Coloring composition, film, filter, solid-state imaging device, image display device, and compound
By using a coloring composition in which a coloring agent coordinated with a specific structural compound Y on a metal atom, the problem of insufficient light resistance in the film in the prior art is solved, and the formation of a film with excellent light resistance is achieved, and it is suitable for color filters and infrared transmission filters.
Patent Information
- Application Number
- CN202280010528.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-12-27
- Filing Date
- 2022-01-28
- Publication Date
- 2025-07-25
- Estimated Expiration
- 2042-01-28
AI Technical Summary
The film using a methmethylazo copper complex pigment in the prior art is insufficient in light resistance and cannot meet further light resistance requirements.
A coloring composition containing a colorant that coordinates a specific structural compound Y on a metal atom. Compound Y is represented by formula (1), satisfies certain structural requirements and can be used in combination with a resin.
A film with excellent light resistance is formed, suitable for color filters and infrared transmission filters, and the light resistance of the film is improved.
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Figure CN116848199B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a coloring composition containing a colorant. Further, the present invention relates to a film, a filter, a solid-state imaging device, and an image display device using the coloring composition. Further, the present invention relates to a methylene azo metal complex compound. Background Art
[0002] In recent years, with the popularization of digital cameras, mobile phones with cameras, etc., the demand for solid-state imaging devices such as charge-coupled device (CCD) image sensors has increased significantly. As a key device for displays or optical elements, color filters are used. Color filters usually have pixels of the three primary colors, red, green, and blue, and function to decompose transmitted light into the three primary colors.
[0003] The colored pixels of each color of the color filter are manufactured using a coloring composition containing a colorant. Patent Document 1 describes a pigment composition for a color filter, which contains a phthalocyanine-based pigment and a methylene azo copper complex-based pigment, and the mass ratio of the phthalocyanine-based pigment to the methylene azo copper complex-based pigment is 99.9 / 0.1 to 96.5 / 3.5.
[0004] Prior Art Documents
[0005] Patent Documents
[0006] Patent Document 1: International Publication No. 2019 / 022051 Summary of the Invention
[0007] Technical Problem to be Solved by the Invention
[0008] In recent years, there has been a demand for further improving the light resistance of a film formed using a coloring composition containing a colorant.
[0009] Here, in Patent Document 1, C.I. Pigment Yellow 129 is used as the methylene azo copper complex-based pigment. C.I. Pigment Yellow 129 is a compound having the following structure. According to the research of the present inventors, it has been found that the light resistance of the film obtained by using the composition containing the methylene azo copper complex-based pigment described in the examples of Patent Document 1 is not sufficient and there is room for improvement.
[0010] [Chemical Formula 1]
[0011]
[0012] Therefore, an object of the present invention is to provide a coloring composition capable of forming a film having excellent light resistance. Another object of the present invention is to provide a film, a filter, a solid-state imaging device, an image display device, and a compound.
[0013] Means for solving technical problems
[0014] 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.
[0015] <1> A coloring composition comprising a coloring agent and a resin, wherein the coloring agent comprises a compound Y in which a compound represented by formula (1) is coordinated to a metal atom,
[0016] [Chemical formula 2]
[0017]
[0018] In formula (1), R 1 represents a hydrogen atom, an alkyl group or an aryl group,
[0019] X 2 ~X 9 Each independently represents a nitrogen atom, CH or CR x ,
[0020] R x represents a substituent,
[0021] In X 2 ~X 9 The two adjacent ones are CR x In the case of two adjacent CR x R x They can bond to each other to form a ring,
[0022] Wherein, formula (1) satisfies any of the following requirements 1 to 4:
[0023] Requirements1X 3 ~X 5 The two adjacent ones are CR x , and the two adjacent CR x R x bonded to each other to form a ring,
[0024] Requirement 2X 2 and X 3 CR x , and X 2 The CR indicated x R x With X 3 The CR indicated x R x bonded to form a heterocyclic ring,
[0025] Requirement 3X 6 ~X 9 The two adjacent ones are CR xand two adjacent CRs x 's R x are bonded to each other to form a ring.
[0026] Requirement 4X 2 and X 3 at least one of them is CH, and X 2 to X 9 at least one of them is CR x .
[0027] <2>The coloring composition according to <1>, wherein
[0028] X in the above formula (1) 6 to X 9 two adjacent ones are CR x and two adjacent CRs x 's R x are bonded to each other to form a ring.
[0029] <3>The coloring composition according to <1> or <2>, wherein
[0030] X in the above formula (1) 2 to X 9 at least one of them is CR x , R x is a group containing a heteroatom.
[0031] <4>The coloring composition according to any one of <1> to <3>, wherein
[0032] X in the above formula (1) 2 to X 9 at least one of them is CR x , R x represents nitro, cyano, -NR 101 R 102 , -OR 103 , -SR 104 , -COOR 105 , -OCOR 106 , -SO2R 107 , -SO2NR 108 R 109 , -SO2OR 110 , -CONR 111 R 112 or -NR 113 COR 114 , R 101 and R 102 each independently represents a hydrogen atom, an alkyl group or an aryl group, and R 101 and R 102 can be bonded to form a ring, and R 103~R 114 Each independently represents an alkyl group or an aryl group.
[0033] <5>The coloring composition according to any one of <1> to <4>, wherein
[0034] The above-mentioned metal atom is a copper atom or a zinc atom.
[0035] <6>The coloring composition according to any one of <1> to <4>, wherein
[0036] The above-mentioned metal atom is a copper atom.
[0037] <7>The coloring composition according to any one of <1> to <6>, wherein
[0038] The maximum absorption wavelength of the above-mentioned compound Y is in the range of 400 to 700 nm.
[0039] <8>The coloring composition according to any one of <1> to <7>, wherein
[0040] The above-mentioned colorant further contains a green colorant.
[0041] <9>The coloring composition according to any one of <1> to <8>, which further contains a polymerizable compound and a photoinitiator.
[0042] <10>The coloring composition according to any one of <1> to <9>, which is used for a color filter or an infrared transmission filter.
[0043] <11>A film obtained from the coloring composition according to any one of <1> to <10>.
[0044] <12>A filter having the film described in <11>.
[0045] <13>A solid-state imaging device having the film described in <11>.
[0046] <14>An image display device having the film described in <11>.
[0047] <15>A compound in which a compound represented by the formula (1) is coordinated to a metal atom,
[0048] [Chemical formula 3]
[0049]
[0050] In the formula (1), R 1 represents a hydrogen atom, an alkyl group or an aryl group,
[0051] X 2 ~X9 Each independently represents a nitrogen atom, CH or CR x ,
[0052] R x represents a substituent,
[0053] In X 2 ~X 9 if two adjacent ones are CR x in the case of, the two adjacent CR x of the R x can bond to each other to form a ring,
[0054] Among them, formula (1) satisfies any one of the following requirements 1 to 4,
[0055] Requirement 1 X 3 ~X 5 if two adjacent ones are CR x , and the two adjacent CR x of the R x bond to each other to form a ring,
[0056] Requirement 2 X 2 and X 3 are CR x , and the CR 2 represented by X x of the R x bonds to the R 3 of the CR x represented by X x to form a heterocyclic ring,
[0057] Requirement 3 X 6 ~X 9 if two adjacent ones are CR x , and the two adjacent CR x of the R x bond to each other to form a ring,
[0058] Requirement 4 At least one of X 2 and X 3 is CH, and at least one of X 2 ~X 9 is CR x .
[0059] Advantages of the Invention
[0060] According to the present invention, a coloring composition capable of forming a film with excellent light resistance can be provided. Moreover, a film, a filter, a solid-state imaging device, an image display device, and a compound can be provided. Detailed Embodiments
[0061] Hereinafter, the content of the present invention will be described in detail.
[0062] In this specification, "~" is used to mean including the numerical values described before and after it as the lower limit value and the upper limit value.
[0063] In the notation of groups (atomic groups) in this specification, the notation without indicating substituted or unsubstituted includes groups (atomic groups) without substituents, and also includes groups (atomic groups) with substituents. For example, "alkyl" includes not only alkyl without substituents (unsubstituted alkyl), but also alkyl with substituents (substituted alkyl).
[0064] In this specification, unless otherwise specified, "exposure" includes not only exposure using light, but also drawing using particle beams such as electron beams and ion beams. And as the light used in exposure, there can be mentioned actinic rays or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet rays typified by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
[0065] In this specification, "(meth)acrylate" means both or either of acrylate and methacrylate, "(meth)acrylic acid" means both or either of acrylic acid and methacrylic acid, and "(meth)acryloyl" means both or either of acryloyl and methacryloyl.
[0066] In this specification, Me in the structural formula represents methyl, Et represents ethyl, Bu represents butyl, and Ph represents phenyl.
[0067] In this specification, the weight average molecular weight and the number average molecular weight are polystyrene conversion values measured by the GPC (gel permeation chromatography) method.
[0068] In this specification, the total solid content means the total mass of the components obtained by removing the solvent from all the components of the composition.
[0069] In this specification, a pigment means a coloring material that is not easily soluble in a solvent.
[0070] In this specification, the term "process" includes not only independent processes, but also, even in cases where it cannot be clearly distinguished from other processes, as long as it exhibits the expected function of that process, it is also included in this term.
[0071] <Coloring composition>
[0072] The coloring composition of the present invention is a coloring composition containing a colorant and a resin, and is characterized in that the above colorant contains Compound Y in which a compound represented by the formula (1) is coordinated to a metal atom.
[0073] The coloring composition according to the present invention can form a film having excellent light resistance. The detailed reason for obtaining such an effect is not clear yet, but it can be speculated as follows. The compound Y used as a colorant in the coloring composition of the present invention easily forms an association in the film, and can effectively conduct intermolecular electron transfer. Therefore, it is speculated that a film having excellent light resistance can be formed by using the coloring composition of the present invention.
[0074] The coloring composition of the present invention can be preferably used as a coloring composition for a color filter or an infrared transmission filter. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter or a coloring composition for forming an infrared transmission filter, and can be more preferably used as a coloring composition for forming pixels of a color filter. As the types of pixels, red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, etc. can be mentioned, preferably red pixels, green pixels and yellow pixels, more preferably red pixels or green pixels, and further preferably green pixels.
[0075] When using the coloring composition of the present invention to form a film with a thickness of 0.65 μm, the wavelength at which the light transmittance of the film 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 wavelengths at which the light transmittance becomes 50% preferably exist in the wavelength ranges of 470 to 520 nm and 575 to 625 nm, respectively. In this manner, the wavelength on the short wavelength side at which the light transmittance becomes 50% preferably exists in the wavelength range of 475 to 520 nm, more preferably exists in the wavelength range of 480 to 520 nm. And, the wavelength on the long wavelength side at which the light transmittance becomes 50% preferably exists in the wavelength range of 580 to 620 nm, more preferably exists in the wavelength range of 585 to 615 nm. The coloring composition capable of forming a film having such spectral characteristics can be preferably used as a coloring composition for forming green pixels of a color filter.
[0076] Hereinafter, each component used in the coloring composition of the present invention will be described.
[0077] 《Colorant》
[0078] The coloring composition of the present invention contains a colorant. As the colorant, a compound Y containing a compound in which a compound represented by the formula (1) is coordinated to a metal atom can be used. Compound Y is a methylene azo metal complex. Compound Y is also a compound of the present invention.
[0079] [Chemical formula 4]
[0080]
[0081] In formula (1), R1 represents a hydrogen atom, an alkyl group or an aryl group,
[0082] X 2 ~X 9 each independently represents a nitrogen atom, CH or CR x ,
[0083] R x represents a substituent,
[0084] When two adjacent ones in X 2 ~X 9 are CR x in the case of, two adjacent CR x 's R x can bond to each other to form a ring,
[0085] wherein, formula (1) satisfies any one of the following requirements 1 to 4,
[0086] Requirement 1 X 3 ~X 5 two adjacent ones in are CR x , and two adjacent CR x 's R x bond to each other to form a ring,
[0087] Requirement 2 X 2 and X 3 are CR x , and the R 2 represented by X x 's CR x bonds with the R 3 represented by X x 's CR x to form a heterocyclic ring,
[0088] Requirement 3 X 6 ~X 9 two adjacent ones in are CR x , and two adjacent CR x 's R x bond to each other to form a ring,
[0089] Requirement 4 At least one of X 2 and X 3 is CH, and at least one of X 2 ~X 9 is CR x .
[0090] The R of formula (1) 1 The number of carbon atoms of the alkyl group represented is preferably 1 to 30, more preferably 1 to 15, and still more preferably 1 to 8. The alkyl group can be any of linear, branched, and cyclic, preferably linear or branched, and still more preferably linear. The alkyl group may have a substituent. As the substituent, the substituent T described later can be mentioned.
[0091] R in formula (1) 1 The 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. As the substituent, the substituent T described later can be mentioned.
[0092] R in formula (1) 1 is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
[0093] X in formula (1) 2 ~X 9 each independently represents a nitrogen atom, CH or CR x , R x represents a substituent. As the substituent represented by R x , the substituent T described later can be mentioned. R x The substituent represented is preferably a group containing a heteroatom, and more preferably a specific functional group A described later. X in formula (1) 2 ~X 9 is preferably each independently represents CH or CR x . And, considering the reason that a film with more excellent light resistance can be formed, it is also preferred that at least one of X 2 ~X 9 in formula (1) is CR x , and R x is a group containing a heteroatom (preferably a specific functional group A described later).
[0094] As the specific functional group A, nitro, cyano, -NR 101 R 102 , -OR 103 , -SR 104 , -COOR 105 , -OCOR 106 , -SO2R 107 , -SO2NR 108 R 109 , -SO2OR 110 , -CONR 111 R 112 and -NR 113 COR 114 can be mentioned, and preferably nitro, cyano, -NR 101 R 102 , -OR 103 , -SR104 and -C00R 105 , more preferably -NR 101 R 102 and -OR 103 . R 101 and R 102 each independently represents a hydrogen atom, an alkyl group or an aryl group, and R 101 and R 102 may be bonded to form a ring, and R 103 ~R 114 each independently represents an alkyl group or an aryl group.
[0095] R 101 ~R 114 The number of carbon atoms of the alkyl group represented by is preferably 1 to 10, more preferably 1 to 5, further preferably 1 to 3, and particularly preferably 1 or 2. The alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. As the substituent, the substituent T described later can be cited. R 101 ~R 114 The alkyl group represented by is preferably a methyl group or an ethyl group.
[0096] R 101 ~R 114 The number of carbon atoms of the aryl group represented by 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 later can be cited.
[0097] R 101 and R 102 each independently is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group. R 103 ~R 114 each independently is preferably an alkyl group, and more preferably a methyl group or an ethyl group.
[0098] In the case where two adjacent ones in X 2 ~X 9 of formula (1) are CR x , for two adjacent CR x the R xThey can be bonded to each other to form a ring. The formed ring can be a hydrocarbon ring or a heterocyclic ring. Moreover, the hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. Examples of the heteroatoms contained in the heterocyclic ring include a nitrogen atom, a sulfur atom, and an oxygen atom. The heterocyclic ring is preferably a 5-membered ring or a 6-membered ring. Specific examples of the formed ring include hydrocarbon rings such as a benzene ring and a naphthalene ring, and heterocyclic rings such as a pyrrole ring, a furan ring, a thiophene ring, a pyridine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, an imidazoline ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, an indole ring, an isoindole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a benzotriazole ring, a purine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a cinnoline ring, a pteridinyl ring, a pyrrolidine ring, a piperidine ring, a tetrahydrofuran ring, a tetrahydropyran ring, a tetrahydrothiophene ring, and a tetrahydrothiopyran ring. The formed ring described above may further have a substituent. Examples of the substituent include the substituent T described later. The substituent is preferably a group containing a heteroatom, and more preferably the specific functional group A described above.
[0099] Formula (1) satisfies any one of the above-mentioned requirements 1 to 4.
[0100] Requirement 1 is as follows: X 3 ~X 5 Two adjacent ones among them are CR x and the R x of two adjacent CRs x are bonded to each other to form a ring. Examples of the ring formed by the bonding of R x to each other include the above-mentioned rings, preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring. The ring formed by the bonding of R x to each other may further have a substituent. Examples of the substituent include the substituent T described later. The substituent is preferably a group containing a heteroatom, and more preferably the specific functional group A described above.
[0101] Specific examples of Requirement 1 include the manner in which X 3 and X 4 are each independently CR x and the R 3 of the CR x represented by X x is bonded to the R 4 of the CR x represented by X x to form a ring, and the manner in which X 4 and X 5 are each independently CR x and the R 4 of the CR x represented by X x is bonded to the R 5 of the CR x represented by X x to form a ring.
[0102] In Requirement 1, it is also preferred that at least one of X 6 ~X 9 is CR x and R x is a group containing a heteroatom (preferably the specific functional group A mentioned above).
[0103] Requirement 2 is as follows: X 2 and X 3 are CR x and the R 2 of the CR x represented by X x is bonded to the R 3 of the CR x represented by X x to form a heterocycle. As the heterocycle formed by bonding of R x to each other, the above-mentioned heterocycle can be cited. The heterocycle formed by bonding of R x to each other may also have a substituent. As the substituent, the substituent T described later can be cited. The substituent is preferably a group containing a heteroatom, more preferably the specific functional group A mentioned above.
[0104] In Requirement 2, it is also preferred that at least one of X 6 ~X 9 is CR x and R x is a group containing a heteroatom (preferably the specific functional group A mentioned above).
[0105] Requirement 3 is as follows: Two adjacent ones of X 6 ~X 9 are CR x and the R x of the two adjacent CR x are bonded to each other to form a ring. As the ring formed by bonding of R x to each other, the above-mentioned ring can be cited, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring. The ring formed by bonding of R x to each other may also have a substituent. As the substituent, the substituent T described later can be cited. The substituent is preferably a group containing a heteroatom, more preferably the specific functional group A mentioned above.
[0106] As a specific example of Requirement 3, there can be cited a mode in which X 6 and X 7 are each independently CR x and the R 6 of the CR x represented by X x is bonded to the R 7 of the CR x represented by X x to form a ring, X7 and X 8 are each independently CR x and X 7 the CR represented by x the R of x and X 8 the CR represented by x the R of x bond to form a ring, and the way that X 8 and X 9 are each independently CR x and X 8 the CR represented by x the R of x and X 9 the CR represented by x the R of x bond to form a ring. Considering the reason for forming a film with more excellent light resistance, it is preferably that X 6 and X 7 are each independently CR x and X 6 the CR represented by x the R of x and X 7 the CR represented by x the R of x bond to form a ring or X 7 and X 8 are each independently CR x and X 7 the CR represented by x the R of x and X 8 the CR represented by x the R of x bond to form a ring. More preferably, it is the way that X 7 and X 8 are each independently CR x and X 7 the CR represented by x the R of x and X 8 the CR represented by x the R of x bond to form a ring.
[0107] In Requirement 3, when two adjacent ones among X 2 ~X 5 are CR x the two adjacent CR x the R of x can bond to each other to form a ring. As the ring formed by the bonding of R x to each other, the above-mentioned rings can be cited. Preferably, it is a benzene ring or a naphthalene ring, and more preferably a benzene ring. Rx The ring formed by bonding to each other may also have a substituent. As the substituent, the following substituent D can be mentioned. The substituent is preferably a group containing a heteroatom, and more preferably the above-mentioned specific functional group A.
[0108] In requirement 3, it is also preferable that X 2 ~X 5 at least one of which is CR x and R x is a group containing a heteroatom (preferably the above-mentioned specific functional group A).
[0109] Requirement 4 is as follows: X 2 and X 3 at least one of which is CH, and X 2 ~X 9 at least one of which is CR x . R x represents a substituent. In requirement 4, it is preferable that X 2 ~X 9 1 to 4 of CR x , more preferably 1 or 2 are CR x . As the substituent represented by R x , the following substituent T can be mentioned. The substituent is preferably a group containing a heteroatom, and more preferably the above-mentioned specific functional group A.
[0110] Formula (1) preferably satisfies any one of the above requirements 1, 3 or 4, more preferably satisfies requirement 3 or 4, and further preferably satisfies requirement 3.
[0111] The compound represented by formula (1) is preferably the compound represented by formula (1-1).
[0112] [Chemical formula 5]
[0113]
[0114] In formula (1-1), R 1 represents a hydrogen atom, an alkyl group or an aryl group,
[0115] R 2 ~R 9 each independently represents a hydrogen atom or a substituent,
[0116] R 2 ~R 9 adjacent two of which can bond to form a ring;
[0117] wherein, formula (1-1) satisfies any one of the following requirements 1a to 4a;
[0118] Requirement 1a R 3 ~R5 Two adjacent ones in are bonded to form a ring;
[0119] Requirement 2a R 2 is bonded to R 3 to form a heterocyclic ring;
[0120] Requirement 3a R 6 ~R 9 Two adjacent ones in are bonded to form a ring;
[0121] Requirement 4a R 2 and R 3 at least one of them is a hydrogen atom and R 2 ~R 9 at least one of them is a substituent.
[0122] R in formula (1-1) 1 has the same meaning as R in formula (1). 1
[0123] As R in formula (1-1) 2 ~R 9 The substituents represented by can be exemplified by the following substituent T, preferably a group containing a heteroatom, more preferably the above-mentioned specific functional group A.
[0124] In formula (1-1), R 2 ~R 9 Two adjacent ones in can be bonded to form a ring. As the formed ring, the above-mentioned rings can be exemplified. The above-formed ring can also have a substituent. As the substituent, the following substituent T can be exemplified. The substituent is preferably a group containing a heteroatom, more preferably the above-mentioned specific functional group A.
[0125] Formula (1-1) satisfies any of the above requirements 1a to 4a.
[0126] Requirement 1a is as follows: R 3 ~R 5 Two adjacent ones in are bonded to form a ring. As the formed ring, the above-mentioned rings can be exemplified, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring. The above-formed ring can also have a substituent. As the substituent, the following substituent T can be exemplified. The substituent is preferably a group containing a heteroatom, more preferably the above-mentioned specific functional group A.
[0127] As a specific example of Requirement 1a, the bonding mode of R 3 bonded to R 4 to form a ring and the bonding mode of R 4 bonded to R 5 to form a ring can be exemplified.
[0128] In Requirement 1a, it is also preferred that R6 ~R 9 At least one of them is a heteroatom-containing group (preferably the specific functional group A as described above).
[0129] Requirement 2a is as follows: R 2 and R 3 are bonded to form a heterocycle. Examples of the formed heterocycle include the above-mentioned heterocycles. The formed heterocycle may also have a substituent. Examples of the substituent include the substituent T described later. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group A as described above.
[0130] In Requirement 2a, it is also preferred that at least one of R 6 ~R 9 is a heteroatom-containing group (preferably the specific functional group A as described above).
[0131] Requirement 3a is as follows: Two adjacent ones of R 6 ~R 9 are bonded to form a ring. Examples of the formed ring include the above-mentioned rings, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring. The formed ring may also have a substituent. Examples of the substituent include the substituent T described later. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group A as described above.
[0132] As a specific example of Requirement 3a, examples include the manner in which R 6 and R 7 are bonded to form a ring, the manner in which R 7 and R 8 are bonded to form a ring, the manner in which R 8 and R 9 are bonded to form a ring. Considering the reason for being able to form a film with more excellent light resistance, the manner in which R 6 and R 7 are bonded to form a ring or the manner in which R 7 and R 8 are bonded to form a ring is preferred, and the manner in which R 7 and R 8 are bonded to form a ring is more preferred.
[0133] In Requirement 3a, two adjacent ones of R 2 ~R 5 can be bonded to form a ring. Examples of the formed ring include the above-mentioned rings, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring. The formed ring may also have a substituent. Examples of the substituent include the substituent T described later. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group A as described above.
[0134] In Requirement 3a, it is also preferred that R 2 ~R5 at least one of them is a heteroatom-containing group (preferably the specific functional group A mentioned above).
[0135] Requirement 4a is as follows: R 2 and R 3 at least one of them is a hydrogen atom and R 2 ~R 9 at least one of them is a substituent. In Requirement 4a, preferably 1 to 4 of R 2 ~R 9 are substituents, more preferably 1 or 2 are substituents. As the substituent, the substituent T described later can be mentioned. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group A mentioned above.
[0136] Formula (1-1) preferably satisfies any one of the above-mentioned Requirement 1a, Requirement 3a, or Requirement 4a, more preferably satisfies Requirement 3a or Requirement 4a, and further preferably satisfies Requirement 3a.
[0137] In compound Y, as the metal atom coordinated by the compound represented by formula (1), copper atom, zinc atom, iron atom, titanium atom, aluminum atom, tin atom, magnesium atom, chromium atom, calcium atom, and silicon atom can be mentioned, preferably copper atom and zinc atom, more preferably copper atom. Compound Y can coordinate 1 compound represented by formula (1) on the metal atom, or can coordinate 2 or more. And, other ligands than the compound represented by formula (1) can also be coordinated on the metal atom. As the ligand, heterocyclic compounds (such as pyridine, pyrimidine, imidazole, pyrazole, triazole, tetrazole, quinoline, 1,10-phenanthroline, etc.), protic compounds (such as water, methanol, ethanol, etc.), amine compounds (such as triethylamine, N,N,N',N'-tetramethylenediamine, ethylenediaminetetraacetic acid, N,N,N",N"-pentamethyldiethylenetriamine, etc.), amide compounds (such as N,N-dimethylacetamide, N-methylpyrrolidone, etc.), dimethyl sulfoxide, sulfolane, nitrile compounds (such as acetonitrile, etc.), etc. can be mentioned. And, compound Y can be a binuclear complex. In the case where a compound represented by formula (1) is coordinated on the metal atom, as an example of compound Y, the compound represented by the following formula (1-1), the compound represented by formula (1-2), the compound represented by formula (1-3), and the compound represented by formula (1-4) can be mentioned. In the following formulas, M 1 ~M 5Each independently represents a metal atom. Further, compound Y may be a compound in which a ligand coordinates to a metal atom at a ratio of 1:3, a compound in which a ligand coordinates to a metal atom at a ratio of 1:4, a compound in which a ligand coordinates to a metal atom at a ratio of 2:3, or a compound in which a ligand coordinates to a metal atom at a ratio of 3:3. Further, a part of the ligand may deviate from the metal atom, or a compound other than the ligand may coordinate to the metal atom.
[0138] [Chemical formula 6]
[0139]
[0140] (Substituent T)
[0141] As the substituent T described above, the following groups can be mentioned. A halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (preferably an alkyl group having 1 to 30 carbon atoms), an alkenyl group (preferably an alkenyl group having 2 to 30 carbon atoms), an alkynyl group (preferably an alkynyl group having 2 to 30 carbon atoms), an aryl group (preferably an aryl group having 6 to 30 carbon atoms), a heterocyclic group (preferably a heterocyclic group having 1 to 30 carbon atoms), an amino group (preferably an amino group having 0 to 30 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 30 carbon atoms), an aryloxy group (preferably an aryloxy group having 6 to 30 carbon atoms), a heterocyclic oxy group (preferably a heterocyclic oxy group having 1 to 30 carbon atoms), an acyl group (preferably an acyl group having 2 to 30 carbon atoms), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms), a heterocyclic oxycarbonyl group (preferably a heterocyclic oxycarbonyl 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 0 to 30 carbon atoms), a carbamoyl group (preferably a carbamoyl group having 1 to 30 carbon atoms), an alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms), an arylthio group (preferably an arylthio group having 6 to 30 carbon atoms), a heterocyclic thio group (preferably a heterocyclic thio group having 1 to 30 carbon atoms), an alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 30 carbon atoms), an alkylsulfonylamino group (preferably an alkylsulfonylamino group having 1 to 30 carbon atoms), an arylsulfonyl group (preferably an arylsulfonyl group having 6 to 30 carbon atoms), an arylsulfonylamino group (preferably an arylsulfonylamino group having 6 to 30 carbon atoms), a heterocyclic sulfonyl group (preferably a heterocyclic sulfonyl group having 1 to 30 carbon atoms), a heterocyclic sulfonylamino group (preferably a heterocyclic sulfonylamino group having 1 to 30 carbon atoms), an alkylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms), an arylsulfinyl group (preferably an arylsulfinyl group having 6 to 30 carbon atoms), a heterocyclic sulfinyl group (preferably a heterocyclic sulfinyl group having 1 to 30 carbon atoms), a ureido group (preferably a ureido group having 1 to 30 carbon atoms), a hydroxyl group, a nitro group, a carboxyl group, a sulfo group, a phosphoric acid group, a carboxamide group, a sulfonamide group, an imide group, a phosphino group, a mercapto group, a cyano group, an alkylsulfinic acid group, an arylsulfinic acid group, an arylazo group, a heterocyclic azo group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a silyl group, a hydrazino group, an imino group. When these groups are groups that can be further substituted, they can also have substituents.
[0142] Compound Y can be a pigment or a dye.
[0143] The maximum absorption wavelength of compound Y preferably exists in the range of 400 to 700 nm, more preferably in the range of 400 to 600 nm.
[0144] As specific examples of compound Y, compounds (Y-1) to (Y-87) described in the following examples can be cited.
[0145] The colorant contained in the coloring composition of the present invention can also contain a colorant other than the above-mentioned compound Y. As other colorants used in combination, colored colorants such as green colorants, red colorants, yellow colorants, purple colorants, blue colorants, orange colorants, and black colorants can be cited. As other colorants, at least one selected from green colorants, red colorants, and orange colorants is preferred, at least one selected from green colorants and red colorants is more preferred, and a green colorant is further preferred. Other colorants can be pigments or dyes, but pigments are preferred. When using a pigment as other colorants, the interaction between the pigment as other colorants and compound Y easily promotes the formation of association and can form a film with more excellent light resistance. When using a green pigment as other colorants, such an effect is remarkable, and when using a phthalocyanine compound as the green pigment, the most remarkable effect can be exerted.
[0146] As red colorants, diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, methylene azo compounds, xanthene compounds, quinacridone compounds, perylene compounds, thioindigo compounds, etc. can be cited. From the reason of easily forming a film with more excellent light resistance, diketopyrrolopyrrole compounds, anthraquinone compounds, and azo compounds are preferred, and diketopyrrolopyrrole compounds are more preferred. And the red colorant is preferably a pigment.
[0147] Specific examples of the red colorant include C.I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, 297 and other red pigments. Further, as the red colorant, it is also possible to use diketopyrrolopyrrole compounds having at least one bromine atom substituted in the structure as described in Japanese Unexamined Patent Application Publication No. 2017-201384, diketopyrrolopyrrole compounds described in paragraphs 0016 to 0022 of Japanese Patent No. 6248838, diketopyrrolopyrrole compounds described in International Publication No. 2012 / 102399, diketopyrrolopyrrole compounds described in International Publication No. 2012 / 117965, brominated diketopyrrolopyrrole compounds described in Japanese Unexamined Patent Application Publication No. 2020-085947, naphthol azo compounds described in Japanese Unexamined Patent Application Publication No. 2012-229344, red colorants described in Japanese Patent No. 6516119, red colorants described in Japanese Patent No. 6525101, brominated diketopyrrolopyrrole compounds described in paragraph 0229 of Japanese Unexamined Patent Application Publication No. 2020-090632, anthraquinone compounds described in Korean Patent Application Publication No. 10-2019-0140741, anthraquinone compounds described in Korean Patent Application Publication No. 10-2019-0140744, perylene compounds described in Japanese Unexamined Patent Application Publication No. 2020-079396, diketopyrrolopyrrole compounds described in paragraphs 0025 to 0041 of Japanese Unexamined Patent Application Publication No. 2020-066702, and the like. Further, as the red colorant, it is also possible to use a compound having a structure in which an aryl group obtained by introducing a group bonded with an oxygen atom, a sulfur atom or a nitrogen atom into an aromatic ring is bonded to a diketopyrrolopyrrole skeleton.
[0148] As the red colorant, C.I. Pigment Red 122, 177, 254, 255, 264, 269, 272 are preferred, C.I. Pigment Red 254, 264, 272 are more preferred, and C.I. Pigment Red 254, 264 are further preferred.
[0149] As the green colorant, phthalocyanine compounds, squaric acid compounds, etc. can be mentioned. From the reason of being easy to form a film with more excellent light resistance, phthalocyanine compounds are preferred. And the green colorant is preferably a pigment.
[0150] Specific examples of the green colorant include green pigments such as C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66. And as the green colorant, a zinc halide phthalocyanine pigment 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 per molecule can also be used. As a specific example, the compound described in International Publication No. 2015 / 118720 can be mentioned. And as the green colorant, the compound described in Chinese Patent Application No. 106909027, the phthalocyanine compound having a phosphate ester as a ligand described in International Publication No. 2012 / 102395, the phthalocyanine compound described in Japanese Patent Application Laid-Open No. 2019-008014, the phthalocyanine compound described in Japanese Patent Application Laid-Open No. 2018-180023, the compound described in Japanese Patent Application Laid-Open No. 2019-038958, the aluminum phthalocyanine compound described in Japanese Patent Application Laid-Open No. 2020-070426, the core-shell pigment described in Japanese Patent Application Laid-Open No. 2020-076995, the diarylmethane compound described in Japanese Patent Application Laid-Open No. 2020-504758, etc. can also be used.
[0151] As the green colorant, C.I. Pigment Green 7, 36, 58, 62, 63 are preferred, and C.I. Pigment Green 36, 58 are more preferred.
[0152] Specific examples of the orange colorant include orange pigments such as C.I. Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73.
[0153] As the yellow colorant, azo compounds, methylene azo compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds can be cited. As specific examples of the yellow colorant, C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214, 215, 228, 231, 232, 233, 234, 235, 236 and other yellow pigments can be cited.
[0154] Moreover, as the yellow colorant, a nickel complex of azobarbituric acid having the following structure can also be used.
[0155] [Chemical formula 7]
[0156]
[0157] Also, as the yellow colorant, it is also possible to use the compounds described in paragraph 0281 of International Publication No. 2021 / 215133, the compounds described in Japanese Unexamined Patent Application Publication No. 2017-201003, the compounds described in Japanese Unexamined Patent Application Publication No. 2017-197719, the compounds described in paragraphs 0011 to 0062 and 0137 to 0276 of Japanese Unexamined Patent Application Publication No. 2017-171912, the compounds described in paragraphs 0010 to 0062 and 0138 to 0295 of Japanese Unexamined Patent Application Publication No. 2017-171913, the compounds described in paragraphs 0011 to 0062 and 0139 to 0190 of Japanese Unexamined Patent Application Publication No. 2017-171914, the compounds described in paragraphs 0010 to 0065 and 0142 to 0222 of Japanese Unexamined Patent Application Publication No. 2017-171915, the quinophthalone compounds described in paragraphs 0011 to 0034 of Japanese Unexamined Patent Application Publication No. 2013-054339, the quinophthalone compounds described in paragraphs 0013 to 0058 of Japanese Unexamined Patent Application Publication No. 2014-026228, the isoindoline compounds described in Japanese Unexamined Patent Application Publication No. 2018-062644, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2018-203798, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2018-062578, the quinophthalone compounds described in Japanese Patent No. 6432076, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2018-155881, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2018-111757, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2018-040835, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2017-197640, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2016-145282, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2014-085565, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2014-021139, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2013-209614, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2013-209435, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2013-181015, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2013-061622, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2013-032486, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2012-226110, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2008-074987, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2008-081565, the quinophthalone compounds described in Japanese Unexamined Patent Application Publication No. 2008-074986,The quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2008-074985, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2008-050420, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2008-031281, the quinophthalone compounds described in Japanese Patent Publication No. 48-032765, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2019-008014, the quinophthalone compounds described in Japanese Patent No. 6607427, the methylene dyes described in Japanese Patent Application Laid-Open No. 2019-073695, the methylene dyes described in Japanese Patent Application Laid-Open No. 2019-073696, the methylene dyes described in Japanese Patent Application Laid-Open No. 2019-073697, the methylene dyes described in Japanese Patent Application Laid-Open No. 2019-073698, the compounds described in Korean Patent Publication No. 10-2014-0034963, the compounds described in Japanese Patent Application Laid-Open No. 2017-095706, the compounds described in Taiwan Region Patent Application Publication No. 201920495, the compounds described in Japanese Patent No. 6607427, the compounds described in Japanese Patent Application Laid-Open No. 2020-033525, the compounds described in Japanese Patent Application Laid-Open No. 2020-033524, the compounds described in Japanese Patent Application Laid-Open No. 2020-033523, the compounds described in Japanese Patent Application Laid-Open No. 2020-033522, the compounds described in Japanese Patent Application Laid-Open No. 2020-033521, the compounds described in International Publication No. 2020 / 045200, the compounds described in International Publication No. 2020 / 045199, the compounds described in International Publication No. 2020 / 045197, the azo compounds described in Japanese Patent Application Laid-Open No. 2020-093994, the perylene compounds described in Japanese Patent Application Laid-Open No. 2020-083982, the perylene compounds described in International Publication No. 2020 / 105346, the quinophthalone compounds described in Japanese Patent Application Laid-Open No. 2020-517791, the compounds represented by the following formula (QP1), the compounds represented by the following formula (QP2). Also, from the viewpoint of improving the color value, substances obtained by polymerizing these compounds can also be preferably used.
[0158] [Chemical formula 8]
[0159]
[0160] In formula (QP1), X 1 ~X 16 each independently represents a hydrogen atom or a halogen atom, and Z 1represents an alkylene group having 1 to 3 carbon atoms. As a specific example of the compound represented by the formula (QP1), the compounds described in paragraph 0016 of Japanese Patent No. 6443711 can be cited.
[0161] [Chemical formula 9]
[0162]
[0163] In the formula (QP2), Y 1 ~Y 3 each independently represents a halogen atom. n and m represent integers from 0 to 6, and p represents an integer from 0 to 5. (n + m) is 1 or more. As a specific example of the compound represented by the formula (QP2), the compounds described in paragraphs 0047 to 0048 of Japanese Patent 6432077 can be cited.
[0164] As specific examples of the purple colorant, purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, 61 can be cited.
[0165] As specific examples of the blue colorant, blue pigments such as C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88 can be cited. Further, an aluminum phthalocyanine compound having a phosphorus atom can also be used as the blue colorant. As specific examples, the compounds described in paragraphs 0022 to 0030 of Japanese Patent Application Laid-Open No. 2012-247591 and paragraph 0047 of Japanese Patent Application Laid-Open No. 2011-157478 can be cited.
[0166] Further, as the color colorant, a triarylmethane dye polymer described in Korean Patent Publication No. 10-2020-0028160, a xanthene compound described in Japanese Patent Application Laid-Open No. 2020-117638, a phthalocyanine compound described in International Publication No. 2020 / 174991, or an isoindoline compound or a salt thereof described in Japanese Patent Application Laid-Open No. 2020-160279 can be used.
[0167] As the black colorant, examples include dibenzofuranone compounds, methylene azo compounds, perylene compounds, azo compounds, etc., and dibenzofuranone compounds and perylene compounds are preferred. As the dibenzofuranone compound, examples include the compounds described in Japanese Patent Application Laid-Open No. 2010-534726, Japanese Patent Application Laid-Open No. 2012-515233, Japanese Patent Application Laid-Open No. 2012-515234, etc., and can be obtained, for example, as "Irgaphor Black" manufactured by BASF. As the perylene compound, examples include the compounds described in paragraphs 0016 to 0020 of Japanese Patent Application Laid-Open No. 2017-226821, C.I. Pigment Black 31, 32, etc. As the methylene azo compound, examples include the compounds described in Japanese Patent Application Laid-Open No. 01-170601, Japanese Patent Application Laid-Open No. 02-034664, etc., and can be obtained, for example, as "CHROMO F[NE BLACK A1103" manufactured by Dainichiseika Color & Chemicals Mfg. Co., Ltd.
[0168] Regarding the preferred diffraction angles of various pigments, reference can be made to the descriptions in Japanese Patent No. 6561862, Japanese Patent No. 6413872, Japanese Patent No. 6281345, Japanese Patent Application Laid-Open No. 2020-026503, and Japanese Patent Application Laid-Open No. 2020-033526, and these contents are incorporated into this specification. Also, as the pyrrolopyrrole-based pigment, it is preferred that the crystal grain size in the plane direction corresponding to the maximum peak in the X-ray diffraction pattern among the 8 planes of (±1±1±1) in the lattice plane is as follows. Also, regarding the physical properties of the pyrrolopyrrole-based pigment, it is preferably set as described in paragraphs 0028 to 0073 of Japanese Patent Application Laid-Open No. 2020-097744.
[0169] The crystal grain size obtained from the half-value width of the peak from any crystal plane in the X-ray diffraction spectrum when the CuKα ray of the pigment is used as the X-ray source is preferably 0.1 nm to 100 nm, more preferably 0.5 nm to 50 nm, further preferably 1 nm to 30 nm, and particularly preferably 5 nm to 25 nm.
[0170] When the coloring composition of the present invention contains a green colorant, it can preferably be used as a coloring composition for forming a green pixel of a color filter. And when the coloring composition of the present invention contains a red colorant, it can preferably be used as a coloring composition for forming a red pixel of a color filter.
[0171] Moreover, the colorant contained in the coloring composition contains two or more kinds of color colorants and can form black from a combination of two or more kinds of color colorants. Such a coloring composition can preferably be used as a coloring composition for forming an infrared transmission filter. Examples of the combination of color colorants when forming black from a combination of two or more kinds of color colorants are as follows.
[0172] (1) A mode containing a red colorant, a blue colorant, and a yellow colorant.
[0173] (2) A mode containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant.
[0174] (3) A mode containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant.
[0175] (4) A mode containing a red colorant, a blue colorant, a yellow colorant, and a green colorant.
[0176] (5) A mode containing a yellow colorant and a purple colorant.
[0177] The content of the colorant in the total solid content of the coloring composition is preferably 40% by mass or more, more preferably 50% by mass or more, and further preferably 55% 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.
[0178] The content of compound Y in the colorant is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 15% by mass or more. The upper limit can also be set to 100% by mass, can also be set to 95% by mass or less, and can also be set to 90% by mass or less.
[0179] The content of compound Y in the total solid content of the coloring composition is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 7% by mass or more. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less, and further preferably 20% by mass or less.
[0180] When the coloring composition of the present invention is used as a coloring composition for forming a green pixel of a color filter, it is preferable to use a yellow coloring agent and a green coloring agent in the coloring agent. And compound Y is preferably a yellow coloring agent. The mass ratio of the yellow coloring agent to the green coloring agent is preferably yellow coloring agent∶green coloring agent = 30∶70 to 70∶30, more preferably 30∶70 to 60∶40, and further preferably 30∶70 to 50∶50. And the content of compound Y is preferably 5 to 60 parts by mass with respect to 100 parts by mass of the green coloring agent. The lower limit is preferably 10 parts by mass or more, more preferably 15 parts by mass or more. The upper limit is preferably 50 parts by mass or less, more preferably 40 parts by mass or less.
[0181] When the coloring composition of the present invention is used as a coloring composition for forming a red pixel of a color filter, it is preferable to use a yellow coloring agent and a red coloring agent in the coloring agent. And compound Y is preferably a yellow coloring agent. The mass ratio of the yellow coloring agent to the red coloring agent is preferably yellow coloring agent∶red coloring agent = 30∶70 to 70∶30, more preferably 30∶70 to 60∶40, and further preferably 30∶70 to 50∶50. And the content of compound Y is preferably 5 to 50 parts by mass with respect to 100 parts by mass of the red coloring agent. The lower limit is preferably 8 parts by mass or more, more preferably 10 parts by mass or more. The upper limit is preferably 40 parts by mass or less, more preferably 30 parts by mass or less.
[0182] When the coloring composition of the present invention is used as a coloring composition for forming a yellow pixel of a color filter, the content of the yellow coloring agent in the coloring agent is preferably 30% by mass or more, more preferably 40% by mass or more, and further preferably 50% by mass or more. And compound Y is preferably a yellow coloring agent. The content of compound Y in the yellow coloring agent is preferably 20% by mass or more, more preferably 25% by mass or more, and further preferably 30% by mass or more. The upper limit can also be set to 100% by mass, can also be set to 95% by mass or less, and can also be set to 90% by mass or less.
[0183] 《Resin》
[0184] The coloring composition of the present invention contains a resin. The resin is compounded, for example, for the purpose of dispersing pigments and the like in the coloring composition or as an adhesive. In addition, a resin mainly used for dispersing pigments and the like in the coloring composition is called a dispersant. However, this use of the resin is an example, and the resin can also be used for purposes other than this use.
[0185] The weight average molecular weight (Mw) of the resin is preferably 3000 to 2000000. The upper limit is preferably 1000000 or less, more preferably 500000 or less. The lower limit is preferably 4000 or more, more preferably 5000 or more.
[0186] Examples of the resin include (meth)acrylic resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polystyrene resins, polyaryletherphosphine oxide resins, polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, silicone resins, etc. Further, as the resin, the resins described in the examples of International Publication No. 2016 / 088645, the resins described in Japanese Patent Application Laid-Open No. 2017-057265, the resins described in Japanese Patent Application Laid-Open No. 2017-032685, the resins described in Japanese Patent Application Laid-Open No. 2017-075248, the resins described in Japanese Patent Application Laid-Open No. 2017-066240, the resins described in Japanese Patent Application Laid-Open No. 2017-167513, the resins described in Japanese Patent Application Laid-Open No. 2017-173787, the resins described in paragraphs 0041 to 0060 of Japanese Patent Application Laid-Open No. 2017-206689, the resins described in paragraphs 0022 to 0071 of Japanese Patent Application Laid-Open No. 2018-010856, the block polyisocyanate resin (cyanate resin) described in Japanese Patent Application Laid-Open No. 2016-222891, the resins described in Japanese Patent Application Laid-Open No. 2020-122052, the resins described in Japanese Patent Application Laid-Open No. 2020-111656, the resins described in Japanese Patent Application Laid-Open No. 2020-139021, and the resin described in Japanese Patent Application Laid-Open No. 2017-138503 which contains a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain can also be used.
[0187] As the resin, a resin having an acid group is preferably used. Examples of the acid group include a carboxyl group, a phosphoric acid group, a sulfonic acid group, a phenolic hydroxyl group, etc.
[0188] The acid value of the resin having an acid group is preferably 30 to 500 mgKOH / g. The lower limit is more preferably 40 mgKOH / g or more, particularly preferably 50 mgKOH / g or more. The upper limit is more preferably 400 mgKOH / g or less, further preferably 300 mgKOH / g or less, particularly preferably 200 mgKOH / g or less. The weight average molecular weight (Mw) of the resin having an acid group is preferably 5000 to 100000, more preferably 5000 to 50000. Further, the number average molecular weight (Mn) of the resin having an acid group is preferably 1000 to 20000.
[0189] The resin having an acid group preferably contains repeating units having an acid group in the side chain, and more preferably contains 5 to 70 mol% of repeating units having an acid group in the side chain among all the repeating units of the resin. The upper limit of the content of the repeating units having an acid group in the side chain is preferably 50 mol% or less, more preferably 30 mol% or less. The lower limit of the content of the repeating units having an acid group in the side chain is preferably 10 mol% or more, more preferably 20 mol% or more.
[0190] Regarding the resin having an acid group, reference can be made to the descriptions in paragraphs 0558 to 0571 of Japanese Unexamined Patent Application Publication No. 2012-208494 (corresponding to paragraphs 0685 to 0700 of the specification of International Patent Application Publication No. 2012 / 0235099), and paragraphs 0076 to 0099 of Japanese Unexamined Patent Application Publication No. 2012-198408. These contents are incorporated into this specification. Also, commercially available products can be used as the resin having an acid group. And, as a method for introducing an acid group into the resin, there is no particular limitation. For example, the method described in Japanese Patent No. 6349629 can be cited. In addition, as a method for introducing an acid group into the resin, a method of reacting an acid anhydride with a hydroxyl group generated in the ring-opening reaction of an epoxy group to introduce an acid group can also be cited.
[0191] The coloring composition of the present invention also preferably contains a resin having a basic group. The resin having a basic group preferably contains a resin having repeating units having a basic group in the side chain, more preferably a copolymer having repeating units having a basic group in the side chain and repeating units not containing a basic group, and further preferably a block copolymer having repeating units having a basic group in the side chain and repeating units 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.
[0192] Examples of commercially available products of 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 (manufactured by BYK Co., LTD.), SOLSPERSE 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (manufactured by Lubrizol Japan Limited.), Efka PX 4300, 4330, 4046, 4060, 4080 (manufactured by BASF Corporation), etc. Further, as the resin having a basic group, block copolymers (B) described in paragraphs 0063 to 0112 of Japanese Unexamined Patent Application Publication No. 2014-219665, block copolymer A1 described in paragraphs 0046 to 0076 of Japanese Unexamined Patent Application Publication No. 2018-156021, and vinyl resins having a basic group described in paragraphs 0150 to 0153 of Japanese Unexamined Patent Application Publication No. 2019-184763 can also be used, and these are incorporated herein by reference.
[0193] 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 mode, 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 with respect to 100 parts by mass of the resin having an acid group.
[0194] As the resin, a resin containing a repeating unit of a monomer component derived from a compound represented by the following formula (EDl) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may also be referred to as "ether dimers") is also preferably used.
[0195] [Chemical formula 10]
[0196]
[0197] In formula (ED1), R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
[0198] [Chemical formula 11]
[0199]
[0200] In formula (ED2), R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. For the details of formula (ED2), reference can be made to the description in Japanese Patent Application Laid-Open No. 2010-168539, and this content is incorporated into the present specification.
[0201] As a specific example of the ether dimer, for example, reference can be made to the description in paragraph 0317 of Japanese Patent Application Laid-Open No. 2013-029760, and this content is incorporated into the present specification.
[0202] As the resin, a resin containing a repeating unit derived from the compound represented by formula (X) is also preferably used.
[0203] [Chemical formula 12]
[0204]
[0205] In the formula, R 1 represents a hydrogen atom or a methyl group, R 21 and R 22 each independently represent an alkylene group, and n represents an integer of 0 to 15. The alkylene group represented by R 21 and R 22 preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, still more preferably 1 to 3 carbon atoms, and particularly preferably 2 or 3 carbon atoms. n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and still more preferably an integer of 0 to 3.
[0206] Examples of the compound represented by formula (X) include ethylene oxide or propylene oxide modified (meth)acrylate of p-cumylphenol. Examples of commercially available products include ARONIX M-110 (manufactured by TOAGOSEI CO., LTD.).
[0207] As the resin, a resin having a crosslinkable group is also preferably used. Examples of the crosslinkable group include a group containing an ethylenically unsaturated bond and a cyclic ether group.
[0208] Examples of the group containing an ethylenically unsaturated bond include a vinyl group, a styryl group, a (meth)allyl group, a (meth)acryloyl group, etc. Examples of the cyclic ether group include an epoxy group, an oxetanyl group, etc., and an epoxy group is preferred. The epoxy group may be an alicyclic epoxy group. In addition, the alicyclic epoxy group refers to a monovalent functional group having a cyclic structure formed by the fusion of an epoxy ring and a saturated hydrocarbon ring. The cyclic ether group is preferably at least one selected from the group represented by formula (e-1) and the group represented by formula (e-2), and more preferably the group represented by formula (e-2). When n in formula (e-1) is 0, the group represented by formula (e-1) is an epoxy group, and when n is 1, the group represented by formula (e-1) is an oxetanyl group. And, the group represented by formula (e-2) is an alicyclic epoxy group.
[0209] [Chemical formula 13]
[0210]
[0211] In formula (e-1), R E1 represents a hydrogen atom or an alkyl group, n represents 0 or 1, and * represents a bonding bond; in formula (e-2), ring A E1 represents an aliphatic hydrocarbon ring, and * represents a bonding bond.
[0212] R E1 The alkyl group represented preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, still more preferably 1 to 5 carbon atoms, and particularly preferably 1 to 3 carbon atoms. R E1 The alkyl group represented is preferably straight-chain or branched-chain, and more preferably straight-chain.
[0213] When n is 0, R E1 is preferably a hydrogen atom. When n is 1, R E1 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
[0214] Here, when n in formula (e-1) is 0, formula (e-1) is a group represented by the following formula (e-1a).
[0215] [Chemical formula 14]
[0216]
[0217] The aliphatic hydrocarbon ring represented by ring A in formula (e-2) E1 may be a monocyclic aliphatic hydrocarbon ring or a fused-ring aliphatic hydrocarbon ring. And, the aliphatic hydrocarbon ring represented by ring A E1 may have a crosslinked structure. Among them, from the reason of being easy to form a film with excellent moisture resistance, a fused-ring aliphatic hydrocarbon ring is preferred, and a fused-ring aliphatic hydrocarbon ring having a crosslinked structure is preferred. As ring A E1Specific examples of the aliphatic hydrocarbon ring represented include the groups shown below, preferably the group represented by formula (e-2-3) and the group represented by formula (e-2-4). In the following formulas, * represents a bonding bond.
[0218] [Chemical formula 15]
[0219]
[0220] As the resin having a cyclic ether group, a resin containing a repeating unit having a cyclic ether group is preferably used. As the repeating unit having a cyclic ether group, a repeating unit represented by formula (A1) can be cited.
[0221] [Chemical formula 16]
[0222]
[0223] In formula (A1), X a1 represents a trivalent linking group, L a1 represents a single bond or a divalent linking group, and Z a1 represents a cyclic ether group.
[0224] As the trivalent linking group represented by X in formula (A1) a1 examples include poly(meth)acrylic acid-based linking groups, polyalkyleneimine-based linking groups, polyester-based linking groups, polyurethane-based linking groups, polyurea-based linking groups, polyamide-based linking groups, polyether-based linking groups, polystyrene-based linking groups, bisphenol-based linking groups, novolak-based linking groups, etc. Preferred are poly(meth)acrylic acid-based linking groups, polyether-based linking groups, polyester-based linking groups, bisphenol-based linking groups, and novolak-based linking groups. More preferred are polyether-based linking groups, novolak-based linking groups, and poly(meth)acrylic acid-based linking groups. Further preferred is the poly(meth)acrylic acid-based linking group.
[0225] As the divalent linking group represented by L in formula (A1) a1 examples include alkylene (preferably alkylene having 1 to 12 carbon atoms), arylene (preferably arylene having 6 to 20 carbon atoms), -NH-, -SO-, -SO2-, -CO-, -O-, -COO-, -OCO-, -S-, and groups formed by combining two or more of these. The alkylene can be any of linear, branched, and cyclic, preferably linear or branched. Also, the alkylene may have a substituent or may be unsubstituted. Examples of the substituent include a hydroxyl group and an alkoxy group.
[0226] As the cyclic ether group represented by Z in formula (A1) a1 examples include an epoxy group and an oxetanyl group, preferably an epoxy group. And Z a1The cyclic ether group represented is preferably a group represented by formula (e-1) or a group represented by formula (e-2), more preferably a group represented by formula (e-2).
[0227] The content of the repeating unit having a cyclic ether group in the resin having a cyclic ether group is preferably 1 to 100 mol% in all the repeating units of the resin having a cyclic ether group. The upper limit is preferably 90 mol% or less, more preferably 80 mol% or less. The lower limit is preferably 2 mol% or more, more preferably 3 mol% or more.
[0228] The resin having a cyclic ether group may also have other repeating units in addition to the repeating unit having a cyclic ether group. Examples of other repeating units include a repeating unit having an acid group (hereinafter also referred to as repeating unit B-1), a repeating unit having a group in which the acid group is protected by a protecting group (hereinafter also referred to as repeating unit B-2), a repeating unit having an alkenyl unsaturated bond-containing group (hereinafter also referred to as repeating unit B-3), and the like.
[0229] Examples of the acid group in the repeating unit B-1 and the acid group protected by the protecting group in the repeating unit B-2 include a phenolic hydroxyl group, a carboxyl group, a sulfo group, and a phosphoric acid group. A phenolic hydroxyl group or a carboxyl group is preferred, and a carboxyl group is more preferred.
[0230] Examples of the protecting group for protecting the acid group in the repeating unit B-2 include a group that decomposes and detaches by the action of an acid or a base. The protecting group is preferably a group represented by any one of formulas (Y1) to (Y5), and more preferably a group represented by formula (Y3) or formula (Y5) for reasons of easy deprotection.
[0231] Formula (Y1): -C(R Y1 )(R Y2 )(R Y3 )
[0232] Formula (Y2): -C(=O)OC(R Y4 )(R Y5 )(R Y6 )
[0233] Formula (Y3): -C(R Y7 )(R Y8 )(OR Y9 )
[0234] Formula (Y4): -C(R Y10 )(H)(Ar Y1 )
[0235] Formula (Y5): -C(=0)(R Y11 )
[0236] In formula (Y1), RY1 ~R Y3 each independently represents an alkyl group, and two of R Y1 ~R Y3 can be bonded to form a ring;
[0237] In formula (Y2), R Y4 ~R Y6 each independently represents an alkyl group, and two of R Y4 ~R Y6 can be bonded to form a ring;
[0238] In formula (Y3), R Y7 and R Y8 each independently represents a hydrogen atom, an alkyl group or an aryl group, and at least one of R Y7 and R Y8 is an alkyl group or an aryl group, R Y9 represents an alkyl group or an aryl group, R Y7 or R Y8 and R Y9 can be bonded to form a ring;
[0239] In formula (Y4), Ar Y1 represents an aryl group, and R Y10 represents an alkyl group or an aryl group;
[0240] In formula (Y5), R Y11 represents an alkyl group or an aryl group.
[0241] The alkyl group represented by R Y1 ~R Y3 in formula (Y1) preferably has 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms. The alkyl group can be any of linear, branched and cyclic, and is preferably linear or branched. In formula (Y1), two of R Y1 ~R Y3 can be bonded to form a ring. Examples of the ring formed by the bonding of two of R Y1 ~R Y3 include monocyclic cycloalkyl groups such as cyclopentyl and cyclohexyl, and polycyclic cycloalkyl groups such as norbornyl, tetracyclodecyl, tetracyclododecyl and adamantyl. A monocyclic cycloalkyl group having 5 to 6 carbon atoms is preferred. Further, in the above cycloalkyl group, one methylene group constituting the ring may be substituted with a group having a heteroatom such as an oxygen atom or a heteroatom-containing group such as a carbonyl group.
[0242] The alkyl group represented by R Y4 ~R Y6 in formula (Y2) preferably has 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms. The alkyl group can be any of linear, branched and cyclic, and is preferably linear or branched. The R Y4 ~RY6 At least two of them are preferably methyl groups. In formula (Y2), R Y4 ~R Y6 Two of them can be bonded to form a ring. Examples of the formed ring include the rings described in formula (Y1).
[0243] In formula (Y3), R Y7 and R Y8 each independently represent a hydrogen atom, an alkyl group or an aryl group, at least one of R Y7 and R Y8 is an alkyl group or an aryl group, R Y9 represents an alkyl group or an aryl group, R Y7 or R Y8 and R Y9 can be bonded to form a ring.
[0244] The alkyl group can be linear, branched or cyclic. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 6, and further preferably 1 to 4. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12. Examples of the ring formed by the bonding of RY7 or R Y8 and R Y9 include tetrahydrofuranyl, tetrahydropyranyl, etc. In formula (Y3), it is preferred that R Y7 or R Y8 and R Y9 are bonded to form a ring. Moreover, it is preferred that one of R Y7 and R Y8 is a hydrogen atom.
[0245] In formula (Y4), Ar Y1 represents an aryl group, R Y10 represents an alkyl group or an aryl group, Ar Y1 and R Y10 can be bonded to each other to form a ring. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 6, and further preferably 1 to 4. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12. In formula (Y4), it is preferred that R Y10 is an alkyl group.
[0246] In formula (Y5), R Y11 represents an alkyl group or an aryl group, preferably an alkyl group. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 6, and further preferably 1 to 4. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12.
[0247] The molecular weight of the protecting group is preferably 40 to 200, more preferably 40 to 150, and further preferably 40 to 120. If the molecular weight of the protecting group is within the above range, a coloring composition with excellent storage stability and excellent curability at low temperature can be prepared.
[0248] As specific examples of the protecting group, 1-methoxyethyl, 1-ethoxyethyl, 1-n-propoxyethyl, 1-n-butoxyethyl, 1-tert-butoxyethyl, 1-cyclopentyloxyethyl, 1-cyclohexyloxyethyl, cyclohexyl(methoxy)methyl, α-methoxybenzyl, α-ethoxybenzyl, α-n-propoxybenzyl, 2-phenyl-1-methoxyethyl, 2-phenyl-1-ethoxyethyl, 2-phenyl-1-isopropoxyethyl, 2-tetrahydrofuranyl, 2-tetrahydropyranyl can be mentioned. Preferably, 1-ethoxyethyl, 1-cyclohexyloxyethyl, 2-tetrahydrofuranyl, 2-tetrahydropyranyl are used, and more preferably, 1-ethoxyethyl, 1-cyclohexyloxyethyl are used.
[0249] As the group having an ethylenically unsaturated bond in the repeating unit B-3, vinyl, styryl, (meth)allyl, (meth)acryloyl and the like can be mentioned.
[0250] As the repeating unit B-1, a repeating unit represented by the following formula (B1) can be mentioned. Further, as the repeating unit B-2, a repeating unit represented by the following formula (B2) can be mentioned. Further, as the repeating unit B-3, a repeating unit represented by the following formula (B3) can be mentioned.
[0251] [Chemical formula 17]
[0252]
[0253] In the formula (B1), X b1 represents a trivalent linking group, L b1 represents a single bond or a divalent linking group, and Z b1 represents an acid group.
[0254] In the formula (B2), X b2 represents a trivalent linking group, L b2 represents a single bond or a divalent linking group, and Z b2 represents a group in which the acid group is protected by a protecting group.
[0255] In the formula (B3), X b3 represents a trivalent linking group, L b3 represents a single bond or a divalent linking group, and Z b3 represents a group having an ethylenically unsaturated bond.
[0256] As the trivalent linking group represented by X in the formula (B1), the trivalent linking group represented by X in the formula (B2), and X in the formula (B3) b1 represented by, the trivalent linking group represented by X in the formula (B2), and X in the formula (B3) b2 represented by, and X in the formula (B3) b3The trivalent linking group represented is not particularly limited. For example, poly(meth)acrylic acid-based linking groups, polyalkyleneimine-based linking groups, polyester-based linking groups, polyurethane-based linking groups, polyurea-based linking groups, polyamide-based linking groups, polyether-based linking groups, polystyrene-based linking groups, bisphenol-based linking groups, novolak-based linking groups, etc. can be mentioned. Poly(meth)acrylic acid-based linking groups, polyether-based linking groups, polyester-based linking groups, bisphenol-based linking groups, and novolak-based linking groups are preferred, and poly(meth)acrylic acid-based linking groups are more preferred.
[0257] As the divalent linking group represented by L in formula (B1) b1 the divalent linking group represented by L in formula (B2), b2 the divalent linking group represented by L in formula (B3), b3 examples of the divalent linking group represented include alkylene groups (preferably alkylene groups having 1 to 12 carbon atoms), arylene groups (preferably arylene groups having 6 to 20 carbon atoms), -NH-, -SO-, -SO2-, -CO-, -O-, -COO-, -OCO-, -S-, and groups formed by combining two or more of these. The alkylene group can be any of linear, branched, and cyclic, and linear or branched is preferred. Also, the alkylene group may have a substituent or may be unsubstituted. Examples of the substituent include hydroxyl groups, alkoxy groups, etc.
[0258] As the acid group represented by Z in formula (B1) b1 examples of the acid group represented include phenolic hydroxyl groups, carboxyl groups, sulfo groups, phosphoric acid groups, phenolic hydroxyl groups or carboxyl groups are preferred, and carboxyl groups are more preferred.
[0259] As the group in which the acid group represented by Z in formula (B2) is protected by a protecting group b2 examples of the group in which the acid group represented by Z in formula (B2) is protected by a protecting group include groups in which the acid group is protected by a group represented by any one of the above formulas (Y1) to (Y5), and groups in which the acid group is protected by a group represented by formula (Y3) or formula (Y5) are preferred. Examples of the above acid group include phenolic hydroxyl groups, carboxyl groups, sulfo groups, phosphoric acid groups, phenolic hydroxyl groups or carboxyl groups are preferred, and carboxyl groups are more preferred.
[0260] As the group having an ethylenically unsaturated bond represented by Z in formula (B3) b3 examples of the group having an ethylenically unsaturated bond represented include vinyl groups, styryl groups, (meth)allyl groups, (meth)acryloyl groups, etc.
[0261] When the resin having a cyclic ether group contains the repeating unit B-1, the content of the unit B-1 in the resin having a cyclic ether group is preferably 5 to 85 mol% among all the repeating units of the resin having a cyclic ether group. The upper limit is preferably 60 mol% or less, more preferably 40 mol% or less. The lower limit is preferably 8 mol% or more, more preferably 10 mol% or more.
[0262] When the resin having a cyclic ether group contains the repeating unit B-2, the content of the unit B-2 in the resin having a cyclic ether group is preferably 1 to 65 mol% in all the repeating units of the resin having a cyclic ether group. The upper limit is preferably 45 mol% or less, more preferably 30 mol% or less. The lower limit is preferably 2 mol% or more, more preferably 3 mol% or more.
[0263] When the resin having a cyclic ether group contains the repeating unit B-1 and the repeating unit B-2, respectively, 1 mol of the repeating unit B-1 in the resin having a cyclic ether group preferably contains 0.4 to 3.2 mol of the repeating unit B-2, more preferably contains 0.8 to 2.8 mol, and further preferably contains 1.2 to 2.4 mol.
[0264] When the resin having a cyclic ether group contains the repeating unit B-3, the content of the unit B-3 in the resin having a cyclic ether group is preferably 1 to 65 mol% in all the repeating units of the resin having a cyclic ether group. The upper limit is preferably 45 mol% or less, more preferably 30 mol% or less. The lower limit is preferably 2 mol% or more, more preferably 3 mol% or more.
[0265] The resin having a cyclic ether group preferably further contains a repeating unit having an aromatic hydrocarbon ring. As the aromatic hydrocarbon ring, a benzene ring or a naphthalene ring is preferred, and a benzene ring is preferred. The aromatic hydrocarbon ring may have a substituent. Examples of the substituent include an alkyl group. When the resin having a cyclic ether group contains a repeating unit having an aromatic hydrocarbon ring, the content of the repeating unit having an aromatic hydrocarbon ring is preferably 1 to 65 mol% in all the repeating units of the resin having a cyclic ether group. The upper limit is preferably 45 mol% or less, more preferably 30 mol% or less. The lower limit is preferably 2 mol% or more, more preferably 3 mol% or more. Examples of the repeating unit having an aromatic hydrocarbon ring include repeating units derived from monofunctional polymerizable compounds having an aromatic hydrocarbon ring such as vinyltoluene and (meth)acrylic acid benzyl ester.
[0266] As commercially available products of resins having a cyclic ether group, for example, as naphthalene-modified epoxy resins, EPICLON HP5000, EPICLON HP4032D (both manufactured by DIC CORPORATION) and the like can be cited. As alkyl bisphenol type epoxy resins, EPICLON 820 (manufactured by DIC CORPORATION) and the like can be cited. As bisphenol A type epoxy resins, jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, jER1010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON860, EPICLON1050, EPICLON1051, EPICLON1055 (all manufactured by DIC CORPORATION) and the like can be cited. As bisphenol F type epoxy resins, jER806, jER807, jER4004, jER4005, jER4007, jER4010 (all manufactured by Mitsubishi Chemical Corporation), EPICLON830, EPICLON835 (all manufactured by DIC CORPORATION), LCE-21, RE-602S (all manufactured by Nippon Kayaku Co., Ltd.) and the like can be cited. As phenol novolac type epoxy resins, jER152, jER154, jER157S70, jER157S65 (all manufactured by Mitsubishi Chemical Corporation), EPICLON N-740, EPICLON N-770, EPICLON N-775 (all manufactured by DIC CORPORATION) and the like can be cited. As cresol novolac type epoxy resins, EPICLON N-660, EPICLON N-665, EPICLON N-670, EPICLON N-673, EPICLON N-680, EPICLON N-690, EPICLON N-695 (all manufactured by DIC CORPORATION), EOCN-1020 (manufactured by Nippon Kayaku Co., Ltd.) and the like can be cited.As the aliphatic epoxy resin, examples include ADEKA RESIN EP-4080S, ADEKARESIN EP-4085S, ADEKA RESIN EP-4088S (the above are manufactured by ADEKA Corporation), CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CELLOXIDE 2085, EHPE3150, EPOLEAD PB 3600, EPOLEAD PB 4700 (the above are manufactured by Daicel Corporation), DENACOL EX-212L, EX-214L, EX-216L, EX-321L, EX-850L (the above are manufactured by Nagase ChemteX Corporation), etc. Further, as the resin having a cyclic ether group, the resins described in paragraphs 0034 to 0036 of Japanese Unexamined Patent Application Publication No. 2013-011869, the resins described in paragraphs 0147 to 0156 of Japanese Unexamined Patent Application Publication No. 2014-043556, the resins described in paragraphs 0085 to 0092 of Japanese Unexamined Patent Application Publication No. 2014-089408, the resins described in Japanese Unexamined Patent Application Publication No. 2017-179172, the resins described in paragraphs 0027 to 0055 and 0096 of Japanese Unexamined Patent Application Publication No. 2018-180081, the resins described in paragraphs 0117 to 0120 of Japanese Patent Application Laid-Open No. 2020-515680, and the resins described in paragraph 0084 of International Publication No. 2020 / 175011 can also be used.
[0267] As the resin, a resin having an aromatic carboxyl group (hereinafter, also referred to as resin Ac) is also preferably used. In resin Ac, the aromatic carboxyl group may be contained in the main chain of the repeating unit or in the side chain of the repeating unit. The aromatic carboxyl group is preferably contained in the main chain of the repeating unit. In addition, in the present 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. In the aromatic carboxyl group, the number of carboxyl groups bonded to the aromatic ring is preferably 1 to 4, more preferably 1 to 2.
[0268] Resin Ac is preferably a resin containing at least one repeating unit selected from the repeating unit represented by formula (Ac-1) and the repeating unit represented by formula (Ac-2).
[0269] [Chemical formula 18]
[0270]
[0271] In formula (Ac-1), Ar 1 represents a group containing an aromatic carboxyl group, and L 1represents -COO- or -CONH-, L 2 represents a divalent linking group.
[0272] In formula (Ac-2), Ar 10 represents a group containing an aromatic carboxyl group, L 11 represents -COO- or -CONH-, L 12 represents a trivalent linking group, P 10 represents a polymer chain.
[0273] As the group containing an aromatic carboxyl group represented by Ar in formula (Ac-1) 1 structures derived from aromatic tricarboxylic anhydrides, structures derived from aromatic tetracarboxylic anhydrides, etc. may be mentioned. As the aromatic tricarboxylic anhydrides and aromatic tetracarboxylic anhydrides, compounds having the following structures may be mentioned.
[0274] [Chemical formula 19]
[0275]
[0276] In the above formula, Q 1 represents a single bond, -O-, -CO-, -COOCH2CH2OCO-, -SO2-, -C(CF3)2-, a group represented by the following formula (Q-1) or a group represented by the following formula (Q-2).
[0277] [Chemical formula 20]
[0278]
[0279] Ar 1 The group containing an aromatic carboxyl group represented by it may have a crosslinkable group. The crosslinkable group is preferably an alkenyl unsaturated bond-containing group and a cyclic ether group, and more preferably an alkenyl unsaturated bond-containing group. As Ar 1 specific examples of the group containing an aromatic carboxyl group represented by it, groups represented by formula (Ar-11), groups represented by formula (Ar-12), groups represented by formula (Ar-13), etc. may be mentioned.
[0280] [Chemical formula 21]
[0281]
[0282] In formula (Ar-11), n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
[0283] In 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.
[0284] 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 still more preferably 1. Among them, at least one of n3 and n4 is an integer of 1 or more.
[0285] In formula (Ar-13), Q 1 represents a single bond, -O-, -CO-, -COOCH2CH2OCO-, -SO2-, -C(CF3)2-, a group represented by the above formula (Q-1), or a group represented by the above formula (Q-2).
[0286] In formulas (Ar-11) to (Ar-13), *1 represents the bonding position to L 1
[0287] In formula (Ac-1), L 1 represents -COO- or -CONH-, preferably represents -COO-.
[0288] As the divalent linking group represented by L in formula (Ac-1) 2 examples include an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and a group formed by combining two or more of these. The number of carbon atoms of the alkylene group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The alkylene group can be any of linear, branched, and cyclic. The number of carbon atoms of the arylene group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 10. The alkylene group and the arylene group may have substituents. Examples of the substituent include a hydroxyl group. The divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-. L 2a Examples include an alkylene group; an arylene group; a group formed by combining an alkylene group and an arylene group; a group formed by combining at least one selected from an alkylene group and an arylene group with at least one selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-, and is preferably an alkylene group. The number of carbon atoms of the alkylene group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The alkylene group can be any of linear, branched, and cyclic. The alkylene group and the arylene group may have substituents. Examples of the substituent include a hydroxyl group.
[0289] As the group containing an aromatic carboxyl group represented by Ar in formula (Ac-2) 10 it has the same meaning as Ar in formula (Ac-1), and the preferred range is also the same. 1
[0290] In formula (Ac-2), L 11 represents -COO- or -CONH-, and preferably represents -COO-.
[0291] As the trivalent linking group represented by L in formula (Ac-2) 12 Examples of the trivalent linking group include a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and a group formed by combining two or more of these. Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The aliphatic hydrocarbon group can be linear, branched, or cyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include a hydroxyl group, etc. L 12 The trivalent linking group represented by L is preferably a group represented by formula (L12-1), and more preferably a group represented by formula (L12-2).
[0292] [Chemical formula 22]
[0293]
[0294] In formula (L12-1), L 12b represents a trivalent linking group, X 1 represents S, *1 represents the bonding position with L of formula (Ac-2) 11 and *2 represents the bonding position with P of formula (Ac-2) 10 Examples of the trivalent linking group represented by L 12b include a hydrocarbon group; a group formed by combining a hydrocarbon group with at least one selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-, etc. Preferably, it is a hydrocarbon group or a group formed by combining a hydrocarbon group with -O-.
[0295] In formula (L12-2), L 12c represents a trivalent linking group, X 1 represents S, *1 represents the bonding position with L of formula (Ac-2) 11 and *2 represents the bonding position with P of formula (Ac-2) 10 Examples of the trivalent linking group represented by L 12c include a hydrocarbon group; a group formed by combining a hydrocarbon group with at least one selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-, etc. Preferably, it is a hydrocarbon group.
[0296] In formula (Ac-2), P 10 represents a polymer chain. P 10 The polymer chain represented preferably has at least one repeating unit selected from poly(meth)acrylic acid repeating units, polyether repeating units, polyester repeating units, and polyol repeating units. The polymer chain P 10The weight-average molecular weight 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. If P 10 The weight-average molecular weight is within the above range, the dispersibility of the pigment in the composition is good. When the resin having an aromatic carboxyl group is a resin having a repeating unit represented by the formula (Ac-2), the resin can preferably be used as a dispersant.
[0297] P 10 The polymer chain represented by may include a crosslinkable group. Examples of the crosslinkable group include an alkenyl unsaturated bond-containing group and a cyclic ether group.
[0298] The coloring composition of the present invention preferably contains a resin as a dispersant. Examples of the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin). Here, the acidic dispersant (acidic resin) means a resin in which the amount of acid groups is larger than the amount of basic groups. As the acidic dispersant (acidic resin), when the total amount of the amount of acid groups and the amount of basic groups is set to 100 mol%, a resin in which the amount of acid groups is preferably 70 mol% or more is preferred. The acid group of the acidic dispersant (acidic resin) is preferably a carboxyl group. The acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH / g. And, the basic dispersant (basic resin) means a resin in which the amount of basic groups is larger than the amount of acid groups. As the basic dispersant (basic resin), a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the amount of acid groups and the amount of basic groups is set to 100 mol% is preferred. The basic group of the basic dispersant is preferably an amino group.
[0299] The resin used as a dispersant is also preferably a graft resin. For the details of the graft resin, reference can be made to the description in paragraphs 0025 to 0094 of Japanese Patent Application Laid-Open No. 2012-255128, and this content is incorporated into the present specification.
[0300] The resin used as a dispersant is also preferably a polyimine-based dispersant containing a nitrogen atom at at least one of the main chain and the side chain. As the polyimine-based dispersant, a resin having a main chain and a side chain and having a basic nitrogen atom at at least one of the main chain and the side chain is preferred. The main chain includes a partial structure having a functional group with a pKa of 14 or less, and the side chain has 40 to 10,000 atoms. The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom having basicity. For the polyimine-based dispersant, reference can be made to the description in paragraphs 0102 to 0166 of Japanese Patent Application Laid-Open No. 2012-255128, and this content is incorporated into the present specification.
[0301] The resin used as a dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core. As such a resin, for example, dendritic polymers (including star polymers) can be mentioned. And, as specific examples of the dendritic polymer, the high molecular compounds C-1 to C-31 described in paragraphs 0196 to 0209 of Japanese Unexamined Patent Application Publication No. 2013-043962 can be mentioned, etc.
[0302] The resin used as a dispersant is also preferably a resin containing a repeating unit having a group containing an ethylenically unsaturated bond in the side chain. The content of the repeating unit having a group containing an ethylenically unsaturated bond in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and still more preferably 20 to 70 mol% among all the repeating units of the resin.
[0303] Also, as the dispersant, the resins described in Japanese Unexamined Patent Application Publication No. 2018-087939, the block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077, the polyethyleneimine having a polyester side chain described in International Publication No. 2016 / 104803, the block copolymer described in International Publication No. 2019 / 125940, the block polymer having an acrylamide structural unit described in Japanese Unexamined Patent Application Publication No. 2020-066687, the block polymer having an acrylamide structural unit described in Japanese Unexamined Patent Application Publication No. 2020-066688, the dispersant described in International Publication No. 2016 / 104803, etc. can be used.
[0304] The dispersant can also be obtained as a commercial product. As such specific examples, the Disperbyk series manufactured by BYK Co., LTD (for example, Disperbyk-111, 161, 2001, etc.), the SOLSPERSE series manufactured by Lubrizol Japan Limited. (for example, SOLSPERSE 20000, 76500, etc.), the AJISPER series manufactured by Ajinomoto Fine-Techno Co., Inc., etc. can be mentioned. Also, the products described in paragraph 0129 of Japanese Unexamined Patent Application Publication No. 2012-137564 and the products described in paragraph 0235 of Japanese Unexamined Patent Application Publication No. 2017-194662 can be used as the dispersant.
[0305] The content of the resin in the total solid components of the coloring composition is preferably 1 to 50% by mass. The upper limit is preferably 40% by mass or less, more preferably 30% by mass or less. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more. The coloring composition of the present invention may contain only one kind of resin, or may contain two or more kinds. In the case of containing two or more kinds of resins, it is preferable that their total is within the above range.
[0306] "Polymerizable Compound"
[0307] The coloring composition of the present invention preferably contains a polymerizable compound. Examples of the polymerizable compound include compounds having a group containing an ethylenically unsaturated bond. Examples of the group containing an ethylenically unsaturated bond include vinyl, (meth)allyl, (meth)acryloyl, etc. The polymerizable compound used in the present invention is preferably a free-radical polymerizable compound.
[0308] The polymerizable compound can be in any chemical form such as a monomer, prepolymer, oligomer, etc., but a monomer is preferred. The molecular weight of the polymerizable compound is preferably 100 to 3000. The upper limit is preferably 2000 or less, more preferably 1500 or less. The lower limit is preferably 150 or more, more preferably 250 or more.
[0309] From the viewpoint of the temporal stability of the coloring composition, the value of the group containing an ethylenically unsaturated bond (hereinafter referred to as the C═C value) of the polymerizable compound is preferably 2 to 14 mmol / g. The lower limit is preferably 3 mmol / g or more, more preferably 4 mmol / g or more, and further preferably 5 mmol / g or more. The upper limit is preferably 12 mmol / g or less, more preferably 10 mmol / g or less, and further preferably 8 mmol / g or less. The C═C value of the polymerizable compound is a value calculated by dividing the number of groups containing an ethylenically unsaturated bond contained in one molecule of the polymerizable compound by the molecular weight of the polymerizable compound.
[0310] The polymerizable compound is preferably a compound containing 3 or more groups containing an ethylenically unsaturated bond, more preferably a compound containing 4 or more groups containing an ethylenically unsaturated bond. From the viewpoint of the temporal stability of the coloring composition, the upper limit of the group containing an ethylenically unsaturated bond is preferably 15 or less, more preferably 10 or less, and further preferably 6 or less. Also, the polymerizable compound is preferably a (meth)acrylate compound having 3 or more functional groups, more preferably a (meth)acrylate compound having 3 to 15 functional groups, further preferably a (meth)acrylate compound having 3 to 10 functional groups, and particularly preferably a (meth)acrylate compound having 3 to 6 functional groups.
[0311] Examples of the polymerizable compound include dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and modified products of these compounds. Examples of the modified product include ethoxylated dipentaerythritol hexa(meth)acrylate, compounds having a structure in which the (meth)acryloyl group of the above compounds is bonded via an alkylene oxide, etc. Specific examples include the compound represented by formula (Z-4), the compound represented by formula (Z-5), etc.
[0312] [Chemical formula 23]
[0313]
[0314] In formulas (Z-4) and (Z-5), E each independently represents -((CH2) y CH2O)- or -((CH2) y CH(CH3)O)-, y each independently represents an integer from 0 to 10, and X each independently represents a (meth)acryloyl group, a hydrogen atom, or a carboxyl group. In formula (Z-4), the total number of (meth)acryloyl groups is 3 or 4, m each independently represents an integer from 0 to 10, and the total of each m is an integer from 0 to 40. In formula (Z-5), the total number of (meth)acryloyl groups is 5 or 6, n each independently represents an integer from 0 to 10, and the total of each n is an integer from 0 to 60.
[0315] In formula (Z-4), m is preferably an integer from 0 to 6, more preferably an integer from 0 to 4. Also, the total of each m is preferably an integer from 2 to 40, more preferably an integer from 2 to 16, and particularly preferably an integer from 4 to 8.
[0316] In formula (Z-5), n is preferably an integer from 0 to 6, more preferably an integer from 0 to 4. Also, the total of each n is preferably an integer from 3 to 60, more preferably an integer from 3 to 24, and particularly preferably an integer from 6 to 12.
[0317] Also, preferably, E in formula (Z-4) or formula (Z-5), that is, -((CH2) y CH2O)- or -((CH2) y CH(CH3)O)- is in a form where the end on the oxygen atom side is bonded to X.
[0318] Also, as the polymerizable compound, a pentaerythritol poly(meth)acrylate represented by the following formula (Z-6) can also be used.
[0319] [Chemical formula 24]
[0320]
[0321] In formula (Z-6), X 1 ~X 6 each independently represents a hydrogen atom or a (meth)acryloyl group, and n represents an integer from 1 to 10. Here, at least one of X 1 ~X 6 is a (meth)acryloyl group.
[0322] The polymerizable compound used in the present invention is preferably at least one selected from dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, poly(pentaerythritol) poly(meth)acrylate, and modified products thereof. Examples of commercially available products include KAYARAD D-310, DPHA, DPEA-12 (manufactured by Nippon Kayaku Co., Ltd.), NKESTER A-DPH-12E, TPOA-50 (manufactured by Shin-Nakamura Chemical Co., Ltd.), and the like.
[0323] Moreover, as the polymerizable compound, diglycerol EO (ethylene oxide) modified (meth)acrylate (commercially available product: M-460; manufactured by TOAGOSEI CO., LTD.), pentaerythritol tetra(meth)acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK ESTER A-TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), ARONIX TO-2349 (manufactured by TOAGOSEI CO., LTD.), NK OLIGO UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by TAISEI FINE CHEMICAL CO,., LTD.), LIGHT ACRYLATE POB-A0 (manufactured by KYOEISHA CHEMICAL CO., LTD.), EBECRYL80 (manufactured by DAICEL-ALLNEX LTD., amine-containing tetrafunctional acrylate), and the like can also be used.
[0324] Also, as the polymerizable compound, it is also preferable to use 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. Examples of commercially available trifunctional (meth)acrylate compounds include ARONIX M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305, M-303, M-452, M-450 (manufactured by TOAGOSEI CO., LTD.), NK ESTER A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A-TMM-3LM-N, A-TMPT, TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.), etc.
[0325] Also, as the polymerizable compound, it is also possible to use compounds having acid groups such as carboxyl group, sulfo group, and phosphoric acid group. Examples of commercially available products of such compounds include ARONIX M-305, M-510, M-520, ARONIX TO-2349 (manufactured by TOAGOSEI CO., LTD.), etc.
[0326] Also, as the polymerizable compound, it is also possible to use compounds having a caprolactone structure. Regarding the compounds having a caprolactone structure, reference can also be made to the descriptions in paragraphs 0042 to 0045 of Japanese Patent Application Laid-Open No. 2013-253224, and this content is incorporated herein. Examples of the compounds having a caprolactone structure include DPCA-20, DPCA-30, DPCA-60, DPCA-120, etc., which are commercially available from Nippon Kayaku Co., Ltd. as the KAYARAD DPCA series.
[0327] Also, as the polymerizable compound, it is also possible to use polymerizable compounds having a fluorene skeleton. Examples of commercially available products include OGSOL EA-0200, EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fluorene skeleton), etc.
[0328] Further, as the polymerizable compound, a compound substantially free of environmentally regulated substances such as toluene is also preferably used. Commercially available products of such compounds include KAYARAD DPHA LT, KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.), and the like.
[0329] Further, as the polymerizable compound, polyurethane acrylates described in Japanese Patent Publication No. Sho 48-041708, Japanese Unexamined Patent Publication No. Sho 51-037193, Japanese Examined Patent Publication No. Hei 02-032293, Japanese Examined Patent Publication No. Hei 02-016765, or urethane compounds having an ethylene oxide-based skeleton described in Japanese Patent Publication No. Sho 58-049860, Japanese Patent Publication No. Sho 56-017654, Japanese Patent Publication No. Hei 62-039417, Japanese Patent Publication No. Hei 62-039418 are also preferably used. Further, polymerizable compounds having an amino structure or a thioether structure in the molecule described in Japanese Unexamined Patent Publication No. Sho 63-277653, Japanese Unexamined Patent Publication No. Sho 63-260909, Japanese Unexamined Patent Publication No. Hei 01-105238 are also preferably used. Commercially available products such as UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by KYOEISHA CHEMICAL CO., LTD.) can also be used as the polymerizable compound.
[0330] The content of the polymerizable compound in the total solid content of the coloring composition is preferably 1 to 35% by mass. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less. The lower limit is preferably 2% by mass or more, more preferably 5% by mass or more. The coloring composition of the present invention may contain only one kind of polymerizable compound or two or more kinds. When two or more kinds of polymerizable compounds are contained, the total amount thereof is preferably within the above range.
[0331] <Photopolymerization initiator>
[0332] The coloring composition of the present invention can contain a photopolymerization initiator. When the coloring composition of the present invention contains a polymerizable compound, it is preferable that the coloring composition of the present invention further contains a photopolymerization initiator. The photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light in the ultraviolet region to the visible region is preferably used. The photopolymerization initiator is preferably a photo radical polymerization initiator.
[0333] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, α-hydroxy ketone compounds, α-amino ketone compounds, etc. From the viewpoint of exposure sensitivity, the photopolymerization initiator is preferably a trihalomethyl triazine compound, a benzyldimethyl ketal compound, an α-hydroxy ketone compound, an α-amino ketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a hexaarylbiimidazole compound, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyl oxadiazole compound, and a 3-aryl-substituted coumarin compound, more preferably a compound selected from oxime compounds, α-hydroxy ketone compounds, α-amino ketone compounds, and acylphosphine compounds, and still more preferably an oxime compound. Further, examples of the photopolymerization initiator include the compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173, the compounds described in JP-B-6301489, the peroxide-based photopolymerization initiators described in MATERIAL STAGE37 to 60p, vol.19, No.3, 2019, the photopolymerization initiators described in WO2018 / 221177, the photopolymerization initiators described in WO2018 / 110179, the photopolymerization initiators described in JP-A-2019-043864, the photopolymerization initiators described in JP-A-2019-044030, the peroxide-based initiators described in JP-A-2019-167313, the oxazolidinyl-substituted aminophenone-based initiators described in JP-A-2020-055992, the oxime-based photopolymerization initiators described in JP-A-2013-190459, the polymers described in JP-A-2020-172619, etc., and these are incorporated herein by reference.
[0334] Specific examples of the hexaarylbiimidazole compound include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole, etc.
[0335] Examples of commercially available α-hydroxy ketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V. as above), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (manufactured by BASF as above), and the like. Examples of commercially available α-amino ketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V. as above), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by BASF as above), and the like. Examples of commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V. as above), Irgacure 819, Irgacure TPO (manufactured by BASF as above), and the like.
[0336] As the oxime compound, examples include the compounds described in JP-A-2001-233842, the compounds described in JP-A-2000-080068, the compounds described in JP-A-2006-342166, the compounds described in J.C.S. Perkin II (1979, pp. 1653-1660), the compounds described in J.C.S. Perkin II (1979, pp. 156-162), the compounds described in Journal of Photopolymer Science and Technology (1995, pp. 202-232), the compounds described in JP-A-2000-066385, the compounds described in JP-T-2004-534797, the compounds described in JP-A-2006-342166, the compounds described in JP-A-2017-019766, the compounds described in JP No. 6065596, the compounds described in WO 2015 / 152153, the compounds described in WO 2017 / 051680, the compounds described in JP-A-2017-198865, the compounds described in paragraphs 0025 to 0038 of WO 2017 / 164127, the compounds described in WO 2013 / 167515, and the like. Specific examples of the oxime compound include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyimino-pentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyl oxime), and the like. As commercially available products, examples include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04 (manufactured by BASF), TR-PBG-304, TR-PBG-327 (manufactured by TRONLY), ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation, photoinitiator 2 described in JP-A-2012-014052). Further, as the oxime compound, a compound having no coloring property or a compound having high transparency and being less likely to change color is also preferably used.As commercially available products, examples include ADEKA ARKLS NCI-730, NCI-831, NCI-930 (the above are manufactured by ADEKA CORPORATION), etc.
[0337] As the photopolymerization initiator, an oxime compound having a fluorene ring can also be used. Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466, the compounds described in Japanese Patent No. 6636081, and the compounds described in Korean Laid-Open Patent No. 10-2016-0109444.
[0338] As the photopolymerization initiator, an oxime compound in which at least one benzene ring in the carbazole ring is a naphthalene ring skeleton can also be used. Specific examples of such an oxime compound include the compounds described in WO2013 / 083505.
[0339] As the photopolymerization initiator, an oxime compound having a fluorine atom can also be used. Specific examples of the oxime compound having a fluorine atom include the compounds described in JP-A-2010-262028, the compounds described in JP-T-2014-500852 (24, 36 to 40), and the compound (C-3) described in JP-A-2013-164471.
[0340] 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. Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP-A-2013-114249, paragraphs 0008 to 0012 and 0070 to 0079 of JP-A-2014-137466, the compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, and ADEKA ARKLS NCI-831 (manufactured by ADEKA CORPORATION).
[0341] As the photopolymerization initiator, an oxime compound having a benzofuran skeleton can also be used. Specific examples include OE-01 to OE-75 described in WO2015 / 036910.
[0342] As the photopolymerization initiator, an oxime compound in which a substituent having a hydroxyl group is bonded to the carbazole skeleton can also be used. Examples of such a photopolymerization initiator include the compounds described in WO2019 / 088055.
[0343] As the photopolymerization initiator, an aromatic ring group Ar formed by introducing an electron-withdrawing group into the aromatic ring can also be used.OX1 oxime compound (hereinafter also referred to as oxime compound OX). As the above aryl group Ar OX1 Examples of the electron-withdrawing group include an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a cyano group. The acyl group and the nitro group are preferably, considering the reason for easily forming a film with excellent light resistance, more preferably an acyl group, and further preferably a benzoyl group. The benzoyl group may have a substituent. As the substituent, a halogen atom, a cyano group, a nitro group, a hydroxyl group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkenyl group, an alkylthio group, an arylthio group, an acyl group, or an amino group is preferred, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic oxy group, an alkylthio group, an arylthio group, or an amino group is more preferred, and an alkoxy group, an alkylthio group, or an amino group is further preferred.
[0344] The oxime compound OX is preferably at least one selected from the compounds represented by formula (OX1) and the compounds represented by formula (OX2), and more preferably the compounds represented by formula (OX2).
[0345] [Chemical formula 25]
[0346]
[0347] 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 heterocyclic oxy group, an alkylthio group, an arylthio 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,
[0348] R X2 represents an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkylthio group, an arylthio group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyloxy group, or an amino group,
[0349] R X3 ~R X14 each independently represents a hydrogen atom or a substituent;
[0350] Among them, at least one of R X10 ~R X14 is an electron-withdrawing group.
[0351] Examples of the electron-withdrawing group include an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a cyano group. The acyl group and the nitro group are preferred, and considering the reason for easily forming a film with excellent light resistance, the acyl group is more preferred, and the benzoyl group is further preferred.
[0352] In the above formula, R X12is an electron-withdrawing group, R X10 , R X11 , R X13 , R X14 is preferably a hydrogen atom.
[0353] As a specific example of the oxime compound OX, the compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600 can be cited.
[0354] Specific examples of the oxime compound preferably used in the present invention are shown below, but the present invention is not limited to these.
[0355] [Chemical formula 26]
[0356]
[0357] [Chemical formula 27]
[0358]
[0359] [Chemical formula 28]
[0360]
[0361] The oxime compound is preferably a compound having a maximum absorption wavelength in the range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in the range of 360 to 480 nm. Further, from the viewpoint of sensitivity, it is preferred that the oxime compound has a high molar extinction coefficient at a wavelength of 365 nm or 405 nm, more preferably 1000 to 300000, still more preferably 2000 to 300000, and particularly preferably 5000 to 200000. The molar extinction coefficient of the compound can be measured by a known method. For example, it is preferably measured at a concentration of 0.01 g / L using ethyl acetate solvent by a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
[0362] As the photopolymerization initiator, it is also preferred to use a combination of Irgacure OXE01 (manufactured by BASF) and / or Irgacure OXE02 (manufactured by BASF) and Omnirad 2959 (manufactured by IGM Resins B.V.).
[0363] As the photopolymerization initiator, a bifunctional or higher trifunctional photoradical polymerization initiator can be used. By using such a photoradical polymerization initiator, two or more radicals are generated from one molecule of the photoradical polymerization initiator, and thus good sensitivity can be obtained. Further, in the case of using a compound having an asymmetric structure, the crystallinity decreases and the solubility in a solvent or the like is improved, and it becomes difficult to precipitate with time, thereby enabling the improvement of the temporal stability of the coloring composition. Specific examples of the bifunctional or higher trifunctional photoradical polymerization initiator include the dimer of the oxime compound described in paragraphs 0407 to 0412 of Japanese Patent Application Laid-Open No. 2010-527339, Japanese Patent Application Laid-Open No. 2011-524436, International Publication No. 2015 / 004565, paragraphs 0407 to 0412 of Japanese Patent Application Laid-Open No. 2016-532675, the dimer of the oxime compound described in paragraphs 0039 to 0055 of International Publication No. 2017 / 033680, compound (E) and compound (G) described in Japanese Patent Application Laid-Open No. 2013-522445, Cmpd1 to 7 described in International Publication No. 2016 / 034963, the oxime ester-based photoinitiator described in paragraph 0007 of Japanese Patent Application Laid-Open No. 2017-523465, the photoinitiator described in paragraphs 0020 to 0033 of Japanese Patent Application Laid-Open No. 2017-167399, the photopolymerization initiator (A) described in paragraphs 0017 to 0026 of Japanese Patent Application Laid-Open No. 2017-151342, the oxime ester photoinitiator described in Japanese Patent No. 6469669, and the like.
[0364] The content of the photopolymerization 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, more preferably 1% by mass or more. The upper limit is preferably 20% by mass or less, more preferably 15% by mass or less. In the coloring composition of the present invention, only one kind of photopolymerization initiator may be used, or two or more kinds may be used. In the case of using two or more kinds, it is preferable that their total is within the above range.
[0365] 《Solvent》
[0366] The coloring composition of the present invention preferably contains a solvent. Examples of the solvent include organic solvents. The type of the solvent is not particularly limited as long as it satisfies the solubility of each component or the coatability of the composition. Examples of the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents, etc. For the details of these, reference can be made to paragraph 0223 of International Publication No. 2015 / 166779, and the content is incorporated into this specification. Also, ester solvents substituted with a cyclic alkyl group and ketone solvents substituted with a cyclic alkyl group can be preferably used. Specific examples of the organic solvent include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, 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, methyl ethyl ketone, γ-butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, 1,3-diacetoxybutane, dipropylene glycol methyl ether acetate, diacetone alcohol (also known as diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, isopropyl alcohol, etc. However, sometimes for environmental reasons, etc., aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents are preferably reduced (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).
[0367] In the present invention, an organic solvent with a low metal content is preferably used. The metal content of the organic solvent is preferably 10 mass ppb (parts per billion) or less, for example. If necessary, an organic solvent at the mass ppt (parts per trillion) level can be used, and such an organic solvent is provided by Toyo Gosei Co., Ltd. (Chemical Industry Daily, November 13, 2015), for example.
[0368] As a method for removing impurities such as metals from an organic solvent, distillation (such as molecular distillation or thin-film distillation) or filtration using a filter can be cited, for example. The pore diameter of the filter used in filtration is preferably 10 μm or less, more preferably 5 μm or less, and further preferably 3 μm or less. The filter material is preferably polytetrafluoroethylene, polyethylene, or nylon.
[0369] The organic solvent may contain isomers (compounds having the same number of atoms but different structures). Also, the isomers may contain only one kind or may contain a plurality of kinds.
[0370] The content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
[0371] The content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and further preferably 30 to 90% by mass.
[0372] Furthermore, from the perspective of environmental regulation, it is preferred that the coloring composition of the present invention does not substantially contain environmentally regulated substances. In addition, in the present invention, substantially containing no 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 1 is particularly preferably less than mass ppm. 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 under REACH (Registration Evaluation Authorization and Restriction of CHemicals) control, PRTR (Pollutant Release and Transfer Register) method, VOC (Volatile Organic Compounds) control, 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 they 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, the method of heating and reducing the system interior to be set to above the boiling point of the environmentally controlled substances, and distilling and removing the environmentally controlled substances from the system interior and reducing them can be cited. In addition, in the case of distilling and removing a small amount of environmentally controlled substances, it is also useful to azeotropize with a solvent having the same boiling point as the solvent in order to improve efficiency. In addition, in the case of containing a compound with free radical polymerizability, it can be removed by distillation under reduced pressure after adding an inhibitor, so as to suppress the free radical polymerization reaction in the distillation under reduced pressure and cause crosslinking between molecules. These distillation removal methods can be carried out in any stage of the raw material stage, the stage of the product (such as the resin solution and the multifunctional monomer solution after polymerization) of the raw material reaction, or the stage of the coloring composition made by mixing these compounds.
[0373] 《Infrared absorber》
[0374] The coloring composition of the present invention may also 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 2The ratio of A is preferably 1 / A 2 0.08 or less, more preferably 0.04 or less.
[0375] Examples of the infrared absorber include pyrrolopyrrole compounds, cyanine compounds, squaric acid compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, anthocyanin compounds, xanthenium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, methylene azo compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, etc. Examples of the pyrrolopyrrole compounds include the compounds described in paragraphs 0016 to 0058 of JP-A-2009-263614, the compounds described in paragraphs 0037 to 0052 of JP-A-2011-068731, the compounds described in paragraphs 0010 to 0033 of WO 2015 / 166873, etc. Examples of the squaric acid compounds include the compounds described in paragraphs 0044 to 0049 of JP-A-2011-208101, the compounds described in paragraphs 0060 to 0061 of JP No. 6065169, the compounds described in paragraph 0040 of WO 2016 / 181987, the compounds described in JP-A-2015-176046, the compounds described in paragraph 0072 of WO 2016 / 190162, the compounds described in paragraphs 0196 to 0228 of JP-A-2016-074649, the compounds described in paragraph 0124 of JP-A-2017-067963, the compounds described in WO 2017 / 135359, the compounds described in JP-A-2017-114956, the compounds described in JP No. 6197940, the compounds described in WO 2016 / 120166, etc. Examples of the cyanine compounds include the compounds described in paragraphs 0044 to 0045 of JP-A-2009-108267, the compounds described in paragraphs 0026 to 0030 of JP-A-2002-194040, the compounds described in JP-A-2015-172004, the compounds described in JP-A-2015-172102, the compounds described in JP-A-2008-088426, the compounds described in paragraph 0090 of WO 2016 / 190162, the compounds described in JP-A-2017-031394, etc. Examples of the xanthenium compounds include the compounds described in JP-A-2017-082029.As ammonium compounds, for example, compounds described in Japanese Patent Application Laid-Open No. 2008-528706, compounds described in Japanese Patent Application Laid-Open No. 2012-012399, compounds described in Japanese Patent Application Laid-Open No. 2007-092060, and compounds described in paragraphs 0048 to 0063 of International Publication No. 2018 / 043564 can be cited. As phthalocyanine compounds, compounds described in paragraph 0093 of Japanese Patent Application Laid-Open No. 2012-077153, titanium phthalocyanine oxide described in Japanese Patent Application Laid-Open No. 2006-343631, compounds described in paragraphs 0013 to 0029 of Japanese Patent Application Laid-Open No. 2013-195480, vanadium phthalocyanine compounds described in Japanese Patent No. 6081771, vanadium phthalocyanine compounds described in International Publication No. 2020 / 071486, and phthalocyanine compounds described in International Publication No. 2020 / 071470 can be cited. As naphthalocyanine compounds, compounds described in paragraph 0093 of Japanese Patent Application Laid-Open No. 2012-077153 can be cited. As dithiolene metal complexes, compounds described in Japanese Patent 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. Regarding the detailed content of tungsten oxide, reference can be made to paragraph 0080 of Japanese Patent Application Laid-Open No. 2016-006476, and this content is incorporated into the present specification. As metal borides, lanthanum boride, etc. can be cited. As commercially available products of lanthanum boride, LaB6-F (manufactured by JAPAN NEWMETALS CO., LTD.) etc. can be cited. And, as metal borides, compounds described in International Publication No. 2017 / 119394 can also be used. As commercially available products of indium tin oxide, F-ITO (manufactured by DOWA HOLDINGS CO., LTD.) etc. can be cited.
[0376] Further, as the infrared absorber, a squaric acid compound described in JP-A No. 2017-197437, a squaric acid compound described in JP-A No. 2017-025311, a squaric acid compound described in WO 2016 / 154782, a squaric acid compound described in JP No. 5884953, a squaric acid compound described in JP No. 6036689, a squaric acid compound described in JP No. 5810604, a squaric acid compound described in paragraphs 0090 to 0107 of WO 2017 / 213047, a pyrrole ring-containing compound described in paragraphs 0019 to 0075 of JP-A No. 2018-054760, a pyrrole ring-containing compound described in paragraphs 0078 to 0082 of JP-A No. 2018-040955, a pyrrole ring-containing compound described in paragraphs 0043 to 0069 of JP-A No. 2018-002773, a squaric acid compound having an aromatic ring at the amide α-position described in paragraphs 0024 to 0086 of JP-A No. 2018-041047, an amide-linked squaric acid compound described in JP-A No. 2017-179131, a compound having a pyrrole-bifunctional squaric acid skeleton or a croconium skeleton described in JP-A No. 2017-141215, a dihydroxycarbazole-bifunctional squaric acid compound described in JP-A No. 2017-082029, an asymmetric compound described in paragraphs 0027 to 0114 of JP-A No. 2017-068120, a pyrrole ring-containing compound (carbazole type) described in JP-A No. 2017-067963, a phthalocyanine compound described in JP No. 6251530, etc. can also be used.
[0377] The content of the infrared absorber in the total solid components 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 kind of infrared absorber, or may contain two or more kinds. When two or more kinds of infrared absorbers are contained, the total amount thereof is preferably within the above range.
[0378] 《Pigment Derivative》
[0379] The coloring composition of the present invention can contain a pigment derivative. The pigment derivative is used, for example, as a dispersion aid. As the pigment derivative, a compound having a structure in which an acid group or a basic group is bonded to a pigment skeleton can be mentioned.
[0380] Examples of the pigment skeleton constituting the pigment derivative include quinoline pigment skeleton, benzimidazolone pigment skeleton, benzisoindole pigment skeleton, benzothiazole pigment skeleton, iminium pigment skeleton, squaraine pigment skeleton, croconium pigment skeleton, oxonol pigment skeleton, pyrrolopyrrole pigment skeleton, diketopyrrolopyrrole pigment skeleton, azo pigment skeleton, methylene azo pigment skeleton, phthalocyanine pigment skeleton, naphthalocyanine pigment skeleton, anthraquinone pigment skeleton, quinacridone pigment skeleton, dioxazine pigment skeleton, perinone pigment skeleton, perylene pigment skeleton, thioindigo pigment skeleton, isoindoline pigment skeleton, isoindolinone pigment skeleton, quinophthalone pigment skeleton, iminium pigment skeleton, dithiol pigment skeleton, triarylmethane pigment skeleton, pyrromethene pigment skeleton, etc.
[0381] Examples of the acid group include carboxyl group, sulfonic acid group, phosphoric acid group, boric acid group, carboxamide group, sulfonamide group, imido acid group, and salts thereof. Examples of the atom or atomic group 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. Examples of the carboxamide group preferably include a group represented by -NHCOR X1 . Examples of the sulfonamide group preferably include a group represented by -NHSO2R X2 . Examples of the imido acid group preferably include a group represented by -SO2NHSO2R X3 , -CONHSO2R X4 , -CONHCOR X5 or -SO2NHCOR X6 , more preferably -SO2NHSO2R X3 . R X1 to R X6 each independently represent an alkyl group or an aryl group. The alkyl group and aryl group represented by R X1 to R X6 may have a substituent. Examples of the substituent are preferably a halogen atom, more preferably a fluorine atom.
[0382] Examples of the basic group include amino group, pyridyl group and its salt, ammonium group salt, and phthalimidomethyl. Examples of the atom or atomic group constituting the salt include hydroxide ion, halide ion, carboxylate ion, sulfonate ion, phenoxide ion, etc.
[0383] As the pigment derivative, it is also possible to use a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative). The maximum value (εmax) of the molar extinction coefficient of the transparent pigment derivative in the wavelength range of 400 to 700 nm is preferably 3000 L·mol -1 ·cm -1 Hereinafter, it is more preferably 1000 L·mol -1 ·cm -1 Hereinafter, it is further preferably 100 L·mol -1 ·cm -1 Hereinafter. The lower limit of εmax is, for example, 1 L·mol -1 ·cm -1 or more, and may also be 10 L·mol -1 ·cm -1 or more.
[0384] Specific examples of the pigment derivative include the compounds described in the examples 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, 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 Laid-Open No. 2015-151530, paragraphs 0162 to 0183 of Japanese Patent Application Laid-Open No. 2011-252065, Japanese Patent Application Laid-Open No. 03-081972, 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, Japanese Patent Application Laid-Open No. 2008-081565, and the compounds described in International Publication No. 2020 / 002106 having a mercapto linking group. Further, as the pigment derivative, the compound described in paragraph 0281 of International Publication No. 2021 / 215133 can also be used.
[0385] The content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 2 to 15 parts by mass, and further preferably 4 to 10 parts by mass with respect to 100 parts by mass of the pigment.
[0386] Moreover, the content of the pigment derivative is preferably 5 to 50 parts by mass, more preferably 10 to 40 parts by mass, and further preferably 15 to 30 parts by mass with respect to 100 parts by mass of Compound Y.
[0387] One type of pigment derivative may be used alone, or two or more types may be used in combination. When two or more types are used in combination, it is preferable that their total is within the above range.
[0388] 《Polyalkyleneimine》
[0389] The coloring composition of the present invention can also contain polyalkyleneimine. Polyalkyleneimine is used, for example, as a dispersion aid for pigments. A dispersion aid refers to a material for improving the dispersibility of pigments in a coloring composition. Polyalkyleneimine refers to a polymer obtained by ring-opening polymerization of alkyleneimine. Polyalkyleneimine is preferably a polymer having a branched structure containing primary amino groups, secondary amino groups, and tertiary amino groups, respectively. The number of carbon atoms of alkyleneimine is preferably 2 to 6, more preferably 2 to 4, further preferably 2 or 3, and particularly preferably 2.
[0390] The molecular weight of polyalkyleneimine is preferably 200 or more, more preferably 250 or more. The upper limit is preferably 100,000 or less, more preferably 50,000 or less, further preferably 10,000 or less, and particularly preferably 2,000 or less. In addition, regarding the value of the molecular weight of polyalkyleneimine, when the molecular weight can be calculated from the structural formula, the molecular weight of polyalkyleneimine is the value calculated from the structural formula. On the other hand, when the molecular weight of a specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the value of the number average molecular weight measured by the boiling point elevation method is used. And when it is impossible to measure by the boiling point elevation method or it is difficult to measure, the value of the number average molecular weight measured by the viscosity method is used. And when it is impossible to measure by the viscosity method or it is difficult to measure by the viscosity method, the value of the number average molecular weight in terms of polystyrene conversion value measured by the GPC (gel permeation chromatography) method is used.
[0391] The amine value of polyalkyleneimine is preferably 5 mmol / g or more, more preferably 10 mmol / g or more, and further preferably 15 mmol / g or more.
[0392] Specific examples of the alkyleneimine include ethyleneimine, propyleneimine, 1,2-butyleneimine, 2,3-butyleneimine, etc. Preferred are ethyleneimine or propyleneimine, and more preferred is ethyleneimine. The polyalkyleneimine is particularly preferably polyethyleneimine. Further, polyethyleneimine preferably contains 10 mol% or more of primary amino groups, more preferably 20 mol% or more, and still more preferably 30 mol% or more, based on the total of primary, secondary and tertiary amino groups. Examples of commercially available polyethyleneimines include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, P-1000 (manufactured by NIPPONSHOKUBAI CO., LTD.).
[0393] The content of the polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5% by mass. The lower limit is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and still more preferably 1% by mass or more. The upper limit is preferably 4.5% by mass or less, more preferably 4% by mass or less, and still more preferably 3% by mass or less. Further, the content of the polyalkyleneimine is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the pigment. The lower limit is preferably 0.6 part by mass or more, more preferably 1 part by mass or more, and still more preferably 2 parts by mass or more. The upper limit is preferably 10 parts by mass or less, more preferably 8 parts by mass or less. Only one kind of polyalkyleneimine may be used, or two or more kinds may be used. When two or more kinds are used, the total amount thereof is preferably within the above range.
[0394] 《Curing Accelerator》
[0395] 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, amidinium salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, and onium salt compounds. Specific examples of the curing accelerator include the compounds described in paragraphs 0094 to 0097 of International Publication No. 2018 / 056189, the compounds described in paragraphs 0246 to 0253 of Japanese Patent Application Laid-Open No. 2015-034963, the compounds described in paragraphs 0186 to 0251 of Japanese Patent Application Laid-Open No. 2013-041165, the ionic compounds described in Japanese Patent Application Laid-Open No. 2014-055114, the compounds described in paragraphs 0071 to 0080 of Japanese Patent Application Laid-Open No. 2012-150180, the alkoxysilane compounds having an epoxy group described in Japanese Patent Application Laid-Open No. 2011-253054, the compounds described in paragraphs 0085 to 0092 of Japanese Patent No. 5765059, the 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.
[0396] "Ultraviolet Absorbent"
[0397] The coloring composition of the present invention can contain an ultraviolet absorber. As the ultraviolet absorber, conjugated diene compounds, amino diene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, etc. can be used. As specific examples of these compounds, those described in paragraphs 0038 to 0052 of JP-A-2009-217221, paragraphs 0052 to 0072 of JP-A-2012-208374, paragraphs 0317 to 0334 of JP-A-2013-068814, and paragraphs 0061 to 0080 of JP-A-2016-162946 are incorporated herein by reference. As specific examples of the ultraviolet absorber, compounds having the following structures, etc. can be mentioned. As commercially available products of the ultraviolet absorber, for example, UV-503 (manufactured by DAITO CHEMICAL CO., LTD.), Tinuvin series, Uvinul series manufactured by BASF, Sumisorb series manufactured by Sumika Chemtex Company, Limited, etc. can be mentioned. And, as the benzotriazole compound, the MYUA series (Chemical Industry Daily, February 1, 2016) manufactured by MIYOSHI OIL&FAT CO., LTD. can be mentioned. Also, the ultraviolet absorber can also use the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967, the compounds described in paragraphs 0059 to 0076 of International Publication No. 2016 / 181987, and the thioaryl-substituted benzotriazole type ultraviolet absorber described in International Publication No. 2020 / 137819.
[0398] [Chemical formula 29]
[0399]
[0400] In the total solid content of the coloring composition, the content of the ultraviolet absorber is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. In the present invention, one kind of ultraviolet absorber can be used alone, or two or more kinds can be used. When two or more kinds are used, the total amount is preferably within the above range.
[0401] 《Polymerization inhibitor》
[0402] The coloring composition of the present invention can contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, 2,6-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, cerous salts, etc.). Among them, p-methoxyphenol is preferred. In the total solid content of the coloring composition, the content of the polymerization inhibitor is preferably 0.0001 to 5% by mass. The polymerization inhibitor can be only one kind or two or more kinds. In the case of two or more kinds, the total amount is preferably within the above range.
[0403] "Silane Coupling Agent"
[0404] The coloring composition of the present invention can contain a silane coupling agent. In the present invention, the silane coupling agent refers to a silane compound having a hydrolyzable group and a functional group other than the hydrolyzable group. And, the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can form a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group, etc., and an alkoxy group is preferred. That is, the silane coupling agent preferably has a compound having an alkoxysilyl group. And, as the functional group other than the hydrolyzable group, for example, a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a thioether group, an isocyanate group, a phenyl group, etc. are exemplified, and an amino group, a (meth)acryloyl group, and an epoxy group are preferred. Specific examples of the silane coupling agent include N-β-aminoethyl-γ-aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., 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 KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., product name KBM-503), etc. And, as specific examples of the silane coupling agent, compounds described in paragraphs 0018 to 0036 of Japanese Patent Laid-Open No. 2009-288703 and compounds described in paragraphs 0056 to 0066 of Japanese Patent Laid-Open No. 2009-242604 are exemplified, 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, more preferably 0.05 to 10.0% by mass. The silane coupling agent can be only one kind, or two or more kinds. In the case of two or more kinds, the total amount is preferably within the above range.
[0405] "Surfactant"
[0406] The coloring composition of the present invention can contain a surfactant. As the surfactant, various surfactants such as fluorosurfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants can be used. The surfactant is preferably a silicone surfactant or a fluorosurfactant. Regarding the surfactant, reference can be made to the surfactants described in paragraphs 0238 to 0245 of International Publication No. 2015 / 166779, and this content is incorporated into the present specification.
[0407] The fluorine content in the fluorosurfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. The fluorosurfactant having a fluorine content within this range is effective from the viewpoints of the thickness uniformity and liquid-saving property of the coating film, and also has good solubility in the coloring composition.
[0408] As the fluorine-based surfactant, the surfactants described in paragraphs 0060 to 0064 (paragraphs 0060 to 0064 of the corresponding International Publication No. 2014 / 017669) of Japanese Patent Application Laid-Open No. 2014-041318, the surfactants described in paragraphs 0117 to 0132 of Japanese Patent Application Laid-Open No. 2011-132503, and the surfactants described in Japanese Patent Application Laid-Open No. 2020-008634 can be cited. These contents are incorporated into this specification. As commercially available products of fluorine-based surfactants, for example, MEGAFACE F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, F-144, F-437, F-475, F-477, F-479, F-482, F-554, F-555-A, F-556, F-557, F-558, F-559, F-560, F-561, F-565, F-563, F-568, F-575, F-780, EXP, MFS-330, R-01, R-40, R-40-LM, R-41, R-41-LM, RS-43, R-43, TF-1956, RS-90, R-94, RS-72-K, DS-21 (the above are manufactured by DIC CORPORATION), FLUORAD FC430, FC431, FC171 (the above are 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 (the above are manufactured by AGC INC.), PolyFox PF636, PF656, PF6320, PF6520, PF7002 (the above are manufactured by OMNOVA SOLUTIONS INC.), Futurgent 208G, 215M, 245F, 601AD, 601ADH2, 602A, 610FM, 710FL, 710FM, 710FS, FTX-218 (the above are manufactured by NEOS), etc.
[0409] The fluorine-based surfactant can also preferably use an acrylic compound. The acrylic compound has a molecular structure having a functional group containing a fluorine atom, and when heated, the functional group part containing the fluorine atom is cut off and the fluorine atom volatilizes. As such a fluorine-based surfactant, the MEGAFACE DS series manufactured by DIC Corporation (Chemical Industry Daily (February 22, 2016), Nikkei Industrial News (February 23, 2016)) can be cited. For example, MEGAFACE DS-21 can be cited.
[0410] Regarding the fluorine-based surfactant, it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound. As such a fluorine-based surfactant, the fluorine-based surfactant described in JP-A-2016-216602 can be cited, and the content thereof is incorporated into this specification.
[0411] A block polymer can also be used as the fluorine-based surfactant. A fluorine-containing polymer compound is also preferably used as the fluorine-based surfactant, and the fluorine-containing polymer compound includes: 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 group, propyleneoxy group). In addition, the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorine-based surfactants used in the present invention.
[0412] [Chemical formula 30]
[0413]
[0414] The weight average molecular weight of the above compound is preferably 3000 to 50000, for example, 14000. In the above compound, the % representing the ratio of the repeating unit is mol%.
[0415] In addition, a fluorine-containing polymer having a group containing an ethylenically unsaturated bond in the side chain can also be used as the fluorine-based surfactant. As a specific example, the compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of JP-A-2010-164965, MEGAFACE RS-101, RS-102, RS-718K, RS-72-K, etc. manufactured by DIC Corporation can be cited. In addition, the compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used as the fluorine-based surfactant.
[0416] In addition, from the viewpoint of environmental control, it is also preferable to use the surfactant described in International Publication No. 2020 / 084854 as a substitute for the surfactant having a perfluoroalkyl group having 6 or more carbon atoms.
[0417] In addition, it is also preferable to use the fluorine-containing imide salt compound represented by the formula (fi-1) as the surfactant.
[0418] [Chemical formula 31]
[0419]
[0420] In formula (fi-1), m represents 1 or 2, n represents an integer from 1 to 4, a represents 1 or 2, and X a+ represents a metal ion of valence a, a primary ammonium ion, a secondary ammonium ion, a tertiary ammonium ion, a quaternary ammonium ion, or NH4 + .
[0421] Examples of the nonionic surfactant include glycerin, trimethylolpropane, trimethylolethane, and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol 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 ester, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (manufactured by BASF), Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by 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.), etc.
[0422] Examples of the silicone surfactant include DOWSIL SH8400, SH 8400FLUID, FZ-2122, 67Additive, 74Additive, M Additive, SF 8419OIL (all of the above are manufactured by Dow Toray Co., Ltd.), TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all of the above are manufactured by Momentive Performance Materials Inc.), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (all of the above are manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (all of the above are manufactured by BYK Co., LTD), etc.
[0423] Further, in the silicone-based surfactant, a compound having the following structure can also be used.
[0424] [Chemical Formula 32]
[0425]
[0426] In the total solid content of the coloring composition, the content of the surfactant is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% to 3.0% by mass. The surfactant may be only one kind, or two or more kinds. In the case of two or more kinds, the total amount is preferably within the above range.
[0427] <<Antioxidant>
[0428] The coloring composition of the present invention can contain an antioxidant. Examples of the antioxidant include phenolic compounds, phosphite compounds, thioether compounds, etc. As the phenolic compound, any phenolic compound known as a phenolic antioxidant can be used. Preferred phenolic compounds are hindered phenolic compounds. Compounds having a substituent at a position (ortho position) adjacent to the phenolic hydroxyl group are preferred. As the substituent, a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred. Also, the antioxidant preferably has a phenolic group and a phosphite group in the same molecule. Also, a phosphorus-based antioxidant can preferably be used. Examples of the phosphorus-based antioxidant include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenz[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenz[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, etc. Examples of commercially available products of the antioxidant include Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80, Adekastab A0-330 (manufactured by ADEKA Corporation, etc.). Also, the antioxidant can also be a compound described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, a compound described in International Publication No. 2017 / 006600, a compound described in International Publication No. 2017 / 164024, or a compound described in Korean Published Patent No. 10-2019-0059371. The content of the antioxidant in the total solid components of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. The antioxidant can be used alone or in combination of two or more. When two or more are used, the total amount is preferably within the above range.
[0429] 《Other Components》
[0430] The coloring composition of the present invention may contain, as needed, a sensitizer, a curing accelerator, a filler, a heat curing accelerator, a plasticizer, and other auxiliary agents (such as conductive particles, an antifoaming agent, a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension regulator, a chain transfer agent, etc.). The properties such as film physical properties can be adjusted by appropriately containing these components. Regarding these components, for example, reference can be made to the description in paragraphs 0183 et seq. of Japanese Patent Application Laid-Open No. 2012-003225 (corresponding to paragraphs 0237 of the specification of US Patent Application Publication No. 2013 / 0034812), paragraphs 0101 to 0104, 0107 to 0109 of Japanese Patent Application Laid-Open No. 2008-250074, etc., and these contents are incorporated into this specification. Further, as needed, the coloring composition of the present invention may also contain a latent antioxidant. Examples of the latent antioxidant include compounds in which the site that functions as an antioxidant is protected by a protecting group, and the protecting group is removed by heating at 100 to 250 °C or heating in the presence of an acid / alkali catalyst at 80 to 200 °C to function as an antioxidant. Examples of the latent antioxidant include the compounds described in International Publication No. 2014 / 021023, International Publication No. 2017 / 030005, and Japanese Patent Application Laid-Open No. 2017-008219. Examples of commercially available latent antioxidants include ADEKA ARKLS GPA-5001 (manufactured by ADEKA CORPORATION).
[0431] 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 still more preferably 5 to 50 nm. The metal oxide may have a core-shell structure. In this case, the core portion may be hollow.
[0432] The coloring composition of the present invention may contain a light resistance improver. Examples of the light resistance improver include the compounds described in paragraphs 0036 to 0037 of Japanese Patent Application Laid-Open No. 2017-198787, the compounds described in paragraphs 0029 to 0034 of Japanese Patent Application Laid-Open No. 2017-146350, the compounds described in paragraphs 0036 to 0037 and 0049 to 0052 of Japanese Patent Application Laid-Open No. 2017-129774, the compounds described in paragraphs 0031 to 0034 and 0058 to 0059 of Japanese Patent Application Laid-Open No. 2017-129674, the compounds described in paragraphs 0036 to 0037 and 0051 to 0054 of Japanese Patent Application Laid-Open No. 2017-122803, the compounds described in paragraphs 0025 to 0039 of International Publication No. 2017 / 164127, the compounds described in paragraphs 0034 to 0047 of Japanese Patent Application Laid-Open No. 2017-186546, the compounds described in paragraphs 0019 to 0041 of Japanese Patent Application Laid-Open No. 2015-025116, the compounds described in paragraphs 0101 to 0125 of Japanese Patent Application Laid-Open No. 2012-145604, the compounds described in paragraphs 0018 to 0021 of Japanese Patent Application Laid-Open No. 2012-103475, the compounds described in paragraphs 0015 to 0018 of Japanese Patent Application Laid-Open No. 2011-257591, the compounds described in paragraphs 0017 to 0021 of Japanese Patent Application Laid-Open No. 2011-191483, the compounds described in paragraphs 0108 to 0116 of Japanese Patent Application Laid-Open No. 2011-145668, the compounds described in paragraphs 0103 to 0153 of Japanese Patent Application Laid-Open No. 2011-253174, and the like.
[0433] The coloring composition of the present invention also preferably substantially does not contain terephthalate. Here, "substantially does not contain" means that the content of terephthalate in the total amount of the coloring composition is 1000 mass ppb or less, more preferably 100 mass ppb or less, and particularly preferably zero.
[0434] From the perspective of environmental control, the use of perfluoroalkylsulfonic acids and their salts, as well as perfluoroalkylcarboxylic acids and their salts, is sometimes regulated. In the coloring composition of the present invention, when reducing the content rate of the above compounds, the content rate of perfluoroalkylsulfonic acids (especially perfluoroalkylsulfonic acids having 6 to 8 carbon atoms in the perfluoroalkyl group) and their salts, and perfluoroalkylcarboxylic acids (especially perfluoroalkylcarboxylic acids having 6 to 8 carbon atoms in the perfluoroalkyl group) and their salts is preferably in the range of 0.01 ppb to 1,000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and further preferably in the range of 0.1 ppb to 300 ppb, relative to the total solid content of the coloring composition. The coloring composition of the present invention may also substantially not contain perfluoroalkylsulfonic acids and their salts, and perfluoroalkylcarboxylic acids and their salts. For example, by using compounds that can be substitutes for perfluoroalkylsulfonic acids and their salts, and compounds that can be substitutes for perfluoroalkylcarboxylic acids and their salts, a coloring composition that substantially does not contain perfluoroalkylsulfonic acids and their salts, and perfluoroalkylcarboxylic acids and their salts can also be selected. As compounds that can be substitutes for the regulated compounds, for example, compounds removed from the regulated objects due to differences in the number of carbon atoms in the perfluoroalkyl group can be cited. However, the above does not prevent the use of perfluoroalkylsulfonic acids and their salts, and perfluoroalkylcarboxylic acids and their salts. The coloring composition of the present invention may also contain perfluoroalkylsulfonic acids and their salts, and perfluoroalkylcarboxylic acids and their salts within the maximum allowable range.
[0435] The water content of the coloring composition of the present invention is usually 3% by mass or less, preferably in the range of 0.01 to 1.5% by mass, and more preferably in the range of 0.1 to 1.0% by mass. The water content can be measured by the Karl Fischer method.
[0436] For the purpose of adjusting the film surface state (flatness, etc.), adjusting the film thickness, etc., the coloring composition of the present invention can be used by adjusting the viscosity. The value of the viscosity can be appropriately selected as needed. However, for example, at 25 °C, it is preferably 0.3 mPa·s to 50 mPa·s, and more preferably 0.5 mPa·s to 20 mPa·s. As a method for measuring the viscosity, for example, a cone-plate type viscometer can be used to measure in a state where the temperature is adjusted to 25 °C.
[0437] 《Containment Vessel》
[0438] There are no particular limitations on the container for housing the coloring composition, and known containers can be used. Also, as the container for housing, in order to suppress the mixing of impurities into the raw materials or the coloring composition, it is also preferable to use a multilayer bottle having a container inner wall composed of 6 types of 6 layers of resin or a bottle having a 7-layer structure with 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. Also, for the purpose of preventing the elution of metal from the container inner wall, improving the storage stability of the coloring composition, or suppressing the deterioration of components, etc., it is also preferable that the container inner wall is made of glass, stainless steel, or the like.
[0439] <Method for preparing coloring composition>
[0440] The coloring composition of the present invention can be prepared by mixing the above components. When preparing the coloring composition, all the components can be simultaneously dissolved and / or dispersed in a solvent to prepare the coloring composition, or, if necessary, each component can be appropriately made into two or more solutions or dispersions, and these can be mixed at the time of use (coating) to prepare the coloring composition.
[0441] Also, when preparing the coloring composition, a step of dispersing the pigment is preferably included. As the mechanical force for dispersing the pigment in the step of dispersing the pigment, compression, extrusion, impact, shear, cavitation, etc. can be cited. As specific examples of these steps, bead milling, sand milling, roll milling, ball milling, paint stirrer, microfluidization, high-speed impeller, sand mixing, flow jet mixing, high-pressure wet atomization, ultrasonic dispersion, etc. can be cited. Also, in the pulverization of the pigment under sand milling (bead milling), it is preferable to perform the treatment under the following conditions, which are to improve the pulverization efficiency by using microbeads with a small diameter and increasing the filling rate of the microbeads, etc. Also, it is preferable to remove coarse particles by filtration, centrifugation, etc. after the pulverization treatment. Also, regarding the step of dispersing the pigment and the dispersing machine, it is possible to preferably use the processes and dispersing machines described in "The Complete Encyclopedia of Dispersion Technology, published by JOHOKIKO CO., LTD., July 15, 2005" or "Comprehensive Data Set on Dispersion Technology and Industrial Practical Applications Centering on Suspensions (Solid / Liquid Dispersion Systems), published by the Business Development Center Publishing Department, October 10, 1978", and the processes and dispersing machines described in paragraph 0022 of Japanese Patent Application Laid-Open No. 2015-157893. Also, in the step of dispersing the pigment, the particle size reduction treatment can be performed by a salt milling step. The raw materials, equipment, treatment conditions, etc. used in the salt milling step can be referred to, for example, in the descriptions of Japanese Patent Application Laid-Open No. 2015-194521 and Japanese Patent Application Laid-Open No. 2012-046629.
[0442] When preparing a coloring composition, in order to remove impurities or reduce defects, etc., it is preferable to filter the coloring composition with a filter. As the filter, as long as it is a filter that has been used for filtration purposes, etc., it can be used without particular limitation. For example, filters made of materials such as fluororesins like polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF), polyamide resins such as nylon (e.g., nylon-6, nylon-6,6), and polyolefin resins such as polyethylene and polypropylene (PP) (including high-density and ultra-high molecular weight polyolefin resins) can be cited. Among these materials, polypropylene (including high-density polypropylene) and nylon are preferred.
[0443] 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 impurities can be removed more reliably. Regarding the pore size value of the filter, the nominal value provided by the filter manufacturer can be referred to. Regarding the filter, various filters provided by NIHON PALL Corporation (such as DFA4201NXEY, DFA4201NAEY, DFA4201J006P), Advantec Toyo Kaisha, Ltd., NihonEntegris K.K. (Formerly Nippon Mykrolis Corporation), and KITZ MICROFILTER Corporation, etc. can be used.
[0444] Moreover, as the filter, it is also preferable to use fibrous filter materials. As the fibrous filter materials, for example, polypropylene fibers, nylon fibers, glass fibers, etc. can be cited. As commercially available products, the SBP type series (such as SBP008), TPR type series (such as TPR002, TPR005), and SHPX type series (such as SHPX003) manufactured by ROKI TECHNO CO., LTD. can be cited.
[0445] When using the filter, different filters can be combined (for example, the first filter and the second filter, etc.). At this time, the filtration with each filter can be carried out only once, or can be carried out two or more times. And, filters with different pore sizes can be combined within the above range. Also, the filtration with the first filter can be carried out only on the dispersion liquid, and after mixing other components, the second filter can be used for filtration. And, the filter can be appropriately selected according to the hydrophilicity and hydrophobicity of the composition.
[0446] <Film>
[0447] The film of the present invention is a film obtained from the coloring composition of the present invention described above. The film of the present invention can also be used for filters such as color filters or infrared transmission filters.
[0448] 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 still more preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and still more preferably 0.3 μm or more.
[0449] 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, blue, magenta or yellow, and more preferably has a hue of green, red or yellow. Further, the film of the present invention can preferably be used as a colored pixel of a color filter. Examples of the colored pixel include a red pixel, a green pixel, a blue pixel, a magenta pixel, a cyan pixel, a yellow pixel, etc., preferably a red pixel, a green pixel and a yellow pixel, more preferably a red pixel or a green pixel, and still more preferably a green pixel.
[0450] Further, in the film of the present invention, it is preferable that a wavelength at which the light transmittance becomes 50% exists in the wavelength range of 470 to 520 nm, more preferably exists in the wavelength range of 475 to 520 nm, and still more preferably exists in the wavelength range of 480 to 520 nm. Among them, the wavelengths at which the light transmittance becomes 50% preferably exist in the wavelength ranges of 470 to 520 nm and 575 to 625 nm, respectively. In this mode, the wavelength on the short wavelength side at which the light transmittance becomes 50% preferably exists in the wavelength range of 475 to 520 nm, more preferably exists in the wavelength range of 480 to 520 nm. Further, the wavelength on the long wavelength side at which the light transmittance becomes 50% preferably exists in the wavelength range of 580 to 620 nm, more preferably exists in the wavelength range of 585 to 615 nm. The film having such spectral characteristics can preferably be used as a green pixel.
[0451] 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).
[0452] (1): The maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of the light transmittance in the thickness direction of the film in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more). The film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light having a wavelength exceeding 700 nm.
[0453] (2): A film in which the maximum value of the light transmittance in the thickness direction of the film is 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 750 nm, and the minimum value of the light transmittance in the thickness direction of the film is 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 900 to 1300 nm. A film having such spectral characteristics can block light in the range of 400 to 750 nm in wavelength and transmit light with a wavelength exceeding 850 nm.
[0454] (3): A film in which the maximum value of the light transmittance in the thickness direction of the film is 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 830 nm, and the minimum value of the light transmittance in the thickness direction of the film is 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1000 to 1300 nm. A film having such spectral characteristics can block light in the range of 400 to 830 nm in wavelength and transmit light with a wavelength exceeding 940 nm.
[0455] (4): A film in which the maximum value of the light transmittance in the thickness direction of the film is 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 950 nm, and the minimum value of the light transmittance in the thickness direction of the film is 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm. A film having such spectral characteristics can block light in the range of 400 to 950 nm in wavelength and transmit light with a wavelength exceeding 1040 nm.
[0456] <Method for manufacturing the film>
[0457] Next, the method for manufacturing the film of the present invention will be described. The film of the present invention can be manufactured through a step of coating the coloring composition of the present invention. In the method for manufacturing the film, a step of forming a pattern (pixel) is preferably further included. As the method for forming the pattern (pixel), photolithography and dry etching can be mentioned, and photolithography is preferred.
[0458] The pattern formation based on photolithography preferably includes the following steps: a step of forming a coloring composition layer on a support using the coloring composition of the present invention; a step of exposing the coloring composition layer into a pattern shape; and a step of developing and removing the unexposed portion of the coloring composition layer to form a pattern (pixel). If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixel) (post-baking step) can also be provided.
[0459] In the step of forming the colored composition layer of the present invention, a colored composition layer is formed on a support using the colored composition. The support is not particularly limited and can be appropriately selected according to the use. For example, a glass substrate, a silicon substrate, etc. can be mentioned, and a silicon substrate is preferred. And, a charge-coupled device (CCD), a complementary metal-oxide semiconductor (CMOS), a transparent conductive film, etc. can be formed on the silicon substrate. And, a black matrix for isolating each pixel may be formed on the silicon substrate. And, in order to improve the adhesion to the upper layer, prevent the diffusion of substances, or planarize the substrate surface, a base layer can be provided on the silicon substrate. The base layer can also be formed using a composition obtained by removing a colorant 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.
[0460] As a coating method of the colored composition, a known method can be used. For example, a dropping method (drop coating); a slit coating method; a spraying method; a roll coating method; a spin coating method (spin coating); a casting coating method; a slit spin coating method; a pre-wetting method (for example, the method described in Japanese Patent Application Laid-Open No. 2009-145395); various printing methods such as inkjet (for example, on-demand method, piezoelectric method, thermal method), nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc.; a transfer method using a mold, etc.; a nanoimprint method, etc. There is no particular limitation on the application method in inkjet. For example, the method shown in "Inkjet that can be popularized and used - Infinite possibilities in patents -", published in February 2005, Sumitbe Techon Research Co., Ltd. (especially pages 115 to 133) or the methods described in Japanese Patent Application Laid-Open No. 2003-262716, Japanese Patent Application Laid-Open No. 2003-185831, Japanese Patent Application Laid-Open No. 2003-261827, Japanese Patent Application Laid-Open No. 2012-126830, Japanese Patent Application Laid-Open No. 2006-169325, etc. can be mentioned. And, regarding the coating method of the colored composition, the descriptions in International Publication No. 2017 / 030174 and International Publication No. 2017 / 018419 can be referred to, and these contents are incorporated into this specification.
[0461] The colored composition layer formed on the support can be dried (pre-baked). In the case of manufacturing a film by a low-temperature process, pre-baking may not be performed. In the case of performing pre-baking, the pre-baking temperature is preferably 150 °C or lower, more preferably 120 °C or lower, and further preferably 110 °C or lower. The lower limit can be set, for example, to 50 °C or higher, or can also be set to 80 °C or higher. The pre-baking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and further preferably 80 to 220 seconds. Pre-baking can be carried out using a hot plate, an oven, or the like.
[0462] Next, the colored composition layer is exposed in a pattern (exposure process). For example, using a step exposure machine, a scanning exposure machine, etc., the colored composition layer is exposed through a mask having a predetermined mask pattern, whereby it can be exposed in a pattern. Thus, the exposed portion can be cured.
[0463] Examples of the radiation (light) that can be used during exposure include g-rays, i-rays, etc. Also, light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can be used. Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm), ArF rays (wavelength 193 nm), etc., and KrF rays (wavelength 248 nm) are preferred. Also, a light source with a long wavelength of 300 nm or more can be utilized.
[0464] Also, during exposure, exposure can be performed by continuously irradiating light, or exposure can be performed by pulsed irradiation (pulsed exposure). In addition, pulsed exposure refers to an exposure method in which light irradiation and pause are repeated in a short cycle (for example, millisecond level or less) for exposure.
[0465] The irradiation amount (exposure amount) is, for example, preferably 0.03 to 2.5 J / cm 2 , more preferably 0.05 to 1.0 J / cm 2 . Regarding the oxygen concentration during exposure, it can be appropriately selected. In addition to performing it under the atmosphere, for example, exposure can be performed in a low-oxygen environment where the oxygen concentration is 19 vol% or less (for example, 15 vol%, 5 vol% or substantially oxygen-free), or exposure can be performed in a high-oxygen environment where the oxygen concentration exceeds 21 vol% (for example, 22 vol%, 30 vol% or 50 vol%). Also, the exposure illuminance can be appropriately set, and generally, it can be selected from the range of 1000 W / m 2 ~100000 W / m 2 (for example, 5000 W / m 2 , 15000 W / m 2 or 35000 W / m 2 ). The oxygen concentration and the exposure illuminance can be appropriately combined with conditions. For example, it can be set to an oxygen concentration of 10 vol% and an illuminance of 10000 W / m2 , oxygen concentration of 35% by volume and illuminance of 20000 W / m 2 and so on.
[0466] Next, the unexposed portion of the colored composition layer is developed and removed to form a pattern (pixel). The development and removal of the unexposed portion of the colored composition layer can be carried out using a developer. Thus, the unexposed portion of the colored composition layer in the exposure process dissolves 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. And, in order to improve the residue removal property, the process of discarding the developer every 60 seconds and then supplying a new developer can be repeated multiple times.
[0467] Examples of the developer include organic solvents, alkaline developers, etc., and an alkaline developer is preferably used. As the alkaline developer, an alkaline aqueous solution (alkaline developer) obtained by diluting an alkali agent with pure water is preferred. Examples of the alkali agent include organic basic 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 basic compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium silicate, and sodium metasilicate. In terms of the environment and safety, the alkali agent is preferably a compound with a large molecular weight. The concentration of the alkali agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass. And, the developer may also contain a surfactant. From the viewpoints of convenient transportation or storage, etc., the developer can be temporarily manufactured as a concentrated solution and diluted to the required concentration when used. The dilution ratio is not particularly limited, and can be set in the range of 1.5 to 100 times, for example. And, it is also preferred to wash (rinse) with pure water after development. And, it is preferred to carry out rinsing by rotating the support on which the developed colored composition layer has been formed and supplying a rinsing liquid to the developed colored composition layer. And, it is also preferred to carry out rinsing by moving the nozzle that discharges the rinsing liquid from the center portion of the support to the peripheral portion of the support. At this time, when moving from the center portion of the support to the peripheral portion of the nozzle, the moving speed of the nozzle can be gradually decreased while moving. By rinsing in this way, the in-plane deviation of rinsing can be suppressed. And, the same effect can also be obtained by gradually decreasing the rotation speed of the support while moving the nozzle from the center portion of the support to the peripheral portion.
[0468] Preferably, after development, additional exposure treatment and heat treatment (post-baking) are performed after drying. The additional exposure treatment and post-baking are curing treatments after development for making a fully cured product. The heating temperature in the post-baking is preferably, for example, 100 to 240°C, more preferably 200 to 240°C. The film after development can be post-baked in a continuous or batch manner using a heating mechanism such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heating machine so as to satisfy the above conditions. In the case of performing the additional exposure treatment, the light used for exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure treatment can be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
[0469] Pattern formation based on the dry etching method preferably includes the following steps: a step of forming a colored composition layer on a support using the colored composition of the present invention and curing the entire colored composition layer to form a cured product layer; a step of forming a photoresist layer on the cured product layer; a step of exposing the photoresist layer in a pattern shape and then developing it to form a resist pattern; and a step of using the resist pattern as a mask and performing dry etching on the cured product layer using an etching gas. When forming the photoresist layer, it is preferable to further perform a pre-baking treatment. In particular, as the formation process of the photoresist layer, a form in which heat treatment after exposure and heat treatment after development (post-baking treatment) are preferably performed can be mentioned. Regarding pattern formation using the dry etching method, reference can be made to paragraphs 0010 to 0067 of Japanese Patent Laid-Open No. 2013-064993, and the content is incorporated herein.
[0470] <Filter>
[0471] The filter of the present invention has the film of the present invention described above. As the types of filters, a color filter and an infrared transmission filter can be mentioned, and a color filter is preferably used. As the color filter, a colored pixel having the film of the present invention as the color filter is preferably used.
[0472] A protective layer can be provided on the surface of the film of the present invention. By providing the protective layer, various functions such as oxidation resistance, low reflectance, hydrophilic / hydrophobic modification, and shielding of light with specific wavelengths (ultraviolet light, near-infrared light, etc.) can be imparted. As the thickness of the protective layer, 0.01 to 10 μm is preferable, and 0.1 to 5 μm is more preferable. As the method for forming the protective layer, methods such as forming by coating a resin composition dissolved in an organic solvent, chemical vapor deposition method, and method of attaching a molded resin with an adhesive material can be mentioned. As the components constituting the protective layer, (meth)acrylic resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polystyrene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, polyurethane resin, aromatic polyamide resin, polyamide resin, alkyd resin, epoxy resin, modified polysiloxane resin, fluororesin, polycarbonate resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al2O3, Mo, SiO2, Si2N4, etc. can be mentioned, and two or more of these components can be contained. For example, in the case of a protective layer for oxidation resistance, it is preferable that the protective layer contains a polyol resin, SiO2, and Si2N4. And, in the case of a protective layer for low reflectance, it is preferable that the protective layer contains a (meth)acrylic resin and a fluororesin.
[0473] In the case of forming a protective layer by coating a resin composition, as the coating method of the resin composition, known methods such as spin coating method, casting method, screen printing method, inkjet method, etc. can be used. As the organic solvent contained in the resin composition, known organic solvents (for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.) can be used. In the case of forming a protective layer by chemical vapor deposition method, as the chemical vapor deposition method, known chemical vapor deposition methods (thermal chemical vapor deposition method, plasma chemical vapor deposition method, photo chemical vapor deposition method) can be used.
[0474] As needed, the protective layer can further contain additives such as organic / inorganic fine particles, absorbers for light with specific wavelengths (for example, ultraviolet light, near-infrared light, etc.), refractive index adjusters, antioxidants, adhesives, surfactants, etc. As examples of the organic / inorganic fine particles, for example, polymer fine particles (for example, polysiloxane fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, oxynitride titanium, magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate, etc. can be mentioned. Absorbers for light with specific wavelengths can use known absorbers. The content of these additives can be appropriately adjusted, but it is preferably 0.1 to 70% by mass, and more preferably 1 to 60% by mass with respect to the total mass of the protective layer.
[0475] Further, as the protective layer, the protective layer described in paragraphs 0073 to 0092 of Japanese Unexamined Patent Application Publication No. 2017-151176 can also be used.
[0476] The filter may also have a structure in which each pixel is embedded in a space separated by partition walls, for example, in a grid pattern.
[0477] <Solid-state imaging device>
[0478] The solid-state imaging device of the present invention has the 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. For example, the following structures can be cited.
[0479] The structure of the imaging device is as follows: on a substrate, there is a transfer electrode composed of a plurality of photodiodes and polysilicon or the like that form a light-receiving region of a solid-state imaging device (CCD (charge-coupled device) image sensor, CMOS (complementary metal-oxide-semiconductor) image sensor, etc.). On the photodiodes and the transfer electrode, there is a light-shielding film with only the light-receiving portion of the photodiodes opened. On the light-shielding film, there is an element protective film composed of silicon nitride or the like formed so as to cover the entire surface of the light-shielding film and the light-receiving portion of the photodiodes. On the element protective film, there is a color filter. Moreover, it can be a structure having a condensing mechanism (for example, a microlens, etc. The same applies hereinafter) on the device protective film and on the lower side (the side closer to the substrate) of the color filter, or a structure having a condensing mechanism on the color filter. Further, the color filter may also have a structure in which each colored pixel is embedded in a space separated by partition walls, for example, in a grid pattern. In this case, the refractive index of the partition walls is preferably lower than that of each colored pixel. As an example of an imaging device having such a structure, the devices described in Japanese Unexamined Patent Application Publication No. 2012-227478, Japanese Unexamined Patent Application Publication No. 2014-179577, and International Publication No. 2018 / 043654 can be cited. Also, as shown in Japanese Unexamined Patent Application Publication No. 2019-211559, providing an ultraviolet absorption layer in the structure of the solid-state imaging device can also improve light resistance. The imaging device equipped with the solid-state imaging device of the present invention can be used not only as a digital camera or an electronic device having a imaging function (such as a mobile phone), but also as an in-vehicle camera or a surveillance camera.
[0480] <Image display device>
[0481] The image display device of the present invention has the film of the present invention described above. Examples of the image display device include a liquid crystal display device or an organic electroluminescence display device. The definition of the image display device and the details of each image display device are described, for example, in "Electronic Display Devices (by Akio Sasaki, published by Kogyo Chosakai Publishing Co., Ltd., in 1990)", "Display Devices (by Junsho Ibuki, published by Sangyo Tosho Publishing Co., Ltd., in 1989)", etc. And, regarding liquid crystal display devices, it is described, for example, in "Next-generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Chosakai Publishing Co., Ltd., in 1994)". There is no particular limitation on the liquid crystal display device to which the present invention can be applied, and for example, it can be applied to liquid crystal display devices of various types described in the above-mentioned "Next-generation Liquid Crystal Display Technology".
[0482] Examples
[0483] Hereinafter, examples are given to further specifically illustrate the present invention. The materials, amounts used, ratios, processing contents, processing sequences, etc. shown in the following examples can be appropriately changed as long as they do not deviate from the gist of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. In addition, in the structural formulas shown below, Me represents a methyl group, Et represents an ethyl group, and Ph represents a phenyl group.
[0484] <Synthesis Example of Compound Y>
[0485] (Synthesis Example 1) Synthesis of Compound (Y-1)
[0486] [Chemical Formula 33]
[0487]
[0488] To 13.9 parts by mass of compound (a-1), 1 equivalent of compound (b-1) and 5 parts by mass of methanol were added, and the mixture was heated and stirred for 1 hour at an external temperature of 65 °C under a nitrogen stream. After cooling the liquid temperature to 30 °C, the resulting solid was filtered out and washed with 5 parts by mass of methanol. The obtained solid was dried by blowing air at 50 °C to obtain 20.5 parts by mass of compound (S-1). Subsequently, 1 equivalent of copper(II) acetate monohydrate (Cu(OAc)₂) and 6 parts by mass of N-ethylpyrrolidone (NEP) were mixed with 10 parts by mass of compound (S-1), and the mixture was heated and stirred for 2 hours at an external temperature of 80 °C under a nitrogen stream. Then, 13 parts by mass of ethyl acetate was added dropwise, and after heating and stirring for 30 minutes, 27 parts by mass of ethyl acetate was added dropwise, and the mixture was heated and stirred for 1 hour. After cooling the liquid temperature to 30 °C, the resulting solid was filtered out and washed with 10 parts by mass of ethyl acetate and 10 parts by mass of acetone. The obtained solid was dried by blowing air at 50 °C to obtain 11.2 parts by mass of compound (Y-1), which is a compound in which compound (S-1) is coordinated to a copper atom. The value of (M+H)(posi) in the mass spectrum of compound (Y-1) was 304. The maximum absorption wavelength of compound (Y-1) exists in the range of wavelengths 400 to 500 nm.
[0489] (Synthesis Examples 2 to 44, 48, 50, 52, 56, 87) Synthesis of Compound (Y-2) to Compound (Y-44), Compound (Y-48), Compound (Y-50), Compound (Y-52), Compound (Y-56), Compound (Y-87)
[0490] The compounds (a-1) and (b-1) in Synthesis Example 1 were respectively changed to the compounds described in the column of compound (a) and the column of compound (b) in the following table, and otherwise, the same operations as in Synthesis Example 1 were carried out to synthesize Compound (Y-2) to Compound (Y-44), Compound (Y-48), Compound (Y-50), Compound (Y-52), Compound (Y-56), Compound (Y-87). Compounds (Y-2) to (Y-44), Compound (Y-48), Compound (Y-50), Compound (Y-52), Compound (Y-56), Compound (Y-87) are compounds in which the compounds described in the column of compound S in the following table are coordinated to a copper atom. The maximum absorption wavelengths of compounds (Y-2) to (Y-44), Compound (Y-48), Compound (Y-50), Compound (Y-52), Compound (Y-56), Compound (Y-87) exist in the range of wavelengths 400 to 700 nm. In addition, when a compound having an amino group is used as compound S, acetic acid and salts used for complex formation are sometimes formed.
[0491] (Synthesis Examples 45, 46, 47, 49, 51, 53, 54, 55, 57, 68 - 86) Synthesis of Compound (Y - 45), Compound (Y - 46), Compound (Y - 47), Compound (Y - 49), Compound (Y - 51), Compound (Y - 53), Compound (Y - 54), Compound (Y - 55), Compound (Y - 57), Compound (Y - 68) - Compound (Y - 86)
[0492] The compounds (a - 1) and (b - 1) in Synthesis Example 1 were respectively changed to the compounds described in the column of compound (a) and the column of compound (b) in the following table, and copper(II) acetate monohydrate was changed to zinc(II) acetate dihydrate. Otherwise, the same operations as in Synthesis Example 1 were carried out to synthesize Compound (Y - 45), Compound (Y - 46), Compound (Y - 47), Compound (Y - 49), Compound (Y - 51), Compound (Y - 53), Compound (Y - 54), Compound (Y - 55), Compound (Y - 57), Compound (Y - 68) - Compound (Y - 86). Compounds (Y - 45), (Y - 46), (Y - 47), (Y - 49), (Y - 51), (Y - 53), (Y - 54), (Y - 55), (Y - 57), (Y - 68) - (Y - 86) are compounds in which the compound described in the column of compound S in the following table is coordinated to a zinc atom. The maximum absorption wavelengths of Compounds (Y - 45), (Y - 46), (Y - 47), (Y - 49), (Y - 51), (Y - 53), (Y - 54), (Y - 55), (Y - 57), (Y - 68) - (Y - 86) are in the range of 400 - 600 nm. In addition, when a compound having an amino group is used as compound S, acetic acid and salts used for complex formation may sometimes be formed.
[0493] (Synthesis Examples 58 - 67) Synthesis of Compound (Y - 58) - Compound (Y - 67)
[0494] The compound (a-1) and the compound (b-1) in Synthesis Example 1 were respectively changed to the compounds described in the column of compound (a) and the column of compound (b) in the following table, and copper(II) acetate monohydrate was changed to iron(III) acetate, titanium(IV) isopropoxide, basic aluminum acetate, tetraethyl orthosilicate, or calcium(II) acetate monohydrate. Except for this, the same operations as in Synthesis Example 1 were carried out to synthesize compounds (Y-58) to (Y-67). Compounds (Y-58) to (Y-67) are compounds in which the compounds described in the column of compound S in the following table are coordinated to the metal atoms described in the column of metal atoms in the following table. The maximum absorption wavelengths of compounds (Y-58) to (Y-67) are in the range of wavelengths 400 to 600 nm. In addition, when a compound having an amino group is used as compound S, acetic acid and salts used in complex formation are sometimes formed.
[0495] [Table 1]
[0496]
[0497] [Table 2]
[0498]
[0499] [Table 3]
[0500]
[0501] [Table 4]
[0502]
[0503] [Table 5]
[0504]
[0505] [Table 6]
[0506]
[0507] [Table 7]
[0508]
[0509] [Table 8]
[0510]
[0511] [Table 9]
[0512]
[0513] [Table 10]
[0514]
[0515] [Table 11]
[0516]
[0517] [Table 12]
[0518]
[0519] [Table 13]
[0520]
[0521] [Table 14]
[0522]
[0523] [Table 15]
[0524]
[0525] [Table 16]
[0526]
[0527] [Table 17]
[0528]
[0529] [Manufacture of Dispersion Liquid]
[0530] Using a bead mill (zirconia microbeads with a diameter of 0.1 mm), a mixed liquid containing the raw materials listed in the following table was mixed and dispersed for 3 hours. Then, a high-pressure homogenizer NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) equipped with a decompression mechanism was used for dispersion treatment under the conditions of a pressure of 2000 kg / cm 2 and a flow rate of 500 g / min. This dispersion treatment was repeated a total of 10 times to obtain a dispersion liquid. In addition, in the following table, the values of the blending amounts of Colorants 1 to 4, infrared absorbers, pigment derivatives, and dispersants are values in terms of solid components.
[0531] [Table 18]
[0532]
[0533] [Table 19]
[0534]
[0535] [Table 20]
[0536]
[0537] [Table 21]
[0538]
[0539] [Table 22]
[0540]
[0541] [Table 23]
[0542]
[0543] [Table 24]
[0544]
[0545] [Table 25]
[0546]
[0547] [Table 26]
[0548]
[0549] [Table 27]
[0550]
[0551] [Table 28]
[0552]
[0553] [Table 29]
[0554]
[0555] [Table 30]
[0556]
[0557] The raw materials recorded in the above tables in abbreviated form are as follows.
[0558] (Colorant)
[0559] Y-1 to Y-87: The above compounds Y-1 to Y-87
[0560] Yb-1: A compound of the following structure (C.I. Pigment Yellow 129)
[0561] [Chemical Formula 34]
[0562]
[0563] yy-1 to yy-4: Compounds of the following structure
[0564] [Chemical Formula 35]
[0565]
[0566] yy - 11 to yy - 20: Compounds of the following structure
[0567] [Chemical Formula 36]
[0568]
[0569] [Chemical Formula 37]
[0570]
[0571] PG36: C.I. Pigment Green 36 (phthalocyanine compound, green pigment)
[0572] PG58: C.I. Pigment Green 58 (phthalocyanine compound, green pigment)
[0573] PG59: C.I. Pigment Green 59 (phthalocyanine compound, green pigment)
[0574] PG63: C.I. Pigment Green 63 (phthalocyanine compound, green pigment)
[0575] PR254: C.I. Pigment Red 254 (diketopyrrolopyrrole compound, red pigment)
[0576] PR264: C.I. Pigment Red 264 (diketopyrrolopyrrole compound, red pigment)
[0577] PR272: C.I. Pigment Red 272 (diketopyrrolopyrrole compound, red pigment)
[0578] PY139: C.I. Pigment Yellow 139 (isoindoline compound, yellow pigment)
[0579] PY150: C.I. Pigment Yellow 150 (azo compound, yellow pigment)
[0580] PY155: C.I. Pigment Yellow 155 (azo compound, yellow pigment)
[0581] PY185: C.I. Pigment Yellow 185 (isoindoline compound, yellow pigment)
[0582] PY215: C.I. Pigment Yellow 215 (pteridine compound, yellow pigment)
[0583] PO71: C.I. Pigment Orange 71 (diketopyrrolopyrrole compound, orange pigment)
[0584] PB15:6: C.I. Pigment Blue 15:6 (phthalocyanine compound, blue pigment)
[0585] (Infrared absorber)
[0586] IR-1: A compound with the following structure
[0587] [Chemical formula 38]
[0588]
[0589] (Pigment derivative)
[0590] A-1 to A-6: Compounds with the following structure
[0591] [Chemical formula 39]
[0592]
[0593] [Chemical formula 40]
[0594]
[0595] (Dispersant)
[0596] B-1: A resin with the following structure (the values attached to the main chain are molar ratios, and the values attached to the side chain are the number of repeating units. Weight-average molecular weight 24000)
[0597] [Chemical formula 41]
[0598]
[0599] B-2: A resin with the following structure (the values attached to the main chain are molar ratios, and the values attached to the side chain are the number of repeating units. Weight-average molecular weight 10000)
[0600] [Chemical formula 42]
[0601]
[0602] B-3: A resin with the following structure (the values attached to the main chain are molar ratios, and the values attached to the side chain are the number of repeating units. Weight-average molecular weight 22000)
[0603] [Chemical formula 43]
[0604]
[0605] B-4: A resin with the following structure (the values attached to the main chain are molar ratios, and the values attached to the side chain are the number of repeating units. Weight-average molecular weight 16000)
[0606] [Chemical formula 44]
[0607]
[0608] B-5: Resin with the following structure (the values attached to the main chain are molar ratios, and the values attached to the side chain are the number of repeating units. Weight-average molecular weight: 20,000)
[0609] [Chemical formula 45]
[0610]
[0611] B-6: Resin with the following structure (the values attached to the main chain are molar ratios, and the values attached to the side chain are the number of repeating units. Weight-average molecular weight: 7,000)
[0612] [Chemical formula 46]
[0613]
[0614] B-7: Resin synthesized by the following method
[0615] An appropriate amount of nitrogen gas was passed through a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, and the atmosphere was replaced with nitrogen. 340 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) was added, and the mixture was stirred and heated to 80°C. Then, a mixed solution of 57 parts by mass of acrylic acid, 54 parts by mass of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 decane-9-yl acrylate (containing a molar ratio of 1:1), 239 parts by mass of benzyl methacrylate, and 73 parts by mass of PGMEA was added dropwise over 5 hours. Then, a solution prepared by dissolving 40 parts by mass of a polymerization initiator (2,2-azobis(2,4-dimethylvaleronitrile)) in 197 parts by mass of PGMEA was added dropwise over 6 hours. After the addition of the polymerization initiator solution was completed, the mixture was maintained at 80°C for 3 hours and then cooled to room temperature to obtain a resin with the following structure. The weight-average molecular weight of the obtained resin was 9,400, the dispersity was 1.89, and the acid value was 114 mg KOH / g.
[0616] [Chemical formula 47]
[0617]
[0618] (Solvent)
[0619] Z-1: Propylene glycol monomethyl ether acetate (PGMFA)
[0620] <Manufacture of coloring composition>
[0621] The raw materials listed in the following table were mixed to manufacture a coloring composition.
[0622] [Table 31]
[0623]
[0624] [Table 32]
[0625]
[0626] [Table 33]
[0627]
[0628] [Table 34]
[0629]
[0630] [Table 35]
[0631]
[0632] [Table 36]
[0633]
[0634] [Table 37]
[0635]
[0636] [Table 38]
[0637]
[0638] [Table 39]
[0639]
[0640] [Table 40]
[0641]
[0642] [Table 41]
[0643]
[0644] [Table 42]
[0645]
[0646] [Table 43]
[0647]
[0648] [Table 44]
[0649]
[0650] [Table 45]
[0651]
[0652] The raw materials recorded in the above table in abbreviated form are as follows.
[0653] (Dispersion liquid)
[0654] Dispersion liquids 1 to 79, 101 to 133, 201 to 251, Comparative dispersion liquids 1 and 2: The above-mentioned dispersion liquids 1 to 79, Comparative dispersion liquids 1 and 2
[0655] (Binder)
[0656] B-1: The above-mentioned dispersant B-1
[0657] B-4: The above-mentioned dispersant B-4
[0658] C-1: Resin with the following structure (the values attached to the main chain are molar ratios. Weight-average molecular weight 11000)
[0659] [Chemical formula 48]
[0660]
[0661] C-2: Resin with the following structure (the values attached to the main chain are molar ratios. Weight-average molecular weight 30000)
[0662] [Chemical formula 49]
[0663]
[0664] C-3: Resin with the following structure (the values attached to the main chain are mass ratios. Weight-average molecular weight 14600)
[0665] [Chemical formula 50]
[0666]
[0667] C-4: Resin with the following structure (the values attached to the main chain are mass ratios. Weight-average molecular weight 10600)
[0668] [Chemical formula 51]
[0669]
[0670] C-5: Resin synthesized by the following method
[0671] An appropriate amount of nitrogen gas was passed through a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to displace the air with nitrogen, and 371 parts by mass of 1-methoxy-2-propyl propionate was added. The mixture was stirred and heated to 85 °C. Subsequently, a mixed solution of 54 parts by mass of acrylic acid, 225 parts by mass of a mixture of 3,4-epoxytricyclo[5.2.1.02,6]decane-8- and 9-yl acrylate, 81 parts by mass of vinyltoluene (isomer mixture), and 80 parts by mass of 1-methoxy-2-propyl propionate was added dropwise over 4 hours. On the other hand, a solution prepared by dissolving 30 parts by mass of a polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 160 parts by mass of 1-methoxy-2-propyl propionate was added dropwise over 5 hours. After the addition of the initiator solution was completed, the mixture was maintained at 85 °C for 4 hours and then cooled to room temperature to obtain a resin. The weight-average molecular weight of the obtained resin was 10,600, the dispersity was 2.01, and the acid value was 43 mg KOH / g.
[0672] (Monomer)
[0673] D-1: A compound having the following structure
[0674] [Chemical formula 52]
[0675]
[0676] D-2: A mixture of compounds having the following structures (a mixture of the left compound (a 6-functional (meth)acrylate compound) and the right compound (a 5-functional (meth)acrylate compound) in a molar ratio of 7:3)
[0677] [Chemical formula 53]
[0678]
[0679] D-3: A compound having the following structure
[0680] [Chemical formula 54]
[0681]
[0682] D-4: Trimethylolpropane ethylene oxide modified triacrylate (manufactured by TOAGOSEI CO., LTD., ARONIX M-350)
[0683] D-5: EBECRYL 80 (manufactured by DAICEL-ALLNEX LTD., amine-containing 4-functional acrylate)
[0684] D-6: Ethoxylated dipentaerythritol hexamethacrylate
[0685] (Photoinitiator)
[0686] E-1 to E-4: Compounds with the following structures
[0687] E-5: 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole
[0688] [Chemical formula 55]
[0689]
[0690] (Surfactant)
[0691] F-1: KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone-based surfactant, dimethylpolysiloxane modified with methanol at both ends, hydroxyl value 62 mg KOH / g)
[0692] F-2: Compound with the following structure (weight average molecular weight 14000). In the following formula, mol% represents the proportion of the repeating unit. (Fluorine-based surfactant)
[0693] [Chemical formula 56]
[0694]
[0695] F-3: Futurgent 208G (manufactured by NEOS above, fluorine-based surfactant)
[0696] F-4: BYK-330 (manufactured by BYK Co., LTD, silicone-based surfactant)
[0697] F-5: DOWSIL SH8400 FLUID (manufactured by Dow Toray Co., Ltd., silicone-based surfactant)
[0698] (Additive)
[0699] G-1: Compound with the following structure (ultraviolet absorber)
[0700] [Chemical formula 57]
[0701]
[0702] G-2: Compound with the following structure (compound with epoxy group, weight average molecular weight 3500)
[0703] [Chemical formula 58]
[0704]
[0705] G-3: EHPE3150 (an adduct of 1,2-epoxy-4-(2-oxiranyl)cyclohexane with 2,2'-bis(hydroxymethyl)-1-butanol, manufactured by Daicel Corporation)
[0706] G-4: A compound having the following structure (a silane coupling agent)
[0707] [Chemical Formula 59]
[0708]
[0709] G-5: 3-methacryloxypropyltrimethoxysilane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd., a silane coupling agent)
[0710] G-6: p-methoxyphenol (a polymerization inhibitor)
[0711] G-7: Adekastab AO-80 (manufactured by ADEKA Corporation, an antioxidant)
[0712] (Solvent)
[0713] Z-1: Propylene glycol monomethyl ether acetate (PGMEA)
[0714] Z-2: Propylene glycol monomethyl ether (PGME)
[0715] Z-3: Cyclopentanone
[0716] Z-4: Cyclohexanone
[0717] Z-5: Anisole
[0718] Z-6: Diacetone alcohol
[0719] [Lightfastness evaluation]
[0720] The colored compositions of the examples and comparative examples described in the above table were coated on a glass substrate by spin coating. Then, a heat treatment (pre-baking) was performed at 100 °C for 120 seconds using a hot plate. Then, irradiation was carried out with i-rays at 1000 mJ / cm 2Exposure was carried out with the exposure amount, and then heating was performed at 200 °C for 5 minutes, thereby producing a film with a thickness of 0.6 μm. Regarding the obtained film, the transmittance (transmission rate) in the wavelength range of 400 to 700 nm was measured using MCPD-3000 manufactured by OTSUKA ELECTRONICS Co., LTD. Subsequently, using a lightfastness tester (Super Xenon WeatherMeter SX75, manufactured by Suga Test Instruments Co., Ltd.), light of 100,000 Lux was irradiated onto the film produced above for 2000 hours (total irradiation amount: 200 million Lux·hr). The transmittance of the film after light irradiation was measured, and the lightfastness was evaluated according to the following criteria.
[0721] A: The integrated value of the transmittance of the film after light irradiation in the wavelength range of 400 to 700 nm is 98% or more of the integrated value of the transmittance of the film before light irradiation in the wavelength range of 400 to 700 nm.
[0722] B: The integrated value of the transmittance of the film after light irradiation in the wavelength range of 400 to 700 nm is 95% or more and less than 98% of the integrated value of the transmittance of the film before light irradiation in the wavelength range of 400 to 700 nm.
[0723] C: The integrated value of the transmittance of the film after light irradiation in the wavelength range of 400 to 700 nm is 93% or more and less than 95% of the integrated value of the transmittance of the film before light irradiation in the wavelength range of 400 to 700 nm.
[0724] D: The integrated value of the transmittance of the film after light irradiation in the wavelength range of 400 to 700 nm is 90% or more and less than 93% of the integrated value of the transmittance of the film before light irradiation in the wavelength range of 400 to 700 nm.
[0725] E: The integrated value of the transmittance of the film after light irradiation in the wavelength range of 400 to 700 nm is less than 90% of the integrated value of the transmittance of the film before light irradiation in the wavelength range of 400 to 700 nm.
[0726] [Storage stability]
[0727] The viscosities of the coloring compositions of the examples and comparative examples described in the above table were measured immediately after production. After storing the coloring compositions with measured viscosities in a constant temperature bath at 45 °C for 72 hours, the viscosities were measured. In addition, the temperature of the coloring compositions was adjusted to 23 °C to measure the viscosities. The viscosity increase rate was calculated from the following formula, and the storage stability was evaluated.
[0728] Viscosity increase rate (%) = ((viscosity of the coloring composition after storing in a constant temperature bath at 45 °C for 72 hours / viscosity of the coloring composition immediately after production) - 1) × 100
[0729] A: The tackifying rate of the coloring composition is 5% or less.
[0730] B: The tackifying rate of the coloring composition exceeds 5% and is 7.5% or less.
[0731] C: The tackifying rate of the coloring composition exceeds 7.5% and is 10% or less.
[0732] D: The tackifying rate of the coloring composition exceeds 10%.
[0733] [Table 46]
[0734]
[0735] [Table 47]
[0736]
[0737] [Table 48]
[0738]
[0739] [Table 49]
[0740] Light resistance Storage stability Example 181 B B Example 182 B B Example 183 A B Example 184 A B Example 185 A B Example 186 A B Example 187 A B Example 188 A B Example 189 A B Example 190 A B Example 191 A B Example 192 A B Example 193 A B Example 194 A B Comparative Example 1 D D Comparative Example 2 E D
[0741] As shown in the above table, the coloring composition of the example can form a film with excellent light resistance.
[0742] In Example 1, as a result of conducting the evaluation in the same manner except for the surfactant, the result was the same as that of Example 1. By using the film obtained from the coloring composition of the example, a filter, a solid-state imaging device, and an image display device with excellent light resistance can be obtained.
Claims
1. A coloring composition comprising a colorant and a resin, The colorant contains a compound Y in which a compound represented by the formula (1) is coordinated to a metal atom, In formula (1), R 1 represents a hydrogen atom, an alkyl group or an aryl group, X 2 ~X 9 each independently represents a nitrogen atom, CH or CR x ,X 2 ~X 9 at least one of which is CR x , Among X 2 ~X 9 when two adjacent ones are CR x in the case, the two adjacent CR x R x optionally bond to each other to form a ring Among them, The formula (1) satisfies the following requirement 3, Requirement 3: X 6 ~X 8 Two adjacent ones among them are CR x and two adjacent CR x 's R x are bonded to each other to form a ring, and R x the ring formed by bonding to each other is a benzene ring or a naphthalene ring, and X 2 ~X 5 at least one of them is CR x and at least one of the CR 2 ~X 5 in X x 's R x represents nitro, cyano, -NR 101 R 102 , -OR 103 , -SR 104 , -COOR 105 , -OCOR 106 , -SO2R 107 , -SO2NR 108 R 109 , -SO2OR 110 , -CONR 111 R 112 or -NR 113 COR 114 , and R 101 and R 102 each independently represents a hydrogen atom, an alkyl group or an aryl group, and R 101 and R 102 optionally bond to each other to form a ring, and R 103 ~R 114 each independently represents an alkyl group or an aryl group.
2. The coloring composition according to claim 1, wherein, The metal atom is a copper atom or a zinc atom.
3. The coloring composition according to claim 1 or 2, wherein, The metal atom is a copper atom.
4. The coloring composition according to claim 1 or 2, wherein, The maximum absorption wavelength of the compound Y is in the range of 400 nm to 700 nm.
5. The coloring composition according to claim 1 or 2, wherein, The colorant further contains a green colorant.
6. The coloring composition according to claim 1 or 2, further comprising a polymerizable compound and a photoinitiator.
7. The coloring composition according to claim 1 or 2, which is used for a color filter or for an infrared transmission filter.
8. A film obtained from the coloring composition according to claim 1 or 2.
9. A light filter having the film according to claim 8.
10. A solid-state imaging device having the film according to claim 8.
11. An image display device having the film according to claim 8.
12. A compound in which a compound represented by the formula (1) is coordinated to a metal atom, In formula (1), R 1 represents a hydrogen atom, an alkyl group or an aryl group, X 2 ~X 9 each independently represents a nitrogen atom, CH or CR x ,X 2 ~X 9 at least one of which is CR x , Among X 2 ~X 9 wherein two adjacent ones are CR x In the case where two adjacent CRs x The R of x Optionally bond to each other to form a ring, Among them, The formula (1) satisfies the following requirement 3, Requirement 3: X 6 ~X 8 Two adjacent ones among them are CR x and two adjacent CR x The R of x are bonded to each other to form a ring, and the ring formed by the bonding of R x to each other is a benzene ring or a naphthalene ring, and at least one of X 2 ~X 5 is CR x and the R in the CR of at least one of X 2 ~X 5 represents nitro, cyano, -NR x R x -OR 101 R 102 -SR 103 -COOR 104 -OCOR 105 -SO2R 106 -SO2NR 107 R 108 -SO2OR 109 -CONR 110 R 111 or -NR 112 COR 113 R 114 and R 101 and R 102 each independently represents a hydrogen atom, an alkyl group or an aryl group, and R 101 and R 102 are optionally bonded to each other to form a ring, and R 103 ~R 114 each independently represents an alkyl group or an aryl group.
Citation Information
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