TWI846466B - Method for producing pixel pattern, color filter and method for producing the same, and liquid crystal display device - Google Patents

Abstract

The present invention provides a photo sensitive resin composition with excellent taper angle, a method for producing a pixel pattern and a liquid crystal display device. The photo sensitive resin composition comprises a pigment (A), an alkali-soluble resin (B), a compound having an unsaturated ethylenically group (C), a photoinitiator (D) and a solvent (E).

Description

Method for producing pixel pattern, color filter and its producing method and liquid crystal display device

The present invention provides a photosensitive resin composition with good gradient angle, and a method for preparing a pixel pattern and a color filter.

A known method for producing a cured film having a fine pattern such as an interlayer insulating film, a protective film, a spacer or a color filter is to apply a photosensitive resin composition in which a pigment is dispersed on a substrate to form a coating film, and then irradiate (expose) the coating film with radiation using a photomask, and then obtain a cured film by developing.

However, in the above exposure process, when using a conventional high-pressure mercury lamp or a metal halide lamp as a UV light source, the photopolymerization initiator contained in the photosensitive resin composition will be sublimated, and these sublimates will adhere to the photomask, resulting in the defect that the expected pattern shape cannot be formed. In addition, when the sublimates adhere to the photomask, the production line of the cured film must be temporarily stopped to facilitate the cleaning of the mask, which will reduce production efficiency.

During the exposure process, the sublimation of the photopolymerization initiator is caused by the use of a conventional ultraviolet light source, which emits infrared light and ultraviolet light, wherein the infrared light provides heat to the photopolymerization initiator, thereby causing the sublimation of the photopolymerization initiator.

In order to avoid the above-mentioned sublimation defects of the photopolymerization initiator, Japanese Patent JP 2008-224964 has disclosed a solution, but it still cannot effectively suppress the sublimation defects of the photopolymerization initiator. In addition, the conventional high-pressure mercury lamp has a short life and needs to be replaced frequently, so its cost is also relatively poor.

Secondly, another known method discloses a UV curing resin composition (see International Publication WO 2010/071171 and Japanese Patent JP 2010-126542), which uses a UV light emitting diode that does not emit infrared light as a light source. However, when using this UV LED as an exposure light source, due to the low energy of the irradiated light, even if the surface curing of the cured film is good, there is still a problem of poor curing in the deep part of the film.

In view of this, a method for forming a cured film is desired, which can suppress the sublimation of a photopolymerization initiator and maintain the curability of the surface and deep part of the cured film even when using an ultraviolet light curing device using an ultraviolet light emitting diode, that is, form a cured film with an excellent gradient angle. Furthermore, since the ultraviolet light emitting diode used only needs to be lit when exposure is desired, compared with the energy loss of conventional high-pressure mercury lamps or metal halide lamps that need to be continuously lit, the ultraviolet light emitting diode used in the method for forming a cured film has a better service life and can provide better energy saving performance.

In view of this, one aspect of the present invention is to provide a method for producing a pixel pattern, which uses a photosensitive resin composition with a good gradient angle to form a coating film to form a pixel pattern by exposure. The photosensitive resin composition includes a pigment (A), an alkali-soluble resin (B), a compound containing an ethylenically unsaturated group (C), a photoinitiator (D) and a solvent (E).

Another aspect of the present invention is to provide a method for manufacturing a color filter, which utilizes the above-mentioned photosensitive resin composition to form a pixel pattern layer.

Another aspect of the present invention is to provide a color filter, which is formed by the above-mentioned manufacturing method.

Another aspect of the present invention is to provide a liquid crystal display device, which includes the aforementioned color filter.

According to the above aspect of the present invention, a method for producing a pixel pattern is proposed, wherein a photosensitive resin composition is used to form a coating on a substrate, and the coating is subjected to an exposure process. The exposure process utilizes an ultraviolet light emitting diode to irradiate the coating, the peak wavelength of the ultraviolet light emitting diode is not less than 300 nm, and the illumination of the exposure process is 50 mW/cm ² to 95 mW/cm ^2. The photosensitive resin composition comprises a pigment (A), an alkali-soluble resin (B), a compound containing an ethylenically unsaturated group (C), a photoinitiator (D), and a solvent (E).

How to create pixel patterns

First, prepare a substrate. The substrate may be a transparent glass substrate such as borosilicate glass, borosilicate glass, alkali-free glass, quartz glass, synthetic quartz glass, sodium glass or white sapphire. In addition, transparent resin films such as acrylic acid such as polymethyl methacrylate, polyamide, polyacetal, polybutylene terephthalate, polyethylene terephthalate, polyethylene naphthalate, triacetyl cellulose, syndiotactic polystyrene, polyphenylene sulfide, polyether ketone, polyether ether ketone, fluororesin, polyether nitrile, polycarbonate, modified polyphenylene ether, polycyclohexene, polynorbornene resin, polysulfone, polyethersulfone, polyarylate, polyamide imide, polyether imide or thermoplastic polyimide may also be used. In particular, alkali-free glass is preferably used because it is a material with a small thermal expansion coefficient and is excellent in dimensional stability and high-temperature heat treatment characteristics.

According to the requirements, in addition to being treated with chemicals such as silane coupling agents or plasma, the substrate may also be pre-treated in advance to form a silicon dioxide film using an appropriate method such as ion plating, sputtering, gas phase reaction or vacuum evaporation.

Next, a light-shielding layer (black matrix) is formed on the substrate to separate the parts that form pixels. For example, a metal (chromium metal) film formed by sputtering or vapor deposition is processed into the desired pattern using photoetching. Alternatively, a photosensitive composition containing a black colorant is applied to the substrate, and the desired pattern is formed using photoetching. The film thickness of the light-shielding layer composed of the metal film is generally preferably 0.1 μm to 0.2 μm. Secondly, the film thickness of the light-shielding film formed using the black photosensitive composition is preferably about 1 μm. In addition, there are also situations where a light-shielding layer is not required, and in this case, the step of forming the light-shielding layer can be omitted.

Then, a colored photosensitive composition is coated on the aforementioned substrate, and then pre-baked to evaporate the solvent and form a coating film.

When the colored photosensitive composition is applied to the substrate, a spray coating method, a roller coating method, a spin coating method (spin coating method), a slot-die coating method, or a rod coating method can be appropriately selected. From the viewpoint of obtaining a coating having a uniform film thickness, the spin coating method or the slot-die coating method is preferably used.

Pre-baking is usually performed in combination with reduced pressure drying and heat drying. Reduced pressure drying is generally performed at a pressure as low as 50 Pa to 200 Pa. Heat drying conditions are generally performed at a temperature of 70°C to 110°C using a heating plate for about 1 minute to 10 minutes. The thickness of the applied coating is generally 0.6 μm to 8.0 μm as the film thickness after drying, and preferably 1.2 μm to 5.0 μm.

In addition, other examples of forming a coating of a colored photosensitive composition on a substrate include methods using an inkjet method disclosed in Japanese Patent Publication No. JP 7-318723 and/or Japanese Patent Publication No. JP 2000-310706. In this method, a barrier layer having a light-shielding function is first formed on the surface of the substrate. Then, a colored photosensitive composition is sprayed in the barrier layer, for example, using an inkjet device. Then, a pre-bake is performed to evaporate the solvent. The method and conditions of the pre-bake are the same as those in the aforementioned embodiment.

The aforementioned interlayer not only has a light-shielding function, but also has the effect of preventing the various colored photosensitive compositions sprayed into the divided areas from mixing. Therefore, compared with the light-shielding layer (black matrix) used in the aforementioned embodiment, the interlayer has a thicker film thickness. The interlayer is generally formed using a black photosensitive composition. In addition, other embodiments of forming a coating of a colored photosensitive composition on a substrate can also be cited, such as the dry film method disclosed in Japanese Patent Publication No. JP Hei 9-5991. In this method, a colored photosensitive composition is coated on a thin film support, and pre-baked to evaporate the solvent, thereby forming a dry film containing the colored photosensitive composition on the support. Then, a lamination machine is used to laminate the support body with the colored photosensitive composition layer formed thereon on the substrate for forming the color filter. Then, the colored photosensitive composition layer is peeled off from the support body to transfer the colored photosensitive composition layer to the substrate. The method of coating the colored photosensitive composition on the support body, the method and conditions of pre-baking can be the same as those in the above-mentioned embodiment.

Exposure process

After the aforementioned step of forming the coating, at least a portion of the formed coating is exposed through a photomask having a prescribed pattern. The present invention is characterized in that the exposure light source utilized is an ultraviolet light emitting diode. An ultraviolet light emitting diode is a light emitting diode that emits ultraviolet light. There is no particular limitation on the ultraviolet light emitting diode that can be utilized, provided that the ultraviolet light emitted can be photosensitized by the photopolymerization initiator described later. However, in order to obtain a color filter having superior chromaticity characteristics, an ultraviolet light emitting diode having a peak wavelength of the emitted ultraviolet light of 300 nm or more is preferred, particularly an ultraviolet light emitting diode having a peak wavelength in the range of 350 nm to 400 nm. In the present invention, by using an ultraviolet light emitting diode having the above-mentioned luminescent characteristics as an exposure light source, the decomposition of the dye during the exposure step can be suppressed. The "peak wavelength" mentioned above refers to the wavelength at the maximum luminescent intensity in the luminescent spectrum, and it can be measured using a commercially available spectrophotometer.

The exposure amount in the method for forming the pixel pattern of the present invention is generally 10 J/m ² to 10,000 J/m ² , and the illumination of the exposure process can be 50 mW/cm ² to 95 mW/cm ^2. When the illumination of the exposure process is not within the aforementioned range, the formed pixel pattern has a poor gradient angle. The irradiation device of the ultraviolet light emitting diode can be, for example, a product sold by International Electric Co., Ltd.

After the exposure process, the following steps may be performed as needed: a process of developing the exposed coating (hereinafter also referred to as “developing process”); and/or a process of post-baking the coating.

Development process

After the development process, the coating is developed with a developer to dissolve and remove the unexposed part of the coating. The developer is preferably an alkaline developer, such as an aqueous solution of sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo[5.4.0]-7-undecene, 1,5-diazabicyclo[4.3.0]-5-nonane, etc. A water-soluble organic solvent such as methanol or ethanol, or a surfactant, etc. can also be added to the alkaline developer in an appropriate amount. Secondly, after the alkaline development treatment, water washing is generally performed.

The developing method may be, for example, a spray developing method, a mist developing method, a dipping developing method, or a puddle developing method. The developing conditions may be, for example, 5 seconds to 300 seconds at room temperature. In addition, when the coating of the colored photosensitive composition is formed by the aforementioned inkjet method, the developing step is not required and can be omitted.

Post-baking step for the coating

After the development process, or after the coating is formed by the inkjet method and the exposure process is performed, it is preferred to post-bake the patterned coating from the viewpoint of improving the curability. When a hot air heating furnace is used, the post-bake conditions can be set at 150°C to 250°C for about 20 minutes to 40 minutes.

By the aforementioned operation, a pixel pattern can be formed and a pixel array arranged in a predetermined configuration can be formed. In detail, by repeatedly performing the aforementioned steps on the same substrate with a photosensitive composition containing a red colorant, a green colorant or a blue colorant, a color filter with a pixel pattern of the three primary colors of red, green and blue and arranged in a predetermined configuration can be produced. However, in the embodiment of the present invention, the order of forming the pixel patterns of each color on the substrate is not limited to the above-mentioned exemplary order. The order of forming the pixel patterns of each color can be appropriately changed.

The film thickness of the pixel pattern formed by the above operation is generally 0.5 μm to 5.0 μm, and preferably 1.0 μm to 3.0 μm.

In addition, in the present invention, the pixel pattern constituting the color filter is not limited to red, green and blue, and it can also be a pixel pattern using yellow, magenta and cyan as the three primary colors. Secondly, in addition to the coloring pattern corresponding to the pixels of the three primary colors, a coloring pattern of a fourth or fifth color can also be formed. For example, the content disclosed in the Japanese Patent Publication No. JP 2005-523465, in addition to the coloring pattern corresponding to the pixels of the three primary colors such as red, green and blue, can be configured with a fourth pixel (yellow pixel) or a fifth pixel (cyan pixel) for expanding the color expression range.

In the pixel pattern formed by the above operation, a protective film is further provided to improve the display characteristics of the display element. The protective film can be an organic film or an organic-inorganic hybrid film formed by a curable composition, or an inorganic film such as a _SiNx film and a _SiOx film. In the embodiment of the present case, it is preferred to use a curable composition to form the protective film.

The method of forming the protective film using the curable resin composition may be, for example, the method disclosed in Japanese Patent Application Laid-Open No. JP-4-53879 or Japanese Patent Application Laid-Open No. JP-6-192389.

The curable resin composition used to form the protective film may be, for example, a thermosetting resin composition disclosed in Japanese Patent Publication No. JP Hei 3-188153 or Japanese Patent Publication No. JP Hei 4-53879; a photosensitive resin composition disclosed in Japanese Patent Publication No. JP Hei 6-192389 or Japanese Patent Publication No. JP Hei 8-183819; or a curable composition containing polyorganosiloxane disclosed in Japanese Patent Publication No. JP 2006-195420 or Japanese Patent Publication No. JP 2008-208342.

According to the pixel pattern forming method of the present invention, the excellent chromaticity characteristics of dyes and colorants can be expressed without loss. In other words, a color filter with high color purity and high brightness stimulation value (Y) in the CIE color system can be obtained. Therefore, by using the pixel pattern forming method of the present invention, a color filter with excellent chromaticity characteristics can be produced. The pixel pattern forming method of the present invention can be used, for example, to produce various color filters such as color filters for color liquid crystal display devices, color filters for color separation of solid-state imaging devices, color filters for organic electroluminescent display devices, or color filters for electronic paper, and is particularly suitable for producing color filters used in color liquid crystal display devices using large substrates.

Pigment (A)

The pigment (A) of the present invention can be an inorganic pigment, an organic pigment or a combination thereof.

The inorganic pigment may be a metal compound such as a metal oxide or a metal salt, and may be selected from oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, lead, antimony, composite oxides of the aforementioned metals, and metal salts.

The organic pigment can be selected from C.I. Pigment Yellow 1, 3, 11, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 55, 60, 61, 65, 71, 73, 74, 81, 83, 93, 95, 97, 98, 99, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 126, 127, 128, 129, 138, 139, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168 , 175; C.I. pigment orange 1, 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 61, 63, 64, 71, 73; C.I. pigment red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, 17, 18, 19, 21, 22, 23, 30, 31, 32, 37, 38, 40, 41, 42, 48:1, 48:2, 48:3, 48:4, 49:1, 49:2, 50:1, 52:1, 53:1, 57, 57:1, 57 ：2、58：2、58：4、60：1、63：1、63：2、64：1、81：1、83、88、90：1、97、101、102、104、105、106、108、112、113、114、122、123、144、146、149、150、151、155、166、168、170、171、172、174、175、176、177、178、179、180、185、187、188、190、193、194、202、206、207、208、20 9, 215, 216, 220, 224, 226, 242, 243, 245, 254, 255, 264, 265; C.I. Pigment Violet 1, 14, 19, 23, 29, 32, 33, 36, 37, 38, 39, 40, 50; C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 16, 21, 22, 60, 61, 64, 66; C.I. Pigment Green 7, 36, 37, 42, 58; C.I. Pigment Brown 23, 25, 28; and C.I. Pigment Black 1, 7. The above organic pigments may be used alone or in combination.

The average particle size of the pigment (A) is preferably 10 nm to 200 nm, more preferably 20 nm to 150 nm, and particularly preferably 30 nm to 130 nm.

Based on 100 parts by weight of the total usage of the alkali-soluble resin (B), the usage of the pigment (A) is 5 to 300 parts by weight, preferably 10 to 250 parts by weight, and more preferably 15 to 200 parts by weight.

If necessary, the pigment (A) can also selectively use a dispersant, such as a cationic, anionic, non-ionic, amphoteric, polysiloxane or fluorine-based surfactant.

The aforementioned surfactants may include but are not limited to polyethylene oxide alkyl ethers such as polyethylene oxide lauryl ether, polyethylene oxide stearyl ether, and polyethylene oxide oleyl ether; polyethylene oxide alkyl phenyl ether surfactants such as polyethylene oxide octyl phenyl ether and polyethylene oxide nonyl phenyl ether; polyethylene glycol diester surfactants such as polyethylene glycol dilaurate and polyethylene glycol distearate; sorbitan fatty acid ester surfactants; fatty acid-modified polyester surfactants; tertiary amine-modified polyurethane surfactants; Shin-Etsu Chemical Co., Ltd., product model KP; Toray Dow Corning Silicon, product model SF-8427; Kyoeisha Oil and Fat Chemical Co., Ltd., product model Polyflow; Tochem Products Co., Ltd.) under the model F-Top; Dainippon Ink Chemicals under the model Megafac; Sumitomo 3M under the model Fluorad; Asahi Glass under the model Asahi Guard and Surflon. The aforementioned surfactants may be used alone or in combination.

Alkaline soluble resin (B)

The alkali-soluble resin (B) of the present invention is obtained by reacting an ethylenically unsaturated monomer (B-1) having one or more carboxylic acids or carboxylic anhydrides, an ethylenically unsaturated monomer (B-2) having an epoxy group, and other copolymerizable ethylenically unsaturated monomers (B-3).

In the aforementioned ethylenically unsaturated monomer (B-1) having one or more carboxylic acids or carboxylic anhydrides, the ethylenically unsaturated monomer having one or more carboxylic acids may include but is not limited to unsaturated monocarboxylic acid compounds, unsaturated polycarboxylic acid compounds, polycyclic compounds having an unsaturated group and one carboxylic acid group, or polycyclic compounds having an unsaturated group and multiple carboxylic acid groups.

The unsaturated monocarboxylic acid compound may include but is not limited to (meth) acrylic acid, crotonic acid, α-chloroacrylic acid, ethyl acrylic acid, cinnamic acid, 2-(meth)acryloyloxy ethyl succinate monoester, 2-(meth)acryloyloxy ethyl succinate monoester, 2-(meth)acryloyloxy hexahydrophthalate, 2-(meth)acryloyloxy phthalate or omega-carboxylic acid-based polycaprolactone polyol monoacrylate, etc. The omega-carboxylic acid-based polycaprolactone polyol monoacrylate may be manufactured by East Asia Synthetics and is a product of model ARONIX M-5300.

The unsaturated polycarboxylic acid compound may include but is not limited to maleic acid, fumaric acid, methyl fumaric acid, itaconic acid or leuconic acid.

The aforementioned polycyclic compound having an unsaturated group and a carboxylic acid group may include but is not limited to 5-carboxylic acid bicyclo[2.2.1]hept-2-ene, 5-carboxylic acid-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxylic acid-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxylic acid-6-methylbicyclo[2.2.1]hept-2-ene or 5-carboxylic acid-6-ethylbicyclo[2.2.1]hept-2-ene.

The polycyclic compound having an unsaturated group and a plurality of carboxylic acid groups may include 5,6-dicarboxylic acid bicyclo[2.2.1]hept-2-ene and the like.

Preferably, the aforementioned ethylenically unsaturated monomer having one or more carboxylic acids is selected from acrylic acid, methacrylic acid, 2-methacryloylethoxysuccinate, 2-methacryloylethoxyhexahydrophthalate, or any combination thereof.

In the aforementioned ethylenically unsaturated monomer having one or more carboxylic acids or carboxylic anhydrides (B-1), the ethylenically unsaturated monomer having one or more carboxylic anhydrides may include but is not limited to unsaturated carboxylic anhydride compounds or polycyclic compounds having an unsaturated group and a carboxylic anhydride.

The unsaturated carboxylic anhydride compound may include but is not limited to maleic anhydride, fumaric anhydride, methylfumaric anhydride, itaconic anhydride or citric anhydride, etc. The polycyclic compound having an unsaturated group and a carboxylic anhydride may include but is not limited to 5,6-dicarboxylic anhydride bicyclo[2.2.1]hept-2-ene, etc.

Preferably, the ethylenically unsaturated monomer having one or more carboxylic anhydride groups is maleic anhydride.

The aforementioned ethylenically unsaturated monomer (B-1) having one or more carboxylic acids or carboxylic anhydrides may be used alone or in combination of plural types.

In a specific example of the present invention, based on the total usage of 100 parts by weight of the copolymerization monomers such as the ethylenically unsaturated monomer having one or more carboxylic acids or carboxylic anhydrides (B-1), the ethylenically unsaturated monomer having an epoxy group (B-2) and the other copolymerizable ethylenically unsaturated monomers (B-3), the usage of the ethylenically unsaturated monomer having one or more carboxylic acids or carboxylic anhydrides (B-1) is 10 to 60 parts by weight, preferably 15 to 55 parts by weight, and more preferably 20 to 50 parts by weight.

The ethylenically unsaturated monomer (B-2) having an epoxy group may include, but is not limited to, a (meth)acrylate compound having an epoxy group, an α-alkylacrylate compound having an epoxy group, or a glycidyl ether compound.

The aforementioned (meth)acrylate compound having an epoxy group may include but is not limited to epoxypropyl (meth)acrylate, 2-methyl epoxypropyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, 6,7-epoxyheptyl (meth)acrylate, 3,4-epoxyhexyl (meth)acrylate or 3,4-epoxyhexylmethyl (meth)acrylate.

The aforementioned α-alkyl acrylate compound having an epoxy group may include but is not limited to α-ethyl glycidyl acrylate, α-n-propyl glycidyl acrylate, α-n-butyl glycidyl acrylate, or α-ethyl acrylate-6,7-epoxyheptyl.

The aforementioned glycidyl ether compound may include but is not limited to o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, and the like.

The ethylenically unsaturated monomer (B-2) having an epoxy group may be used alone or in combination of two or more.

Preferably, the aforementioned ethylenically unsaturated monomer having an epoxy group (B-2) is selected from glycidyl methacrylate, 2-methylglycidyl methacrylate, 3,4-epoxyhexylmethyl methacrylate, 6,7-epoxyheptyl methacrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether or any combination thereof.

In a specific example of the present invention, based on the total usage of 100 parts by weight of the copolymerization monomers such as the ethylenically unsaturated monomer (B-1) having one or more carboxylic acids or carboxylic anhydrides, the ethylenically unsaturated monomer (B-2) having an epoxy group, and the other copolymerizable ethylenically unsaturated monomer (B-3), the usage of the ethylenically unsaturated monomer (B-2) having an epoxy group is 1 to 50 parts by weight, preferably 3 to 45 parts by weight, and more preferably 5 to 40 parts by weight.

The aforementioned other copolymerizable ethylenically unsaturated monomers (B-3) may include but are not limited to alkyl (meth)acrylates, cycloaliphatic (meth)acrylates, aryl (meth)acrylates, unsaturated dicarboxylates, hydroxyalkyl (meth)acrylates, polyethers having (meth)acrylate groups, styrene compounds, or unsaturated compounds other than the above compounds.

The alkyl (meth)acrylate mentioned above may include but is not limited to methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate or t-butyl (meth)acrylate.

The above-mentioned cyclo(meth)acrylate may include but is not limited to cyclohexyl(meth)acrylate, 2-methylcyclohexyl(meth)acrylate, dicyclopentyl(meth)acrylate (or tricyclo[5.2.1.0 ^2,6 ]dec-8-yl(meth)acrylate), dicyclopentyloxyethyl(meth)acrylate, isobornyl(meth)acrylate or tetrahydrofuran(meth)acrylate.

The aryl (meth)acrylate may include but is not limited to phenyl (meth)acrylate or benzyl methacrylate.

The unsaturated dicarboxylic acid ester may include but is not limited to diethyl maleate, diethyl fumarate or diethyl itaconate.

The aforementioned hydroxyalkyl (meth)acrylate may include but is not limited to 2-hydroxyethyl (meth)acrylate or 2-hydroxypropyl (meth)acrylate.

The aforementioned polyether having a (meth)acrylate group may include but is not limited to polyethylene glycol mono(meth)acrylate or polypropylene glycol mono(meth)acrylate.

The aforementioned styrene-based compounds may include but are not limited to styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene or p-methoxystyrene.

Unsaturated compounds other than the above compounds may include but are not limited to acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl ethyl ester, 1,3-butadiene, isoprene, 2,3-dimethyl 1,3-butadiene, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6- -maleimido hexanoate, N-succinimidyl-3-maleimido propionate, N-(9-acridinyl)maleimide, N-octylmaleimide, N-cyclohexylmaleimide or N-phenylmaleimide, etc.

The above-mentioned other copolymerizable ethylenically unsaturated monomers (B-3) may be used alone or in combination of plural kinds.

Preferably, the other copolymerizable ethylenically unsaturated monomer (B-3) is selected from methyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, tert-butyl (meth)acrylate, benzyl (meth)acrylate, dicyclopentyl (meth)acrylate, isobornyl methacrylate, dicyclopentyloxyethyl (meth)acrylate, styrene, p-methoxystyrene or any combination thereof.

In a specific example of the present invention, based on the total usage of the copolymerization monomers such as the ethylenically unsaturated monomer (B-1) having one or more carboxylic acids or carboxylic anhydrides, the ethylenically unsaturated monomer (B-2) having an epoxy group and the other copolymerizable ethylenically unsaturated monomer (B-3) being 100 parts by weight, the usage of the other copolymerizable ethylenically unsaturated monomer (B-3) is 10 to 90 parts by weight, preferably 15 to 85 parts by weight, and more preferably 20 to 80 parts by weight.

When preparing the alkali-soluble resin (B), a solvent may be used. The solvent may be used alone or in combination. The solvent includes but is not limited to (poly)alkylene glycol monoalkyl ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol n-propyl ether, diethylene glycol n-butyl ether, triethylene glycol methyl ether, triethylene glycol ethyl ether, propylene glycol methyl ether, propylene glycol ethyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol n-butyl ether, tripropylene glycol methyl ether, tripropylene glycol ethyl ether; ethylene glycol methyl ether acetate, ethylene glycol ethyl ether acetate, propylene glycol methyl ether acetate; acetate; PGMEA), propylene glycol ethyl ether acetate, etc.; other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, etc.; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, etc.; alkyl lactates such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, etc.; methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate (ethyl 3-ethoxypropionate; EEP), ethyl ethoxylate, ethyl hydroxylate, methyl 2-hydroxy-3-methylbutyrate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl acetate, isoamyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetylacetate, ethyl acetylacetate, ethyl 2-methoxybutyrate and other esters; aromatic hydrocarbons such as toluene and xylene; amides such as nitrogen-methylpyrrolidone (NMP), nitrogen, nitrogen-dimethylformamide (DMF), or nitrogen, nitrogen-dimethylacetamide (DMAC), etc. Preferably, the solvent is selected from propylene glycol methyl ether acetate, 3-ethoxyethyl propionate, or a combination thereof. (Poly) alkylene glycol monoalkyl ethers refer to alkylene glycol monoalkyl ethers or polyalkylene glycol monoalkyl ethers. (Poly) alkylene glycol monoalkyl ether acetates refer to alkylene glycol monoalkyl ether acetates or polyalkylene glycol monoalkyl ether acetates.

The initiator used in the preparation of the alkali-soluble resin (B) is generally a free radical polymerization initiator, for example: azo compounds such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis-2-methylbutyronitrile (AMBN); peroxide compounds such as dibenzoyl peroxide.

In addition, the weight average molecular weight of the alkali-soluble resin (B) measured by gel permeation chromatography (GPC) in terms of polystyrene is generally 1,000 to 35,000, preferably 3,000 to 30,000, and more preferably 5,000 to 25,000.

Compounds containing ethylenically unsaturated groups (C)

The ethylenically unsaturated group-containing compound (C) of the present invention may include an unsaturated compound having at least one ethylenically unsaturated group and an unsaturated compound having at least two ethylenically unsaturated groups.

Specific examples of the unsaturated compound having at least one ethylenically unsaturated group include, but are not limited to, acrylamide, acrylamide morpholine, methacrylamidoline, 7-amino-3,7-dimethyloctyl acrylate, 7-amino-3,7-dimethyloctyl methacrylate, isobutoxymethylacrylamide, isobutoxymethylmethacrylamide, isobornyloxyethyl acrylate, isobornyloxyethyl methacrylate, isobornyl acrylate, isobornyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, and 1,2-dimethylhexyl acrylate. , ethyl diglycol acrylate, ethyl diglycol methacrylate, tert-octyl acrylamide, tert-octyl methacrylamide, diacetone acrylamide, diacetone methacrylamide, dimethylamino acrylate, dimethylamino methacrylate, dodecyl acrylate, dodecyl methacrylate, dicyclopentenyloxyethyl acrylate, dicyclopentenyloxyethyl methacrylate, dicyclopentenyl acrylate, dicyclopentenyl methacrylate, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, tetrachlorophenyl acrylate, methyl Tetrachlorophenyl acrylate, 2-tetrachlorophenoxyethyl acrylate, 2-tetrachlorophenoxyethyl methacrylate, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, tetrabromophenyl acrylate, tetrabromophenyl methacrylate, 2-tetrabromophenoxyethyl acrylate, 2-tetrabromophenoxyethyl methacrylate, 2-trichlorophenoxyethyl acrylate, 2-trichlorophenoxyethyl methacrylate, tribromophenyl acrylate, tribromophenyl methacrylate, 2-tribromophenoxyethyl acrylate, 2-tribromophenoxyethyl methacrylate , 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, vinyl caprolactam, N-vinyl pyroxanone, phenoxyethyl acrylate, phenoxyethyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, polyethylene glycol monoacrylate, polyethylene glycol monomethacrylate, polypropylene glycol monoacrylate, polypropylene glycol monomethacrylate, bornyl acrylate, or bornyl methacrylate. The unsaturated compound having at least one ethylenically unsaturated group may be used alone or in combination of a plurality of them.

Specific examples of the unsaturated compound having at least two ethylenically unsaturated groups may include, but are not limited to, ethylene glycol diacrylate, ethylene glycol dimethacrylate, dicyclopentenyl diacrylate, dicyclopentenyl dimethacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, tris(2-hydroxyethyl)isocyanate diacrylate, tris(2-hydroxyethyl)isocyanate dimethacrylate, and tris(2-hydroxyethyl)isocyanate dimethacrylate. acrylate, tris(2-hydroxyethyl) isocyanate triacrylate, tris(2-hydroxyethyl) isocyanate trimethacrylate, caprolactone-modified tris(2-hydroxyethyl) isocyanate triacrylate, caprolactone-modified tris(2-hydroxyethyl) isocyanate trimethacrylate, trihydroxymethylpropyl triacrylate, trihydroxymethylpropyl trimethacrylate, ethylene oxide (hereinafter referred to as EO)-modified trihydroxymethyl propylene oxide (hereinafter referred to as PO) modified trimethacrylate trihydroxymethylpropyl, EO modified trimethacrylate trihydroxymethylpropyl, PO modified trimethacrylate trihydroxymethylpropyl, triethylene glycol diacrylate, triethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, polyester diacrylate, polyester dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, dipentaerythritol hexaacrylate (dipentaerythritol hexaacrylate; DPHA), dipentaerythritol hexamethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol tetraacrylate, dipentaerythritol tetramethacrylate, caprolactone-modified dipentaerythritol hexaacrylate, caprolactone-modified dipentaerythritol hexamethacrylate, caprolactone-modified dipentaerythritol pentaacrylate, caprolactone-modified dipentaerythritol pentamethacrylate, tetraacrylate ditrihydroxymethylpropyl, tetramethacrylate ditrihydroxymethylpropyl, EO-modified bisphenol A diacrylate, EO-modified bisphenol A dimethacrylate, PO-modified bisphenol A diacrylate, PO-modified bisphenol A dimethacrylate, EO-modified hydrogenated bisphenol A diacrylate, EO-modified hydrogenated bisphenol A dimethacrylate, PO-modified hydrogenated bisphenol A diacrylate, PO-modified hydrogenated bisphenol A dimethacrylate, PO-modified glycerol tripropionate, EO-modified bisphenol F diacrylate, EO-modified bisphenol F dimethacrylate, phenolic polyglycidyl ether acrylate, phenolic polyglycidyl ether methacrylate, the product of model TO-1382 manufactured by Toagosei Co., Ltd., or the product of model KAYARAD DPCA-12, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60 or KAYARAD DPCA-120 manufactured by Nippon Kayaku Co., Ltd., etc. The unsaturated compound having at least two ethylenically unsaturated groups may be used alone or in combination of two or more.

Preferably, the ethylenically unsaturated group-containing compound (C) is selected from trihydroxymethylpropyl triacrylate, EO-modified trihydroxymethylpropyl triacrylate, PO-modified trihydroxymethylpropyl triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, dipentaerythritol tetraacrylate, caprolactone-modified dipentaerythritol hexaacrylate, ditrihydroxymethylpropyl tetraacrylate, PO-modified glycerol tripropionate, KAYARAD DPCA-12, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60 or KAYARAD DPCA-120 or any combination thereof.

The above-mentioned ethylenically unsaturated group-containing compound (C) may be used alone or in combination of plural kinds.

Based on 100 parts by weight of the total amount of the alkali-soluble resin (B), the amount of the ethylenically unsaturated group-containing compound (C) is 20 to 200 parts by weight, preferably 30 to 180 parts by weight, and more preferably 50 to 150 parts by weight.

Photoinitiator (D)

The photoinitiator (D) of the present invention may include, for example, but is not limited to, an oxime ester compound (D-1) represented by the following formula (I), an oxime ester compound (D-2) represented by the following formula (II), an oxime ester compound (D-3) represented by the following formula (III), and other photoinitiators (D-4).

Oxime ester compound (D-1) represented by formula (I)

The photoinitiator (D) may include an oxime ester compound (D-1) as shown in the following formula (I). The oxime ester compound (D-1) as shown in the following formula (I) can usually generate free radicals by light irradiation, and has high sensitivity to i-rays used as a light source during patterning. (I)

In formula (I), _Y1 represents an organic group as shown in the following formula (I-1); _Y2 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; _Y3 represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms. (I-1)

In formula (I-1), Y ₄ represents a monovalent organic group; X ₁ represents an oxygen atom, a sulfur atom or a carbonyl group; and a represents an integer from 0 to 5.

In formula (I), _Y2 preferably represents an alkyl group having 1 to 10 carbon atoms (more preferably 1 to 8 carbon atoms), and more preferably represents a methyl group or a hexyl group. _Y3 preferably represents an alkyl group having 1 to 3 carbon atoms or an aryl group having 6 to 10 carbon atoms, and more preferably represents a methyl group or a phenyl group. In formula (I-1), _X1 preferably represents a sulfur atom; _Y4 preferably represents a hydroxyalkoxy group having 1 to 4 carbon atoms; and a is preferably 0 or 1. Secondly, formula (I-1) may also be, for example, an organic group represented by the following formula (I'-1), wherein _X1 and _Y4 are as defined above and are not further described here. (I'-1)

In some specific examples, the oxime ester compound (D-1) represented by formula (I) may include but is not limited to the compounds represented by the following formula (I-2) and formula (I-3). (I-2) (I-3)

Based on the total usage of the alkali-soluble resin (B) being 100 parts by weight, the usage of the oxime ester compound (D-1) represented by formula (I) can be 1 to 100 parts by weight, preferably 5 to 90 parts by weight, and more preferably 10 to 80 parts by weight.

When the photosensitive resin composition of the present invention comprises the oxime ester compound (D-1) as shown in formula (I), the formed pixel pattern has a better gradient angle.

Oxime ester compound (D-2) represented by formula (II)

The photoinitiator (D) may include an oxime ester compound (D-2) represented by the following formula (II). (II)

In formula (II), _Z1 represents an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, and a tolyl group; _Z2 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; and _Z3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted carbazolyl group.

The substituents of the aforementioned phenyl, fluorenyl and carbazolyl groups may include an alkyl group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms), an alkoxy group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms), a nitro group, or a benzyl group. Among them, the alkyl group and the alkoxy group may be optionally substituted by fluorine, and the benzyl group may be substituted by an alkyl group having 1 to 4 carbon atoms. In addition, the benzene ring of the fluorenyl and carbazolyl groups may be fused with another benzene ring. For example, it may be a benzocarbazolyl group.

From the viewpoint of improving photocurability, the oxime ester compound (D-2) represented by formula (II) is preferably a compound represented by the following formula (II-1). (II-1)

In formula (II-1), _Z1 and _Z2 are as defined above. _Z4 represents an alkyl group having 1 to 6 carbon atoms, and is preferably an ethyl group; _Z5 represents an alkyl group having 1 to 12 carbon atoms or an organic group having an acetal bond, and is preferably a methyl group or a substituent corresponding to _Z5 in the compound shown in formula (II-1-2); b represents an integer from 1 to 3, and is preferably 1 or 2.

In some specific examples, the oxime ester compound (D-2) represented by the above formula (II) may include but is not limited to the compounds represented by the following formula (II-1-1) or (II-1-2), which are respectively manufactured by BASF and have the model number IRGACURE OXE-02, and manufactured by ADEKA and have the model number Optomer N-1919. (II-1-1) (II-1-2)

Preferably, the oxime ester compound (D-2) represented by formula (II) may include but is not limited to the compound represented by the following formula (II-1-3). (II-1-3)

Based on the total usage of the alkali-soluble resin (B) being 100 parts by weight, the usage of the oxime ester compound (D-2) represented by formula (II) is 1 to 100 parts by weight, preferably 5 to 90 parts by weight, and more preferably 10 to 80 parts by weight.

When the photosensitive resin composition of the present invention comprises an oxime ester compound (D-2) as represented by formula (II), the formed pixel pattern has a better gradient angle.

Oxime ester compound (D-3) represented by formula (III)

The photoinitiator (D) may include an oxime ester compound (D-3) represented by the following formula (III). (III) In formula (III), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, COR ₁₆ , or a group represented by the following formula (III'-1); (III'-1) or R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ or R ₇ and R ₈ independently and collectively represent a group represented by the following formula (III'-2); (III'-2) with the proviso that at least one pair of _R1 and _R2 , _R2 and _R3 , _R3 and _R4 , _R5 and _R6 , _R6 and _R7 or _R7 and _R8 is a group as represented by formula (III'-2), _R9 , _R10 , _R11 and _R12 are independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group having 1 to 20 carbon atoms is unsubstituted or substituted by one or more of the following groups: a halogen or a phenyl group; or _R9 , _R10 , _R11 and _R12 are independently an unsubstituted phenyl group or a phenyl group substituted by one or more of the following groups: an alkyl group having 1 to 6 carbon atoms or a halogen group; _X2 is CO or a single bond; R _{R 13} represents an alkyl group having 1 to 20 carbon atoms, which is unsubstituted or substituted by one or more of the following groups: halogen, R ₁₇ , COOR ₁₇ or OR ₁₇ ; or R ₁₃ represents an alkyl group having 2 to 20 carbon atoms, which is doped with one or more O or CO, wherein the doped alkyl group having 2 to 20 carbon atoms is unsubstituted or substituted by one or more halogens; or R ₁₃ represents a phenyl group or a naphthyl group, each of which is unsubstituted or substituted by one or more of the following groups: an alkyl group having 1 to 20 carbon atoms or a halogenated alkyl group having 1 to 4 carbon atoms; R ₁₄ represents a hydrogen atom, an alkoxy group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms; R _{R 15} represents an aryl group having 6 to 20 carbon atoms, each of which is unsubstituted or substituted by one or more of the following groups: halogen, halogenated alkyl group having 1 to 4 carbon atoms, OR ₁₇ , alkyl group having 2 to 20 carbon atoms doped with one or more O; or each of which is substituted by an alkyl group having 1 to 20 carbon atoms, the alkyl group having 1 to 20 carbon atoms being unsubstituted or substituted by one or more of the following groups: halogen, COOR ₁₇ , phenyl or OR ₁₇ ; or R ₁₅ represents a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms; or R ₁₅ represents an alkyl group having 1 to 20 carbon atoms, which is unsubstituted or substituted by one or more of the following groups: halogen or cycloalkyl group having 3 to 8 carbon atoms; R _{R 16} represents an aryl group having 6 to 20 carbon atoms, each of which is unsubstituted or substituted by one or more of the following groups: halogen, halogenated alkyl group having 1 to 4 carbon atoms, OR ₁₇ ; or each of which is substituted by one or more alkyl group having 1 to 20 carbon atoms, the alkyl group having 1 to 20 carbon atoms being unsubstituted or substituted by one or more of the following groups: halogen or OR ₁₇ ; R ₁₇ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, which is unsubstituted or substituted by one or more of the following groups: halogen or cycloalkyl group having 3 to 20 carbon atoms doped with one or more O groups; or R ₁₇ represents an alkyl group having 2 to 20 carbon atoms doped with one or more O groups; or R ₁₇ represents a phenyl group, each of which is unsubstituted or substituted by one or more of the following groups: halogen, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms; provided that at least one group represented by formula (III'-1) is present in formula (III).

The compound of formula (III) is characterized in that it contains one or more annelated unsaturated rings on the carbazole portion. In other words, at least one pair of _R1 and _R2 , _R2 and _R3 , _R3 and _R4 , _R5 and _R6 , _R6 and _R7 , or _R7 and _R8 is a group represented by formula (III'-2).

The aforementioned alkyl group with a carbon number of 1 to 20 may be a linear alkyl group or a branched alkyl group. In some specific examples, the alkyl group with a carbon number of 1 to 20 may include but is not limited to methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2,4,4-trimethylpentyl, 2-ethylhexyl, octyl, nonyl, decyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, eicosyl, or other appropriate alkyl groups.

The aforementioned halogenated alkyl group having 1 to 4 carbon atoms may be the aforementioned alkyl group having 1 to 4 carbon atoms substituted with a halogen as defined below. The halogenated _alkyl group may be, for example, monohalogenated or _{polyhalogenated} until all hydrogen atoms are substituted with halogens. Its structure may be, for example, _CzHxHaly , wherein x+y=2z+1, and Hal represents a halogen (preferably F). For example, the halogenated alkyl group having 1 to 4 carbon atoms may include but is not limited to chloromethyl, trichloromethyl, trifluoromethyl, 2-bromopropyl, or other suitable halogenated alkyl groups, and may preferably be trifluoromethyl or trichloromethyl.

The aforementioned alkyl group with 2 to 20 carbon atoms doped with one or more O atoms may be doped with O 1 to 9 times, 1 to 5 times, 1 to 3 times, 1 time or 2 times, for example. Two doped O atoms may be separated by at least one methylene group, and preferably by at least two methylene groups (i.e., ethylene groups). The alkyl groups are straight chain or branched chain. For example, an alkyl group having 2 to 20 carbon atoms which is doped with one or more O atoms may have the following structural units: _-CH2 - _{CH2 -O-CH2CH3, -(CH2CH2O)d-CH3 (wherein d represents 1 to 9), -(CH2-CH2O ) 7 - CH2CH3 , -CH2 - CH ( CH3 ) -O - CH2} - _CH2CH3 , or _-CH2 -CH( _CH3 )-O- _CH2 - _CH3 .

The alkoxy group having 1 to 12 carbon atoms is an alkyl group having 1 to 12 carbon atoms substituted by one O atom.

In some specific examples, the aforementioned aryl group having 6 to 20 carbon atoms may be, for example, phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, chrysene, tetraphenyl, triphenyl, or other suitable aryl groups, especially phenyl or naphthyl, and preferably phenyl. The naphthyl group may be 1-naphthyl or 2-naphthyl.

The substituted aryl groups (e.g. phenyl, naphthyl or aryl groups with 6 to 20 carbon atoms) may be substituted 1 to 7 times, 1 to 6 times or 1 to 4 times, respectively, in particular 1, 2 or 3 times. Obviously, the aryl groups as defined cannot have more substituents than the free positions at the aryl ring.

The substituent on the phenyl ring is preferably in position 4 on the phenyl ring, or in a 3,4-, 3,4,5-, 2,6-, 2,4- or 2,4,6-bonding configuration.

An interrupted group which is doped once or more may, for example, be doped 1 to 19 times, 1 to 15 times, 1 to 12 times, 1 to 9 times, 1 to 7 times, 1 to 5 times, 1 to 4 times, 1 to 3 times, 1 time, or 2 times. Obviously, the number of intervening atoms depends on the number of carbon atoms of the group to be interrupted). A substituted group which is substituted once or more may, for example, have 1 to 7, 1 to 5, 1 to 4, 1 to 3, 1, or 2 identical or different substituents.

A radical substituted by one or more defined substituents is intended to have one substituent or multiple substituents that are the same or different as defined. Halogen can be fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, and preferably fluorine or chlorine. If R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ or R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ of formula (III) are independently and jointly a radical as shown in formula (III'-2), the oxime ester compound (D-3) shown in formula (III) can, for example, have a structure as shown in the following formulas (III-a) to (III-i). (III-a) (III-b) (III-c) (III-d) (III-e) (III-f) (III-g) (III-h) (III-i)

Preferably, the oxime ester compound (D-3) represented by formula (III) may have a structure represented by formula (III-a), formula (III-b) or formula (III-c), more preferably a structure represented by formula (III-a) or formula (III-c), or a structure represented by formula (III-a), formula (III-c) or formula (III-d), and particularly preferably a structure represented by formula (III-a).

For example, R ₁₅ may represent a hydrogen atom, a phenyl group or a naphthyl group, wherein the phenyl group or the naphthyl group is unsubstituted or substituted by an alkyl group having 1 to 8 carbon atoms or OR ₁₇ , respectively; or R ₁₅ represents an alkyl group having 1 to 20 carbon atoms; or R ₁₅ represents an alkyl group having 2 to 20 carbon atoms, and one or more O are mixed therein.

For example, R ₁₆ represents an aryl group having 6 to 20 carbon atoms (preferably phenyl or naphthyl, and more preferably phenyl), each of which is unsubstituted or substituted with one or more of the following groups: halogen, halogenated alkyl group having 1 to 4 carbon atoms, or OR ₁₇ ; or each of which is substituted with one or more alkyl group having 1 to 20 carbon atoms, and the alkyl group having 1 to 20 carbon atoms is unsubstituted or substituted with one or more of the following groups: halogen or OR ₁₇ .

Furthermore, R ₁₆ may represent, for example, phenyl or naphthyl, preferably phenyl or carbazole, wherein phenyl or naphthyl is unsubstituted or substituted by one or more of the following groups: halogen, halogenated alkyl having 1 to 4 carbon atoms, OR ₁₇ or alkyl having 1 to 20 carbon atoms.

R ₁₆ may, for example, represent phenyl or naphthyl, preferably phenyl, each of which is unsubstituted or substituted by one or more of the following groups: halogen, OR ₁₇ or alkyl having 1 to 20 carbon atoms.

Preferably, R ₁₆ is a phenyl group, which is substituted with one or more alkyl groups having 1 to 20 carbon atoms.

R ₁₇ may, for example, represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group having 1 to 20 carbon atoms is unsubstituted or substituted by one or more of the following groups: a halogen or a cycloalkyl group having 3 to 20 carbon atoms which is doped with one or more O groups; or R ₁₇ represents a phenyl group, each of which is unsubstituted or substituted by one or more of the following groups: a halogen, an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

In some specific examples, the oxime ester compound (D-3) represented by formula (III) may include but is not limited to compounds represented by the following formulas (III-1) to (III-22). (III-1) (III-2) (III-3) (III-4) (III-5) (III-6) (III-7) (III-8) (III-9) (III-10) (III-11) (III-12) (III-13) (III-14) (III-15) (III-16) (III-17) (III-18) (III-19) (III-20) (III-21) (III-22)

The aforementioned oxime ester compounds (D-3) may be used alone or in combination of two or more.

Based on the total usage of the alkali-soluble resin (B) being 100 parts by weight, the usage of the oxime ester compound (D-3) represented by formula (III) can be 1 to 100 parts by weight, preferably 5 to 90 parts by weight, and more preferably 10 to 80 parts by weight.

When the photosensitive resin composition includes the oxime ester compound (D-3) represented by formula (III), the formed pixel pattern has a better gradient angle.

Other photoinitiators (D-4)

The photoinitiator (D) of the present invention may optionally contain other photoinitiators (D-4).

The other photoinitiator (D-4) can be selected from acetophenone compounds, biimidazole compounds or a combination of these compounds.

The acetophenone compound can be selected from p-dimethylamino-acetophenone, α,α'-dimethoxyazoxy-acetophenone, 2,2'-dimethyl-2-phenyl-acetophenone, p-methoxy-acetophenone, 2-methyl-1-(4-methylthiophenyl)-2-morpholino-1-propanone, or 2-benzyl-2-N,N-di-methylamino-1-(4-morpholinophenyl)-1-butanone.

The above-mentioned diimidazole compound can be selected from 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-biimidazole, 2,2'-bis(o-fluorophenyl)-4,4',5,5'-tetraphenyl-biimidazole, 2,2'-bis(o-methylphenyl)-4,4',5,5'-tetraphenyl-biimidazole, tetraphenyl-biimidazole), 2,2'-bis(o-methoxy phenyl)-4,4',5,5'-tetraphenyl-biimidazole), 2,2'-bis(o-ethylphenyl)-4,4',5,5'-tetraphenyl-biimidazole), 2,2'-bis(p-methoxyphenyl)-4,4',5,5'-tetraphenyl-biimidazole, 5'-tetraphenyl-biimidazole), 2,2'-bis (2,2',4,4'-tetramethoxyphenyl)-4,4',5,5'-tetraphenyl-biimidazole), 2,2'-bis(2-chlorophenyl)- 4,4',5,5'-tetraphenyl-biimidazole, or 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetra phenyl-biimidazole.

Preferably, the other photoinitiator (D-4) can be 2-methyl-1-(4-methylthiophenyl)-2-morpholino-1-propanone, 2-benzyl-2-nitrogen-dimethylamine-1-(4-morpholinophenyl)-1-butanone, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyldiimidazole, or a combination of these compounds.

The other photoinitiator (D-4) of the present invention may be further added with the following compounds: benzophenone compounds such as thioxanthone, 2,4-diethyl-thioxanthanone, thioxanthone-4-sulfone, benzophenone, 4,4'-bis(dimethylamino)benzophenone, or 4,4'-bis(diethylamino)benzophenone; α-diketone compounds such as benzil or acetyl; acyloin compounds such as benzoin; benzoin methyl ether; acyloin ether compounds such as benzoin methyl ether, benzoin ethyl ether or benzoin isopropyl ether; acylphosphineoxide compounds such as 2,4,6-trimethylbenzoyl-diphenyl-phosphineoxide or bis-(2,6-dimethoxy-benzoyl)-2,4,4-trimethyl-benzyl-phosphine oxide; quinone compounds such as anthraquinone or 1,4-naphthoquinone; phenacyl chloride Halides such as tribromomethyl-phenylsulfone, tris(trichloromethyl)-s-triazine, and peroxides such as di-tertbutylperoxide. Among them, benzophenone compounds are preferred, and 4,4'-bis(diethylamino)benzophenone is the best.

The above-mentioned other photoinitiators (D-4) may be used alone or in combination of two or more.

Based on 100 parts by weight of the total usage of the alkali-soluble resin (B), the usage of the other photoinitiator (D-4) may be 0 to 99 parts by weight, preferably 5 to 95 parts by weight, and more preferably 10 to 90 parts by weight.

Based on 100 parts by weight of the total usage of the alkali-soluble resin (B), the usage of the photoinitiator (D) may be 10 to 100 parts by weight, preferably 15 to 90 parts by weight, and more preferably 20 to 80 parts by weight.

Solvent (E)

The preparation of the photosensitive resin composition of the present invention is usually to dissolve the components other than the pigment (A) in a solvent (E) to prepare a liquid composition, and then add the pigment (A) and mix them evenly. The solvent (E) should be selected to dissolve the alkali-soluble resin (B), the compound containing ethylenically unsaturated groups (C) and the photoinitiator (D), and should not react with these components and have appropriate volatility.

In addition, the solvent (E) may be the same as the solvent used in preparing the alkali-soluble resin (B) and will not be described in detail herein. Preferably, the solvent (E) is selected from propylene glycol methyl ether acetate, cyclohexanone or ethyl 3-ethoxypropionate. The solvent (E) may be used alone or in combination of multiple solvents.

Based on the total usage of the alkali-soluble resin (B) being 100 parts by weight, the usage of the solvent (E) is 500 parts by weight to 5000 parts by weight, preferably 800 parts by weight to 4500 parts by weight, and more preferably 1000 parts by weight to 4000 parts by weight.

Additive(F)

In a preferred embodiment of the present invention, the photosensitive resin composition may optionally contain additives (F), such as fillers, polymer compounds other than the alkali-soluble resin (B), adhesion promoters, antioxidants, ultraviolet absorbers, and/or anti-agglomeration agents.

The additive (F) may be used alone or in combination, and may include but is not limited to fillers such as glass or aluminum; polymer compounds other than alkali-soluble resins (B) such as polyvinyl alcohol, polyethylene glycol monoalkyl ether or polyfluoroacrylate; vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tri(2-methoxyethoxy)silane, nitrogen-(2-amine 2-(3,4-epoxycyclohexyl)ethyl trimethoxysilane, 3-chloropropyl methyl dimethoxysilane, 3-chloropropyl trimethoxysilane, 3-(2-aminoethyl)-3-aminopropyl trimethoxysilane, 3-aminopropyl triethoxysilane, 3-(2-(3,4-epoxycyclohexyl)ethyl)trimethoxysilane, 3-chloropropyl methyl dimethoxysilane, 3-(2-aminoethyl)-3-aminopropyl trimethoxysilane, 3-(2-aminoethyl)-3-aminopropyl triethoxysilane, 3-(2-(3,4-epoxycyclohexyl)ethyl)trimethoxysilane, 3-chloropropyl methyl dimethoxysilane, 3- Adhesion promoters such as methacryloxypropyltrimethoxysilane or 3-thiolpropyltrimethoxysilane; antioxidants such as 2,2-thiobis(4-methyl-6-tert-butylphenol) and 2,6-di-tert-butylphenol; UV absorbers such as 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorophenylazide or alkoxybenzophenone; and/or anti-agglomeration agents such as sodium polyacrylate.

Based on the total usage of the alkali-soluble resin (B) being 100 parts by weight, the usage of the additive (F) is 0.1 to 10 parts by weight, preferably 0.3 to 7 parts by weight, and more preferably 0.5 to 4 parts by weight.

Method for manufacturing liquid crystal display device

The liquid crystal display device of the present invention is equipped with the color filter produced by the above method. Specific examples of the liquid crystal display device include color liquid crystal display devices, organic EL display devices, or electronic paper.

A color liquid crystal display device having a color filter produced by the method of the present invention can be, for example, constructed such that a driving substrate equipped with a thin film transistor (TFT) and another substrate equipped with the color filter of the present invention face each other through a liquid crystal layer. Alternatively, the color liquid crystal display device can also be constructed such that a substrate having the color filter of the present invention formed on the surface of a driving substrate equipped with a thin film transistor (TFT) and a substrate having an indium tin oxide (ITO) electrode face each other through a liquid crystal layer. The latter structure can further improve the aperture ratio, and has the advantage of obtaining a bright and high-precision liquid crystal display device.

The color liquid crystal display device has a backlight module. For example, the backlight module may be a combination of a fluorescent lamp such as a cold cathode fluorescent lamp (CCFL) and a diffusion plate. In addition, a backlight module using a white light emitting diode (LED) as a light source may also be used. For example, white LEDs include: a white LED that emits white light by mixing a red LED, a green LED, and a blue LED; a white LED that emits white light by mixing a blue LED, a red LED, and a green luminescent fluorescent body; a white LED that emits white light by mixing a blue LED, a red luminescent fluorescent body, and a green luminescent fluorescent body; a white LED that emits white light by mixing a blue LED and a YAG-based fluorescent body; a white LED that emits white light by mixing a blue LED, an orange luminescent fluorescent body, and a green luminescent fluorescent body; or a white LED that emits white light by mixing an ultraviolet LED, a red luminescent fluorescent body, a green luminescent fluorescent body, and a blue luminescent fluorescent body.

In a color liquid crystal display device having a color filter produced by the method of the present invention, a suitable liquid crystal module of a twisted nematic (TN) type, a super twisted nematic (STN) type, an in-plane switching (IPS) type, a vertical alignment (VA) type, or an optically compensated birefringence (OCB) type can be used.

The organic EL display element having the color filter produced by the method of the present invention can adopt an appropriate structure, for example, the structure disclosed in Japanese Laid-Open Patent Publication No. JP-11-307242.

The electronic paper having the color filter produced by the method of the present invention may adopt an appropriate structure, for example, the structure disclosed in Japanese Patent Publication No. JP 2007-41169.

The following embodiments are used to illustrate the application of the present invention, but they are not used to limit the present invention. Anyone skilled in the art can make various changes and modifications without departing from the spirit and scope of the present invention.

Preparation of alkali soluble resin (B)

Synthesis Example B-1

A stirrer, a thermometer, a condenser and a nitrogen inlet were installed on a four-necked conical flask, and nitrogen was introduced. Then, 100 parts by weight of propylene glycol methyl ether acetate (abbreviated as PGMEA) was added, and the temperature was raised to 100°C. Next, 10 parts by weight of methacrylic acid (MAA), 20 parts by weight of 3,4-epoxyhexylmethyl methacrylate (EC-MMA), 10 parts by weight of 2-methylglycidyl methacrylate (MGMA), 20 parts by weight of N-phenylmaleimide (N-PMI), 40 parts by weight of 2-hydroxyethyl methacrylate (HEMA), and 4.5 parts by weight of 2,2'-azobis-2-methylbutyronitrile (AMBN) were dissolved in 100 parts by weight of propylene glycol methyl ether acetate to obtain a mixed solution, and the mixed solution was dripped into the above-mentioned four-necked conical flask dropwise over 2 hours. After reacting at 100°C for 6.5 hours, the alkali-soluble resin (B-1) of Synthesis Example B-1 was obtained.

Synthesis Example B-2 to Synthesis Example B-6

Synthesis Examples B-2 to B-6 use the same preparation method as the preparation method of the alkali-soluble resin (B-1) of Synthesis Example B-1, except that the types and amounts of raw materials in the alkali-soluble resin and the reaction conditions are changed in Synthesis Examples B-2 to B-6. The formulas and reaction parameters are shown in Table 1, and are not described here.

Preparation of photosensitive resin composition

Embodiment 1

100 parts by weight of the alkali-soluble resin (B-1) obtained in the above-mentioned Synthesis Example B-1, 5 parts by weight of C.I. Pigment Red 254 (hereinafter referred to as A-1), 20 parts by weight of EO-modified trihydroxymethylpropyl trimethacrylate (hereinafter referred to as C-1) and 10 parts by weight of 2-methyl-1-(4-methylthiophenyl)-2-morpholino-1-propanone (hereinafter referred to as D-4-1) were added with 500 parts by weight of propylene glycol methyl ether acetate (hereinafter referred to as E-1), and the mixture was dissolved and mixed with a shaking stirrer to prepare the photosensitive resin composition of Example 1. The photosensitive resin composition was evaluated by the following evaluation method, and the results are shown in Table 2.

Examples 2 to 24 and Comparative Examples 1 to 3

Examples 2 to 24 and Comparative Examples 1 to 3 use the same preparation method as the photosensitive resin composition of Example 1. The difference is that Examples 2 to 24 and Comparative Examples 1 to 3 change the types and usage amounts of the raw materials in the photosensitive resin composition. The formulas and evaluation results are shown in Table 2, respectively, and are not described here. Comparative Example 3 uses the following evaluation method similar to that of Examples 1 to 24 and Comparative Examples 1 to 2 to evaluate the gradient angle, but Comparative Example 3 uses a high-pressure mercury lamp instead of an ultraviolet light-emitting diode as the light source of the exposure device.

Evaluation method

Gradient Angle

The photosensitive resin compositions prepared in Examples 1 to 24 and Comparative Examples 1 to 3 were coated on a 100 mm×100 mm glass substrate by spin coating. Then, the coating was dried under reduced pressure for about 30 seconds at a pressure of about 100 mmHg. Next, the glass substrate was pre-baked at 80°C for 2 minutes to form a pre-baked coating film with a film thickness of 2.5 μm. Afterwards, an ultraviolet light emitting diode that can emit single-peak ultraviolet light with a wavelength of 365 nm is used as the light source of the exposure device for the pre-baked coating of Examples 1 to 24 and Comparative Examples 1 to 2, and a high-pressure mercury lamp is used as the light source of the exposure device for the pre-baked coating of Comparative Example 3. After irradiating the pre-baked coating with an exposure amount of 100 mJ/ ^cm2 , the exposed pre-baked coating is immersed in a developer (0.04% potassium hydroxide) at 23°C for 60 seconds to remove the part of the pre-baked coating that is not irradiated with ultraviolet light. Then, after washing with pure water, post-baking treatment is performed in an oven at 235°C for 30 minutes to obtain a pixel pattern. The gradient angle (angle between the glass substrate and the pattern) of the pixel pattern of each embodiment and comparative example was observed using a scanning electron microscope (manufactured by Hitachi, model S-3000N), and evaluated according to the following criteria. The evaluation results are shown in Table 2. ◎: 55∘＜ gradient angle ≦70∘; ○: 45∘＜ gradient angle ≦55∘; △: 35∘＜ gradient angle ≦45∘; ╳: gradient angle ≦35∘, or gradient angle >70∘.

From the results in Table 2, it can be seen that if the illumination of the exposure process is not 50 mW/cm ² to 95 mW/cm ² , the pixel pattern obtained has a poor gradient angle. Secondly, when the photoinitiator (D) of the photosensitive resin composition includes at least one of the oxime ester compound (D-1) represented by formula (I), the oxime ester compound (D-2) represented by formula (II), or the oxime ester compound (D-3) represented by formula (III), the pixel pattern obtained has a better gradient angle.

It should be added that, although the present invention uses specific compounds, compositions, reaction conditions, processes, analysis methods or specific instruments as examples to illustrate the pixel pattern production method, color filter and its production method, and liquid crystal display device of the present invention, anyone with common knowledge in the technical field to which the present invention belongs can know that the present invention is not limited to these. Without departing from the spirit and scope of the present invention, the pixel pattern production method, color filter and its production method, and liquid crystal display device of the present invention can also use other compounds, compositions, reaction conditions, processes, analysis methods or instruments.

Although the present invention has been disclosed in the above embodiments, it is not intended to limit the present invention. Anyone with ordinary knowledge in the technical field to which the present invention belongs can make various changes and modifications without departing from the spirit and scope of the present invention. Therefore, the protection scope of the present invention shall be defined by the scope of the attached patent application.

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Claims (12)

A method for producing a pixel pattern comprises: using a photosensitive resin composition to form a coating on a substrate; and performing an exposure process on the coating, wherein the exposure process uses an ultraviolet light emitting diode to irradiate the coating, a peak wavelength of the ultraviolet light emitting diode is not less than 300nm, and an illumination of the exposure process is 50mW/ ^cm2 to 95mW/ ^cm2 ; and the photosensitive resin composition comprises: a pigment (A); an alkali-soluble resin (B), wherein the alkali-soluble resin (B) is obtained by reacting an ethylenically unsaturated monomer (B-1) having one or more carboxylic acids or carboxylic anhydrides, an ethylenically unsaturated monomer (B-2) having an epoxy group, and other copolymerizable ethylenically unsaturated monomers (B-3); a compound containing an ethylenically unsaturated group (C); a photoinitiator (D); and a solvent (E). The method for producing a pixel pattern as described in claim 1, wherein the illumination of the exposure process is 52 mW/cm ² to 88 mW/cm ² . The method for producing a pixel pattern as described in claim 1, wherein the photoinitiator (D) comprises an oxime ester compound (D-1) represented by the following formula (I):

In formula (I), _Y1 represents an organic group as shown in the following formula (I-1); _Y2 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; _Y3 represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms;

In formula (I-1), Y ₄ represents a monovalent organic group; X ₁ represents an oxygen atom, a sulfur atom or a carbonyl group; and a represents an integer from 0 to 5. The method for producing a pixel pattern as described in claim 1, wherein the photoinitiator (D) comprises an oxime ester compound (D-2) represented by the following formula (II):

In formula (II), _Z1 represents an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, and a tolyl group; _Z2 represents an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, or a substituted or unsubstituted phenyl group; and _Z3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted carbazolyl group. The method for producing a pixel pattern as described in claim 1, wherein the photoinitiator (D) comprises an oxime ester compound (D-3) represented by the following formula (III):

In formula (III), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, COR ₁₆ , or a group represented by the following formula (III'-1);

or R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ or R ₇ and R ₈ independently and collectively represent a group represented by the following formula (III'-2);

provided that at least one pair of _R1 and _R2 , _R2 and _R3 , _R3 and _R4 , _R5 and _R6 , _R6 and _R7 or _R7 and _R8 is a group as represented by formula (III'-2); _R9 , _R10 , _R11 and _R12 are independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, wherein the alkyl group having 1 to 20 carbon atoms is unsubstituted or substituted by one or more of the following groups: a halogen or a phenyl group; or _R9 , _R10 , _R11 and _R12 are independently an unsubstituted phenyl group or a phenyl group substituted by one or more of the following groups: an alkyl group having 1 to 6 carbon atoms or a halogen; _X2 is CO or a single bond; R _{R 13} represents an alkyl group having 1 to 20 carbon atoms, which is unsubstituted or substituted by one or more of the following groups: halogen, R ₁₇ , COOR ₁₇ or OR ₁₇ ; or R ₁₃ represents an alkyl group having 2 to 20 carbon atoms, which is doped with one or more O or CO, wherein the doped alkyl group having 2 to 20 carbon atoms is unsubstituted or substituted by one or more halogens; or R ₁₃ represents a phenyl group or a naphthyl group, each of which is unsubstituted or substituted by one or more of the following groups: an alkyl group having 1 to 20 carbon atoms or a halogenated alkyl group having 1 to 4 carbon atoms; R ₁₄ represents a hydrogen atom, an alkoxy group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms; R _{R 15} represents an aryl group having 6 to 20 carbon atoms, each of which is unsubstituted or substituted by one or more of the following groups: halogen, halogenated alkyl group having 1 to 4 carbon atoms, OR ₁₇ , alkyl group having 2 to 20 carbon atoms doped with one or more O; or each of which is substituted by an alkyl group having 1 to 20 carbon atoms, said alkyl group having 1 to 20 carbon atoms is unsubstituted or substituted by one or more of the following groups: halogen, COOR ₁₇ , phenyl or OR ₁₇ ; or R ₁₅ represents a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms; or R ₁₅ represents an alkyl group having 1 to 20 carbon atoms, which is unsubstituted or substituted by one or more of the following groups: halogen or cycloalkyl group having 3 to 8 carbon atoms; R _{R 16} represents an aryl group having 6 to 20 carbon atoms, each of which is unsubstituted or substituted by one or more of the following groups: halogen, halogenated alkyl group having 1 to 4 carbon atoms, OR ₁₇ ; or each of which is substituted by one or more alkyl groups having 1 to 20 carbon atoms, said alkyl group having 1 to 20 carbon atoms is unsubstituted or substituted by one or more of the following groups: halogen or OR ₁₇ ; R ₁₇ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, which is unsubstituted or substituted by one or more of the following groups: halogen or cycloalkyl group having 3 to 20 carbon atoms doped with one or more O; or R ₁₇ represents an alkyl group having 2 to 20 carbon atoms doped with one or more O; or R ₁₇ represents a phenyl group, each of which is unsubstituted or substituted by one or more of the following groups: halogen, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms; provided that at least one group represented by formula (III'-1) exists in the formula (III). The method for producing a pixel pattern as described in claim 1, wherein the total amount of the alkali-soluble resin (B) used is 100 parts by weight, the amount of the pigment (A) used is 5 parts by weight to 300 parts by weight, the amount of the compound containing ethylenically unsaturated groups (C) used is 20 parts by weight to 200 parts by weight, the amount of the photoinitiator (D) used is 10 parts by weight to 100 parts by weight, and the amount of the solvent (E) used is 500 parts by weight to 5000 parts by weight. The method for producing a pixel pattern as described in claim 3, wherein the total amount of the alkali-soluble resin (B) used is 100 parts by weight, and the amount of the oxime ester compound (D-1) used is 1 part by weight to 100 parts by weight. The method for producing a pixel pattern as described in claim 4, wherein the total amount of the alkali-soluble resin (B) used is 100 parts by weight, and the amount of the oxime ester compound (D-2) used is 1 part by weight to 100 parts by weight. The method for producing a pixel pattern as described in claim 5, wherein the total amount of the alkali-soluble resin (B) used is 100 parts by weight, and the amount of the oxime ester compound (D-3) used is 1 part by weight to 100 parts by weight. A method for manufacturing a color filter, using the manufacturing method described in any one of claims 1 to 9 to form a pixel pattern layer. A color filter is produced by the production method as described in claim 10. A liquid crystal display device comprising a color filter as described in claim 11.