KR20140076750A - Photosensitive resin composition for color filter, and color filter using the same - Google Patents
Photosensitive resin composition for color filter, and color filter using the same Download PDFInfo
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- KR20140076750A KR20140076750A KR1020120145120A KR20120145120A KR20140076750A KR 20140076750 A KR20140076750 A KR 20140076750A KR 1020120145120 A KR1020120145120 A KR 1020120145120A KR 20120145120 A KR20120145120 A KR 20120145120A KR 20140076750 A KR20140076750 A KR 20140076750A
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- color filter
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- IGUATTIKISNSQD-UHFFFAOYSA-N CC(C)c1cccc(C(C)C)c1N(C(c1ccc(-c(c2c3c(C(N4c5c(C(C)C)cccc5C(C)C)=O)c5)ccc3C4=O)c3c1c1ccc3-c2c5Sc2ccc(C(C)(C)C)cc2)=O)C1=O Chemical compound CC(C)c1cccc(C(C)C)c1N(C(c1ccc(-c(c2c3c(C(N4c5c(C(C)C)cccc5C(C)C)=O)c5)ccc3C4=O)c3c1c1ccc3-c2c5Sc2ccc(C(C)(C)C)cc2)=O)C1=O IGUATTIKISNSQD-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
- C09B69/102—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye containing a perylene dye
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
Abstract
Description
The present invention relates to a photosensitive resin composition for a color filter and a color filter using the same.
Recently, as the spread of the large-screen liquid crystal display device has expanded, a demand for a new performance enhancement for the liquid crystal display device has been increasing. Among the components of the liquid crystal display device, the color filter is the most important color realizing device. Research is continuing. In addition, in the case of a liquid crystal display device having a large screen, the colorant concentration of the photosensitive resin composition for a color filter is increased during the manufacture of a color filter in order to increase color purity. In order to increase productivity and yield in the production process, There is a demand for a photosensitive resin composition for a filter.
The color filter using the photosensitive resin composition for a color filter can be produced by coating three or more kinds of hues on a transparent substrate mainly by a dyeing method, an electrodeposition method, a printing method, a pigment dispersion method, etc. Recently, have.
However, the color filter manufactured by the pigment dispersion method has a limit of luminance and contrast ratio resulting from the size of the pigment particle.
On the other hand, the image sensor refers to a component of a video image pickup device that generates an image from a mobile phone camera or a digital still camera (DSC). The image sensor is classified into a charge coupled device (CCD) image sensor And complementary metal oxide semiconductor (CMOS) image sensors. The pattern size of the color filter mounted on the color image pickup device used for the solid-state image pickup device or the complementary metal oxide semiconductor is 1/100 to 1/200 times that of the color filter pattern for a liquid crystal display device. Accordingly, the increase of the resolution and the reduction of the residue are important items that determine the performance of the device.
In order to be used for an image sensor as such, a photosensitive resin composition for a color filter made of smaller particles is required for forming a fine pattern of a color filter.
An embodiment of the present invention is to provide a photosensitive resin composition for a color filter having high solubility and excellent chemical resistance.
Another embodiment of the present invention is to provide a color filter manufactured using the photosensitive resin composition for a color filter.
(A) a colorant comprising a perylene dye represented by the following formula (1); (B) an acrylic binder resin; (C) a photopolymerization initiator; (D) a photopolymerizable monomer; And (E) a solvent for a color filter.
[Chemical Formula 1]
(In the formula 1,
R 1 to R 10 are the same or different and each represents a single bond, a substituted or unsubstituted C1 to C20 alkoxysilylene group, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, A substituted or unsubstituted C2 to C20 alkynylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C3 to C20 cycloalkenylene group, a substituted or unsubstituted C3 to C20 cycloalkynylene group, A substituted or unsubstituted C2 to C20 heterocycloalkylene group, a substituted or unsubstituted C2 to C20 heterocycloalkenylene group, a substituted or unsubstituted C2 to C20 heterocycloalkynylene group, a substituted or unsubstituted C6 to C30 aryl A substituted or unsubstituted C6 to C30 aryloxylene group, -S- or -SS-, at least one of R 1 to R 10 is -S- or -SS-,
R 11 to R 20 are the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an ether group, an amine group or an amine derivative group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted Or a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, Or an unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 aryloxy group.
The perylene-based dye may include at least one selected from the compounds represented by the following general formulas (2) and (3).
(2)
(3)
(In the above formulas 2 and 3,
And R 21 and R 25 are the same or different, a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 aryl group, -S- or -SS- ring, wherein R 21 and At least one of R < 25 > is -S- or -SS-,
R 22 and R 26 are each a substituted or unsubstituted C1 to C20 alkylene group,
R 23 , R 24 , R 27 , R 28 , R 29 , R 30 and R 32 are each a substituted or unsubstituted C 1 to C 20 alkyl group,
R 31 is -S- or -SS-,
and n 1 to n 3 are each an integer of 0 to 5.)
The colorant may further comprise a pigment.
The pigment may be selected from the group consisting of C.I. Red pigment 254, C.I. Red pigment 255, C.I. Red pigment 264, C.I. Red pigment 270, C.I. Red pigment 272, C.I. Red pigment 177, C.I. Red Pigment 89, C.I. Yellow pigment 139, C.I. Yellow pigment 138, C.I. Yellow pigment 150, or a combination thereof.
The colorant may include the perylene-based dye and the pigment in a weight ratio of 1:10 to 10: 1.
Wherein the photosensitive resin composition for a color filter comprises 0.01 to 60% by weight of the colorant (A); 0.5 to 20% by weight of the acrylic binder resin (B); 0.1 to 20% by weight of the photopolymerization initiator (C); 0.5 to 20% by weight of the (D) photopolymerizable monomer; And (E) the solvent balance.
Another embodiment of the present invention provides a color filter manufactured using the photosensitive resin composition for a color filter.
Other details of the embodiments of the present invention are included in the following detailed description.
The photosensitive resin composition for a color filter has high solubility and is excellent in chemical resistance, so that it can be usefully applied to a color filter.
Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.
Unless otherwise specified herein, "substituted" means that at least one hydrogen atom in the compound is replaced by a halogen atom (F, Cl, Br, I), a hydroxy group, a C1- A thio group, an ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, an imino group, an azido group, an amidino group, a hydrazino group, a hydrazino group, a carbonyl group, a carbamoyl group, A C 1 to C 20 alkyl group, a C 2 to C 20 alkenyl group, a C 2 to C 20 alkynyl group, a C 6 to C 30 aryl group, a C 3 to C 20 cycloalkyl group, a C 3 to C 20 cycloalkenyl group, Substituted with a substituent of a C2 to C20 heterocycloalkyl group, a C2 to C20 heterocycloalkenyl group, a C2 to C20 heterocycloalkynyl group, or a combination thereof.
Unless otherwise specified in the present specification, the term "amine derivative group" means an amine derivative group in NH 2 present in an amine in which at least one hydrogen atom is replaced by a halogen atom, a hydroxy group, a carboxyl group, an ether group, a sulfonate group, a sulfonic acid group, Or an unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C30 aryl group.
Unless otherwise specified in the specification, the "ether group" means ROR '(wherein R and R' are the same or different and are a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group , Or a substituted or unsubstituted C6 to C30 aryl group).
"Hetero" means that at least one heteroatom of N, O, S or P is present in the ring compound, unless otherwise specified herein.
As used herein, unless otherwise specified, "(meth) acrylate" means that both "acrylate" and "methacrylate" are possible.
The photosensitive resin composition for a color filter according to an embodiment includes (A) a colorant, (B) an acrylic binder resin, (C) a photopolymerization initiator, (D) a photopolymerizable monomer and (E) a solvent.
(A) Colorant
The colorant may be a perylene dye represented by the following formula (1).
[Chemical Formula 1]
The perylene-based dye represented by the above formula (1) has excellent solubility in solvents. From this, the compatibility with other components constituting the photosensitive resin composition for a color filter is excellent, and the production of the photosensitive resin composition for a color filter is facilitated.
Specifically, R 1 to R 10 in Formula 1 are the same or different and each represents a single bond, a substituted or unsubstituted C1 to C20 alkoxysylene group, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted A substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C3 to C20 cycloalkenylene group, a substituted or unsubstituted C3 A substituted or unsubstituted C2 to C20 heterocycloalkylene group, a substituted or unsubstituted C2 to C20 heterocycloalkenylene group, a substituted or unsubstituted C2 to C20 heterocycloalkynylene group, a substituted or unsubstituted C2 to C20 heterocycloalkylene group, An unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aryloxylene group, -S-, or -SS-. At least one of R 1 to R 10 may be -S- or -SS-.
Wherein R 1 to R 10 are all of a linking group that connects the end groups of the backbone and R 11 to R 20 of a perylene compound, at least one of the R 1 to R 10 may be connected to the group -S- or -SS- position . The connector may be a thermally decomposable connector. The high solubility to the solvent can be obtained primarily due to the presence of the terminal groups of R 11 to R 20. Secondly, when the thermal curing of the pattern formation process of the color filter is performed, the connecting group is thermally decomposed and separated with the terminal group The solubility in other solvents is lost and excellent chemical resistance can be obtained. Therefore, when the perylene compound according to one embodiment is used, the solubility of the perylene compound in the solvent is high, so that the photosensitive resin composition for a color filter can be easily produced. In the course of preparing a color filter, solubility in thermal curing is lowered. The chemical resistance can be improved.
Specifically, at least one of R 9 and R 10 may be -S- or -SS-, or at least one of R 1 to R 8 may be -S- or -SS-.
Wherein R 11 to R 20 are the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an ether group, an amine group or an amine derivative group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, Substituted or unsubstituted C2 to C20 heterocycloalkyl groups, substituted or unsubstituted C2 to C20 heterocycloalkenyl groups, substituted or unsubstituted C2 to C20 heterocycloalkyl groups, substituted or unsubstituted C3 to C20 cycloalkynyl groups, substituted or unsubstituted C2 to C20 heterocycloalkyl groups, An alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 aryloxy group.
Among these, preferably, R 11 to R 18 are hydrogen atoms, and R 19 and R 20 are the same or different from each other and each represents a halogen atom, a cyano group, a hydroxyl group, an ether group, an amine group or an amine derivative group, A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C6 to C30 aryloxy group. These substituents have a high interaction with a solvent, so that a high solubility in a solvent can be obtained.
The perylene-based dye may be at least one selected from compounds represented by the following general formulas (2) and (3).
(2)
(3)
In Formula 2, R 21 and R 25 are the same or different and each represents a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, -S- or -SS- And at least one of R 21 and R 25 may be -S- or -SS-.
In Formula 2, R 22 and R 26 may each be a substituted or unsubstituted C1 to C20 alkylene group.
In formulas 2 and 3, R 23 , R 24 , R 27 , R 28 , R 29 , R 30 and R 32 may be substituted or unsubstituted C 1 to C 20 alkyl groups.
In Formula 3, R 31 may be -S- or -SS-.
In Formula 3, n 1 to n 3 may each be an integer of 0 to 5.
The perylene-based dye may be a red dye.
As described above, the perylene-based dye is excellent in solubility in an organic solvent due to the presence of the terminal groups of R 11 to R 20 in the formula (1), and unlike the pigment having a particle property, It can be very durable with little or no primary particle diameter of several nanometers. By introducing such a perylene dye, it is possible to compensate the lowering of the contrast ratio and luminance, which are problems of the pigment dispersion method which is mainly used in the production of color filters.
The pyrolysis temperature of the perylene-based dye may be 250 ° C or higher, specifically 250 ° C to 500 ° C.
The perylene-based dye may have a solubility of 2 or more, specifically 2 to 10, in a solvent used in the photosensitive resin composition for a color filter, that is, a solvent (E) described below. The solubility can be obtained in terms of the amount (g) of the dye dissolved in 100 g of the solvent. When the solubility of the perylene-based dye is within the above-mentioned range, compatibility and coloring power with the components contained in the photosensitive resin composition for a color filter can be ensured and precipitation of the perylene-based dye can be prevented.
Specifically, the solvent may be selected from the group consisting of cyclohexanone, propylene glycol monomethyl ether acetate (PGMEA), ethyl lactate (EL), ethylene glycol ethyl acetate (EGA), cyclohexane Cyclohexanone, or a combination thereof.
The above-mentioned perylene-based dyes can be usefully used for color filters such as LCD and LED which exhibit high luminance and high contrast ratio in a desired color coordinate.
The perylene dye may be used together with at least one selected from azo dyes and xanthene dyes for dyeing.
The colorant may be a pigment in combination with the perylene-based dye.
The pigment may be at least one selected from organic pigments and inorganic pigments.
The above-mentioned pigment specifically includes C.I. Red pigment 254, C.I. Red pigment 255, C.I. Red pigment 264, C.I. Red pigment 270, C.I. Dipyrrolopyrrole pigments such as red pigment 272 and the like; C.I. Red pigment 177, C.I. Pigments such as red pigment 89 and the like; C.I. Isoindoline pigments such as yellow pigments 139 and the like; C.I. Quinophthalone-based pigments such as yellow pigments 138 and the like; C.I. A yellow complex pigment such as a yellow pigment 150 and the like can be used. These may be used alone or in combination of two or more.
The pigment can be used by reducing the primary particle diameter. This is specifically exemplified by a method in which a water-soluble inorganic salt and a wetting agent are mixed and finely kneaded in a kneader at a high pressure to reduce the primary particle diameter to less than 70 nm; a method in which the water-soluble inorganic salt and wetting agent are dissolved in an acid such as sulfuric acid, A method of reducing the primary particle diameter of the pigment using an acid pasting method or a method of reducing the primary particle diameter of the pigment by dry milling the pigment for a long time using a high-speed sand mill or the like may be used, but the present invention is not limited thereto . It is also possible to use commercially available pigments which have already reduced the primary particle diameter.
The primary particle diameter (D50) of the pigment may be 30 to 70 nm. When a pigment having the primary particle diameter in the above range is used, heat resistance, chemical resistance, durability, etc. are improved after forming a pixel.
The pigment may be included in the photosensitive resin composition for a color filter in the form of a dispersion. The pigment dispersion may be composed of the pigment, the solvent, the dispersing agent, the binder resin, and the like.
As the solvent, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether and the like can be used. Among them, propylene glycol methyl ether acetate is preferably used .
The dispersant helps to uniformly disperse the pigment in the dispersion, and any nonionic, anionic or cationic dispersant may be used. Specific examples thereof include polyalkylene glycols or esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, alkylamide alkylene oxide adducts Water, alkylamine, and the like. These may be used alone or in combination of two or more.
The binder resin may use an acrylic resin including a carboxyl group, which not only improves the stability of the pigment dispersion but also improves the patterning of pixels.
The primary particle diameter of the pigment may be 10 to 70 nm. When the primary particle diameter of the pigment is within the above range, the stability in the pigment dispersion is excellent and the resolution of the pixel is also excellent.
The secondary particle diameter of the pigment is not particularly limited, but may be 200 nm or less, in particular 70 to 100 nm, considering the resolution of the pixel.
The pigment may be contained in an amount of 0.1 to 30% by weight based on the total amount of the photosensitive resin composition for a color filter, and specifically 1 to 20% by weight. When the pigment is included in the above range, coloring property and developability are excellent.
When the above-mentioned perylene-based dye and the pigment are mixed, they may be mixed in a weight ratio of 1:10 to 10: 1. When mixed in the above-mentioned ratio range, they can have a high luminance and a high contrast ratio, and can exhibit desired color characteristics.
The colorant may be included in an amount of 0.01 to 60% by weight based on the total amount of the photosensitive resin composition for a color filter, specifically 0.1 to 40% by weight. When the dye is included in the above range, not only high brightness and high contrast ratio can be obtained, but also high solubility and excellent chemical resistance can be obtained.
(B) Acrylic binder resin
The acrylic binder resin may contain a first ethylenic unsaturated monomer And a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin comprising at least one acrylic repeating unit.
The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.
The first ethylenically unsaturated monomer may be included in an amount of 5 to 50% by weight based on the total amount of the acrylic binder resin, specifically 10 to 40% by weight.
The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly or in combination of two or more.
Specific examples of the acrylic binder resin include methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer Methacrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, but are not limited thereto, and they may be used alone or in combination of two or more.
The weight average molecular weight of the acrylic binder resin may be 3,000 to 150,000, specifically 5,000 to 50,000, and more specifically 20,000 to 30,000. When the weight average molecular weight of the acrylic binder resin is in the range described above, it has good adhesion with the substrate, good physical and chemical properties, and good viscosity.
The acid value of the acrylic binder resin may be 15 to 60 mgKOH / g, and specifically 20 to 50 mgKOH / g. When the acid value of the acrylic binder resin is within the above range, excellent pixel resolution can be obtained.
The acrylic binder resin may be contained in an amount of 0.5 to 20% by weight based on the total amount of the photosensitive resin composition for a color filter, and specifically 1 to 15% by weight. When the binder resin is contained in the pigment dispersion for stable dispersion of the pigment, the content of the acrylic binder resin is further reduced. When the acrylic binder resin is contained within the above range, the color filter is excellent in developability in the production of a color filter, and the cross-linkability is improved, whereby excellent surface smoothness can be obtained.
(C) Light curing Initiator
The photopolymerization initiator is a photopolymerization initiator generally used in a photosensitive resin composition for a color filter. Examples of the photopolymerization initiator include an acetophenone compound, a benzophenone compound, a thioxanone compound, a benzoin compound, a triazine compound, , Or a combination thereof.
Examples of the acetophenone compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, Dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane- 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one can be used.
Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.
Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Orcanthon and the like can be used.
Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
Examples of the triazine type compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) -s- triazine, 2- (3 ', 4'-dimethoxy (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho 1-yl) (Trichloromethyl) -s-triazine, 2- (4-methoxynaphtho 1-yl) -4,6-bis (trichloromethyl) 6-triazine, 2-4-trichloromethyl (4'-methoxystyryl) -6-triazine and the like can be used.
Examples of the oxime compounds include O-acyloxime compounds such as 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- Can be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- -Oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O-acetate and 1- (4-phenylsulfanylphenyl) Acetate and the like can be used.
In addition to the photopolymerization initiators of the above types, carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, and imidazole compounds can also be used as photopolymerization initiators.
The photopolymerization initiator may be included in an amount of 0.1 to 20% by weight based on the total amount of the photosensitive resin composition for a color filter, and specifically 1 to 10% by weight. When the photopolymerization initiator is contained within the above range, photopolymerization occurs sufficiently during exposure in a pattern formation process for producing a color filter, which results in excellent sensitivity, good pattern straightness, excellent solubility in solvents and storage stability, The unreacted initiator does not remain and the decrease in the transmittance can be prevented.
(D) Photopolymerization Monomer
As the photopolymerizable monomer, a polyfunctional monomer having two or more hydroxyl groups may be used. Specific examples of the photopolymerizable monomer include glycerol acrylate, dipentaerythritol hexaacrylate, ethylene glycol diacrylate, triethylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate Acrylate, pentaerythritol triacrylate, pentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythritol acrylate, pentaerythritol hexaacrylate, pentaerythritol triacrylate, pentaerythritol triacrylate, But are not limited to, ethylene glycol dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, propylene glycol dimethacrylate , 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate Acrylate and the like.
The photopolymerizable monomer may be contained in an amount of 0.5 to 20% by weight based on the total amount of the photosensitive resin composition for a color filter, and specifically 1 to 10% by weight. When the photopolymerizable monomer is contained within the above range, the pattern characteristic is excellent such as the edge of the pattern is formed cleanly when the color filter is manufactured, and the developability to the alkaline developer is excellent.
(E) Solvent
Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether and propylene glycol methyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid alkyl esters such as methyl lactate and ethyl lactate; Hydroxyacetic acid alkyl esters such as methylhydroxyacetate, ethylhydroxyacetate and butylhydroxyacetate; Alkoxyalkyl esters such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-hydroxypropionic acid alkyl esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate and propyl 2-hydroxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-hydroxy-2-methylpropionic acid alkyl esters such as methyl 2-hydroxy-2-methylpropionate and ethyl 2-hydroxy-2-methylpropionate; 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; Esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate and methyl 2-hydroxy-3-methyl butanoate; Or ethyl pyruvate. Examples of the ketone acid esters include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide Benzyl alcohol, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, Ethyl benzoate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc. These may be used alone or in combination of two or more.
In view of the miscibility and reactivity of the solvent, glycol ethers such as ethylene glycol monoethyl ether and the like; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2-hydroxyethyl propionate; Diethylene glycol such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.
The solvent may be included as the balance relative to the total amount of the photosensitive resin composition for a color filter, and specifically 20 to 90% by weight. When the solvent is contained within the above range, the photosensitive resin composition for a color filter is excellent in coating property, and excellent flatness can be maintained in a film having a thickness of 2 탆 or more.
(F) Other additives
The photosensitive resin composition for a color filter may contain at least one selected from the group consisting of malonic acid, malonic acid, and malonic acid, in order to prevent spots and spots during coating, 3-amino-1,2-propanediol; A silane-based coupling agent comprising a vinyl group or (meth) acryloxy group; Leveling agents; Fluorine surfactants; And other additives such as a radical polymerization initiator.
The fluorine-based surfactant may have a low weight average molecular weight of 4,000 to 10,000 g / mol, and more specifically, a weight average molecular weight of 6,000 to 10,000 g / mol. The fluorine-based surfactant may have a surface tension of 18 to 23 mN / m (measured in 0.1% polyethylene glycol methyl ether acrylate (PEGMEA) solution). When the weight average molecular weight and the surface tension of the fluorine-based surfactant are within the above range, the leveling performance can be improved, the stain property at the time of high speed coating is excellent, Thereby imparting excellent properties to the slit coating.
Specific examples of the fluorine-based surfactant include F-482, F-484 and F-478 of DIC Company, but are not limited thereto.
The fluorine-based surfactant may be used in combination with a silicone-based surfactant.
Specific examples of the silicone surfactant include TSF400, TSF401, TSF410, and TSF4440 of Toshiba Silicones, but are not limited thereto.
Further, the photosensitive resin composition for a color filter may further contain an epoxy compound as an additive for the purpose of improving adhesion and the like.
Examples of the epoxy compound include epoxy novolac acrylate carboxylate resin, orthocresol novolak epoxy resin, phenol novolak epoxy resin, tetramethyl biphenyl epoxy resin, bisphenol A type epoxy resin, alicyclic epoxy resin, or a combination thereof .
When the epoxy compound is further included, it may further include a radical polymerization initiator such as a peroxide initiator or an azobis-based initiator.
The epoxy compound may be used in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition for a color filter. When the epoxy compound is contained within the above range, the adhesion and other properties can be improved in terms of storage stability and economy.
The method for producing the photosensitive resin composition for a color filter is not particularly limited, but specifically, a photosensitive resin composition for a color filter is prepared by mixing the above-mentioned colorant, an acrylic binder resin, a photopolymerization initiator, a photopolymerizable monomer, a solvent, Can be manufactured.
According to another embodiment, there is provided a color filter made from the photosensitive resin composition for a color filter.
The color filter may be prepared by a conventional method. Specifically, the photosensitive resin composition for a color filter may be formed on a glass substrate by a suitable method such as spin coating, roller coating, slit coating, . After the application, UV light, electron beam or X-ray is irradiated to form a pattern necessary for the color filter. The UV light has a wavelength range of 190 to 450 nm, specifically 200 to 400 nm. Then, when the coating layer is treated with an alkali developing solution, the unexposed portions of the coating layer are dissolved and a pattern necessary for the image color filter is formed. By repeating this process according to the required number of R, G, and B colors, a color filter having a desired pattern can be obtained. Further, in the above process, the image pattern obtained by development may be further heated or cured by actinic ray irradiation or the like to further improve crack resistance, solvent resistance, and the like.
The contrast ratio of the photosensitive resin composition for a color filter measured using the obtained color filter pattern may be 9000 or more. The contrast ratio is a value calculated according to the following Equation 1 after measuring the amount of light when the polarizing plate is opened and closed by using Contrast tester CT-1 manufactured by Tsubosaka.
[Equation 1]
Contrast ratio = L open / L close
L open : the amount of light when the polarizing plate is opened
L close : the amount of light when the polarizing plate is closed
Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are only a preferred embodiment of the present invention, and the present invention is not limited by the following examples.
( Perylene Dye manufacture)
Manufacturing example One
3.0 g (0.0038 mol) of N, N'-bis (2,6-diisopropylphenyl) 1-bromopheylene 3,4,9,10-tetracarboxydioimide and 1.26 g 0.0076 mol) was added to 40 ml of N-methylpyrrolidone and K 2 CO 3 (0.0152 mol) was added, the temperature was raised to 120 DEG C under a nitrogen gas, and the mixture was refluxed for 6 hours. When the reaction was completed, the reaction mixture was cooled to room temperature and slowly poured into 400 ml of a 10% HCl aqueous solution to precipitate. The resulting precipitate was filtered under reduced pressure, washed several times with distilled water until the pH reached 7, and dried in a vacuum oven for one day to obtain a compound represented by the following formula (4).
[Chemical Formula 4]
Manufacturing example 2
A compound represented by the following formula (5) was obtained, except that 2.52 g (0.0152 mol) of 4-t-butylthiophenol was used in Production Example 1.
[Chemical Formula 5]
Comparative Manufacturing Example One
0.98 g (0.0025 mol) of perylene-3,4,9,10-tetracarboxylic dianhydride and 0.766 g (0.00575 mol, 2.3 equivalents) 60 ml of m-cresol and 10 ml of isoquinoline were slowly added to the reaction mixture under a nitrogen gas atmosphere. The reaction was then refluxed at 100 ° C for 4 hours, 120 ° C for 6 hours, 150 ° C for 5 hours, and 200 ° C for 2 hours and then cooled to room temperature. Then, 100 ml of methanol was added to the reaction mixture (dissolved in methanol), and then methanol and m-cresol were all evaporated using a rotary distillation apparatus, followed by drying in an oven for one day. The dried product was dissolved in methylene chloride (CH 2 Cl 2 ), washed repeatedly with water and 5% aqueous sodium hydroxide solution, and then passed through magnesium sulfate (MgSO 4 ) to remove methylene chloride using a rotary distillation apparatus Respectively. After drying in the oven for one day, methanol was added to precipitate and stirred for 2 hours. The resulting precipitate was filtered under reduced pressure, and then dried in an oven for one day to obtain a compound represented by the following formula (6).
[Chemical Formula 6]
Comparative Manufacturing Example 2
In Production Example 1, except that aminoacetal was not used in the above reaction product, the same procedure as in Production Example 1 was carried out to obtain a compound represented by the following formula (7).
(7)
(Preparation of Photosensitive Resin Composition for Color Filter)
The specifications of the components used in the production of the photosensitive resin composition for a color filter are as follows.
(A) Colorant
(A-1) Perylene dyes
(A-1-1) The compound prepared in Preparative Example 1 was used.
(A-1-2) The compound prepared in Preparative Example 2 was used.
(A-1-3) Comparative The compound prepared in Preparative Example 1 was used.
(A-1-4) Comparative The compound prepared in Preparative Example 2 was used.
(B) Acrylic binder resin
A methacrylic acid / benzyl methacrylate copolymer having a weight average molecular weight of 22,000 g / mol (mixing weight ratio 15/85) was used.
(C) Photopolymerization Monomer
Dipentaerythritol hexaacrylate was used.
(D) Light curing Initiator
(D-1) 1,2-octanedione was used.
(D-2) 2-Dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one was used.
(E) Solvent
(E-1) cyclohexanone was used.
(E-2) propylene glycol monomethyl ether acetate was used.
Example 1 and 2 and Comparative Example 1 and 2
Each component was mixed with the composition shown in Table 1 below to prepare a photosensitive resin composition for a color filter. Specifically, a photopolymerization initiator was dissolved in a solvent and stirred at room temperature for 2 hours. Then, a colorant was added thereto and stirred for 30 minutes. Then, an acrylic binder resin and a photopolymerizable monomer were added thereto and stirred at room temperature for 2 hours. The solution was filtered three times and impurities were removed to prepare a photosensitive resin composition for a color filter.
Rating 1: Perylene Dye solubility measurement
The perylene-based dye used in Examples 1 and 2 and Comparative Examples 1 and 2 was heated for 30 minutes by hot-air circulation drying at 200 ° C to measure the solubility of the perylene-based dye in the solvent before and after heating, The results are shown in Table 2 below.
At this time, the solubility is obtained in terms of the amount (g) of the perylene-based dye soluble in 100 g of the total of cyclohexanone and propylene glycol monomethyl ether acetate.
Evaluation 2: Chemical resistance measurement of photosensitive resin composition for color filter
Degreased and cleaned to a thickness of 2 to 3 mu m on a glass substrate having a thickness of 0.63 mm and dried on a hot plate at 90 DEG C for 2 minutes to obtain a coated film. Subsequently, the coated film was exposed using a high-pressure mercury lamp having a wavelength of 365 nm, and then dried in a hot-air circulating drying oven at 230 ° C for 60 minutes to obtain a specimen. The obtained specimens were measured for color characteristics (L *, a *, b *) using a spectrophotometer (MCPD3000, Otsuka electronic Co.) and immersed in N-methylpyrrolidone heated at 60 ° C for 10 minutes. And the color difference (? Eab *) between before and after was measured. The results are shown in Table 2 below.
It can be seen from the above Table 2 that Examples 1 and 2 using the perylene dye according to one embodiment have higher solubility before heating than those of Comparative Examples 1 and 2 and lower solubility in solvents after heating have. From these results, it can be seen that Examples 1 and 2 have high solubility in solvents and poor solubility at the time of thermal curing and excellent chemical resistance. In addition, in the case of Examples 1 and 2, since the difference in color characteristics between Comparative Examples 1 and 2 is small, it is understood that the chemical resistance is excellent.
It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.
Claims (7)
(B) an acrylic binder resin;
(C) Light curing
(D) a photopolymerizable monomer; And
(E) Solvent
Wherein the photosensitive resin composition is a photosensitive resin composition for a color filter.
[Chemical Formula 1]
(In the formula 1,
R 1 to R 10 are the same or different and each represents a single bond, a substituted or unsubstituted C1 to C20 alkoxysilylene group, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C2 to C20 alkenylene group, A substituted or unsubstituted C2 to C20 alkynylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C3 to C20 cycloalkenylene group, a substituted or unsubstituted C3 to C20 cycloalkynylene group, A substituted or unsubstituted C2 to C20 heterocycloalkylene group, a substituted or unsubstituted C2 to C20 heterocycloalkenylene group, a substituted or unsubstituted C2 to C20 heterocycloalkynylene group, a substituted or unsubstituted C6 to C30 aryl A substituted or unsubstituted C6 to C30 aryloxylene group, -S- or -SS-, at least one of R 1 to R 10 is -S- or -SS-,
R 11 to R 20 are the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an ether group, an amine group or an amine derivative group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted Or a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, Or an unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 aryloxy group.
Wherein the perylene-based dye comprises at least one selected from compounds represented by the following general formulas (2) and (3).
(2)
(3)
(In the above formulas 2 and 3,
And R 21 and R 25 are the same or different, a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 aryl group, -S- or -SS- ring, wherein R 21 and At least one of R < 25 > is -S- or -SS-,
R 22 and R 26 are each a substituted or unsubstituted C1 to C20 alkylene group,
R 23 , R 24 , R 27 , R 28 , R 29 , R 30 and R 32 are each a substituted or unsubstituted C 1 to C 20 alkyl group,
R 31 is -S- or -SS-,
and n 1 to n 3 are each an integer of 0 to 5.)
Wherein the coloring agent further comprises a pigment.
The pigment may be selected from the group consisting of CI Red Pigment 254, CI Red Pigment 255, CI Red Pigment 264, CI Red Pigment 270, CI Red Pigment 272, CI Red Pigment 177, CI Red Pigment 89, CI Yellow Pigment 139, CI Yellow Pigment 138, A pigment 150, or a combination thereof.
Wherein the colorant comprises the perylene-based dye and the pigment in a weight ratio of 1:10 to 10: 1.
The photosensitive resin composition for a color filter
0.01 to 60% by weight of the above (A) coloring agent;
0.5 to 20% by weight of the acrylic binder resin (B);
0.1 to 20% by weight of the photopolymerization initiator (C);
0.5 to 20% by weight of the (D) photopolymerizable monomer; And
The amount of the solvent (E)
Wherein the photosensitive resin composition is a photosensitive resin composition for a color filter.
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| KR1020120145120A KR20140076750A (en) | 2012-12-13 | 2012-12-13 | Photosensitive resin composition for color filter, and color filter using the same |
| CN201380060623.1A CN104813233A (en) | 2012-12-13 | 2013-04-29 | Photosensitive resin composition for color filter and color filter using same |
| PCT/KR2013/003682 WO2014092258A1 (en) | 2012-12-13 | 2013-04-29 | Photosensitive resin composition for color filter and color filter using same |
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| JP2018124553A (en) * | 2017-02-03 | 2018-08-09 | 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． | Self-luminous photosensitive resin composition, and color filter and image display device that comprise color conversion layer using that composition |
| WO2021065802A1 (en) * | 2019-10-04 | 2021-04-08 | 住友化学株式会社 | Benzoperylene compound and color curable resin composition |
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| KR101992084B1 (en) * | 2019-02-21 | 2019-06-21 | 동우 화인켐 주식회사 | A self emission type composition, a color conversion layer manufactured by using thereof and a color filter comprising the color conversion layer and display device |
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| US4934791A (en) * | 1987-12-09 | 1990-06-19 | Matsushita Electric Industrial Co., Ltd. | Color filter |
| KR20040044282A (en) * | 2002-11-21 | 2004-05-28 | 에스케이씨 주식회사 | Recording medium comprising colored layer and ink receiving layer |
| KR20050070619A (en) * | 2003-12-30 | 2005-07-07 | 제일모직주식회사 | Photosensitive resin composition for color filter |
| KR101277721B1 (en) * | 2010-04-07 | 2013-06-24 | 제일모직주식회사 | Photosensitive resin composition for color filter, and color filter using the same |
| KR101426542B1 (en) * | 2010-06-23 | 2014-08-06 | 서울대학교산학협력단 | Photosensitive resin composition, and color filter using the same |
| KR101453769B1 (en) * | 2010-12-24 | 2014-10-22 | 제일모직 주식회사 | Photosensitive resin composition and color filter using the same |
| KR101400196B1 (en) * | 2010-12-27 | 2014-06-19 | 제일모직 주식회사 | Photosensitive resin composition and color filter using the same |
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| JP2018124553A (en) * | 2017-02-03 | 2018-08-09 | 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． | Self-luminous photosensitive resin composition, and color filter and image display device that comprise color conversion layer using that composition |
| TWI679250B (en) * | 2017-02-03 | 2019-12-11 | 南韓商東友精細化工有限公司 | Self emission type photosensitive resin composition, color filter comprising color conversion layer using the same and display device |
| WO2021065802A1 (en) * | 2019-10-04 | 2021-04-08 | 住友化学株式会社 | Benzoperylene compound and color curable resin composition |
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