CN117369211A - Resin composition, cured film, and color filter - Google Patents
Resin composition, cured film, and color filter Download PDFInfo
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- CN117369211A CN117369211A CN202210756079.5A CN202210756079A CN117369211A CN 117369211 A CN117369211 A CN 117369211A CN 202210756079 A CN202210756079 A CN 202210756079A CN 117369211 A CN117369211 A CN 117369211A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 93
- 229920005989 resin Polymers 0.000 claims abstract description 75
- 239000011347 resin Substances 0.000 claims abstract description 75
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000000178 monomer Substances 0.000 claims abstract description 45
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000003086 colorant Substances 0.000 claims abstract description 19
- 239000003999 initiator Substances 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005977 Ethylene Substances 0.000 claims abstract description 6
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 acryl group Chemical group 0.000 claims description 16
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 13
- 239000006229 carbon black Substances 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 10
- 125000000962 organic group Chemical group 0.000 claims description 9
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052719 titanium Inorganic materials 0.000 claims description 8
- 239000010936 titanium Substances 0.000 claims description 8
- 125000005641 methacryl group Chemical group 0.000 claims description 6
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 claims description 5
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 claims description 4
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000000576 coating method Methods 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- 229920002160 Celluloid Polymers 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- FVEGJIRNDFKKMX-UHFFFAOYSA-N 1-(4-bromophenyl)-9h-fluorene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C12 FVEGJIRNDFKKMX-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- NARFILZKWWKCHH-UHFFFAOYSA-N 2-chloro-4-(9H-fluoren-1-yl)aniline Chemical compound ClC=1C=C(C=CC=1N)C1=CC=CC=2C3=CC=CC=C3CC1=2 NARFILZKWWKCHH-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- HVSOOROWXIVZSH-UHFFFAOYSA-N 4-(9H-fluoren-1-yl)-2-fluoroaniline Chemical compound NC1=C(C=C(C=C1)C1=CC=CC=2C3=CC=CC=C3CC1=2)F HVSOOROWXIVZSH-UHFFFAOYSA-N 0.000 description 1
- KCIVBLNHLBBZFE-UHFFFAOYSA-N 4-(9h-fluoren-1-yl)-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C=2C3=C(C4=CC=CC=C4C3)C=CC=2)=C1 KCIVBLNHLBBZFE-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
Abstract
The invention provides a resin composition, a cured film and a color filter. The resin composition comprises a resin (A), a polymerizable monomer (B), a photopolymerization initiator (C), a photoacid generator (D), a black colorant (E) and a solvent (F). The resin (A) includes an alkali-soluble resin (A-1) and a styrene resin (A-2). The alkali-soluble resin (A-1) has a weight average molecular weight of 2,000 to 20,000 and comprises a structural unit having a fluorene ring and two or more ethylene polymerizable groups. The polymerizable monomer (B) includes a urethane acrylate oligomer (B-1).
Description
Technical Field
The present invention relates to a resin composition, and more particularly, to a resin composition, a cured film, and a color filter.
Background
The panel outer frame of the display device is provided with a light shielding film for blocking light leakage at the periphery of the panel to inhibit light leakage when the picture is displayed as black and inhibit the problem of color mixing between adjacent color filter patterns. At present, the light-shielding property of the light-shielding film is often improved by increasing the concentration of black pigment in the light-shielding film. However, increasing the concentration of black pigment in the light shielding film may cause problems such as blurring of the mask pattern, development residue, and deterioration of reactivity during development, thereby affecting the performance of the device using the same.
Disclosure of Invention
The invention provides a resin composition, a cured film and a color filter which can form a resin composition with good resolution, light-shielding property and adhesion and is not easy to cause undercut problem.
A resin composition of the present invention comprises a resin (A), a polymerizable monomer (B), a photopolymerization initiator (C), a photoacid generator (D), a black colorant (E), and a solvent (F). The resin (A) includes an alkali-soluble resin (A-1) and a styrene resin (A-2). The alkali-soluble resin (A-1) has a weight average molecular weight of 2,000 to 20,000 and comprises a structural unit having a fluorene ring and two or more ethylene polymerizable groups. The polymerizable monomer (B) includes a urethane acrylate oligomer (B-1).
In one embodiment of the present invention, the above-mentioned structural unit having a fluorene ring and two or more ethylene polymerizable groups comprises a structural unit represented by the following formula (A1):
in formula (A1), the bonding position is represented.
In one embodiment of the present invention, the styrene resin (A-2) comprises a structural unit represented by the following formula (A2):
in the formula (A2), p represents an integer of 20 to 50, and x represents a bonding position.
In one embodiment of the present invention, the urethane acrylate oligomer (B-1) includes a structural unit represented by the following formula (B1) or a structural unit derived from a compound represented by the following formula (B2):
in the formula (B1), R 1 R is R 2 Respectively represents a divalent organic group, q represents an integer of 5 to 20, and x represents a bonding position;
in the formula (B2), X 1 ～X 10 Respectively represents a hydrogen atom, an acryl group or a methacryl group, wherein X 1 ～X 10 At least two of which are acryl or methacryl.
In an embodiment of the invention, the polymerizable monomer (B) further comprises a triazine monomer (B-2).
In one embodiment of the present invention, the polymerizable monomer (B) further comprises a triazine-based monomer (B-2) represented by the following formula (B3):
in the formula (B3), R 3 To R 8 Respectively represent alkyl groups with carbon numbers of 1-6.
In one embodiment of the present invention, the photopolymerization initiator (C) includes an oxime ester compound.
In an embodiment of the invention, the photoacid generator (D) includes a propane sulfonic acid compound.
In one embodiment of the present invention, the black colorant (E) comprises carbon black (E-1), titanium black (E-2), or a combination thereof.
In one embodiment of the present invention, the carbon black (E-1) is used in an amount of 10 to 40 parts by weight and the titanium black (E-2) is used in an amount of 30 to 70 parts by weight, based on 100 parts by weight of the above-mentioned resin composition.
In an embodiment of the present invention, the solvent (F) includes propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether, or a combination thereof.
In an embodiment of the present invention, the resin composition further includes a surfactant (G). The surfactant (G) includes a fluorine-based surfactant, a silicone-based surfactant, a nonionic surfactant, or a combination thereof.
In one embodiment of the present invention, based on 100 parts by weight of the above-mentioned resin composition, the resin (a) is used in an amount of 6 to 40 parts by weight, the polymerizable monomer (B) is used in an amount of 2 to 40 parts by weight, the photopolymerization initiator (C) is used in an amount of 0.01 to 10 parts by weight, the photoacid generator (D) is used in an amount of 0.01 to 10 parts by weight, the black colorant (E) is used in an amount of 40 to 88 parts by weight, and the solvent (F) is used in an amount of 0.1 to 20 parts by weight.
The cured film of the present invention is cured from the above resin composition.
A color filter of the present invention includes a black matrix. The black matrix is cured from the above resin composition.
Based on the above, the resin composition of the present invention comprises a resin (A) and a polymerizable monomer (B), the resin (A) comprises an alkali-soluble resin (A-1) and a styrene resin (A-2), the alkali-soluble resin (A-1) comprises structural units of a specific structure, and the polymerizable monomer (B) comprises a urethane acrylate oligomer (B-1). Therefore, the hardened film formed by the resin composition has good resolution, light-shielding property and adhesion and does not have undercut problem, and is suitable for a black matrix and a color filter comprising the same.
In order that the manner in which the above recited features and advantages of the invention are obtained will become more readily apparent, a more particular description of the invention briefly described above will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
Drawings
FIG. 1 is a schematic diagram of the invention for evaluating the degree of undercut.
Description of the reference numerals
100: a substrate;
110: a pattern;
112: a sidewall;
θ: and an included angle.
Detailed Description
< resin composition >
The invention provides a resin composition, which comprises a resin (A), a polymerizable monomer (B), a photopolymerization initiator (C), a photoacid generator (D), a black colorant (E) and a solvent (F). In addition, the resin composition of the present invention may further include a surfactant (G) as needed. Hereinafter, the above-described various components will be described in detail.
It is explained here that, in this context, a so-called "tetravalent organic group" is an organic group having four bonding positions, and that the "tetravalent organic group" can form four chemical bonds via these four bonding positions.
Herein, a "divalent organic group" is an organic group having two bonding positions, and the "divalent organic group" may form two chemical bonds via the two bonding positions.
Resin (A)
The resin (A) includes an alkali-soluble resin (A-1) and a styrene resin (A-2). The resin (a) may further include other suitable resins.
The weight average molecular weight of the alkali-soluble resin (A-1) is 2,000 to 20,000, preferably 4,000 to 10,000. The alkali-soluble resin (A-1) comprises a fluorene ring and at least two vinyl polymerizable groups. In this embodiment, the structural unit having a fluorene ring and two or more ethylenically polymeric groups may include a structural unit represented by the following formula (A1):
in formula (A1), the bonding position is represented.
In addition, the structural unit represented by the formula (A1) is derived from a monomer represented by the following formula (A1-1).
The alkali-soluble resin (A-1) may be a cardo resin formed by polymerizing a monomer having a fluorene ring and two or more ethylenically polymerizable groups, a tetracarboxylic dianhydride, and a dicarboxylic acid, and the monomer having a fluorene ring and two or more ethylenically polymerizable groups is preferably a monomer represented by the above formula (A1-1). The tetracarboxylic dianhydride and the dicarboxylic acid are not particularly limited, and suitable tetracarboxylic dianhydride and dicarboxylic acid may be selected according to the need. For example, the compound forming the structural unit having a fluorene ring and two or more ethylenically polymeric groups may include bisphenol fluorene compounds having two or more ethylenically polymeric groups obtained by reacting bisphenol fluorene compounds with ethylenically unsaturated compounds. The bisphenol fluorene-based compound may include 9, 9-bis (4-hydroxyphenyl) fluorene, 9-bis (4-hydroxy-3-methylphenyl) fluorene, 9-bis (4-amino-3-chlorophenyl) fluorene, 9-bis (4-bromophenyl) -9H-fluorene, 9-bis (4-amino-3-fluorophenyl) fluorene or other suitable bisphenol fluorene-based compound. The method for synthesizing the alkali-soluble resin (A-1) is not particularly limited, and a monomer having a fluorene ring and two or more ethylene polymerizable groups, a tetracarboxylic dianhydride and a dicarboxylic acid may be polymerized into a structural unit having a fluorene ring and two or more ethylene polymerizable groups by a conventional organic synthesis method.
Specific examples of the alkali-soluble resin (A-1) include a card poly (cardo) resin (trade name CX-01, manufactured by Takoma Corp., TAKOMA Ltd.).
The alkali-soluble resin (A-1) is used in an amount of 5 to 20 parts by weight, preferably 7 to 9 parts by weight, based on 100 parts by weight of the resin composition.
When the alkali-soluble resin (A-1) is included in the resin composition, the cured film formed from the resin composition may have a preferable adhesion.
The styrene resin (A-2) is not particularly limited, and an appropriate styrene resin may be selected according to the need. For example, the styrene resin (A-2) may include a styrene resin or other suitable styrene resin. The styrene resin (A-2) may be one kind of styrene resin or may be a combination of plural kinds of styrene resins. In this embodiment, the styrene resin (a-2) may include a structural unit represented by the following formula (A2):
in the formula (A2), p represents an integer of 20 to 50, preferably an integer of 25 to 45; * Indicating the bonding position.
The styrene resin (A-2) is used in an amount of 1 to 20 parts by weight, preferably 2 to 3 parts by weight, based on 100 parts by weight of the resin composition.
The resin (a) is used in an amount of 6 to 40 parts by weight, preferably 10 to 11 parts by weight, based on 100 parts by weight of the resin composition.
Polymerizable monomer (B)
The polymerizable monomer (B) includes a urethane acrylate oligomer (B-1). In this embodiment, the polymerizable monomer (B) may further include a triazine-based monomer (B-2) or other suitable polymerizable monomer.
The urethane acrylate oligomer (B-1) is not particularly limited, and an appropriate urethane acrylate oligomer may be selected according to the need. For example, the urethane acrylate oligomer (B-1) may include urethane acrylate oligomer (trade name DPHA-40H, manufactured by Nippon Kagaku Co., ltd.) or other suitable urethane acrylate oligomer. The urethane acrylate oligomer (B-1) may be one structural unit or may be a combination of a plurality of structural units. In this embodiment, the urethane acrylate oligomer (B-1) includes a structural unit represented by the following formula (B1) or a structural unit derived from a compound represented by the following formula (B2).
In the formula (B1), R 1 R is R 2 Each represents a divalent organic group, q represents an integer of 5 to 20, and q represents a bonding position.
In the formula (B1), R 1 R is R 2 Preferably an alkylene group having 4 to 12 carbon atoms or an alkyleneoxy group having 4 to 12 carbon atoms, more preferably an alkyleneoxy group having 2 to 7 carbon atoms; q is preferably an integer of 7 to 15.
In the formula (B2), X 1 ～X 10 Respectively represents a hydrogen atom, an acryl group or a methacryl group,wherein X is 1 ～X 10 At least two of which are acryl or methacryl.
In the formula (B2), X 1 ～X 10 Preferably acryl groups, respectively.
The urethane acrylate oligomer (B-1) is used in an amount of 1 to 20 parts by weight, preferably 2 to 4 parts by weight, based on 100 parts by weight of the resin composition.
The triazine monomer (B-2) is not particularly limited, and an appropriate triazine monomer may be selected according to the need. In this embodiment, the triazine-based monomer (B-2) may include melamine-based monomers (e.g., CYMEL (trade name, manufactured by allnex) or other suitable triazine-based monomers. The triazine monomer (B-2) may be used alone or in combination of two or more.
In this embodiment, the triazine-based monomer (B-2) may include a compound represented by the following formula (B3):
in the formula (B3), R 3 To R 8 Each represents an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms.
The triazine-based monomer (B-2) is used in an amount of 1 to 20 parts by weight, preferably 1 to 3 parts by weight, based on 100 parts by weight of the resin composition.
The polymerizable monomer (B) is used in an amount of 2 to 40 parts by weight, preferably 4 to 5 parts by weight, based on 100 parts by weight of the resin composition.
Photopolymerization initiator (C)
The photopolymerization initiator (C) is not particularly limited, and an appropriate photopolymerization initiator may be selected according to the need. In the present embodiment, the photopolymerization initiator (C) may include an oxime ester-based compound or other suitable photopolymerization initiator. The oxime ester-based compound may include Irgacure OXE-03 (trade name, manufactured by Basf) or other suitable oxime ester-based compounds. The photopolymerization initiator (C) may be used alone or in combination of two or more. In this embodiment, the photopolymerization initiator (C) is preferably a brilliant solid OXE-03.
The photopolymerization initiator (C) is used in an amount of 0.01 to 10 parts by weight, preferably 0.5 to 1.5 parts by weight, more preferably 0.7 to 1.1 parts by weight, based on 100 parts by weight of the resin composition.
Photoacid generator (D)
The photoacid generator (D) is not particularly limited, and an appropriate photoacid generator may be selected according to the need. In this embodiment, the photoacid generator (D) may include a propane sulfonic acid-based compound or other suitable photoacid generator. The propane sulfonic acid-based compound may include Irgacure (Irgacure) PAG 103 (commercially available from Basf corporation) or other suitable propane sulfonic acid-based compounds. The photoacid generator (D) may be used alone or in combination of two or more.
The photoacid generator (D) is used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 0.15 parts by weight, more preferably 0.09 to 0.13 parts by weight, based on 100 parts by weight of the resin composition.
The sum of the amount of the photopolymerization initiator (C) and the amount of the photoacid generator (D) is 1 to 50 parts by weight, preferably 10 to 15 parts by weight, based on 100 parts by weight of the alkali-soluble resin (A-1).
Black colorant (E)
The black colorant (E) is not particularly limited, and an appropriate black colorant may be selected according to the need. In this embodiment, the black colorant (E) may comprise carbon black (E-1), titanium black (E-2), or a combination thereof. The black colorant (E) may be used alone or in combination of two or more. In this embodiment, the black colorant (E) is preferably a combination of carbon black (E-1) and titanium black (E-2).
The black colorant (E) is used in an amount of 40 to 88 parts by weight, preferably 83 to 84 parts by weight, based on 100 parts by weight of the resin composition.
The carbon black (E-1) is used in an amount of 10 to 40 parts by weight, preferably 22 to 34 parts by weight, based on 100 parts by weight of the resin composition; and titanium black (E-2) is used in an amount of 30 to 70 parts by weight, preferably 58 to 59 parts by weight.
Solvent (F)
The solvent (F) is not particularly limited, and an appropriate solvent may be selected according to the need. For example, the solvent (F) may include glycol ether compounds, acetate compounds, or other suitable solvents. The glycol ether compound may include celluloid, methyl celluloid, ethyl celluloid, carbitol, methyl carbitol, ethyl carbitol, butyl carbitol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, or other suitable glycol ether compounds. The acetate compounds may include ethyl acetate, butyl acetate, celluloid Su Yisuan ester, ethyl celluloid Su Yisuan ester, butyl celluloid Su Yisuan ester, carbitol acetate, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether acetate (propylene glycol methyl ether acetate, PGMEA), dipropylene glycol monomethyl ether acetate, or other suitable acetate compounds. The solvent (F) may be used alone or in combination of two or more. In the present embodiment, the solvent (F) is preferably propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether or a combination thereof, more preferably propylene glycol monomethyl ether acetate.
The solvent (F) is used in an amount of 0.1 to 20 parts by weight, preferably 0.5 to 1.5 parts by weight, more preferably 0.6 to 1.1 parts by weight, based on 100 parts by weight of the resin composition.
When the resin composition includes the solvent (F), the resin composition may be made to have an appropriate viscosity, thereby having good coating uniformity, to form a hardened film having good surface flatness.
Surfactant (G)
The surfactant (G) is not particularly limited, and an appropriate surfactant may be selected according to the need. For example, the surfactant (G) may include a fluorine-based surfactant, a silicone-based surfactant, a nonionic-based surfactant, or other suitable surfactant. The surfactant (G) may be used alone or in combination of two or more.
The surfactant (G) is used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 0.15 parts by weight, based on 100 parts by weight of the total amount of the resin compositions.
< method for producing resin composition >
The method for producing the resin composition is not particularly limited. For example, the resin (a), the polymerizable monomer (B), the photopolymerization initiator (C), the photoacid generator (D), the black colorant (E), and the solvent (F) are placed in a stirrer and stirred to be uniformly mixed into a solution state, and if necessary, the surfactant (G) may be added to be uniformly mixed to obtain a liquid resin composition.
< method for producing cured film >
An exemplary embodiment of the present invention provides a cured film formed using the above resin composition.
The cured film may be formed by coating the above resin composition on a substrate to form a coating film, and subjecting the coating film to pre-baking (prebake), exposure, development, and post-baking (postrake). For example, after the resin composition is coated on the substrate to form a coating film, a baking (i.e., pre-baking) step before exposure is performed at a temperature of 90 ℃ for 2 minutes. Next, an I line stepper is used at a speed of 400 to 1200J/m 2 Exposing the pre-baked coating film to light. Then, the exposed coating film was developed for 24 seconds. Then, the developed coating film was washed with distilled water and nitrogen gas was blown to dry the coating film. Then, post-baking was performed at 220℃for 20 minutes to form a cured film having a thickness of about 1.5. Mu.m on the substrate.
The substrate may be a glass substrate, a plastic substrate material such as a Polyethersulfone (PES) plate, a Polycarbonate (PC) plate, or a Polyimide (PI) film, or other light-permeable substrate, the type of which is not particularly limited.
The coating method is not particularly limited, but a spray coating method, a roll coating method, a spin coating method, or the like can be used, and in general, a spin coating method is widely used. Further, a coating film is formed, and then in some cases, the residual solvent may be partially removed under reduced pressure.
The developer is not particularly limited, and an appropriate developer may be selected according to the need. For example, the developer may be tetramethyl amine hydroxide (tetramethyl ammonium hydroxide, TMAH) at a concentration of 0.3 wt.%.
In this example, the hardened film having a thickness of 1.0 to 1.5 μm has a transmittance of less than 0.4% at a wavelength of 300 to 1100 nm.
< color Filter >
An exemplary embodiment of the present invention provides a color filter including a black matrix. The black matrix is cured from the above resin composition. The color filter may further include a filter pattern. The filter patterns may include red filter patterns, green filter patterns, and blue filter patterns. The black matrix may be disposed between the respective filter patterns.
The cured film or the color filter according to an exemplary embodiment of the invention has a specific transmittance in the visible light region, and can be applied to devices such as CMOS image sensors (CMOS Image Sensor; CIS), solid-state imaging devices, integrated circuit (Integrated circuit, IC) semiconductors, light emitting diodes, liquid crystal displays, and the like.
Hereinafter, the present invention will be described in detail with reference to examples. The following examples are provided to describe the invention and the scope of the invention includes the scope of the claims and their substitutes and modifications, and is not limited to the scope of the examples.
Examples of resin compositions and cured films
Examples 1 to 4 and comparative examples 1 to 4 of the resin composition and the cured film are described below:
example 1
a. Resin composition
7.846 parts by weight of a cado resin (trade name CX-01, manufactured by Takema Co., ltd.), 2.234 parts by weight of a styrene resin (A-2) comprising a structural unit represented by the formula (A2), 2.670 parts by weight of DPHA-40H (trade name, manufactured by Japanese chemical Co., ltd.), 2.320 parts by weight of a triazine-based monomer (B-2) represented by the formula (B3), 1.032 parts by weight of an oxime-based compound represented by the formula (C1), 0.124 parts by weight of a propane sulfonic acid-based compound represented by the formula (D1), 25 parts by weight of carbon black and 58.14 parts by weight of titanium black were added to 0.634 parts by weight of Propylene Glycol Monomethyl Ether Acetate (PGMEA), and stirred uniformly by a stirrer, to obtain a resin composition of example 1.
b. Cured film
Each of the resin compositions obtained in the examples was applied to a substrate by spin coating (spin coater model MK-VIII, manufactured by Tokyo Wisco Co., ltd. (Tokyo Electron Limited, TEL) at a rotation speed of about 600 rpm). Next, pre-baking was performed at a temperature of 90℃for 2 minutes to form a film. Then, an I-line stepper (model 5500iZa, manufactured by Canon Co., ltd.) was used at a speed of 400 to 1200J/m 2 Exposing the pre-baked coating film to light to form a semi-finished product. Then, development was performed at a temperature of 23 ℃ for 24 seconds with TMAH having a concentration of 0.3 wt% as a developer. Then, the developed coating film was washed with distilled water and nitrogen gas was blown to dry the coating film. Then, post-baking was performed at 220℃for 20 minutes to obtain a cured film having a pattern thickness of 1.5. Mu.m. The cured films thus obtained were evaluated in the following manner, and the results are shown in table 2.
Examples 2 to 4 and comparative examples 1 to 4
The resin compositions of examples 2 to 4 and comparative examples 1 to 4 were prepared in the same procedure as in example 1, and they were different in that: the kinds of components of the resin composition and the amounts thereof used were changed (as shown in Table 2), wherein the components/compounds corresponding to the numbers in Table 2 are shown in Table 1. The cured films of the obtained resin compositions were evaluated in the following manner, and the results are shown in table 2.
TABLE 1
/>
TABLE 2
< evaluation mode >
a. Resolution ratio
The prepared hardened film (thickness of 1.5 μm) was observed for the integrity of dot patterns in the region of 5.0 μm in critical dimension at a magnification of 12000 times by a critical dimension scanning electron microscope (Critical Dimension Scanning Electron Microscope, CD-SEM) (model S8840, manufactured by HITACHI (HITACHI) inc.) to evaluate the resolution. The hardened film was shown to have good resolution as the pattern profile was more complete.
The evaluation criteria for the resolution are as follows:
o: the outline of the pattern is complete;
delta: the outline of the pattern is slightly convex or unfilled, but the actual application is not affected;
and (3) the following steps: the pattern profile is incomplete.
b. Light-shielding property
The light-shielding property was evaluated by measuring the transmittance of the prepared cured film (thickness: 1.5 μm) at a wavelength of 300nm to 1100nm on the film by means of an ultraviolet-visible light spectrometer (UV-VIS spectrometers) (model U2900, manufactured by Hitachi Co., ltd.). The cured film showed good light-shielding properties as the transmittance was lower.
The evaluation criteria for light shielding properties were as follows:
o: the penetration rate is less than 0.4%;
delta: 0.4% +.ltoreq.penetration < 1.0%;
and (3) the following steps: 1.0% or less.
c. Adhesion to
The prepared cured film (thickness 1.5 μm) was inspected for the smallest dimension of the pattern width at which the pattern did not peel off by an optical microscope (Optical Microscope, OM) (model BH3-SIC6, manufactured by Olympus) under magnification of 500 times to evaluate the adhesion. The smaller the width when the pattern is not peeled off, the better the adhesion of the cured film is.
The evaluation criteria for adhesion were as follows:
o: pattern width < 10 μm;
delta: pattern width of 10 μm or less than 20 μm;
and (3) the following steps: 20 μm.
d. Degree of undercut
The prepared hardened film (thickness of 1.5 μm) was observed at a magnification of 12000 times by a scanning electron microscope (Scanning Electron Microscope, SEM) (model SU8010, manufactured by hitachi limited) at an angle of θ (as shown in fig. 1) between the sidewall 112 of the pattern 110 and the substrate 100 to evaluate the undercut degree. The closer the angle is to 90 degrees, the less undercut the hardened film is.
The evaluation criteria for the degree of undercut are as follows:
o: 85 degrees +.θ;
delta: 65 degrees is less than or equal to θ < 85 degrees;
and (3) the following steps: θ < 65 degrees.
< evaluation results >
As can be seen from table 2, when the resin composition comprises the resin (a) and the polymerizable monomer (B), the resin (a) comprises the alkali-soluble resin (a-1) and the styrene resin (a-2), the alkali-soluble resin (a-1) comprises structural units of a specific structure, and the polymerizable monomer (B) comprises the urethane acrylate oligomer (B-1) (examples 1 to 4), the cured film formed by the resin composition has both good resolution, light shielding property, adhesion and no undercut problem, and is applicable to a black matrix and a color filter comprising the same.
In contrast, when the resin composition does not include the alkali-soluble resin (a-1) including the structural unit of the specific structure (comparative example 1), the resolution and the adhesion of the cured film formed by the resin composition are poor, and undercut problems occur; when the resin composition does not include the urethane acrylate oligomer (B-1) (comparative example 2), the cured film formed by the resin composition exhibits an undercut problem; when the resin composition does not include the styrene resin (a-2) (comparative example 3), the cured film formed by the resin composition exhibits an undercut problem; when the resin composition does not contain carbon black (comparative example 4), the light-shielding property and the adhesion property of the cured film formed from the resin composition are not good, and it is not possible to simultaneously achieve good resolution, light-shielding property, adhesion property and no undercut problem.
In addition, the cured films (examples 1 to 4) formed from the resin composition containing the alkali-soluble resin (a-1) having the structural unit of the specific structure had better resolution and adhesion and did not have undercut problems than the cured film (comparative example 1) formed from the resin composition containing the alkali-soluble resin (a-1) not including the structural unit of the specific structure. From this, it is understood that when the resin (a) includes the alkali-soluble resin (a-1) having a structural unit of a specific structure, the cured film formed from the resin composition can have better resolution and adhesion, and does not have undercut problems.
In addition, the cured films (examples 1 to 4) formed from the resin composition including the urethane acrylate oligomer (B-1) did not have an undercut problem as compared with the cured film (comparative example 2) formed from the resin composition including the urethane acrylate oligomer (B-1) but not including the urethane acrylate oligomer (B-1) as the polymerizable monomer (B) in the resin composition. From this, it is understood that when the polymerizable monomer (B) includes the urethane acrylate oligomer (B-1), the cured film formed from the resin composition may not have an undercut problem.
In addition, the cured films (examples 1 to 4) formed from the resin composition including the styrene resin (a-2) did not have an undercut problem as compared with the cured film (comparative example 3) formed from the resin composition including the styrene resin (a-2) not including the resin (a) in the resin composition. From this, it is understood that when the resin (a) includes the styrene resin (a-2), the cured film formed of the resin composition may not have an undercut problem.
In addition, the cured films (examples 1 to 4) formed from the resin compositions containing the black colorant (E-1) had better light-shielding properties and adhesion properties than the cured films (comparative example 4) formed from the resin compositions containing the black colorant (E) containing no carbon black (E-1). From this, it is understood that when the black colorant (E) includes carbon black (E-1), the cured film formed from the resin composition can have a preferable light-shielding property and adhesion.
In summary, the resin composition of the present invention comprises a resin (a) and a polymerizable monomer (B), wherein the resin (a) comprises an alkali-soluble resin (a-1) and a styrene resin (a-2), the alkali-soluble resin (a-1) comprises structural units of a specific structure, and the polymerizable monomer (B) comprises a urethane acrylate oligomer (B-1), so that a cured film formed from the resin composition has good resolution, light shielding property, adhesion and no undercut problem, and is suitable for a black matrix and a color filter comprising the same, thereby improving the performance of a device using the black matrix and the color filter.
Although the present invention has been described with reference to the above embodiments, it should be understood that the invention is not limited thereto, but rather is capable of modification and variation without departing from the spirit and scope of the present invention.
Claims (15)
1. A resin composition comprising:
a resin (A) comprising an alkali-soluble resin (A-1) and a styrene resin (A-2), the alkali-soluble resin (A-1) having a weight average molecular weight of 2,000 to 20,000 and comprising a structural unit having a fluorene ring and two or more ethylene-based polymerizable groups;
a polymerizable monomer (B) comprising a urethane acrylate oligomer (B-1);
a photopolymerization initiator (C);
photoacid generator (D);
a black colorant (E); and
solvent (F).
2. The resin composition according to claim 1, wherein the structural unit having a fluorene ring and two or more ethylenically polymerizable groups comprises a structural unit represented by the following formula (A1):
in formula (A1), the bonding position is represented.
3. The resin composition according to claim 1, wherein the styrene resin (a-2) comprises a structural unit represented by the following formula (A2):
in the formula (A2), p represents an integer of 20 to 50, and x represents a bonding position.
4. The resin composition according to claim 1, wherein the urethane acrylate oligomer (B-1) comprises a structural unit represented by the following formula (B1) or a structural unit derived from a compound represented by the following formula (B2):
in the formula (B1), R 1 R is R 2 Respectively represents a divalent organic group, q represents an integer of 5 to 20, and x represents a bonding position;
in the formula (B2), X 1 ～X 10 Respectively represents a hydrogen atom, an acryl group or a methacryl group, wherein X 1 ～X 10 At least two of which are acryl or methacryl.
5. The resin composition according to claim 1, wherein the polymerizable monomer (B) further comprises a triazine-based monomer (B-2).
6. The resin composition according to claim 1, wherein the polymerizable monomer (B) further comprises a triazine-based monomer (B-2) represented by the following formula (B3):
in the formula (B3), R 3 To R 8 Respectively represent alkyl groups with carbon numbers of 1-6.
7. The resin composition according to claim 1, wherein the photopolymerization initiator (C) comprises an oxime ester compound.
8. The resin composition according to claim 1, wherein the photoacid generator (D) comprises a propane sulfonic acid-based compound.
9. The resin composition of claim 1, wherein the black colorant (E) comprises carbon black (E-1), titanium black (E-2), or a combination thereof.
10. The resin composition according to claim 9, wherein the carbon black (E-1) is used in an amount of 10 to 40 parts by weight and the titanium black (E-2) is used in an amount of 30 to 70 parts by weight, based on 100 parts by weight of the resin composition.
11. The resin composition of claim 1, wherein the solvent (F) comprises propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether, or a combination thereof.
12. The resin composition of claim 1, further comprising a surfactant (G), wherein the surfactant (G) comprises a fluorine-based surfactant, a silicone-based surfactant, a nonionic-based surfactant, or a combination thereof.
13. The resin composition according to claim 1, wherein the resin (a) is used in an amount of 6 to 40 parts by weight, the polymerizable monomer (B) is used in an amount of 2 to 40 parts by weight, the photopolymerization initiator (C) is used in an amount of 0.01 to 10 parts by weight, the photoacid generator (D) is used in an amount of 0.01 to 10 parts by weight, the black colorant (E) is used in an amount of 40 to 88 parts by weight, and the solvent (F) is used in an amount of 0.1 to 20 parts by weight, based on 100 parts by weight of the resin composition.
14. A cured film cured from the resin composition according to any one of claims 1 to 13.
15. A color filter comprising a black matrix cured from the resin composition according to any one of claims 1 to 13.
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