CN105504120B - Bisphenol fluorene acrylic resin and preparation method thereof, quantum dot-colored photosensitive resin composition and preparation method and application thereof - Google Patents
Bisphenol fluorene acrylic resin and preparation method thereof, quantum dot-colored photosensitive resin composition and preparation method and application thereof Download PDFInfo
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- CN105504120B CN105504120B CN201510861308.XA CN201510861308A CN105504120B CN 105504120 B CN105504120 B CN 105504120B CN 201510861308 A CN201510861308 A CN 201510861308A CN 105504120 B CN105504120 B CN 105504120B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F122/10—Esters
- C08F122/12—Esters of phenols or saturated alcohols
- C08F122/20—Esters containing oxygen in addition to the carboxy oxygen
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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Abstract
The invention discloses bisphenol fluorene acrylic resin and a preparation method thereof, and a quantum dot-colored photosensitive resin composition and a preparation method and application thereof. The bisphenol fluorene acrylic resin has the following chemical structural formula (1). The quantum dot color photosensitive resin composition comprises the following components in parts by weight: 20-50 parts of subpixel coloring agent, 40-90 parts of grinding resin composition, 5-20 parts of bisphenol fluorene acrylic resin, 10-20 parts of vinyl light curing resin, 0.1-0.5 part of photoinitiator, 0.1-1 part of active assistant and 30-50 parts of organic solvent. The bisphenol fluorene acrylic resin is used for preparing the quantum dot color photosensitive resin composition, and the quantum dot color photosensitive resin composition is used for manufacturing a color filter of a pixel below 10um, so that the color saturation of the filter is increased, and the manufacturing process is simplified.
Description
Technical field
The present invention relates to photoelectric material, nanocomposite and fine semiconductor electronics manufacture fields, and in particular to one
Kind bisphenol fluorene class acrylic resin and preparation method thereof, quantum dot-color photosensitive resin compositions and its preparation method and application.
Background technology
There are many ways to processing the devices such as colored filter using colourama resist, technology primarily now only includes face
Expect dispersion method, print process, three kinds of ink-jet method.Wherein, pigment dispersion method is that organic/inorganic pigment is dispersed in resin solution,
To have coloured photoresist again to be coated on glass/PET/ metal substrates；Using exposure, development etc. after photoetching processes just
The color layer of colored filter is can be made into, fine with technique, light resistance, contrast, color saturation be relatively high and property
The advantages that capable of stablizing.
Colored filter is the key part and component that colorization is capable of in liquid crystal display, use colourama resist manufacturing technology and
Quality has vital influence to the performance of the high chroma of liquid crystal display and high contrast.With the development of smart mobile phone,
Colored filter will become most important device in liquid-crystal apparatus -- and On-cell the or In-cell standards of itself and touch screen will collect
As a device.
Above-mentioned requirements are answered, to realize more rich colour gamut and more high brightness, are making pattern and pattern of pixels narrow as possible
After technique reaches the 3um limit, needing to introduce new material or part-solutions can just further increase.Quantum dot (quantum
Dot) it is one of feasible material.
Chinese patent application CN104536078A discloses application of the quantum dot film in TFT-LCD device backlights, can be with
The brightness of backlight is being improved to a certain degree, but is the failure to increase the color saturation of liquid crystal device or even excessively high white light
It is also easy to lead to color distortion.And Chinese patent application CN104793392A disclose chromatic photoresist dosage form at pixel layer on it is each
One layer of quantum dot pixel is made, this method increases three layers of alignment process in the fabrication process so that the pixel of entire optical filter
The process that manufacturing process processing procedure increases one times considerably increases the risk of yield of devices decline.In addition, patent document
The patents such as CN201210448399.0 disclose a kind of colorized optical filtering chip technology that quantum dot is directly fabricated to sub-pixel, but not
It can illustrate how quanta point material is fabricated to pixel pattern.
To adapt to the performance requirement that liquid crystal display colour constantly upgrades, except needing to be made fine in addition to pigment dispersion, optimization is high
Molecule is prepared to make the colored filter of 10um or less pixels, can also be compounded in quantum dot in colourama resist, and
Use the blue-ray LED backlight of 410-450nm wavelength.
Invention content
For overcome the deficiencies in the prior art, the purpose of the present invention is to provide a kind of bisphenol fluorene class acrylic resins, should
Bisphenol fluorene class acrylic resin is used to prepare quantum dot color photosensitive resin compositions, reaches control with the mutual cooperation of other resins
The purpose of the performance of quantum dot color photosensitive resin.
The present invention also provides a kind of preparation methods of bisphenol fluorene class acrylic resin, are obtained by this method and are suitable for this hair
Bright bisphenol fluorene class acrylic resin.
Third object of the present invention is to provide a kind of quantum dot color photosensitive resin compositions, the composition quantum dot
It is compounded in colourama resist, the colored filter for making 10um or less pixels, increases the color saturation of optical filter, simplify
Manufacture craft.
Fourth object of the present invention is the quantum dot color photosensitive resin compositions of the present invention making colored filter
Mating plate, and the quantum dot color photosensitive resin compositions of the present invention are used on glass substrate/PET in manufacture pattern.
To achieve the above object, scheme of the present invention is as follows：
A kind of bisphenol fluorene class acrylic resin, the bisphenol fluorene class acrylic resin have following chemical structural formula (1)；Its
In, n=10-230；R1And R3Indicate CH2；R2And R4Indicate OH；X and W are indicated respectivelyA indicates H or C1-C3Alkane
Base
A kind of preparation method of bisphenol fluorene class acrylic resin, the preparation method include the following steps：
(a) synthetic intermediate：It is generated by the monomer and acrylic compounds ring-opening polymerization that are indicated with structural formula (2)
The compound that structural formula (3) indicates；
(b) synthetic product：Continue to be added dropwise in acrylic compounds to the intermediate of structure above (3) under a nitrogen,
React generating structure formula (1)；
(c) product postprocessing：By a chromatography board monitoring, when the intermediate reaction of structural formula (3) is complete, while hot by product
It is transferred to round-bottomed flask to be purified, obtains off-white powder resin, it is dry, that is, it completes.
Specifically, in said program, the acrylic compounds are methacrylic acid, ethylacrylic acid, acrylic acid, third
Olefin(e) acid benzyl ester, styrene, methyl methacrylate, butyl methacrylate, isobornyl methacrylate, methacrylic acid contracting
Water glyceride, methacrylic acid tricyclic [5.2.1.02,6] decyl- 8- base esters, hydroxyethyl methacrylate, hydroxyl butyl propyleneglycol acid esters
In one kind.
Further embodiment, in above-mentioned preparation method, step (a) prepares comprising the concrete steps that for intermediate：According to structural formula
(2) molar ratio of the monomer and acrylic compounds that indicate is 1:The ratio of (2-4), in the monomer list that structural formula (2) indicates
Acrylic compounds are added in body, then addition accounts for the monomer and the total matter of acrylic compounds that structural formula (2) indicates successively
1% tetramethyl ammonium chloride is measured, 0.5% phenol leads to nitrogen protection at 90 DEG C, 130 DEG C of continuation are heated to after 30min dissolvings completely
It reacts, acid value measuring in reaction process, in solution acid value<Stop reacting after 2.0mg, is evaporated under reduced pressure, obtains intermediate compound
Object.
A kind of quantum dot color photosensitive resin compositions are prepared by following raw material in parts by weight：
20-50 parts of sub-pixel rendering agent；
40-90 parts of grind resin composition；
5-20 parts of bisphenol fluorene class acrylic resin of the present invention；
10-20 parts of vinyl light-cured resin；
0.1-0.5 parts of photoinitiator；
0.1-1 parts of coagent；
30-50 parts of organic solvent.
Further embodiment, in above-mentioned preparation method, the sub-pixel rendering agent is by red light quantum point material, green quantum
At least one of point material, blue light quantum point material quanta point material and the organic pigment group with the quanta point material corresponding color
At wherein the mass ratio of quanta point material and organic pigment is 1：(5-10).
Further embodiment, in above-mentioned preparation method, the grind resin composition by structural formula (4) oligomeric resin,
Hyper-dispersant and solvent composition；Wherein, in parts by weight respectively oligomeric resin (in patent application CN201510520207.6
It is middle to disclose specific structure and the preparation method) 1-5 parts, 1-5 parts of hyper-dispersant, 40-80 parts of solvent；
A kind of preparation method of quantum dot color photosensitive resin compositions, the preparation method include the following steps：
A nano dye mill base) is prepared：The granules of pigments of subpixel colors quanta point material and difference corresponding color is existed
Organic solvent is added in the sand mill of 0.1mm zirconium balls and carries out wet grinding, oligomeric resin compositions conduct is added in process of lapping
Dispersion mill base is made in stable resin；
B photosensitive liquid) is prepared：By formula ratio by bisphenol fluorene class acrylic resin of the present invention, vinyl photocuring tree
Fat, photoinitiator, coagent, polar organic solvent mixing are filtered after being dispersed into solution, obtain photosensitive liquid；
C quantum stippling coloured light photosensitive resin composition) is prepared：By step A) in dispersion mill base and step B) photosensitive liquid is mixed
It closes, and finally adds organic solvent adjustment viscosity, disperseed in dispersion machine, after filtering.
A kind of quantum dot color filter, is made by the following method：
S1：The black matrix of 1.5-3 μm of line spoke width of black photoresist formation is used on the glass substrate；
S2：Black matrix" surface covers quantum dot color photosensitive resin compositions of the present invention and forms first layer coloured silk film,
Again first layer pixel is formed by the masking of contraposition mask, partial exposure, development, cure step successively；
S3：In the second layer that the first pixel layer surface is formed with quantum dot color photosensitive resin compositions of the present invention
Pixel and third layer pixel, the wherein subpixel colors in quantum dot color photosensitive resin compositions used by second layer pixel
Sub-pixel rendering agent is made of green light quantum point material and green organic pigment, and quantum dot used by third layer pixel is colored
Subpixel colors sub-pixel rendering agent in photosensitive resin composition is made of blue quanta point material with blue organic pigment；
S4：Finally encapsulate to form colored filter using Over CoatingII photoresists.
A method of it manufacturing pattern on glass substrate/PET, includes the following steps：
1) substrate is fixed：Substrate is adhered to using vacuum and is fixed；
2) photoresist layer is made：Quantum dot color photosensitive resin of the present invention is coated in the substrate of above-mentioned 1) step
Composition forms 2-3 μm of colorful film of first layer using vacuum bakeout；
3) pixel pattern is made：In above-mentioned steps 2) colorful film on using mask masking, UV exposure, development, hardening
Step forms pattern on mask plate.
Compared with prior art, the beneficial effects of the present invention are：
It is formulated 1. the bisphenol fluorene class acrylic resin of the present invention is added in the formula of compound photoresist, with other
Highly compatible between component can adjust the polarity and acid-base balance being entirely formulated, to the matched in terms of polarity, and
The fine lines of 3-5um can be achieved under yellow light processing procedure；
2. organic face is added in sub-pixel quanta point material in quantum dot color photosensitive resin compositions of the present invention
Expect pigment, by can be fully dispersed in the grinding wet processes of mill base and keeping stable, there is lower viscosity, obtain
The viscosity of quantum dot color photosensitive resin compositions is less than 5mPa.s (23 DEG C/50rpm)；Rheology r values 0.93~1.05 it
Between, when being applied to make optical filter, not only increases the color saturation of optical filter, also simplify technique；
3. fine lines can be produced using quantum dot color photosensitive resin compositions of the present invention, it can be achieved that
NTSC color gamut area is increased to 98% or more, good stably dispersing by high brightness, high contrast and high color reproduction effect
Property and the pixel unit morphology controllable of making.
Invention is further described in detail with reference to the accompanying drawings and detailed description.
Description of the drawings
Fig. 1 is the gamut area of quantum dot color photosensitive resin compositions using the present invention；
Fig. 2 is quantum dot-chromatic photoresist lines for making on a glass substrate using photoetching process；In metallographic microscope
With 5000 times of most thin 3.1um width lines measured of joint amplification under CCD；
Fig. 3 is quantum dot-chromatic photoresist lines for being made on PET substrates using photoetching process；In metallographic microscope and
The curve pattern of 5000 times of observations of joint amplification under CCD；
Fig. 4 is quantum dot-chromatic photoresist regulation pattern for being made on PET substrates using photoetching process；In metallography microscope
Combine 5000 times of precision observed of amplification and pattern under mirror and CCD.
Specific implementation mode
A kind of bisphenol fluorene class acrylic resin, the bisphenol fluorene class acrylic resin have following chemical structural formula (1)；Its
In, n=10-230；R1And R3Indicate CH2；R2And R4Indicate OH；X and W are indicated respectivelyA indicates H or C1-C3Alkane
Base
A kind of preparation method of bisphenol fluorene class acrylic resin, the preparation method include the following steps：
(a) synthetic intermediate：It is generated by the monomer and acrylic compounds ring-opening polymerization that are indicated with structural formula (2)
The compound that structural formula (3) indicates；
(b) synthetic product：Continue to be added dropwise in acrylic compounds to the intermediate of structure above (3) under a nitrogen,
React generating structure formula (1)；
(c) product postprocessing：By a chromatography board monitoring, when the intermediate reaction of structural formula (3) is complete, while hot by product
It is transferred to round-bottomed flask to be purified, obtains off-white powder resin, it is dry, that is, it completes.
Specifically, in said program, the acrylic compounds are methacrylic acid, ethylacrylic acid, acrylic acid, third
Olefin(e) acid benzyl ester, styrene, methyl methacrylate, butyl methacrylate, isobornyl methacrylate, methacrylic acid contracting
Water glyceride, methacrylic acid tricyclic [5.2.1.02,6] decyl- 8- base esters, hydroxyethyl methacrylate, hydroxyl butyl propyleneglycol acid esters
In one kind.
Further embodiment, in above-mentioned preparation method, step (a) prepares comprising the concrete steps that for intermediate：According to structural formula
(2) molar ratio of the monomer and acrylic compounds that indicate is 1:The ratio of (2-4), in the monomer list that structural formula (2) indicates
Acrylic compounds are added in body, then addition accounts for the monomer and the total matter of acrylic compounds that structural formula (2) indicates successively
1% tetramethyl ammonium chloride is measured, 0.5% phenol leads to nitrogen protection at 90 DEG C, 130 DEG C of continuation are heated to after 30min dissolvings completely
It reacts, acid value measuring in reaction process, in solution acid value<Stop reacting after 2.0mg, is evaporated under reduced pressure, obtains intermediate compound
Object.
A kind of quantum dot color photosensitive resin compositions are prepared by following raw material in parts by weight：
20-50 parts of sub-pixel rendering agent；
40-90 parts of grind resin composition；
5-20 parts of bisphenol fluorene class acrylic resin of the present invention；
10-20 parts of vinyl light-cured resin；
0.1-0.5 parts of photoinitiator；
0.1-1 parts of coagent；
30-50 parts of organic solvent.
Further embodiment, in above-mentioned preparation method, the sub-pixel rendering agent is by red light quantum point material, green quantum
At least one of point material, blue light quantum point material quanta point material and the organic pigment group with the quanta point material corresponding color
At wherein the mass ratio of quanta point material and organic pigment is 1：(5-10).It is since the pixel of colored filter is constituted substantially
It is arranged by red, green, blue three primary color sub-pixels and is separated by black matrix"；Therefore, in the present invention by launch wavelength in 610-
Red, the orange quanta point material of 640nm ranges is mixed as red light quantum point material with organic red pigment as red son
Pixel shader agent；By launch wavelength in the cyan of 500-580nm ranges, green, yellow quanta point material as green light quantum point
Material mixes with green and yellow organic pigment and is used as yellow sub-pixel colorant；By launch wavelength in 430-480nm ranges
Purple and blue quanta point material are mixed into blue subpixels and as blue light quantum point material and blue and purple organic pigment
Toner.
The test and calculating of the saturation degree be according to colorimetry CIE-XYZ tristimulus values system come, wherein：
The data can be respectively acquired by instrument such as the red, green, blue in attached drawing 1, green four vertex：It is i.e. of the present invention
Colors quantum dot-photoresist composite material chromaticity coordinates value, use formulaWithObtain x, y
(chromaticity coordinates) and Y (brightness) value；And then further calculate out the gamut area reference NTSC standard net value that each colorant surrounds；Its
The calculating formula of middle white balance point (White Balance) is as follows：
N=(YR+YG+YB+YC)+(xR·YR/yR+xG·YG/yG+xB·YB/yB+xC·YC/yC)
Wherein, R, G, B, C indicate four tops red (Red), green (Green), blue (Blue), green (Cyan) of Figure of abstract
Point.
Red sub-pixel colorant can be selected from but not limited to the nanometers such as InP/ZnS, CdSe/ZnS, MnZnS and its ligand
It a kind of in the red light quantum point of size and is formed with a kind of in CI PR177, CI No. PR254 organic red pigments, it is red
The weight ratio of light quanta point material and organic red pigment is 1：(5：10), preferred ratio is 1：(7-10).
Green sub-pixels colorant can be selected from but not limited to InP/ZnS, CdSe/ZnS, CuZnS/ZnS and its ligand etc.
In the yellow light and green light quantum point material of specific nano-scale one kind with CI PG36, CI PG58, CI PG59, CI PY138,
A kind of composition in the equal greens of CI PY150 and yellow organic pigment, yellow light and green light quantum point material and green and yellow have
The weight ratio of machine pigment is 1：(5：10), preferred ratio is 1：(7-10).
Blue subpixels colorant can be selected from but not limited to the specific nanometer rulers such as ZnSe/ZnS, CdS/ZnS and its ligand
Very little blue light and purple light quanta point material and CI PB15：6、CI PB15：4, the blues such as CI PV19, CI PV23, CI PV39
It is formed with purple organic pigment, blue light and purple light quanta point material and blue and purple organic pigment weight ratio are 1：
(5：10), preferred ratio is 1：(7-10).
Further embodiment, in above-mentioned preparation method, the grind resin composition by structural formula (4) oligomeric resin,
Hyper-dispersant and solvent composition；Wherein, respectively oligomeric resin (in patent application CN201510520207.6 in parts by weight
Disclose specific structure and preparation method) 1-5 parts, 1-5 parts of hyper-dispersant, 40-80 parts of solvent；
In structural formula (4), n1=2-40, n2=20-180；R1 and R2 indicates methyl or hydrogen atom；Y is expressed as unsaturated virtue
Alkyl or cychc hydrocarbon；Z indicates methoxyl group polyester alkyl, alkoxy straight-chain alkyl, furans, hexamethylene substituted hydrocarbon radical or benzene
One kind in methyl, phenethyl aryl.
Specifically, further, the group that Y of the present invention is indicated is phenyl, aminomethyl phenyl, 3,5-dimethylphenyl, front three
Base phenyl, ethylphenyl, isopropyl phenyl, butyl phenyl, hydroxy phenyl, methoxyphenyl, acetoxyl group phenyl, butyl phenyl ether
One kind in base, chlorophenyl, bromo phenyl, dichloro- phenyl, chloromethyl phenyl；The group that Z is indicated is methoxyl group polyester alkane
One kind in the groups such as alkyl, alkoxy straight-chain alkyl, furans, hexamethylene substituted hydrocarbon radical, benzyl, phenethyl aryl.
The preparation method of above-mentioned oligomeric resin includes the following steps：
(a) synthetic intermediate：The monomer containing Y group and formula (6) or structure indicated by following structural formula (5)
One kind in two kinds of monomers that formula (7) indicates is added under the action of radical initiator in the solvent containing chain-transferring agent,
In a nitrogen atmosphere, copolymer intermediate of the radical reaction synthesis with following structural formula (8), the wherein list of structural formula (5)
Body is 1.3 with the molar ratio of the monomer of structural formula (6) or the monomer of structural formula (7)：1；
(b) synthetic product：Above-mentioned reaction is monitored by HPLC, low in the concentration of structural formula (6) or the monomer of structural formula (7)
After 5%, by the compound of structural formula (9) in the copolymerization intermediate for being added drop-wise to structure above (8) under nitrogen is divided into, and
Add herein plus radical initiator prepares the product with formula (4), wherein the copolymerization of the compound and formula (8) for the formula (9) being added dropwise
The molar ratio of intermediate is 1.2：1.
Further, above-mentioned preparation method further includes the steps that (c) product postprocessing after step (b)：Pass through HPLC
Product is transferred to round-bottomed flask, rotary evaporation to sticky glue by monitoring while hot after the concentration of the monomer containing formula (6) is less than 5%
Body；Then absolute ethyl alcohol is added into round-bottomed flask, which is transferred to beaker, room temperature magnetic by 65 DEG C of heating magnetic agitation dissolvings
Power is added with stirring pure water, there is white colloidal precipitation；It is filtered using Buchner funnel plus filter paper, obtains off-white powder resin, turned
Move to drying box drying；Resin after drying is redissolved using hexamethylene, constant pressure funnel is added, instillation fills pure water
In beaker, while magnetic agitation；It filters, obtains off-white powder resin, be transferred in drying box dry, calculated yield of weighing.
The hyper-dispersant is non-ionic dispersing agent, the commercially available quotient for mainly having following trade name that can specifically illustrate
Product：EFKA-4060、EFKA-4080、EFKA-4043、EFKA-4047、Disperbyk-2000、Disperbyk-2001、
Disperbyk-161--167、Disperbyk-2050、Disperbyk-2100、Disperbyk-2020、Disperbyk-
333、Solsperse28000、Solsperse24000、Solsperse5000、Solsperse22000、
Solsperse32500、Solsperse38500。
Specifically, the solvent is one kind in dichloromethane, chloroform, toluene, dimethylbenzene.
Specifically, vinyl light-cured resin hexanediyl ester (HDDA) of the present invention, trihydroxy methyl
Propane triacrylate (TMPTA), dipropylene glycol diacrylate (DPGDA), pentaerythritol triacrylate (PETA), season penta
One or more of six acrylate of tetrol, five acrylate of pentaerythrite, pentaerythritol triacrylate etc. one
Meaning is than mixing.
Specifically, coagent of the present invention is levelling agent and/or coupling agent, wherein levelling agent is selected from but simultaneously
It is not limited to polyether-modified dimethyl silicone polymer solution, polyester modification dimethyl silicone polymer solution, Siloxane-Oxyalkylene Copolymers
The poly- methyl alkyl siloxane solution of solution, polyester modification, polyether-modified dimethyl silicone polymer solution, polyether-modified poly dimethyl
One or more of siloxane solution, polyacrylate solution, fluorocarbon copolymer solution mix；The choosing of the coupling agent
From but be not limited to N '-β '-aminoethyls-N- β-aminoethyl-γ-aminopropyltriethoxy dimethoxysilanes, N '-β '-aminoethyl-N- β-
Aminoethyl-γ-aminopropyltriethoxy dimethoxysilane, N '-β '-aminoethyls-N- β-aminoethyl-γ-aminopropyltriethoxy diethoxies
Base silane, N '-β '-aminoethyls-N- β-aminoethyl-γ-aminopropyltrimethoxysilane, N '-β '-aminoethyls-N- β-aminoethyl-
Gamma-aminopropyl-triethoxy-silane and N '-β '-aminoethyls-N- β-aminoethyl-α-aminomethyl triethoxysilicanes, γ-cyclohexylamine third
In ethyl triethoxy silicane alkane and methyl, γ-ring amine propyldimethoxy-silane, γ-chloropropyl triethoxysilane (γ 2)
One or more mixing.
Specifically, organic solvent of the present invention is moderately polar organic solvent, it can select but be not limited to first
Ethyl ketone, ethyl cellosolve, glycol dimethyl ether, ethylene glycol diethyl ether, Propylene Glycol Dimethyl Ether, diethylene glycol dimethyl ether, 2- ethoxies
Base propyl alcohol, 2- methoxypropanols, 3- methoxybutanols, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene-glycol ethyl ether second
One or more of acid esters, butyl acetate mix.
A kind of preparation method of quantum dot color photosensitive resin compositions, the preparation method include the following steps：
A nano dye mill base) is prepared：By quanta point material and the granules of pigments of difference corresponding color in 0.1mm zirconium balls
Organic solvent is added in sand mill and carries out wet grinding, addition oligomeric resin compositions are as stable resin, system in process of lapping
It must disperse mill base；
B photosensitive liquid) is prepared：By formula ratio by bisphenol fluorene class acrylic resin of the present invention, vinyl photocuring tree
Fat, photoinitiator, coagent, polar organic solvent mixing are filtered after being dispersed into solution, obtain photosensitive liquid；
C quantum stippling coloured light photosensitive resin composition) is prepared：By step A) in dispersion mill base and step B) photosensitive liquid is mixed
It closes, and finally adds organic solvent adjustment viscosity, disperseed in dispersion machine, after filtering.
A kind of quantum dot color filter, is made by the following method：
S1：The black matrix of 1.5-3 μm of line spoke width of black photoresist formation is used on the glass substrate；
S2：Black matrix" surface covers quantum dot color photosensitive resin compositions of the present invention and forms first layer coloured silk film,
Again first layer pixel is formed by the masking of contraposition mask, partial exposure, development, cure step successively；
S3：In the second layer picture that the first pixel layer surface quantum dot color photosensitive resin compositions of the present invention are formed
Element and third layer pixel, subpixel colors wherein in quantum dot color photosensitive resin compositions used by second layer pixel
Pixel shader agent is made of green light quantum point material and green organic pigment, quantum dot colourama used by third layer pixel
Subpixel colors sub-pixel rendering agent in photosensitive resin composition is made of blue quanta point material with blue organic pigment；
S4：Finally encapsulate to form colored filter using Over CoatingII photoresists.
A method of it manufacturing pattern on glass substrate/PET, includes the following steps：
1) substrate is fixed：Substrate is adhered to using vacuum and is fixed；
2) photoresist layer is made：Quantum dot color photosensitive resin of the present invention is coated in the substrate of above-mentioned 1) step
Composition forms 2-3 μm of colorful film of first layer using vacuum bakeout；
3) pixel pattern is made：In above-mentioned steps 2) colorful film on using mask masking, UV exposure, development, hardening
Step forms pattern on mask plate.
It is specific embodiment of the present invention below, involved reagent can be bought by market in the following embodiments
Mode obtains.
Embodiment 1
Synthesis of oligonucleotides resin, preparation method are as follows：
1) synthetic intermediate：N-phenylmaleimide is selected, according to the mass ratio 1 with solvent：2 ratios make solvent with EEP
It dissolves by heating, the compound of solution and structural formula (7) is raw material, according to the chemical combination of N-phenylmaleimide and structural formula (7)
The molar ratio of object is 1.3：In 1 input three-necked flask；It is 110 DEG C that reaction temperature, which is arranged, mechanical agitation 305rpm/min；Input is rubbed
Your amount is the azodiisobutyronitrile initiator of the mole 1% of structural formula (7) compound, and mole is structural formula (7) compound
2% chain-transferring agent of mole, three thioesters and quality be 6 times of structural formula (7) compound quality PGMEA solvents；In nitrogen
Under protection, condensing reflux reaction；
2) synthesis of oligonucleotides resin：After the concentration that HPLC monitors structural formula (7) compound is less than 5%, temperature is reduced
It is 1.2 according to the compound initial molar ratio of formula structure (7) to 90 DEG C, rotating speed 180rpm/min：Formula is added in 1 ratio
(10) compound；
And it is structural formula (4) to supplement azodiisobutyronitrile initiator and chain-transferring agent chloroiodomethane, initiator magnitude of recruitment
Compound initial molar amount 0.3%, chain-transferring agent be compound initial molar amount that magnitude of recruitment is structural formula (4)
0.3%, the compound quality ratio of quality and structural formula (10) is 2：1 solvent is in constant pressure funnel；In a manner of dropwise addition
Be added in three-necked flask in 15min, the reaction was continued to formula (10) compound concentration less than 5% after, stop reaction；
3) it post-processes：Product is produced while hot and is evaporated under reduced pressure to thick gel, then PGMEA quantity of solvent before use
The absolute ethyl alcohol of 2 times of volumes, 65 DEG C of heating for dissolving, 4 times of volumes of PGMEA amounts is pure before which is added with stirring
Water has white colloidal precipitation；Off-white powder resin is obtained using suction method, is transferred to 120 DEG C of dry 5Hr in drying box.It will
Resin after drying is dissolved using the hexamethylene of 2 times of volumes of PGMEA amounts before being added at 50 DEG C, with the method 30min of dropwise addition
It instills before filling addition in the beaker of the pure water of 4 times of volumes of PGMEA amounts, while stirring 2hr；It filters, obtains milky white again
Color powdex is transferred to 120 DEG C of dry 8Hr, calculated yield of weighing in drying box and obtains oligomeric resin I.
Embodiment 2
A kind of oligomeric resin, preparation method are as follows：
1) synthetic intermediate：Select the following compound of structural formula (11)
It is 1 according to EEP solvent quality ratios：The chemical combination that solution and structural formula (7) indicate made of 2 ratio dissolves by heating
Object is raw material, is 1.3 according to molar ratio：In 1 input three-necked flask；It is 120 DEG C that reaction temperature, which is arranged, mechanical agitation 380rpm/
min；Successively input account for structural formula (7) compound molal quantity 1% azodiisobutyronitrile as initiator, account for structural formula (7)
Compound molal quantity 2% Sodium Allyl Sulfonate as chain-transferring agent, 6 times of the compound by weight that weight is structural formula (7)
PGMEA is as solvent；Under nitrogen protection, condensing reflux reacts；
2) synthesis of oligonucleotides resin：After the concentration that HPLC monitors the compound of formula (7) is less than 5%, reduce the temperature to
90 DEG C, rotating speed 220rpm/min is controlled, is 1.2 according to the compound initial molar ratio of formula (7)：1 ratio is by structural formula
(12) compound, account for formula (11) compound molal quantity 0.3% azodiisobutyronitrile initiator, account for the compounds of formula (11)
The chloroiodomethane chain-transferring agent of molal quantity 0.3%,
And with the compound quality ratio of formula (12) it is 2:1 EEP solvents are added to constant pressure funnel；With the side of dropwise addition
Formula is added in 15min in three-necked flask, the reaction was continued to HPLC monitor formula (12) compound concentration less than 5% it
Afterwards, stop reaction；
3) it post-processes：It is handled by the step 3) of embodiment 1, obtains oligomeric resin II.
Embodiment 3
A kind of bisphenol fluorene class acrylic resin, preparation method are as follows：
1) synthetic intermediate：The monomer indicated by following structural formula (2)
Middle addition mol ratios are 1：4 methacrylic acid monomer, and 1% tetramethyl according to two kinds of monomer gross mass parts
Ammonium chloride, 0.5% phenol.Lead to nitrogen protection at 90 DEG C, is heated to 130 DEG C after 30min dissolvings completely the reaction was continued 15Hr；It is above-mentioned
It reacts during heating stirring by acid value measuring, in solution<After 2.0mg, it is evaporated under reduced pressure out the chemical combination of formula (3) expression
Object；
2) synthesis of oligonucleotides resin：Constant pressure funnel is used under a nitrogen, is added drop-wise to containing acrylic acid, acrylic acid after 1Hr
(molar ratio of four kinds of monomers is 3 for benzyl ester, styrene, glycidyl methacrylate：3：1：1.5) in four-hole boiling flask；
And 0.3% azodiisobutyronitrile initiator of four kinds of monomer gross mass parts is added, 0.3% chloroiodomethane chain-transferring agent,
150% EEP solvents.Pre-polymerization temperature is 70 DEG C, is added in the four-hole boiling flask in 15min in a manner of dropwise addition, and temperature is increased
To 100 DEG C of the reaction was continued 4Hr；
3) it post-processes：Product is transferred to circle while hot when the monomer reaction containing formula (3) is complete soon by a chromatography board monitoring
Bottom flask, rotary evaporation to thick gel；Then absolute ethyl alcohol is added into round-bottomed flask, 65 DEG C of heating magnetic agitations dissolve,
The solution is transferred to beaker, pure water is added under room temperature magnetic agitation, there is white colloidal precipitation；It is taken out using Buchner funnel plus filter paper
Filter, obtains off-white powder resin, is transferred to drying box drying；Resin after drying is redissolved using hexamethylene, is added permanent
Dropping funel is pressed, is instilled in the beaker for filling pure water, while magnetic agitation；It filters, obtains off-white powder resin, be transferred to dry
Dry in dry case, calculated yield of weighing obtains bisphenol fluorene class acrylic resin I.
Embodiment 4
A kind of bisphenol fluorene class acrylic resin, preparation method are as follows：
1) synthetic intermediate：The monomer indicated by following structural formula (2)
Middle addition mol ratios are 1：2.5 methacrylic acid monomer, and 1% tetramethyl according to two kinds of monomer gross mass parts
Ammonium chloride, 0.5% phenol.Lead to nitrogen protection at 90 DEG C, is heated to 130 DEG C after 30min dissolvings completely the reaction was continued 15Hr.On
Reaction is stated during heating stirring by acid value measuring, in solution<After 2.0mg, it is evaporated under reduced pressure out the chemical combination of formula (3) expression
Object；
2) synthesis of oligonucleotides resin：Constant pressure funnel is used under a nitrogen, is added drop-wise to containing methacrylic acid, benzene after 1Hr
Ethylene, isobornyl methacrylate, methacrylic acid tricyclic [5.2.1.02,6] decyl- 8- base esters, hydroxyethyl methacrylate
(molar ratio of five kinds of monomers is 2.5：3：2：1：0.5) in four-hole boiling flask；And five kinds of monomer gross mass parts are added
0.3% azodiisobutyronitrile initiator, 0.3% chloroiodomethane chain-transferring agent, 150% EEP solvents.Pre-polymerization temperature is 70
DEG C, it is added in the four-hole boiling flask in 15min in a manner of dropwise addition, increases the temperature to 100 DEG C the reaction was continued 4Hr；
3) it post-processes：It is handled by the step 3) of embodiment 3, obtains bisphenol fluorene class acrylic resin II.
Product detection
The product of embodiment 1-4 is detected, table 1 is the copolymer assay result to above-described embodiment 1-4 synthesis.
Table 1：Testing result
Embodiment 5-10
Embodiment 5- embodiments 10 are using obtained by the obtained oligomeric resins of above-described embodiment 1-2 and embodiment 3-4
Bisphenol fluorene class acrylic resin prepares quantum stippling coloured light photosensitive resin composition according to the proportioning of table 2,
The preparation method includes the following steps：
A nano dye mill base) is prepared：By quanta point material and the granules of pigments of difference corresponding color in 0.1mm zirconium balls
Organic solvent is added in sand mill and carries out wet grinding, addition oligomeric resin compositions are as stable resin, system in process of lapping
It must disperse mill base；
B photosensitive liquid) is prepared：By formula ratio by bisphenol fluorene class acrylic resin of the present invention, vinyl photocuring tree
Fat, photoinitiator, coagent, polar organic solvent mixing are filtered after being dispersed into solution, obtain photosensitive liquid；
C quantum stippling coloured light photosensitive resin composition) is prepared：By step A) in dispersion mill base and step B) photosensitive liquid is mixed
It closes, and finally adds organic solvent adjustment viscosity, disperseed in dispersion machine, after filtering；
And obtained quantum dot color photosensitive resin compositions are subjected to photoetching development, photoetching development lines precision is shown in Table 2,
Simultaneously respectively with existing red photoresist, red quantum dot gel as a comparison case 1 and comparative example 2.
Table 2：Embodiment 5-10 and comparative example 1 and 2 photoetching development lines
In accordance with the following methods by the photoresist of the quantum dot color photosensitive resin compositions of embodiment 5-10 and comparative example 1-2
Pattern is manufactured on glass substrate/PET, and the performance of optical filter is detected, and the results are shown in Table 3：
1) substrate is fixed：Substrate is adhered to using vacuum and is fixed；
2) photoresist layer is made：Quantum dot color photosensitive resin of the present invention is coated in the substrate of above-mentioned 1) step
Composition forms 2-3 μm of colorful film of first layer using vacuum bakeout；
3) pixel pattern is made：In above-mentioned steps 2) colorful film on using mask masking, UV exposure, development, hardening
Step forms pattern on mask plate.
Table 3：Embodiment 5-10 and comparative example 1 and 2 monochromatic filter testing results
| Compare print | 10um lines | 10um lines | CD Loss | Film thickness | Fluorescent quantum | 10um lines |
| Solvent resistant | Acid and alkali-resistance | /um | Adherence | |||
| Embodiment 5 | ○ | ○ | 0.3 | 1.4 | ○ | ○ |
| Embodiment 6 | △ | △ | 0.3 | 1.5 | △ | △ |
| Embodiment 7 | ○ | ○ | 0.2 | 1.5 | △ | ○ |
| Embodiment 8 | △ | ○ | 0.3 | 1.2 | ○ | ○ |
| Embodiment 9 | ○ | △ | 0.5 | 1.3 | △ | △ |
| Embodiment 10 | ○ | ○ | 0.5 | 1.5 | △ | ○ |
| Comparative example 1 | ● | ● | 1.2 | 2.7 | ● | ● |
| Comparative example 2 | -- | -- | -- | 2.5 | ○ | It can not photoetching |
Note：● it indicates that pixel lines have and falls off；△ indicates that pixel lines are not fallen off, but Marker has and falls off；Zero indicates picture
Element and Marker are not fallen off；The unit of Slope values, film thickness value and CD Loss values is um.Fluorescent quantum is to use 400-
410nm wavelength blue lasers irradiate：● indicate unstressed configuration；△ indicates that fluorescence quantum efficiency is remarkably decreased, but has fluorescence；Zero table
It is not notable to show that fluorescence quantum efficiency declines
The above embodiment is only the preferred embodiment of the present invention, and the scope of protection of the present invention is not limited thereto,
The variation and replacement for any unsubstantiality that those skilled in the art is done on the basis of the present invention belong to institute of the present invention
Claimed range.
Claims (8)
1. a kind of quantum dot color photosensitive resin compositions, which is characterized in that it is prepared by following raw material in parts by weight
It forms：
20-50 parts of sub-pixel rendering agent；
40-90 parts of grind resin composition；
5-20 parts of bisphenol fluorene class acrylic resin；
10-20 parts of vinyl light-cured resin；
0.1-0.5 parts of photoinitiator；
0.1-1 parts of coagent；
30-50 parts of organic solvent；
The bisphenol fluorene class acrylic resin has following chemical structural formula (1)：
Wherein, n=10-230；R1And R3Indicate CH2；R2And R4Indicate OH；X and W are indicated respectivelyA indicates H or C1-
C3Alkyl；
The preparation method of the bisphenol fluorene class acrylic resin, includes the following steps：
(a) synthetic intermediate：By the monomer and acrylic compounds ring-opening polymerization generating structure indicated with structural formula (2)
The compound that formula (3) indicates；
(b) synthetic product：Continue to be added dropwise in acrylic compounds to the intermediate of structure above (3) under a nitrogen, reaction
Generating structure formula (1)；
(c) product postprocessing：Product is transferred to while hot when the intermediate reaction of structural formula (3) is complete by a chromatography board monitoring
Round-bottomed flask is purified, and off-white powder resin is obtained, dry, that is, is completed.
2. quantum dot color photosensitive resin compositions according to claim 1, which is characterized in that the acrylic compounds chemical combination
Object is methacrylic acid.
3. quantum dot color photosensitive resin compositions according to claim 1, which is characterized in that step (a) prepares intermediate
Body comprises the concrete steps that：The molar ratio of the monomer and acrylic compounds that are indicated according to structural formula (2) is 1:The ratio of (2-4)
Acrylic compounds are added in the monomer monomer that structural formula (2) indicates in example, and then addition accounts for structural formula (2) expression successively
1% tetramethyl ammonium chloride of monomer and acrylic compounds gross mass, 0.5% phenol, at 90 DEG C lead to nitrogen protection,
Being heated to 130 DEG C after 30min dissolvings completely, the reaction was continued, acid value measuring in reaction process, in solution acid value<Stop after 2.0mg
It only reacts, is evaporated under reduced pressure, obtains midbody compound.
4. quantum dot-color photosensitive resin compositions according to claim 1, which is characterized in that the sub-pixel rendering
Agent by least one of red light quantum point material, green light quantum point material, blue light quantum point material quanta point material and with the amount
The organic pigment composition of son point material corresponding color, the wherein mass ratio of quanta point material and organic pigment is 1：(5-10).
5. quantum dot-color photosensitive resin compositions according to claim 1, which is characterized in that the grind resin group
Object is closed to be made of the oligomeric resin, hyper-dispersant and solvent of structural formula (4)；
Wherein, in parts by weight respectively oligomeric resin 1-5 parts, 1-5 parts of hyper-dispersant, 40-80 parts of solvent.
6. a kind of preparation method of quantum dot color photosensitive resin compositions as described in claim 1, which is characterized in that should
Preparation method includes the following steps：
A nano dye mill base) is prepared：By subpixel colors quanta point material and the granules of pigments of difference corresponding color in 0.1mm
Organic solvent is added in the sand mill of zirconium ball and carries out wet grinding, addition oligomeric resin compositions are set as stable in process of lapping
Dispersion mill base is made in fat；
B photosensitive liquid) is prepared：By formula ratio by bisphenol fluorene class acrylic resin described in claim 1, vinyl photocuring tree
Fat, photoinitiator, coagent, polar organic solvent mixing are filtered after being dispersed into solution, obtain photosensitive liquid；
C quantum stippling coloured light photosensitive resin composition) is prepared：By step A) in dispersion mill base and step B) photosensitive liquid mixing, and
Organic solvent adjustment viscosity is finally added, is disperseed in dispersion machine, after filtering.
7. a kind of quantum dot color filter, which is characterized in that it is made by the following method：
S1：The black matrix of 1.5-3 μm of line spoke width of black photoresist formation is used on the glass substrate；
S2：Black matrix" surface covers quantum dot color photosensitive resin compositions as described in claim 1 and forms first layer coloured silk film,
Again first layer pixel is formed by the masking of contraposition mask, partial exposure, development, cure step successively；
S3：Second formed with quantum dot color photosensitive resin compositions as described in claim 1 in the first pixel layer surface
Layer pixel and third layer pixel, wherein the sub-pixel color in quantum dot color photosensitive resin compositions used by second layer pixel
Color sub-pixel rendering agent is made of green light quantum point material and green organic pigment, quantum stippling used by third layer pixel
Subpixel colors sub-pixel rendering agent in coloured light photosensitive resin composition is by blue quanta point material and blue organic pigment group
At；
S4：Finally encapsulate to form colored filter using Over CoatingII photoresists.
8. a kind of method manufacturing pattern on glass substrate/PET, which is characterized in that include the following steps：
1) substrate is fixed：Substrate is adhered to using vacuum and is fixed；
2) photoresist layer is made：Quantum dot color photosensitive tree as described in claim 1 is coated in the substrate of above-mentioned 1) step
Oil/fat composition forms 2-3 μm of colorful film of first layer using vacuum bakeout；
3) pixel pattern is made：In above-mentioned steps 2) colorful film on using mask masking, UV exposure, development, cure step
Form pattern on mask plate.
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| PCT/CN2016/107713 WO2017092650A1 (en) | 2015-11-30 | 2016-11-29 | Bisphenol fluorene acrylic resin and preparation method therefor, quantum dot-coloured photosensitive resin composition, preparation method therefor and use thereof |
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| CN105504120B (en) * | 2015-11-30 | 2018-09-21 | 东莞职业技术学院 | Bisphenol fluorene acrylic resin and preparation method thereof, quantum dot-colored photosensitive resin composition and preparation method and application thereof |
| KR101976659B1 (en) | 2016-12-12 | 2019-05-09 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer using same and color filter |
| US10472563B2 (en) * | 2017-02-16 | 2019-11-12 | Rohm And Haas Electronic Materials Llc | Methods for making improved quantum dot resin formulations |
| US10508232B2 (en) * | 2017-02-16 | 2019-12-17 | Dow Global Technologies Llc | Polymer composites and films comprising reactive additives having thiol groups for improved quantum dot dispersion and barrier properties |
| KR102296790B1 (en) * | 2018-02-06 | 2021-09-02 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer using same and color filter |
| US10921709B2 (en) * | 2018-02-06 | 2021-02-16 | Samsung Sdi Co., Ltd. | Photosensitive resin composition, photosensitive resin layer using the same, and color filter |
| CN108394093A (en) * | 2018-03-20 | 2018-08-14 | 珠海天威飞马打印耗材有限公司 | Photosensitive resin composition, photocuring three-dimensional printer and its Method of printing |
| KR20190110415A (en) * | 2018-03-20 | 2019-09-30 | 동우 화인켐 주식회사 | A light converting resin composition, a light converting unit and a display device using the same |
| KR102154680B1 (en) | 2018-07-02 | 2020-09-10 | 삼성에스디아이 주식회사 | Curable composition including quantum dot, resin layer using the same and display device |
| CN112180683B (en) * | 2020-08-28 | 2021-10-08 | 上海玟昕科技有限公司 | Positive high-elasticity photosensitive resin composition |
| CN114975218B (en) * | 2022-05-21 | 2023-03-31 | 东莞市德镌精密设备有限公司 | Mass transfer and mass welding process of LED crystal grains |
| CN115598926A (en) * | 2022-10-28 | 2023-01-13 | 深圳市邦得凌半导体材料有限公司（Cn） | Quantum dot colored photosensitive resin composition and preparation method thereof |
| WO2024247800A1 (en) * | 2023-05-29 | 2024-12-05 | 株式会社トクヤマ | Curable composition, cured body, optical article, lens, and eye glasses |
| CN117143558B (en) * | 2023-10-26 | 2023-12-26 | 信泰永合(烟台)新材料有限公司 | High-specific gravity high-weather-resistance ultraviolet deep-curing adhesive and preparation method thereof |
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Effective date of registration: 20220127 Address after: 518000 503, plant 20-2, No. 20, houye Road, Heping community, Fuhai street, Bao'an District, Shenzhen, Guangdong Province Patentee after: Shenzhen Bangdeling Touch Display Technology Co.,Ltd. Address before: 518000 301, plant 7, TONGCHAN Lixing science and Technology Industrial Park, No. 1001, Longgang Avenue (Ping section), Pingxi community, Pingdi street, Longgang District, Shenzhen City, Guangdong Province Patentee before: Shenzhen Qinghe Technology Co.,Ltd. |
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| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 518000 503, plant 20-2, No. 20, houye Road, Heping community, Fuhai street, Bao'an District, Shenzhen, Guangdong Province Patentee after: Shenzhen bangdeling semiconductor material Co.,Ltd. Address before: 518000 503, plant 20-2, No. 20, houye Road, Heping community, Fuhai street, Bao'an District, Shenzhen, Guangdong Province Patentee before: Shenzhen Bangdeling Touch Display Technology Co.,Ltd. |