KR101887241B1 - Photosensitive resin composition, color filter using the same and display device - Google Patents
Photosensitive resin composition, color filter using the same and display device Download PDFInfo
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Abstract
(Problem) A photosensitive resin composition having good sensitivity and capable of suppressing occurrence of undercut in a pattern after development even in a situation where the photosensitive resin composition contains a light shielding agent or an insufficient exposure amount, and Providing the used color filter and display device.
A photopolymerizable composition comprising (A) a photopolymerizable compound, and (B) an oxime-based photopolymerization initiator represented by the following general formula (1), wherein n in the general formula (1) A photosensitive resin composition is used.
Description
The present invention relates to a photosensitive resin composition, and a color filter and a display device using the same.
A display device such as a liquid crystal display or the like has a structure in which a liquid crystal layer is sandwiched between two substrates on which opposing electrodes are formed. A color filter including pixel regions of respective colors of red (R), green (G), and blue (B) is formed on the inner side of one substrate. In this color filter, a black matrix is usually formed so as to divide each pixel region such as red, green, and blue.
Generally, color filters are produced by lithography. That is, first, a black photosensitive resin composition is coated on a substrate and dried, followed by exposure and development to form a black matrix. Subsequently, coating, drying, exposure, and development are repeated for each photosensitive resin composition of each color such as red, green, and blue to form a pixel region of each color at a specific position to produce a color filter.
The black matrix is a pattern produced from a photosensitive resin composition containing a light-shielding agent. By suppressing light leakage from each pixel region, the black matrix contributes to improvement of contrast in a display device and good color development. As described above, the black matrix formed at the initial stage of the fabrication of the color filter has recesses for embedding the photosensitive resin composition for coloring the pixel regions thereafter to form pixel regions of respective colors at specific positions It also plays a role.
In recent years, attempts have been made to improve the contrast of an image to be displayed on a liquid crystal display by improving the light-shielding property by the black matrix in the manufacture of a liquid crystal display. For this purpose, it is necessary to contain a large amount of a light-shielding agent in the photosensitive resin composition for forming a black matrix. However, when a large amount of the light-shielding agent is contained in the photosensitive resin composition, light for curing the photosensitive resin composition hardly reaches the bottom of the film when the film of the photosensitive resin composition coated on the substrate is exposed, Resulting in poor curing due to a remarkable decrease in sensitivity of the resin composition.
In the photosensitive resin composition, a photopolymerization initiator contained as a part of the component generates a radical by exposure, and the radical is cured by polymerizing a polymerizable compound contained in the photosensitive resin composition. Therefore, it is known that the sensitivity of the photosensitive resin composition is influenced by the kind of the photopolymerization initiator contained therein. In addition, in recent years, the production amount of the color filter has been increased in accordance with the increase in the number of production of liquid crystal display displays, and a photosensitive resin composition of high sensitivity capable of forming a pattern at a low exposure dose is desired from the viewpoint of better productivity improvement . In such a situation, oxime ester compounds having a cycloalkyl group have been proposed in Patent Documents 1 and 2 as a photopolymerization initiator capable of improving the sensitivity of the photosensitive resin composition. In the examples described in Patent Documents 1 and 2, compounds represented by the following chemical formulas (a) and (b) (Patent Document 1), and Chemical Formulas (c) and (d) .
[Chemical Formula 1]
By using the compounds represented by the above formulas (a) to (d) as a photopolymerization initiator, a photosensitive resin composition with high sensitivity can be produced. However, the inventors have found that, when these compounds are used as photopolymerization initiators to form a black matrix, the sensitivity is good, while the following problems arise in the pattern shape of the formed black matrix.
In general, when a pattern of a color filter for a liquid crystal display is formed by using a photosensitive resin composition, as shown in Fig. 1 (a), a cross section 1, which is a cross section in the width direction of the pattern, 1 a), and a narrower trapezoidal shape becomes closer to the right side (
However, when a black matrix is formed using a photosensitive resin composition containing the compound represented by the above-mentioned formulas (a) to (d) as a photopolymerization initiator, as shown in Fig. 1 (b) The
SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and it is an object of the present invention to provide a photosensitive resin composition which is excellent in sensitivity and suppresses occurrence of undercut in a pattern after development even in a situation such that a photosensitive resin composition contains a light shielding agent, And a color filter and a display device using the same.
As a result of intensive investigations to solve the above problems, the present inventors have found that, in an oxime ester compound having a specific structure and a cycloalkyl alkylene group bonded to an oxime carbon, an alkylene group between a carbon atom contained in the oxime group and a cycloalkyl group When the group is a methylene group (having 1 carbon atom) or a propylene group (having 3 carbon atoms), undercutting of the pattern is observed, while the alkylene group is particularly an ethylene group (having 2 carbon atoms) And the present invention has been accomplished.
A first aspect of the present invention is a photocurable composition comprising (A) a photopolymerizable compound and (B) a oxime-based photopolymerization initiator represented by the following general formula (1), wherein n in the general formula (1) Wherein the photosensitive resin composition is a photosensitive resin composition.
(2)
(Wherein, in the general formula (1), 1 is an integer of 1 to 5, m is an integer of 0 to (l + 3), R 1 is an alkyl group having 1 to 11 carbon atoms which may have a substituent, R 2 is any of the substituents represented by the following general formulas (2) to (4), and R 3 is an alkyl group having 1 to 11 carbon atoms or an aryl group,
(3)
(In the general formulas (2) and (3), R 4 is an aryl group which may have a substituent and R 5 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent or an aryl group. In the formula (4), R 6 is an aryl group which may have a substituent)
The second aspect of the present invention is a color filter formed using the photosensitive resin composition.
A third aspect of the present invention is a display device using the color filter.
According to the present invention, there is provided a photosensitive resin composition capable of suppressing occurrence of undercut in a developed pattern even in a situation where the photosensitive resin composition has good sensitivity and contains a light shielding agent or an insufficient exposure amount, And a color filter and a display device using the same are provided.
Fig. 1 is a schematic view showing a cross-sectional shape of a pattern formed from a photosensitive resin composition in a width direction, wherein Fig. 1 (a) is a cross-sectional view of a typical pattern, Fig.
[Photosensitive resin composition]
The photosensitive resin composition according to the present invention contains at least a photopolymerizable compound (A) and an oxime-based photopolymerization initiator (B). Hereinafter, each component contained in the photosensitive composition of the present invention will be described in detail.
≪ (A) Photopolymerizable compound >
The (A) photopolymerizable compound contained in the photosensitive resin composition according to the present invention is not particularly limited and conventionally known photopolymerizable compounds can be used. Among them, resins or monomers having an ethylenic unsaturated group are preferable, and a combination thereof is more preferable. The combination of a resin having an ethylenic unsaturated group and a monomer having an ethylenic unsaturated group improves the curability of the photosensitive resin composition and facilitates pattern formation.
[Resin Having Ethylenic Unsaturated Group]
Examples of the resin having an ethylenic unsaturated group include (meth) acrylic acid, fumaric acid, maleic acid, monomethyl fumarate, monoethyl fumarate, 2-hydroxyethyl (meth) acrylate, ethylene glycol monomethyl ether Acrylates such as glycol monoethyl ether (meth) acrylate, glycerol (meth) acrylate, (meth) acrylamide, acrylonitrile, methacrylonitrile, methyl (meth) acrylate, (Meth) acrylate, diethyleneglycol di (meth) acrylate, triethyleneglycol di (meth) acrylate, diethyleneglycol di (meth) Acrylate, trimethylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, trimethylolpropane tri (Meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, and cardo epoxy diacrylate; a polyester prepolymer obtained by condensing a polyhydric alcohol with a monobasic acid or a polybasic acid (Meth) acrylate obtained by reacting a polyol with a compound having two isocyanate groups and then reacting with (meth) acrylic acid; a polyurethane (meth) acrylate obtained by reacting a bisphenol A type epoxy resin, Bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol or cresol novolak type epoxy resin, Epoxy resins such as epoxy resins, triphenolmethane type epoxy resins, polycarboxylic acid polyglycidyl esters, polyol polyglycidyl esters, aliphatic or alicyclic epoxy resins, amine epoxy resins and dihydroxybenzene type epoxy resins, , And epoxy (meth) acrylate resins obtained by reacting (meth) acrylic acid. Further, a resin obtained by reacting an epoxy (meth) acrylate resin with a polybasic acid anhydride can be preferably used. In the present specification, "(meth) acryl" means "acryl or methacryl".
As the resin having an ethylenic unsaturated group, a resin obtained by reacting a reaction product of an epoxy compound and an unsaturated group-containing carboxylic acid compound with a polybasic acid anhydride can be preferably used.
Among them, a compound represented by the following formula (a1) is preferable. The compound represented by the formula (a1) is preferable in view of its high photocurability.
[Chemical Formula 4]
In the formula (a1), X represents a group represented by the following formula (a2).
[Chemical Formula 5]
R 2a in the formula (a2) each independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a halogen atom, R 2a independently represents a hydrogen atom or a methyl group, W represents a single bond, (a3).
[Chemical Formula 6]
In the above formula (a1), Y represents a residue obtained by removing an acid anhydride group (-CO-O-CO-) from a dicarboxylic acid anhydride. Examples of the dicarboxylic acid anhydride include maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, anhydrous tetrahydrophthalic acid, anhydrous hexahydrophthalic acid, methylendomethylenetetrahydrophthalic anhydride, anhydrous chlorodic acid, Phthalic acid, and anhydrous glutaric acid.
In the above formula (a1), Z represents a residue other than the two acid anhydride groups from the tetracarboxylic acid dianhydride. Examples of the tetracarboxylic acid dianhydride include anhydrous pyromellitic acid, benzophenonetetracarboxylic acid dianhydride, biphenyltetracarboxylic acid dianhydride, and biphenyl ether tetracarboxylic dianhydride.
In the above formula (a1), m represents an integer of 0 to 20.
The acid value of the resin having an ethylenically unsaturated group is preferably from 10 to 150 mgKOH / g, more preferably from 70 to 110 mgKOH / g, in terms of resin solid content. When the acid value is 10 mgKOH / g or more, sufficient solubility in a developing solution can be obtained, which is preferable. The acid value of 150 mgKOH / g or less is preferable because sufficient curability can be obtained and the surface property can be improved.
The mass average molecular weight of the resin having an ethylenic unsaturated group is preferably from 1,000 to 40,000, more preferably from 2,000 to 30,000. By setting the mass average molecular weight to 1,000 or more, it is preferable to obtain good heat resistance and film strength. The weight average molecular weight is preferably 40,000 or less, because good developability can be obtained.
[Monomer having an ethylenically unsaturated group]
Monomers having an ethylenic unsaturated group include monofunctional monomers and polyfunctional monomers.
Examples of the monofunctional monomer include (meth) acrylamide, methylol (meth) acrylamide, methoxymethyl (meth) acrylamide, ethoxymethyl (meth) acrylamide, propoxymethyl (Meth) acrylamide, N-hydroxymethyl (meth) acrylamide, (meth) acrylic acid, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, (Meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, isopropyl (meth) acrylate, (Meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-hydroxyethyl 2-phenoxy-2-hydroxypropyl (meth) (Meth) acrylate, glycidyl (meth) acrylate, glycerin mono (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, dimethylamino (Meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate and half . These monofunctional monomers may be used alone or in combination of two or more.
Examples of the polyfunctional monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polypropylene glycol di (Meth) acrylate, trimethylolpropane tri (meth) acrylate, glycerin (meth) acrylate, trimethylolpropane tri (meth) (Meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol di Tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol (Meth) acryloxypolyethoxyphenyl) propane, 2,2-bis (4- (meth) acryloxy diethoxyphenyl) propane, (Meth) acryloyloxypropyl (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, phthalic acid diglycidyl (Meth) acrylate, glycerin triacrylate, glycerin polyglycidyl ether poly (meth) acrylate, urethane (meth) acrylate (i.e., tolylene diisocyanate), trimethylhexamethylene diisocyanate and hexamethylene di (Meth) acrylamide, (meth) acrylamide methylene ether, a condensation product of a polyhydric alcohol and N-methylol (meth) acrylamide, and the like, as well as a reaction product of isocyanate and 2-hydroxyethylMeona furnace, and the like can be triacrylate formal. These multifunctional monomers may be used alone or in combination of two or more.
The content of the photopolymerizable compound as the component (A) is preferably 10 to 99.9 parts by mass based on 100 parts by mass of the total solid content of the photosensitive resin composition. When the content of the component (A) is 10 parts by mass or more based on 100 parts by mass of the total of the solid content, sufficient heat resistance and chemical resistance of the formed pattern can be expected.
<(B) Oxime-based photopolymerization initiator>
The oxime-based photopolymerization initiator contained in the photosensitive resin composition according to the present invention is a compound represented by the following general formula (1), in which n in the general formula (1) is 2. As already described, the oxime-based photopolymerization initiator gives good sensitivity even when the composition contains a light-shielding agent, particularly in the case of a photosensitive resin composition for forming a black matrix. On the other hand, In some cases. As the oxime-based photopolymerization initiator which is a component (B), the present inventors have found that, as represented by the following general formula (1), an alkylene group in which a carbon atom contained in an oxime group is bonded to a cycloalkylalkyl group, By using an oxime-based compound in which the group is an ethylene group (that is, n = 2 in the following general formula (1)) as a photopolymerization initiator, underscaling in a pattern to be formed, while imparting good sensitivity to the photosensitive resin composition And the present invention has been completed. Therefore, in the photosensitive resin composition according to the present invention, an oxime-based photopolymerization initiator in which n = 2 in the following general formula (1) is used as the component (B).
(7)
In the general formula (1), n is 2, 1 is an integer of 1 to 5, m is an integer of 0 to (l + 3), R 1 is an alkyl group having 1 to 11 carbon atoms which may have a substituent, , R 2 is any of substituents represented by the following general formulas (2) to (4), and R 3 is an alkyl group having 1 to 11 carbon atoms or an aryl group. As the substituent which R 1 may be taken as an alkyl group, a phenyl group, a naphthyl group and the like are preferably exemplified. The substituent which may be taken when R 1 is an aryl group is preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a halogen atom or the like.
In the general formula (1), R 1 is preferably a methyl, ethyl, propyl, isopropyl, butyl, phenyl, benzyl, methylphenyl or naphthyl group. Is more preferable. In the general formula (1), R 3 is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a phenyl group, and among these, a methyl group is more preferable.
[Chemical Formula 8]
In the general formulas (2) and (3), R 4 is an aryl group which may have a substituent, and R 5 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aryl group. As the substituent which the R 4 aryl group may have, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a halogen atom and the like are preferably exemplified. As the substituent which may be introduced when R 5 is an alkyl group, an alkoxy group having 1 to 5 carbon atoms, a phenyl group, a naphthyl group and the like are preferably exemplified.
Examples of R 4 in the general formulas (2) and (3) include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2-ethylphenyl group, A 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a naphthyl group, a 2-methoxy-1-naphthyl group and a 9-anthracenyl group are preferable. Examples of R 5 in the general formulas (2) and (3) include a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n- butyl group, an isobutyl group, , n-pentyl group, n-hexyl group, phenyl group, 3-methylbutyl group, 3-methoxybutyl group and the like are preferably exemplified.
In the general formula (4), R 6 is an aryl group which may have a substituent. As the substituent which the R 6 aryl group may have, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a halogen atom and the like are preferably exemplified.
Examples of R 6 include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2-ethylphenyl group, a 3-ethylphenyl group, A dimethylphenyl group, a 2,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a naphthyl group, a p-tert-butylphenyl group, a p-methoxyphenyl group and the like are preferable. Among them, a phenyl group is more preferable.
More specifically, as the oxime-based photopolymerization initiator (B), a compound of the following formula can be preferably exemplified.
[Chemical Formula 9]
The content of the oxime-based photopolymerization initiator as the component (B) is preferably from 0.1 to 50 parts by mass, more preferably from 1 to 45 parts by mass, per 100 parts by mass of the total of the solid components of the photosensitive resin composition. Within the above range, sufficient heat resistance and chemical resistance can be obtained, coating film forming ability can be improved, and optical hardening defects can be suppressed.
≪ (C) Colorant >
The photosensitive resin composition according to the present invention may further contain (C) a colorant. The photosensitive resin composition is preferably used for forming a color filter of a liquid crystal display, for example, by containing a colorant as the component (C). The photosensitive resin composition according to the present invention is preferably used for forming a black matrix in a color filter of a display device, for example, by containing a light-shielding agent as a coloring agent.
The colorant (C) contained in the photosensitive resin composition according to the present invention is not particularly limited, but it is classified as a pigment in a color index (CI, published by The Society of Dyers and Colourists) Specifically, it is preferable to use a compound having a color index (CI) number as described below.
C.I. Pigment Yellow 1 (hereinafter, "CI Pigment Yellow" is the same and only the numbers are described below), 3,11,12,13,14,15,16,17,20,24,31,35,55,60 , 61, 65, 71, 73, 74, 81, 83, 86, 93, 95, 97, 98, 99, 100, 101, 104, 106, 108, 109, , 120, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168, 175, 180, 185;
C.I. Pigment Orange 1 (hereinafter, "CI Pigment Orange" is the same and only the numbers are described below), 5,13,14,16,17,24,34,36,38,40,43,46,49,51 , 55, 59, 61, 63, 64, 71, 73;
C.I. Pigment Violet 1 (hereinafter, "C.I. Pigment Violet" is the same and only the numbers are described below), 19, 23, 29, 30, 32, 36, 37, 38, 39, 40, 50;
C.I. Pigment Red 1 (hereinafter, "CI Pigment Red" is the same and only the numbers are described below), 2,3,4,5,6,7,8,9,10,11,12,14,15,16 48: 3, 48: 4, 49: 1, 49: 1, 48, : 2, 50: 1, 52: 1, 53: 1, 57, 57: 1, 57: 2, 58: 2, 58: 4, 60: 1, 63: : 1, 83, 88, 90: 1, 97, 101, 102, 104, 105, 106, 108, 112, 113, 114, 122, 123, 144, 146, 149, 150, 151, 155, 166, 168 171, 172, 174, 175, 176, 177, 178, 179, 180, 185, 187, 188, 190, 192, 193, 194, 202, 206, 207, 208, 209, 215, 216, 217 , 220, 223, 224, 226, 227, 228, 240, 242, 243, 245, 254, 255, 264, 265;
C.I. Pigment Blue 1 (hereinafter, "C.I. Pigment Blue" is the same and only the numbers are described), 2, 15, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, 66;
C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment Green 37;
C.I. Pigment Brown 23, C.I. Pigment Brown 25, C.I. Pigment Brown 26, C.I. Pigment Brown 28;
C.I. Pigment Black 1, C.I. Pigment Black 7.
When a colorant is used as the light shielding agent, it is preferable to use a black pigment as the light shielding agent. Examples of the black pigment include organic pigments such as carbon black, titanium black, metal oxides such as copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium and silver, complex oxides, metal sulfides, metal sulfates or metal carbonates, Various pigments can be mentioned. Among these, it is preferable to use carbon black having high light shielding properties. By using the component (B) as the photopolymerization initiator, occurrence of undercut in the pattern after development can be suppressed even when a black pigment having high light shielding property is used.
Known carbon black such as channel black, furnace black, thermal black and lamp black can be used as carbon black, but it is preferable to use channel black having excellent light shielding properties. Resin-coated carbon black may also be used.
Resin-coated carbon black has low electric conductivity compared to carbon black without resin coating, so that when used as a black matrix of a liquid crystal display element such as a liquid crystal display, leakage of electric current is small, and a highly reliable and low- Can be manufactured.
In order to adjust the color tone of the carbon black, the organic pigment may be appropriately added as an auxiliary pigment.
In order to uniformly disperse the colorant in the photosensitive resin composition, a dispersant may be further used. As such a dispersing agent, it is preferable to use a polymeric dispersant of polyethylene imine type, urethane resin type or acrylic resin type. Particularly, when carbon black is used as a coloring agent, it is preferable to use an acrylic resin-based dispersing agent as a dispersing agent.
The inorganic pigments and the organic pigments may be used alone or in combination of two or more. When used in combination, it is preferable to use the organic pigments in an amount of from 10 to 80 parts by mass per 100 parts by mass of the total amount of the inorganic pigments and the organic pigments , And more preferably in the range of 20 to 40 parts by mass.
The amount of the coloring agent to be used in the photosensitive resin composition may be appropriately determined depending on the use of the photosensitive resin composition. For example, the amount is preferably 5 to 70 parts by mass, more preferably 25 to 60 parts by mass per 100 parts by mass of the total solid content of the photosensitive resin composition The addition is more preferable. Within the above range, a black matrix or each coloring layer can be formed with a desired pattern, which is preferable.
In particular, when a black matrix is formed using a photosensitive resin composition, it is preferable to adjust the amount of the light-shielding agent in the photosensitive resin composition so that the OD value per 1 탆 of the coating of the black matrix is 4 or more. When the OD value per 1 mu m of the coating film in the black matrix is 4 or more, sufficient display contrast can be obtained when the black matrix is used for a black matrix of a liquid crystal display.
The colorant is preferably added to the photosensitive resin composition after preparing a dispersion in which the dispersant is dispersed at an appropriate concentration.
≪ Other components >
Various additives may be added to the photosensitive resin composition according to the present invention, if necessary. Specifically, examples thereof include a solvent, a sensitizer, a curing accelerator, a photocrosslinking agent, a photosensitizer, a dispersion auxiliary, a filler, an adhesion promoter, an antioxidant, an ultraviolet absorber, an antiflocculating agent, a heat polymerization inhibitor, a defoaming agent and a surfactant.
Examples of the solvent used in the photosensitive resin composition according to the present invention include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol mono Methyl ethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, Propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene Glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol (Poly) alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and monoethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, (Poly) alkylene glycol monoalkyl ether acetates such as ether acetate and propylene glycol monoethyl ether acetate, and other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether and tetrahydrofuran Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone and 3-heptanone; alkyl lactates such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; Methyl propionate, methyl 3-methoxypropionate, 3-methoxypropionic acid Methyl 3-methoxybutylacetate, 3-methyl-3-methoxybutylacetate, 3-methoxybutylacetate, 3-methoxybutylacetate, Propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, ethyl butyrate, Other esters such as ethyl acetate, n-butyl acetate, isopropyl n-butyl acetate, isopropyl n-butyl acetate, isopropyl butylate, n-butyl butylate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, Aromatic amines such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide. These solvents may be used alone, or two or more solvents may be used in combination.
Among these solvents, propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 3- Methoxybutyl acetate is preferred because it exhibits excellent solubility in the above-mentioned components (A) and (B) and also in that the dispersibility of the above-mentioned component (C) can be improved, and propylene glycol mono It is particularly preferred to use methyl ether acetate, 3-methoxybutyl acetate. The solvent may be appropriately determined depending on the use of the photosensitive resin composition. For example, the solvent may be about 50 to 900 parts by mass based on the total 100 parts by mass of the solid content of the photosensitive resin composition.
Examples of the heat polymerization inhibitor used in the photosensitive resin composition according to the present invention include hydroquinone, hydroquinone monoethyl ether, and the like. Examples of the defoaming agent include silicon compounds and fluorine compounds. Examples of the surfactant include anion compounds, cation compounds, and nonionic compounds.
[Method for preparing photosensitive resin composition]
The photosensitive resin composition according to the present invention is prepared by mixing all of the above components with a stirrer. Further, it may be filtered using a filter so that the prepared photosensitive resin composition is uniform.
[Pattern formation method]
In order to form a pattern using the photosensitive resin composition of the present invention, a non-contact type coating device such as a roll coater, a reverse coater, a bar coater or the like, a contact transfer type coating device, a spinner , A photosensitive resin composition is coated on the substrate.
Subsequently, the applied photosensitive resin composition is dried to form a coating film. The drying method is not particularly limited and includes, for example, (1) a method of drying on a hot plate at a temperature of 80 to 120 ° C, preferably 90 to 100 ° C for 60 to 120 seconds, (2) (3) a method of removing the solvent by putting it in a warm air heater or an infrared heater for several minutes to several hours, and the like.
Subsequently, the coating film is partially exposed by irradiating active energy rays such as ultraviolet rays and excimer laser beams through a negative mask. The energy dose to be irradiated varies depending on the composition of the photosensitive resin composition, but is preferably about 30 to 2000 mJ / cm 2, for example.
Subsequently, the exposed film is developed with a developing solution to be patterned into a desired shape. The developing method is not particularly limited, and for example, a dipping method, a spraying method, or the like can be used. Examples of the developing solution include organic ones such as monoethanolamine, diethanolamine and triethanolamine, and aqueous solutions such as sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia and quaternary ammonium salts. As described above, by using the photosensitive resin composition according to the present invention, the undercut in the pattern formed after development is suppressed. Therefore, the use of the photosensitive resin composition of the present invention is preferable because, for example, when a color filter for a display device is manufactured, bubbles can be prevented from entering the vicinity of the boundary of each pixel.
Subsequently, post-baking is preferably performed at about 200 ° C to 250 ° C with respect to the pattern after development.
The pattern thus formed can be preferably used as a pixel of a color filter or a black matrix in a display device such as a liquid crystal display or the like. Such a color filter or a display device using the color filter is also one of the present invention.
Hereinafter, the present invention will be described in more detail with reference to examples, but the scope of the present invention is not limited to these examples.
[Preparation of Photosensitive Resin Composition]
[Examples 1 to 6 and Comparative Examples 1 to 7]
Photosensitive resin compositions of Examples 1 to 6 and Comparative Examples 1 to 7 were prepared using oxime-based photopolymerization initiators of the following formulas E1 to E6 and C1 to C7. In the photosensitive resin compositions of Examples 1 to 6, oxime-based photopolymerization initiators of the following formulas E1 to E6 were used, and in the photosensitive resin compositions of Comparative Examples 1 to 7, oxime-based photopolymerization initiators of the following formulas C1 to C7 Were used.
100 parts by mass of the oxime-based photopolymerization initiator, 310 parts by mass of the following resin A (solid content: 55% by mass, solvent 3-methoxybutyl acetate) ) And 175 parts by mass of a carbon black dispersion (carbon black content 20% by mass, "CF black", manufactured by Mikuni Color Co., Ltd.) were added to a mixture of 175 parts by mass of 3-methoxybutyl acetate / cyclo Hexanone / propylene glycol monomethyl ether acetate (PGMEA) = 60/20/20 (weight ratio), and stirring was continued until uniform.
The resin A used in the preparation of the photosensitive resin composition is the same as the resin A-1 described in paragraphs 0063 to 0064 of Japanese Laid-Open Patent Publication No. 2010-32940. The extinction coefficients of the h, i, j and k lines in the respective oxime-based photopolymerization initiators of the following formulas E1 to E6 and C1 to C7 were equal. The oxime-based photopolymerization initiators of the following formulas E1 to E6 used in the preparation of the photosensitive resin compositions of Examples 1 to 6 are all compounds in which n = 2 in the general formula (1). The oxime-based photopolymerization initiators represented by the following formulas C1 to C7 used in the preparation of the photosensitive resin compositions of Comparative Examples 1 to 7 are all compounds in which n ≠ 2 in the general formula (1) 1). The numerical value shown as "n" in Table 1 means the numerical value of n in the general formula (1), and "CB" described as "pigment kind" in Table 1 means carbon black. "N" in Table 1 means that the photosensitive resin composition described as "-" contains a compound not corresponding to the general formula (1) as the oxime-based photopolymerization initiator.
[Example 7, Comparative Example 8]
A photosensitive resin composition of Example 7 was prepared in the same manner as in Example 1 except that 450 parts by mass of an AgSn dispersion (AgSn content 20 mass%, PGMEA solution) was used instead of the carbon dispersion. The photosensitive resin composition of Comparative Example 8 was prepared in the same manner as in Comparative Example 1, except that 450 parts by mass of an AgSn dispersion (AgSn content 20 mass%, PGMEA solution) was used instead of the carbon dispersion.
[Chemical formula 10]
(11)
[Chemical Formula 12]
[Sensitivity evaluation]
The sensitivity of each of the photosensitive resin compositions of Examples 1 to 7 and Comparative Examples 1 to 8 was evaluated by the following procedure. The sensitivity evaluation was carried out in the following order. First, the photosensitive resin composition was spin-coated on a glass substrate (10 cm x 10 cm) and heated at 90 占 폚 for 120 seconds to form a 1.0 占 퐉 coating film on the surface of the glass substrate. Thereafter, using a mirror projection aligner (product name: TME-150RTO, manufactured by TOPCON CORPORATION), a negative type mask having a pattern of 10 mu m was formed and exposed at an exposure amount of 30-60-1200 mJ / cm2 (Gap 50 mu m) Lt; / RTI > The exposed film was developed with a 0.04 mass% KOH aqueous solution at 26 캜 for 30 seconds and then subjected to a firing treatment at 230 캜 for 30 minutes. The line width of the pattern at each exposure amount was measured with an optical microscope, The exposure amount at which a line width of 10 mu m was obtained was calculated by approximate calculation by the method. The calculated data of the sensitivity (mJ / cm 2) at a development time of 30 seconds are shown in Table 1. The sensitivity data shown in Table 1 indicate the exposure amount necessary to form a pattern (10 mu m) of a predetermined line width, and the smaller the value, the higher the sensitivity of the photosensitive resin composition.
[Pattern shape evaluation]
Each of the photosensitive resin compositions of Examples 1 to 6 and Comparative Examples 1 to 7 was subjected to exposure in the following procedure, and then the presence or absence of undercut in the pattern after development, that is, the pattern shape was evaluated. First, the photosensitive resin composition was spin-coated on a glass substrate (10 cm x 10 cm) and heated at 90 占 폚 for 120 seconds to form a 1.0 占 퐉 coating film on the surface of the glass substrate. Thereafter, using a mirror projection aligner (product name: TME-150RTO, manufactured by Topcon Co., Ltd.), exposure was performed with an exposure amount of 100 mJ / cm 2 (Gap 50 탆) through a negative mask in which a pattern of 10 탆 was formed. The exposed film was developed with a 0.04 mass% KOH aqueous solution at 26 占 폚 for 50 seconds and then subjected to a firing treatment at 230 占 폚 for 30 minutes and the bonding angle (taper angle) between the pattern and the substrate was measured with a scanning electron microscope. This taper angle corresponds to the angle (?) In Figs. 1 (a) and 1 (b). Table 1 shows the measured taper angles. If the taper angle is an acute angle, it means that no undercut exists in the pattern, and if the taper angle is an obtuse angle, it means that an undercut exists in the pattern.
As can be understood from Table 1, the photosensitive resin compositions of Examples 1 to 7, in which the compound having n = 2 in the general formula (1) was used as the oxime-based photopolymerization initiator, It can be understood that the sensitivity tends to be higher than that of the photosensitive resin compositions of Comparative Examples 1 to 8 using a compound represented by the formula (1) wherein n ≠ 2 or a compound not corresponding to the formula (1). It can be understood that this tendency is the same whether carbon black is used as a light shielding agent or AgSn is used.
In each of the photosensitive resin compositions of Examples 1 to 6, in which the compound represented by the general formula (1) wherein n = 2 was used as the oxime-based photopolymerization initiator, the taper angle was an acute angle of less than 90 °, The undercut did not occur. On the contrary, in the photosensitive resin compositions of Comparative Examples 1 to 7, in which n ≠ 2 in the general formula (1) or compounds not corresponding to the general formula (1) were used as the oxime-based photopolymerization initiator, , The taper angle became an obtuse angle exceeding 90 DEG, and undercut occurred in the pattern. From this point of view, it can be understood that the photosensitive resin composition of the present invention is effective for forming a pattern of a good shape which does not cause undercut.
1: cross-section in the width direction in a pattern in which no undercut exists
2: cross-section in the width direction in the pattern in which the undercut is present
Claims (8)
(Wherein, in the general formula (1), 1 is an integer of 1 to 5, m is an integer of 0 to (l + 3), R 1 is an alkyl group having 1 to 11 carbon atoms which may have a substituent, an aryl group, R 2 is to will any of the substituents represented by formula (2) ~ (4), R 3 is an alkyl group, or an aryl group having a carbon number of 1 to 11. to the end, the R 2 formula (2 ), R < 1 > is an aryl group which may have a substituent)
(In the general formulas (2) and (3), R 4 is an aryl group which may have a substituent and R 5 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent or an aryl group. In the formula (4), R 6 is an aryl group which may have a substituent)
And R 2 is a substituent represented by the general formula (3) or (4).
Y represents a residue other than an acid anhydride group (-CO-O-CO-) from a dicarboxylic acid anhydride, Z represents a tetracarboxylic acid anhydride group, And m represents an integer of 0 to 20).
(Wherein R 1a independently represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, or a halogen atom, R 2a independently represents a hydrogen atom or a methyl group, W represents a single bond or a Represents a group represented by the formula (a3)
(Wherein, in the general formula (1), 1 is an integer of 1 to 5, m is an integer of 0 to (l + 3), R 1 is an alkyl group having 1 to 11 carbon atoms which may have a substituent, R 2 is any of the substituents represented by the following general formulas (2) to (4), and R 3 is an alkyl group having 1 to 11 carbon atoms or an aryl group,
(In the general formulas (2) and (3), R 4 is an aryl group which may have a substituent, and R 5 is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, In the formula (4), R 6 is an aryl group which may have a substituent)
Wherein R 1 is an aryl group which may have a substituent when R 2 is a substituent represented by the above general formula (2).
Further comprising a colorant (C).
Wherein the coloring agent is a light-shielding agent.
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| CN101508744B (en) * | 2009-03-11 | 2011-04-06 | 常州强力电子新材料有限公司 | Carbazole oxime ester lightlike initiating agent |
| JP5793924B2 (en) * | 2011-04-11 | 2015-10-14 | 日立化成株式会社 | Photosensitive resin composition, photosensitive element, method for producing resist pattern, and method for producing printed wiring board |
| JP6064411B2 (en) * | 2011-09-28 | 2017-01-25 | Jsr株式会社 | Coloring composition, color filter and display element |
| CN104583867B (en) * | 2012-08-08 | 2020-03-17 | 旭化成株式会社 | Photosensitive film laminate, flexible printed wiring board, and method for producing same |
| KR101968510B1 (en) * | 2013-02-06 | 2019-04-12 | 동우 화인켐 주식회사 | Photosensitive resin composition for forming red pixel pattern |
| CN103130919B (en) * | 2013-02-08 | 2015-02-25 | 常州强力先端电子材料有限公司 | Carbazole ketone oxime ester high-photosensibility photoinitiator |
| JP6178164B2 (en) * | 2013-08-23 | 2017-08-09 | 富士フイルム株式会社 | Photosensitive coloring composition, color filter, method for producing color filter, organic EL liquid crystal display device |
| JP6375236B2 (en) * | 2014-02-04 | 2018-08-15 | 新日鉄住金化学株式会社 | Photosensitive composition for light shielding film and cured product thereof |
| JP6401529B2 (en) * | 2014-07-15 | 2018-10-10 | 東京応化工業株式会社 | Photosensitive composition |
| JP6254280B2 (en) * | 2014-07-15 | 2017-12-27 | 東京応化工業株式会社 | Compound |
| KR101991699B1 (en) | 2016-09-26 | 2019-06-21 | 삼성에스디아이 주식회사 | Photosensitive resin composition, black pixel defining layer using the same and display device |
| JP6785122B2 (en) | 2016-10-24 | 2020-11-18 | 東京応化工業株式会社 | Method for forming a photosensitive composition and a cured film |
| JP7560954B2 (en) | 2020-04-10 | 2024-10-03 | 東京応化工業株式会社 | Photosensitive composition, method for producing patterned cured film, and patterned cured film |
| JP2021167905A (en) | 2020-04-10 | 2021-10-21 | 東京応化工業株式会社 | Photosensitive composition, patterned cured film production method, and patterned cured film |
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| JP5096814B2 (en) * | 2007-07-04 | 2012-12-12 | 東京応化工業株式会社 | Colored photosensitive composition |
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