Coloring composition, film, optical filter, solid-state imaging element, and image display device
By using a coloring composition containing compound S-1 with aromatic rings and azomethyl alkali structure in the color filter film, the existing color filter film has solved the problem of insufficient heat resistance and defects after heating, and achieved resistance to the color filter film The film effect is excellent in thermal properties and few defects.
Patent Information
- Application Number
- CN202180029552.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-04-23
- Filing Date
- 2021-03-10
- Publication Date
- 2024-12-31
- Estimated Expiration
- 2041-03-10
AI Technical Summary
The conventional color filter film has insufficient heat resistance after heating and is prone to large fluctuations in spectroscopic characteristics, and has defect problems, making it difficult to effectively suppress the generation of condensed materials.
A coloring composition containing compound S-1, pigment, resin and solvent is adopted, wherein compound S-1 has an aromatic ring and an azomethyl base structure, and can form a firm intermolecular bond with the pigment, inhibiting the aggregation of the pigment and Disperse to form a film with excellent heat resistance and few defects.
A film with excellent heat resistance and few defects is realized, which suppresses the aggregation and spectroscopy of pigments, and improves the performance of the color filter.
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Figure CN115427517B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a coloring composition containing a pigment and also to a film, an optical filter, a solid-state imaging element, and an image display device using the coloring composition. Background Art
[0002] In recent years, with the popularization of digital cameras and mobile phones with cameras, the demand for solid-state imaging elements such as charge-coupled device (CCD) image sensors has increased significantly. Color filters are used as core devices for displays or optical elements. Color filters usually have pixels of the three primary colors of red, green, and blue, and play a role in decomposing transmitted light into the three primary colors.
[0003] Colored pixels of each color of the color filter are manufactured using a coloring composition containing a colorant. Patent Document 1 describes a technique for forming pixels of a color filter using a coloring composition containing a pigment including an azomethine metal complex pigment, a pigment derivative having two sulfonic acid groups introduced into the azomethine metal complex pigment, a resin, and a solvent.
[0004] Previous technical literature
[0005] Patent Literature
[0006] Patent Document 1: Japanese Patent Application Publication No. 2009-035671 Summary of the invention
[0007] Technical issues to be solved by the invention
[0008] In recent years, the requirements for filters such as color filters have been increasing. As one of these required characteristics, the change of spectral characteristics is small even after heating and excellent heat resistance can be cited. Although it is easy to form a film with excellent heat resistance by using a pigment as a colorant, there is still room for further improvement. In addition, when a pigment is used as a colorant, an aggregate derived from the pigment is sometimes formed in the film, and there is a tendency to easily generate defects.
[0009] Furthermore, according to the research conducted by the present inventors, it has been found that the film obtained by using the coloring composition described in the examples of Patent Document 1 has insufficient heat resistance and a large change in spectral characteristics after heating. In addition, defects are easily generated in the film.
[0010] Therefore, an object of the present invention is to provide a coloring composition capable of producing a film having excellent heat resistance and suppressed generation of defects. In addition, an object of the present invention is to provide a film, an optical filter, a solid-state imaging element, and an image display device using the coloring composition.
[0011] Means for solving technical problems
[0012] According to the research of the present inventors, it was found that the above-mentioned object can be achieved by the coloring composition described below, and the present invention was completed. Therefore, the present invention provides the following.
[0013] <1> A coloring composition comprising:
[0014] At least one compound S selected from the group consisting of a compound S-1 represented by formula (1) and a compound S-2 in which the compound S-1 is coordinated to a metal atom;
[0015] pigment;
[0016] Resins; and
[0017] Solvents,
[0018] [Chemical formula 1]
[0019]
[0020] In the formula, R 1 represents a hydrogen atom, an alkyl group or an aryl group, R 2 ~R 9 Each independently represents a hydrogen atom or a substituent, R 2 ~R 9 Two adjacent groups in can be bonded to form a ring; wherein R 2 ~R 9 At least one of the compounds contains a group represented by formula (R-1);
[0021] -W 1 -(X 1 ) n ……(R-1)
[0022] In formula (R-1), W 1 represents an n+1 valent connecting group, X 1 represents an acid group or a basic group, and n represents an integer of 1 to 5.
[0023] <2> The colored composition according to <1>, wherein
[0024] X in the above formula (R-1) 1 The acid groups represented are carboxyl, sulfonyl, phosphate, -SO2NHSO2Rf 1 The groups or their salts, Rf 1 represents a group containing a fluorine atom,
[0025] X in the above formula (R-1) 1 The basic groups represented are salts of amino or ammonium groups.
[0026] <3> The colored composition according to <1> or <2>, wherein
[0027] X in the above formula (R-1) 1 It is a basic base.
[0028] <4> The colored composition according to any one of <1> to <3>, wherein
[0029] The above compound S-2 is a compound represented by formula (1a),
[0030] [Chemical formula 2]
[0031]
[0032] In the formula, R 1 represents a hydrogen atom, an alkyl group or an aryl group, R 2 ~R 9 Each independently represents a hydrogen atom or a substituent, R 2 ~R 9 Two adjacent groups in M can be bonded to form a ring. 1 represents the metal atom that the ligand can coordinate, where R 2 ~R 9 At least one of them contains a group represented by the above formula (R-1).
[0033] <5> The colored composition according to <4>, wherein
[0034] In the above formula (1a), M 1 It is a copper atom to which the ligand can coordinate or a zinc atom to which the ligand can coordinate.
[0035] <6> The colored composition according to any one of <1> to <5>, wherein
[0036] The pigment includes at least one selected from the group consisting of a yellow pigment, a green pigment, and a red pigment.
[0037] <7> The colored composition according to any one of <1> to <6>, wherein
[0038] The above-mentioned pigments include pigments having metal atoms.
[0039] <8> The colored composition according to <7>, wherein
[0040] The pigment having the above-mentioned metal atom includes an azomethine metal complex.
[0041] <9> The colored composition according to <8>, wherein
[0042] The azomethine metal complex includes at least one selected from the group consisting of azomethine copper complexes and azomethine zinc complexes.
[0043] <10> The colored composition according to any one of <1> to <9>, wherein
[0044] The compound S is contained in an amount of 1 to 30 parts by mass based on 100 parts by mass of the pigment.
[0045] <11> The colored composition according to any one of <1> to <10>, further comprising a polymerizable compound and a photopolymerization initiator.
[0046] <12> The colored composition according to any one of <1> to <11>, which is used for a color filter or an infrared transmission filter.
[0047] <13> The colored composition according to any one of <1> to <12>, which is used for a solid-state imaging element.
[0048] <14> A film obtained from the colored composition according to any one of <1> to <13>.
[0049] <15> An optical filter comprising the film according to <14>.
[0050] <16> A solid-state imaging element comprising the film according to <14>.
[0051] <17> An image display device comprising the film according to <14>.
[0052] Effects of the Invention
[0053] According to the present invention, it is possible to provide a film that is excellent in heat resistance and has reduced generation of defects, and to provide a film, an optical filter, a solid-state imaging element, and an image display device using the colored composition. DETAILED DESCRIPTION
[0054] Hereinafter, the contents of the present invention will be described in detail.
[0055] In this specification, "to" is used to mean that the numerical values described before and after it are included as the lower limit and the upper limit.
[0056] In the marking of groups (atomic groups) in this specification, the marking without the indication of substitution and unsubstituted includes not only groups (atomic groups) without substitution but also groups (atomic groups) with substitution. For example, "alkyl" includes not only alkyl groups without substitution (unsubstituted alkyl groups) but also alkyl groups with substitution (substituted alkyl groups).
[0057] 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. In addition, examples of light used for exposure include active light or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet rays represented by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
[0058] In the present specification, “(meth)acrylate” means both or either acrylate and methacrylate, “(meth)acrylic acid” means both or either acrylic acid and methacrylic acid, and “(meth)acryloyl” means both or either acryloyl and methacryloyl.
[0059] In the present specification, Me in the structural formula represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group.
[0060] In this specification, the weight average molecular weight and the number average molecular weight are polystyrene-equivalent values measured by GPC (gel permeation chromatography).
[0061] In this specification, the total solid content refers to the total mass of the components excluding the solvent from all the components of the composition.
[0062] In this specification, a pigment refers to a compound that is difficult to dissolve in a solvent.
[0063] In this specification, the term "step" refers not only to an independent step but also to a step that cannot be clearly distinguished from other steps as long as the intended effect of the step can be achieved.
[0064] <Coloring composition>
[0065] The coloring composition of the present invention is characterized by containing:
[0066] At least one compound S selected from the group consisting of a compound S-1 represented by formula (1) and a compound S-2 in which the compound S-1 is coordinated to a metal atom;
[0067] pigment;
[0068] Resins; and
[0069] Solvent.
[0070] According to the coloring composition of the present invention, a film having excellent heat resistance and suppressed defect generation can be produced. The detailed reason for obtaining such an effect is not clear, but it can be inferred as follows. It is inferred that compound S-1 has an aromatic ring and an azomethine structure, and compound S can form a strong intermolecular bond with the pigment. In addition, in compound S-1, R in formula (1) 2 ~R 9At least one of the compounds has a group represented by formula (R-1). That is, compound S-1 has a 1 A structure formed by bonding an acid group or a basic group, and the acid group or the basic group is bonded at a distance from the aromatic ring. It is speculated that because compound S-1 has such a structure, the interaction between the pigment and compound S is difficult to be hindered by the resin, and the interaction between compound S and the resin is also difficult to be hindered by the pigment. Therefore, it is speculated that a strong network between the pigment, compound S and the resin can be formed in the coloring composition or in the film. Therefore, it is speculated that the aggregation of the pigment during the dispersion process of the pigment or the storage of the coloring composition can be suppressed, and as a result, the generation of defects can be suppressed. In addition, it is speculated that even if the film is heated after film formation, a strong network will be formed between the pigment, compound S and the resin, so the pigment is difficult to separate from the resin, and the generation of spectral changes or cracks caused by the aggregation of the pigment can also be suppressed. Therefore, according to the coloring composition of the present invention, a film with excellent heat resistance and suppressed generation of defects can be manufactured.
[0071] In particular, compound S easily interacts with a pigment having a metal atom, and when a pigment having a metal atom is used, the generation of defects can be effectively suppressed. In particular, when an azomethine metal complex or a phthalocyanine metal complex is used, the generation of defects can be more effectively suppressed.
[0072] The coloring composition of the present invention can be preferably used as a coloring composition for color filters or infrared transmission filters. More specifically, it can be preferably used as a coloring composition for forming pixels of color filters or a coloring composition for forming infrared transmission filters, and can be more preferably used as a coloring composition for forming pixels of color filters.
[0073] Furthermore, the coloring composition of the present invention can be preferably used as a solid-state imaging element, and more specifically, 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 used in a solid-state imaging element.
[0074] When the coloring composition of the present invention is used to form a film with a thickness of 0.65 μm, the wavelength at which the transmittance of the film becomes 50% is preferably present in the wavelength range of 470 to 520 nm, more preferably in the wavelength range of 475 to 520 nm, and further preferably in the wavelength range of 480 to 520 nm. Among them, the wavelength at which the transmittance becomes 50% is preferably present in the wavelength range of 470 to 520 nm and in the wavelength range of 575 to 625 nm, respectively. In this embodiment, the wavelength on the short wavelength side at which the transmittance becomes 50% is preferably present in the wavelength range of 475 to 520 nm, and more preferably in the wavelength range of 480 to 520 nm. In addition, the wavelength on the long wavelength side at which the transmittance becomes 50% is preferably present in the wavelength range of 580 to 620 nm, and more preferably in the wavelength range of 585 to 615 nm. A coloring composition capable of forming a film having such a spectral characteristic can be preferably used as a coloring composition for forming green pixels of a color filter.
[0075] Hereinafter, each component used for the coloring composition of the present invention will be described.
[0076] <<Pigment>>
[0077] The coloring composition of the present invention contains a pigment. The average primary particle size of the pigment is preferably 1 to 200 nm. The lower limit is preferably 5 nm or more, more preferably 10 nm or more. The upper limit is preferably 180 nm or less, more preferably 150 nm or less, and further preferably 100 nm or less. If the average primary particle size of the pigment is within the above range, the dispersion stability of the pigment in the resin composition is good. In addition, in the present invention, the primary particle size of the pigment can be observed by a transmission electron microscope and obtained from the photographs obtained. Specifically, the projected area of the primary particles of the pigment is obtained, and the equivalent circle diameter corresponding thereto is calculated as the primary particle size of the pigment. In addition, the average primary particle size in the present invention is set to the arithmetic mean of the primary particle sizes of 400 primary particles of the pigment. In addition, the primary particles of the pigment refer to independent particles that are not agglomerated.
[0078] As the pigment, color pigments and black pigments can be mentioned, and color pigments are preferred. In addition, the pigment can be any of inorganic pigments and organic pigments, and organic pigments are preferred from the viewpoints of the amount of color change, ease of dispersion, safety, etc.
[0079] From the reason that a film that further suppresses the generation of defects can be formed, the pigment is preferably a pigment having a metal atom, more preferably an organic pigment having a metal atom, further preferably an azomethine metal complex, an azo metal complex and a phthalocyanine metal complex, further preferably an azomethine metal complex and a phthalocyanine metal complex, and particularly preferably an azomethine metal complex.
[0080] The azomethine metal complex is preferably a yellow pigment. Furthermore, the azomethine metal complex preferably includes at least one selected from azomethine copper complexes and azomethine zinc complexes, and more preferably includes azomethine copper complexes. The azomethine metal complex may be only one type, or two or more types may be used in combination. Furthermore, when two or more types of azomethine metal complexes are used in combination, the two or more types of azomethine metal complexes may form a mixed crystal (solid solution) with each other.
[0081] Examples of the azomethine copper complex include CI Pigment Yellow 117 and 129. CI Pigment Yellow 117 is a compound represented by the following formula (ACu-2), and CI Pigment Yellow 129 is a compound represented by the following formula (ACu-1). In the following structural formulas, the nitrogen atom is coordinated with the copper (Cu) atom, but the nitrogen atom may not be coordinated with the copper atom.
[0082] [Chemical formula 3]
[0083]
[0084] Examples of the azomethine zinc complex include compounds represented by formula (AZn-1), compounds represented by formula (AZn-2), etc. In the following structural formula, the nitrogen atom coordinates with the zinc (Zn) atom, but the nitrogen atom may not coordinate with the zinc atom.
[0085] [Chemical formula 4]
[0086]
[0087] In the formula (AZn-2), X 1 and X 2 Each independently represents a hydrogen atom, a halogen atom or an alkoxy group.
[0088] As X 1 and X 2 Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom or a bromine atom is preferred, and a chlorine atom is more preferred.
[0089] As X 1 and X 2Examples of the alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. Among them, suitable examples include alkoxy groups having 1 to 8 carbon atoms.
[0090] Specific examples of the compound represented by the formula (AZn-2) include compounds having the structures shown below: In the following structural formula, the nitrogen atom is coordinated to the zinc (Zn) atom, but the nitrogen atom may not be coordinated to the zinc atom.
[0091] [Chemical formula 5]
[0092]
[0093] Examples of the azo metal complex include CI Pigment Yellow 150.
[0094] Furthermore, as the azo metal complex, an azobarbituric acid nickel complex having the following structure can also be used.
[0095] [Chemical formula 6]
[0096]
[0097] Furthermore, as the azo metal complex, an azo metal complex Az containing at least one anion selected from an azo compound represented by the following formula (Az1) and an azo compound having a tautomeric structure thereof, two or more metal ions, and a melamine compound can also be used.
[0098] [Chemical formula 7]
[0099]
[0100] In the formula, R 1 and R 2 are independently -OH or -NR 5 R 6 , R 3 and R 4 are independently =O or =NR7 , R 5 ~R 7 are independently a hydrogen atom or an alkyl group. 5 ~R 7 The number of carbon atoms of the alkyl group represented is preferably 1 to 10, more preferably 1 to 6, and further preferably 1 to 4. The alkyl group may be any of linear, branched, and cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. The substituent is preferably a halogen atom, a hydroxyl group, an alkoxy group, a cyano group, and an amino group.
[0101] In formula (Az1), preferably R 1 and R 2 is -OH. And preferably R 3 and R 4 is =O.
[0102] The azo metal complex Az preferably contains at least one anion selected from the group consisting of the azo compounds represented by the above formula (Az1) and azo compounds with tautomeric structures thereof, and at least Zn 2+ Cu 2+ Regarding the azo metal complex Az, reference may be made to paragraphs 0011 to 0062 and 0137 to 0276 of Japanese Patent Application Publication No. 2017-171912, paragraphs 0010 to 0062 and 0138 to 0295 of Japanese Patent Application Publication No. 2017-171913, paragraphs 0011 to 0062 and 0139 to 0190 of Japanese Patent Application Publication No. 2017-171914, and paragraphs 0010 to 0065 and 0142 to 0222 of Japanese Patent Application Publication No. 2017-171915, and these contents are incorporated into this specification.
[0103] Phthalocyanine metal complexes include phthalocyanine metal complexes (metal phthalocyanine pigments) having copper, zinc, aluminum, iron, cobalt, vanadium, titanium or magnesium as a central metal. Specific examples of phthalocyanine metal complexes include green pigments such as Color Index (CI) Pigment Green 7, 36, 58, 59, 62, and 63, and blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, and 15:6.
[0104] Hereinafter, the color pigments and the black pigment will be described in further detail.
[0105] (Color Pigments)
[0106] As color pigments, pigments having a maximum absorption wavelength in the range of 400 to 700 nm can be cited. For example, yellow pigments, orange pigments, red pigments, green pigments, purple pigments, blue pigments, etc. can be cited. The pigment used in the coloring composition of the present invention preferably includes at least one selected from yellow pigments, green pigments, and red pigments, and more preferably includes a yellow pigment.
[0107] As yellow pigments, azomethine compounds, azo compounds, isoindoline compounds, pteridine compounds and quinophthalone compounds are mentioned, preferably azomethine compounds and azo compounds, more preferably azomethine metal complexes and azo metal complexes, and preferably azomethine metal complexes because they can form films with few defects and excellent heat resistance. As azomethine metal complexes and azo metal complexes, the above-mentioned ones are mentioned.
[0108] Specific examples of yellow pigments other than azomethine metal complexes and azo metal complexes include CI 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 0, 123, 125, 126, 127, 128, 137, 138, 139, 147, 148, 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 series), 233 (quinoline series), 234 (aminoketone series), 235 (aminoketone series), 236 (aminoketone series), etc.
[0109] In addition, as yellow pigments, quinophthalone compounds described in paragraphs 0011 to 0034 of Japanese Patent Publication No. 2013-054339, quinophthalone compounds described in paragraphs 0013 to 0058 of Japanese Patent Publication No. 2014-026228, isoindoline compounds described in Japanese Patent Publication No. 2018-062644, quinophthalone compounds described in Japanese Patent Publication No. 2018-203798, quinophthalone compounds described in Japanese Patent Publication No. 2018-062578, quinophthalone compounds described in Japanese Patent No. 6432076, and Japanese Quinophthalone compounds described in Japanese Patent Publication No. 2018-155881, quinophthalone compounds described in Japanese Patent Publication No. 2018-111757, quinophthalone compounds described in Japanese Patent Publication No. 2018-040835, quinophthalone compounds described in Japanese Patent Publication No. 2017-197640, quinophthalone compounds described in Japanese Patent Publication No. 2016-145282, quinophthalone compounds described in Japanese Patent Publication No. 2014-085565, quinophthalone compounds described in Japanese Patent Publication No. 2014-021139, quinophthalone compounds described in Japanese Patent Publication No. 2013-2 Quinophthalone compounds described in Japanese Patent Application No. 09614, quinophthalone compounds described in Japanese Patent Application No. 2013-209435, quinophthalone compounds described in Japanese Patent Application No. 2013-181015, quinophthalone compounds described in Japanese Patent Application No. 2013-061622, quinophthalone compounds described in Japanese Patent Application No. 2013-032486, quinophthalone compounds described in Japanese Patent Application No. 2012-226110, quinophthalone compounds described in Japanese Patent Application No. 2008-074987, quinophthalone compounds described in Japanese Patent Application No. 2008-081565 Quinophthalone compounds described in , quinophthalone compounds described in Japanese Patent Publication No. 2008-074986, quinophthalone compounds described in Japanese Patent Publication No. 2008-074985, quinophthalone compounds described in Japanese Patent Publication No. 2008-050420, quinophthalone compounds described in Japanese Patent Publication No. 2008-031281, quinophthalone compounds described in Japanese Patent Publication No. 48-032765, quinophthalone compounds described in Japanese Patent Publication No. 2019-008014, and quinophthalone compounds described in Japanese Patent Publication No. 6607427. In addition, from the viewpoint of improving the color value, it is also preferable to use polymers of these compounds.
[0110] As the yellow pigment, CI Pigment Yellow 117, 129, 138, 139, 150, and 185 are preferred, CI Pigment Yellow 117 and 129 are more preferred, and CI Pigment Yellow 129 is further preferred.
[0111] Examples of red pigments include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds and thioindigo compounds. From the perspective of being able to form a film with few defects and excellent heat resistance, diketopyrrolopyrrole compounds and quinacridone compounds are preferred, and diketopyrrolopyrrole compounds are more preferred.
[0112] Specific examples of red pigments include CI 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, 145 6, 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, etc. In addition, as the red pigment, a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure, as described in Japanese Patent Publication No. 2017-201384, a diketopyrrolopyrrole compound described in paragraphs 0016 to 0022 of Japanese 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 Japanese Patent Publication No. 2012-229344, a red pigment described in Japanese Patent No. 6516119, a red pigment described in Japanese Patent No. 6525101, etc. can also be used. Furthermore, as the red pigment, a compound having a structure in which an aromatic ring group formed by introducing a group to which an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring and a diketopyrrolopyrrole skeleton is bonded can also be used.
[0113] As the red pigment, CI Pigment Red 122, 177, 254, 255, 264, 269, and 272 are preferred, and CI Pigment Red 254, 255, 264, and 272 are more preferred.
[0114] Examples of green pigments include phthalocyanine compounds and squarylium compounds. Phthalocyanine compounds are preferred, and phthalocyanine metal complexes are more preferred, because they can form a film with few defects and excellent heat resistance.
[0115] Specific examples of green pigments include CI Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66, etc. In addition, as green pigments, zinc phthalocyanine halides having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule can also be used. As specific examples, compounds described in International Publication No. 2015 / 118720 can be cited.
[0116] In addition, as green pigments, compounds described in the specification of Chinese Patent Application No. 106909027, phthalocyanine compounds having phosphate as ligands described in International Publication No. 2012 / 102395, phthalocyanine compounds described in Japanese Patent Publication No. 2019-008014, phthalocyanine compounds described in Japanese Patent Publication No. 2018-180023, compounds described in Japanese Patent Publication No. 2019-038958, and square acid compounds described in paragraphs 0141 to 0151 of International Publication No. 2019 / 167589 can be used. As green pigments, CI Pigment Green 7, 36, 58, 59, 62, and 63 are preferred.
[0117] Examples of the orange pigment include CI 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, and 73.
[0118] Examples of the violet pigment include CI Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
[0119] Examples of the blue pigment include CI Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88.
[0120] Regarding the preferred diffraction angles of various pigments, reference can be made to the descriptions of Japanese Patent Nos. 6561862, 6413872, 6281345, and JP-A-2020-026503, the contents of which are incorporated into the present specification.
[0121] The coloring composition may contain more than two kinds of color pigments. For example, a coloring composition containing a yellow pigment and a green pigment can be preferably used as a coloring composition for forming green pixels of a color filter. In this case, the yellow pigment preferably contains an azomethine metal complex. In addition, the green pigment preferably contains a phthalocyanine metal complex.
[0122] Furthermore, a coloring composition containing a yellow pigment and a red pigment can be preferably used as a coloring composition for forming red pixels of a color filter. In this case, the yellow pigment preferably contains an azomethine metal complex. Furthermore, the red pigment preferably contains a diketopyrrolopyrrole compound.
[0123] Furthermore, the coloring composition contains two or more color pigments, and black can be formed by a combination of two or more color pigments. These coloring compositions can be preferably used as coloring compositions for forming infrared transmission filters. The following can be cited as a combination of color pigments when black is formed by a combination of two or more color pigments.
[0124] (A1) A form containing a red pigment, a blue pigment, and a yellow pigment.
[0125] (A2) A method of containing a red pigment, a blue pigment, a yellow pigment, and a violet pigment.
[0126] (A3) A method of containing a red pigment, a blue pigment, a yellow pigment, a violet pigment, and a green pigment.
[0127] (A4) A method of containing a red pigment, a blue pigment, a yellow pigment, and a green pigment.
[0128] (A5) A form containing a yellow pigment and a purple pigment.
[0129] (Black pigment)
[0130] As black pigment, there is no particular limitation, and known substances can be used. For example, inorganic pigments such as carbon black, titanium black, and graphite can be cited, preferably carbon black and titanium black, and more preferably titanium black. Titanium black refers to black particles containing titanium atoms, preferably low-grade titanium oxide or titanium oxynitride. For the purpose of improving dispersibility, inhibiting cohesion, etc., the surface of titanium black can be modified as needed. For example, the surface of titanium black can be coated with silicon oxide, titanium oxide, germanium oxide, aluminum oxide, magnesium oxide, or zirconium oxide. In addition, it can also be treated with a waterproof substance as shown in Japanese Patent Publication No. 2007-302836. The primary particle size and average primary particle size of each particle of titanium black are preferably small. Specifically, the average primary particle size is preferably 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silicon dioxide particles and the content ratio of Si atoms to Ti atoms in the dispersion is adjusted in the range of 0.20 to 0.50. For the above-mentioned dispersion, reference can also be made to paragraphs 0020 to 0105 of Japanese Patent Publication No. 2012-169556, which is incorporated into this specification. Examples of commercially available titanium blacks include titanium black 10S, 12S, 13R, 13M, 13M-C, 13R-N, 13M-T (product name: manufactured by Mitsubishi Materials Corporation), Tilack D (product name: manufactured by Ako Kasei Co., Ltd.), and the like.
[0131] The content of the pigment in the total solid content of the coloring composition is preferably 20% by mass or more, more preferably 30% by mass or more, further preferably 40% by mass or more, and particularly preferably 50% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and further preferably 70% by mass or less.
[0132] The content of the pigment having a metal atom in the pigment contained in the coloring composition is preferably 15% by mass or more, more preferably 15.5% by mass or more, and further preferably 16% by mass or more. The upper limit can be 100% by mass, can be 95% by mass or less, and can be 90% by mass or less.
[0133] The content of the azomethine metal complex in the pigment contained in the coloring composition is preferably 15% by mass or more, more preferably 15.5% by mass or more, and further preferably 16% by mass or more. The upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
[0134] The content of the yellow pigment in the pigment contained in the coloring composition is preferably 30% by mass or more, more preferably 33% by mass or more, and further preferably 35% by mass or more. The upper limit can be 100% by mass, or can be 95% by mass or less, or can be 90% by mass or less.
[0135] When the colored composition of the present invention is used as a colored composition for forming yellow pixels of a color filter, the content of the yellow pigment in the pigment is preferably 90% by mass or more, more preferably 95% by mass or more, and further preferably 99% by mass or more.
[0136] When the coloring composition of the present invention is used as a coloring composition for forming green pixels of a color filter, the pigment preferably uses a pigment containing a yellow pigment and a green pigment. In addition, the mass ratio of the yellow pigment to the green pigment is preferably yellow pigment: green pigment = 30:70 to 70:30, more preferably 30:70 to 60:40, and further preferably 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, and further preferably 10 parts by mass or more relative to 100 parts by mass of the green pigment.
[0137] When the coloring composition of the present invention is used as a coloring composition for forming red pixels of a color filter, the pigment preferably uses a pigment containing a yellow pigment and a red pigment. In addition, the mass ratio of the yellow pigment to the red pigment is preferably yellow pigment: red pigment = 30:70 to 70:30, more preferably 30:70 to 60:40, and further preferably 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, and further preferably 10 parts by mass or more relative to 100 parts by mass of the red pigment.
[0138] <<Dye>>
[0139] The coloring composition of the present invention can contain a dye. As a dye, there is no particular limitation, and a known dye can be used. As a dye, color dyes and black dyes can be mentioned. As color dyes, pyrazole azo compounds, aniline azo compounds, triarylmethane compounds, anthraquinone compounds, anthrapyridone compounds, benzylidene compounds, oxaphenol compounds, pyrazolotriazole azo compounds, pyridone azo compounds, cyanine compounds, phenothiazine compounds, pyrrolopyrazole azomethine compounds, xanthene compounds, phthalocyanine compounds, benzopyran compounds, indigo compounds, pyrrole methylene compounds can be mentioned. As black dyes, bisbenzofuranone compounds, azomethine compounds, perylene compounds, azo compounds, etc. can be mentioned.
[0140] The content of the dye is preferably 100 parts by mass or less, more preferably 50 parts by mass or less, further preferably 30 parts by mass or less, and particularly preferably 10 parts by mass or less, relative to 100 parts by mass of the pigment.
[0141] Furthermore, the coloring composition of the present invention may be set to contain substantially no dye. When the coloring composition of the present invention contains substantially no dye, the content of the dye in the total solid content of the coloring composition of the present invention is preferably 0.1% by mass or less, more preferably 0.05% by mass or less, and particularly preferably no dye.
[0142] <<Compound S>>
[0143] The coloring composition of the present invention contains at least one compound S selected from the group consisting of a compound S-1 represented by the formula (1) and a compound S-2 in which the compound S-1 is coordinated to a metal atom.
[0144] [Chemical formula 8]
[0145]
[0146] In the formula, R 1 represents a hydrogen atom, an alkyl group or an aryl group, R 2 ~R 9 Each independently represents a hydrogen atom or a substituent, R 2 ~R 9 Two adjacent groups in can be bonded to form a ring; wherein R 2 ~R 9 At least one of the compounds contains a group represented by formula (R-1);
[0147] -W 1 -(X 1 ) n ……(R-1)
[0148] In formula (R-1), W 1 represents an n+1 valent connecting group, X 1 represents an acid group or a basic group, and n represents an integer of 1 to 5.
[0149] R in formula (1) 1 The number of carbon atoms of the alkyl group represented is preferably 1 to 30, more preferably 1 to 15, and further preferably 1 to 8. The alkyl group may be any of linear, branched, and cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. Examples of the substituent include the substituent T described below.
[0150] R in formula (1) 1The number of carbon atoms of the aryl group represented is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 12. The aryl group may have a substituent. Examples of the substituent include the substituent T described below.
[0151] R in formula (1) 1 It is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
[0152] R 2 ~R 9 Each independently represents a hydrogen atom or a substituent. As a substituent, a substituent T described below and a group represented by formula (R-1) can be cited. As a substituent other than the group represented by formula (R-1), preferably a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic group, an acyloxy group, a carbamoyloxy group, an amino group, an amide group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heteroarylthio group, a sulfamoyl group, a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkyl The alkylsulfonyl group is a alkylsulfonyl group, an arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an arylazo group, a heteroarylazo group, an imide group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group or a silyl group; more preferably, a halogen atom, an alkyl group, an aryl group, a heteroaryl group, a cyano group, a hydroxyl group, a nitro group, an alkoxy group, an aryloxy group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group or a carbamoyl group; further preferably, a halogen atom, an aryl group, a cyano group, a hydroxyl group, a nitro group, an alkoxy group, an aryloxy group or an acyl group; and particularly preferably, a halogen atom, an aryl group, a cyano group or a nitro group.
[0153] In formula (1), R 2 ~R 9 At least one of them contains a group represented by formula (R-1), preferably R 2 ~R 9 1 to 4 of them contain a group represented by formula (R-1), and more preferably R 2 ~R 9 1 to 2 of them contain a group represented by formula (R-1), and more preferably R 2 ~R 9 Any one of them contains a group represented by formula (R-1).
[0154] Furthermore, R is preferred because it can make the particle size of the dispersed pigment smaller and improve the dispersibility of the pigment. 6 ~R 9 At least one of them contains a group represented by formula (R-1), and more preferably R 6 ~R 9 1 to 2 of them contain a group represented by formula (R-1), and more preferably R6 ~R 9 Any one of them contains a group represented by formula (R-1).
[0155] R 2 ~R 9 Two adjacent groups in may be bonded to form a ring. The formed ring is preferably an aromatic ring.
[0156] Next, the group represented by the formula (R-1) is described. 1 It represents an n+1 valent linking group.
[0157] As W 1 The n+1-valent linking group represented by may be an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO-, -SO2-, -NR W -、-NR W CO-、-CONR W -、-NR W SO2-、-SO2NR W - and groups composed of these combinations, R W represents a hydrogen atom, an alkyl group or an aryl group.
[0158] The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 20, more preferably 2 to 20, further preferably 2 to 10, and particularly preferably 2 to 5. The aliphatic hydrocarbon group may be any of linear, branched, and cyclic. Furthermore, the cyclic aliphatic hydrocarbon group may be any of monocyclic and polycyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and further preferably 6 to 10. The aromatic hydrocarbon group is preferably a monocyclic or condensed ring aromatic hydrocarbon group having a condensed number of 2 to 4. As the aromatic hydrocarbon group, a benzene ring group is preferred. The heterocyclic group is preferably a monocyclic or condensed ring having a condensed number of 2 to 4. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3. The heteroatoms constituting the ring of the heterocyclic group are preferably nitrogen atoms, oxygen atoms, or sulfur atoms. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and more preferably 3 to 12. As the heterocyclic group, a triazine ring group is preferred. The aliphatic hydrocarbon group, the aromatic hydrocarbon group and the heterocyclic group may have a substituent. As the substituent, the groups exemplified in the substituent T described below can be mentioned. W The number of carbon atoms in the alkyl group represented is preferably 1 to 20, more preferably 1 to 15, and still more preferably 1 to 8. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. W The alkyl group represented by may further have a substituent. As the substituent, the substituent T described below can be mentioned. W The number of carbon atoms of the aryl group represented by is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.W The aryl group represented by may further have a substituent. As the substituent, the substituent T described below can be mentioned.
[0159] In the group represented by formula (R-1), X 1 It represents an acid group or a basic group, and a basic group is preferred because a film having a higher heat resistance can be easily formed.
[0160] As X 1 The acid group represented by may be carboxyl, sulfonyl, phosphoric acid, -SO2NHSO2Rf 1 A group represented by or a salt thereof. 1 Rf in the group represented 1 represents a group containing a fluorine atom. 1 The fluorine-containing group represented by fluorine atom includes fluorine atom, alkyl group containing fluorine atom, and aryl group containing fluorine atom, preferably alkyl group containing fluorine atom. The number of carbon atoms of alkyl group containing fluorine atom is preferably 1 to 10, more preferably 1 to 5, and further preferably 1 to 3. The number of carbon atoms of aryl group containing fluorine atom is preferably 6 to 20, more preferably 6 to 12, and further preferably 6.
[0161] Examples of the atoms or atomic groups constituting the salt include alkali metal ions (Li + 、Na + , K + etc.), alkaline earth metal ions (Ca 2+ Mg 2+ etc.), ammonium ion, imidazolium ion, pyridinium ion, phosphonium ion, etc.
[0162] X 1 The acid group represented is preferably a sulfonic acid group, a phosphoric acid group, or a -SO2NHSO2Rf 1 A group represented by or a salt thereof, more preferably a sulfo group, a group represented by -SO2NHSO2Rf 1 A group represented by or a salt thereof.
[0163] As X 1 The basic group represented by the present invention includes amino, ammonium salts and phthalimide methyl, preferably amino and ammonium salts, more preferably amino. As the atom or atomic group constituting the salt in the ammonium salt, hydroxide ion, halogen ion, carboxylate ion, sulfonate ion, phenoxide ion, etc. can be mentioned.
[0164] As the amino group, there can be mentioned -NRx 1 Rx 2 Representing a group and a cyclic amino group.
[0165] By -NRx 1 Rx 2 In the group represented by1 and Rx 2 Each independently represents a hydrogen atom, an alkyl group and an aryl group, preferably an alkyl group. The number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 5, and further preferably 1 to 3. The alkyl group may be any of a linear, branched, or cyclic group, preferably a linear or branched group, and further preferably a linear group. The alkyl group may have a substituent. As the substituent, the substituent T described below may be mentioned. The number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 12. The aryl group may have a substituent. As the substituent, the substituent T described below may be mentioned.
[0166] Examples of the cyclic amino group include pyrrolidinyl, piperidinyl, piperazinyl, and morpholinyl. These groups may further have a substituent. Examples of the substituent include the substituent T described below. Examples of the substituent include an alkyl group and an aryl group.
[0167] In the group represented by the formula (R-1), n is preferably 1 to 3, more preferably 1 or 2, and further preferably 1.
[0168] The group represented by the formula (R-1) is preferably a group represented by the formula (R-11).
[0169] -W 11 -W 12 -(W 13 -X 1 ) n ……(R-11)
[0170] W of formula (R-11) 11 Represents a single bond, -O-, -S-, -CO-, -COO-, -OCO-, -OCO2-, -NR W -、-SO2-、-NR W CO-、-CONR W -、-NR W CO2-、-OCONR W -、-NR W SO2- or -SO2NR W -, R W represents a hydrogen atom, an alkyl group or an aryl group. W The number of carbon atoms in the alkyl group represented is preferably 1 to 20, more preferably 1 to 15, and still more preferably 1 to 8. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. W The alkyl group represented by may further have a substituent. As the substituent, there can be mentioned the substituent T described below. W The number of carbon atoms of the aryl group represented by is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 12. WThe aryl group represented by may further have a substituent. As the substituent, the substituent T described below can be mentioned. W Can be used with X 1 connect to form a ring. For example, X 1 For-NRx 1 Rx 2 In the case of a group represented by W Can be used with Rx 1 or Rx 2 The formed ring is preferably a 5-membered ring or a 6-membered ring.
[0171] W of formula (R-11) 12 represents a single bond or an n+1 valent linking group. When n is 1, W 12 is a single bond or a divalent linking group, and when n is 2 or more, W 12 is an n+1 valent linking group. 12 The linking group represented by may be an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO-, -SO2-, -NR W -、-N<、-NR W CO-、-CONR W -、-NR W SO2-、-SO2NR W - and groups formed by combining these. W The meaning is the same as above R w has the same meaning as W. 12 It is preferably a group containing at least one selected from an aliphatic hydrocarbon group, an aromatic hydrocarbon group and a heterocyclic group. Examples of the aliphatic hydrocarbon group, the aromatic hydrocarbon group and the heterocyclic group include the above-mentioned groups. 12 Specific examples of the linking group represented by include aliphatic hydrocarbon groups; aromatic hydrocarbon groups; heterocyclic groups; a combination of at least one selected from aliphatic hydrocarbon groups, aromatic hydrocarbon groups and heterocyclic groups and -O-, -S-, -CO-, -COO-, -OCO-, -SO2-, -NR W -、-N<、-NR W CO-、-CONR W -、-NR W SO2- and -SO2NR W -, etc. As W 12 A preferred embodiment of the present invention includes a group containing at least one selected from an aromatic hydrocarbon group and a heterocyclic group. As a group containing at least one selected from an aromatic hydrocarbon group and a heterocyclic group, groups represented by the following formula (W12-1) to formula (W12-6) can be mentioned.
[0172] [Chemical formula 9]
[0173]
[0174] In formulas (W12-1) to (W12-6), * is the same as W in formula (R-1). 11 The wavy line is the bonding part with W of formula (R-1). 13 The bonding portion.
[0175] A of formula (W12-1) 1 Indicates O or NR W12 . R W12 The meaning is the same as above R w has the same meaning. 1 Indicates an integer from 1 to 4.
[0176] A of formula (W12-2) 2 、n 2 The meaning of A 1 、n 1 The meaning is the same as B. 2 Represents a single bond, -O-, -S-, -CO-, -COO-, -OCO-, -SO2-, -NR W -、-NR W CO-、-CONR W -、-NR W SO2- or -SO2NR W -. R W12 The meaning is the same as above R w have the same meaning.
[0177] T of formula (W12-3) 3 represents a substituent T described later. 3 The meaning of A 1 have the same meaning.
[0178] T of formula (W12-4) 4 , A 4 , B 4 The meaning of T 3 , A 1 , B 2 have the same meaning.
[0179] A of formula (W12-5) 5 The meaning of A 1 have the same meaning.
[0180] A of formula (W12-6) 6 , B 6 The meaning of A 1 , B 2 have the same meaning.
[0181] The above T 3and T 4 It is preferably a hydroxyl group, an amino group, an alkoxy group, an aryloxy group, a thioalkyl group, a thioaryl group or a halogen atom, and more preferably a hydroxyl group or an amino group. The amino group is preferably an alkylamino group or an arylamino group, and more preferably an arylamino group.
[0182] W of formula (R-11) 13 The alkylene group preferably has 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, and further preferably 2 to 5 carbon atoms.
[0183] X of formula (R-11) 1 represents an acid group or a basic group. 1 The meaning of X in formula (R-1) 1 have the same meaning.
[0184] n in formula (R-11) represents an integer of 1 to 5, is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.
[0185] Specific examples of the group represented by formula (R-1) include the following groups.
[0186] [Table 1]
[0187] -W 11 -W 12 -(W 13 -X 1 ) n
[0188]
[0189] [Table 2]
[0190] -W 11 -W 12 -(W 13 -X 1 ) n
[0191]
[0192] In the above table, Me represents a methyl group, and Et represents an ethyl group. In particular, the parts representing a and b represent bonding parts, and a represents the bonding part with W. 11 The bonded compound b is 13 In addition, the group of R-127 is a group having W 11 With X 1 A group of a structure in which two or more atoms are bonded to form a ring and has the structure shown below. * represents a bonding bond.
[0193] [Chemical formula 10]
[0194]
[0195] (Substituent T)
[0196] The substituent T includes the following groups: halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (preferably alkyl group having 1 to 30 carbon atoms), alkenyl group (preferably alkenyl group having 2 to 30 carbon atoms), alkynyl group (preferably alkynyl group having 2 to 30 carbon atoms), aryl group (preferably aryl group having 6 to 30 carbon atoms), heteroaryl group (preferably heteroaryl group having 1 to 30 carbon atoms), amino group (preferably amino group having 0 to 30 carbon atoms), alkoxy group (preferably alkoxy group having 1 to 30 carbon atoms), aryloxy group (preferably aryloxy group having 6 to 30 carbon atoms), heteroaryloxy group (preferably heteroaryloxy group having 1 to 30 carbon atoms), acyl group (preferably acyl group having 2 to 30 carbon atoms), alkoxycarbonyl group (preferably The present invention is an alkoxycarbonyl group having 2 to 30 carbon atoms), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms), a heteroaryloxycarbonyl group (preferably a heteroaryloxycarbonyl group having 2 to 30 carbon atoms), an acyloxy group (preferably an acyloxy group having 2 to 30 carbon atoms), an acylamino group (preferably an acylamino group having 2 to 30 carbon atoms), an aminocarbonylamino group (preferably an aminocarbonylamino group having 2 to 30 carbon atoms), an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms), an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms), a sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms), a sulfamoylamino group (preferably a sulfamoylamino group having 1 to 30 carbon atoms), carbamoyl group (preferably carbamoyl group having 1 to 30 carbon atoms), alkylthio group (preferably alkylthio group having 1 to 30 carbon atoms), arylthio group (preferably arylthio group having 6 to 30 carbon atoms), heteroarylthio group (preferably heteroarylthio group having 1 to 30 carbon atoms), alkylsulfonyl group (preferably alkylsulfonyl group having 1 to 30 carbon atoms), alkylsulfonylamino group (preferably alkylsulfonylamino group having 1 to 30 carbon atoms), arylsulfonyl group (preferably arylsulfonyl group having 6 to 30 carbon atoms), arylsulfonylamino group (preferably arylsulfonylamino group having 6 to 30 carbon atoms), heteroarylsulfonyl group (preferably heteroarylsulfonyl group having 1 to 30 carbon atoms) The present invention also includes an alkyl group, an alkylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an arylsulfinyl group, an urea group, an urea group, an urea group, an hydroxyl group, a nitro group, a carboxyl group, a sulfo group, a phosphoric acid group, a carboxylic acid amide group, a sulfonic acid amide group, an imide group, a phosphino group, a mercapto group, a cyano group, an alkylsulfinyl group, an arylsulfinyl group, an arylazo group, a heteroarylazo group, a phosphinyl group, a phosphinyloxy group, an phosphinylamino group, a silyl group, a hydrazino group, and an imino group. When these groups are further substituted groups, they may further have a substituent.As the substituent, the groups explained in the above-mentioned substituent T can be mentioned.
[0197] The compound S-1 is preferably a compound represented by formula (11).
[0198] [Chemical formula 11]
[0199]
[0200] In formula (11), R 21 represents a hydrogen atom, an alkyl group or an aryl group, R 22 ~R 31 Each independently represents a hydrogen atom or a substituent; wherein R 22 ~R 31 At least one of them is a group represented by formula (R-1).
[0201] R in formula (11) 21 The meaning of is the same as R in formula (1) 1 The meanings are the same, and the preferred ranges are also the same.
[0202] As R in formula (11) 22 ~R 31 The substituent represented by the formula (R-1) includes a substituent T and a group represented by the formula (R-1). As a substituent other than the group represented by the formula (R-1), a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic group, an acyloxy group, a carbamoyloxy group, an amino group, an amide group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkylsulfonylamino group, an arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heteroarylthio group, a sulfamoyl group, a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkyl A sulfonyl group, an arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an arylazo group, a heteroarylazo group, an imide group, a phosphinyl group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group or a silyl group, more preferably a halogen atom, an alkyl group, an aryl group, a heteroaryl group, a cyano group, a hydroxyl group, a nitro group, an alkoxy group, an aryloxy group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group or a carbamoyl group, further preferably a halogen atom, an aryl group, a cyano group, a hydroxyl group, a nitro group, an alkoxy group, an aryloxy group or an acyl group, and particularly preferably a halogen atom, an aryl group, a cyano group or a nitro group.
[0203] In formula (11), preferably R 22 ~R 31 1 to 4 of them are groups represented by formula (R-1), more preferably 1 or 2 of them are groups represented by formula (R-1), and even more preferably 1 of them is a group represented by formula (R-1). 29 or R 30It is a group represented by the formula (R-1).
[0204] In compound S, compound S-2 is a compound having a structure in which compound S-1 is coordinated on a metal atom. Examples of metal atoms include copper, zinc, iron, titanium, aluminum, tin, magnesium and chromium, preferably copper and zinc. In compound S-, one compound S-1 may be coordinated on these metal atoms, or two or more compound S-1s may be coordinated. Furthermore, a ligand other than compound S-1 may be coordinated on the metal atom. Examples of the ligand include heterocyclic compounds (e.g., pyridine, pyrimidine, imidazole, pyrazole, triazole, tetrazole, quinoline, 1,10-phenanthroline, etc.), protic compounds (e.g., water, methanol, ethanol, etc.), amine compounds (e.g., triethylamine, N,N,N',N'-tetramethylenediamine, ethylenediaminetetraacetic acid, N,N,N',N",N"-pentamethyldiethylenetriamine, etc.), amide compounds (e.g., N,N-dimethylacetamide, N-methylpyrrolidone, etc.), dimethyl sulfoxide, sulfolane, nitrile compounds (e.g., acetonitrile, etc.), and the like.
[0205] Compound S-2 is preferably a compound represented by formula (1a), and more preferably a compound represented by formula (11a). In the formula shown below, the nitrogen atom is located at the metal atom (M 1 or M 2 ), but depending on the state of the metal atom, the nitrogen atom may not be coordinated with the metal atom (M 1 or M 2 ) coordination.
[0206] [Chemical formula 12]
[0207]
[0208] In formula (1a), R 1 represents a hydrogen atom, an alkyl group or an aryl group, R 2 ~R 9 Each independently represents a hydrogen atom or a substituent, R 2 ~R 9 Two adjacent groups in M can be bonded to form a ring. 1 represents the metal atom that the ligand can coordinate; where R 2 ~R 9 At least one of them contains a group represented by formula (R-1).
[0209] In formula (11a), R 21 represents a hydrogen atom, an alkyl group or an aryl group, R 22 ~R 31 Each independently represents a hydrogen atom or a substituent, M 2 represents the metal atom that the ligand can coordinate; where R 22 ~R31 At least one of them is a group represented by formula (R-1).
[0210] R in formula (1a) 1 ~R 9 The meaning of is the same as R in formula (1) 1 ~R 9 The meanings are the same, and the preferred ranges are also the same.
[0211] R in formula (11a) 21 ~R 31 The meaning of is the same as R in formula (11) 21 ~R 31 The meanings are the same, and the preferred ranges are also the same.
[0212] As M in formula (1a) 1 And M in formula (11a) 2 The metal atom that the represented ligand can coordinate to includes copper, zinc, iron, titanium, aluminum, tin, magnesium and chromium, preferably copper and zinc. As the ligand that can coordinate to these metal atoms, the ligands exemplified by the ligands other than compound S-1 can be mentioned. In addition, the compound represented by formula (1) can be further coordinated.
[0213] Specific examples of the compound S include compounds (S-1) to (S-38) described in the Examples described below.
[0214] As a method for synthesizing compound S, the following method can be mentioned.
[0215] (i) A method of synthesizing by reacting a raw material (hydroxy-substituted aryl aldehyde or hydroxy-substituted aniline) into which an acid group or a basic group has been introduced in advance with a metal source.
[0216] (ii) A method of synthesizing by introducing an acid group or a basic group into an azomethine compound synthesized by reacting a hydroxy-substituted aryl aldehyde or a hydroxy-substituted aniline with a metal source.
[0217] In the case of the synthesis method (i), the hydroxy-substituted aryl aldehyde or hydroxy-substituted aniline and the metal source may be mixed and reacted simultaneously, or the hydroxy-substituted aniline and the hydroxy-substituted aryl aldehyde may be reacted first and then reacted with the metal source. In this reaction, for example, an acidic compound (e.g., acetic acid, sulfuric acid, etc.) or a basic compound (e.g., triethylamine, pyridine, etc.) may be added. The solvent can be selected from known solvents, and examples thereof include alcohol solvents (e.g., methanol, ethanol, isopropanol, propylene glycol monomethyl ether, etc.), amide solvents (e.g., N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, N-ethylpyrrolidone, 3-methoxy-N,N-dimethylpropionamide, etc.), other polar solvents (dimethyl sulfoxide, dimethylimidazolidinone, cyclopentane, etc.), water, ester solvents (e.g., propylene glycol monomethyl ether acetate, ethyl acetate, butyl acetate, etc.), acid solvents (e.g., acetic acid, etc.), ether solvents (e.g., tetrahydrofuran, tert-butyl methyl ether, etc.), ketone solvents (e.g., cyclohexanone, cyclopentanone, acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), hydrocarbon solvents (e.g., hexane, heptane, etc.), aromatic solvents (e.g., toluene, etc.), and alkaline solvents (e.g., pyridine, etc.), and alcohol solvents, amide solvents, dimethyl sulfoxide, and dimethylimidazolidinone are preferred. Although the temperature and time cannot be determined uniquely, it is preferred to allow the reaction to proceed at a temperature within a range of 10 to 100° C. for 1 to 24 hours.
[0218] As the metal source, any metal source used in the synthesis of CI Pigment Yellow 129 type compounds can be used without particular limitation, and examples thereof include acetates, halide salts, sulfonates, etc. Furthermore, a ligand such as 8-hydroxyquinoline may be mixed and reacted.
[0219] The hydroxy-substituted aryl aldehyde and hydroxy-substituted aniline having an acid group or a basic group in the synthesis method (i) can be synthesized with reference to, for example, JP-A-2013-510156 or Chemistry-A European Journal 1, 2009, vol. 15, sha-pu 33, p. 8283-8295.
[0220] In the synthesis method (ii), OH, NH 2 , CO 2 H or SO 3 H can be introduced into an azomethine compound in advance and the functional group thereof can be reacted with a compound having an acid group or an amino group.
[0221] The content of compound S 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.
[0222] The content of compound S is preferably 1 to 50 parts by mass relative to 100 parts by mass of the pigment. The lower limit is preferably 3 parts by mass or more, more preferably 50 parts by mass or more, and the upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less.
[0223] <<Resin>>
[0224] The coloring composition of the present invention contains a resin. The resin is blended, for example, for the purpose of dispersing a pigment or the like in the coloring composition or for the purpose of a binder. In addition, a resin used mainly for dispersing a pigment or the like in the coloring composition is referred to as a dispersant. However, these uses of the resin are examples, and the resin can also be used for purposes other than these uses.
[0225] The weight average molecular weight (Mw) of the resin is preferably 2,000 to 2,000,000. The upper limit is preferably 1,000,000 or less, more preferably 500,000 or less. The lower limit is preferably 3,000 or more, more preferably 5,000 or more.
[0226] Examples of the resin include (meth) acrylic resins, epoxy resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamide-imide resins, polyimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, etc. These resins may be used alone or in combination of two or more.
[0227] The coloring composition of the present invention also preferably contains an alkali-soluble resin. Since the coloring composition of the present invention contains an alkali-soluble resin, the desired pattern can be formed by alkaline development. As alkali-soluble resins, resins having acid groups and the like can be cited. As types of acid groups, carboxyl groups, phosphoric acid groups, sulfonic groups, phenolic hydroxyl groups, etc. can be cited. In addition, as a resin having an acid group, a resin in which an acid group is introduced by reacting an acid anhydride with a hydroxyl group generated on epoxy ring opening can also be used. As these resins, the resins described in Japanese Patent Gazette No. 6349629 can be cited. Resins having acid groups can also be used as dispersants. In addition, as alkali-soluble resins, alkali-soluble resins described in Japanese Patent Gazette No. 2017-173787 can also be used.
[0228] The acid value of the alkali-soluble resin 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, further preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
[0229] The coloring composition of the present invention also 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 on the side chain, more preferably a copolymer having a repeating unit having a basic group on the side chain and a repeating unit not containing a basic group, and further preferably a block copolymer having a repeating unit having a basic group on 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. As the basic group contained in the resin having a basic group, a group represented by the following formula (a-1), a group represented by the following formula (a-2), etc. can be mentioned.
[0230] [Chemical formula 13]
[0231]
[0232] In formula (a-1), R a1 and R a2 Each independently represents a hydrogen atom, an alkyl group or an aryl group, and R a1 With R a2 They may be bonded to form a ring.
[0233] In formula (a-2), R a11 represents a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an acyl group or an oxygen free radical, R a12 ~R a19 Each independently represents a hydrogen atom, an alkyl group or an aryl group.
[0234] R a1 , R a2 , R a11 ~R a19 The number of carbon atoms of the alkyl group represented is preferably 1 to 30, more preferably 1 to 15, further preferably 1 to 8, and particularly preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent.
[0235] R a1 , R a2 , R a11 ~R a19 The number of carbon atoms of the aryl group represented is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 12. The aryl group may have a substituent.
[0236] R a11The number of carbon atoms of the alkoxy group represented is preferably 1 to 30, more preferably 1 to 15, further preferably 1 to 8, and particularly preferably 1 to 5. The alkoxy group may have a substituent.
[0237] R a11 The number of carbon atoms of the aryloxy group represented is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 12. The aryloxy group may have a substituent.
[0238] R a11 The number of carbon atoms of the acyl group represented is preferably 2 to 30, more preferably 2 to 20, and further preferably 2 to 12. The acyl group may have a substituent.
[0239] Examples of commercially available resins having a basic group include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (all BYK Japan KK), SOLSPERSE 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (all manufactured by Lubrizol Japan Limited.), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), etc. Furthermore, as the resin having a basic group, the block copolymer (B) described in paragraphs 0063 to 0112 of JP-A-2014-219665 and the block copolymer A1 described in paragraphs 0046 to 0076 of JP-A-2018-156021 can also be used, and these contents are incorporated into this specification.
[0240] The coloring composition of the present invention also preferably contains a resin having an acid group and a resin having a basic group, respectively. According to this embodiment, the storage stability of the coloring composition can be further improved. When a resin having an acid group and a 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 further preferably 50 to 200 parts by mass relative to 100 parts by mass of the resin having an acid group.
[0241] The resin is also preferably 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 dimers”).
[0242] [Chemical formula 14]
[0243]
[0244] In formula (ED1), R 1 and R 2 Each independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 25 carbon atoms.
[0245] [Chemical formula 15]
[0246]
[0247] In formula (ED2), R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. Specific examples of formula (ED2) can be found in Japanese Unexamined Patent Application Publication No. 2010-168539.
[0248] For specific examples of the ether dimer, reference can be made to paragraph 0317 of JP-A-2013-029760, the contents of which are incorporated herein.
[0249] The resin preferably includes a resin containing a repeating unit having a polymerizable group.
[0250] The resin preferably includes a resin containing a repeating unit derived from a compound represented by the formula (X).
[0251] [Chemical formula 16]
[0252]
[0253] In the formula, R 1 represents a hydrogen atom or a methyl group, R 21 and R 22 Each independently represents an alkylene group, and n represents an integer of 0 to 15. 21 and R 22 The number of carbon atoms of the alkylene group represented is preferably 1 to 10, more preferably 1 to 5, further 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 further preferably an integer of 0 to 3.
[0254] Examples of the compound represented by formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylates of p-cumylphenol, and examples of commercially available products include ARONIX M-110 (manufactured by TOAGOSEI CO., LTD.).
[0255] As the resin, it is also preferred 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 included in the main chain of the repeating unit or in the side chain of the repeating unit. The aromatic carboxyl group is preferably included in the main chain of the repeating unit. In addition, in this specification, the aromatic carboxyl group refers to a group having a structure in which one or more carboxyl groups are bonded to an aromatic ring. Among the aromatic carboxyl groups, the number of carboxyl groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
[0256] The resin Ac is preferably a resin containing at least one repeating unit selected from the repeating unit represented by the formula (Ac-1) and the repeating unit represented by the formula (Ac-2).
[0257] [Chemical formula 17]
[0258]
[0259] In formula (Ac-1), Ar 1 represents a group containing an aromatic carboxyl group, L 1 Indicates -COO- or -CONH-, L 2 represents a divalent linking group.
[0260] In formula (Ac-2), Ar 10 represents a group containing an aromatic carboxyl group, L 11 Indicates -COO- or -CONH-, L 12 Represents a trivalent linking group, P 10 Represents a polymer chain.
[0261] As Ar in formula (Ac-1) 1 Examples of the group containing an aromatic carboxyl group include a structure derived from an aromatic tricarboxylic anhydride, a structure derived from an aromatic tetracarboxylic anhydride, etc. Examples of the aromatic tricarboxylic anhydride and the aromatic tetracarboxylic anhydride include compounds of the following structures.
[0262] [Chemical formula 18]
[0263]
[0264] In the above formula, Q 1 It 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).
[0265] [Chemical formula 19]
[0266]
[0267] Ar1 The group containing an aromatic carboxyl group represented by may have a polymerizable group. The polymerizable group is preferably a group containing an ethylenically unsaturated bond and a cyclic ether group, and more preferably a group containing an ethylenically unsaturated bond. 1 Specific examples of the aromatic carboxyl group-containing group represented by include a group represented by the formula (Ar-11), a group represented by the formula (Ar-12), a group represented by the formula (Ar-13), and the like.
[0268] [Chemical formula 20]
[0269]
[0270] In the formula (Ar-11), n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
[0271] In the formula (Ar-12), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and further preferably 2.
[0272] In formula (Ar-13), n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and further preferably 1. However, at least one of n3 and n4 is an integer of 1 or more.
[0273] In the formula (Ar-13), Q 1 It 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).
[0274] In the formulas (Ar-11) to (Ar-13), *1 represents 1 bonding position.
[0275] In formula (Ac-1), L 1 It represents -COO- or -CONH-, and preferably represents -COO-.
[0276] As L in formula (Ac-1) 2 The divalent linking group represented by the above-mentioned may include alkylene, arylene, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and a group formed by combining two or more of these. The number of carbon atoms of the alkylene is preferably 1 to 30, more preferably 1 to 20, and further preferably 1 to 15. The alkylene may be any of a straight chain, a branched chain, and a cyclic chain. The number of carbon atoms of the arylene is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 10. The alkylene and arylene groups may have substituents. As the substituent, a hydroxyl group or the like may be mentioned. L 2 The divalent linking group represented by is preferably -L2a -O- represented group. 2a Examples include alkylene groups; arylene groups; groups formed by combining alkylene groups and arylene groups; groups formed by combining at least one selected from alkylene groups and arylene groups with at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S-, preferably alkylene groups. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, and further preferably 1 to 15. The alkylene group may be any of a linear, branched or cyclic group. The alkylene group and arylene group may have a substituent. Examples of the substituent include a hydroxyl group and the like.
[0277] As Ar in formula (Ac-2) 10 The group containing an aromatic carboxyl group represented by 1 The meanings are the same, and the preferred ranges are also the same.
[0278] In formula (Ac-2), L 11 It represents -COO- or -CONH-, and preferably represents -COO-.
[0279] As L in formula (Ac-2) 12 The trivalent linking group represented by the above-mentioned may include hydrocarbon groups, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and groups formed by combining two or more of these. Examples of the hydrocarbon group 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 further preferably 1 to 15. The aliphatic hydrocarbon group may be any of a straight chain, a branched chain, and a cyclic group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include a hydroxyl group and the like. L 12 The trivalent linking group represented is preferably a group represented by the formula (L12-1), and more preferably a group represented by the formula (L12-2).
[0280] [Chemical formula 21]
[0281]
[0282] In formula (L12-1), L 12b represents a trivalent connecting group, X 1 represents S, and *1 represents L in formula (Ac-2) 11 The bonding position of *2 indicates the bonding position with P of formula (Ac-2). 10 The bonding position of L 12bThe trivalent linking group represented by may be a hydrocarbon group; a group consisting of a hydrocarbon group and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S-, etc., preferably a hydrocarbon group or a group consisting of a hydrocarbon group and -O-.
[0283] In formula (L12-2), L 12c represents a trivalent connecting group, X 1 represents S, and *1 represents L in formula (Ac-2) 11 The bonding position of *2 indicates the bonding position with P of formula (Ac-2). 10 The bonding position of L 12c Examples of the trivalent linking group represented by include a hydrocarbon group; a group consisting of a hydrocarbon group and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S-, and the like, and a hydrocarbon group is preferred.
[0284] In formula (Ac-2), P 10 Represents a polymer chain. 10 The polymer chain represented preferably has at least one repeating unit selected from the group consisting of a poly(meth)acrylic acid repeating unit, a polyether repeating unit, a polyester repeating unit, and a polyol repeating unit. 10 The weight average molecular weight of is preferably 500 to 20,000. The lower limit is preferably 1,000 or more. The upper limit is preferably 10,000 or less, more preferably 5,000 or less, and further preferably 3,000 or less. 10 When the weight average molecular weight is within the above range, the dispersibility of the pigment in the composition is good. In the case where the resin having an aromatic carboxyl group is a resin having a repeating unit represented by formula (Ac-2), the resin can be preferably used as a dispersant.
[0285] The resin preferably contains a resin as a dispersant. As the dispersant, an acidic dispersant (acidic resin) and an alkaline dispersant (alkaline resin) can be cited. Here, the acidic dispersant (acidic resin) refers to a resin in which the amount of acid groups is greater than the amount of alkaline groups. As an acidic dispersant (acidic resin), when the total amount of the amount of acid groups and the amount of alkaline groups is set to 100 mol%, a resin in which the amount of acid groups is 70 mol% or more is preferred. The acid group possessed by 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. In addition, an alkaline dispersant (alkaline resin) refers to a resin in which the amount of alkaline groups is greater than the amount of acid groups. As an alkaline dispersant (alkaline resin), when the total amount of the amount of acid groups and the amount of alkaline groups is set to 100 mol%, a resin in which the amount of alkaline groups exceeds 50 mol%. The basic group possessed by the alkaline dispersant is preferably an amino group.
[0286] The resin used as the dispersant is also preferably a grafted resin. For details of the grafted resin, reference can be made to paragraphs 0025 to 0094 of JP-A-2012-255128, and the contents are incorporated into this specification.
[0287] 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 the above-mentioned resins.
[0288] The resin used as a 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 a polyimine-based dispersant, a resin having a main chain and a side chain and having a basic nitrogen atom in at least one of the main chain and the side chain is preferred, wherein the main chain contains a partial structure having a functional group with a pKa of less than 14, and the number of atoms in the side chain is 40 to 10,000. There is no particular limitation on the basic nitrogen atom as long as it is a basic nitrogen atom. For polyimine-based dispersants, reference can be made to paragraphs 0022 to 0097 of Japanese Patent Publication No. 2009-203462 and paragraphs 0102 to 0166 of Japanese Patent Publication No. 2012-255128, and these contents are incorporated into this specification.
[0289] The resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core. Examples of such resins include dendritic polymers (including star polymers). Specific examples of dendritic polymers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of Japanese Patent Application Publication No. 2013-043962.
[0290] The resin used as a dispersant is also preferably a resin containing a repeating unit having a group containing an ethylenically unsaturated bond on the side chain. The content of the repeating unit having a group containing an ethylenically unsaturated bond on the side chain is preferably 10 mol% or more in all repeating units of the resin, more preferably 10 to 80 mol%, and further preferably 20 to 70 mol%. In addition, the dispersant can also use the resin described in Japanese Patent Publication No. 2018-087939.
[0291] The dispersant can also be obtained as a commercial product, and specific examples thereof include DISPERBYK series manufactured by BYK Japan KK, SOLSPERSE series manufactured by Lubrizol Japan Limited., Efka series manufactured by BAS F, and AJISPER series manufactured by Ajinomoto Fine-Techno Co., Inc. In addition, the product described in paragraph 0129 of Japanese Patent Application Laid-Open No. 2012-137564 and the product described in paragraph 0235 of Japanese Patent Application Laid-Open No. 2017-194662 can also be used as a dispersant.
[0292] Furthermore, as the resin used as the dispersant, the block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077 can also be used.
[0293] The content of the resin in the total solid content 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, further 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.
[0294] The content of the dispersant is preferably 10 to 100 parts by mass relative to 100 parts by mass of the pigment. The lower limit is preferably 15 parts by mass or more, more preferably 20 parts by mass or more, and the upper limit is preferably 80 parts by mass or less, more preferably 60 parts by mass or less.
[0295] The colored composition of the present invention may contain only one resin or two or more resins. When containing two or more resins, the total amount thereof is preferably within the above range.
[0296] <<Solvent>>
[0297] The coloring composition of the present invention contains a solvent. As the solvent, an organic solvent can be mentioned. The type of solvent is basically not particularly limited as long as it satisfies the solubility of each component or the coating property of the composition. As organic solvents, ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents, etc. can be mentioned. For details of these, reference can be made to paragraph 0223 of International Publication No. 2015 / 166779, and the content is incorporated into this specification. In addition, cyclic alkyl substituted ester solvents and cyclic alkyl substituted ketone solvents can also be preferably used. Specific examples of organic solvents include polyethylene glycol monomethyl ether, methylene chloride, 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-dimethylpropionamide, 3-butoxy-N, N-dimethylpropionamide, propylene glycol diacetate, 3-methoxybutanol, etc. However, it is sometimes preferable to reduce the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents for reasons such as environmental aspects (for example, it can be set to 50 mass ppm (parts per million) or less, or 10 mass ppm or less, or 1 mass ppm or less relative to the total amount of the organic solvent).
[0298] In the present invention, it is preferred to use an organic solvent with a low metal content, and the metal content of the organic solvent is preferably 10 mass ppb (parts per billion) or less. If necessary, an organic solvent of mass ppt (parts per trillion) level can be used, such as provided by Toyo Gosei Co., Ltd. (Chemical Industry Daily, November 13, 2015).
[0299] As a method for removing impurities such as metals from an organic solvent, for example, distillation (molecular distillation or thin film distillation, etc.) or filtering using a filter can be cited. The filter pore size of the filter used in the filtration is preferably 10 μm or less, more preferably 5 μm or less, and further preferably 3 μm or less. The material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
[0300] The organic solvent may contain isomers (compounds having the same number of atoms but different structures), and may contain only one isomer or a plurality of isomers.
[0301] The content of the peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially no peroxide is contained.
[0302] 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.
[0303] Furthermore, from the perspective of environmental regulation, the coloring composition of the present invention is preferably substantially free of environmentally regulated substances. In addition, in the present invention, being substantially free of 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, etc. These are registered as environmentally regulated substances in accordance with REACH (Registration Evaluation Authorization and Restriction of CHemicals) regulation, PRTR (Pollutant Release and Transfer Register) law, VOC (Volatile Organic Compounds) regulation, etc., and the amount of use and treatment methods are strictly regulated. These compounds are sometimes used as solvents when manufacturing the various components used in the coloring composition, and sometimes are mixed into the coloring composition as residual solvents. From the perspective of human safety and environmental considerations, it is preferred to reduce these substances as much as possible. As a method for reducing environmentally controlled substances, there can be cited a method of heating and reducing the system to a boiling point above the environmentally controlled substances and distilling and removing the environmentally controlled substances from the system to reduce the substances. In addition, when a small amount of environmentally controlled substances are distilled and removed, it is also effective to azeotropize with a solvent having the same boiling point as the solvent in order to improve efficiency. In addition, when containing a compound with free radical polymerizability, in order to suppress the free radical polymerization reaction during the reduced pressure distillation and remove crosslinking between molecules, a polymerization inhibitor can be added and reduced pressure distillation can be removed. These distillation removal methods can be carried out at any stage, such as the stage of the product of the raw material reaction (such as the resin solution and the multifunctional monomer solution after polymerization) or the stage of the coloring composition made by mixing these compounds.
[0304] <<Other pigment derivatives>>
[0305] The coloring composition of the present invention can contain pigment derivatives (hereinafter, also referred to as other pigment derivatives) other than the above-mentioned compound S. As other pigment derivatives, compounds having a structure in which an acid group or a basic group is bonded to the pigment skeleton can be cited. As the pigment skeleton constituting the pigment derivative, quinoline pigment skeleton, benzimidazolone pigment skeleton, benzisoindole pigment skeleton, benzothiazole pigment skeleton, imine pigment skeleton, squaric acid pigment skeleton, crotonium pigment skeleton, oxonol pigment skeleton, pyrrolopyrrole pigment skeleton, diketopyrrolopyrrole pigment skeleton, azo pigment skeleton, phthalocyanine pigment skeleton, naphthalocyanine pigment skeleton, anthraquinone pigment skeleton, quinacridone pigment skeleton, dioxazine pigment skeleton, pyrene pigment skeleton, perylene pigment skeleton, thioindigo pigment skeleton, isoindoline pigment skeleton, isoindolinone pigment skeleton, quinophthalone pigment skeleton, imine pigment skeleton, dithiol pigment skeleton, triarylmethane pigment skeleton, pyrromethene pigment skeleton, etc. can be cited. Examples of the acid group include a sulfonic acid group, a carboxyl group, a phosphoric acid group, and salts thereof. Examples of the atom or atom group constituting the salt include an alkali metal ion (Li + 、Na + , K + etc.), alkaline earth metal ions (Ca 2+ Mg 2+ As the basic group, there can be mentioned amino group, salt of ammonium group and phthalimide methyl group. As the atom or atomic group constituting the salt, there can be mentioned hydroxide ion, halogen ion, carboxylate ion, sulfonate ion, phenoxide ion and the like.
[0306] As other pigment derivatives, a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative) may be contained. The maximum value (εmax) of the molar absorption coefficient of the transparent pigment derivative in the wavelength region of 400 to 700 nm is preferably 3000 L·mol -1 cm -1 Below, more preferably 1000 L·mol -1 cm -1 Below, more preferably 100 L·mol -1 cm -1 The lower limit of εmax is, for example, IL·mol -1 cm -1 Above, it can also be 10L·mol -1 cm -1 above.
[0307] Specific examples of other pigment derivatives include compounds described in the examples described below, Japanese Patent Application Laid-Open No. 56-118462, Japanese Patent Application Laid-Open No. 63-264674, Japanese Patent Application Laid-Open No. 01-217077, Japanese Patent Application Laid-Open No. 03-009961, Japanese Patent Application Laid-Open No. 03-026767, Japanese Patent Application Laid-Open No. 03-153780, Japanese Patent Application Laid-Open No. 03-045662, Japanese Patent Application Laid-Open No. 04-285669, Japanese Patent Application Laid-Open No. 06-145546, Japanese Patent Application Laid-Open No. 06-212088, Japanese Patent Application Laid-Open No. 06-240158, Japanese Patent Application Laid-Open No. 10-030063, Japanese Patent Application Laid-Open No. 10-195326, International Publication No. Paragraphs 0086 to 0098 of International Publication No. 2011 / 024896, paragraphs 0063 to 0094 of International Publication No. 2012 / 102399, paragraph 0082 of International Publication No. 2017 / 038252, paragraph 0171 of Japanese Patent Application Publication No. 2015-151530, paragraphs 0162 to 0183 of Japanese Patent Application Publication No. 2011-252065, and paragraphs 0171 of Japanese Patent Application Publication No. 2015-151530 Compounds described in Japanese Patent Application Laid-Open No. 2003-081972, Japanese Patent No. 5299151, Japanese Patent Application Laid-Open No. 2015-172732, Japanese Patent Application Laid-Open No. 2014-199308, Japanese Patent Application Laid-Open No. 2014-085562, Japanese Patent Application Laid-Open No. 2014-035351, and Japanese Patent Application Laid-Open No. 2008-081565.
[0308] The content of other pigment derivatives is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, further preferably 15 parts by mass or less, and particularly preferably 10 parts by mass or less, based on 100 parts by mass of the pigment.
[0309] Furthermore, the content of other pigment derivatives is preferably 0.01 to 100 parts by mass, more preferably 0.1 to 10 parts by mass, and even more preferably 0.2 to 5 parts by mass, relative to 1 part by mass of the compound S.
[0310] Furthermore, the total content of other pigment derivatives and the above-mentioned compound S is preferably 1 to 30 parts by mass relative to 100 parts by mass of the pigment. The lower limit is preferably 2 parts by mass or more, more preferably 3 parts by mass or more. The upper limit is preferably 20 parts by mass or less, more preferably 15 parts by mass or less.
[0311] Other pigment derivatives may be used alone or in combination of two or more. When two or more are used in combination, the total amount thereof is preferably within the above range.
[0312] <<Infrared absorber>>
[0313] The coloring composition of the present invention can further contain an infrared absorber. For example, when the coloring composition of the present invention is used to form an infrared transmission filter, the wavelength of 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 700nm. The infrared absorber is preferably a compound having a maximum absorption wavelength in the range of more than 700nm and less than 1800nm. In addition, the absorbance A of the infrared absorber at a wavelength of 500nm is preferably 0.1%. 1 and the absorbance A at the maximum absorption wavelength 2 Ratio A 1 / A 2 It is preferably 0.08 or less, and more preferably 0.04 or less.
[0314] Examples of infrared absorbers include pyrrolopyrrole compounds, cyanine compounds, squaryl compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanidin compounds, crotonium compounds, oxonol compounds, imine compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, azomethine compounds, anthraquinone compounds, bisbenzofuranone compounds, dithiol metal complexes, metal oxides, metal borides, etc. Examples of pyrrolopyrrole compounds include compounds described in paragraphs 0016 to 0058 of Japanese Unexamined Patent Application Publication No. 2009-263614, compounds described in paragraphs 0037 to 0052 of Japanese Unexamined Patent Application Publication No. 2011-068731, and compounds described in paragraphs 0010 to 0033 of International Publication No. 2015 / 166873. Examples of the squaric acid compound include compounds described in paragraphs 0044 to 0049 of Japanese Patent Publication No. 2011-208101, compounds described in paragraphs 0060 to 0061 of Japanese Patent Publication No. 6065169, compounds described in paragraph 0040 of International Publication No. 2016 / 181987, compounds described in Japanese Patent Publication No. 2015-176046, and compounds described in paragraph 0072 of International Publication No. 2016 / 190162. , the compounds described in paragraphs 0196 to 0228 of Japanese Patent Application Publication No. 2016-074649, the compounds described in paragraph 0124 of Japanese Patent Application Publication No. 2017-067963, the compounds described in International Publication No. 2017 / 135359, the compounds described in Japanese Patent Application Publication No. 2017-114956, the compounds described in Japanese Patent No. 6197940, the compounds described in International Publication No. 2016 / 120166, etc. Examples of cyanine compounds include compounds described in paragraphs 0044 to 0045 of Japanese Patent Application Laid-Open No. 2009-108267, compounds described in paragraphs 0026 to 0030 of Japanese Patent Application Laid-Open No. 2002-194040, compounds described in Japanese Patent Application Laid-Open No. 2015-172004, compounds described in Japanese Patent Application Laid-Open No. 2015-172102, compounds described in Japanese Patent Application Laid-Open No. 2008-088426, compounds described in paragraph 0090 of International Publication No. 2016 / 190162, compounds described in Japanese Patent Application Laid-Open No. 2017-031394, etc. Examples of crotonium compounds include compounds described in Japanese Patent Application Laid-Open No. 2017-082029.As the imine compound, for example, there can be mentioned the compounds described in JP-A-2008-528706, the compounds described in JP-A-2012-012399, the compounds described in JP-A-2007-092060, and the compounds described in paragraphs 0048 to 0063 of International Publication No. 2018 / 043564. As the phthalocyanine compound, there can be mentioned the compounds described in paragraph 0093 of JP-A-2012-077153, the oxytitanium phthalocyanine described in JP-A-2006-343631, the compounds described in paragraphs 0013 to 0029 of JP-A-2013-195480, and the vanadium phthalocyanine compounds described in Japanese Patent No. 6081771. As naphthalocyanine compounds, compounds described in paragraph 0093 of Japanese Patent Publication No. 2012-077153 can be cited. As disulfide metal complexes, compounds described in Japanese Patent Publication No. 5733804 can be cited. As metal oxides, for example, indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, tungsten oxide, etc. can be cited. For details of tungsten oxide, reference can be made to paragraph 0080 of Japanese Patent Publication No. 2016-006476, which is incorporated into this specification. As metal borides, lanthanum boride and the like can be cited. As commercially available products of lanthanum boride, LaB6-F (manufactured by JAPAN NEW METALS CO., LTD) and the like can be cited. In addition, as metal borides, compounds described in International Publication No. 2017 / 119394 can also be used. Examples of commercially available products of indium tin oxide include F-ITO (manufactured by DOWA HOLDINGS CO., LTD.).
[0315] Furthermore, as the infrared absorber, the squaric acid compounds described in Japanese Patent Application Publication No. 2017-197437, the squaric acid compounds described in Japanese Patent Application Publication No. 2017-025311, the squaric acid compounds described in International Publication No. 2016 / 154782, the squaric acid compounds described in Japanese Patent No. 5884953, the squaric acid compounds described in Japanese Patent No. 6036689, The squaryl acid compound described in Japanese Patent No. 5810604, the squaryl acid compound described in paragraphs 0090 to 0107 of International Publication No. 2017 / 213047, the pyrrole ring-containing compound described in paragraphs 0019 to 0075 of Japanese Patent Application Publication No. 2018-054760, the pyrrole ring-containing compound described in paragraphs 0078 to 0082 of Japanese Patent Application Publication No. 2018-040955, the The pyrrole ring-containing compound described in paragraphs 0043 to 0069 of JP-A-2018-002773, the squarylium compound having an aromatic ring at the amide α position described in paragraphs 0024 to 0086 of JP-A-2018-041047, the amide-linked squarylium compound described in JP-A-2017-179131, the pyrrole bi-squarylium compound described in JP-A-2017-141215 A compound having a skeleton or a crotonium skeleton, a dihydroxycarbazole bis-type square acid compound described in Japanese Patent Publication No. 2017-082029, an asymmetric compound described in paragraphs 0027 to 0114 of Japanese Patent Publication No. 2017-068120, a pyrrole ring-containing compound (carbazole type) described in Japanese Patent Publication No. 2017-067963, a phthalocyanine compound described in Japanese Patent No. 6251530, etc.
[0316] 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 further 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 infrared absorber or two or more infrared absorbers. When containing two or more infrared absorbers, the total amount is preferably within the above range.
[0317] <<Polymerizable compounds>>
[0318] The coloring composition of the present invention can contain a polymerizable compound. As the polymerizable compound, a known compound that can be cross-linked by free radicals, acid, or heat can be used. In the present invention, the polymerizable compound is preferably a compound having a group containing an ethylenically unsaturated bond. As the group containing an ethylenically unsaturated bond, vinyl, (meth) allyl, (meth) acryloyl, etc. can be cited. The polymerizable compound used in the present invention is preferably a free radical polymerizable compound.
[0319] The polymerizable compound may be in any chemical form such as a monomer, a prepolymer, or an oligomer, but preferably a monomer. The molecular weight of the polymerizable compound is preferably 100 to 3000. The upper limit is more preferably 2000 or less, and further preferably 1500 or less. The lower limit is more preferably 150 or more, and further preferably 250 or more.
[0320] The polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and further preferably a compound containing 3 to 6 ethylenically unsaturated bond-containing groups. Furthermore, the polymerizable compound is preferably a tri- to penta-functional (meth)acrylate compound, and more preferably a tri- to hexa-functional (meth)acrylate compound. Specific examples of the polymerizable compound include compounds described in paragraphs 0095 to 0108 of JP-A-2009-288705, paragraph 0227 of JP-A-2013-029760, paragraphs 0254 to 0257 of JP-A-2008-292970, paragraphs 0034 to 0038 of JP-A-2013-253224, paragraph 0477 of JP-A-2012-208494, JP-A-2017-048367, Japanese Patent No. 6057891, and Japanese Patent No. 6031807, and the contents thereof are incorporated into the present specification.
[0321] Preferred polymerizable compounds include dipentaerythritol triacrylate (commercially available as KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (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, compounds manufactured by SARTOMER Company, Inc., and commercially available SR454 and SR499). In addition, as the polymerizable compound, diglycerol 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., KAYARADHDDA), 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.), 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 (all manufactured by TAISEI FINE CHEMICAL CO., LTD.), LIGHT ACRYLATE POB-A0 (manufactured by KYOEISHA CHEMICAL CO., LTD.), etc.
[0322] Furthermore, 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, isocyanuric acid ethylene oxide-modified tri(meth)acrylate, and pentaerythritol tri(meth)acrylate can also be used. Commercially available products of the trifunctional (meth)acrylate compound include ARONIX M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305, M-303, M-452, and 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, and TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, and PET-30 (manufactured by Nippon Kayaku Co., Ltd.).
[0323] Furthermore, a compound having an acid group can also be used as a polymerizable compound. By using a polymerizable compound having an acid group, the polymerizable compound of the unexposed part can be easily removed during development, thereby suppressing the generation of development residues. Examples of the acid group include a carboxyl group, a sulfonic group, a phosphoric acid group, and the like, preferably a carboxyl group. Examples of polymerizable compounds having an acid group include succinic acid-modified dipentaerythritol penta(meth)acrylate, and the like. Commercially available products of polymerizable compounds having an acid group include ARONIX M-510, M-520, and 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, and 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 production or handling.
[0324] Furthermore, 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, and DPCA-120 (all manufactured by Nippon Kayaku Co., Ltd.).
[0325] Furthermore, a polymerizable compound having an alkyleneoxy group can also be used as a polymerizable compound. 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 further preferably a tri- to hexa-functional (meth)acrylate compound having 4 to 20 ethyleneoxy groups. Commercially available polymerizable compounds having an alkyleneoxy group include, for example, SR-494 manufactured by Sartomer Company, Inc., which is a tetrafunctional (meth)acrylate having 4 ethyleneoxy groups, and KAYARAD TPA-330, which is a trifunctional (meth)acrylate having 3 isobutyleneoxy groups.
[0326] Furthermore, a polymerizable compound having a fluorene skeleton can also be used as the polymerizable compound. Examples of commercially available polymerizable compounds having a fluorene skeleton include OGSOL FA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., a (meth)acrylate monomer having a fluorene skeleton).
[0327] As the polymerizable compound, it is also preferable to use a compound that does not substantially contain environmentally regulated substances such as toluene. Examples of commercially available products of such a compound include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
[0328] The content of the polymerizable compound in the total solid content 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 more preferably 1% by mass or more. The upper limit is more preferably 45% by mass or less, and more preferably 40% by mass or less. The polymerizable compound may be a single species or a combination of two or more species. When two or more species are used in combination, the total of these is preferably within the above range.
[0329] <<Polymerization initiator>>
[0330] The coloring composition of the present invention may contain a polymerization initiator. Examples of the polymerization initiator include photopolymerization initiators and thermal polymerization initiators, and photopolymerization initiators are preferred. Furthermore, the polymerization initiator is preferably a radical polymerization initiator.
[0331] Examples of the thermal polymerization initiator include azo compounds such as 2,2′-azobisisobutyronitrile (ATBN), 3-carboxypropionitrile, azobismalononitrile, and dimethyl-(2,2′)-azobis(2-propionate methyl ester); and organic peroxides such as tert-butylperbenzoic acid, benzoyl peroxide, lauroyl peroxide, and potassium persulfate.
[0332] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, sulfur compounds, ketone compounds, aromatic onium salts, α-hydroxyketone compounds, α-aminoketone compounds, etc. 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 the group consisting of an oxime compound, an α-hydroxyketone compound, an α-aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound. In addition, as photopolymerization initiators, there can be cited paragraphs 0065 to 0111 of Japanese Patent Gazette No. 2014-130173, compounds described in Japanese Patent Gazette No. 6301489, peroxide-based photopolymerization initiators described in MATERIAL STAGE 37 to 60p, vol. 19, No. 3, 2019, photopolymerization initiators described in International Publication No. 2018 / 221177, photopolymerization initiators described in International Publication No. 2018 / 110179, photopolymerization initiators described in Japanese Patent Gazette No. 2019-043864, and photopolymerization initiators described in Japanese Patent Gazette No. 2019-044030, and these contents are incorporated into this specification.
[0333] Examples of commercially available α-hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacure 2959, and Irgacure 127 (all manufactured by BASF). Examples of commercially available α-aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, and Omnirad 379EG (all manufactured by IGM Resins BV), Irgacure 907, Irgacure 369, Irgacure 369E, and Irgacure 379EG (all manufactured by BASF). Examples of commercially available products of the acylphosphine compound include Omnirad 819 and Omnirad TPO (both manufactured by IGM Resins BV), Irgacure 819 and Irgacure TPO (both manufactured by BASF).
[0334] 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 JCS Perkin II (1979, pp. 1653-1660), compounds described in JCS Perkin II (1979, pp. 156-162), and compounds described in Journal of Photopolymer Science and Technology. Technology (1995, pp. 202-232), compounds described in Japanese Patent Application Publication No. 2000-066385, compounds described in Japanese Patent Application Publication No. 2004-534797, compounds described in Japanese Patent Application Publication No. 2017-019766, compounds described in Japanese Patent No. 6065596, compounds described in International Publication No. 2015 / 152153, compounds described in International Publication No. 2017 / 051680, compounds described in Japanese Patent Application Publication No. 2017-198865, compounds described in paragraphs 0025 to 0038 of International Publication No. 2017 / 164127, compounds described in International Publication No. 2013 / 167515, etc. Specific examples of oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropane-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3-(4-toluenesulfonyloxy)iminobutane-2-one and 2-ethoxycarbonyloxyimino-1-phenylpropane-1-one. As commercial products, Irgacure-OXE01, Irgacure-OXE02, Irgacure-OXE03, Irgacure-OXE04 (all manufactured by BASF), TR-PBG-304 (manufactured by Changzhou Tronly New Electronic Materials CO., LTD.), Adeka Optomer N-1919 (manufactured by ADEKA CORPORATION, photopolymerization initiator 2 described in Japanese Patent Publication No. 2012-014052). In addition, as oxime compounds, non-coloring compounds or compounds with high transparency and low color change are also preferably used. As commercial products, ADEKA ARKLS NCI-730, NCI-831, NCI-930 (all manufactured by ADEKA CORPORATION) and the like can be mentioned.
[0335] 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 compounds described in JP-A-2014-137466.
[0336] As the photopolymerization initiator, an oxime compound having a skeleton in which at least one benzene ring in a carbazole ring is a naphthalene ring can also be used. Specific examples of such oxime compounds include compounds described in International Publication No. 2013 / 083505.
[0337] 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 compounds described in JP-A-2010-262028, compounds 24, 36 to 40 described in JP-A-2014-500852, and compound (C-3) described in JP-A-2013-164471.
[0338] As the photopolymerization initiator, an oxime compound having a nitro group can be used. The oxime compound having a nitro group is also preferably a dimer. As specific examples of the oxime compound having a nitro group, there can be cited the compounds described in paragraphs 0031 to 0047 of Japanese Patent Publication No. 2013-114249, paragraphs 0008 to 0012 and 0070 to 0079 of Japanese Patent Publication No. 2014-137466, the compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, and ADEKA ARKLS NCI-831 (manufactured by ADEKA CORPORAT [ON).
[0339] As the photopolymerization initiator, an oxime compound having a benzofuran skeleton can also be used. Specific examples thereof include OE-01 to OE-75 described in International Publication No. 2015 / 036910.
[0340] As a photopolymerization initiator, an oxime compound having a substituent having a hydroxyl group bonded to a carbazole skeleton can also be used. As these photopolymerization initiators, compounds described in International Publication No. 2019 / 088055 can be cited.
[0341] As the photopolymerization initiator, an aromatic ring group Ar having an electron-withdrawing group introduced into the aromatic ring can also be used. OX1 As the aromatic ring group Ar OX1The electron withdrawing group may include acyl, nitro, trifluoromethyl, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, and cyano. Acyl and nitro are preferred. Acyl is more preferred because it is easy to form a film with excellent light resistance, and benzoyl is further preferred. The benzoyl may have a substituent. As a substituent, a halogen atom, cyano, nitro, hydroxyl, alkyl, alkoxy, aryl, aryloxy, heterocyclic group, heterocyclic oxygen group, alkenyl, alkylsulfanyl, arylsulfanyl, acyl or amino is preferred. An alkyl, alkoxy, aryl, aryloxy, heterocyclic oxygen group, alkylsulfanyl, arylsulfanyl or amino is more preferred. An alkoxy, alkylsulfanyl or amino is further preferred.
[0342] The oxime compound OX is preferably at least one selected from the group consisting of a compound represented by the formula (OX1) and a compound represented by the formula (OX2), and is more preferably a compound represented by the formula (OX2).
[0343] [Chemical formula 22]
[0344]
[0345] In the formula, R X1 represents an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclicoxy group, an alkylsulfanyl group, an arylsulfanyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an acyloxy group, an amino group, a phosphonyl group, a carbamoyl group or a sulfamoyl group,
[0346] R X2 represents an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclicoxy group, an alkylsulfanyl group, an arylsulfanyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyloxy group or an amino group,
[0347] R X3 ~R X14 each independently represents a hydrogen atom or a substituent;
[0348] Among them, R X10 ~R X14 At least one of them is an electron withdrawing group.
[0349] In the above formula, R X1 It is preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group or a heterocyclic group, more preferably an alkyl group, an aryl group or a heterocyclic group, and still more preferably an alkyl group. X2 An alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic group or an acyloxy group is preferred, an alkyl group, an alkenyl group, an aryl group or a heterocyclic group is more preferred, and an alkyl group is further preferred.
[0350] In the above formula, R X3 ~R X14Each independently represents a hydrogen atom or a substituent.
[0351] R X3 ~R X5 Preferably, each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclicoxy group, an alkylsulfanyl group, an arylsulfanyl group, an acyl group or an amino group; more preferably, it represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group, an aryl group or a heterocyclic group; further preferably, it represents a hydrogen atom, a nitro group, an alkyl group or an aryl group; and particularly preferably, it represents a hydrogen atom.
[0352] R X6 ~R X10 Preferably, each of them is independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclicoxy group, an alkylsulfanyl group, an arylsulfanyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an amino group, a group represented by the formula (OR-11), or a group represented by the formula (OR-12); more preferably, it is a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an aryl group, a heterocyclic group, or an amino group; further preferably, it is a hydrogen atom, a cyano group, an alkyl group, or an aryl group; further preferably, it is a hydrogen atom, an alkyl group, or an aryl group; further preferably, it is a hydrogen atom, an alkyl group, or an aryl group; further preferably, it is a hydrogen atom or an alkyl group; and particularly preferably, it is a hydrogen atom.
[0353] [Chemical formula 23]
[0354]
[0355] In the formula, R OX11 represents an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclicoxy group, an alkylsulfanyl group, an arylsulfanyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an acyloxy group, an amino group, a phosphonyl group, a carbamoyl group or a sulfamoyl group,
[0356] R OX12 represents an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group,
[0357] an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyloxy group or an amino group,
[0358] Wavy lines represent bonding bonds.
[0359] R X10 ~R X14 The substituent represented is preferably a nitro group, a halogen atom, a cyano group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkenyl group, an alkylsulfanyl group, an arylsulfanyl group, an acyl group or an amino group. X10 ~R X14 At least one of them is an electron withdrawing group.
[0360] As R X10 ~R X14 The electron withdrawing group represented may include acyl, nitro, trifluoromethyl, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, and cyano. Acyl and nitro are preferred. Acyl is more preferred, and benzoyl is further preferred because it is easy to form a film with excellent light resistance. Benzoyl may have a substituent. As a substituent, a halogen atom, cyano, nitro, hydroxyl, alkyl, alkoxy, aryl, aryloxy, heterocyclic group, heterocyclic oxygen group, alkenyl, alkylsulfanyl, arylsulfanyl, acyl or amino is preferred. An alkyl, alkoxy, aryl, aryloxy, heterocyclic oxygen group, alkylsulfanyl, arylsulfanyl or amino is more preferred. An alkoxy, alkylsulfanyl or amino is further preferred.
[0361] In the above formula, R X12 is an electron-withdrawing group, R X10 , R X11 , R X13 , R X14 Preferred is a hydrogen atom.
[0362] Specific examples of the oxime compound OX include compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600.
[0363] Specific examples of the oxime compound preferably used in the present invention are shown below, but the present invention is not limited to these.
[0364] [Chemical formula 24]
[0365]
[0366] [Chemical formula 25]
[0367]
[0368] [Chemical formula 26]
[0369]
[0370] [Chemical formula 27]
[0371]
[0372] [Chemical formula 28]
[0373]
[0374] The oxime compound preferably has a maximum absorption wavelength in the range of wavelength 350 to 500 nm, and more preferably has a maximum absorption wavelength in the range of wavelength 360 to 480 nm. In addition, from the viewpoint of sensitivity, the molar absorption coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1000 to 300000, further preferably 2000 to 300000, and particularly preferably 5000 to 200000. The molar absorption coefficient of the compound can be measured using a known method. For example, it is preferably measured using a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian) using an ethyl acetate solvent at a concentration of 0.01 g / L.
[0375] As the photopolymerization initiator, it is also preferable to use Irgacure OXE01 (manufactured by BASF) and / or Irgacure OXE02 (manufactured by BASF) and Omnirad 2959 (manufactured by IGM Resins BV) in combination.
[0376] As the photopolymerization initiator, a difunctional or trifunctional or higher photoradical polymerization initiator can be used. By using these photoradical polymerization initiators, two or more free radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained. In addition, when using a compound with an asymmetric structure, the crystallinity decreases and the solubility in solvents is improved, and it is not easy to precipitate over time, thereby improving the temporal stability of the coloring composition. Specific examples of the bifunctional or trifunctional or higher-functional photoradical polymerization initiator include dimers of oxime compounds described in JP-T 2010-527339, JP-T 2011-524436, International Publication No. 2015 / 004565, paragraphs 0407 to 0412 of JP-T 2016-532675, and paragraphs 0039 to 0055 of International Publication No. 2017 / 033680, and compound (E) described in JP-T 2013-522445. and compound (G), Cmpd1 to 7 described in International Publication No. 2016 / 034963, the oxime ester photoinitiator described in paragraph 0007 of Japanese Patent Publication No. 2017-523465, the photoinitiator described in paragraphs 0020 to 0033 of Japanese Patent Publication No. 2017-167399, the photopolymerization initiator (A) described in paragraphs 0017 to 0026 of Japanese Patent Publication No. 2017-151342, the oxime ester photoinitiator described in Japanese Patent No. 6469669, etc.
[0377] The content of the polymerization initiator 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, and more preferably 1% by mass or more. The upper limit is preferably 20% by mass or less, and more preferably 15% by mass or less. In the coloring composition of the present invention, only one polymerization initiator may be used, or two or more polymerization initiators may be used. When two or more polymerization initiators are used, the total is preferably within the above range.
[0378] <<Compounds having a cyclic ether group>>
[0379] The coloring composition of the present invention can contain a compound having a cyclic ether group. As the cyclic ether group, an epoxy group, an oxetane group, etc. can be cited. The compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter, also referred to as an epoxy compound). As an epoxy compound, the compounds described in paragraphs 0034 to 0036 of Japanese Patent Publication No. 2013-011869, paragraphs 0147 to 0156 of Japanese Patent Publication No. 2014-043556, and paragraphs 0085 to 0092 of Japanese Patent Publication No. 2014-089408, and the compounds described in Japanese Patent Publication No. 2017-179172 can also be used. These contents are incorporated into this specification.
[0380] The epoxy compound may be a low molecular weight compound (e.g., a molecular weight of less than 2000, and further a molecular weight of less than 1000), or a high molecular weight compound (macromolecule) (e.g., a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more). The weight average molecular weight of the epoxy compound is preferably 200 to 100000, and more preferably 500 to 50000. The upper limit of the weight average molecular weight is preferably 10000 or less, more preferably 5000 or less, and further preferably 3000 or less.
[0381] As the epoxy compound, an epoxy resin can be preferably used. Examples of the epoxy resin include epoxy resins that are glycidyl ethers of phenolic compounds, epoxy resins that are glycidyl ethers of various novolac resins, alicyclic epoxy resins, aliphatic epoxy resins, heterocyclic epoxy resins, glycidyl ester epoxy resins, glycidyl amine epoxy resins, epoxy resins obtained by glycidylating halogenated phenols, condensates of silicon compounds having epoxy groups and other silicon compounds, copolymers of polymerizable unsaturated compounds having epoxy groups and other polymerizable unsaturated compounds, etc. The epoxy equivalent of the epoxy resin is preferably 310 to 3300 g / eq, more preferably 310 to 1700 g / eq, and even more preferably 310 to 1000 g / eq.
[0382] Commercially available products of the compound having a cyclic ether group include, for example, EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DIC CORPORATION), Marproof G-015OM, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (these are polymers manufactured by NOFCORPORATION and contain an epoxy group).
[0383] 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 0.5% by mass or more, and more preferably 1% by mass or more. The upper limit is preferably 15% by mass or less, and more preferably 10% by mass or less. The compound having a cyclic ether group may be only one or more than two. In the case of two or more, it is preferred that the total is within the above range.
[0384] <<Curing accelerator>>
[0385] The coloring composition of the present invention may contain a curing accelerator. Examples of the curing accelerator include thiol compounds, hydroxymethyl 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 compounds described in paragraphs 0094 to 0097 of International Publication No. 2018 / 056189, compounds described in paragraphs 0246 to 0253 of Japanese Patent Application Publication No. 2015-034963, compounds described in paragraphs 0186 to 0251 of Japanese Patent Application Publication No. 2013-041165, and compounds described in Japanese Patent Application Publication No. 2014-055114. Ionic compounds, compounds described in paragraphs 0071 to 0080 of Japanese Patent Application Laid-Open No. 2012-150180, alkoxysilane compounds having an epoxy group described in Japanese Patent Application Laid-Open No. 2011-253054, compounds described in paragraphs 0085 to 0092 of Japanese Patent Application Laid-Open No. 5765059, carboxyl group-containing epoxy curing agents described in Japanese Patent Application Laid-Open No. 2017-036379, etc. 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.
[0386] <<Ultraviolet light absorber>>
[0387] The coloring composition of the present invention may contain an ultraviolet absorber. The ultraviolet absorber may include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, etc. As these compounds, there may be mentioned the compounds described in paragraphs 0038 to 0052 of Japanese Patent Application Publication No. 2009-217221, paragraphs 0052 to 0072 of Japanese Patent Application Publication No. 2012-208374, paragraphs 0317 to 0334 of Japanese Patent Application Publication No. 2013-068814, and paragraphs 0061 to 0080 of Japanese Patent Application Publication No. 2016-162946, and these contents are incorporated into this specification. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by DAITO CHEMICAL CO., LTD., conjugated diene compound), TINUVIN 400, TINUVIN 405, TINUVIN 460, TINUVIN 477, and TINUVIN 479 (all manufactured by BASF, triazine compounds), TINUVIN PS, TINUVIN 99-2, TINUVIN 109, TINUVIN 326, TINUVIN 328, TINUVIN 384-2, TINUVIN 900, TINUVIN 928, TINUVIN 171, and TINUVIN 1130 (all manufactured by BASF, benzotriazole compounds), ADK STAB LA-31RG (manufactured by ADEKA Corporation, benzotriazole compounds), Uvinul A, Uvinul 3049, and Uvinul 3050 (the above are manufactured by BASF, benzophenone compounds), Sumisorb 130 (manufactured by Sumika Chemtex Company, Limited, benzophenone compounds), etc. In addition, as benzotriazole compounds, MYUA series manufactured by MIYOSHI OIL & FATCO., LTD. can be cited (Chemical Industry Daily, February 1, 2016). In addition, the ultraviolet absorber can also use the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967.
[0388] 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 ultraviolet absorber may be used, or two or more ultraviolet absorbers may be used. When two or more ultraviolet absorbers are used, the total amount is preferably within the above range.
[0389] <<Polymerization inhibitor>>
[0390] The coloring composition of the present invention may 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-tert-butylphenol), and N-nitrosophenylhydroxylamine salts (ammonium salts, cerium salts, etc.). Among them, p-methoxyphenol is preferred. The content of the polymerization inhibitor is preferably 0.0001 to 5% by mass in the total solid content of the coloring composition. The polymerization inhibitor may be only one or more than two. In the case of more than two, the total amount is preferably within the above range.
[0391] <<Silane coupling agent>>
[0392] The coloring composition of the present invention can contain a silane coupling agent. In the present invention, a silane coupling agent refers to a silane compound having a hydrolyzable group and a functional group other than the hydrolyzable group. In addition, a hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can produce a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. As a hydrolyzable group, for example, a halogen atom, an alkoxy group, an acyloxy group, etc., preferably an alkoxy group. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. In addition, as a functional group other than a hydrolyzable group, for example, a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetane group, an amino group, a urea group, a thioether group, an isocyanate group, a phenyl group, etc., preferably an amino group, a (meth) acryloyl group and an epoxy group. Specific examples of the silane coupling agent include N-β-aminoethyl-γ-aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name KBM-602), N-β-aminoethyl-γ-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name KBM-603), N-β-aminoethyl-γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name KBE-602), γ-aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name KBM-903), γ-aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name KBE-903), 3-methacryloxypropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name KBE-903), and 3-methacryloxypropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name KBE-903). Co., Ltd., product name KBM-502), 3-methacryloxypropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd., product name KBM-503), etc. In addition, specific examples of silane coupling agents include compounds described in paragraphs 0018 to 0036 of Japanese Patent Publication No. 2009-288703 and compounds described in paragraphs 0056 to 0066 of Japanese Patent Publication No. 2009-242604, and these contents are incorporated into this specification. 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, and 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, the total amount is preferably within the above range.
[0393] <<Surfactant>>
[0394] The coloring composition of the present invention may contain a surfactant. As the surfactant, various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, silicone surfactants, etc. can be used. As for the surfactant, the surfactants described in paragraphs 0238 to 0245 of International Publication No. 2015 / 166779 can be cited, and the contents are incorporated into this specification.
[0395] The surfactant is preferably a fluorine-based surfactant. By including a fluorine-based surfactant in the coloring composition, the liquid properties (especially fluidity) can be further improved, and the liquid saving property can be further improved. In addition, a film with less uneven thickness can be formed.
[0396] The fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. Fluorine-based surfactants having a fluorine content within this range are effective from the perspectives of thickness uniformity and liquid saving of the coating film, and also have good solubility in the coloring composition.
[0397] As fluorine-based surfactants, there can be mentioned surfactants described in paragraphs 0060 to 0064 of JP-A-2014-041318 (corresponding paragraphs 0060 to 0064 of International Publication No. 2014 / 017669), surfactants described in paragraphs 0117 to 0132 of JP-A-2011-132503, and surfactants described in JP-A-2020-008634, and these contents are incorporated into this specification. Examples of commercially available fluorine-based surfactants include MEGAFACE 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.), etc.
[0398] In addition, the fluorine-based surfactant can also preferably use an acrylic compound, which has a molecular structure having a functional group containing a fluorine atom, and when heat is applied, the functional group containing a fluorine atom is partially cut off and the fluorine atom is volatilized. As such a fluorine-based surfactant, the MEGAFACE DS series manufactured by DIC Corporation can be cited (Chemical Industry Daily (February 22, 2016), Nikkei Industry News (February 23, 2016)), for example, MEGAFACE DS-21 can be cited.
[0399] In addition, as for the fluorine-based surfactant, it is also preferred to use a polymer of a fluorine-containing vinyl ether compound having a fluorinated alkyl or fluorinated alkylene ether group and a hydrophilic vinyl ether compound. These fluorine-based surfactants include the fluorine-based surfactants described in Japanese Patent Application Publication No. 2016-216602, which are incorporated into this specification.
[0400] The fluorine-based surfactant can also use a block polymer. The fluorine-based surfactant can also preferably use a fluorine-containing polymer compound, which contains: 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 ethyleneoxy and propyleneoxy). In addition, the fluorine-containing surfactants described in paragraphs 0016 to 0037 of Japanese Patent Application Publication No. 2010-032698 and the following compounds are also exemplified as the fluorine-based surfactants used in the present invention.
[0401] [Chemical formula 29]
[0402]
[0403] The weight average molecular weight of the above compound is preferably 3000 to 50000, for example, 14000. In the above compound, % indicating the ratio of repeating units is mol %.
[0404] In addition, the fluorine-based surfactant can also use a fluorine-containing polymer having a group containing an ethylenically unsaturated bond on the side chain. As specific examples, compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of Japanese Patent Publication No. 2010-164965, and MEGAFACE RS-101, RS-102, RS-718K, RS-72-K manufactured by DIC Corporation can be cited. In addition, the fluorine-based surfactant can also use compounds described in paragraphs 0015 to 0158 of Japanese Patent Publication No. 2015-117327.
[0405] Examples of the nonionic surfactant include glycerin, trimethylolpropane, trimethylolethane and ethoxylates and propoxylates thereof (e.g., glycerin propoxylate, glycerin ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid esters, 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 Japan Lubrizol Corporation), NCW-101, NCW-1001, NCW-1002 (manufactured by FUJIFILM Wako Pure Chemical Corporation), PIONIN D-6112, D-6112-W, D-6315 (manufactured by Takemoto Oil & Fat Co., Ltd.), OLFIN E1010, Surfynol 104, 400, 440 (manufactured by Nissin Chemical Co., Ltd.), and the like.
[0406] Examples of the silicone surfactant include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, and Toray Silicone SH8400 (all manufactured by Dow Corning Toray Co., Ltd.), TSF-4440, TSF-4300, TSF-4445, TSF-4460, and TSF-4452 (all manufactured by Momentive Performance Materials Inc.), KP-341, KF-6001, and KF-6002 (all manufactured by Shin-Etsu Chemical Co., Ltd.), BYK307, BYK323, and BYK330 (all manufactured by BYK-Chemie Corporation).
[0407] The content of the surfactant in the total solid content of the coloring composition is preferably 0.001% to 5.0% by mass, and more preferably 0.005% to 3.0% by mass. The surfactant may be only one or two or more. In the case of two or more, the total amount is preferably within the above range.
[0408] <<Antioxidants>>
[0409] The coloring composition of the present invention can contain an antioxidant. As an antioxidant, phenolic compounds, phosphite compounds, thioether compounds, etc. can be mentioned. As a phenolic compound, any phenolic compound known as a phenolic antioxidant can be used. As a preferred phenolic compound, a hindered phenolic compound can be mentioned. It is preferred that the compound has a substituent at a position adjacent to the phenolic hydroxyl group (ortho position). As the substituent, a substituted or unsubstituted alkyl group with 1 to 22 carbon atoms is preferred. In addition, the antioxidant is also preferably a compound having a phenolic group and a phosphite group in the same molecule. In addition, the antioxidant can also preferably use a phosphorus antioxidant. In addition, the antioxidant can also use the compounds described in the Korean Patent Publication No. 10-2019-0059371. The content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, and more preferably ().3 to 15% by mass. The antioxidant can be used only one kind, or two or more kinds can be used. When two or more kinds are used, the total amount is preferably within the above range.
[0410] <<Other ingredients>>
[0411] As needed, the coloring composition of the present invention may also contain a sensitizer, a curing accelerator, a filler, a thermosetting accelerator, a plasticizer and other auxiliary agents (for example, conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling accelerators, fragrances, surface tension regulators, chain transfer agents, etc.). The properties such as the physical properties of the film can be adjusted by appropriately containing these ingredients. Regarding these ingredients, for example, the records after paragraph 0183 of Japanese Patent Application Publication No. 2012-003225 (paragraph 0237 of the corresponding U.S. Patent Application Publication No. 2013 / 0034812), the records of paragraphs 0101 to 0104, 0107 to 0109 of Japanese Patent Application Publication No. 2008-250074, etc., can be referred to, and these contents are incorporated into this specification. In addition, as needed, the coloring composition of the present invention may also contain a potential antioxidant. As a potential antioxidant, a compound in which the site acting as an antioxidant is protected by a protecting group can be cited, and the protecting group is heated at 100 to 250 ° C or heated at 80 to 200 ° C in the presence of an acid / base catalyst and is separated and acts as an antioxidant. As a potential antioxidant, the compounds described in International Publication No. 2014 / 021023, International Publication No. 2017 / 030005, and Japanese Patent Publication No. 2017-008219 can be cited. As a commercially available product of a potential antioxidant, ADEKAARKLSGPA-5001 (manufactured by ADEKA CORPORATION) can be cited.
[0412] In order to adjust the refractive index of the obtained film, the coloring composition of the present invention may contain a metal oxide. Examples of the metal oxide include TiO2, ZrO2, Al2O3, SiO2, etc. The primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and further preferably 5 to 50 nm. The metal oxide may have a core-shell structure. In this case, the core may be hollow.
[0413] The coloring composition of the present invention may contain a light fastness improving agent. Examples of the light fastness improving agent include compounds described in paragraphs 0036 to 0037 of Japanese Patent Application Publication No. 2017-198787, compounds described in paragraphs 0029 to 0034 of Japanese Patent Application Publication No. 2017-146350, compounds described in paragraphs 0036 to 0037 and 0049 to 0052 of Japanese Patent Application Publication No. 2017-129774, and compounds described in paragraphs 0036 to 0037 and 0049 to 0052 of Japanese Patent Application Publication No. 201 The compounds described in paragraphs 0031 to 0034 and 0058 to 0059 of 7-129674, the compounds described in paragraphs 0036 to 0037 and 0051 to 0054 of JP-A-2017-122803, the compounds described in paragraphs 0025 to 0039 of International Publication No. 2017 / 164127, and JP-A-2017-186546 The compounds described in paragraphs 0034 to 0047 of JP-A-2015-025116, the compounds described in paragraphs 0019 to 0041 of JP-A-2012-145604, the compounds described in paragraphs 0101 to 0125 of JP-A-2012-103475, the compounds described in paragraphs 0018 to 0021 of JP-A-2011- The compounds described in paragraphs 0015 to 0018 of Japanese Patent Application No. 257591, the compounds described in paragraphs 0017 to 0021 of Japanese Patent Application No. 2011-191483, the compounds described in paragraphs 0108 to 0116 of Japanese Patent Application No. 2011-145668, the compounds described in paragraphs 0103 to 0153 of Japanese Patent Application No. 2011-253174, and the like.
[0414] The coloring composition of the present invention also preferably contains substantially no terephthalate. Here, “substantially contains no” means that the content of terephthalate in the total amount of the coloring composition is 1000 ppb by mass or less, more preferably 100 ppb by mass or less, and particularly preferably zero.
[0415] Sometimes, it is preferred to reduce the amount of perfluoroalkyl sulfonic acid and perfluoroalkyl carboxylic acid for reasons such as environmental protection. The content of perfluoroalkyl sulfonic acid and perfluoroalkyl carboxylic acid (especially perfluoroalkyl sulfonic acid and perfluoroalkyl carboxylic acid having 6 to 8 carbon atoms in the alkyl group) in the solid content of the resin composition is preferably 0.01 to 1000 mass ppb, more preferably 0.05 to 500 mass ppb, and further preferably 0.1 to 300 mass ppb. In addition, instead of compounds having different carbon atoms, it is also preferred to set the mode in which these compounds are substantially not contained.
[0416] 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 0.1 to 1.0% by mass. The water content can be measured by the Karl Fischer method.
[0417] The coloring composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface shape (flatness, etc.) and adjusting the film thickness. The viscosity value can be appropriately selected as needed, but for example, it is preferably 0.3mPa·s to 50mPa·s at 25°C, and more preferably 0.5mPa·s to 20mPa·s. As a method for measuring the viscosity, for example, a cone-plate viscometer can be used to measure the viscosity at a temperature adjusted to 25°C.
[0418] The storage container of the coloring composition of the present invention is not particularly limited, and a known storage container can be used. In addition, as the storage container, for the purpose of suppressing the mixing of impurities into the raw materials or the composition, it is also preferable to use a multilayer bottle having an inner wall of the container composed of 6 types of 6 layers of resin or a bottle having a 7-layer structure of 6 types of resin. As such a container, for example, the container described in Japanese Patent Application Laid-Open No. 2015-123351 can be cited.
[0419] <Method for preparing coloring composition>
[0420] The coloring composition of the present invention can be prepared by mixing the above-mentioned components. When preparing the coloring composition, all the components can be dissolved and / or dispersed in a solvent at the same time to prepare the coloring composition, or each component can be appropriately prepared as two or more solutions or dispersions and mixed when used (when applied) to prepare the coloring composition as needed.
[0421] In addition, when preparing the coloring composition, it is preferred to include a process for dispersing the pigment. As the mechanical force used for dispersing the pigment in the process for dispersing the pigment, compression, pressing, impact, shearing, cavitation, etc. can be cited. As specific examples of these processes, bead milling, sand milling, roller milling, ball milling, paint stirring, micro jet, high-speed impeller, sand mixing, jet stream mixing, high-pressure wet micronization, ultrasonic dispersion, etc. can be cited. In addition, in the pulverization of the pigment under sand milling (bead milling), it is preferably processed under the following conditions: by using microbeads with a small diameter and increasing the filling rate of the microbeads, the pulverization efficiency is improved. In addition, it is preferred to remove coarse particles by filtering, centrifuging, etc. after the pulverization process. In addition, regarding the process and disperser for dispersing the pigment, the process and disperser described in paragraph 0022 of "Dispersion Technology Collection, JOHOKIKO CO., LTD., July 15, 2005" or "Dispersion Technology and Industrial Practical Application Comprehensive Data Collection Centering on Suspension (Solid / Liquid Dispersion System), Business Development Center Publishing Department, October 10, 1978", and Japanese Patent Publication No. 2015-157893 can be preferably used. In addition, in the process for dispersing the pigment, the particles can be finely processed by a salt milling process. The raw materials, equipment, processing conditions, etc. used in the salt milling process can be referred to, for example, the records in Japanese Patent Publication No. 2015-194521 and Japanese Patent Publication No. 2012-046629.
[0422] When preparing the coloring composition, for the purpose of removing foreign matter or reducing defects, it is preferred to filter the coloring composition using a filter. As a filter, as long as it is a filter used for filtering purposes, it can be used without particular restrictions. For example, a filter using materials such as polyolefin resins (including high-density, ultra-high molecular weight polyolefin resins) such as polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVDF), polyamide resins such as nylon (such as nylon-6, nylon-6,6), polyethylene, polypropylene (PP), etc. can be cited. Among these materials, polypropylene (including high-density polypropylene) and nylon are preferred.
[0423] The pore size of the filter is preferably 0.01 to 7.0 μm, more preferably 0.01 to 3.0 μm, and further preferably 0.05 to 0.5 μm. As long as the pore size of the filter is within the above range, fine foreign matter can be removed more reliably. Regarding the pore size value of the filter, the nominal value of the filter manufacturer can be referred to. Regarding the filter, various filters provided by NIHON PALL Corporation (DFA4201NIEY, DFA4201NAEY, DFA4201J006P, etc.), Advantec Toyo Kaisha, Ltd., NihonEntegris KK (Formerly Nippon Mykrolis Corporation) and KITZ MICROFILTERCorporation can be used.
[0424] Furthermore, as a filter, it is also preferred to use a fibrous filter material. As fibrous filter materials, for example, polypropylene fibers, nylon fibers, glass fibers, etc. can be cited. As commercially available products, the SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by ROKI TECHNO CO., LTD. can be cited. When using a filter, different filters (for example, a first filter and a second filter, etc.) can be combined. At this time, filtration with each filter can be performed only once or more than twice. Furthermore, filters of different pore sizes can be combined within the above range. Furthermore, it can also be performed as follows: when filtering with the first filter, only the dispersion is filtered, and after mixing other components, it is filtered with the second filter. Furthermore, the filter can be appropriately selected according to the hydrophilicity of the coloring composition.
[0425] <Film>
[0426] The film of the present invention is a film obtained from the above-mentioned colored composition of the present invention. The film of the present invention can also be used for optical filters such as color filters and infrared transmission filters.
[0427] 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 further 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 further preferably 0.3 μm or more.
[0428] 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. In addition, the film of the present invention can be preferably used as a colored pixel of a color filter. As colored pixels, red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, etc. can be cited, preferably red pixels, green pixels and yellow pixels, more preferably red pixels or green pixels, and further preferably green pixels.
[0429] Furthermore, the wavelength at which the transmittance of the film of the present invention becomes 50% preferably exists in the wavelength range of 470 to 520 nm, more preferably exists in the wavelength range of 475 to 520 nm, and further preferably exists in the wavelength range of 480 to 520 nm. Among them, the wavelength at which the transmittance becomes 50% preferably exists in the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm, respectively. In this mode, the wavelength on the short wavelength side at which the 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. Furthermore, the wavelength on the long wavelength side at which the 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. Films having these spectral characteristics can be preferably used as green pixels.
[0430] 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), for example.
[0431] (1): The maximum value of the light transmittance in the thickness direction of the film within 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 within the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more). The film having these spectral characteristics can shield light within the wavelength range of 400 to 640 nm and transmit light exceeding a wavelength of 700 nm.
[0432] (2): A film having a maximum light transmittance in the thickness direction of the film of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 750 nm and a minimum light transmittance in the thickness direction of the film of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 900 to 1300 nm. A film having these spectral characteristics can shield light in the wavelength range of 400 to 750 nm and transmit light exceeding a wavelength of 850 nm.
[0433] (3): A film having a maximum light transmittance in the thickness direction of the film of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 830 nm and a minimum light transmittance in the thickness direction of the film of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1000 to 1300 nm. A film having these spectral characteristics can shield light in the wavelength range of 400 to 830 nm and transmit light exceeding a wavelength of 940 nm.
[0434] (4): A film having a maximum light transmittance in the thickness direction of the film of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 950 nm and a minimum light transmittance in the thickness direction of the film of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm. A film having these spectral characteristics can shield light in the wavelength range of 400 to 950 nm and transmit light exceeding a wavelength of 1040 nm.
[0435] <Method for producing film>
[0436] Next, the method for producing the film of the present invention is described. The film of the present invention can be produced by applying the coloring composition of the present invention. The method for producing the film preferably further includes a step of forming a pattern (pixel). As a method for forming a pattern (pixel), photolithography and dry etching can be cited, preferably photolithography.
[0437] The pattern formation by photolithography preferably includes the following steps: 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). A step of baking the colored composition layer (pre-baking step) and a step of baking the developed pattern (pixel) (post-baking step) may also be provided as needed.
[0438] In the process of forming a colored composition layer, a colored composition layer is formed on a support using a colored composition. As a support, there is no particular limitation and it can be appropriately selected according to the purpose. For example, a glass substrate, a silicon substrate, etc. can be cited, preferably a silicon substrate. In addition, a charge coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. can also be formed on the silicon substrate. In addition, a black matrix is sometimes formed on the silicon substrate to isolate each pixel. In addition, in order to improve the adhesion with the upper layer, prevent the diffusion of substances, or flatten the surface of the substrate, a base layer can be provided on the silicon substrate. A base layer can also be formed using a composition in which a colorant is removed from the colored composition described in this specification or 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. And, 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 wettability of the resin composition is good. The adjustment of the surface contact angle of the base layer can be carried out, for example, by methods such as the addition of a surfactant.
[0439] As a coating method of the coloring composition, a known method can be used. For example, there can be mentioned a drop coating method (drop casting); a slit coating method; a spray method; a roll coating method; a spin coating method (spin coating); a cast coating method; a slit spin coating method; a pre-wetting method (for example, the method described in Japanese Patent Application Publication No. 2009-145395); various printing methods such as ejection printing such as inkjet (for example, on-demand method, piezoelectric method, thermal method), nozzle jetting, flexographic printing, screen printing, gravure printing, reverse overprint printing, metal mask printing method, etc.; a transfer method using a mold, etc.; a nanoimprint method, etc. The application method based on inkjet is not particularly limited, and for example, the method described in "Inkjet that can be promoted and used - Infinite possibilities appearing in patents -, published in February 2005, Sumitbe Techon Research Co., Ltd." (especially pages 115 to 133) or Japanese Patent Application Publication No. 2003-262716, Japanese Patent Application Publication No. 2003-185831, Japanese Patent Application Publication No. 2003-261827, Japanese Patent Application Publication No. 2012-126830, Japanese Patent Application Publication No. 2006-169325, etc. can be cited. In addition, regarding the coating method of the coloring composition, reference can be made to the descriptions of International Publication No. 2017 / 030174 and International Publication No. 2017 / 018419, and these contents are incorporated into this specification.
[0440] The colored composition layer formed on the support can be dried (prebaked). When the film is manufactured by a low-temperature process, prebaking may not be performed. When prebaking is performed, the prebaking temperature is preferably below 150°C, more preferably below 120°C, and further preferably below 110°C. The lower limit can be set to above 50°C, for example, and can also be set to above 80°C. The prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and further preferably 80 to 220 seconds. Prebaking can be performed using a hot plate, an oven, or the like.
[0441] Next, the colored composition layer is exposed to a pattern (exposure step). For example, a stepper, a scanner, or the like is used to expose the colored composition layer through a mask having a predetermined mask pattern, thereby exposing the colored composition layer to a pattern. Thus, the exposed portion can be cured.
[0442] As radiation (light) that can be used for exposure, g-rays, i-rays, etc. can be cited. In addition, light with a wavelength of 300nm or less (preferably light with a wavelength of 180 to 300nm) can also be used. As light with a wavelength of 300nm or less, KrF rays (wavelength 248nm), ArF rays (wavelength 193nm), etc. can be cited, preferably KrF rays (wavelength 248nm). In addition, a light source with a long wavelength of 300nm or more can also be used.
[0443] Furthermore, during exposure, the light may be continuously irradiated or pulsed (pulse exposure). In addition, pulse exposure refers to an exposure method in which light is irradiated and stopped repeatedly in a short period of time (e.g., less than milliseconds) to perform exposure.
[0444] The irradiation amount (exposure amount) is preferably 0.03 to 2.5 J / cm 2 , more preferably 0.05 to 1.0 J / cm 2 The oxygen concentration during exposure can be appropriately selected. In addition to exposure under the atmosphere, exposure can also be performed in a low oxygen atmosphere with an oxygen concentration of 19% by volume or less (e.g., 15% by volume, 5% by volume, or substantially oxygen-free), or in a high oxygen atmosphere with an oxygen concentration exceeding 21% by volume (e.g., 22% by volume, 30% by volume, or 50% by volume). In addition, the exposure illuminance can be appropriately set, usually from 1000 W / m 2 ~100000W / m 2 (For example, 5000W / m 2 , 15000W / m 2 or 35000W / m 2 The oxygen concentration and exposure illuminance can be appropriately combined, for example, the oxygen concentration can be set to 10% by volume and the illuminance can be set to 10000 W / m 2, oxygen concentration 35 volume % and illumination 20000W / m 2 wait.
[0445] Next, the unexposed portion of the colored composition layer is removed by development 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 process is dissolved in the developer, and only the photocured portion remains. The temperature of the developer is preferably 20 to 30°C, for example. The development time is preferably 20 to 180 seconds. In addition, in order to improve the removability of the residue, the process of shaking off the developer every 60 seconds and then supplying a new developer can be repeated multiple times.
[0446] The developer can include organic solvents, alkaline developers, etc., and an alkaline developer can be preferably used. As an alkaline developer, an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferred. As an alkaline agent, for example, organic alkaline compounds such as ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, 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, or inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium silicate, and sodium metasilicate can be mentioned. From the perspective of environment and safety, the alkaline agent is preferably a compound with a large molecular weight. The concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, and more preferably 0.01 to 1% by mass. Furthermore, the developer may further contain a surfactant. From the viewpoint of convenience of transportation and storage, the developer may also be prepared as a concentrated solution first, and then diluted to the desired concentration when used. The dilution ratio is not particularly limited, for example, it can be set in the range of 1.5 to 100 times. Furthermore, it is also preferred to wash (rinse) with pure water after development. Furthermore, it is preferred to rotate the support on which the developed colored composition layer is formed while supplying a rinsing liquid to the developed colored composition layer for rinsing. Furthermore, it is also preferred to move the nozzle that discharges the rinsing liquid from the center of the support to the peripheral portion of the support. At this time, when the nozzle moves from the center of the support to the peripheral portion, it can be moved while gradually reducing the moving speed of the nozzle. By rinsing as above, the in-plane deviation of the rinsing can be suppressed. Furthermore, the same effect can be obtained by gradually reducing the rotation speed of the support while moving the nozzle from the center of the support to the peripheral portion.
[0447] It is preferred that additional exposure treatment or heating treatment (post-baking) is performed after development and drying. Additional exposure treatment or post-baking is a curing treatment after development for completely curing it. The heating temperature in the post-baking is preferably 100 to 240°C, more preferably 200 to 240°C. In a manner that meets the above conditions, a heating plate, a convection oven (hot air circulation dryer), a high-frequency heater or other heating mechanism can be used to post-bake the film after development in a continuous or intermittent manner so that the film meets the above conditions. In the case of additional exposure treatment, the light used for exposure is preferably light with a wavelength of less than 400nm. In addition, the additional exposure treatment can be performed by the method described in Korean Patent Gazette No. 10-2017-0122130.
[0448] The pattern formation based on the dry etching method preferably includes the following steps: forming a colored composition layer on a support using the colored composition of the present invention, and curing the colored composition layer as a whole to form a cured layer; forming a photoresist layer on the cured layer; exposing the photoresist layer to a pattern, and then developing it to form a resist pattern; and using the resist pattern as a mask, using an etching gas to dry-etch the cured layer. When forming the photoresist layer, it is preferred to further perform a pre-baking treatment. In particular, as a process for forming the photoresist layer, it is preferred to perform a heating treatment after exposure and a heating treatment after development (post-baking treatment). Regarding the pattern formation using the dry etching method, reference can be made to the description of paragraphs 0010 to 0067 of Japanese Patent Publication No. 2013-064993, and the content is incorporated into this specification.
[0449] <Filter>
[0450] The optical filter of the present invention has the above-mentioned film of the present invention. As the type of the optical filter, a color filter and an infrared transmission filter can be mentioned, and a color filter is preferred. As the color filter, it is preferred to have the film of the present invention as a colored pixel of the color filter.
[0451] In the optical filter, the film thickness of the film of the present invention can be appropriately adjusted according to the purpose. The film thickness is preferably 5 μm or less, more preferably 1 μm or less, and further preferably 0.6 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 further preferably 0.3 μm or more.
[0452] The width of the pixel included in the filter is preferably 0.4 to 10.0 μm. The lower limit is preferably 0.4 μm or more, more preferably 0.5 μm or more, and further preferably 0.6 μm or more. The upper limit is preferably 5.0 μm or less, more preferably 2.0 μm or less, further preferably 1.0 μm or less, and further preferably 0.8 μm or less. In addition, the Young's modulus of the pixel is preferably 0.5 to 20 GPa, and more preferably 2.5 to 15 GPa.
[0453] Each pixel included in the filter preferably has high flatness. Specifically, the surface roughness Ra of the pixel is preferably less than 100 nm, more preferably less than 40 nm, and further preferably less than 15 nm. There is no regulation on the lower limit, but for example, it is preferably greater than 0.1 nm. Regarding the surface roughness of the pixel, for example, it can be measured using AFM (atomic force microscope) Dimension3100 manufactured by Veeco. In addition, the water contact angle on the pixel can be appropriately set to a preferred value, usually in the range of 50 to 110°. The contact angle can be measured, for example, using a contact angle meter CV-DT·A type (manufactured by Kyowa Interface Science Co., LTD.). In addition, the volume resistance value of the pixel is preferably high. Specifically, the volume resistance value of the pixel is preferably 10 9 Ω·cm or more, more preferably 10 11 Ω·cm or more. The upper limit is not specified, for example, preferably 10 14 The volume resistance value of the pixel can be measured using an ultra high resistance meter 5410 (manufactured by Advantest Corporation).
[0454] In the optical filter, a protective layer may also be provided on the surface of the film of the present invention. By providing a protective layer, various functions such as oxidation resistance, low reflection, hydrophilicity / hydrophobicity, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted. As the thickness of the protective layer, preferably 0.01 to 10 μm, more preferably 0.1 to 5 μm. As a method for forming the protective layer, a method of forming by coating a resin composition dissolved in an organic solvent, a chemical vapor deposition method, a method of attaching a formed resin using an adhesive material, etc. can be cited. As the components constituting the protective layer, (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, polyamide-imide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, polyurethane 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., can be cited, and two or more of these components can also be contained. For example, in the case of a protective layer for the purpose of anti-oxidation, the protective layer preferably contains polyol resin, SiO2 and Si2N4. In addition, in the case of a protective layer for the purpose of low reflection, the protective layer preferably contains (meth) acrylic resin and fluororesin.
[0455] When the protective layer is formed by applying the resin composition, as the coating method of the resin composition, known methods such as spin coating, casting, screen printing, inkjet method can be used. The organic solvent contained in the resin composition can use a known organic solvent (for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.). When the protective layer is formed by chemical vapor deposition, as chemical vapor deposition, known chemical vapor deposition (thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition) can be used.
[0456] The protective layer may also contain organic / inorganic particles, absorbents of light of a specific wavelength (e.g., ultraviolet rays, near infrared rays, etc.), refractive index modifiers, antioxidants, adhesives, surfactants and other additives as needed. As examples of organic / inorganic particles, for example, polymer particles (e.g., silicone resin particles, polystyrene particles, melamine resin particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride, magnesium fluoride, hollow silica, silicon dioxide, calcium carbonate, barium sulfate, etc. can be cited. The absorbent of light of a specific wavelength can use a known absorbent. The content of these additives can be appropriately adjusted, but preferably 0.1 to 70% by mass relative to the total mass of the protective layer, and more preferably 1 to 60% by mass. In addition, as a protective layer, the protective layer described in paragraphs 0073 to 0092 of Japanese Patent Publication No. 2017-151176 can also be used.
[0457] The optical filter may have a structure in which pixels are embedded in spaces partitioned by partition walls, for example, in a grid pattern.
[0458] <Solid-state imaging device>
[0459] The solid-state imaging device of the present invention has the above-mentioned film of the present invention. The structure of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device, and examples thereof include the following structures.
[0460] The structure of the imaging element is as follows: a plurality of photodiodes and transfer electrodes of polysilicon or the like including a light receiving area constituting a solid-state imaging element (CCD (charge coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) are provided on a substrate, a light shielding film having only the light receiving portion of the photodiode open is provided on the photodiode and the transfer electrode, a device protection film of silicon nitride or the like formed in a manner covering the entire surface of the light shielding film and the light receiving portion of the photodiode is provided on the light shielding film, and a color filter is provided on the device protection film. Furthermore, it may be a structure having a focusing mechanism (e.g., a microlens, etc., the same below) on the device protection film and below the color filter (on the side close to the substrate) or a structure having a focusing mechanism on the color filter. Furthermore, the color filter may also have a structure in which each color pixel is embedded in a space separated by a partition wall, for example, in a grid shape. Preferably, the refractive index of the partition wall at this time is lower than the refractive index of each color pixel. As an example of an imaging device having such a structure, the devices described in Japanese Patent Publication No. 2012-227478, Japanese Patent Publication No. 2014-179577, and International Publication No. 2018 / 043654 can be cited. In addition, as shown in Japanese Patent Publication No. 2019-211559, an ultraviolet absorption layer can also be provided in the structure of the solid-state imaging element to improve light resistance. In addition to being able to be used as a digital camera or an electronic device with an imaging function (mobile phone, etc.), the imaging device having the solid-state imaging element of the present invention can also be used as a vehicle-mounted camera or a surveillance camera.
[0461] <Image display device>
[0462] The image display device of the present invention has the above-mentioned film of the present invention. As the image display device, a liquid crystal display device or an organic electroluminescent display device can be cited. The definition of the image display device or the details of each image display device are recorded in, for example, "Electronic Display Device (written by Akio Sasaki, Kogyo Chosakai Publishing Co., Ltd., published in 1990)", "Display Device (written by Junzhang Ibuki, Sangyo Tosho Publishing Co., Ltd., published in 1989)" and the like. In addition, regarding the liquid crystal display device, it is recorded in, for example, "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Publishing Co., Ltd., published in 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied, for example, it can be applied to various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology".
[0463] Example
[0464] Below, give embodiment and the present invention is further specifically described.The material, usage amount, ratio, processing content, processing sequence etc. shown in the following embodiment can be appropriately changed as long as it does not depart from the purpose of the present invention.Therefore, the scope of the present invention is not limited to the specific example shown below.
[0465] <Synthesis Example of Compound S>
[0466] (Synthesis Example 1) Synthesis of Compound (S-1)
[0467] [Chemical formula 30]
[0468]
[0469] 26.5 parts by mass of compound (a-1), 17.2 parts by mass of compound (b-1), 6.6 parts by mass of acetic acid and 910 parts by mass of N-ethylpyrrolidone were mixed, and stirred while heating at an external temperature of 70°C for 3 hours under a nitrogen stream. 2.0 parts by mass of copper acetate monohydrate were added, and the mixture was further heated for 3 hours. Next, 2500 parts by mass of ethyl acetate were added, and the mixture was stirred while heating at 70°C for 1 hour, and then the liquid temperature was cooled to 5°C. The obtained solid was screened, washed with 910 parts by mass of methanol, 910 parts by mass of a 5% aqueous solution of sodium bicarbonate and 910 parts by mass of water, and dried with air at 50°C, thereby obtaining 40.1 parts by mass of compound (S-1). The value of (M+H)(posi) in the mass spectrum of the synthesized compound (S-1) was 481.
[0470] (Synthesis Examples 2 to 34) Synthesis of Compounds (S-2) to (S-34)
[0471] Compounds (S-2) to (S-34) were obtained by performing the same operation as in Synthesis Example 1 except that the compound (a-1), compound (b-1) and metal source were changed to the types and charged amounts described in Table 1.
[0472] (Synthesis Example 35) Synthesis of Compound (S-35)
[0473] Compound (S-35) was obtained by performing the same operations as in Synthesis Example 1, except that compound (a-1), compound (b-1), acetic acid and methanol were changed to the types and charging amounts described in Table 1 and 14 parts by mass of piperidine were added when adding the metal source.
[0474] (Synthesis Example 36) Synthesis of Compound (S-36)
[0475] Compound (S-36) was obtained by carrying out the same operation as in Synthesis Example 1 except that copper acetate monohydrate was not added.
[0476] [Table 3]
[0477]
[0478] Compounds (a-1) to (a-25) and compounds (b-1) to (b-5) are compounds having the structures shown below, respectively. In addition, the metal source (m-1) is copper acetate monohydrate, the metal source (m-2) is zinc acetate, the metal source (m-3) is iron acetate, (m-4) is tetraisopropoxytitanium, and the metal source (m-5) is tin (IV) chloride.
[0479] [Table 4]
[0480]
[0481] [Table 5]
[0482]
[0483] [Table 6]
[0484]
[0485] (Synthesis Example 37) Synthesis of Compound (S-37)
[0486] At room temperature, a solution consisting of 14.5 parts by mass of 8-hydroxyquinoline, 21.0 parts by mass of piperidine and 200 parts by mass of ethanol was stirred, and the mixture was slowly added dropwise to a solution consisting of 24.1 parts by mass of aluminum chloride hexahydrate and 200 parts by mass of ethanol, and stirred for 1 hour. Next, 47.3 parts by mass of compound (S-36) were added, and then 21.0 parts by mass of piperidine and 200 parts by mass of ethanol were added, and stirred at room temperature for 48 hours. The precipitated solid was filtered, washed with ethanol and water, and dried by air supply at 50°C, thereby obtaining 59.2 parts by mass of compound (S-37). The value of (M+H)(posi) of the synthesized compound (S-37) was 625.
[0487] (Synthesis Example 38) Synthesis of Compound (S-38)
[0488] The same operation was carried out except that the aluminum chloride hexahydrate in Synthesis Example 37 was changed to 21.4 parts by mass of magnesium acetate tetrahydrate, thereby obtaining 55.1 parts by mass of a compound (S-38).
[0489] The structural formulae and mass spectrometry results ((M+H)) of compounds (S-1) to (S-38) are shown below. In the structural formulae shown below, the nitrogen atom is coordinated to the metal atom, but depending on the state of the metal atom, the nitrogen atom may not be coordinated to the metal atom.
[0490] [Table 7]
[0491]
[0492] [Table 8]
[0493]
[0494] [Table 9]
[0495]
[0496] <Preparation of dispersion>
[0497] The mixed solution of the raw materials listed in the following table was mixed and dispersed for 3 hours using a bead mill (zirconia microbeads with a diameter of 0.1 mm). Then, a high-pressure disperser NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) with a decompression mechanism was used at a pressure of 2000 kg / cm 3 The dispersion treatment was carried out under the conditions of 500 g / min and a flow rate of 500 g / min. The dispersion treatment was repeated 10 times to obtain a dispersion liquid. The numerical values representing the blending amount recorded in the following table are parts by mass. In addition, the numerical values of the added amount of the dispersant are numerical values converted to solid content.
[0498] [Table 10]
[0499]
[0500] [Table 11]
[0501]
[0502] The details of the raw materials described by abbreviations in the above table are as follows.
[0503] (pigment)
[0504] PY117: CI Pigment Yellow 117 (azomethine copper complex, yellow pigment)
[0505] PY129: CI Pigment Yellow 129 (azomethine copper complex, yellow pigment)
[0506] PY138: CI Pigment Yellow 138 (quinophthalone compound, yellow pigment)
[0507] PY139: CI Pigment Yellow 139 (isoindoline compound, yellow pigment)
[0508] PY150: CI Pigment Yellow 150 (azo nickel complex, yellow pigment)
[0509] PY185: CI Pigment Yellow 185 (isoindoline compound, yellow pigment)
[0510] Y-1: Compound of the following structure (quinophthalone compound, yellow pigment)
[0511] Y-2: Compound of the following structure (quinophthalone compound, yellow pigment)
[0512] Y-3: Compound of the following structure (azomethine zinc complex, yellow pigment)
[0513] [Chemical formula 31]
[0514]
[0515] PG7: CI Pigment Green 7 (copper phthalocyanine complex, green pigment)
[0516] PG36: CI Pigment Green 36 (copper phthalocyanine complex, green pigment)
[0517] PG58: CI Pigment Green 58 (zinc phthalocyanine complex, green pigment)
[0518] PG59: CI Pigment Green 59 (zinc phthalocyanine complex, green pigment)
[0519] PG62: CI Pigment Green 62 (aluminum phthalocyanine complex, green pigment)
[0520] PG63: CI Pigment Green 63 (aluminum phthalocyanine complex, green pigment)
[0521] PR254: CI Pigment Red 254 (diketopyrrolopyrrole compound, red pigment)
[0522] PR264: CI Pigment Red 264 (diketopyrrolopyrrole compound, red pigment)
[0523] PR272: CI Pigment Red 272 (diketopyrrolopyrrole compound, red pigment)
[0524] PR122: CI Pigment Red 122 (quinacridone compound, red pigment)
[0525] PV23: CI Pigment Violet 23 (dioxane compound, purple pigment)
[0526] PB15:6: CI Pigment Blue 15:6 (copper phthalocyanine complex, blue pigment)
[0527] PB2: Carbon black (black pigment)
[0528] (Dispersant)
[0529] B-1: Resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 24,000, acid value: 47 mgKOH / g)
[0530] [Chemical formula 32]
[0531]
[0532] B-2: Resin having the following structure (the numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 16000, acid value: 67 mgKOH / g)
[0533] [Chemical formula 33]
[0534]
[0535] B-3: Resin having the following structure (the numerical value attached to the main chain is the mass ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 13000, acid value: 65 mgKOH / g)
[0536] [Chemical formula 34]
[0537]
[0538] B-4: Resin B-4 synthesized by the following method
[0539] 50 parts by mass of methyl methacrylate, 30 parts by mass of n-butyl methacrylate, 20 parts by mass of tert-butyl methacrylate, and 45.4 parts by mass of PGMEA (propylene glycol monomethyl ether acetate) were placed in a reaction vessel, and the atmosphere was replaced with nitrogen. The reaction vessel was heated to 70°C, 6 parts by mass of 3-mercapto-1,2-propanediol was added, and 0.12 parts by mass of AIBN (azobisisobutyronitrile) was added, and the reaction was allowed to proceed for 12 hours. The solid content was measured to confirm that the reaction proceeded by 95%. Next, 9.7 parts by mass of pyromellitic anhydride, 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 allowed to proceed for 7 hours at 120°C. The acid value was measured to confirm that more than 98% of the anhydride was half-esterified and the reaction was terminated. PGMEA was added to adjust the nonvolatile content (solid content) to 30% by mass, to obtain a resin solution of a resin B-4 having the following structure and an acid value of 43 mgKOH / g and a weight average molecular weight of 9,000.
[0540] [Chemical formula 35]
[0541]
[0542] B-5: DISPERBYK-2001 (resin having a basic group, amine value 29 mgKOH / g, manufactured by BYK JapanKK)
[0543] B-6: Resin with the following structure (block copolymer. The values indicated on the main chain are mass ratios. Amine value: 71 mgKOH / g, weight average molecular weight: 9900)
[0544] [Chemical formula 36]
[0545]
[0546] B-7: Resin with the following structure (weight average molecular weight 13000, k / (l1+l2) / (m1+m2) / n=10 / 50 / 5 / 35 (molar ratio)
[0547] [Chemical formula 37]
[0548]
[0549] b1: Resin with the following structure (the numerical values attached to the main chain are molar ratios. Weight average molecular weight: 30,000)
[0550] [Chemical formula 38]
[0551]
[0552] b2: Resin with the following structure (the numerical values attached to the main chain are molar ratios. Weight average molecular weight: 11000)
[0553] [Chemical formula 39]
[0554]
[0555] b3: Resin with the following structure (the numerical values attached to the main chain are molar ratios. Weight average molecular weight: 10,000)
[0556] [Chemical formula 40]
[0557]
[0558] (Specific Compound)
[0559] S-1 to S-38: the above compounds (S-1) to (S-38)
[0560] SD-1: Compound with the following structure
[0561] [Chemical formula 41]
[0562]
[0563] SD-2: Compound with the following structure
[0564] [Chemical formula 42]
[0565]
[0566] SH-1: a compound having the following structure (a compound synthesized by the synthesis method described in paragraph 0073 of JP-A-2009-035671)
[0567] [Chemical formula 43]
[0568]
[0569] (Solvent)
[0570] PGMEA: Propylene glycol monomethyl ether acetate
[0571] PGME: Propylene glycol
[0572] CHN: Cyclopentanone
[0573] The results of measuring the particle sizes of the pigments contained in the dispersions (D-1), (D-5), (D-9) and the dispersions (D-25), (D-26), (D-28) show that the average particle size of the pigments contained in the dispersions (D-1), (D-5), (D-9) is 40 to 60 nm, while the average particle size of the pigments contained in the dispersions (D-25), (D-26), (D-28) is as high as 80 to 90 nm. Therefore, it can be seen that R in formula (1) and (1a) 6 ~R 9 At least one of the groups contains a group represented by the formula (R-1), which enables the pigment to be dispersed more finely.
[0574] <Production of Coloring Composition>
[0575] The dispersion described in the following table, the polymerizable compound described in the following table, the photopolymerization initiator described in the following table, the resin described in the following table, 1 part by mass of an epoxy compound (EHPE-3150, manufactured by Daicel Corporation), 1 part by mass of an ultraviolet absorber (TINUVIN326, manufactured by BASF), 1 part by mass of a surfactant 1 shown below, and 0.1 part by mass of a polymerization inhibitor (p-methoxyphenol) were mixed to prepare a coloring composition.
[0576] Surfactant 1: 1 mass % PGMEA solution of a compound having the following structure (weight average molecular weight: 14,000; the numerical value indicating the ratio of repeating units is mol %).
[0577] [Chemical formula 44]
[0578]
[0579] [Table 12]
[0580]
[0581] [Table 13]
[0582]
[0583] The raw materials described by abbreviations in the above table are as follows.
[0584] (Dispersion liquid)
[0585] D-1 to D-69, DS-1, DS-2, DH-1: the above dispersions D-1 to D-69, DS-1, DS-2, DH-1
[0586] (Polymerizable compound)
[0587] M-1: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.)
[0588] M-2: NK ESTER A-DPH-12E (manufactured by Shin-Nakamura Chemical Co., Ltd.)
[0589] M-3: NK ESTER A-TMMT (manufactured by Shin-Nakamura Chemical Co., Ltd.)
[0590] M-4: Succinic acid modified dipentaerythritol pentaacrylate
[0591] M-5: Dipentaerythritol hexaacrylate
[0592] (Photopolymerization Initiator)
[0593] I-1 to I-11: Compounds of the following structures
[0594] [Chemical formula 45]
[0595]
[0596] <Evaluation of Development Properties>
[0597] The CT-4000L solution (manufactured by FUJIFILM Electronic Materials Co., Ltd.; transparent primer) was applied to a silicon wafer having a diameter of 8 inches (20.32 cm) so that the dry film thickness was 0.1 μm, and after drying to form a base layer, a heat treatment was performed at 220°C for 5 minutes. Using a spin coater, each coloring composition was applied to a silicon wafer having a base layer formed thereon so that the film thickness after pre-baking was 0.6 μm, and a heat treatment (pre-baking) was performed for 120 seconds using a hot plate at 100°C. Next, a mask pattern having square pixels with a side of 1.1 μm was arranged in an area of 4 mm × 3 mm on the substrate, and an i-ray stepper exposure device FPA-3000i5+ (manufactured by Canon Inc.) was used at 500 mJ / cm 2 The exposure was performed by irradiating light of a wavelength of 365 nm with an exposure amount of 100 nm. The silicon wafer with the exposed film was placed on a horizontal rotating table of a spin / spray developer (DW-30 model, manufactured by CHEMITRONICS CO., Ltd.), and a spin-immersion development was performed at 23°C for 60 seconds using an alkaline developer (CD-2060, manufactured by FUJIFILM Electronic Materials Co., Ltd.). Next, the silicon wafer after the spin-immersion development was fixed on a horizontal rotating table by a vacuum chuck, and pure water was supplied from a nozzle in a spray state from above the center of rotation while the silicon wafer was rotated at a rotation speed of 50 rpm by a rotating device to perform a rinsing treatment (23 seconds × 2 times), followed by spin drying, and then a heating treatment (post-baking) was performed at 200°C for 300 seconds using a hot plate, thereby forming a colored pattern (pixel). The silicon wafer on which the colored pattern (pixel) was formed was observed at a magnification of 30,000 times using a length-measuring SEM (scanning electron microscope) (S-7800H, manufactured by Hitachi, Ltd.) The developability was evaluated according to the following criteria.
[0598] (Evaluation Criteria)
[0599] A: No residue was observed in the unexposed portion.
[0600] B: 1 to 3 residues were observed in a 1.1 μm square of the unexposed portion.
[0601] C: 4 to 10 residues were observed in a 1.1 μm square of the unexposed portion.
[0602] D: Eleven or more residues were observed in a 1.1 μm square of the unexposed portion.
[0603] <Evaluation of defects>
[0604] Each coloring composition immediately after production was applied to a silicon wafer having a diameter of 8 inches (20.32 cm) by CLEAN TRACK ACT-8 (manufactured by Tokyo Electron Limited), and then preheated (prebaked) was performed at 100° C. for 120 seconds to produce a film having a thickness of 0.8 μm. The silicon wafer having the film formed thereon was inspected by a defect inspection device Complus3 manufactured by Applied Materials technology, and defective portions were detected, and the number of defects having a size of 1 μm or more on the entire surface of the wafer was counted.
[0605] (Evaluation Criteria)
[0606] A: Less than 5.
[0607] B: More than 5 and less than 20.
[0608] C: more than 20 and 50 or less.
[0609] D: More than 50.
[0610] <Evaluation of heat resistance>
[0611] CT-4000 (manufactured by FUJIFILM Flectronic Materials Co., LTD.) was applied to a glass substrate by spin coating to a film thickness of 0.1 μm, and heated at 220° C. for 1 hour using a hot plate to form a base layer. Each coloring composition was applied to the glass substrate with the base layer by spin coating, and then heated at 100° C. for 2 minutes using a hot plate to obtain a coating film. The obtained coating film was irradiated with light of a wavelength of 365 nm at an exposure amount of 500 mJ / cm 2 Exposure was performed. Next, heating was performed at 220°C for 5 minutes using a hot plate to obtain a film with a thickness of 0.5 μm. Regarding the obtained film, the transmittance (transmittance) in the range of 400 to 700 nm was measured using MCPD-3000 manufactured by Otsuka Electronics Co., Ltd. Next, the film produced in the above was heated at 265°C for 5 minutes. The transmittance of the heated film was measured, the maximum value of the change in transmittance was found, and the heat resistance was evaluated according to the following criteria. The transmittance of each sample was measured 5 times, and the average value of the 3 results excluding the maximum and minimum values was used. In addition, the maximum value of the change in transmittance refers to the change in the wavelength at which the change in the transmittance of the film before and after heating in the range of wavelengths of 400 to 700 nm is the largest.
[0612] (Evaluation Criteria)
[0613] A: The maximum value of the change in transmittance is 1% or less.
[0614] B: The maximum value of the change in transmittance is more than 1% and less than 2%.
[0615] C: The maximum value of the change in transmittance is more than 2% and less than 3%.
[0616] D: The maximum value of the change in transmittance exceeds 3%.
[0617] [Table 14]
[0618]
[0619] As shown in the above table, the examples were excellent in heat resistance and result evaluation and also excellent in developability.
[0620] As a result of conducting the test for evaluating the above-mentioned defects using the dispersion (D-1) instead of the colored composition, the evaluation result was A, which was excellent.
[0621] A coloring composition was prepared in the same manner except that the photopolymerization initiator of Example 1 was changed to a thermal polymerization initiator (tert-butyl perbenzoate). The coloring composition was evaluated for defects and heat resistance, and the evaluation results for defects and heat resistance were both A, indicating excellent results.
[0622] (Example 1001)
[0623] The green coloring composition was applied to a silicon wafer by spin coating so that the film thickness after film formation was 1.0 μm. Then, the film was heated at 100° C. for 2 minutes using a hot plate. Then, an i-ray stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.) was used at 1000 mJ / cm 2The exposure amount was exposed through a mask with a 2μm square dot pattern. Then, a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) was used to perform spin immersion development at 23°C for 60 seconds. Then, it was rinsed by spin spraying and further washed with pure water. Next, a hot plate was used to heat at 200°C for 5 minutes, thereby patterning the green coloring composition to form a green pixel. Similarly, the red coloring composition and the blue coloring composition were patterned by the same process to form red pixels and blue pixels in sequence, thereby forming a color filter having green pixels, red pixels and blue pixels. In the color filter, the green pixel is formed in a Bayer pattern, and in the adjacent area, the red pixel and the blue pixel are formed in an island pattern. The obtained color filter is embedded in a solid-state imaging element according to a known method. The solid-state imaging element has suitable image recognition capabilities. In addition, as a green coloring composition, the coloring composition of Example 57 was used. As a red coloring composition, the coloring composition of Example 58 was used. The blue coloring composition uses a composition manufactured by the following method.
[0624] (Method for producing blue coloring composition)
[0625] The following components were mixed and stirred, and then filtered through a nylon filter (manufactured by NIHON PALL Corporation) having a pore size of 0.45 μm to prepare a blue coloring composition.
[0626] Blue pigment dispersion: 30.47 parts by mass
[0627] Dye 1: 2.64 parts by mass
[0628] Resin 1: 0.01 parts by mass
[0629] Resin 2: 0.04 parts by mass
[0630] Polymerizable compound 1: 1.56 parts by mass
[0631] Photopolymerization initiator 2: 0.57 parts by mass
[0632] Additive 1: 0.35 parts by mass
[0633] Epoxy compound 1: 0.46 parts by mass
[0634] Surfactant 1: 2.00 parts by mass (as 1% by mass PGMEA solution)
[0635] Propylene glycol monomethyl ether acetate: 5.70 parts by mass
[0636] Cyclohexanone: 55.4 parts by mass
[0637] Propylene glycol monomethyl ether: 0.8 parts by mass
[0638] The raw materials used to prepare the blue coloring composition are as follows.
[0639] Blue pigment dispersion
[0640] A mixed solution consisting of 15 parts by mass of CI Pigment Blue 15:6, 2.2 parts by mass of a dispersant (Disperbyk-161, manufactured by BYK Chemie GmbH), 2.2 parts by mass of a resin 3, and 80.6 parts by mass of a solvent 1 was mixed and dispersed for 3 hours using a bead mill (zirconia microbeads with a diameter of 0.3 mm). Then, a high-pressure disperser NANO-3000-10 (manufactured by Nippon Bee Chemical Co., Ltd.) with a decompression mechanism was used to disperse the mixture at 2000 kg / cm 2 The dispersion treatment was carried out at a flow rate of 500 g / min under a pressure of . This dispersion treatment was repeated 10 times to obtain a blue pigment dispersion.
[0641] 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)
[0642] [Chemical formula 46]
[0643]
[0644] Resin 1: 40% by mass PGMEA solution of a resin having the following structure (the numerical values attached to the main chain are molar ratios; weight average molecular weight = 11,000)
[0645] [Chemical formula 47]
[0646]
[0647] Resin 2: 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)
[0648] [Chemical formula 48]
[0649]
[0650] ·Polymerizable compound 2: A compound having the following structure
[0651] [Chemical formula 49]
[0652]
[0653] Photopolymerization initiator 1: a compound having the following structure
[0654] [Chemical formula 50]
[0655]
[0656] Additive 1: a compound having the following structure (potassium N,N-bis(pentafluoroethanesulfonyl)imide)
[0657] [Chemical formula 51]
[0658]
[0659] · Epoxy compound 1: a compound having the following structure
[0660] [Chemical formula 52]
[0661]
[0662] Surfactant 1: Surfactant 1 mentioned above
[0663] (Example 1002)
[0664] The cyan coloring composition was applied to a silicon wafer by spin coating so that the film thickness after film formation was 1.0 μm. Then, the film was heated at 100° C. for 2 minutes using a hot plate. Then, an i-ray stepper exposure apparatus FPA-3000i5+ (manufactured by Canon Inc.) was used at 1000 mJ / cm 2 The exposure amount was exposed through a mask with a 2μm square dot pattern. Then, a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) was used to perform spin immersion development at 23°C for 60 seconds. Then, it was rinsed by spin spraying and further washed with pure water. Next, a hot plate was used to heat at 200°C for 5 minutes, thereby patterning the cyan coloring composition to form cyan pixels. Similarly, the yellow coloring composition and the magenta coloring composition were patterned by the same process to form yellow pixels and magenta pixels in sequence, thereby forming a color filter having cyan pixels, yellow pixels and magenta pixels. In the color filter, the cyan pixels are formed in a Bayer pattern, and in the adjacent areas, the yellow pixels and magenta pixels are formed in an island pattern. The obtained color filter is embedded in a solid-state imaging element according to a known method. The solid-state imaging element has suitable image recognition capabilities. In addition, as a yellow coloring composition, the coloring composition of Example 1 was used. As for the cyan coloring composition and the magenta coloring composition, compositions produced by the following methods were used.
[0665] (Method for producing cyan coloring composition and magenta coloring composition)
[0666] The color materials of the types described in the following table, the dispersants of the types described in the following table, and a part of the solvents described in the following table are mixed, 230 parts by mass of zirconium oxide microbeads with a diameter of 0.3 mm are added, and a dispersion treatment is performed for 5 hours using a paint stirrer. The microbeads are separated by filtration to prepare a pigment dispersion liquid with a solid content of 20% by weight. Next, the obtained pigment dispersion liquid, the residual solvent of the types described in the following table, the adhesive of the types described in the following table, the polymerizable compound of the types described in the following table, the photopolymerization initiator of the types described in the following table, the ultraviolet absorber of the types described in the following table, the surfactant of the types described in the following table, and the epoxy compound of the types described in the following table are mixed to prepare a coloring composition. The following table shows the blending amount of each component in each coloring composition. The numerical value of the blending amount of each component is mass parts.
[0667] [Table 15]
[0668]
[0669] The raw materials represented by the above abbreviations are as follows.
[0670] (color material)
[0671] PB15∶4:CI Pigment Blue 15∶4
[0672] PR122: CI Pigment Red 122
[0673] (Dispersants, Binders)
[0674] D1: Resin with the following structure (the values attached to the main chain are molar ratios, and the values attached to the side chains are the number of repeating units. Weight average molecular weight: 24,000)
[0675] [Chemical formula 53]
[0676]
[0677] D2: Resin with the following structure (the values attached to the main chain are molar ratios. Weight average molecular weight: 11000)
[0678] [Chemical formula 54]
[0679]
[0680] D3: Resin with the following structure (the values attached to the main chain are molar ratios, and the values attached to the side chains are the number of repeating units. Weight average molecular weight: 16,000)
[0681] [Chemical formula 55]
[0682]
[0683] D4: Efka PX 4300 (manufactured by BASF, acrylic resin)
[0684] (Polymerizable compound)
[0685] M1: a mixture of compounds of the following structures (a mixture in which the molar ratio of the left-hand compound (hexafunctional (meth)acrylate compound) to the right-hand compound (pentafunctional (meth)acrylate compound) is 7:3)
[0686] [Chemical formula 56]
[0687]
[0688] M2: Compound with the following structure
[0689] [Chemical formula 57]
[0690]
[0691] (Photopolymerization Initiator)
[0692] F1: Irgacure OXE02 (manufactured by BASF)
[0693] (Ultraviolet light absorber)
[0694] UV1: Compounds with the following structures
[0695] [Chemical formula 58]
[0696]
[0697] (Surfactant)
[0698] W1: Compound with the following structure (Mw = 14000, the % value indicating the ratio of repeating units is mol%, fluorine-based surfactant)
[0699] [Chemical formula 59]
[0700]
[0701] (Epoxides)
[0702] G1: EHPE-3150 (manufactured by Daicel Corporation, epoxy compound)
[0703] (Solvent)
[0704] S1: Propylene glycol monomethyl ether acetate
[0705] S2: Propylene glycol monomethyl ether
Claims
1. A coloring composition comprising: At least one compound S selected from the group consisting of a compound S-1 represented by formula (1) and a compound S-2 in which the compound S-1 is coordinated to a metal atom; pigment; Resin; and Solvents, In the formula, R 1 represents a hydrogen atom, R 2 ~R 9 Each independently represents a hydrogen atom, a halogen atom, an aryl group, a cyano group, a nitro group or a group represented by the formula (R-1), R 2 ~R 9 Two adjacent groups in are optionally bonded to form a ring; wherein R 2 ~R 9 At least one of the compounds contains a group represented by formula (R-1); -W 1 -(X 1 ) n (R-1) In formula (R-1), W 1 represents an n+1 valent connecting group, W 1 The n+1-valent linking group represented is selected from aliphatic hydrocarbon groups, aromatic hydrocarbon groups, triazine ring groups, -O-, -S-, -CO-, -COO-, -OCO-, -NR W -、-NR W CO-、-CONR W -、-NR W SO2-、-SO2NR W - and groups composed of these combinations, R W represents a hydrogen atom, an alkyl group or an aryl group, X 1 represents an acid group or a basic group, and n represents an integer of 1 to 5, X of the formula (R-1) 1 The acid groups represented are carboxyl, sulfonyl, phosphate, -SO2NHSO2Rf 1 The groups or their salts, Rf 1 represents a group containing a fluorine atom, X of the formula (R-1) 1 The basic group represented is an amino group or an ammonium group, wherein the amino group is -NRx 1 Rx 2 A group represented by pyrrolidinyl, piperidinyl, piperazinyl or morpholinyl, Rx 1 Rx 2 Each independently represents a hydrogen atom or an alkyl group.
2. The coloring composition according to claim 1, wherein X of the formula (R-1) 1 It is a basic base.
3. The coloring composition according to claim 1, wherein The compound S-2 is a compound represented by formula (1a), In the formula, R 1 represents a hydrogen atom, R 2 ~R 9 Each independently represents a hydrogen atom, a halogen atom, an aryl group, a cyano group, a nitro group or a group represented by the formula (R-1), R 2 ~R 9 Two adjacent groups in M are optionally bonded to form a ring, 1 represents a metal atom to which a ligand is optionally coordinated, wherein R 2 ~R 9 At least one of them contains a group represented by the above formula (R-1).
4. The coloring composition according to claim 3, wherein In the formula (1a), M 1 It is a copper atom to which a ligand is optionally coordinated or a zinc atom to which a ligand is optionally coordinated.
5. The coloring composition according to claim 1, wherein The pigment includes at least one selected from the group consisting of a yellow pigment, a green pigment, and a red pigment.
6. The coloring composition according to claim 1, wherein The pigment includes a pigment having a metal atom.
7. The coloring composition according to claim 6, wherein The pigment having a metal atom includes an azomethine metal complex.
8. The coloring composition according to claim 7, wherein The azomethine metal complex includes at least one selected from the group consisting of an azomethine copper complex and an azomethine zinc complex.
9. The colored composition according to any one of claims 1 to 8, wherein The compound S is contained in an amount of 1 to 30 parts by mass based on 100 parts by mass of the pigment. 10 . The colored composition according to claim 1 , further comprising a polymerizable compound and a photopolymerization initiator. 11 . The colored composition according to claim 1 , which is used for a color filter or for an infrared transmission filter. 12 . The colored composition according to claim 1 , which is used for a solid-state imaging element.
13. A film obtained from the colored composition according to any one of claims 1 to 12.
14. An optical filter comprising the film according to claim 13. 15 . A solid-state imaging element comprising the film according to claim 13 . 16 . An image display device comprising the film according to claim 13 .
Citation Information
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