CN107111232A - Black matrix" photo-corrosion-resisting agent composition for liquid crystal display panel - Google Patents
Black matrix" photo-corrosion-resisting agent composition for liquid crystal display panel Download PDFInfo
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- CN107111232A CN107111232A CN201580073141.9A CN201580073141A CN107111232A CN 107111232 A CN107111232 A CN 107111232A CN 201580073141 A CN201580073141 A CN 201580073141A CN 107111232 A CN107111232 A CN 107111232A
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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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- 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
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- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
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- Spectroscopy & Molecular Physics (AREA)
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Abstract
The present invention relates to a kind of black matrix" photo-corrosion-resisting agent composition for liquid crystal display panel, the black matrix" photo-corrosion-resisting agent composition is due to using transmissivity of the excellent Photoepolymerizationinitiater initiater without the influence liquid crystal display panel, the effect and suppression aberration generation phenomenon of reflectivity with reduction black matrix film, be conducive to deep section solidification simultaneously to promote pattern to be formed, specifically he, the oxime ester fluorene derivative compound as Photoepolymerizationinitiater initiater is characterised by being represented as the chemical formula 1 described in this specification in the present invention.
Description
Technical field
The present invention relates to a kind of black matrix" for liquid crystal display, the black matrix" is light shield lightsensitive resin composition
Thing.More particularly it relates to which photosensitive resin composition, the photosensitive resin composition can be used for manufacturing by using photoetching process
Black matrix" for liquid crystal display.
This application claims the preferential of the korean patent application the 10-2014-0157328th submitted on November 12nd, 2014
Power, all the elements described in the specification of the korean patent application are herein incorporated by reference.
In addition, this application claims the korean patent application the 10-2015-0158807th submitted on November 12nd, 2015
Priority, all the elements described in the specification of the korean patent application are herein incorporated by reference.
Background technology
Generally, black matrix" photo-corrosion-resisting agent composition is to be included in display element (colour filter, liquid crystal display for making
Device, organic electroluminescence device and display panel) in colour filter necessary material.The black matrix" photoresist is combined
Color mixture in colour filter of the thing for preventing liquid crystal display device between R (red), G (green) and B (blueness), or the black
Matrix photo-corrosion-resisting agent composition is used for the frame for covering X metal electrodes and Y metal electrodes in touch control panel device.
Recently in the liquid crystal display device for display, as being applied to more than super definition (ultra
Definition, UD) high-resolution and more than 240Hz high-speed driving device, actively research low temperature polycrystalline silicon
(low temperature polysilicon, LTPS) and oxide thin film transistor.
Typically, since oxide thin film transistor light and change the property of semiconductor, so introducing light shielding layer with most
Smallization above mentioned problem.Because including plasma enhanced chemical vapor deposition (plasma-enhanced after light shielding layer is formed
Chemical vapor deposition, PE-CVD) subsequent technique carry out at high temperature, so the light shielding layer is main
Using metal light shielding layer, but metal light shielding layer has the following problems：Due to high reflectance, light is reflected back source electrode, leakage
Between pole electrode and light shielding layer, and stray voltage betides between source electrode and drain electrode and serves as the operation to device
Apply the factor of resistance, so that causing the load of data wire increases.
Especially, Organic Light Emitting Diode (organic light-emitting diode, OLED) and transparent display is
The obvious reduction of the contrast as caused by the reflection of upper metal line and lower metal line is prevented using light shielding layer.
[prior art literature]
[patent document]
(patent document 1) [patent document 1] KR 2007-0131523 (2007.12.14)
(patent document 2) [patent document 2] KR 2009-0131415 (2009.12.28)
(patent document 3) [patent document 3] JP 2011-247437 (2011.11.11)
The content of the invention
Technical problem
Therefore, a purpose of the invention is to provide a kind of black matrix" photoresist group for liquid crystal display panel
Compound, it has reflectivity reducing effect and prevents aberration from occurring phenomenon and be conducive to deep section solidification (deep-section
Cure) so as to promote the manufacturability of pattern formation and developing process.
Technical scheme
To reach above-mentioned purpose, the present invention provides a kind of black matrix" photo-corrosion-resisting agent composition, and it includes poly- as light
Close the oxime ester fluorene derivative compound represented by following chemical formula 1 of initiator：
[chemical formula 1]
In above-mentioned chemical formula 1,
R1To R3Each of independently be hydrogen atom, halogen atom, (C1-C20) alkyl, (C6-C20) aryl, (C1-
C20) alkoxy, (C6-C20) aryl (C1-C20) alkyl, hydroxyl (C1-C20) alkyl, hydroxyl (C1-C20) alkoxy (C1-
C20) alkyl or (C3-C20) cycloalkyl；
A is hydrogen atom, (C1-C20) alkyl, (C6-C20) aryl, (C1-C20) alkoxy, (C6-C20) aryl (C1-
C20) alkyl, hydroxyl (C1-C20) alkyl, hydroxyl (C1-C20) alkoxy (C1-C20) alkyl, (C3-C20) cycloalkyl, amino,
Nitro, cyano group or hydroxyl；
N is 0 or 1.
Described " alkyl ", " alkoxy " and other substituents for including " alkyl " part include all straight in the present invention
Chain or branched form, and " cycloalkyl " includes monocyclic hydrocarbon and polycyclic hydrocarbon.As used herein term " aryl " refers to by removal
One hydrogen atom and the organic group produced from aromatic hydrocarbon, and including monocyclic or fused ring system, its in each ring suitably
Containing 4 to 7 annular atoms, preferably containing 5 or 6 annular atoms, and even include polyaryl by singly-bound type of attachment.Art
Language " hydroxy alkyl " refers to the OH- alkyl that hydroxyl is bonded to alkyl defined above, and " hydroxy alkoxy alkyl " refers to bonding
To the hydroxy alkyl-O- alkyl of the alkoxy of above hydroxy alkyl.
In addition, as used herein " (C1-C20) alkyl " is preferably (C1-C10) alkyl, more preferably (C1-
C6) alkyl." (C6-C20) aryl " is preferably (C6-C18) aryl." (C1-C20) alkoxy " is preferably (C1-C10) alkane
Epoxide, more preferably (C1-C4) alkoxy." (C6-C20) aryl (C1-C20) alkyl " is preferably (C6-C18) aryl
(C1-C10) alkyl, more preferably (C6-C18) aryl (C1-C6) alkyl." hydroxyl (C1-C20) alkyl " is preferably hydroxyl
(C1-C10) alkyl, more preferably hydroxyl (C1-C6) alkyl." hydroxyl (C1-C20) alkoxy (C1-C20) alkyl " preferably
For hydroxyl (C1-C10) alkoxy (C1-C10) alkyl, more preferably hydroxyl (C1-C4) alkoxy (C1-C6) alkyl.“(C3-
C20) cycloalkyl " is preferably (C3-C10) cycloalkyl.
More specifically, R1To R3Each of independently be hydrogen atom, bromine atoms, chlorine atom, iodine atom, methyl, second
Base, n-propyl, isopropyl, normal-butyl, isobutyl group, the tert-butyl group, n-pentyl, isopentyl, n-hexyl, isohesyl, phenyl, naphthyl,
Biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy,
Tert-butoxy, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, hydroxy-n-butyl, hydroxyisobutyl, hydroxyl n-pentyl, hydroxyl are different
Amyl group, hydroxyl n-hexyl, hydroxyl isohesyl, hydroxymethoxy methyl, hydroxymethoxy ethyl, hydroxymethoxy propyl group, hydroxyl
Methoxybutyl, hydroxyethoxymethyl, hydroxyl ethoxy ethyl, hydroxyethoxypropyl, hydroxyl-oxethyl butyl, hydroxyl second
Epoxide amyl group or hydroxyl-oxethyl hexyl.
A can for hydrogen atom, methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, the tert-butyl group, phenyl, naphthyl,
Biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxyl group, ethyoxyl, propane epoxide, butoxy, hydroxymethyl, hydroxyethyl, hydroxyl
Base propyl group, hydroxybutyl, hydroxymethoxy methyl, hydroxymethoxy ethyl, hydroxymethoxy propyl group, hydroxymethoxy butyl,
Hydroxyethoxymethyl, hydroxyl ethoxy ethyl, hydroxyethoxypropyl, hydroxyl-oxethyl butyl, amino, nitro, cyano group or
Hydroxyl.
Following compound is typically comprised according to the oxime ester fluorene derivative compound of the present invention, but following compound is not limited
The present invention.
In the present invention, the oxime ester fluorene derivative compound represented by above-mentioned chemical formula 1 is in black matrix" photoresist
Exist in composition and be used as Photoepolymerizationinitiater initiater.
The black matrix" photo-corrosion-resisting agent composition of the present invention includes the oxime ester fluorene derivative represented by above-mentioned chemical formula 1
Compound, adhesive resin, the polymerism chemical combination with ethylenic unsaturated bond (ethylenically unsaturated bond)
Thing and colouring agent, reduce effect with reflectivity and prevent aberration from occurring phenomenon and with excellent film characteristics, it is all if any
Solidify beneficial to deep section and promote pattern to be formed.
In the black matrix" photo-corrosion-resisting agent composition of the present invention, adhesive resin can use acrylic acid series
(acryl-based) (acrylic resin is acrylic acid series polymeric compounds or has acrylic acid series unsaturated on side chain resin
The acrylic acid series polymeric compounds of key), phenolphthalein base class (cardo-based) resin, silicon substrate (silicone-based) resin or it is mixed
Compound.
The content of adhesive resin may be adjusted to adjustment pattern properties and assign property of thin film, such as heat resistance and resistance toization
The property learned.For example, the photo-corrosion-resisting agent composition relative to 100wt%, the content of adhesive resin can be 3wt% to 50wt%.
The weight average molecular weight of adhesive resin is preferably 2,000 to 300,000, and decentralization is preferably 1.0 to 10.0, and again
Amount mean molecule quantity is more preferably 4,000 to 100,000.
Acrylic acid series polymeric compounds are the copolymer of following monomer, and the example of the monomer includes methyl methacrylate, first
Base ethyl acrylate, propyl methacrylate, butyl methacrylate, pentylmethacrylate, hexyl methacrylate, methyl
Cyclohexyl acrylate, metering system heptyl heptylate, 2-Propenoic acid, 2-methyl-, octyl ester, nonyl methacrylate, decyl-octyl methacrylate, methyl
Lauryl acrylate, lauryl methacrylate, tetradecyl methylacrylate and hexadecyl metrhacrylate, methacrylic acid are different
Norbornene ester, methacrylic acid Buddha's warrior attendant alkyl ester, the ring pentyl ester of methacrylic acid two, methacrylic acid dicyclopentenyl ester, methacrylic acid
Benzyl ester, methacrylic acid 2- methoxy acrylates, methacrylic acid 2- ethoxy ethyl esters, acrylic acid, methacrylic acid, itaconic acid,
Maleic acid, maleic anhydride, maleic acid list alkyl ester, itaconic acid list alkyl ester, fumaric acid list alkyl ester, acrylic acid
Ethylene oxidic ester, GMA, methacrylic acid 3,4- epoxy radicals butyl ester, methacrylic acid 2,3- epoxy radicals
Cyclohexyl, methacrylic acid 3,4- expoxycyclohexyls methyl esters, methacrylic acid 3- methyl oxa- ring butyl- 3- methyl esters, methyl-prop
Olefin(e) acid 3- ethyl oxa- ring butyl- 3- methyl esters, styrene, α-methylstyrene, acetoxy-styrene, N- methyl maleoyl-s
Imines, N-ethylomaleimide, N- propyl group maleimide, N- butyl maleimide, N- cyclohexyl
Maleimide, Methacrylamide and N- methyl methacrylamides, these monomers can be used alone or two kinds with
On be applied in combination.
The acrylic acid series polymeric compounds with acrylic acid series unsaturated bond are to containing carboxylic acid using epoxy resin on side chain
Acrylic acid series copolymer carry out copolymer formed by addition reaction, and ring is utilized at a temperature of being included in 40 DEG C to 180 DEG C
Oxygen tree fat (such as glycidyl acrylate, GMA, methacrylic acid 3,4- epoxy radicals butyl ester, first
Base acrylic acid 2,3- epoxycyclohexyethylSiOis ester and methacrylic acid 3,4- expoxycyclohexyls methyl esters) to the acrylic acid series containing carboxylic acid
The adhesive resin that copolymer carries out addition reaction and obtained, the acrylic acid series copolymer to following material by carrying out combined polymerization
And obtain：Acrylic monomer containing carboxylic acid, such as acrylic acid, methacrylic acid, itaconic acid, maleic acid and maleic
Diacid list alkyl ester；And alkyl methacrylate (methyl methacrylate, hexyl methacrylate), methacrylic acid hexamethylene
Ester, isobornyl methacrylate, methacrylic acid Buddha's warrior attendant alkyl ester, the ring pentyl ester of methacrylic acid two, the ring penta of methacrylic acid two
Alkene ester, benzyl methacrylate, methacrylic acid 2- methoxy acrylates, methacrylic acid 2- ethoxy ethyl esters, styrene, α-first
Base styrene, acetoxy-styrene, N- methyl maleimides, N-ethylomaleimide, N- propyl group are along fourth
Alkene imidodicarbonic diamide, N- butyl maleimide, N- cyclohexylmaleimides, Methacrylamide and N- methyl first
Two or more monomers in base acrylamide etc..
On side chain with acrylic acid series unsaturated bond acrylic acid series polymeric compounds another example be using carboxylic acid to containing
The acrylic acid series copolymer for having epoxy radicals carries out copolymer formed by addition reaction, and is included in 40 DEG C to 180 DEG C of temperature
It is viscous that the lower acrylic acid series copolymer by the acrylic monomer containing carboxylic acid and containing epoxy radicals carries out addition reaction and obtained
Mixture resin, the acrylic monomer containing carboxylic acid is, for example, acrylic acid, methacrylic acid, itaconic acid, maleic acid
And maleic acid list alkyl ester, the acrylic acid series copolymer to the progress combined polymerization of following material by obtaining：Contain epoxy
The acrylic monomer of base, such as glycidyl acrylate, GMA, methacrylic acid 3,4- epoxies
Base butyl ester, methacrylic acid 2,3- epoxycyclohexyethylSiOis ester and methacrylic acid 3,4- expoxycyclohexyl methyl esters；And metering system
Acid alkyl ester (methyl methacrylate, hexyl methacrylate), cyclohexyl methacrylate, isobornyl methacrylate,
Methacrylic acid Buddha's warrior attendant alkyl ester, the ring pentyl ester of methacrylic acid two, methacrylic acid dicyclopentenyl ester, benzyl methacrylate, first
Base acrylic acid 2- methoxy acrylates, methacrylic acid 2- ethoxy ethyl esters, styrene, α-methylstyrene, acetyloxy phenyl second
Alkene, N- methyl maleimides, N-ethylomaleimide, N- propyl group maleimide, N- butyl are along fourth
Two kinds in alkene imidodicarbonic diamide, N- cyclohexylmaleimides, Methacrylamide and N- methyl methacrylamides etc.
Above monomer.
In addition, embodiments in accordance with the present invention, phenolphthalein base class resin can be used as adhesive resin, and phenolphthalein base class resin refers to
The acryloyl system adhesive resin containing fluorenyl on main chain, and it is not limited in structure particular type.
In addition, silicone includes silicone resin, and more specifically, silicone includes Korean granted patent 10-
Silicone resin disclosed in No. 1537771, and can be prepared using preparation method described in above-mentioned patent.Siloxanes
Resin can have the acid number in the range of 10~200mgKOH/g resins (being titrated by KOH).
In one embodiment of the invention, available silicone resin can be including being represented by following chemical formula 2
The silicone resin of polymerized unit and the polymerized unit represented by following chemical formula 3.
[chemical formula 2]
X-R4-SiO3/2
In above-mentioned chemical formula 2,
R4For the straight or branched alkylidene with 1 to 20 carbon atom, the arlydene with 6 to 20 carbon atoms, quilt
Having for aryl substitution amounts to the alkylidene of 7 to 20 carbon atoms, by the alkyl-substituted Asia for having and amounting to 7 to 20 carbon atoms
Aryl, or with the group for amounting to 7 to 20 carbon atoms, wherein alkylidene is connected to arlydene,
X be hydroxyl, carboxylic acid, carboxylic acid anhydrides, polycalboxylic. anhydride derivative, acid imide, imide derivative, acid amides, amide derivatives,
Amine or sulfydryl.
[chemical formula 3]
R4SiO(4-n)/2
In above-mentioned chemical formula 3,
R4It is each independently hydrogen atom, the straight chain with 1 to 20 carbon atom, side chain or cyclic alkyl, with 6 to 10
The aryl of individual carbon atom, the unsaturated alkyl with 2 to 10 carbon atoms or the acyloxy with 2 to 10 carbon atoms, wherein
A plurality of R in molecule2It is identical or different, and n is 0 to 3 integer, and polymerized unit (wherein n=3) can polymerize list with another
Member (wherein n is different from 3) is applied in combination.
Counted using the summation of the polymerized unit of chemical formula 2 and the polymerized unit of chemical formula 3 as 100mol%, silicone resin can
It is made up of the polymerized unit of 5-40mol% chemical formula 2 and the 95-60mol% polymerized unit of chemical formula 3.
The particular instance of silicone resin include but is not limited to by following chemical formula 4 to 17 represent the first polymerized unit and
The silicone resin that the second polymerized unit being listed below is constituted.
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
[chemical formula 12]
[chemical formula 13]
[chemical formula 14]
[chemical formula 15]
[chemical formula 16]
[chemical formula 17]
(in each formula, in m and n can be separately 1 to 20 integer.)
In addition, constituting the monomer of the second polymerized unit is included selected from one of group being made up of following person or many persons：Four alkane
It is TMOS, trialkoxy silane, methyl trialkoxysilane, ethyltrialkoxysilanes, n-propyl trialkoxy silane, different
Propyl trialkoxy silane, normal-butyl trialkoxy silane, tert-butyl group trialkoxy silane, phenyl trialkoxysilane, naphthalene three
Alkoxy silane (naphtha trialkoxysilane), vinyl trialkyl oxysilane, the alkane of methacryloxymethyl three
TMOS, 2- methacryloxyethyls trialkoxy silane, 3- methacryloxypropyls trialkoxy silane, 3-
Methacryloyloxypropyl methyl dialkoxy silicane, 3- methacryloxypropyl ethyls dialkoxy silicane, propylene
Pivaloyloxymethyl trialkoxy silane, 2- acryloyl-oxyethyls trialkoxy silane, 3- acryloxy propyl trialkoxies
Silane, 3- acryloxypropyls dialkoxy silicane, 3- acryloxypropyl ethyls dialkoxy silicane, 3- shrink
Glycerine epoxide propyl trialkoxy silane, 2- epoxy cyclohexylethyls trialkoxy silane, 3- expoxycyclohexyls propyl group three
Alkoxy silane, dimethyl alkoxy silane, diethyl dialkoxy silicane, dipropyl dialkoxy silicane, diphenyl dioxane
TMOS, diphenyl silanodiol and phenyl methyl dialkoxy silicane.Herein, alkoxy is with 1 to 7 carbon atom
Straight chain, side chain or annular aliphatic or aromatic series alkoxy, and can be hydrolysable halogen compound.
In the black matrix" photo-corrosion-resisting agent composition of the present invention, the polymerizable compound with ethylenic unsaturated bond exists
It is crosslinked when forming pattern by light reaction to promote pattern to be formed, and when heating at high temperature, it is crosslinked resistance to assign
Chemically and heat resistance.The content of polymerizable compound with ethylenic unsaturated bond can be the adhesive tree of every 100 parts by weight
The parts by weight of fat 1 to 200, preferably 10 to 150 parts by weight and more preferably 50 to 120 parts by weight.When with ethylenic unsaturated bond
The content of polymerizable compound when meeting this scope, the excessive increase of the degree of cross linking is prevented, and maintains the appropriate soft of pattern
Property.
Polymerizable compound with ethylenic unsaturated bond specifically includes Arrcostab (such as metering system of methacrylic acid
Sour methyl esters, EMA, butyl methacrylate, 2-Ethylhexyl Methacrylate and lauryl methacrylate),
By polyalcohol and α, compound that the esterifications of two unsaturated carboxylic acids is obtained (such as GMA, with 2 to 14
The polyethylene glycol monomethacrylate of individual oxyethylene group, ethylene glycol dimethacrylate, with 2 to 14 ethylene oxides
The polyethylene glycol dimethacrylate of base, the dimethacrylate with 2 to 14 oxypropylene groups, three hydroxyl first
Base propane dimethylacrylate, bisphenol A diglycidyl ether ether acrylic acid adduct, the neighbour of methacrylic acid dihydroxy ethyl ester
Ester, the tolylene diisocyanate adduct of methacrylic acid dihydroxy ethyl ester, trimethylol propane trimethyl third
Olefin(e) acid ester, pentaerythritol acrylate trimethyl, pentaerythritol tetramethylacrylate, dipentaerythritol pentamethyl acrylic acid
Ester, dipentaerythritol hexamethacrylate and dipentaerythritol trimethyl acrylic ester) and multivalence glycidyl compound
Acrylic acid adduct (trimethylolpropane tris glycidyl ether acrylic acid adduct) etc., its can be used alone or
It is used in combination.
In addition, the present invention black matrix" photo-corrosion-resisting agent composition in as Photoepolymerizationinitiater initiater formula 1 oxime ester
The content of fluorene derivative compound can be the weight of polymerizable compound 0.01 to 50 with ethylenic unsaturated bond of every 100 parts by weight
Part, preferably 0.02 to 25 parts by weight, 0.5 to 10 parts by weight are measured, to minimize the reflectivity of black matrix" and to prevent aberration
Occur and reach favourable deep section solidification.
When the content of Photoepolymerizationinitiater initiater meets this scope, photocuring degree is ensured so that due to exposure area with
Development sex differernce between unexposed area and be relatively easy to form pattern, prevent the T because of caused by the over-curing of upper area
The formation of shape pattern, and desired pattern form can be obtained.
According to one embodiment of present invention, in addition to the oxime ester fluorene derivative compound of chemical formula 1, photoresist group
Compound may also include additional Photoepolymerizationinitiater initiater, and it is selected from by one or more in following constituted group：Thioxanthones system
(thioxanthone-based) compound, acetophenone system (acetophenone-based) compound, bisglyoxaline system
(biimidazole-based) compound, triazine system (triazine-based) compound, mercaptan system (thiol-based) change
Compound and O- acyl group oximes system (O-acyloxime-based) compound in addition to the compound represented by chemical formula 1.
Thioxanthones based compound include for example thioxanthones, CTX, 2- methyl thioxanthones, ITX,
ITX, the clopenthixal ketones of 2,4- bis-, 2,4- dimethyl thioxanthones, 2,4- diethyl thioxanthones and 2,4- diisopropyls
Thioxanthones.Acetophenone based compound includes such as 2- methyl isophthalic acids-[4- (methyl mercapto) phenyl] -2- morpholinopropane -1- ketone, 2- benzyls
Base -2- dimethylaminos -1- (4- morpholino phenyls) butane -1- ketone and 2- (4- methyl-benzyls) -2- (dimethylamino) -1-
(4- morpholino phenyls) butane -1- ketone.Bisglyoxaline based compound includes double (2- the chlorphenyls) -4,4', 5,5'- tetra- of such as 2,2'-
Double (2,4 dichloro benzene base) -4,4', the 5,5'- tetraphenyl -1,2'- bisglyoxalines of phenyl -1,2'- bisglyoxalines, 2,2'- and 2,2'- are double
(2,4,6- trichlorophenyls) -4,4', 5,5'- tetraphenyl -1,2'- bisglyoxalines.Triazine based compound includes such as 2,4,6- tri- (three
Chloromethyl)-s- triazines, double (the trichloromethyl)-s- triazines of 2- methyl -4,6-, 2- [2- (5- methylfuran -2- bases) vinyl] -
Double (the trichloromethyl)-s- triazines of 4,6-, double (the trichloromethyl)-s- triazines of 2- [2- (furans -2- bases) vinyl] -4,6-, 2- [2-
(4- diethylamino -2- aminomethyl phenyls) vinyl] -4,6- pairs of (trichloromethyl)-s- triazines, 2- [2- (3,4- dimethoxy benzenes
Base) vinyl] double (the trichloromethyl)-s- triazines of -4,6-, double (the trichloromethyl)-s- triazines of 2- (4- methoxyphenyls) -4,6-,
Double (the trichloromethyl)-s- triazines of 2- (4- ethoxystyrenes base) -4,6- and the double (trichlorines of 2- (4- n-butoxyphenyls) -4,6-
Methyl)-s- triazines.
O- acyl groups oxime compound includes such as 1,2- octanediones, 1- [4- (thiophenyl) phenyl] -2- (O- benzoyls
Oxime), ethyl ketone -1- [9- ethyls -6- (2- methyl benzoyls) -9H- carbazole -3- bases] -1- (O- acetyl group oxime), ethyl ketone -1- [9-
Ethyl -6- (2- methyl -4- tetrahydrofuran base methoxybenzoyls base) -9H- carbazole -3- bases] -1- (O- acetyl group oxime) and second
Ketone -1- [9- ethyl -6-X2- methyl -4- (2,2- dimethyl -1,3- dioxolanes) methoxybenzoyl base r-9H- carbazoles -3-
Base] -1- (O- acetyl group oxime).
Except the oxime ester fluorenes of the chemical formula 1 of the Photoepolymerizationinitiater initiater in the photo-corrosion-resisting agent composition as the present invention derives
Outside compounds, the content of additional Photoepolymerizationinitiater initiater can be the polymerism with ethylenic unsaturated bond of every 100 parts by weight
The parts by weight of compound 0.01 to 20, preferably 0.05 to 10 parts by weight.
In addition, the black matrix" photo-corrosion-resisting agent composition of the present invention can further comprise when needed with epoxy radicals or
The silicon base compound of amido is used as bonding agent.In black matrix" photo-corrosion-resisting agent composition, silicon base compound can improve ITO
Heat resistance after bonding force between electrode and photo-corrosion-resisting agent composition, and enhancing solidification.Silicon with epoxy radicals or amido
Based compound includes (3- glycidoxypropyls) trimethoxy silane, (3- glycidoxypropyls) triethoxysilicane
Alkane, (3- glycidoxypropyls) methyl dimethoxysilane, (3- glycidoxypropyls) methyldiethoxysilane,
(3- glycidoxypropyls) dimethyl methoxy silane, (3- glycidoxypropyls) dimethylethoxysilane, 3,
4- epoxy radicals butyl trimethoxy silane, 3,4- epoxy radicals butyl triethoxysilane, 2- (3,4- expoxycyclohexyls) ethyl
Trimethoxy silane, 2- (3,4- expoxycyclohexyl) ethyl triethoxysilanes and TSL 8330, it can
To be used alone or be used in combination.The content of silicon base compound with epoxy radicals or amido can be every 100 weight
The parts by weight of adhesive resin 0.0001 to 20 of part.
In addition, the black matrix" photo-corrosion-resisting agent composition of the present invention can further comprise with compatibility when needed
Additive, such as sensitising agent, thermal polymerization inhibitor, defoamer and leveling agent.
In addition, the colouring agent of the present invention is included selected from least one of following：Carbon black, titanium black (titan black), second
Acetylene black, black nigrosine, perylenes, strontium titanates, chromium oxide and cerium oxide (ceria), foregoing preferably shows light shielding properties.Coloring
The content of agent can be the parts by weight of adhesive resin 1 to 300 of every 100 parts by weight, preferably 3 to 200 parts by weight, more preferably 5
To 150 parts by weight.
When the content of colouring agent meets this scope, light shield effect can be improved, and for the technique of pattern formation
Characteristic and electrical characteristic can be enhanced.
Black matrix" photo-corrosion-resisting agent composition can be used for forming figure via a method according to an embodiment of the invention
Case, this method addition solvent, spin coating is carried out on substrate, is developed using mask, irradiation ultraviolet radiation and using alkaline developer.
The content of solvent can be the parts by weight of adhesive resin 10 to 3,000 of every 100 parts by weight, preferably 20 to 1,000 parts by weight, more
Preferably 30 to 500 parts by weight.
In view of the compatibility with adhesive resin, Photoepolymerizationinitiater initiater and other compounds, solvent include ethyl acetate,
Butyl acetate, diethylene glycol dimethyl ether, diethylene glycol dimethylether, propionic acid methyl methoxy base ester, propionic acid ethyl ethoxylated ester
(ethylethoxy propionate, EEP), ethyl lactate, propylene glycol methyl ether acetate (propylene glycol
Monomethyl ether acetate, PGMEA), propylene glycol monomethyl ether acetate (propylene glycol methyl
Ether propionate, PGMEP), propylene glycol monomethyl ether, propylene glycol propyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol ethyl ethers ether acetic acid
Ester, diethylene glycol methyl acetic acid ester, diethylene glycol ethyl acetic acid esters, acetone, methylisobutylketone, cyclohexanone, dimethylformamide
(dimethyl formamide, DMF), DMA (N, N-dimethyl acetamide, DMAc), N- first
It is base -2-Pyrrolidone (N-methyl-2-pyrrolidone, NMP), gamma-butyrolacton, diethyl ether, glycol dimethyl ether, two sweet
Diethylene glycol dimethyl ether, tetrahydrofuran (tetrahydrofuran, THF), methanol, ethanol, propyl alcohol, isopropanol, methyl cellosolve, ethyl
Cellosolve, diethylene glycol dimethyl ether, diethylene glycol ether, dipropylene glycol methyl ether, toluene, dimethylbenzene, hexane, heptane and octane, its
It can be used alone or be used in combination.
In addition, including through including for the coloured material applied to the resist for being used for the black matrix" for forming the present invention
Carbon black, titanium are black, nigrosine and C.I. pigment blacks 7 etc..
Technique effect
The black matrix" photo-corrosion-resisting agent composition of the present invention has the advantage that, by using oxime ester fluorene derivative
Compound as Photoepolymerizationinitiater initiater, said composition can be usefully used for produce film, the film have reflectivity reducing effect and
Prevent aberration from occurring phenomenon and be conducive to deep section solidification (deep-section cure) to promote pattern to be formed.
Embodiment
Hereinafter, representative compound of the invention will be described in detail by embodiment and comparative example, with up to complete
Understand the purpose of the present invention, and embodiments in accordance with the present invention can be changed in many different forms, and the scope of the present invention
It should not be construed as limited by embodiment mentioned below.Embodiments of the invention are provided with more complete to one of ordinary skill in the art
The present invention is described to face.
<The preparation of adhesive resin>
1) preparation of adhesive resin 1
By 200mL propylene glycol methyl ether acetates (propylene glycol methyl ether acetate,
PGMEA) and after 1.5g azodiisobutyronitriles (azoisobutyronitrile, AIBN) are put into 500mL aggregation containers, with first
Base acrylic acid, GMA, methyl methacrylate and the ring pentyl ester of methacrylic acid two are 20:20:40:20
Molar ratio, with 40wt% additions solid propenoic acid system monomer, then stir 5 hours and gather at 70 DEG C in a nitrogen atmosphere
Close, to prepare acrylic acid series polymeric compounds, i.e. adhesive resin 1.The mean molecule quantity for measuring gained copolymer is 25,000, and
It is 1.9 to measure decentralization.
2) preparation of adhesive resin 2
After 200mL propylene glycol methyl ether acetates and 1.0g AIBN are put into 500mL aggregation containers, with metering system
Acid, styrene, methyl methacrylate and cyclohexyl methacrylate are 40:20:20:20 molar ratio, added with 40wt%
Reinforcing body acrylic monomer, then stirs 5 hours and polymerize at 70 DEG C, with synthetic copolymer in a nitrogen atmosphere.Will
0.3g DMAs and 20 mole ethylene oxidic esters are put into this reactor, are then stirred at 100 DEG C
Mix 10 hours to prepare the acrylic acid series polymeric compounds on side chain with acrylic acid series unsaturated bond, i.e. adhesive resin 2.Survey
The mean molecule quantity for obtaining gained copolymer is 20,000, and it is 2.0 to measure decentralization.
3) preparation of adhesive resin 3
After 200mL propylene glycol methyl ether acetates and 1.0g AIBN are put into 500mL aggregation containers, with metering system
Acid glycidyl ester, styrene, methyl methacrylate and cyclohexyl methacrylate are 40:20:20:20 molar ratio,
With 40wt% addition solid propenoic acids system monomer, then stir 5 hours and polymerize at 70 DEG C in a nitrogen atmosphere, to synthesize altogether
Polymers.0.3g DMAs and every mol propylene acid of 100 moles of solid total monomers 20 are put into this reactor, and
Stir 10 hours at 100 DEG C to prepare the acrylic acid series polymeric compounds on side chain with acrylic acid series unsaturated bond, i.e. bonding
Agent resin 3.The mean molecule quantity for measuring gained copolymer is 18,000, and it is 1.8 to measure decentralization.
4) preparation of adhesive resin 4
By 62.5g (0.05 mole) 3- (triethoxy silicon substrate) methyl propionate, the second of 51.6g (0.04 mole) bicycloheptyl three
TMOS, 6.8g (0.01 mole) MTMSs and 200g propylene glycol methyl ether acetates are weighed poly- in 500mL
Close container, agitating solution, instill 10.4g (0.02 mole) 35% aqueous hydrochloric acid solution, 47.2g water and 50g tetrahydrofurans it is mixed
Compound.After being added dropwise to complete, reaction temperature is set to increase to 85 DEG C, and reaction is carried out 6 hours at a temperature of increase.Reacting
Cheng Hou, the tetrahydrofuran and methanol of suitable amount are removed by evaporation, add ether and water to be extracted, and reclaim organic phase, and
Remaining alcohol and solvent are removed by evaporation, so as to produce 54g silicone resins.The silicone resin obtained is dissolved in 125.5g
In propylene glycol methyl ether acetate.The weight average molecular weight of the silicone resin obtained is 6,000.
5) adhesive resin 5
CAP-01 (manufacturers：Miwon) it is used as phenolphthalein based binder resin.
Embodiment 1 to 17：The preparation of black matrix" photo-corrosion-resisting agent composition
By according to composition and its content listed in table 1 below, in sequential order by 20wt% adhesive resins 1 to 5,
10wt% dipentaerythritol acrylates, as the 0.5wt% compounds 1 of Photoepolymerizationinitiater initiater, compound 2, compound 3 and
Compound 4, be scattered in propylene glycol methyl ether acetate (Propylene glycol monomethyl ether acetate,
PGMEA the 50wt% carbon blacks in 25wt% solids and the 0.1wt%FC-430 (3M companies) as leveling agent are put into purple in)
In the reaction mixing channel of outside line (ultraviolet, UV) shielding part and agitator, and after being stirred at room temperature, using PGMEA as
Solvent addition amounts to 100wt% compositions to constitute, so as to prepare black matrix" photo-corrosion-resisting agent composition.
[compound 1]
[compound 2]
[compound 3]
[compound 4]
Embodiment 18 to 20：Photo-corrosion-resisting agent composition is prepared to assess for solubility
Added as the compound 1 of Photoepolymerizationinitiater initiater with 1.0wt%, 2.0wt% and 3.0wt% content, in order to survey
Determine solubility, in the state of without carbon black, photoresist group is prepared with composition and stirring means same as Example 2
Compound.
[table 1]
Comparative example 1 to 3：The preparation of black matrix" photo-corrosion-resisting agent composition
The black matrix" photo-corrosion-resisting agent composition of comparative example 1 to 3 is prepared by method same as Example 2, is removed
Use respectively following compound 5, compound 6 and compound 7 as Photoepolymerizationinitiater initiater outside.
[compound 5]
[compound 6]
[compound 7]
Comparative example 4 to 6：Photo-corrosion-resisting agent composition is prepared to assess for solubility
Compound 6 is used as Photoepolymerizationinitiater initiater, and content is respectively 1.0wt%, 2.0wt% and 3.0wt%, molten in order to determine
Xie Du, in the state of without carbon black, photoresist combination is prepared with composition and stirring means same as Example 2
Thing.
[property assessment]
The black matrix" photo-corrosion-resisting agent composition on the glass substrate implementing embodiment 1 to 17 and comparative example 1 to 3 is commented
Estimate, the performance (such as including sensitiveness, pattern properties and sheet resistance) of photo-corrosion-resisting agent composition is shown in table 2 below and is assessed
As a result.
1) sensitiveness
Photoresist is spun on glass substrate, and carries out the pre-heat treatment at 100 DEG C has about for 90 seconds to be formed
1.9 μm thickness film.Using high-pressure sodium lamp with 150 μm of exposing clearance from 20mJ/cm2With 10mJ/cm2Increase and use
Photomask forms pattern, and measures the C.D. (Critical dimension, critical dimension) of pattern.0.04% after exposure
The KOH aqueous solution in developed.Then, progress is cleaned with pure water, dried and rear 30 points of the baking in convection oven at 230 DEG C
Clock is to form black matrix pattern.The sensitiveness of each sample is with C.D. (the Critical dimension, critical chi of pattern
It is very little) size saturation when light exposure indicate.
2) case hardness
After being exposed under the light exposure that sensitivity assessment is determined, the pin hole number formed on the surface of black matrix",
0~3 pin hole is determined as zero in 10mm × 10mm, 3~7 pin holes are determined as △, and 7 and more than 7 pin holes are defined as X.
3) developing process characteristic
Developed after being exposed under the light exposure that sensitivity assessment is determined, and measure developing process scope (BP-BT),
Wherein the developing time of unexposed area is BT, and the splitting time of 10 μm of exposure subregion patterns is BP.
4) reflectivity
Measure coat using spin coater on substrate after black matrix" composition through by prebake, expose and after roasting journey formed
Black matrix" reflectivity.
5) solubility
Blend composition and it is stood at ambient temperature after 48 hours in transparent glass container, carry out to embodiment
18 to 20 and comparative example 4 to 6 in the solubility of prepared composition assess, and dissolved according to the turbidity level determinations of composition
Degree；Splendid solubility is marked with ◎, and good solubility is with zero mark, and bad solubility is marked with X, and result is shown in table 2 below
In.Herein, turbidity can be used as the phenomenon occurred due to following：When there is excessive Photoepolymerizationinitiater initiater, because of solubility reduction
And formed.
[table 2]
| Embodiment | Sensitiveness | Case hardness | Developing process scope (second) | Reflectivity (%) | Solubility |
| 1 | 60 | ○ | 80 | 6.5 | - |
| 2 | 80 | ○ | 60 | 6.7 | - |
| 3 | 90 | △ | 40 | 6.5 | - |
| 4 | 120 | △ | 30 | 6.7 | - |
| 5 | 40 | ○ | 110 | 6.4 | - |
| 6 | 60 | ○ | 70 | 6.4 | - |
| 7 | 60 | ○ | 70 | 6.5 | - |
| 8 | 80 | △ | 50 | 6.3 | - |
| 9 | 40 | ○ | 110 | 6.4 | - |
| 10 | 60 | ○ | 70 | 6.3 | - |
| 11 | 60 | ○ | 70 | 6.4 | - |
| 12 | 80 | △ | 50 | 6.5 | - |
| 13 | 60 | ○ | 100 | 5.8 | - |
| 14 | 80 | ○ | 80 | 5.9 | - |
| 15 | 90 | ○ | 80 | 6.1 | - |
| 16 | 120 | △ | 60 | 6.0 | - |
| 17 | 60 | ○ | 100 | 5.9 | - |
| 18 | <40 | ○ | 100 | - | ◎ |
| 19 | <40 | ○ | 120 | - | ◎ |
| 20 | <40 | ○ | 120 | - | ◎ |
| Comparative example 1 | 150 | X | 10 | 7.4 | - |
| Comparative example 2 | 70 | △ | 70 | 7.8 | - |
| Comparative example 3 | 80 | △ | 70 | 7.2 | - |
| Comparative example 4 | <40 | ○ | 80 | - | ○ |
| Comparative example 5 | <40 | ○ | 90 | - | X |
| Comparative example 6 | <40 | ○ | 100 | - | X |
Claims (7)
1. a kind of black matrix" photo-corrosion-resisting agent composition, being represented by following chemical formula 1 as Photoepolymerizationinitiater initiater is included
Oxime ester fluorene derivative compound：
[chemical formula 1]
In the chemical formula 1,
R1To R3Each of independently be hydrogen atom, halogen atom, (C1-C20) alkyl, (C6-C20) aryl, (C1-C20)
Alkoxy, (C6-C20) aryl (C1-C20) alkyl, hydroxyl (C1-C20) alkyl, hydroxyl (C1-C20) alkoxy (C1-C20) alkane
Base or (C3-C20) cycloalkyl；
A is hydrogen atom, (C1-C20) alkyl, (C6-C20) aryl, (C1-C20) alkoxy, (C6-C20) aryl (C1-C20) alkane
Base, hydroxyl (C1-C20) alkyl, hydroxyl (C1-C20) alkoxy (C1-C20) alkyl, (C3-C20) cycloalkyl, amino, nitro,
Cyano group or hydroxyl；
N is 0 or 1.
2. black matrix" photo-corrosion-resisting agent composition as claimed in claim 1, wherein, the R1To R3Each of it is independent
Ground be bromine atoms, chlorine atom, iodine atom, methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, the tert-butyl group, n-pentyl,
Isopentyl, n-hexyl, isohesyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxyl group, ethyoxyl, positive third
Epoxide, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, hydroxyl are just
Butyl, hydroxyisobutyl, hydroxyl n-pentyl, hydroxyl isopentyl, hydroxyl n-hexyl, hydroxyl isohesyl, hydroxymethoxy methyl, hydroxyl
Ylmethoxy ethyl, hydroxymethoxy propyl group, hydroxymethoxy butyl, hydroxyethoxymethyl, hydroxyl ethoxy ethyl, hydroxyl
Ethoxycarbonyl propyl, hydroxyl-oxethyl butyl, hydroxyethoxypentyl or hydroxyl-oxethyl hexyl.
3. black matrix" photo-corrosion-resisting agent composition as claimed in claim 1, wherein, the composition includes adhesive tree
Fat, the polymerizable compound with ethylenic unsaturated bond, the Photoepolymerizationinitiater initiater and colouring agent of above-mentioned chemical formula 1.
4. black matrix" photo-corrosion-resisting agent composition as claimed in claim 3, wherein, described adhesive resin includes being selected from third
At least one of olefin(e) acid system resin, phenolphthalein base class resin and silicone.
5. black matrix" photo-corrosion-resisting agent composition as claimed in claim 3, wherein, the colouring agent include selected from carbon black,
Titanium is black, at least one of acetylene black, black nigrosine, perylenes, strontium titanates, chromium oxide and cerium oxide.
6. black matrix" photo-corrosion-resisting agent composition as claimed in claim 3, wherein, the bonding based on 100 parts by weight
Agent resin, the content of the colouring agent is 1 to 300 parts by weight.
7. black matrix" photo-corrosion-resisting agent composition as claimed in claim 1, wherein, the composition is also included and is selected from by thiophene
Ton ketone based compound, acetophenone based compound, bisglyoxaline based compound, triazine based compound, mercaptan based compound and except by changing
One or more additional photopolymerization in the group that O- acyl group oxime compounds beyond the compound that formula 1 is represented are constituted trigger
Agent.
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| KR10-2014-0157328 | 2014-11-12 | ||
| KR20140157328 | 2014-11-12 | ||
| PCT/KR2015/012191 WO2016076652A1 (en) | 2014-11-12 | 2015-11-12 | Black matrix photoresist composition for liquid crystal display panel |
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| JP6533556B2 (en) * | 2016-05-24 | 2019-06-19 | 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． | Photosensitive resin composition and photocurable pattern produced therefrom |
| TWI635079B (en) * | 2016-07-08 | 2018-09-11 | 韓國化學研究院 | Highly sensitive oxime ester photopolymerization initiator and photopolymerizable composition including the same |
| KR102011090B1 (en) * | 2016-09-19 | 2019-08-14 | 동우 화인켐 주식회사 | Colored photosensitive resin composition, color filter and image display device produced using the same |
| KR102615683B1 (en) * | 2016-11-16 | 2023-12-18 | 동우 화인켐 주식회사 | Photosensitive resin composition and photo-cured pattern formed from the same |
| KR101848567B1 (en) * | 2016-11-18 | 2018-04-12 | 롬엔드하스전자재료코리아유한회사 | Colored photosensitive resin composition and light shielding spacer prepared therefrom |
| KR101834209B1 (en) * | 2016-11-25 | 2018-03-06 | 주식회사 삼양사 | Photopolymerization initiators and photosensitive resin composition for light shield comprising the same |
| KR101840584B1 (en) * | 2017-01-17 | 2018-03-20 | 동우 화인켐 주식회사 | Colored Photosensitive Resin Composition, Color Filter and Display Device |
| KR102246858B1 (en) * | 2017-03-30 | 2021-04-30 | 동우 화인켐 주식회사 | Colored photo sensitive resin composition, a color filter comprising the same, and a display device comprising the color filter |
| KR102420415B1 (en) * | 2017-10-17 | 2022-07-15 | 덕산네오룩스 주식회사 | Adhesion enhanced photo sensitive resin composition and light blocking layer using the same |
| CN114127637A (en) * | 2019-07-12 | 2022-03-01 | 株式会社三养社 | Photosensitive resin composition |
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| KR20160056836A (en) | 2016-05-20 |
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