Red coloring composition
A red colored composition with optimized orange, red, and yellow colorants enhances the thickness and brightness of color filters, overcoming the limitations of existing color filters.
Patent Information
- Application Number
- JP2021057898
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2021-03-30
- Publication Date
- 2025-09-09
- Estimated Expiration
- 2041-03-30
AI Technical Summary
Existing color filters face challenges in achieving thinness and brightness, particularly due to insufficient absorption strength of yellow colorants used for reproducing red colors, and poor brightness of quinophthalone-based colorants.
A red colored composition comprising specific ratios and types of orange, red, and yellow colorants, along with a resin, polymerizable compound, polymerization initiator, and solvent, optimized for absorbance characteristics to enhance filter thickness and brightness.
The composition enables the production of thinner color filters with improved brightness by optimizing the absorbance properties of the colorants, addressing the limitations of existing technologies.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to a red colored composition, a color filter, a display device, and a solid-state imaging device. [Background technology]
[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are produced from colored curable resin compositions. Known colorants used in colored curable resin compositions for forming color filters include CI Pigment Orange 43 (Patent Documents 1 to 3) and CI Pigment Orange 64 (Patent Documents 3 to 5). [Prior art documents] [Patent documents]
[0003] [Patent Document 1] Japanese Patent Application Publication No. 11-310714 [Patent Document 2] Japanese Patent Application Laid-Open No. 2003-183511 [Patent Document 3] Japanese Patent Application Publication No. 2016-212372 [Patent Document 4] Japanese Patent Application Laid-Open No. 2017-68159 [Patent Document 5] Japanese Patent Application Laid-Open No. 2012-173356 Summary of the Invention [Problem to be solved by the invention]
[0004] Recently, the trend in technology has been to make thin color filters. However, some yellow colorants, which are essential for reproducing red, have insufficient absorption strength and therefore require excessive amounts, making it difficult to achieve thin color filters. Furthermore, color filters containing quinophthalone-based colorants, such as CI Pigment Yellow 138, as colorants sometimes have poor brightness.
[0005] An object of the present invention is to provide a red colored composition that is useful for thinning color filters and improving their brightness. [Means for solving the problem]
[0006] That is, the gist of the present invention is as follows. [1] A composition comprising a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E), the colorant (A) comprises an orange colorant (A-1) satisfying the condition (X), a red colorant (A-2), and at least one yellow colorant (A-3) selected from the group consisting of a metal-containing azo dye, an isoindoline dye, and a coumarin dye; A red colored composition, wherein the content of the yellow colorant (A-3) is 250 parts by mass or less per 100 parts by mass of the orange colorant (A-1). [Condition (X)] A composition (X-1) containing only an orange colorant (A-1) as a colorant, in which the content of the orange colorant (A-1) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (X-1) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 480 nm is 0.40 or more, The absorbance at a wavelength of 530 nm is 0.55 or more, The absorbance at a wavelength of 580 nm is 0.20 or less. [2] The red colored composition according to [1], wherein the red colorant (A-2) satisfies the condition (Y). [Condition (Y)] A composition (Y) containing only a red colorant (A-2) as a colorant, in which the content of the red colorant (A-2) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (Y) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 440 nm is 0.30 or less, The absorbance at a wavelength of 480 nm is less than 0.50, The absorbance at a wavelength of 530 nm is 0.30 or more, The absorbance at a wavelength of 580 nm is 0.10 or more. [3] The red-colored composition according to [1] or [2], wherein the yellow colorant (A-3) satisfies condition (Z). [Condition (Z)] A composition (Z-1) containing only a yellow colorant (A-3) as a colorant, in which the content of the yellow colorant (A-3) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (Z-1) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 440 nm is 0.50 or more, The absorbance at a wavelength of 480 nm is 0.20 or more, The absorbance at a wavelength of 530 nm is 0.10 or less, The absorbance at a wavelength of 580 nm is 0.10 or less. [4] The red colored composition according to any one of [1] to [3], wherein the orange colorant (A-1) includes at least one selected from CI Pigment Orange 43 and CI Pigment Orange 64. [5] The red coloring composition according to any one of [1] to [4], wherein the red colorant (A-2) includes at least one selected from the group consisting of CI Pigment Red 177, CI Pigment Red 254, CI Pigment Red 269, CI Pigment Red 291, and CI Acid Red 52. [6] The red colored composition according to any one of [1] to [5], wherein the yellow colorant (A-3) includes at least one selected from the group consisting of CI Pigment Yellow 139, CI Pigment Yellow 150, and CI Pigment Yellow 185. [7] A color filter formed from the red colored composition according to any one of [1] to [6]. [8] A display device comprising the color filter according to [7]. [8] A solid-state imaging device comprising the color filter according to [7]. [Effects of the Invention]
[0007] According to the present invention, it is possible to provide a red colored composition that is useful for reducing the thickness and improving the brightness of color filters. DETAILED DESCRIPTION OF THE INVENTION
[0008] The red colored composition of the present invention contains a colorant (hereinafter may be referred to as colorant (A)), a resin (hereinafter may be referred to as resin (B)), a polymerizable compound (hereinafter may be referred to as polymerizable compound (C)), a polymerization initiator (hereinafter may be referred to as polymerization initiator (D)), and a solvent (hereinafter may be referred to as solvent (E)). The red colored composition of the present invention may contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as components can be used alone or in combination unless otherwise specified.
[0009] <Colorant (A)> The colorant (A) includes an orange colorant (A-1) that satisfies the condition (X), a red colorant (A-2), and at least one yellow colorant (A-3) selected from the group consisting of azo dyes, isoindoline dyes, and coumarin dyes containing metals.
[0010] <Orange colorant (A-1)> The orange colorant (A-1) is characterized in that it satisfies the condition (X). [Condition (X)] A composition (X-1) containing only an orange colorant (A-1) as a colorant, in which the content of the orange colorant (A-1) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (X-1) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 480 nm is 0.40 or more, The absorbance at a wavelength of 530 nm is 0.55 or more, The absorbance at a wavelength of 580 nm is 0.20 or less.
[0011] In condition (X), The absorbance at a wavelength of 440 nm is preferably 0.30 or more and 0.90 or less, more preferably 0.35 or more and 0.85 or less, and even more preferably 0.40 or more and 0.80 or less. The absorbance at a wavelength of 480 nm is preferably 0.41 or more and 0.95 or less, more preferably 0.50 or more and 0.90 or less, and even more preferably 0.60 or more and 0.85 or less. The absorbance at a wavelength of 530 nm is preferably 0.57 or more and 0.80 or less, more preferably 0.60 or more and 0.75 or less, and even more preferably 0.62 or more and 0.70 or less. The absorbance at a wavelength of 570 nm is preferably 0.01 or more and 0.25 or less, more preferably 0.05 or more and 0.20 or less, and even more preferably 0.10 or more and 0.18 or less. The absorbance at a wavelength of 580 nm is preferably 0.01 or more and 0.18 or less, more preferably 0.03 or more and 0.16 or less, and even more preferably 0.05 or more and 0.12 or less.
[0012] As the orange colorant (A-1) that satisfies the condition (X), a known dye or pigment can be used. The orange colorant (A-1) that satisfies the condition (X) preferably contains at least one selected from CI Pigment Orange 43 and CI Pigment Orange 64.
[0013] The content of the orange colorant (A-1) in the total amount of the colorant (A) is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 10% by mass or more, and even more preferably 15% by mass or more, and is preferably 70% by mass or less, more preferably 65% by mass or less, even more preferably 60% by mass or less, and even more preferably 50% by mass or less.
[0014] <Red colorant (A-2)> As the red colorant (A-2), known dyes and pigments that exhibit red color can be used. Among them, as the red colorant (A-2), a red colorant (A-2) that satisfies the condition (Y) is preferred. [Condition (Y)] A composition (Y) containing only a red colorant (A-2) as a colorant, in which the content of the red colorant (A-2) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (Y) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 440 nm is 0.30 or less, The absorbance at a wavelength of 480 nm is less than 0.50, The absorbance at a wavelength of 530 nm is 0.30 or more, The absorbance at a wavelength of 580 nm is 0.10 or more.
[0015] In condition (Y), The absorbance at a wavelength of 440 nm is preferably 0.01 or more and 0.30 or less, more preferably 0.03 or more and 0.30 or less, and even more preferably 0.05 or more and 0.29 or less. The absorbance at a wavelength of 480 nm is preferably 0.01 or more and 0.48 or less, more preferably 0.03 or more and 0.47 or less, and even more preferably 0.05 or more and 0.45 or less. The absorbance at a wavelength of 530 nm is preferably 0.31 or more and 0.60 or less, more preferably 0.33 or more and 0.55 or less, and even more preferably 0.35 or more and 0.50 or less. The absorbance at a wavelength of 570 nm is preferably 0.30 or more and 0.65 or less, more preferably 0.33 or more and 0.60 or less, and even more preferably 0.35 or more and 0.55 or less. The absorbance at a wavelength of 580 nm is preferably 0.11 or more and 0.50 or less, more preferably 0.11 or more and 0.45 or less, and even more preferably 0.11 or more and 0.40 or less.
[0016] The red colorant (A-2) satisfying the condition (Y) preferably contains at least one selected from the group consisting of CI Pigment Red 177, CI Pigment Red 254, CI Pigment Red 269, CI Pigment Red 291, and CI Acid Red 52, and more preferably contains at least one selected from the group consisting of CI Pigment Red 177 and CI Pigment Red 269.
[0017] The content of the red colorant (A-2) in the total amount of the colorant (A) is preferably 20% by mass or more, more preferably 25% by mass or more, even more preferably 30% by mass or more, and even more preferably 35% by mass or more, and is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 85% by mass or less.
[0018] The content of the red colorant (A-2) is preferably 1 to 10,000 parts by mass, more preferably 50 to 5,000 parts by mass, and even more preferably 100 to 2,500 parts by mass, relative to 100 parts by mass of the orange colorant (A-1).
[0019] <Yellow colorant (A-3)> The yellow colorant (A-3) may be at least one colorant selected from the group consisting of metal-containing azo dyes, isoindoline dyes, and coumarin dyes, and may be any known dye or pigment that exhibits a yellow color. Examples of metals contained in the azo dye include copper, nickel, cobalt, and zinc, with nickel being preferred. In the azo dye, the metal preferably forms a complex with the organic dye via a coordinate bond. The yellow colorant (A-3) is preferably a yellow colorant (A-3) that satisfies condition (Z). [Condition (Z)] A composition (Z-1) containing only a yellow colorant (A-3) as a colorant, in which the content of the yellow colorant (A-3) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (Z-1) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 440 nm is 0.50 or more, The absorbance at a wavelength of 480 nm is 0.20 or more, The absorbance at a wavelength of 530 nm is 0.10 or less, The absorbance at a wavelength of 580 nm is 0.10 or less.
[0020] In condition (Z), The absorbance at a wavelength of 440 nm is preferably 0.55 or more and 1.10 or less, more preferably 0.60 or more and 1.05 or less, and even more preferably 0.65 or more and 1.00 or less. The absorbance at a wavelength of 480 nm is preferably 0.22 or more and 0.70 or less, more preferably 0.25 or more and 0.65 or less, and even more preferably 0.30 or more and 0.60 or less. The absorbance at a wavelength of 530 nm is preferably 0.01 or more and 0.09 or less, more preferably 0.02 or more and 0.07 or less, and even more preferably 0.03 or more and 0.05 or less. The absorbance at a wavelength of 580 nm is preferably 0.01 or more and 0.09 or less, more preferably 0.02 or more and 0.07 or less.
[0021] The yellow colorant (A-3) that satisfies the condition (Z) is preferably a pigment, and more preferably contains at least one selected from the group consisting of CI Pigment Yellow 139, CI Pigment Yellow 150, and CI Pigment Yellow 185.
[0022] The content of the yellow colorant (A-3) in the total amount of the colorant (A) is preferably 1 mass% or more, more preferably 2 mass% or more, even more preferably 3 mass% or more, and still more preferably 4 mass% or more, and is preferably 45 mass% or less, more preferably 40 mass% or less, even more preferably 35 mass% or less, and still more preferably 30 mass% or less.
[0023] The content of the yellow colorant (A-3) is 250 parts by mass or less, preferably 200 parts by mass or less, more preferably 150 parts by mass or less, even more preferably 100 parts by mass or less, and preferably 10 parts by mass or more, more preferably 20 parts by mass or more, and even more preferably 25 parts by mass or more, relative to 100 parts by mass of the orange colorant (A-1).
[0024] In addition to the orange colorant (A-1), the red colorant (A-2), and the yellow colorant (A-3), the colorant (A) may contain a colorant different from the orange colorant (A-1), the red colorant (A-2), and the yellow colorant (A-3). The colorant different from the orange colorant (A-1), the red colorant (A-2), and the yellow colorant (A-3) may be either a dye (hereinafter, sometimes referred to as dye (A1)) or a pigment (hereinafter, sometimes referred to as pigment (A2)). The colorant different from the orange colorant (A-1), the red colorant (A-2), and the yellow colorant (A-3) may contain one or both of these dyes (A1) and pigments (A2).
[0025] The dye (A1) is not particularly limited, and any known dye can be used as long as it does not include the orange colorant (A-1), the red colorant (A-2), and the yellow colorant (A-3). Examples of the dye include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of the dye include compounds classified as non-pigment dyes with hues in the Color Index (published by The Society of Dyes and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In terms of chemical structure, examples include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.
[0026] in particular, CI Solvent Violet 11 (hereinafter, the term CI Solvent Violet will be omitted and only the numbers will be used), 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 1 23, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324, 335, 340; CI acid dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct dyes such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, and 60; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic dyes such as CI Basic Green 1; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; Examples include CI Vat dyes such as CI Vat Green 1. These dyes may be appropriately selected in accordance with the desired spectral spectrum of the color filter.
[0027] The pigment (A2) is not particularly limited and any known pigment can be used, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments include yellow pigments such as CI Pigment Yellow 83 and 138; Orange pigments such as CI Pigment Orange 36, 38, 62, 71, 72; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, and 58; Brown pigments such as CI Pigment Brown 23 and 25; Examples include black pigments such as CI Pigment Black 1 and 7.
[0028] The pigment may be subjected, as necessary, to a rosin treatment, a surface treatment using a pigment derivative into which an acidic group or a basic group has been introduced, a graft treatment onto the pigment surface using a polymer compound or the like, a microparticle treatment using a sulfuric acid microparticle method or the like, a washing treatment using an organic solvent or water to remove impurities, a treatment to remove ionic impurities using an ion exchange method or the like, or the like. The pigment preferably has a uniform particle size. By adding a pigment dispersant and carrying out a dispersion treatment, it is possible to obtain a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution.
[0029] Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant include trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Corporation), EFKA (manufactured by CIBA), AJISPER (manufactured by Ajinomoto Fine-Techno Co., Ltd.), and Disperbyk (manufactured by BYK-Chemie). When a pigment dispersant is used, the amount thereof is preferably from 1 to 100% by mass, more preferably from 5 to 50% by mass, based on the total amount of the pigment (A2). When the amount of the pigment dispersant used is within this range, a pigment dispersion in a uniformly dispersed state tends to be obtained.
[0030] The content of colorant (A) in the red colored composition is preferably 5% by mass or more and 70% by mass or less, more preferably 10% by mass or more and 65% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less, based on the total amount of solids. When the content of colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the resin (B) and the polymerizable compound (C) can be contained in the composition in the required amounts, a pattern with sufficient mechanical strength can be formed.
[0031] Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the red colored composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.
[0032] <Resin (B)> Resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having structural units derived from at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "monomer (a)"). Resin (B) is preferably a copolymer having a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b)"), and other structural units. Examples of other structural units include structural units derived from a monomer copolymerizable with monomer (a) (however, different from monomer (a) and monomer (b); hereinafter, this may be referred to as "monomer (c)"), structural units having an ethylenically unsaturated bond, etc.
[0033] In this specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.
[0034] Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like.
[0035] Among these, acrylic acid, methacrylic acid, o-, m-, p-vinylbenzoic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.
[0036] Monomer (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.
[0037] Examples of the monomer (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b2)"), and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b3)").
[0038] Examples of the monomer (b1) include a monomer having a structure in which a linear or branched unsaturated aliphatic hydrocarbon has been epoxidized (hereinafter, this may be referred to as "monomer (b1-1)") and a monomer having a structure in which an unsaturated alicyclic hydrocarbon has been epoxidized (hereinafter, this may be referred to as "monomer (b1-2)").
[0039] The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond. Examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl ether), Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.
[0040] Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., CELLOXIDE (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., CYCLOMER (registered trademark) M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).
[0041] [ka]
[0042] [In formula (BI) and formula (BII), R a and R b are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X a and X b are, independently of each other, a single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c represents -NH-. R c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]
[0043] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
[0044] Examples of alkyl groups in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.
[0045] R a and R b Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.
[0046] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.
[0047] X a and X b Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).
[0048] Examples of the compound represented by formula (BI) include compounds represented by any one of formulas (BI-1) to (BI-15). Among these, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9) and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9) and (BI-15) are more preferred.
[0049] [ka]
[0050] Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), and among these, preferred are compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15), and more preferred are compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15).
[0051] [ka]
[0052] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. The compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio thereof [compound represented by formula (BI) : compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20 on a molar basis.
[0053] As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferred. Examples of the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.
[0054] The monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Ltd.), tetrahydrofurfuryl methacrylate, and the like.
[0055] The monomer (b) is preferably the monomer (b1) in that it can further increase the reliability of the obtained color filter in terms of heat resistance, chemical resistance, etc. Furthermore, the monomer (b1-2) is more preferable in that it provides excellent storage stability of the colored composition.
[0056] Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0] 2,6 ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 ] decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-8-yl(meth)acrylate (commonly known in the art as "dicyclopentenyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters such as decene-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Halogen atom-containing (meth)acrylic acid esters such as 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene Bicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept bicyclounsaturated compounds such as 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples include vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these, styrene, vinyltoluene, tricyclo[5.2.1.0] and cyclopentyl methyl ether are preferred from the viewpoint of copolymerization reactivity and heat resistance. 2,6 ]Decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decene-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-9-yl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, phenyl(meth)acrylate, 2,2,3,3,4,4,5,5-octafluoropentyl(meth)acrylate, 9-vinylcarbazole, benzyl(meth)acrylate, 2-hydroxyethyl(meth)acrylate, and 2-ethylhexyl(meth)acrylate are preferred.
[0057] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] Decyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl (meth)acrylate / 9-vinylcarbazole / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / phenyl (meth)acrylate / o-vinyl benzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / phenyl (meth)acrylate / m-vinyl benzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / phenyl (meth)acrylate / p-vinyl benzoic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / phenyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate / 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] Decyl (meth)acrylate / (meth)acrylic acid / 2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / Tricyclo[5.2.1.0 2,6 ] decenyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, and resins described in JP-A Nos. 9-106071, 2004-29518, and 2004-361455. Among these, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b).
[0058] Resin (B) may be a combination of two or more kinds. In this case, resin (B) contains at least It is preferable that the composition contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b), more preferably, the copolymer contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1); It is more preferable that the copolymer contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2), 3,4-Epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6] It is even more preferable that the copolymer contains one or more selected from the group consisting of decyl (meth)acrylate / (meth)acrylic acid / 2-ethylhexyl (meth)acrylate copolymers.
[0059] The polystyrene-equivalent weight average molecular weight (Mw) of resin (B) is preferably from 1,000 to 100,000, more preferably from 2,000 to 50,000, even more preferably from 3,000 to 30,000, and still more preferably from 5,000 to 30,000. When the weight average molecular weight is within the above range, the solubility of the unexposed areas in a developer is high, and the resulting pattern tends to have high film retention and hardness.
[0060] The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1 or more and 6 or less, more preferably 1 or more and 5 or less, and even more preferably 1 or more and 4 or less.
[0061] The acid value (solid content equivalent) of resin (B) is preferably 10 mg-KOH / g to 300 mg-KOH / g, more preferably 20 mg-KOH / g to 250 mg-KOH / g, even more preferably 25 mg-KOH / g to 200 mg-KOH / g, still more preferably 30 mg-KOH / g to 180 mg-KOH / g, and particularly preferably 40 mg-KOH / g to 150 mg-KOH / g. The acid value is measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin, and can be determined, for example, by titration with an aqueous potassium hydroxide solution.
[0062] The content of the resin (B) is preferably 5 to 90% by mass, more preferably 10 to 80% by mass, even more preferably 13 to 70% by mass, and still more preferably 15 to 60% by mass, relative to 100% by mass of the solid content of the red colored composition. When the content of the resin (B) is within the above range, the solubility of the unexposed area in a developer tends to be high.
[0063] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.
[0064] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tri(meth)acrylate, tetra ... Examples of the acrylate copolymer include 2-(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. Of these, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferred.
[0065] The content of the polymerizable compound (C) is preferably 1 to 65 mass %, more preferably 5 to 60 mass %, and even more preferably 10 to 55 mass %, based on the total amount of solids. When the content of the polymerizable compound (C) is within the above range, the residual film rate during color pattern formation and the chemical resistance of the color filter tend to be improved.
[0066] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include O-acyloxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, and biimidazole compounds.
[0067] Examples of the O-acyloxime compound include O-acyloxime compounds having a diphenyl sulfide skeleton such as N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine; N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-one-2-imine; O-acyloxime compounds having a carbazole skeleton such as N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine; and O-acyloxime compounds having a fluorene skeleton such as 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluoren-2-yl]ethanone O-acetyloxime. Commercially available products such as Irgacure (registered trademark) OXE01 and OXE02 (all manufactured by BASF), PBG-327 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), N-1919 (manufactured by ADEKA Corporation), and DFI-091 (manufactured by Daito ChemiX Co., Ltd.) may also be used.Among them, the O-acyloxime compound is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, and 1-[7-(2-methylbenzoyl)-9,9-dipropyl-9H-fluoren-2-yl]ethanone O-acetyloxime. These O-acyloxime compounds tend to produce color filters with high brightness.
[0068] Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. Commercially available products such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF) may also be used.
[0069] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.
[0070] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.
[0071] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).
[0072] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.
[0073] Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate, and titanocene compounds.
[0074] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an O-acyloxime compound, an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.
[0075] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving productivity of the color filter.
[0076] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
[0077] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, among which 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.
[0078] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.
[0079] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
[0080] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.
[0081] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of the color filter tends to improve.
[0082] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the art can be used. Examples include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, or -COO-), aromatic hydrocarbon solvents, amide solvents, and dimethyl sulfoxide.
[0083] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.
[0084] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.
[0085] Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, methyl 2-ethoxy ... Examples of the alkyl ether acetate include ethyl 2-methoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.
[0086] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
[0087] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
[0088] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.
[0089] Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
[0090] Among the above solvents, from the viewpoints of coatability and drying property, organic solvents having a boiling point at 1 atm of 120° C. or higher and 180° C. or lower are preferred. Preferred solvents are propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, and more preferred are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate, and ethyl 3-ethoxypropionate.
[0091] The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the red colored composition of the present invention. In other words, the total content of the solids in the red colored composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness during coating is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.
[0092] <Leveling Agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants containing fluorine atoms, which may have a polymerizable group in the side chain. Examples of silicone surfactants include surfactants having a siloxane bond in the molecule, such as Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (manufactured by Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan, LLC).
[0093] Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule, such as Fluorad (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, and RS-718-K (manufactured by DIC Corporation), Ftop (registered trademark) EF301, EF303, EF351, and EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, and SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Research Institute, Inc.).
[0094] Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).
[0095] The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, more preferably 0.002% by mass or more and 0.2% by mass or less, and even more preferably 0.005% by mass or more and 0.2% by mass or less, based on the total amount of the red colored composition. Note that this content does not include the content of the dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
[0096] <Other ingredients> The red colored composition of the present invention may contain additives known in the technical field, such as a polymerization initiator aid, a filler, another polymer compound, an adhesion promoter, a light stabilizer, and a chain transfer agent, as needed. Adhesion promoters include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-sulfur Examples thereof include phenylpropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N-phenyl-3-aminopropyltriethoxysilane.
[0097] <Method of producing red colored composition> The red colored composition can be prepared, for example, by mixing the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), the solvent (E), and, if necessary, the leveling agent (F), the polymerization initiation aid (D1), and other components. The colorant (A) may be contained in advance in a pigment dispersion liquid, and the remaining components are mixed with the pigment dispersion liquid to give a predetermined concentration, thereby preparing the desired red-colored composition. When a dye is contained, the dye may be dissolved in advance in part or all of the solvent (E) to prepare a solution, which is preferably filtered through a filter having a pore size of about 0.01 to 1 μm. The red colored composition after mixing is preferably filtered through a filter with a pore size of about 0.01 to 10 μm.
[0098] <Color filter> Methods for producing a colored pattern of a color filter from the red colored composition of the present invention include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography is a method in which the red colored composition is applied to a substrate, dried to form a composition layer, and then exposed to light through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.
[0099] The film thickness of the color filter (cured film) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, even more preferably 3 μm or less, still more preferably 1.5 μm or less, particularly preferably 0.5 μm or less, and preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.
[0100] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or silica-coated soda lime glass; a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate; silicon; or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. A separate color filter layer, a resin layer, a transistor, a circuit, or the like may be formed on these substrates. Alternatively, a silicon substrate treated with HMDS may be used.
[0101] Formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be produced as follows. First, a red coloring composition is applied to a substrate, and volatile components such as the solvent are removed by heat drying (pre-baking) and / or vacuum drying to obtain a smooth composition layer. Examples of application methods include spin coating, slit coating, and slit and spin coating. The temperature for heat drying is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When vacuum drying is carried out, it is preferably carried out under a pressure of 50 to 150 Pa at a temperature of 20 to 25°C. The film thickness of the composition layer is not particularly limited and may be appropriately selected depending on the film thickness of the desired color filter.
[0102] Next, the composition layer is exposed through a photomask to form a desired color pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate for the intended application is used. The light source used for exposure is preferably a light source that emits light with a wavelength of 250 to 450 nm. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, 408 nm, and 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduction projection exposure device or proximity exposure device such as a mask aligner or stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask and substrate.
[0103] A colored pattern is formed on the substrate by bringing the exposed composition layer into contact with a developer and developing it. The unexposed portions of the composition layer are dissolved and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may also contain a surfactant. The development method may be any of a puddle method, a dipping method, a spray method, or the like. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.
[0104] Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature is preferably 80 to 250° C., more preferably 100 to 245° C. The post-bake time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.
[0105] The colored patterns and colored coating films thus obtained are useful as color filters, and the color filters are useful as color filters used in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc. [Example]
[0106] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the examples, % and parts representing the content or amount used are by mass unless otherwise specified.
[0107] [Resin synthesis example 1] A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was filled with an appropriate amount of nitrogen to create a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was added, followed by heating to 80°C with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0] 2,6]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A solution of 289 parts of a mixture of decan-9-yl acrylate (1:1 content) dissolved in 125 parts of propylene glycol monomethyl ether acetate was added dropwise using a dropping pump over approximately 5 hours. Meanwhile, a solution of 33 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise to the flask over approximately 6 hours using another dropping pump. After the addition was completed, the mixture was maintained at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (Resin (B-1)) with a solids content of 35.1%. The resulting copolymer had a weight-average molecular weight (Mw) of 9200, a polydispersity of 2.08, and an acid value calculated as solids of 77 mg-KOH / g. Resin (B-1) has the following structural units:
[0108] [ka]
[0109] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Apparatus: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40°C Solvent: THF Flow rate: 1.0mL / min Test liquid solid content concentration: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standard material ;TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (Manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.
[0110] [Preparation of Dispersion 1] 10.0 parts of CI Pigment Orange 43 (pigment), 7.8 parts (solids equivalent) of a dispersant (BYK BYKLPN-6919; a propylene glycol monomethyl ether acetate solution with a solids content of 60%), 7.8 parts (solids equivalent) of resin (B-1), and 22.2 parts of 4-hydroxy-4-methyl-2-pentanone were mixed, and 154.8 parts of propylene glycol monomethyl ether acetate was added. 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain Dispersion 1.
[0111] [Preparation of Dispersions 2 to 10] Dispersions 2 to 10 were obtained in the same manner as Dispersion 1, except that the compositions were changed as shown in Table 1. In Table 2, each component represents the following compound. PO43: CI Pigment Orange 43; Orange colorant (A-1) PO64: CI Pigment Orange 64; Orange colorant (A-1) PR254: CI Pigment Red 254; Red colorant (A-2) PR291: CI Pigment Red 291; Red colorant (A-2) PR177: CI Pigment Red 177; Red colorant (A-2) PR269: CI Pigment Red 269; Red colorant (A-2) PY138: CI Pigment Yellow 138 (quinophthalone pigment); yellow colorant PY150: CI Pigment Yellow 150 (nickel complex azo pigment); yellow colorant (A-3) PY185: CI Pigment Yellow 185 (isoindoline pigment); yellow colorant (A-3) PY139: CI Pigment Yellow 139 (isoindoline pigment); yellow colorant (A-3) Solvent (E-1): 4-hydroxy-4-methyl-2-pentanone Solvent (E-2): Propylene glycol monomethyl ether acetate Solvent (E-3): Propylene glycol monomethyl ether
[0112] [Table 1]
[0113] [Preparation of Compositions X-1 to X-2, Compositions Y-1 to Y-4, and Compositions Z-1 to Z-4] The components shown in Table 2 were mixed to obtain compositions X-1 to X-2, compositions Y-1 to Y-4, and compositions Z-1 to Z-4. In Table 2, each component represents the following compound. Resin (B-1): Resin (B-1) (solid content conversion) Polymerizable compound (C-1): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine (PBG-327; oxime compound; Changzhou Strong Electronic New Materials Co., Ltd.) Solvent (E-2): Propylene glycol monomethyl ether acetate Leveling agent (F-1): Polyether-modified silicone oil (solid content equivalent) (Toray Silicone SH8400; manufactured by Dow Corning Toray Co., Ltd.)
[0114] [Examples 1 to 11, Comparative Examples 1 to 10] The components shown in Tables 3 and 4 were mixed to obtain a red colored composition.
[0115] <Production of color filters (colored coating films)> [Compositions X-1 to X-2, Compositions Y-1 to Y-4, Compositions Z-1 to Z-4] Compositions X-1 to X-2, Compositions Y-1 to Y-4, and Compositions Z-1 to Z-4 were applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated) at a rotation speed adjusted to give a film thickness of 1 μm after post-baking, and then pre-baked at 100°C for 3 minutes to form a colored resin composition layer. After cooling, the layers were exposed to 60 mJ / cm 2 in an air atmosphere using an exposure machine (TME-150RSK; Topcon Corporation). 2 After that, post-baking was carried out in an oven at 230° C. for 20 minutes to obtain a color filter. [Red colored composition] A red colored composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated). In this spin coating, the rotation speed was adjusted so that the film thickness after post-baking would exhibit the specified chromaticity. Next, the film was pre-baked at 100°C for 3 minutes to form a colored resin composition layer. After cooling, the film was exposed to 60 mJ / cm 2 in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). 2 After that, post-baking was carried out in an oven at 230° C. for 20 minutes to obtain a color filter.
[0116] <Absorbance measurement test> The color filter obtained by the method for producing a color filter was subjected to spectral measurement using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation). [Compositions X-1 to X-2, Compositions Y-1 to Y-4, Compositions Z-1 to Z-4] For the color filters obtained from compositions X-1 to X-2, compositions Y-1 to Y-4, and compositions Z-1 to Z-4, the absorbance of the colored coating film at wavelengths of 440, 480, 530, 570, and 580 nm was calculated by converting the obtained transmission spectra into absorbance using the following formula (1). A=-log 10 T...(1) (In formula (1), A represents absorbance and T represents transmittance.) [Red colored composition] For the color filter obtained from the red colored composition, the chromaticity was calculated from the obtained transmission spectrum.
[0117] <Film thickness measurement> The thickness of the resulting colored coating film was measured using a film thickness measuring device (DEKTAK3, manufactured by Nippon Shinku Gijutsu Co., Ltd.).
[0118] <Brightness measurement test> The color filter obtained by the method for producing a color filter was subjected to spectral measurement using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation). Using the obtained transmission spectrum, chromaticity and luminance were calculated from the wavelength when light from a C light source was transmitted.
[0119] [Table 2]
[0120] [Table 3]
[0121] [Table 4]
Claims
1. The composition comprises a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E), the colorant (A) comprises an orange colorant (A-1) that satisfies the condition (X), a red colorant (A-2) that satisfies the condition (Y), and a yellow colorant (A-3) that is at least one selected from the group consisting of azo dyes, isoindoline dyes, and coumarin dyes that contain a metal and that satisfies the condition (Z) (excluding colorants that contain at least C.I. Pigment Orange 64, C.I. Pigment Red 254, and C.I. Pigment Yellow 139); A red-colored composition in which the content of the yellow colorant (A-3) is 100 parts by mass or less per 100 parts by mass of the orange colorant (A-1). [Condition (X)] A composition (X-1) containing only an orange colorant (A-1) as a colorant, in which the content of the orange colorant (A-1) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (X-1) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 480 nm is 0.40 or more, The absorbance at a wavelength of 530 nm is 0.55 or more, The absorbance at a wavelength of 580 nm is 0.20 or less. [Condition (Y)] A composition (Y) containing only a red colorant (A-2) as a colorant, in which the content of the red colorant (A-2) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (Y) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 440 nm is 0.30 or less, The absorbance at a wavelength of 480 nm is less than 0.50, The absorbance at a wavelength of 530 nm is 0.30 or more, The absorbance at a wavelength of 580 nm is 0.10 or more. [Condition (Z)] A composition (Z-1) containing only the yellow colorant (A-3) as a colorant, in which the content of the yellow colorant (A-3) in the solid content was 10 mass %, was prepared, and the absorbance of a color filter formed from the composition (Z-1) and having a film thickness of 1 μm was measured. The absorbance at a wavelength of 440 nm is 0.50 or more, The absorbance at a wavelength of 480 nm is 0.20 or more, The absorbance at a wavelength of 530 nm is 0.10 or less, The absorbance at a wavelength of 580 nm is 0.10 or less.
2. The red colored composition according to claim 1, wherein the orange colorant (A-1) contains at least one selected from C.I. Pigment Orange 43 and C.I. Pigment Orange 64.
3. The red colorant (A-2) is C.I. Pigment Red 177, C.I. Pigment Red 254, C.I. Pigment Red 269, C.I. Pigment Red 291, and C.I. Acid Red 52. The red colored composition according to claim 1 or 2, comprising at least one selected from the group consisting of C.I. Pigment Red 177, C.I. Pigment Red 254, C.I. Pigment Red 269, C.I. Pigment Red 291, and C.I. Acid Red 52.
4. The yellow colorant (A-3) includes at least one selected from the group consisting of C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, and C.I. Pigment Yellow 185. The red-colored composition according to any one of claims 1 to 3.
5. A color filter formed from the red colored composition according to any one of claims 1 to 4.
6. A display device comprising the color filter according to claim 5 .
7. A solid-state imaging device comprising the color filter according to claim 5 .
Citation Information
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