable photosensitive resin composition.
TABLE 1 Components in inventive and comparative examples
Figure BDA0002334017780000071
Figure BDA0002334017780000081
Note: in the present invention, the parts in each of examples and comparative examples are parts by weight, and the weight represented by each 1 part is the same in all of the examples and comparative examples.
A1 methyl vinyl dimethoxy silane, A2 polyphenyl methyl siloxane;
spdd-41, Spdd-16, Spdd-26 and Spdd-36 are all acrylic alkali-soluble resins for Showa electrician;
TRB201 is Kisco's fluorene resin alkali soluble resin;
411 is bisphenol A type epoxy resin;
b1 is isobornyl acrylate, B2 is isocyanuric acid triacrylate, B3 is propylene glycol diacrylate, B4 is pentaerythritol tetraacrylate; (Saduoma)
C1 benzoin ethyl ether, C2: 2, 4-diethylacetophenone, C3: 4-methylbenzophenone, C4: benzoin isobutyl ether; (BASF)
PGMEA: propylene glycol methyl ether acetate;
in examples 1 and 2, the weight ratio of the silicone resin to the alkali-soluble resin was 20%;
in examples 3 and 4, the weight ratio of the silicone resin to the alkali-soluble resin was 30% and 40%, respectively;
in examples 5 and 6, the weight ratio of the silicone resin to the alkali-soluble resin was 20% and 25%, respectively;
comparative examples 1 and 2 contained no silicone resin;
in comparative examples 3 and 4, the weight ratio of the silicone resin to the alkali-soluble resin was 10% and 15%, respectively.
Table 2 shows the weight average molecular weight and acid value of the resins used in examples of the present invention and comparative examples.
TABLE 2 parameter values of resins used in inventive and comparative examples
Spdd-41 A1 A2 TRB201 8900 411 Spdd-16 Spdd-26 Spdd-23
Molecular weight 5200 8500 11000 5300 6100 3400 6600 5800 4500
Acid value 82 158 125 110 135 122 88 80 91
The red and green quantum dots used in the examples and comparative examples are cadmium-free InP quantum dots with half-peak widths of 35nm and 38nm, fluorescence efficiencies of 88% and 85%, respectively, and sizes of less than 10 nm.
Evaluation of chemical resistance of quantum dot color film
(1) Preparation of quantum dot color film
The low-temperature curing type photosensitive resin composition in example 1-2 and the photosensitive resin composition in comparative example 1-4 were respectively spin-coated, pre-baked, exposed, developed and post-baked at 85 ℃ on a glass substrate by controlling the photolithography process to obtain a quantum dot colored film sheet of 3-10 μm.
(2) Performance evaluation of quantum dot color film
Ordinary color photoresist is spin-coated on the quantum dot color membrane, after the solvent is removed by prebaking, the surface state of the membrane is observed by naked eyes, and if pattern wrinkles or falling off occurs, the low-temperature curing property is poor, and the membrane cannot resist chemical contact. And if the surface state is not obviously damaged by visual observation, continuously using the microscope to observe whether the pixel is damaged or not.
Examples 1-6 were prepared by adding 20 wt%, 30 wt%, 40 wt%, 20 wt%, 25 wt% silicone resin, respectively, and after curing at 85 ℃ and surface coating with a color photoresist, the pixels were intact when observed with a microscope (as shown in fig. 1).
In comparative examples 1 and 2, no silicone resin is added, and after the film is cured at 85 ℃ and the surface of the film is coated with a color photoresist, wrinkles on the surface of the film can be seen by naked eyes, and the film is seriously damaged (as shown in figure 2).
Comparative examples 3 and 4, in which only a small amount of silicone resin was added, were observed by naked eyes after curing at 85 ℃ and after coating a color photoresist on the surface, but had damage to the pixel when observed by a microscope (as shown in fig. 3 and 4).
Therefore, in the comparative examples, the surface of the quantum dot color film after post-baking is damaged after spin coating of the common color photoresist, and particularly in comparative examples 1 and 2, the surface damage is serious. This indicates that the film of the comparative example has insufficient post-baking curing, poor adhesion to the substrate, and is easily corroded by a common photoresist to wrinkle and separate from the substrate, and also indicates that the quantum dot color film of the comparative example has poor chemical resistance (common photoresist).
It will be apparent to those skilled in the art that various changes and modifications may be made in the present application without departing from the spirit and scope of the application. Thus, if such modifications and variations of the present application fall within the scope of the claims of the present application and their equivalents, the present application is intended to include such modifications and variations as well.

Claims (10)

1. A low-temperature curable photosensitive resin composition comprising a quantum dot and an alkali-soluble resin comprising a silicone resin having a silane group and at least one additional resin; the weight percentage of the silicone resin is 20-50 wt% relative to the alkali-soluble resin.
2. The low-temperature curable photosensitive resin composition according to claim 1, wherein said another resin is selected from the group consisting of acrylic resins, epoxy resins, fluorene resins; the organic silicon resin is selected from at least one of methacryloxypropyltrimethoxysilane, methyl vinyl dimethoxysilane, dimethoxy methyl vinyl silane, methyl phenyl dimethoxysilane and polyphenyl methyl siloxane.
3. The low-temperature curable photosensitive resin composition according to claim 1, wherein said silicone resin has a weight average molecular weight of no more than 15000 and an acid value of 50 to 140KOH mg/g, and said another resin has a weight average molecular weight of no more than 15000 and an acid value of 50 to 140KOH mg/g.
4. The low-temperature curable photosensitive resin composition according to claim 1, further comprising a photopolymerizable monomer, a dispersing resin, scattering particles, a photoinitiator, a leveling agent, and a solvent.
5. The low-temperature curable photosensitive resin composition of claim 4, wherein the quantum dots are present in an amount of 3 to 40 wt%, the alkali-soluble resin is present in an amount of 5 to 40 wt%, the photopolymerizable monomer is present in an amount of 5 to 40 wt%, the dispersion resin is present in an amount of 1 to 10 wt%, the scattering particles are present in an amount of 0.01 to 20 wt%, the photoinitiator is present in an amount of 0.01 to 2 wt%, the leveling agent is present in an amount of 0.01 to 0.1 wt%, and the solvent is present in an amount of 10 to 40 wt%, based on the total weight of the low-temperature curable photosensitive resin composition.
6. The low-temperature-curable photosensitive resin composition according to claim 1, wherein the mass ratio of the photopolymerizable monomer to the alkali-soluble resin is (0.5-2): 1; the mass ratio of the dispersion resin to the alkali-soluble resin is 1: (1-5).
7. A quantum dot color film, wherein the quantum dot color film comprises the low-temperature curable photosensitive resin composition according to any one of claims 1 to 6.
8. The method for preparing the quantum dot color film of claim 7, comprising the following steps: and preparing the quantum dot color film from the low-temperature curing type photosensitive resin composition by a photoetching patterning process.
9. The method of claim 8, wherein the photolithographic patterning process comprises a post-bake operation, wherein the post-bake temperature does not exceed 100 ℃.
10. A display device comprising the quantum dot color film of claim 7.
CN201911348338.5A 2019-12-24 2019-12-24 Low-temperature curing type photosensitive resin composition, quantum dot color film and display device Pending CN111123648A (en)

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Application publication date: 20200508