Coloring composition, film, optical filter, solid-state imaging device, and image display device
The use of a coloring composition with high azomethine metal complex content in optical filters addresses the issue of colorant movement, providing enhanced long-term reliability and stability in high-temperature and high-humidity environments.
Patent Information
- Application Number
- JP2024022239
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-02-05
- Filing Date
- 2024-02-16
- Publication Date
- 2025-08-01
- Estimated Expiration
- 2041-02-01
AI Technical Summary
Conventional coloring compositions for optical filters, such as color filters, fail to provide sufficient long-term reliability due to colorant movement in high-temperature and high-humidity environments, affecting the integrity and performance of the films.
A coloring composition containing a yellow colorant with 30% by mass or more of azomethine metal complexes, such as azomethine copper and azomethine zinc complexes, along with specific resin and solvent formulations, which suppress colorant movement and enhance film stability.
The composition forms films with excellent long-term reliability, maintaining structural integrity even in harsh environmental conditions, ensuring consistent performance of optical filters and imaging devices.
Smart Images

Figure 0007717204000001 
Figure 0007717204000002 
Figure 0007717204000003
Abstract
Description
Technical Field
[0001] The present invention relates to a coloring composition containing a yellow colorant. The present invention also relates to a film, an optical filter, a solid-state imaging device, and an image display device using the coloring composition.
Background Art
[0002] In recent years, due to the widespread use of digital cameras, camera-equipped mobile phones, etc., the demand for solid-state imaging devices such as charge-coupled device (CCD) image sensors has been growing significantly. A color filter is used as a key device for displays and optical elements. A color filter usually has pixels of three primary colors, red, green, and blue, and plays a role in decomposing transmitted light into the three primary colors.
[0003] The colored pixels of each color of the color filter are manufactured using a coloring composition containing a colorant. Patent Document 1 describes an invention related to a coloring composition for a color filter composed of at least a pigment, a polymer, and a solvent, in which the content of the yellow pigment in the pigment component is 30% by weight or more, the yellow pigment is one or more selected from quinophthalone pigments, isoindoline pigments, isoindolinone pigments, nickel azo complex pigments, and methine·azomethine pigments, and the specific surface area of the yellow pigment is 70 m 2 / g or more.
Prior Art Documents
Patent Documents
[0004]
Patent Document 1
Summary of the Invention
Problems to be Solved by the Invention
[0005] In recent years, for devices equipped with optical filters such as color filters, the requirements for long-term reliability have been increasing. For this reason, the films used for optical filters are also required to be excellent in long-term reliability.
[0006] On the other hand, when a pixel is formed using a coloring composition containing a colorant and such an optical filter containing such pixels is exposed to a high-temperature and high-humidity environment for a long time, components such as the colorant contained in the pixel may move to a member (such as pixels of other colors) adjacent to the pixel. For this reason, the long-term reliability of the film obtained with conventionally known coloring compositions has not been sufficient, and there has been room for improvement.
[0007] Further, according to the study by the present inventor, it has been found that the long-term reliability of the film obtained using the coloring composition described in the example of Patent Document 1 is not sufficient and there is room for improvement.
[0008] Therefore, an object of the present invention is to provide a coloring composition capable of forming a film excellent in long-term reliability. Further, it is to provide a film, an optical filter, a solid-state imaging device, and an image display device using the coloring composition.
Means for Solving the Problems
[0009] According to the study by the present inventor, it has been found that the above object can be achieved with the coloring composition described below, and the present invention has been completed. Therefore, the present invention provides the following. <1> A coloring composition containing a colorant containing a yellow colorant, a resin, and a solvent, wherein the content of the yellow colorant in the colorant is 30% by mass or more, and the yellow colorant contains 15% by mass or more of an azomethine metal complex, the coloring composition. <2> The coloring composition according to <1>, wherein the content of the quinophthalone compound in the yellow colorant is less than 50% by mass. <3> The azomethine metal complex-containing coloring composition according to <1> or <2> contains at least one selected from an azomethine copper complex and an azomethine zinc complex. <4> The coloring composition according to any one of <1> to <3> contains at least one selected from a green coloring agent and a red coloring agent. <5> The coloring composition according to any one of <1> to <4> contains a green coloring agent, and the green coloring agent contains a phthalocyanine compound. <6> When a film with a thickness of 0.65 μm is formed using the coloring composition, the wavelength at which the light transmittance of the film becomes 50% is in the wavelength range of 470 to 520 nm. The coloring composition according to any one of <1> to <5>. <7> Further, the coloring composition according to any one of <1> to <6> contains a polymerizable compound and a photopolymerization initiator. <8> The coloring composition according to any one of <1> to <7> is for a color filter or an infrared transmission filter. <9> A film obtained from the coloring composition according to any one of <1> to <8>. <10> An optical filter having the film according to <9>. <11> A solid-state imaging device having the film according to <9>. <12> An image display device having the film according to <9>.
Advantages of the Invention
[0010] According to the present invention, a coloring composition capable of forming a film with excellent long-term reliability can be provided. Further, a film, an optical filter, a solid-state imaging device, and an image display device using the coloring composition can be provided.
Embodiments for Carrying Out the Invention
[0011] Hereinafter, the content of the present invention will be described in detail. In this specification, "~" is used to mean including the numerical values described before and after as the lower limit value and the upper limit value. In the notation of groups (atomic groups) in this specification, notations that do not indicate substitution or non-substitution include both groups (atomic groups) having no substituents and groups (atomic groups) having substituents. For example, the term "alkyl group" includes not only an alkyl group having no substituents (unsubstituted alkyl group) but also an alkyl group having substituents (substituted alkyl group). In this specification, "exposure" includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified. Examples of the light used for exposure include actinic rays or radiation such as the emission line spectrum of a mercury lamp, far ultraviolet rays typified by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams. In this specification, "(meth)acrylate" represents both acrylate and methacrylate, or either one; "(meth)acrylic" represents both acrylic and methacrylic, or either one; and "(meth)acryloyl" represents both acryloyl and methacryloyl, or either one. In this specification, Me in a structural formula represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group. In this specification, the weight average molecular weight and the number average molecular weight are values in terms of polystyrene measured by the GPC (gel permeation chromatography) method. In this specification, the total solid content refers to the total mass of the components obtained by removing the solvent from all the components of the composition. In this specification, a pigment means a compound that is hardly soluble in a solvent. In this specification, the term "step" includes not only an independent step but also a step that is included in this term if the intended action of the step is achieved even when it cannot be clearly distinguished from other steps.
[0012] <Coloring composition> The coloring composition of the present invention is a coloring composition containing a colorant containing a yellow colorant, a resin, and a solvent, wherein the content of the yellow colorant in the colorant is 30% by mass or more, The yellow colorant is characterized by containing 15% by mass or more of an azomethine metal complex.
[0013] Even when the film obtained using the coloring composition of the present invention is exposed to a high-temperature and high-humidity environment for a long period of time, it is possible to suppress the movement of the colorant contained in the film to adjacent pixels and the like, and it has excellent long-term reliability. Although the detailed reason for obtaining such an effect is unknown, it is presumed that a film with a high film density can be formed by using a colorant in which the content of the yellow colorant is 30% by mass or more and the azomethine metal complex is contained as the yellow colorant at 15% by mass or more. As a result, even when the film is exposed to a high-temperature and high-humidity environment, it is presumed that expansion of the film and the like can be suppressed. In addition, the azomethine metal complex easily interacts with other colorants and components other than the colorant contained in the film, and it is presumed that the movement of the colorant and the like can be suppressed by the strong interaction between the azomethine metal complex and the components in the film. For such reasons, it is presumed that the coloring composition of the present invention was able to form a film with excellent long-term reliability.
[0014] The coloring composition of the present invention is preferably used as a coloring composition for a color filter or an infrared transmission filter. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter or a coloring composition for forming an infrared transmission filter, and is more preferably used as a coloring composition for forming pixels of a color filter.
[0015] When a film with a thickness of 0.65 μm is formed using the coloring composition of the present invention, it is preferable that the wavelength at which the light transmittance of the film becomes 50% exists in the wavelength range of 470 to 520 nm, more preferably in the wavelength range of 475 to 520 nm, and even more preferably in the wavelength range of 480 to 520 nm. Among them, it is preferable that the wavelength at which the light transmittance becomes 50% exists in each of the wavelength ranges of 470 to 520 nm and 575 to 625 nm. In this aspect, the wavelength on the short-wavelength side at which the light transmittance becomes 50% preferably exists in the wavelength range of 475 to 520 nm, and more preferably in the wavelength range of 480 to 520 nm. Also, the wavelength on the long-wavelength side at which the light transmittance becomes 50% preferably exists in the wavelength range of 580 to 620 nm, and more preferably in the wavelength range of 585 to 615 nm. The coloring composition capable of forming a film having such spectral characteristics is preferably used as a coloring composition for forming a green pixel of a color filter.
[0016] Hereinafter, each component used in the coloring composition of the present invention will be described.
[0017] <<Colorant>> The coloring composition of the present invention contains a colorant containing a yellow colorant. As the yellow colorant, those containing an azomethine metal complex are used.
[0018] The azomethine metal complex used in the yellow colorant is preferably a pigment because it is easy to form a film with better long-term reliability. That is, the azomethine metal complex used in the yellow colorant is preferably an azomethine metal complex yellow pigment. Also, the azomethine metal complex preferably contains at least one selected from azomethine copper complexes and azomethine zinc complexes because it is easy to form a film with better long-term reliability, and more preferably contains an azomethine copper complex. The azomethine metal complex may be only one kind, or two or more kinds may be used in combination. Also, when two or more kinds of azomethine metal complexes are used in combination, two or more kinds of azomethine metal complexes may form a mixed crystal (solid solution) with each other.
[0019] Examples of azomethine copper complexes include C.I. Pigment Yellow 117, 129, etc. C.I. Pigment Yellow 117 is a compound represented by the following formula (ACu-2), and C.I. Pigment Yellow 129 is a compound represented by the following formula (ACu-1).
Chemical formula
[0020] Examples of azomethine zinc complexes include the compound represented by formula (AZn-1), the compound represented by formula (AZn-2), etc.
Chemical formula
[0021] X 1 and X 2 Examples of the halogen atom represented by are a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, preferably a chlorine atom or a bromine atom, more preferably a chlorine atom. X 1 and X 2Examples of the alkoxy group represented by [the formula] include methoxy group, ethoxy group, propyloxy group, i-propyloxy group, butyloxy group, i-butyloxy group, s-butyloxy group, t-butyloxy group, pentyloxy group, 1-methylbutyloxy group, 2-methylbutyloxy group, 3-methylbutyloxy group, 1,1-dimethylpropyloxy group, 1,2-dimethylpropyloxy group, 2,2-dimethylpropyloxy group, 1-ethylpropyloxy group, hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy group, 3-methylpentyloxy group, 4-methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2-dimethylbutyloxy group, 1,3-dimethylbutyloxy group, 2,2-dimethylbutyloxy group, 2,3-dimethylbutyloxy group, 3,3-dimethylbutyloxy group, 1-ethylbutyloxy group, 2-ethylbutyloxy group, 1,1,2-trimethylpropyloxy group, 1,2,2-trimethylpropyloxy group, 1-ethyl-1-methylpropyloxy group, 1-ethyl-2-methylpropyloxy group, and the like. Among them, alkoxy groups having 1 to 8 carbon atoms are cited as preferred examples.
[0022] Specific examples of the compound represented by formula (AZn-2) include compounds having the structures shown below.
Chemical formula
[0023] In addition, as the azomethine metal complex, it is also preferable to use a mixture or mixed crystal (solid solution) of the compound represented by formula (ACu-1) and the compound represented by formula (AZn-1). According to this embodiment, the color value is high and the light shielding performance at the same content can be enhanced. As the above mixture or mixed crystal (solid solution), it is preferably contained 10 to 900 parts by mass of the compound represented by formula (AZn-1) with respect to 100 parts by mass of the compound represented by formula (ACu-1), and more preferably contained 25 to 400 parts by mass.
[0024] The colorant used in the coloring composition of the present invention may further contain a yellow colorant other than the azomethine metal complex. By further containing a yellow colorant other than the azomethine metal complex, an optical filter having more excellent spectral characteristics can be obtained.
[0025] Examples of the yellow colorant other than the azomethine metal complex include azo compounds, isoindoline compounds, pteridine compounds, and quinophthalone compounds. For the reason that a film excellent in spectral characteristics and light resistance is easily obtained, azo compounds, isoindoline compounds, and pteridine compounds are preferable, and azo compounds and isoindoline compounds are more preferable. Further, the azo compound used as the yellow colorant is preferably an azo metal complex for the reason that a film excellent in spectral characteristics and light resistance is easily obtained.
[0026]
[0027] Specific examples of the yellow colorant other than the azomethine metal complex include yellow pigments such as C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 118, 119, 120, 123, 125, 126, 127, 128, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214, 215, 228, 231, 232 (methine-based), 233 (quinoline-based), 234 (aminoketone-based), 235 (aminoketone-based), 236 (aminoketone-based).In addition, as yellow colorants other than azomethine metal complexes, the compounds described in JP-A-2017-201003, the compounds described in JP-A-2017-197719, the compounds described in paragraphs 0011 to 0062 and 0137 to 0276 of JP-A-2017-171912, the compounds described in paragraphs 0010 to 0062 and 0138 to 0295 of JP-A-2017-171913, the compounds described in paragraphs 0011 to 0062 and 0139 to 0190 of JP-A-2017-171914, the compounds described in paragraphs 0010 to 0065 and 0142 to 0222 of JP-A-2017-171915, the quinophthalone compounds described in paragraphs 0011 to 0034 of JP-A-2013-054339, the quinophthalone compounds described in paragraphs 0013 to 0058 of JP-A-2014-026228, the isoindoline compounds described in JP-A-2018-062644, the quinophthalone compounds described in JP-A-2018-203798, the quinophthalone compounds described in JP-A-2018-062578, the quinophthalone compounds described in Patent No. 6432076, the quinophthalone compounds described in JP-A-2018-155881, the quinophthalone compounds described in JP-A-2018-111757, the quinophthalone compounds described in JP-A-2018-040835, the quinophthalone compounds described in JP-A-2017-197640, the quinophthalone compounds described in JP-A-2016-145282, the quinophthalone compounds described in JP-A-2014-085565, the quinophthalone compounds described in JP-A-2014-021139, the quinophthalone compounds described in JP-A-2013-209614, the quinophthalone compounds described in JP-A-2013-209435, the quinophthalone compounds described in JP-A-2013-181015, the quinophthalone compounds described in JP-A-2013-061622, the quinophthalone compounds described in JP-A-2013-032486, the quinophthalone compounds described in JP-A-2012-226110, the quinophthalone compounds described in JP-A-2008-074987, the quinophthalone compounds described in JP-A-2008-081565, the quinophthalone compounds described in JP-A-2008-074986, the quinophthalone compounds described in JP-A-2008-074985,The quinophthalone compounds described in JP-A-2008-050420, the quinophthalone compounds described in JP-A-2008-031281, the quinophthalone compounds described in JP-B-48-032765, the quinophthalone compounds described in JP-A-2019-008014, the quinophthalone compounds described in Patent No. 6607427, the methine dyes described in JP-A-2019-073695, the methine dyes described in JP-A-2019-073696, the methine dyes described in JP-A-2019-073697, and the methine dyes described in JP-A-2019-073698 can also be used. Further, those obtained by multimerizing these compounds are also preferably used from the viewpoint of improving the color value.,
[0028] As yellow colorants other than azomethine metal complexes, C.I. Pigment Yellow 129, 139, 150, 185 are preferable, and C.I. Pigment Yellow 150 is more preferable.
[0029] The colorant contained in the coloring composition of the present invention may further contain colorants of other hues than the yellow colorant. Examples of colorants of other hues to be used in combination include chromatic colorants such as green colorants, red colorants, purple colorants, blue colorants, orange colorants, and black colorants. As the colorant of other hues, it is preferably at least one selected from green colorants, red colorants, and orange colorants, and more preferably at least one selected from green colorants and red colorants. The other colorant may be a pigment or a dye, but a pigment is preferable. When a pigment is used as the other colorant, the interaction between the pigment as the other colorant and the azomethine metal complex as the yellow colorant can more effectively suppress the movement of the colorant contained in the film to adjacent pixels and the like, and a film having more excellent long-term reliability can be formed. Such an effect is remarkable when a green pigment is used as the other colorant, and among them, the most remarkable effect is achieved when a phthalocyanine compound is used as the green pigment.
[0030] Examples of the red colorant include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, thioindigo compounds, etc. For the reason that it is easy to form a film with more excellent long-term reliability, diketopyrrolopyrrole compounds, anthraquinone compounds, and azo compounds are preferred, and diketopyrrolopyrrole compounds are more preferred. Further, the red colorant is preferably a pigment.
[0031] Specific examples of the red colorant include C.I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, 297 and other red pigments. Further, as the red colorant, a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, a diketopyrrolopyrrole compound described in paragraph numbers 0016 to 0022 of Patent No. 6248838, a diketopyrrolopyrrole compound described in International Publication No. 2012 / 102399, a diketopyrrolopyrrole compound described in International Publication No. 2012 / 117965, a naphthol azo compound described in JP-A-2012-229344, a red colorant described in Patent No. 6516119, a red colorant described in Patent No. 6525101, etc. can also be used. Further, as the red colorant, a compound having a structure in which an aromatic ring group having a group to which an oxygen atom, a sulfur atom or a nitrogen atom is bonded introduced to the aromatic ring is bonded to the diketopyrrolopyrrole skeleton can also be used.
[0032] As the red colorant, C.I. Pigment Red 122, 177, 254, 255, 264, 269, 27 are preferred, C.I. Pigment Red 254, 264, 272 are more preferred, and C.I. Pigment Red 254, 264 are even more preferred.
[0033] Examples of the green colorant include phthalocyanine compounds, squarylium compounds, etc. For the reason that it is easy to form a film with more excellent long-term reliability, it is preferably a phthalocyanine compound. Also, the green colorant is preferably a pigment.
[0034] Specific examples of the green colorant include green pigments such as C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66. Also, as the green colorant, a zinc phthalocyanine pigment in which the average number of halogen atoms in one molecule is 10 to 14, the average number of bromine atoms is 8 to 12, and the average number of chlorine atoms is 2 to 5 can also be used. Specific examples include the compounds described in International Publication No. 2015 / 118720. Also, as the green colorant, the compounds described in Chinese Patent Application No. 106909027, the phthalocyanine compound having a phosphate ester as a ligand described in International Publication No. 2012 / 102395, the phthalocyanine compound described in JP-A No. 2019-008014, the phthalocyanine compound described in JP-A No. 2018-180023, the compounds described in JP-A No. 2019-038958, the squarylium compounds described in paragraphs 0141 to 0151 of International Publication No. 2019 / 167589, etc. can be used.
[0035] As the green colorant, C.I. Pigment Green 7, 36, 58, 62, 63 are preferred, and C.I. Pigment Green 36, 58 are more preferred.
[0036] Specific examples of the orange colorant include orange pigments such as C.I. Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc.
[0037] Specific examples of the purple colorant include purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, 61, etc.
[0038] Specific examples of the blue colorant include blue pigments such as C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88, etc.
[0039] Examples of the black colorant include bisbenzofuranone compounds, azomethine compounds, perylene compounds, azo compounds, etc. Bisbenzofuranone compounds and perylene compounds are preferred. Examples of the bisbenzofuranone compounds include the compounds described in JP-T-2010-534726, JP-T-2012-515233, JP-T-2012-515234, etc. For example, it is available as "Irgaphor Black" manufactured by BASF. Examples of the perylene compounds include the compounds described in paragraphs 0016 to 0020 of JP-A-2017-226821, C.I. Pigment Black 31, 32, etc. Examples of the azomethine compounds include the compounds described in JP-A-01-170601, JP-A-02-034664, etc. For example, it can be obtained as "Chromophine Black A1103" manufactured by Dainichi Seika Chemicals Co., Ltd.
[0040] When the coloring composition of the present invention contains a green colorant, it is preferably used as a coloring composition for forming a green pixel of a color filter. When the coloring composition of the present invention contains a red colorant, it is preferably used as a coloring composition for forming a red pixel of a color filter.
[0041] In addition, the colorant contained in the coloring composition may include two or more chromatic colorants, and black may be formed by a combination of two or more chromatic colorants. Such a coloring composition is preferably used as a coloring composition for forming an infrared transmission filter. Examples of the combination of chromatic colorants for forming black by combining two or more chromatic colorants are as follows. (1) A mode containing a red colorant, a blue colorant, and a yellow colorant. (2) A mode containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant. (3) A mode containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant. (4) A mode containing a red colorant, a blue colorant, a yellow colorant, and a green colorant. (5) A mode containing a yellow colorant and a purple colorant.
[0042] The content of the colorant in the total solid content of the coloring composition is preferably 40% by mass or more, more preferably 50% by mass or more, and still more preferably 55% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and still more preferably 70% by mass or less.
[0043] The content of the yellow colorant in the colorant is 30% by mass or more, preferably 33% by mass or more, and more preferably 35% by mass or more for the reason of improving the color separation property from the blue pixels. The upper limit can be 100% by mass, can also be 95% by mass or less, and can also be 90% by mass or less.
[0044] In addition, the content of the azomethine metal complex in the yellow colorant is 15% by mass or more, preferably 15.5% by mass or more, and more preferably 16% by mass or more. The upper limit can be 100% by mass, can also be 95% by mass or less, and can also be 90% by mass or less.
[0045] In addition, the content of the quinophthalone compound in the yellow colorant is preferably less than 50% by mass, more preferably 40% by mass or less, still more preferably 30% by mass or less, and particularly preferably substantially not contained, from the viewpoint of light resistance. In the present specification, when the yellow colorant substantially does not contain a quinophthalone compound, it means that the content of the quinophthalone compound in the yellow colorant is 0.1% by mass or less, preferably 0.05% by mass or less, more preferably 0.01% by mass or less, and particularly preferably does not contain a quinophthalone compound.
[0046] The content of the azomethine metal complex in the total solid content of the coloring composition is preferably 3% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, still more preferably 70% by mass or less.
[0047] When the coloring composition of the present invention is used as a coloring composition for forming a green pixel of a color filter, it is preferable to use a colorant containing a yellow colorant and a green colorant. The mass ratio of the yellow colorant to the green colorant is preferably from 30:70 to 70:30, more preferably from 30:70 to 60:40, still more preferably from 30:70 to 50:50. In addition, the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, still more preferably 10 parts by mass or more with respect to 100 parts by mass of the green colorant. In addition, the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, still more preferably 10 parts by mass or more with respect to 100 parts by mass of the phthalocyanine compound.
[0048] When the coloring composition of the present invention is used as a coloring composition for forming a red pixel of a color filter, it is preferable to use a coloring agent containing a yellow coloring agent and a red coloring agent. Further, the mass ratio of the yellow coloring agent to the red coloring agent is preferably from 30:70 to 70:30, more preferably from 30:70 to 60:40, and still more preferably from 30:70 to 50:50. Further, the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and still more preferably 10 parts by mass or more with respect to 100 parts by mass of the red coloring agent. Further, the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and still more preferably 10 parts by mass or more with respect to 100 parts by mass of the diketopyrrolopyrrole compound.
[0049] <<Resin>> The coloring composition of the present invention contains a resin. The resin is blended, for example, for the purpose of dispersing pigments and the like in the coloring composition or for use as a binder. The resin mainly used for dispersing pigments and the like in the coloring composition is also referred to as a dispersant. However, such uses of the resin are merely examples, and the resin can also be used for purposes other than these.
[0050] The weight average molecular weight (Mw) of the resin is preferably from 2000 to 2000000. The upper limit is preferably 1000000 or less, more preferably 500000 or less. The lower limit is preferably 3000 or more, more preferably 5000 or more.
[0051] Examples of the resin include (meth)acrylic resin, epoxy resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, and the like. One of these resins may be used alone, or two or more thereof may be mixed and used.
[0052] The coloring composition of the present invention preferably contains a resin having an acid group. Examples of the acid group include a carboxyl group, a phosphoric acid group, a sulfo group, a phenolic hydroxy group, and the like. These acid groups may be only one kind or two or more kinds. The resin having an acid group can also be used as a dispersant. By containing a resin having an acid group in the coloring composition of the present invention, a desired pattern can be formed by alkali development. The acid value of the resin having an acid group is preferably 30 to 500 mgKOH / g. The lower limit is preferably 50 mgKOH / g or more, more preferably 70 mgKOH / g or more. The upper limit is preferably 400 mgKOH / g or less, more preferably 200 mgKOH / g or less, still more preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
[0053] The coloring composition of the present invention preferably contains a resin having a basic group. The resin having a basic group is preferably a resin containing a repeating unit having a basic group in the side chain, more preferably a copolymer having a repeating unit having a basic group in the side chain and a repeating unit not containing a basic group, and still more preferably a block copolymer having a repeating unit having a basic group in the side chain and a repeating unit not containing a basic group. The resin having a basic group can also be used as a dispersant. The amine value of the resin having a basic group is preferably 5 to 300 mgKOH / g. The lower limit is preferably 10 mgKOH / g or more, more preferably 20 mgKOH / g or more. The upper limit is preferably 200 mgKOH / g or less, more preferably 100 mgKOH / g or less. Examples of the basic group contained in the resin having a basic group include a group represented by the following formula (a-1) and a group represented by the following formula (a-2).
Chemical formula
[0054] In formula (a-1), R a1 and R a2 each independently represents a hydrogen atom, an alkyl group or an aryl group, and Ra1 and R a2 may combine to form a ring; In formula (a-2), R a11 represents a hydrogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an acyl group or an oxy radical, and R a12 ~R a19 each independently represents a hydrogen atom, an alkyl group or an aryl group.
[0055] R a1 , R a2 , R a11 ~R a19 The alkyl group represented by preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, still more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 5 carbon atoms. The alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent.
[0056] R a1 , R a2 , R a11 ~R a19 The aryl group represented by preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms. The aryl group may have a substituent.
[0057] R a11 The alkoxy group represented by preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, still more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 5 carbon atoms. The alkoxy group may have a substituent.
[0058] R a11 The aryloxy group represented by preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms. The aryloxy group may have a substituent.
[0059] R a11 The acyl group represented by preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and still more preferably 2 to 12 carbon atoms. The acyl group may have a substituent.
[0060] Examples of commercially available resins having basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (manufactured by BYK-Chemie Japan Co., Ltd. for all the above), SOLSPERSE11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (manufactured by Lubrizol Japan Ltd. for all the above), Efka PX 4300, 4330, 4046, 4060, 4080 (manufactured by BASF for all the above), etc. Further, as the resin having a basic group, a block copolymer (B) described in paragraph numbers 0063 to 0112 of JP-A-2014-219665 and a block copolymer A1 described in paragraph numbers 0046 to 0076 of JP-A-2018-156021 can also be used, and the contents thereof are incorporated herein.
[0061] The coloring composition of the present invention preferably contains a resin having an acid group and a resin having a basic group, respectively. According to this aspect, the storage stability of the coloring composition can be further improved. When the resin having an acid group and the resin having a basic group are used in combination, the content of the resin having a basic group is preferably 20 to 500 parts by mass, more preferably 30 to 300 parts by mass, and still more preferably 50 to 200 parts by mass with respect to 100 parts by mass of the resin having an acid group.
[0062] The resin preferably includes a resin containing a repeating unit derived from a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may also be referred to as "ether dimer").
[0063]
Chemical formula
[0064] In formula (ED1), R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent. [Chemical formula] In formula (ED2), R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. As a specific example of formula (ED2), the description in JP-A-2010-168539 can be referred to.
[0065] Regarding specific examples of the ether dimer, paragraph number 0317 of JP-A-2013-029760 can be referred to, and this content is incorporated herein.
[0066] As the resin, it is also preferable to include a resin containing a repeating unit having a polymerizable group.
[0067] As the resin, it is also preferable to include a resin containing a repeating unit derived from the compound represented by formula (X). [Chemical formula] In the formula, R 1 represents a hydrogen atom or a methyl group, R 21 and R 22 each independently represent an alkylene group, and n represents an integer of 0 to 15. The number of carbon atoms of the alkylene group represented by R 21 and R 22 is preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, and particularly preferably 2 or 3. n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and still more preferably an integer of 0 to 3.
[0068] Examples of the compound represented by formula (X) include ethylene oxide or propylene oxide-modified (meth)acrylate of paracumylphenol. Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
[0069] It is also preferable to include a resin having an aromatic carboxyl group (hereinafter also referred to as resin Ac). In resin Ac, the aromatic carboxyl group may be contained in the main chain of the repeating unit or in the side chain of the repeating unit. It is preferable that the aromatic carboxyl group is contained in the main chain of the repeating unit. In the present specification, the aromatic carboxyl group refers to a group having one or more carboxyl groups bonded to an aromatic ring. In the aromatic carboxyl group, the number of carboxyl groups bonded to the aromatic ring is preferably 1 to 4, more preferably 1 to 2.
[0070] Resin Ac is preferably a resin containing at least one repeating unit selected from the repeating unit represented by formula (Ac-1) and the repeating unit represented by formula (Ac-2).
Chemical formula
[0071] In formula (Ac-1), examples of the group containing an aromatic carboxyl group represented by Ar 1 include a structure derived from an aromatic tricarboxylic acid anhydride, a structure derived from an aromatic tetracarboxylic acid anhydride, and the like. Examples of the aromatic tricarboxylic acid anhydride and the aromatic tetracarboxylic acid anhydride include compounds having the following structures.
Chemical formula
[0072] In the above formula, Q 1 represents a single bond, -O-, -CO-, -COOCH2CH2OCO-, -SO2-, -C(CF3)2-, a group represented by the following formula (Q-1) or a group represented by the following formula (Q-2). [Chemical formula]
[0073] Ar 1 Specific examples of the group containing an aromatic carboxyl group represented by Ar include a group represented by formula (Ar-11), a group represented by formula (Ar-12), a group represented by formula (Ar-13), and the like. [Chemical formula]
[0074] In formula (Ar-11), n1 represents an integer from 1 to 4, preferably 1 or 2, and more preferably 2. In formula (Ar-12), n2 represents an integer from 1 to 8, preferably an integer from 1 to 4, more preferably 1 or 2, and even more preferably 2. In formula (Ar-13), n3 and n4 each independently represent an integer from 0 to 4, preferably an integer from 0 to 2, more preferably 1 or 2, and even more preferably 1. However, at least one of n3 and n4 is an integer of 1 or more. In formula (Ar-13), Q 1 represents a single bond, -O-, -CO-, -COOCH2CH2OCO-, -SO2-, -C(CF3)2-, a group represented by the above formula (Q-1) or a group represented by the above formula (Q-2).
[0075] In formula (Ac-1), L 1 represents -COO- or -CONH-, and preferably represents -COO-.
[0076] In formula (Ac-1), L 2Examples of the divalent linking group represented by include an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and a group formed by combining two or more of these. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The alkylene group may be linear, branched, or cyclic. The number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 10. The alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group. L 2 The divalent linking group represented by is -O-L 2a It is preferably a group represented by -O-. L 2a Examples of L include an alkylene group; an arylene group; a group formed by combining an alkylene group and an arylene group; and a group formed by combining at least one selected from an alkylene group and an arylene group with at least one selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The alkylene group may be linear, branched, or cyclic. The alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group.
[0077] In formula (Ac-2), Ar 10 Examples of the group containing an aromatic carboxyl group represented by are the same as Ar in formula (Ac-1), 1 and the preferred ranges are also the same.
[0078] In formula (Ac-2), L 11 represents -COO- or -CONH-, and preferably represents -COO-.
[0079] In formula (Ac-2), L 12Examples of the trivalent linking group represented by [are hydrocarbon groups, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and groups formed by combining two or more of these. Hydrocarbon groups include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The aliphatic hydrocarbon group may be linear, branched, or cyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include a hydroxy group.
[0080] In formula (Ac-2), P 10 represents a polymer chain. P 10 The polymer chain represented by [preferably has at least one repeating unit selected from poly(meth)acrylic repeating units, polyether repeating units, polyester repeating units, and polyol repeating units. The polymer chain P 10 preferably has a weight average molecular weight of 500 to 20,000. The lower limit is preferably 1000 or more. The upper limit is preferably 10,000 or less, more preferably 5000 or less, and still more preferably 3000 or less. When the weight average molecular weight of P 10 is within the above range, the dispersibility of the pigment in the composition is good. When the resin having an aromatic carboxyl group is a resin having a repeating unit represented by formula (Ac-2), this resin is preferably used as a dispersant.
[0081] The resin preferably contains a resin as a dispersant. Examples of the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin). Here, the acidic dispersant (acidic resin) refers to a resin in which the amount of acid groups is larger than the amount of basic groups. As the acidic dispersant (acidic resin), a resin in which the amount of acid groups is 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol% is preferable. The acid group of the acidic dispersant (acidic resin) is preferably a carboxyl group. The acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH / g. Also, the basic dispersant (basic resin) refers to a resin in which the amount of basic groups is larger than the amount of acid groups. As the basic dispersant (basic resin), a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the amount of acid groups and the amount of basic groups is 100 mol% is preferable. The basic group of the basic dispersant is preferably an amino group.
[0082] The resin used as the dispersant is also preferably a graft resin. For details of the graft resin, reference can be made to the descriptions in paragraphs 0025 to 0094 of JP-A-2012-255128, and this content is incorporated herein.
[0083] The resin used as the dispersant is also preferably a resin having an aromatic carboxyl group (resin Ac). Examples of the resin having an aromatic carboxyl group include those described above.
[0084] The resin used as the dispersant is also preferably a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain. As the polyimine-based dispersant, a resin having a main chain having a partial structure having a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and having a basic nitrogen atom in at least one of the main chain and the side chain is preferable. The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity. Regarding the polyimine-based dispersant, reference can be made to the descriptions in paragraphs 0102 to 0166 of JP-A-2012-255128, and this content is incorporated herein.
[0085] The resin used as the dispersant is preferably a resin having a structure in which a plurality of polymer chains are bonded to the core part. Examples of such resins include dendrimers (including star polymers). Specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A-2013-043962.
[0086] The resin used as the dispersant is preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in the side chain. The content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and still more preferably 20 to 70 mol% based on all the repeating units of the resin. Further, the resin described in JP-A-2018-087939 can also be used as the dispersant.
[0087] The dispersant is also available as a commercial product. Specific examples thereof include the DISPERBYK series manufactured by BYK Japan Co., Ltd., the SOLSPERSE series manufactured by Lubrizol Japan Co., Ltd., the Efka series manufactured by BASF SE, and the Ajiper series manufactured by Ajinomoto Fine-Techno Co., Inc. Further, the products described in paragraph 0129 of JP-A-2012-137564 and the products described in paragraph 0235 of JP-A-2017-194662 can also be used as the dispersant.
[0088] Further, as the resin used as the dispersant, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Patent No. 6432077 can also be used.
[0089] The content of the resin in the total solid of the coloring composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, more preferably 40% by mass or less. The coloring composition of the present invention may contain only one kind of resin, or may contain two or more kinds of resins. When two or more kinds of resins are contained, the total amount thereof is preferably within the above range.
[0090] <<Solvent>> The coloring composition of the present invention contains a solvent. Examples of the solvent include organic solvents. The type of the solvent is not particularly limited basically as long as the solubility of each component and the coatability of the composition are satisfied. Examples of the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents and the like. For details thereof, reference can be made to paragraph number 0223 of WO 2015 / 166779, and this content is incorporated herein. In addition, ester solvents substituted with a cyclic alkyl group and ketone solvents substituted with a cyclic alkyl group can also be preferably used. Specific examples of the organic solvent include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide and the like. However, aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may preferably be reduced for reasons such as environmental aspects (for example, it can be 50 ppm (parts per million) or less, 10 ppm or less, or 1 ppm or less based on the total amount of the organic solvent).
[0091] In the present invention, it is preferable to use an organic solvent having a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at the mass ppt (parts per trillion) level may be used. Such an organic solvent is provided by, for example, Toyo Gosei Co., Ltd. (Chemical Industry Daily, November 13, 2015).
[0092] Examples of methods for removing impurities such as metals from the organic solvent include distillation (such as molecular distillation and thin-film distillation) and filtration using a filter. The filter pore size of the filter used for filtration is preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less. The material of the filter is preferably polytetrafluoroethylene, polyethylene, or nylon.
[0093] The organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds of isomers may be contained.
[0094] The content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
[0095] The content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
[0096] In addition, from the perspective of environmental regulations, it is preferable that the coloring composition of the present invention substantially does not contain environmentally regulated substances. In the present invention, substantially not containing environmentally regulated substances means that the content of environmentally regulated substances in the coloring composition is 50 mass ppm or less, preferably 30 mass ppm or less, more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less. Examples of environmentally regulated substances include benzene; alkylbenzenes such as toluene and xylene; halogenated benzenes such as chlorobenzene. These are registered as environmentally regulated substances under regulations such as the REACH (Registration, Evaluation, Authorization and Restriction of Chemicals) Regulation, the PRTR (Pollutant Release and Transfer Register) Law, and the VOC (Volatile Organic Compounds) Regulation, and their usage amounts and handling methods are strictly regulated. These compounds may be used as solvents when manufacturing each component used in the coloring composition, etc., and may be mixed into the coloring composition as residual solvents. From the viewpoints of safety to humans and consideration for the environment, it is preferable to reduce these substances as much as possible. As a method for reducing environmentally regulated substances, there is a method of heating or reducing the pressure in the system to a temperature above the boiling point of the environmentally regulated substances and distilling off the environmentally regulated substances from the system for reduction. Also, when distilling off a small amount of environmentally regulated substances, it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the corresponding solvent in order to improve efficiency. Further, when containing a compound having radical polymerizability, a polymerization inhibitor or the like may be added and distilled off under reduced pressure in order to suppress the progress of the radical polymerization reaction and crosslinking between molecules during distillation under reduced pressure. These distillation methods are possible at any stage, such as at the raw material stage, at the stage of the product obtained by reacting the raw materials (for example, a resin solution or a polyfunctional monomer solution after polymerization), or at the stage of the coloring composition prepared by mixing these compounds.
[0097] <<Pigment Derivative>> The coloring composition of the present invention can contain a pigment derivative. Examples of the pigment derivative include compounds having a structure in which an acid group or a basic group is bonded to a dye skeleton. Examples of the dye skeleton constituting the pigment derivative include a quinoline dye skeleton, a benzimidazolone dye skeleton, a benzisoindole dye skeleton, a benzothiazole dye skeleton, an iminium dye skeleton, a squarylium dye skeleton, a croconium dye skeleton, an oxonol dye skeleton, a pyrrolopyrrole dye skeleton, a diketopyrrolopyrrole dye skeleton, an azo dye skeleton, an azomethine dye skeleton, a phthalocyanine dye skeleton, a naphthalocyanine dye skeleton, an anthraquinone dye skeleton, a quinacridone dye skeleton, a dioxazine dye skeleton, a perinone dye skeleton, a perylene dye skeleton, a thioindigo dye skeleton, an isoindoline dye skeleton, an isoindolinone dye skeleton, a quinophthalone dye skeleton, an iminium dye skeleton, a dithiol dye skeleton, a triarylmethane dye skeleton, a pyromethene dye skeleton, and the like. Examples of the acid group include a sulfo group, a carboxyl group, a phosphate group, and salts thereof. Examples of the atom or atomic group constituting the salt include an alkali metal ion (Li + , Na + , K + , etc.), an alkaline earth metal ion (Ca 2+ , Mg 2+ , etc.), an ammonium ion, an imidazolium ion, a pyridinium ion, a phosphonium ion, and the like. Examples of the basic group include an amino group, a pyridinyl group and its salt, a salt of an ammonium group, and a phthalimidomethyl group. Examples of the atom or atomic group constituting the salt include a hydroxide ion, a halogen ion, a carboxylate ion, a sulfonate ion, a phenoxide ion, and the like.
[0098] In addition, as the pigment derivative, it is also preferable to use a compound having a structure with a triazine skeleton and an acid group or a basic group. Since the structure of the triazine skeleton of the pigment derivative is similar to that of the pteridine skeleton of the pteridine pigment, the pigment derivative is likely to adsorb on the surface of the pteridine pigment. As a result, it is presumed that a strong network is formed among the pteridine pigment, the pigment derivative, and the resin. By forming such a network, the dispersibility of the pteridine pigment in the coloring composition can be further improved, and the temporal stability of the coloring composition can be further improved. Furthermore, it is easy to form a film with suppressed occurrence of defects. Also, when the network between the pigment and the resin becomes strong, the pigment is more likely to be developed together with the resin, and the developability can be further improved.
[0099] The coloring composition may also contain a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative). The maximum value (εmax) of the molar absorption coefficient in the wavelength range of 400 to 700 nm of the transparent pigment derivative is preferably 3000 L·mol -1 ·cm -1 or less, more preferably 1000 L·mol -1 ·cm -1 or less, and even more preferably 100 L·mol -1 ·cm -1 or less. The lower limit of εmax is, for example, 1 L·mol -1 ·cm -1 or more, and may also be 10 L·mol -1 ·cm -1 or more.
[0100] Specific examples of the pigment derivative include the compounds described in the examples described later, JP-A-56-118462, JP-A-63-264674, JP-A-01-217077, JP-A-03-009961, JP-A-03-026767, JP-A-03-153780, JP-A-03-045662, JP-A-04-285669, JP-A-06-145546, JP-A-06-212088, JP-A-06-240158, JP-A-10-030063, JP-A-10-195326, paragraph numbers 0086 to 0098 of International Publication No. 2011 / 024896, paragraph numbers 0063 to 0094 of International Publication No. 2012 / 102399, paragraph number 0082 of International Publication No. 2017 / 038252, paragraph number 0171 of JP-A-2015-151530, paragraph numbers 0162 to 0183 of JP-A-2011-252065, JP-A-03-081972, Patent No. 5299151, JP-A-2015-172732, JP-A-2014-199308, JP-A-2014-085562, JP-A-2014-035351, and JP-A-2008-081565.
[0101] When the pigment derivative is contained, the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 2 to 15 parts by mass, and still more preferably 4 to 10 parts by mass with respect to 100 parts by mass of the pigment. Only one kind of the pigment derivative may be used, or two or more kinds may be used in combination. When two or more kinds are used in combination, it is preferable that the total amount thereof is within the above range.
[0102] <<Infrared Absorbent>> The coloring composition of the present invention can further contain an infrared absorber. For example, when forming an infrared transmission filter using the coloring composition of the present invention, the wavelength of the light transmitted through the film obtained by containing an infrared absorber in the coloring composition can be shifted to a longer wavelength side. The infrared absorber is preferably a compound having a maximum absorption wavelength on the longer wavelength side than 700 nm. The infrared absorber is preferably a compound having a maximum absorption wavelength in the range exceeding 700 nm and 1800 nm or less. Further, the absorbance A at 500 nm of the infrared absorber 1 and the absorbance A at the maximum absorption wavelength 2 The ratio A of 1 / A 2 is preferably 0.08 or less, and more preferably 0.04 or less.
[0103] Examples of the infrared absorber include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, etc. Examples of the pyrrolopyrrole compounds include the compounds described in paragraph numbers 0016 to 0058 of JP-A No. 2009-263614, the compounds described in paragraph numbers 0037 to 0052 of JP-A No. 2011-068731, the compounds described in paragraph numbers 0010 to 0033 of WO 2015 / 166873, etc. Examples of the squarylium compounds include the compounds described in paragraph numbers 0044 to 0049 of JP-A No. 2011-208101, the compounds described in paragraph numbers 0060 to 0061 of Patent No. 6065169, the compound described in paragraph number 0040 of WO 2016 / 181987, the compounds described in JP-A No. 2015-176046, the compound described in paragraph number 0072 of WO 2016 / 190162, the compounds described in paragraph numbers 0196 to 0228 of JP-A No. 2016-074649, the compound described in paragraph number 0124 of JP-A No. 2017-067963, the compounds described in WO 2017 / 135359, the compounds described in JP-A No. 2017-114956, the compounds described in Patent No. 6197940, the compounds described in WO 2016 / 120166, etc. Examples of the cyanine compounds include the compounds described in paragraph numbers 0044 to 0045 of JP-A No. 2009-108267, the compounds described in paragraph numbers 0026 to 0030 of JP-A No. 2002-194040, the compounds described in JP-A No. 2015-172004, the compounds described in JP-A No. 2015-172102, the compounds described in JP-A No. 2008-088426, the compound described in paragraph number 0090 of WO 2016 / 190162, the compounds described in JP-A No. 2017-031394, etc. Examples of the croconium compounds include the compounds described in JP-A No. 2017-082029.Examples of the iminium compound include compounds described in JP-T-2008-528706, compounds described in JP-A-2012-012399, compounds described in JP-A-2007-092060, and compounds described in paragraphs 0048 to 0063 of WO 2018 / 043564. Examples of the phthalocyanine compound include compounds described in paragraph 0093 of JP-A-2012-077153, oxytitanium phthalocyanine described in JP-A-2006-343631, compounds described in paragraphs 0013 to 0029 of JP-A-2013-195480, and vanadium phthalocyanine compounds described in JP-B-6081771. Examples of the naphthalocyanine compound include compounds described in paragraph 0093 of JP-A-2012-077153. Examples of the dithiolene metal complex include compounds described in JP-B-5733804. Examples of the metal oxide include indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, tungsten oxide, and the like. Regarding the details of tungsten oxide, paragraph 0080 of JP-A-2016-006476 can be referred to, and this content is incorporated herein. Examples of the metal boride include lanthanum boride and the like. Commercially available products of lanthanum boride include LaB6-F (manufactured by Nippon New Metal Co., Ltd.) and the like. Also, as the metal boride, the compounds described in WO 2017 / 119394 can be used. Commercially available products of indium tin oxide include F-ITO (manufactured by DOWA High-Tech Co., Ltd.) and the like.
[0104] In addition, as the infrared absorber, squarylium compounds described in JP-A-2017-197437, squarylium compounds described in JP-A-2017-025311, squarylium compounds described in International Publication No. 2016 / 154782, squarylium compounds described in Patent No. 5884953, squarylium compounds described in Patent No. 6036689, squarylium compounds described in Patent No. 5810604, squarylium compounds described in paragraphs 0090 to 0107 of International Publication No. 2017 / 213047, pyrrole ring-containing compounds described in paragraphs 0019 to 0075 of JP-A-2018-054760, pyrrole ring-containing compounds described in paragraphs 0078 to 0082 of JP-A-2018-040955, pyrrole ring-containing compounds described in paragraphs 0043 to 0069 of JP-A-2018-002773, squarylium compounds having an aromatic ring at the α-position of amide described in paragraphs 0024 to 0086 of JP-A-2018-041047, amide-linked squarylium compounds described in JP-A-2017-179131, compounds having a pyrrole bis-type squarylium skeleton or croconium skeleton described in JP-A-2017-141215, dihydrocarbazole bis-type squarylium compounds described in JP-A-2017-082029, asymmetric compounds described in paragraphs 0027 to 0114 of JP-A-2017-068120, pyrrole ring-containing compounds (carbazole type) described in JP-A-2017-067963, phthalocyanine compounds described in Patent No. 6251530, etc. can also be used.
[0105] When the coloring composition of the present invention contains an infrared absorber, the content of the infrared absorber in the total solid content of the coloring composition is preferably 1 to 40% by mass. The lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, and still more preferably 10% by mass or more. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less. The coloring composition of the present invention may contain only one kind of infrared absorber or two or more kinds thereof. When two or more kinds of infrared absorbers are contained, the total amount thereof is preferably within the above range.
[0106] <<Coincidence compound>> The coloring composition of the present invention can contain a polymerizable compound. As the polymerizable compound, known compounds that can be crosslinked by radicals, acids, or heat can be used. In the present invention, the polymerizable compound is preferably, for example, a compound having an ethylenically unsaturated bond-containing group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and the like. The polymerizable compound used in the present invention is preferably a radically polymerizable compound.
[0107] The polymerizable compound may be in any chemical form such as a monomer, a prepolymer, or an oligomer, but a monomer is preferred. The molecular weight of the polymerizable compound is preferably from 100 to 3000. The upper limit is more preferably 2000 or less, and even more preferably 1500 or less. The lower limit is more preferably 150 or more, and even more preferably 250 or more.
[0108] The polymerizable compound is preferably a compound containing three or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and even more preferably a compound containing 3 to 6 ethylenically unsaturated bond-containing groups. Further, the polymerizable compound is preferably a 3- to 15-functional (meth)acrylate compound, and more preferably a 3- to 6-functional (meth)acrylate compound. Specific examples of the polymerizable compound include the compounds described in paragraph numbers 0095 to 0108 of JP-A-2009-288705, paragraph 0227 of JP-A-2013-029760, paragraph numbers 0254 to 0257 of JP-A-2008-292970, paragraph numbers 0034 to 0038 of JP-A-2013-253224, paragraph number 0477 of JP-A-2012-208494, JP-A-2017-048367, Japanese Patent No. 6057891, and Japanese Patent No. 6031807, and the contents of these are incorporated herein.
[0109] Examples of the polymerizable compound include dipentaerythritol tri(meth)acrylate (commercially available as KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available as KAYARAD D-320; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available as KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available as KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds having a structure in which these (meth)acryloyl groups are bonded via ethylene glycol and / or propylene glycol residues (for example, SR454 and SR499 commercially available from Sartomer). Further, examples of the polymerizable compound include diglycerin EO (ethylene oxide) modified (meth)acrylate (commercially available as M-460; manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK Ester A-TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), NK Oligo UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), etc. can also be used.
[0110] In addition, as the polymerizable compound, trifunctional (meth)acrylate compounds such as trimethylolpropane tri(meth)acrylate, trimethylolpropane propylene oxide-modified tri(meth)acrylate, trimethylolpropane ethylene oxide-modified tri(meth)acrylate, ethylene oxide-modified tri(meth)acrylate isocyanurate, and pentaerythritol tri(meth)acrylate can also be used. Commercially available trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305, M-303, M-452, M-450 (manufactured by Toagosei Co., Ltd.), NK Ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A-TMM-3LM-N, A-TMPT, TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.), and the like.
[0111] In addition, a compound having an acid group can also be used as the polymerizable compound. By using a polymerizable compound having an acid group, the polymerizable compound in the unexposed portion is easily removed during development, and the generation of development residues can be suppressed. Examples of the acid group include a carboxyl group, a sulfo group, a phosphoric acid group, etc., and a carboxyl group is preferred. Commercially available polymerizable compounds having an acid group include Aronix M-510, M-520, Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), and the like. The preferred acid value of the polymerizable compound having an acid group is 0.1 to 40 mgKOH / g, more preferably 5 to 30 mgKOH / g. If the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in the developer is good, and if it is 40 mgKOH / g or less, it is advantageous in terms of production and handling.
[0112] In addition, a compound having a caprolactone structure can also be used as the polymerizable compound. Commercially available polymerizable compounds having a caprolactone structure include KAYARAD DPCA-20, DPCA-30, DPCA-60, DPCA-120 (all of the above are manufactured by Nippon Kayaku Co., Ltd.), and the like.
[0113] In addition, a polymerizable compound having an alkyleneoxy group can also be used. The polymerizable compound having an alkyleneoxy group is preferably a polymerizable compound having an ethyleneoxy group and / or a propyleneoxy group, more preferably a polymerizable compound having an ethyleneoxy group, and even more preferably a 3- to 6-functional (meth)acrylate compound having 4 to 20 ethyleneoxy groups. Examples of the polymerizable compound having an alkyleneoxy group include compounds having the following structure. Commercially available products of the polymerizable compound having an alkyleneoxy group include, for example, SR-494, a 4-functional (meth)acrylate having 4 ethyleneoxy groups manufactured by Sartomer, and KAYARAD TPA-330, a 3-functional (meth)acrylate having 3 isobutyleneoxy groups manufactured by Nippon Kayaku Co., Ltd.
Chemical formula
[0114] In addition, a polymerizable compound having a fluorene skeleton can also be used. Commercially available products of the polymerizable compound having a fluorene skeleton include Ogsole EA-0200, EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., (meth)acrylate monomer having a fluorene skeleton), and the like.
[0115] As the polymerizable compound, it is also preferable to use a compound that substantially does not contain environmentally regulated substances such as toluene. Commercially available products of such compounds include KAYARAD DPHA LT, KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.), and the like.
[0116] The content of the polymerizable compound in the total solid of the coloring composition is preferably 0.1 to 50% by mass. The lower limit is more preferably 0.5% by mass or more, and still more preferably 1% by mass or more. The upper limit is more preferably 45% by mass or less, and still more preferably 40% by mass or less. The polymerizable compound may be a single type or a combination of two or more types. When two or more types are used in combination, it is preferable that their total is within the above range.
[0117] <<Photoinitiator>> The coloring composition of the present invention can contain a photoinitiator. There is no particular limitation on the photoinitiator, and it can be appropriately selected from known photoinitiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable. The photoinitiator is preferably a photoradical polymerization initiator.
[0118] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, α-hydroxyketone compounds, α-aminoketone compounds, and the like. From the viewpoint of exposure sensitivity, the photopolymerization initiator is preferably a trihalomethyltriazine compound, a benzyldimethylketal compound, an α-hydroxyketone compound, an α-aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a triarylimidazole dimer, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, and a 3-aryl-substituted coumarin compound, more preferably a compound selected from an oxime compound, an α-hydroxyketone compound, an α-aminoketone compound, and an acylphosphine compound, and still more preferably an oxime compound. Further, examples of the photopolymerization initiator include the compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173, the compounds described in Japanese Patent No. 6301489, the peroxide-based photopolymerization initiators described in MATERIAL STAGE 37 to 60p, vol. 19, No. 3, 2019, the photopolymerization initiators described in International Publication No. 2018 / 221177, the photopolymerization initiators described in International Publication No. 2018 / 110179, the photopolymerization initiators described in JP-A-2019-043864, and the photopolymerization initiators described in JP-A-2019-044030, and the contents of these are incorporated herein.
[0119] Examples of commercially available α-hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (manufactured by BASF), and the like. Examples of commercially available α-aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by BASF), and the like. Examples of commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (manufactured by BASF), and the like.
[0120] Examples of the oxime compound include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, compounds described in J.C.S. Perkin II (1979, pp. 1653-1660), compounds described in J.C.S. Perkin II (1979, pp. 156-162), compounds described in Journal of Photopolymer Science and Technology (1995, pp. 202-232), compounds described in JP-A-2000-066385, compounds described in JP-T-2004-534797, compounds described in JP-A-2006-342166, compounds described in JP-A-2017-019766, compounds described in Patent No. 6065596, compounds described in International Publication No. 2015 / 152153, compounds described in International Publication No. 2017 / 051680, compounds described in JP-A-2017-198865, compounds described in paragraphs 0025 to 0038 of International Publication No. 2017 / 164127, compounds described in International Publication No. 2013 / 167515, and the like. Specific examples of the oxime compound include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, and 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one. Commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04 (all manufactured by BASF), TR-PBG-304 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.), Adeka Optomer N-1919 (manufactured by ADEKA CORPORATION, photoinitiator 2 described in JP-A-2012-014052). Further, as the oxime compound, it is also preferable to use a compound having no coloring property or a compound having high transparency and being difficult to discolor.Examples of commercially available products include Adeka Arcles NCI-730, NCI-831, NCI-930 (all manufactured by ADEKA CORPORATION), etc.
[0121] As the photopolymerization initiator, an oxime compound having a fluorene ring can also be used. Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
[0122] As the photopolymerization initiator, an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring can also be used. Specific examples of such an oxime compound include the compounds described in WO2013 / 083505.
[0123] As the photopolymerization initiator, an oxime compound having a fluorine atom can also be used. Specific examples of the oxime compound having a fluorine atom include the compounds described in JP-A-2010-262028, the compounds 24, 36 to 40 described in JP-T-2014-500852, the compound (C-3) described in JP-A-2013-164471, etc.
[0124] As the photopolymerization initiator, an oxime compound having a nitro group can be used. The oxime compound having a nitro group is preferably a dimer. Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP-A-2013-114249, paragraphs 0008 to 0012 and 0070 to 0079 of JP-A-2014-137466, the compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, and Adeka Arcles NCI-831 (manufactured by ADEKA CORPORATION).
[0125] As the photopolymerization initiator, an oxime compound having a benzofuran skeleton can also be used. Specific examples include OE-01 to OE-75 described in WO2015 / 036910.
[0126] As the photopolymerization initiator, an oxime compound in which a substituent having a hydroxy group is bonded to a carbazole skeleton can also be used. Examples of such photopolymerization initiators include the compounds described in International Publication No. 2019 / 088055.
[0127] Specific examples of the oxime compound preferably used in the present invention are shown below, but the present invention is not limited thereto.
[0128] [Chemical formula] [Chemical formula]
[0129] The oxime compound is preferably a compound having a maximum absorption wavelength in the range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in the range of 360 to 480 nm. Further, from the viewpoint of sensitivity, the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably 1000 to 300000, still more preferably 2000 to 300000, and particularly preferably 5000 to 200000. The molar extinction coefficient of the compound can be measured using a known method. For example, it is preferably measured at a concentration of 0.01 g / L using an ethyl acetate solvent with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
[0130] As the photopolymerization initiator, it is also preferable to use a combination of Irgacure OXE01 (manufactured by BASF) and / or Irgacure OXE02 (manufactured by BASF) and Omnirad 2959 (manufactured by IGM Resins B.V.).
[0131] As the photoinitiator, a bifunctional or trifunctional or higher-functional photo radical polymerization initiator may be used. By using such a photo radical polymerization initiator, two or more radicals are generated from one molecule of the photo radical polymerization initiator, so that good sensitivity can be obtained. Further, when a compound having an asymmetric structure is used, the crystallinity is lowered, the solubility in a solvent or the like is improved, and it becomes difficult to precipitate over time, and the stability over time of the coloring composition can be improved. Specific examples of the bifunctional or trifunctional or higher-functional photo radical polymerization initiator include those described in JP-T-2010-527339, JP-T-2011-524436, WO 2015 / 004565, paragraph numbers 0407 to 0412 of JP-T-2016-532675, dimer of oxime compounds described in paragraph numbers 0039 to 0055 of WO 2017 / 033680, compound (E) and compound (G) described in JP-T-2013-522445, Cmpd1 to 7 described in WO 2016 / 034963, oxime ester photoinitiators described in paragraph number 0007 of JP-T-2017-523465, photoinitiators described in paragraph numbers 0020 to 0033 of JP 2017-167399 A, photo radical polymerization initiator (A) described in paragraph numbers 0017 to 0026 of JP 2017-151342 A, oxime ester photoinitiator described in Japanese Patent No. 6469669, and the like.
[0132] When containing a photoinitiator, the content of the photoinitiator in the total solid content of the coloring composition is preferably 0.1 to 30% by mass. The lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more. The upper limit is preferably 20% by mass or less, more preferably 15% by mass or less. In the coloring composition of the present invention, only one kind of photoinitiator may be used, or two or more kinds may be used. When two or more kinds are used, the total amount thereof is preferably within the above range.
[0133] <<Compound having a cyclic ether group>> The coloring composition of the present invention can contain a compound having a cyclic ether group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group. The compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound). As the epoxy compound, the compounds described in paragraph numbers 0034 to 0036 of JP-A-2013-011869, paragraph numbers 0147 to 0156 of JP-A-2014-043556, paragraph numbers 0085 to 0092 of JP-A-2014-089408, and the compounds described in JP-A-2017-179172 can also be used. These contents are incorporated herein.
[0134] The epoxy compound may be a low molecular weight compound (for example, having a molecular weight of less than 2000, and further less than 1000), or a macromolecule (for example, having a molecular weight of 1000 or more, and in the case of a polymer, having a weight average molecular weight of 1000 or more). The weight average molecular weight of the epoxy compound is preferably from 200 to 100000, more preferably from 500 to 50000. The upper limit of the weight average molecular weight is preferably 10000 or less, more preferably 5000 or less, and still more preferably 3000 or less.
[0135] As the epoxy compound, an epoxy resin can be preferably used. Examples of the epoxy resin include an epoxy resin which is a glycidyl etherified product of a phenolic compound, an epoxy resin which is a glycidyl etherified product of various novolak resins, an alicyclic epoxy resin, an aliphatic epoxy resin, a heterocyclic epoxy resin, a glycidyl ester type epoxy resin, a glycidylamine type epoxy resin, an epoxy resin obtained by glycidylating halogenated phenols, a condensate of a silicon compound having an epoxy group and another silicon compound, a copolymer of a polymerizable unsaturated compound having an epoxy group and another polymerizable unsaturated compound, and the like. The epoxy equivalent of the epoxy resin is preferably from 310 to 3300 g / eq, more preferably from 310 to 1700 g / eq, and still more preferably from 310 to 1000 g / eq.
[0136] Examples of commercially available compounds having a cyclic ether group include EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DIC Corporation), Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (above, manufactured by NOF Corporation, epoxy group-containing polymers), and the like.
[0137] The content of the compound having a cyclic ether group in the total solid content of the coloring composition is preferably 0.1 to 20% by mass. The lower limit is preferably, for example, 0.5% by mass or more, more preferably 1% by mass or more. The upper limit is preferably, for example, 15% by mass or less, still more preferably 10% by mass or less. The compound having a cyclic ether group may be only one kind or two or more kinds. In the case of two or more kinds, it is preferable that their total amount falls within the above range.
[0138] <<Curing accelerator>> The coloring composition of the present invention may contain a curing accelerator. Examples of the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds, and the like. Specific examples of the curing accelerator include the compounds described in paragraph numbers 0094 to 0097 of International Publication No. 2018 / 056189, the compounds described in paragraph numbers 0246 to 0253 of JP-A-2015-034963, the compounds described in paragraph numbers 0186 to 0251 of JP-A-2013-041165, the ionic compounds described in JP-A-2014-055114, the compounds described in paragraph numbers 0071 to 0080 of JP-A-2012-150180, the alkoxysilane compounds having an epoxy group described in JP-A-2011-253054, the compounds described in paragraph numbers 0085 to 0092 of Patent No. 5765059, the carboxyl group-containing epoxy curing agents described in JP-A-2017-036379, and the like. When the curing accelerator is contained, the content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
[0139] <<Ultraviolet absorber>> The coloring composition of the present invention can contain an ultraviolet absorber. As the ultraviolet absorber, a conjugated diene compound, an amino diene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indole compound, a triazine compound, etc. can be used. As such compounds, those described in paragraph numbers 0038 to 0052 of JP-A No. 2009-217221, paragraph numbers 0052 to 0072 of JP-A No. 2012-208374, paragraph numbers 0317 to 0334 of JP-A No. 2013-068814, and paragraph numbers 0061 to 0080 of JP-A No. 2016-162946 can be mentioned, and the contents of these are incorporated herein. Specific examples of the ultraviolet absorber include compounds having the following structures. As commercially available products of the ultraviolet absorber, for example, UV-503 (manufactured by Daito Chemical Co., Ltd.) can be mentioned. Further, as the benzotriazole compound, the MYUA series manufactured by Miyoshi Oil & Fat Co., Ltd. (Chemical Industry Daily, February 1, 2016) can be mentioned. Also, as the ultraviolet absorber, the compounds described in paragraph numbers 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
Chemical formula
[0140] When containing an ultraviolet absorber, the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. In the present invention, only one kind of ultraviolet absorber may be used, or two or more kinds may be used. When two or more kinds are used, it is preferable that the total amount is within the above range.
[0141] <<Polymerization inhibitor>> The coloring composition of the present invention can contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine salts (ammonium salt, cerous salt, etc.). Among them, p-methoxyphenol is preferred. When containing a polymerization inhibitor, the content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass. The polymerization inhibitor may be only one type or two or more types. In the case of two or more types, the total amount is preferably within the above range.
[0142] <<Silane coupling agent>> The coloring composition of the present invention can contain a silane coupling agent. In the present invention, the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups. Further, the hydrolyzable group refers to a substituent directly bonded to a silicon atom and capable of forming a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group, etc., and an alkoxy group is preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, a phenyl group, etc., and an amino group, a (meth)acryloyl group and an epoxy group are preferred. Specific examples of the silane coupling agent include N-β-aminoethyl-γ-aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N-β-aminoethyl-γ-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N-β-aminoethyl-γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), γ-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-903), 3-methacryloxypropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-503), etc. Further, specific examples of the silane coupling agent include the compounds described in paragraph numbers 0018 to 0036 of JP-A-2009-288703 and the compounds described in paragraph numbers 0056 to 0066 of JP-A-2009-242604, and the contents of these are incorporated herein. When containing a silane coupling agent, the content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass. The silane coupling agent may be only one type or two or more types.In the case of two or more types, it is preferable that the total amount is within the above range.
[0143] <<Surfactant>> The coloring composition of the present invention can contain a surfactant. As the surfactant, various surfactants such as fluorosurfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants can be used. Examples of the surfactant include those described in paragraph numbers 0238 to 0245 of International Publication No. 2015 / 166779, and the contents thereof are incorporated herein.
[0144] The surfactant is preferably a fluorosurfactant. By including a fluorosurfactant in the coloring composition, the liquid properties (particularly, fluidity) can be further improved, and the liquid-saving property can be further improved. In addition, a film with less thickness unevenness can also be formed.
[0145] The fluorine content in the fluorosurfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. The fluorosurfactant having a fluorine content within this range is effective in terms of the uniformity of the thickness of the coating film and the liquid-saving property, and also has good solubility in the coloring composition.
[0146] Examples of the fluorosurfactant include surfactants described in paragraph numbers 0060 to 0064 of JP-A-2014-041318 (paragraph numbers 0060 to 0064 of corresponding International Publication No. 2014 / 017669), surfactants described in paragraph numbers 0117 to 0132 of JP-A-2011-132503, and the contents thereof are incorporated herein. Examples of commercially available fluorosurfactants include, for example, Megafac F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, EXP, MFS-330 (all manufactured by DIC Corporation), Fluorad FC430, FC431, FC171 (all manufactured by Sumitomo 3M Limited), Surflon S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, KH-40 (all manufactured by AGC Inc.), PolyFox PF636, PF656, PF6320, PF6520, PF7002 (all manufactured by OMNOVA Solutions Inc.), and the like.
[0147] In addition, as the fluorosurfactant, an acrylic compound having a molecular structure having a functional group containing a fluorine atom and capable of cleaving the portion of the functional group containing a fluorine atom and volatilizing the fluorine atom when heated can also be preferably used. Examples of such fluorosurfactants include the Megafac DS series manufactured by DIC Corporation (Chemical Industry Daily (February 22, 2016), Nikkei Industrial Newspaper (February 23, 2016)), for example, Megafac DS-21.
[0148] In addition, as the fluorosurfactant, it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound. Examples of such fluorosurfactants include the fluorosurfactants described in JP-A-2016-216602, and the contents thereof are incorporated herein.
[0149] A fluorosurfactant can also use a block polymer. As the fluorosurfactant, a fluorine-containing polymer compound containing a repeating unit derived from a (meth)acrylate compound having a fluorine atom and a repeating unit derived from a (meth)acrylate compound having two or more (preferably five or more) alkyleneoxy groups (preferably an ethyleneoxy group or a propyleneoxy group) can also be preferably used. Further, the fluorine-containing surfactants described in paragraph numbers 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorosurfactants used in the present invention.
Chemical formula
[0150] Further, as the fluorosurfactant, a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain can also be used. Specific examples include the compounds described in paragraph numbers 0050 to 0090 and paragraph numbers 0289 to 0295 of JP-A-2010-164965, Megafac RS-101, RS-102, RS-718K, RS-72-K, etc. manufactured by DIC Corporation. Further, as the fluorosurfactant, the compounds described in paragraph numbers 0015 to 0158 of JP-A-2015-117327 can also be used.
[0151] Examples of nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane, and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (manufactured by BASF), Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Lubrizol Japan Ltd.), NCW-101, NCW-1001, NCW-1002 (manufactured by Fujifilm Wako Pure Chemical Corporation), Pyonin D-6112, D-6112-W, D-6315 (manufactured by Takemoto Yushi Co., Ltd.), Orfin E1010, Surfynol 104, 400, 440 (manufactured by Nissin Chemical Industry Co., Ltd.), and the like.
[0152] Examples of silicone surfactants include, for example, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (all of the above are manufactured by Toray Dow Corning Co., Ltd.), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all of the above are manufactured by Momentive Performance Materials Inc.), KP-341, KF-6001, KF-6002 (all of the above are manufactured by Shin-Etsu Silicone Co., Ltd.), BYK307, BYK323, BYK330 (all of the above are manufactured by BYK-Chemie GmbH), and the like.
[0153] When containing a surfactant, the content of the surfactant in the total solid of the coloring composition is preferably 0.001% to 5.0% by mass, more preferably 0.005% to 3.0% by mass. The surfactant may be only one kind or two or more kinds. In the case of two or more kinds, the total amount is preferably within the above range.
[0154] <<Antioxidant>> The coloring composition of the present invention can contain an antioxidant. Examples of the antioxidant include phenolic compounds, phosphite ester compounds, thioether compounds, etc. As the phenolic compound, any phenolic compound known as a phenolic antioxidant can be used. Preferred phenolic compounds include hindered phenolic compounds. A compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferred. As the aforementioned substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred. Also, a compound having a phenolic group and a phosphite ester group in the same molecule is also preferred as the antioxidant. Also, a phosphorus-based antioxidant can be preferably used. The content of the antioxidant in the total solid of the coloring composition is preferably 0.01% to 20% by mass, more preferably 0.3% to 15% by mass. When containing an antioxidant, only one kind of antioxidant may be used, or two or more kinds may be used. In the case of using two or more kinds, the total amount is preferably within the above range.
[0155] <<Other components>> The coloring composition of the present invention may contain, as necessary, a sensitizer, a curing accelerator, a filler, a thermosetting accelerator, a plasticizer, and other auxiliary agents (for example, conductive particles, fillers, defoaming agents, flame retardants, leveling agents, peeling accelerators, fragrances, surface tension adjusters, chain transfer agents, etc.). By appropriately containing these components, properties such as film physical properties can be adjusted. These components can refer to, for example, the descriptions from paragraph number 0183 and onwards of JP-A-2012-003225 (paragraph number 0237 of the corresponding US Patent Application Publication No. 2013 / 0034812), the descriptions in paragraphs 0101 to 0104, 0107 to 0109, etc. of JP-A-2008-250074, and these contents are incorporated herein. Further, the coloring composition of the present invention may contain a latent antioxidant as necessary. As the latent antioxidant, a compound in which a site functioning as an antioxidant is protected by a protecting group, and the protecting group is eliminated by heating at 100 to 250 °C or heating at 80 to 200 °C in the presence of an acid / base catalyst to function as an antioxidant can be mentioned. Examples of the latent antioxidant include the compounds described in WO2014 / 021023, WO2017 / 030005, and JP-A-2017-008219. Commercially available products of the latent antioxidant include Adeka Arcles GPA-5001 (manufactured by ADEKA Corporation), etc. Further, as described in JP-A-2018-155881, C.I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
[0156] The coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film. Examples of the metal oxide include TiO2, ZrO2, Al2O3, SiO2, etc. The primary particle diameter of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm. The metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
[0157] The coloring composition of the present invention may contain a light resistance improver. Examples of the light resistance improver include the compounds described in paragraph numbers 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraph numbers 0029 to 0034 of JP-A-2017-146350, the compounds described in paragraph numbers 0036 to 0037 and 0049 to 0052 of JP-A-2017-129774, the compounds described in paragraph numbers 0031 to 0034 and 0058 to 0059 of JP-A-2017-129674, the compounds described in paragraph numbers 0036 to 0037 and 0051 to 0054 of JP-A-2017-122803, the compounds described in paragraph numbers 0025 to 0039 of International Publication No. 2017 / 164127, the compounds described in paragraph numbers 0034 to 0047 of JP-A-2017-186546, the compounds described in paragraph numbers 0019 to 0041 of JP-A-2015-025116, the compounds described in paragraph numbers 0101 to 0125 of JP-A-2012-145604, the compounds described in paragraph numbers 0018 to 0021 of JP-A-2012-103475, the compounds described in paragraph numbers 0015 to 0018 of JP-A-2011-257591, the compounds described in paragraph numbers 0017 to 0021 of JP-A-2011-191483, the compounds described in paragraph numbers 0108 to 0116 of JP-A-2011-145668, the compounds described in paragraph numbers 0103 to 0153 of JP-A-2011-253174, and the like.
[0158] The water content of the coloring composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably in the range of 0.1 to 1.0% by mass. The water content can be measured by the Karl Fischer method.
[0159] The coloring composition of the present invention can be used after adjusting the viscosity for the purpose of adjusting the film surface state (such as flatness) and the film thickness. The value of the viscosity can be appropriately selected as needed. For example, at 25°C, it is preferably 0.3 mPa·s to 50 mPa·s, and more preferably 0.5 mPa·s to 20 mPa·s. As a method for measuring the viscosity, for example, a cone plate type viscometer can be used and measured in a state where the temperature is adjusted to 25°C.
[0160] As the container for housing the coloring composition of the present invention, there is no particular limitation, and known containers can be used. Further, as the container, in order to suppress the mixing of impurities into the raw materials and the composition, it is also preferable to use a multilayer bottle having an inner wall of the container composed of six types of resins in six layers or a bottle having a seven-layer structure of six types of resins. Examples of such containers include the containers described in JP-A-2015-123351.
[0161] <Method for preparing the coloring composition> The coloring composition of the present invention can be prepared by mixing the aforementioned components. When preparing the coloring composition, all the components may be simultaneously dissolved and / or dispersed in a solvent to prepare the coloring composition, or, if necessary, each component may be appropriately prepared as two or more solutions or dispersions and these may be mixed at the time of use (coating) to prepare the coloring composition.
[0162] In addition, when preparing the coloring composition, it is preferable to include a process of dispersing the pigment. In the process of dispersing the pigment, examples of the mechanical force used for dispersing the pigment include compression, squeezing, impact, shear, cavitation, etc. Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high-speed impellers, sand grinders, flow jet mixers, high-pressure wet atomization, ultrasonic dispersion, etc. In addition, in the grinding of the pigment in a sand mill (bead mill), it is preferable to perform the treatment under conditions where the grinding efficiency is increased by using beads with a small diameter and increasing the filling rate of the beads. Further, it is preferable to remove coarse particles by filtration, centrifugation, etc. after the grinding treatment. In addition, the process and disperser for dispersing the pigment can preferably use the processes and dispersers described in "Complete Collection of Dispersion Technologies, published by Information Organization, Ltd., July 15, 2005", "Practical Comprehensive Data Collection of Dispersion Technologies and Industrial Applications Focusing on Suspensions (Solid / Liquid Dispersion Systems), published by the Publishing Department of the Management Development Center, October 10, 1978", and paragraph number 0022 of Japanese Patent Application Laid-Open No. 2015-157893. In addition, in the process of dispersing the pigment, the particle size reduction treatment may be performed in the salt milling step. For the materials, equipment, treatment conditions, etc. used in the salt milling step, for example, the descriptions in Japanese Patent Application Laid-Open No. 2015-194521 and Japanese Patent Application Laid-Open No. 2012-046629 can be referred to.
[0163] In the preparation of the coloring composition, for the purposes of removing foreign matters and reducing defects, etc., it is preferable to filter the coloring composition with a filter. As the filter, any filter that has been conventionally used for filtration purposes, etc. can be used without particular limitation. For example, filters made of materials such as fluororesins such as polytetrafluoroethylene (PTFE), polyamide resins such as nylon (for example, nylon-6, nylon-6,6), and polyolefin resins such as polyethylene and polypropylene (PP) (including high-density and ultra-high molecular weight polyolefin resins) can be mentioned. Among these materials, polypropylene (including high-density polypropylene) and nylon are preferable.
[0164] The pore diameter of the filter is preferably from 0.01 to 7.0 μm, more preferably from 0.01 to 3.0 μm, and even more preferably from 0.05 to 0.5 μm. If the pore diameter of the filter is within the above range, fine foreign matters can be removed more reliably. Regarding the pore diameter value of the filter, the nominal value of the filter manufacturer can be referred to. As the filter, various filters provided by Nippon Pole Co., Ltd. (such as DFA4201NIEY), Advantec Toyo Co., Ltd., Nippon Integris Co., Ltd. (former Nippon Microlith Co., Ltd.), and Kits Microfilter Co., Ltd. can be used.
[0165] Also, it is preferable to use a fibrous filter medium as the filter. Examples of the fibrous filter medium include polypropylene fiber, nylon fiber, and glass fiber. Commercially available products include the SBP type series (such as SBP008), TPR type series (such as TPR002 and TPR005), and SHPX type series (such as SHPX003) manufactured by Rocktechno Co., Ltd. When using the filter, different filters (for example, the first filter and the second filter, etc.) may be combined. In that case, the filtration with each filter may be performed only once or may be performed two or more times. Also, filters with different pore diameters may be combined within the above-mentioned range. Also, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing other components, the filtration may be performed with the second filter.
[0166] <Film> The film of the present invention is a film obtained from the above-described coloring composition of the present invention. The film of the present invention can be used for optical filters such as color filters and infrared transmission filters.
[0167] The film thickness of the film of the present invention can be appropriately adjusted according to the purpose. For example, the film thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.
[0168] When the film of the present invention is used as a color filter, the film of the present invention preferably has a hue of green, red, blue, cyan, magenta or yellow, and more preferably has a hue of green, red or yellow. Further, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of the colored pixel include a red pixel, a green pixel, a blue pixel, a magenta pixel, a cyan pixel, and a yellow pixel. Among them, a red pixel, a green pixel, and a yellow pixel are preferable, a red pixel or a green pixel is more preferable, and a green pixel is still more preferable.
[0169] Further, it is preferable that the wavelength at which the light transmittance of the film of the present invention becomes 50% exists in the wavelength range of 470 to 520 nm, more preferably exists in the wavelength range of 475 to 520 nm, and still more preferably exists in the wavelength range of 480 to 520 nm. In particular, it is preferable that the wavelength at which the light transmittance becomes 50% exists in each of the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this aspect, the wavelength on the short wavelength side at which the light transmittance becomes 50% preferably exists in the wavelength range of 475 to 520 nm, and more preferably exists in the wavelength range of 480 to 520 nm. Further, the wavelength on the long wavelength side at which the light transmittance becomes 50% preferably exists in the wavelength range of 580 to 620 nm, and more preferably exists in the wavelength range of 585 to 615 nm. A film having such spectral characteristics is preferably used as a green pixel.
[0170] When the film of the present invention is used as an infrared transmission filter, the film of the present invention preferably has any one of the following spectral characteristics (1) to (4). (1): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the light transmittance in the thickness direction of the film in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more). A film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light having a wavelength exceeding 700 nm. (2): A film in which the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the light transmittance in the film thickness direction in the wavelength range of 900 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more). A film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light with a wavelength exceeding 850 nm. (3): A film in which the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the light transmittance in the film thickness direction in the wavelength range of 1000 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more). A film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light with a wavelength exceeding 940 nm. (4): A film in which the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the light transmittance in the film thickness direction in the wavelength range of 1100 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more). A film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light with a wavelength exceeding 1040 nm.
[0171] <Method for manufacturing the film> Next, the method for manufacturing the film of the present invention will be described. The film of the present invention can be manufactured through the step of applying the coloring composition of the present invention. In the method for manufacturing the film, it is preferably further included a step of forming a pattern (pixel). Examples of the method for forming the pattern (pixel) include a photolithography method and a dry etching method, and the photolithography method is preferred.
[0172] Pattern formation by photolithography preferably includes a step of forming a colored composition layer on a support using the colored composition of the present invention, a step of exposing the colored composition layer in a pattern, and a step of developing and removing the unexposed portion of the colored composition layer to form a pattern (pixel). If necessary, a step of baking the colored composition layer (pre-baking step) and a step of baking the developed pattern (pixel) (post-baking step) may be provided.
[0173] In the step of forming the colored composition layer, a colored composition layer is formed on a support using the colored composition of the present invention. The support is not particularly limited and can be appropriately selected according to the application. For example, a glass substrate, a silicon substrate, etc. may be mentioned, and a silicon substrate is preferred. Further, a charge-coupled device (CCD), a complementary metal-oxide semiconductor (CMOS), a transparent conductive film, etc. may be formed on the silicon substrate. Further, a black matrix for isolating each pixel may be formed on the silicon substrate. Further, a base layer may be provided on the silicon substrate for improving adhesion to the upper layer, preventing diffusion of substances, or flattening the substrate surface. The base layer may be formed using a composition obtained by removing a colorant from the colored composition described in this specification, a composition containing a curable compound, a surfactant, etc. described in this specification. The surface contact angle of the base layer is preferably 20 to 70° when measured with diiodomethane. Further, it is preferably 30 to 80° when measured with water. If the surface contact angle of the base layer is within the above range, the coatability of the resin composition is good. The adjustment of the surface contact angle of the base layer can be performed by a method such as adding a surfactant.
[0174] As a method for applying the coloring composition, known methods can be used. For example, the drop casting method; the slit coating method; the spray method; the roll coating method; the spin coating method; the casting coating method; the slit and spin method; the dip coating method (for example, the method described in JP-A-2009-145395); ejection system printing such as inkjet (for example, on-demand type, piezo type, thermal type), nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing method, and other various printing methods; a transfer method using a mold or the like; a nanoimprint method, etc. The application method in inkjet is not particularly limited, and for example, the method shown in "Spreadable and Usable Inkjet - Infinite Possibilities in Patents - Published in February 2005, Sumitomo Precision Products Co., Ltd." (particularly pages 115 to 133), and the methods described in JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, etc. can be mentioned. Further, regarding the method for applying the coloring composition, the descriptions of WO 2017 / 030174 and WO 2017 / 018419 can be referred to, and the contents thereof are incorporated herein.
[0175] The coloring composition layer formed on the support may be dried (pre-baked). When manufacturing a film by a low-temperature process, pre-baking may not be necessary. When pre-baking is performed, the pre-baking temperature is preferably 150°C or lower, more preferably 120°C or lower, and even more preferably 110°C or lower. The lower limit can be, for example, 50°C or higher, and can also be 80°C or higher. The pre-baking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Pre-baking can be performed on a hot plate, in an oven, or the like.
[0176] Next, the colored composition layer is exposed in a pattern (exposure step). For example, the colored composition layer can be exposed in a pattern by exposing it through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. Thereby, the exposed portion can be cured.
[0177] Examples of the radiation (light) that can be used for exposure include g-line, i-line, etc. Also, light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can be used. Examples of light with a wavelength of 300 nm or less include KrF line (wavelength 248 nm), ArF line (wavelength 193 nm), etc., and KrF line (wavelength 248 nm) is preferred. Also, light sources with longer wavelengths of 300 nm or more can be used.
[0178] Also, at the time of exposure, the light may be continuously irradiated for exposure, or may be irradiated pulsatively for exposure (pulse exposure). Note that pulse exposure is an exposure method in which light irradiation and pause are repeated in a short time cycle (for example, at the millisecond level or less) for exposure.
[0179] The irradiation amount (exposure amount) is, for example, preferably 0.03 to 2.5 J / cm 2 and more preferably 0.05 to 1.0 J / cm 2 The oxygen concentration during exposure can be appropriately selected. In addition to performing it in the atmosphere, for example, it may be exposed in a low oxygen atmosphere with an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially oxygen-free), or in a high oxygen atmosphere with an oxygen concentration exceeding 21% by volume (for example, 22% by volume, 30% by volume, or 50% by volume). Also, the exposure illuminance can be appropriately set, and is usually 1000 W / m 2 ~100000 W / m 2 (for example, 5000 W / m 2 , 15000 W / m 2 , or 35000 W / m 2 ) and can be selected from the range. The oxygen concentration and the exposure illuminance can be appropriately combined. For example, an oxygen concentration of 10% by volume and an illuminance of 10000 W / m 2, an oxygen concentration of 35% by volume and an illuminance of 20000 W / m 2 and the like can be used.
[0180] Next, the unexposed portion of the colored composition layer is developed and removed to form a pattern (pixel). The development and removal of the unexposed portion of the colored composition layer can be performed using a developer. As a result, the unexposed portion of the colored composition layer in the exposure step is eluted in the developer, and only the photocured portion remains. The temperature of the developer is preferably, for example, 20 to 30°C. The development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the developer may be shaken off every 60 seconds, and the step of supplying a new developer may be repeated several times.
[0181] The developing solution includes organic solvents, alkaline developing solutions, etc., and an alkaline developing solution is preferably used. As the alkaline developing solution, an alkaline aqueous solution (alkaline developing solution) obtained by diluting an alkaline agent with pure water is preferred. Examples of the alkaline agent include organic alkaline compounds such as ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis(2-hydroxyethyl)ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo-[5.4.0]-7-undecene, and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, sodium silicate, and sodium metasilicate. Alkaline agents with larger molecular weights are preferred in terms of environmental and safety aspects. The concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass. Further, the developing solution may further contain a surfactant. From the viewpoints of convenience in transportation and storage, etc., the developing solution may be once manufactured as a concentrated solution and diluted to the required concentration at the time of use. The dilution ratio is not particularly limited, but can be set, for example, in the range of 1.5 to 100 times. Also, it is preferable to wash (rinse) with pure water after development. Further, the rinsing is preferably performed by supplying a rinse solution to the colored composition layer after development while rotating the support on which the colored composition layer after development is formed. Also, it is preferable to move the nozzle for discharging the rinse solution from the central part of the support to the peripheral part of the support. At this time, when moving the nozzle from the central part to the peripheral part of the support, the moving speed of the nozzle may be gradually decreased while moving. By performing rinsing in this way, the in-plane variation of the rinsing can be suppressed. Also, the same effect can be obtained by gradually decreasing the rotation speed of the support while moving the nozzle from the central part to the peripheral part of the support.
[0182] After development, it is preferable to perform additional exposure treatment or heat treatment (post-baking) after drying. The additional exposure treatment and post-baking are post-development curing treatments for making the curing complete. The heating temperature in post-baking is preferably, for example, 100 to 240 °C, more preferably 200 to 240 °C. Post-baking can be carried out continuously or batchwise using heating means such as a hot plate, a convection oven (hot air circulation dryer), a high-frequency heater, etc. so that the film after development becomes the above conditions. When performing the additional exposure treatment, the light used for exposure is preferably light with a wavelength of 400 nm or less. Also, the additional exposure treatment may be carried out by the method described in Korean Patent Publication No. 10-2017-0122130.
[0183] For pattern formation by the dry etching method, a step of forming a colored composition layer on a support using the colored composition of the present invention and curing the entire colored composition layer to form a cured product layer, a step of forming a photoresist layer on this cured product layer, a step of exposing the photoresist layer in a pattern and then developing it to form a resist pattern, and a step of dry etching the cured product layer using an etching gas with this resist pattern as a mask are preferably included. In the formation of the photoresist layer, it is preferable to further perform a pre-baking treatment. In particular, as the photoresist layer formation process, a form in which heat treatment after exposure and heat treatment after development (post-baking treatment) are carried out is desirable. Regarding pattern formation by the dry etching method, the descriptions in paragraphs 0010 to 0067 of JP-A-2013-064993 can be referred to, and this content is incorporated herein.
[0184] <Optical Filter> The optical filter of the present invention has the film of the present invention described above. Examples of the type of optical filter include a color filter and an infrared transmission filter, and it is preferably a color filter. As the color filter, it is preferable to have the film of the present invention as the colored pixel of the color filter.
[0185] The optical filter may have a protective layer provided on the surface of the film of the present invention. By providing the protective layer, various functions such as oxygen barrier, antireflection, hydrophilic / hydrophobic modification, and shielding of light of specific wavelengths (ultraviolet rays, near-infrared rays, etc.) can be imparted. The thickness of the protective layer is preferably 0.01 to 10 μm, more preferably 0.1 to 5 μm. Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of attaching a molded resin with an adhesive. Examples of the components constituting the protective layer include (meth)acrylic resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluororesin, polycarbonate resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al2O3, Mo, SiO2, Si2N4, etc. Two or more of these components may be contained. For example, in the case of a protective layer for the purpose of oxygen barrier, the protective layer preferably contains a polyol resin, SiO2, and Si2N4. Also, in the case of a protective layer for the purpose of antireflection, the protective layer preferably contains a (meth)acrylic resin and a fluororesin.
[0186] When forming the protective layer by applying a resin composition, known methods such as spin coating, casting, screen printing, and inkjet can be used as the application method of the resin composition. Known organic solvents (for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.) can be used as the organic solvent contained in the resin composition. When forming the protective layer by chemical vapor deposition, known chemical vapor deposition methods (thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition) can be used as the chemical vapor deposition method.
[0187] The protective layer may contain additives such as organic and inorganic fine particles, absorbents for light of specific wavelengths (e.g., ultraviolet rays, near-infrared rays, etc.), refractive index adjusters, antioxidants, adhesives, surfactants, etc., if necessary. Examples of the organic and inorganic fine particles include, for example, polymer fine particles (e.g., silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, oxynitride titanium, magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate, etc. Known absorbents can be used as the absorbent for light of specific wavelengths. The content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer.
[0188] Also, as the protective layer, the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
[0189] The optical filter may have a structure in which each pixel is embedded in a space partitioned, for example, in a lattice shape by a partition wall.
[0190] <Solid-state imaging device> The solid-state imaging device of the present invention has the film of the present invention described above. The configuration of the solid-state imaging device is not particularly limited as long as it includes the film of the present invention and functions as a solid-state imaging device. For example, the following configurations can be mentioned.
[0191] On a substrate, there are a plurality of photodiodes constituting a light-receiving area of a solid-state imaging device (such as a CCD (charge-coupled device) image sensor, a CMOS (complementary metal-oxide semiconductor) image sensor, etc.) and transfer electrodes made of polysilicon or the like. There is a light-shielding film with an opening only in the light-receiving part of the photodiode on the photodiode and the transfer electrodes. On the light-shielding film, there is a device protection film made of silicon nitride or the like formed to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. On the device protection film, there is a configuration having a color filter. Further, it may be a configuration having condensing means (for example, a microlens or the like. The same applies hereinafter) on the device protection film and below the color filter (the side closer to the substrate), or a configuration having condensing means on the color filter. Also, the color filter may have a structure in which each colored pixel is embedded in a space partitioned, for example, in a lattice shape by partition walls. In this case, it is preferable that the partition walls have a low refractive index with respect to each colored pixel. Examples of such an imaging device having such a structure include the devices described in JP-A-2012-227478, JP-A-2014-179577, and International Publication No. 2018 / 043654. Also, as shown in JP-A-2019-211559, an ultraviolet absorption layer may be provided in the structure of the solid-state imaging device to improve light resistance. The imaging device provided with the solid-state imaging device of the present invention can be used not only for a digital camera and an electronic device having an imaging function (such as a mobile phone), but also for an in-vehicle camera and a surveillance camera.
[0192] <Image display device> The image display device of the present invention has the film of the present invention described above. Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device. For the definition of the image display device and the details of each image display device, refer to, for example, "Electronic Display Device (written by Akio Sasaki, published by Kogyo Chosa Kai, Inc. in 1990)", "Display Device (written by Junsho Ibuki, published by Sangyo Tosho Co., Ltd. in 1990)", etc. Also, for liquid crystal display devices, refer to, for example, "Next-generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Chosa Kai, Inc. in 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied, and it can be applied to various types of liquid crystal display devices described in the above "Next-generation Liquid Crystal Display Technology", for example.
Example
[0193] The present invention will be described more specifically with reference to the following examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be appropriately changed as long as they do not depart from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below.
[0194] <Production of Dispersion Liquid> A mixed solution obtained by mixing the raw materials described in the following table was mixed and dispersed for 3 hours using a bead mill (zirconia beads with a diameter of 0.1 mm). Then, under the conditions of a pressure of 2000 kg / cm 3 and a flow rate of 500 g / min, a dispersion treatment was performed. This dispersion treatment was repeated a total of 10 times to obtain a dispersion liquid. The numerical values indicating the compounding amounts described in the following table are in parts by mass. The content of the yellow colorant in the colorant (yellow colorant ratio in the table) and the content of the azomethine metal complex in the yellow colorant (azomethine metal complex ratio in the table) are also shown in the following table.
[0195]
Table 1
[0196]
Table 2
[0197]
Table 3
[0198]
Table 4
[0199]
Table 5
[0200] The raw materials described by the abbreviations in the above table are as follows.
[0201] (Green colorant) PG36: C.I. Pigment Green 36 (phthalocyanine compound, green pigment) PG58: C.I. Pigment Green 58 (phthalocyanine compound, green pigment) PG62: C.I. Pigment Green 62 (phthalocyanine compound, green pigment)
[0202] (Red colorant) PR254: C.I. Pigment Red 254 (diketopyrrolopyrrole compound, red pigment) PR264: C.I. Pigment Red 264 (diketopyrrolopyrrole compound, red pigment) PR272: C.I. Pigment Red 272 (diketopyrrolopyrrole compound, red pigment)
[0203] (Yellow colorant) Azomethine metal complex 1: C.I. Pigment Yellow 129 (azomethine copper complex, compound with the following structure, yellow pigment)
Chemical formula
[0204] PY138: C.I. Pigment Yellow 138 (quinophthalone compound, yellow pigment) PY139: C.I. Pigment Yellow 139 (isoindoline compound, yellow pigment) PY150: C.I. Pigment Yellow 150 (azo compound, yellow pigment) PY185: C.I. Pigment Yellow 185 (isoindoline compound, yellow pigment) PY215: C.I. Pigment Yellow 215 (pteridine compound, yellow pigment)
[0205] (Pigment derivative) Pigment derivative 1: A compound with the following structure [Chemical formula]
[0206] (Dispersant) B-1: A resin with the following structure (propylene glycol monomethyl ether acetate (PGMEA) solution with a solid content concentration of 30%, the numerical values attached to the main chain are mass ratios, and the numerical values attached to the side chain are the number of repeating units. Weight average molecular weight = 13000, acid value 65 mg KOH / g) [Chemical formula] B-2: A resin solution of resin B-2 synthesized by the following method (PGMEA solution with a solid content concentration of 30% by mass). 50 parts by mass of methyl methacrylate, 30 parts by mass of n-butyl methacrylate, 20 parts by mass of t-butyl methacrylate, and 45.4 parts by mass of PGMEA were charged into a reaction vessel, and the atmosphere gas was replaced with nitrogen gas. The inside of the reaction vessel was heated to 70 °C, 6 parts by mass of 3-mercapto-1,2-propanediol was added, and further 0.12 parts by mass of AIBN (azobisisobutyronitrile) was added, followed by reacting for 12 hours. It was confirmed by solid content measurement that 95% had reacted. Next, 9.7 parts by mass of pyromellitic dianhydride, 70.3 parts by mass of PGMEA, and 0.20 parts by mass of DBU (1,8-diazabicyclo-[5.4.0]-7-undecene) as a catalyst were added, and the reaction was carried out at 120 °C for 7 hours. It was confirmed by acid value measurement that 98% or more of the acid anhydride was half-esterified, and the reaction was terminated. PGMEA was added to adjust the non-volatile content (solid content concentration) to 30% by mass, and a resin solution of resin B-2 having an acid value of 43 mgKOH / g and a weight average molecular weight of 9000 with the following structure was obtained.
Chemical formula
Chemical formula
[0207] (Solvent) Solvent 1: Propylene glycol monomethyl ether acetate (PGMEA)
[0208] <Production of colored composition> The raw materials described in the following table were mixed to produce a colored composition.
[0209]
Table 6
[0210]
Table 7
[0211]
Table 8
[0212]
Table 9
[0213]
Table 10
[0214] The raw materials described by the abbreviations in the above table are as follows.
[0215] (Dispersion liquid) Dispersion liquids 1 to 35, c1: the above-described dispersion liquids 1 to 35, c1
[0216] (Resin) Resin 1: 40 mass% PGMEA solution of the resin having the following structure (the numerical values attached to the main chain are molar ratios. Weight average molecular weight = 11000)
Chemical formula
[0217] Resin 2: 70.0 parts by mass of cyclohexanone was charged into a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube, and a stirring device, and the temperature was raised to 80 °C. After purging the inside of the flask with nitrogen, a mixture of 13.3 parts by mass of n-butyl methacrylate, 4.6 parts by mass of 2-hydroxyethyl methacrylate, 4.3 parts by mass of methacrylic acid, 7.4 parts by mass of para-cumylphenol ethylene oxide-modified acrylate (manufactured by Toagosei Co., Ltd., Aronix M110), and 0.4 parts by mass of 2,2'-azobisisobutyronitrile was dropped from the dropping tube over 2 hours. After completion of the dropping, the reaction was carried out for 3 hours to obtain Resin P2. PGMEA was added to adjust the solid content concentration to 30% by mass to obtain a resin solution (30% by mass PGMEA solution of Resin P2). The weight average molecular weight of Resin P2 was 26,000. This resin solution was used as Resin 2.
[0218] (Polymerizable compound) Polymerizable compound 1: A compound having the following structure [Chemical formula] Polymerizable compound 2: A mixture of compounds having the following structures (a mixture of the left compound (a 6-functional (meth)acrylate compound) and the right compound (a 5-functional (meth)acrylate compound) in a molar ratio of 7:3) [Chemical formula]
[0219] (Photoinitiator) Photoinitiator 1: A compound having the following structure [Chemical formula] Photoinitiator 2: A compound having the following structure [Chemical formula] Photoinitiator 3: A compound having the following structure [Chemical formula]
[0220] (Surfactant) Surfactant 1: 1 mass% PGMEA solution of the following mixture (weight average molecular weight = 14000). In the following formula, the % indicating the ratio of the repeating unit is mass%.
Chem.
[0221] (Silane coupling agent) Silane coupling agent 1: 0.2 mass% PGMEA solution of the compound with the following structure (weight average molecular weight = 3000)
Chem.
[0222] (Epoxy compound) Epoxy compound 1: EHPE3150 (manufactured by Daicel Corporation)
[0223] (Solvent) Solvent 1: PGMEA Solvent 2: Cyclohexanone
[0224] (Performance evaluation of the coloring composition) [Long-term reliability evaluation] After the coloring composition described in the above table was spin-coated on an 8-inch (20.32 cm) glass wafer to a thickness of 0.65 μm after post-baking, it was heated on a hot plate at 100 °C for 2 minutes to form a coloring composition layer. Then, using an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.), through a mask having a Bayer pattern, 300 mJ / cm 2The coloring composition layer was exposed with the exposure amount described above. Subsequently, paddle development was performed on the coloring composition layer at 23 °C for 60 seconds using a 0.3 mass% aqueous solution of tetramethylammonium hydroxide (TMAH). Thereafter, rinsing by spin shower and water washing using pure water were carried out, and further, heating (post-baking) was performed at 200 °C for 5 minutes using a hot plate to form the first pixel on the glass wafer. Subsequently, a radiation-sensitive composition described in paragraph number 0231 of JP-A-2013-254047 was used, and development and exposure were performed in the same manner as for the formation of the first pixel, and a second pixel (transparent pixel) was formed in the missing portion of the Bayer pattern of the first pixel on the glass wafer. Using a microscopic spectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.), the transmittance (initial spectroscopy) of light with a wavelength of 400 to 700 nm of the second pixel was measured. Next, after performing a reliability test by leaving the glass wafers on which the first pixel and the second pixel were respectively formed stationary for 1500 hours under the conditions of a temperature of 85 °C and a relative humidity of 85%, using a microscopic spectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.), the transmittance (spectroscopy after the reliability test) of light with a wavelength of 400 to 700 nm of the second pixel at a position 2 μm away from the boundary with the first pixel was measured. The change amount of the transmittance of light with a wavelength of 400 to 700 nm of the second pixel before and after the test (= |transmittance (%) of the second pixel before the reliability test - transmittance (%) of the second pixel after the reliability test|) was calculated, and the maximum value (ΔT max1 ) was obtained, and the long-term reliability was evaluated according to the following criteria. The smaller the value of ΔT max1 , the better the long-term reliability. 5: ΔT max1 is 0.5% or less 4: ΔT max1 is greater than 0.5% and 1% or less 3: ΔT max1 is greater than 1% and 3% or less 2: ΔT max1 is greater than 3% and 5% or less 1: ΔT max1 is greater than 5%
[0225] [Light resistance evaluation] The coloring composition described in the above table was spin-coated onto an 8-inch (20.32 cm) glass wafer to a thickness of 0.65 μm after post-baking, and then heated on a hot plate at 100 °C for 2 minutes to form a coloring composition layer. Next, using an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.), the coloring composition layer was exposed at an exposure dose of 300 mJ / cm 2 . Subsequently, a 0.3 mass% aqueous solution of tetramethylammonium hydroxide (TMAH) was used to perform paddle development on the composition layer at 23 °C for 60 seconds. Thereafter, rinsing with a spin shower and washing with pure water were carried out, and further, heating (post-baking) was performed on a hot plate at 200 °C for 5 minutes to form a film. The transmittance of the obtained film was measured using an MCPD3700 (manufactured by Otsuka Electronics Co., Ltd.). For the above film, a light resistance test was conducted by irradiating light at an illuminance of 100,000 lux for 1500 hours using a super xenon weather meter SX75 (manufactured by Suga Test Instruments Co., Ltd.). The transmittance of the film after the light resistance test was measured using an MCPD3700 (manufactured by Otsuka Electronics Co., Ltd.). The change amount of the transmittance of light with wavelengths from 400 to 700 nm of the film before and after the test (= |transmittance of the film before the light resistance test (%) - transmittance of the film after the light resistance test (%)|) was calculated, and the maximum value (ΔT max2 ) was obtained, and the light resistance was evaluated according to the following criteria. The smaller the value of ΔT max2 , the better the light resistance. 5: ΔT max2 is 5% or less 4: ΔT max2 is greater than 5% and 10% or less 3: ΔT max2 is greater than 10% and 20% or less 2: ΔT max2 is greater than 20% and 25% or less 1: ΔT max2 is greater than 25% and 30% or less 0: ΔT max2 is greater than 30%
[0226] The evaluation results of long-term reliability and light resistance are shown in the following table. The content of the yellow colorant in the colorants used in each coloring composition (the yellow colorant ratio in the table) and the content of the azomethine metal complex in the yellow colorant (the azomethine metal complex ratio in the table) are also shown. Further, after the coloring compositions of Examples 1 to 28 and 32 to 40 were applied on an 8-inch (20.32 cm) glass wafer by spin coating, they were heated at 100 °C for 2 minutes using a hot plate, and then heated at 200 °C for 5 minutes. For the film with a thickness of 0.65 μm thus formed, the transmittance of light with a wavelength of 470 to 520 nm was measured, and the value of the wavelength at which the transmittance becomes 50% was recorded in the column of "Transmittance 50% Wavelength (nm)" in the following table.
[0227]
Table 11
[0228]
Table 12
[0229]
Table 13
[0230]
Table 14
[0231]
Table 15
[0232] As shown in the above table, the coloring compositions of the examples were able to form films with excellent long-term reliability.
[0233] (Example 1001) A green coloring composition was spin-coated onto a silicon wafer so that the film thickness after film formation was 1.0 μm. Then, it was heated at 100 °C for 2 minutes using a hot plate. Next, using an i-line stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.), it was exposed through a mask of a 2-μm square dot pattern with an exposure dose of 1000 mJ / cm 2 Then, paddle development was performed at 23 °C for 60 seconds using a 0.3 mass% aqueous solution of tetramethylammonium hydroxide (TMAH). Thereafter, rinsing was performed with a spin shower, and further washing was performed with pure water. Next, by heating at 200 °C for 5 minutes using a hot plate, the green coloring composition was patterned to form green pixels. Similarly, the red coloring composition and the blue coloring composition were patterned by the same process to sequentially form red pixels and blue pixels, thereby forming a color filter having green pixels, red pixels, and blue pixels. In this color filter, the green pixels were formed in a Bayer pattern, and red pixels and blue pixels were formed in an island pattern in adjacent regions. The obtained color filter was incorporated into a solid-state imaging device according to a known method. This solid-state imaging device had a suitable image recognition ability. Note that, as the green coloring composition, the coloring composition of Example 2 was used. As the red coloring composition, the coloring composition of Example 29 was used. The blue coloring composition will be described later.
[0234] (Adjustment of Blue Coloring Composition) The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pall Co., Ltd.) with a pore diameter of 0.45 μm to prepare a blue coloring composition. Blue Pigment Dispersion: 30.47 parts by mass Dye 1: 2.64 parts by mass Resin 1: 0.01 part by mass Resin 3: 0.04 part by mass Polymerizable Compound 3: 1.56 parts by mass Photoinitiator 4: 0.57 part by mass Additive 1: 0.35 part by mass Epoxy Compound 2: 0.46 part by mass Surfactant 101: 2.00 parts by mass (as a 1 mass% PGMEA solution) PGMEA: 5.70 parts by mass Cyclohexanone: 55.4 parts by mass Propylene glycol monomethyl ether: 0.8 parts by mass
[0235] The raw materials used in the preparation of the blue coloring composition are as follows.
[0236] · Blue pigment dispersion A mixed solution consisting of 15 parts by mass of C.I. Pigment Blue 15:6, 2.2 parts by mass of a dispersant (Disperbyk-161, manufactured by BYK Chemie), 32.2 parts by mass of a resin, and 80.6 parts by mass of a solvent was mixed and dispersed for 3 hours using a bead mill (zirconia beads with a diameter of 0.3 mm). Then, using a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE International Co., Ltd.) equipped with a decompression mechanism, dispersion treatment was performed at a pressure of 2000 kg / cm 2 and a flow rate of 500 g / min. This dispersion treatment was repeated 10 times to obtain a blue pigment dispersion.
[0237] · Dye 1: A xanthene dye polymer represented by the following formula (weight average molecular weight: 7,400, acid value: 0.8 mmol / g, C=C bond equivalent: 0.78 mmol / g, in the following structural formula, iPr is an isopropyl group)
Chemical formula
[0238] · Resin 1: A 40% PGMEA solution of a resin having the following structure (the numerical values attached to the main chain are molar ratios. Weight average molecular weight = 11000)
Chemical formula
[0239] · Resin 3: A resin having the following structure (the numerical values attached to the main chain are molar ratios. Weight average molecular weight = 11000, acid value = 200 mgKOH / g)
Chemical formula
Chem.
Chem.
Chem.
Chem.
Chem.
Claims
1. A colored composition comprising a colorant containing a yellow colorant, a resin, and a solvent, wherein the content of the yellow colorant in the colorant is 30% by mass or more, the yellow colorant contains 15% by mass or more of an azomethine metal complex, and the azomethine metal complex is a copper azomethine complex, the yellow colorant further contains a yellow colorant other than the azomethine metal complex, and the yellow colorant other than the azomethine metal complex is at least one selected from an azo compound, an isoindoline compound, and a pteridine compound, the yellow colorant substantially does not contain a quinophthalone compound, the resin contains a graft resin, Colored composition.
2. The colored composition according to claim 1, wherein the colorant contains at least one selected from a green colorant and a red colorant.
3. The colored composition according to claim 1, wherein the colorant contains a green colorant, and the green colorant contains a phthalocyanine compound.
4. The colored composition according to any one of claims 1 to 3, wherein the yellow colorant other than the azomethine metal complex contains an azo metal complex.
5. When a film having a thickness of 0.65 μm is formed using the colored composition, the wavelength at which the light transmittance of the film becomes 50% is in the wavelength range of 470 to 520 nm. The colored composition according to any one of claims 1 to 4.
6. The colored composition according to any one of claims 1 to 5, further comprising a polymerizable compound and a photopolymerization initiator.
7. The colored composition according to any one of claims 1 to 6, which is for a color filter or an infrared transmission filter.
8. A film obtained from the colored composition according to any one of claims 1 to 7.
9. An optical filter having the film according to claim 8.
10. A solid-state imaging device having the film according to claim 8.
11. An image display device having the film according to claim 8.
Citation Information
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