CN116848199A - Coloring composition, film, optical filter, solid-state imaging element, image display device, and compound - Google Patents

Coloring composition, film, optical filter, solid-state imaging element, image display device, and compound Download PDF

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Publication number
CN116848199A
CN116848199A CN202280010528.XA CN202280010528A CN116848199A CN 116848199 A CN116848199 A CN 116848199A CN 202280010528 A CN202280010528 A CN 202280010528A CN 116848199 A CN116848199 A CN 116848199A
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Prior art keywords
group
compound
formula
coloring composition
ring
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Inventor
古山英知
鹤田拓也
安原祐一
金子祐士
大谷贵洋
川岛敬史
西信哉
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Fujifilm Corp
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Fujifilm Corp
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Priority claimed from PCT/JP2022/003236 external-priority patent/WO2022168741A1/en
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Abstract

The invention provides a coloring composition, which comprises a colorant and a resin, wherein the colorant comprises a compound Y coordinated with a compound represented by a formula (1) on a metal atom. The invention also provides a film, a filter, a solid-state imaging element and an image display device using the coloring composition. The invention also provides a method for coordinating a metal atom with a metal atomA compound represented by the formula (1).

Description

Coloring composition, film, optical filter, solid-state imaging element, image display device, and compound
Technical Field
The present invention relates to a coloring composition comprising a colorant. The present invention also relates to a film, a filter, a solid-state imaging element, and an image display device each using the coloring composition. The present invention also relates to a methine azo metal complex compound.
Background
In recent years, with the popularization of digital cameras, camera-equipped mobile phones, and the like, the demand for solid-state imaging devices such as charge-coupled device (CCD) image sensors has increased greatly. As a key device for a display or an optical element, a color filter is used. The color filter generally has pixels of 3 primary colors of red, green, and blue, and functions to decompose transmitted light into 3 primary colors.
Colored pixels of respective colors of the color filter are manufactured using a coloring composition including a colorant. Patent document 1 describes a pigment composition for color filters, which contains a phthalocyanine pigment and a methine azo copper complex pigment, wherein the mass ratio of the phthalocyanine pigment to the methine azo copper complex pigment is 99.9/0.1 to 96.5/3.5.
Technical literature of the prior art
Patent literature
Patent document 1: international publication No. 2019/022051
Disclosure of Invention
Technical problem to be solved by the invention
In recent years, a film formed using a coloring composition containing a colorant is required to be further improved in light resistance.
Here, in patent document 1, pigment yellow 129 of color index (c.i.) is used as a methine azo copper complex-based pigment. C.i. pigment yellow 129 is a compound having the structure shown below. According to the studies by the present inventors, it was found that the film obtained using the composition containing the copper methine azo complex-based pigment described in the example of patent document 1 is insufficient in light resistance and has room for improvement.
[ chemical formula 1]
Accordingly, an object of the present invention is to provide a coloring composition capable of forming a film excellent in light resistance. Another object of the present invention is to provide a film, a filter, a solid-state imaging element, an image display device, and a compound.
Means for solving the technical problems
According to the studies of the present inventors, it has been found that the above object can be achieved by a coloring composition described later, and the present invention has been completed. Thus, the present invention provides the following.
<1> a coloring composition comprising a colorant and a resin, wherein the colorant comprises a compound Y in which a compound represented by the formula (1) is coordinated to a metal atom,
[ chemical formula 2]
In the 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 ，
R x Represents a substituent group, and is represented by,
at X 2 ～X 9 Wherein 2 adjacent ones are CR x In the case of (2) CR's adjacent to each other x R of (2) x Can be bonded to each other to form a ring,
wherein the formula (1) satisfies any of the following conditions 1 to 4,
requirement 1X 3 ～X 5 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 2X 2 And X 3 Is CR (CR) x And X is 2 Represented CR x R of (2) x And X is 3 Represented CR x R of (2) x And are bonded to form a heterocyclic ring,
requirement 3X 6 ～X 9 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 4X 2 X is X 3 At least one of them is CH and X 2 ～X 9 At least one of them is CR x 。
<2> the coloring composition according to <1>, wherein,
x of the above formula (1) 6 ～X 9 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Bonded to each other to form a ring.
<3> the coloring composition according to <1> or <2>, wherein,
x of the above formula (1) 2 ～X 9 At least one of them is CR x ，R x Is a heteroatom-containing group.
<4> the coloring composition according to any one of <1> to <3>, wherein,
x of the above formula (1) 2 ～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 、-SO 2 R 107 、-SO 2 NR 108 R 109 、-SO 2 OR 110 、-CONR 111 R 112 or-NR 113 COR 114 ，R 101 R is R 102 Each independently represents a hydrogen atom, an alkyl group or an aryl group, R 101 And R is R 102 Can be bonded to form a ring, R 103 ～R 114 Each independently represents an alkyl group or an aryl group.
<5> the coloring composition according to any one of <1> to <4>, wherein,
the metal atom is a copper atom or a zinc atom.
<6> the coloring composition according to any one of <1> to <4>, wherein,
the metal atom is a copper atom.
<7> the coloring composition according to any one of <1> to <6>, wherein,
the maximum absorption wavelength of the compound Y is in the range of 400 to 700 nm.
<8> the coloring composition according to any one of <1> to <7>, wherein,
the above-mentioned colorant further comprises a green colorant.
<9> the coloring composition according to any one of <1> to <8>, further comprising a polymerizable compound and a photopolymerization initiator.
<10> the coloring composition according to any one of <1> to <9>, which is used for a color filter or for an infrared ray transmission filter.
<11> a film obtained from the coloring composition according to any one of <1> to <10 >.
<12> an optical filter having the film of <11 >.
<13> a solid-state imaging device having the film of <11 >.
<14> an image display device having the film of <11 >.
<15> a compound in which a compound represented by the formula (1) is coordinated to a metal atom,
[ chemical formula 3]
In the 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 ，
R x Represents a substituent group, and is represented by,
at X 2 ～X 9 Wherein 2 adjacent ones are CR x In the case of (2) CR's adjacent to each other x R of (2) x Can be bonded to each other to form a ring,
wherein the formula (1) satisfies any of the following conditions 1 to 4,
requirement 1X 3 ～X 5 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 2X 2 And X 3 Is CR (CR) x And X is 2 Represented CR x R of (2) x And X is 3 Represented CR x R of (2) x And are bonded to form a heterocyclic ring,
requirement 3X 6 ～X 9 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 4X 2 X is X 3 At least one of them is CH and X 2 ～X 9 At least one of them is CR x 。
Effects of the invention
According to the present invention, a coloring composition capable of forming a film excellent in light resistance can be provided. Further, a film, a filter, a solid-state imaging element, an image display device, and a compound can be provided.
Detailed Description
The following describes the present invention in detail.
In the present specification, "to" is used in a meaning including numerical values described before and after the "to" as a lower limit value and an upper limit value.
In the labeling of groups (radicals) in the present specification, the label which is not labeled with a substituted or unsubstituted includes a group (radical) having no substituent, and also includes a group (radical) having a substituent. For example, "alkyl" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
In the present specification, "exposure" includes exposure using light, and drawing using a particle beam such as an electron beam or an ion beam is also included in exposure unless otherwise specified. Examples of the light used for exposure include an open spectrum of a mercury lamp, extreme ultraviolet rays typified by excimer laser, extreme ultraviolet rays (EUV light), actinic rays such as X-rays and electron beams, and radiation.
In the present specification, "(meth) acrylate" means either or both of acrylate and methacrylate, "(meth) acrylic acid" means either or both of acrylic acid and methacrylic acid, and "(meth) acryl" means either or both of acryl and methacryl.
In the present specification, me in the structural formula represents methyl, et represents ethyl, bu represents butyl, and Ph represents phenyl.
In the present specification, the weight average molecular weight and the number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
In the present specification, the total solid component refers to the total mass of components from which the solvent is removed from all components of the composition.
In the present specification, the pigment means a coloring material which is not easily dissolved in a solvent.
In the present specification, the term "process" includes not only an independent process but also a process that is not clearly distinguished from other processes, and is included in the term as long as the intended function of the process is exhibited.
< coloring composition >
The coloring composition of the present invention comprises a colorant and a resin, and is characterized in that the colorant comprises a compound Y in which a compound represented by formula (1) is coordinated to a metal atom.
According to the coloring composition of the present invention, a film excellent in light resistance can be formed. The detailed reason why such an effect can be obtained is not clear, but it is presumed as follows. Since the compound Y used as a colorant in the coloring composition of the present invention is likely to form an association in a film and is capable of effectively moving electrons between molecules, it is presumed that a film excellent in light resistance can be formed by using the coloring composition of the present invention.
The coloring composition of the present invention can be preferably used as a coloring composition for a color filter or an infrared ray transmission filter. More specifically, the composition can be preferably used as a coloring composition for forming a pixel 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 a pixel of a color filter. Examples of the type of the pixel include a red pixel, a green pixel, a blue pixel, a magenta pixel, a cyan pixel, a yellow pixel, and the like, and the pixel is preferably a red pixel, a green pixel, and a yellow pixel, more preferably a red pixel or a green pixel, and further preferably a green pixel.
When a film having a thickness of 0.65 μm is formed using the coloring composition of the present invention, the light transmittance of the film is preferably in the wavelength range of 470 to 520nm, more preferably in the wavelength range of 475 to 520nm, and even more preferably in the wavelength range of 480 to 520 nm. The light transmittance is preferably 50% in the wavelength range of 470 to 520nm and 575 to 625nm, respectively. In this embodiment, the wavelength on the short wavelength side at which the transmittance becomes 50% is preferably present in the wavelength range of 475 to 520nm, and more preferably in the wavelength range of 480 to 520 nm. The wavelength on the long wavelength side at which the transmittance is 50% is preferably in the wavelength range of 580 to 620nm, and more preferably 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 green pixel formation of a color filter.
The components used in the coloring composition of the present invention will be described below.
Colorant(s)
The coloring composition of the present invention contains a colorant. As the colorant, a compound Y containing a compound represented by formula (1) coordinated to a metal atom can be used. The compound Y is a methine azo metal complex. Compound Y is also a compound of the invention.
[ chemical formula 4]
In the 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 ，
R x Represents a substituent group, and is represented by,
at X 2 ～X 9 Wherein 2 adjacent ones are CR x In the case of (2) CR's adjacent to each other x R of (2) x Can be bonded to each other to form a ring,
wherein the formula (1) satisfies any of the following conditions 1 to 4,
requirement 1X 3 ～X 5 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 2X 2 And X 3 Is CR (CR) x And X is 2 Represented CR x R of (2) x And X is 3 Represented CR x R of (2) x And are bonded to form a heterocyclic ring,
requirement 3X 6 ～X 9 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 4X 2 X is X 3 At least one of them is CH and X 2 ～X 9 At least one of them is CR x 。
R of formula (1) 1 The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 15, and still more preferably 1 to 8. The alkyl group may be any of linear, branched, and cyclic, and is preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. Examples of the substituent include substituent T described below.
R of 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. Examples of the substituent include substituent T described below.
R of formula (1) 1 Preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.
X of formula (1) 2 ～X 9 Each independently represents a nitrogen atom, CH or CR x ，R x Represents a substituent. As R x Examples of the substituent include substituent T described below. R is R x The substituent represented is preferably a group containing a heteroatom, more preferably a specific functional group a described later. X of formula (1) 2 ～X 9 Preferably each independently represents CH or CR x . Also, X of formula (1) is preferable from the viewpoint of enabling formation of a film having more excellent light resistance 2 ～X 9 At least one of them is CR x ，R x Is a group containing a heteroatom (preferably a specific functional group a described below).
Specific functional groups A include nitro, cyano and-NR 101 R 102 、-OR 103 、-SR 104 、-COOR 105 、-OCOR 106 、-SO 2 R 107 、-SO 2 NR 108 R 109 、-SO 2 OR 110 、-CONR 111 R 112 -NR 113 COR 114 Preferably nitro, cyano, -NR 101 R 102 、-OR 103 、-SR 104 -C00R 105 More preferably-NR 101 R 102 -OR 103 。R 101 R is R 102 Each independently represents a hydrogen atom or an alkyl groupOr aryl, R 101 And R is R 102 Can be bonded to form a ring, R 103 ～R 114 Each independently represents an alkyl group or an aryl group.
R 101 ～R 114 The number of carbon atoms of the alkyl group represented is preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, particularly preferably 1 or 2. The alkyl group may be any of linear, branched, and cyclic, and is preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. Examples of the substituent include substituent T described below. R is R 101 ～R 114 The alkyl group represented is preferably methyl or ethyl.
R 101 ～R 114 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. Examples of the substituent include substituent T described below.
R 101 R is R 102 Each independently is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom, a methyl group or an ethyl group. R is R 103 ～R 114 Each independently is preferably an alkyl group, more preferably a methyl or ethyl group.
X in formula (1) 2 ～X 9 Wherein 2 adjacent ones are CR x In the case of (2) CR's adjacent to each other x R of (2) x May be bonded to each other to form a ring. The ring formed may be a hydrocarbon ring or a heterocyclic ring. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. Examples of the hetero atom contained in the heterocyclic ring include a nitrogen atom, a sulfur atom and an oxygen atom. The heterocyclic ring is a 5-membered ring or a 6-membered ring, preferably. Specific examples of the ring to be formed include a hydrocarbon ring such as a benzene ring, a naphthalene ring, 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 tetrahydrofuran ring, a tetrahydropyran ring, a tetrahydrothiophene ring, and a tetrahydrothiopyran ring. Upper part The ring formed may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
Equation (1) satisfies any of the above-described requirements 1 to 4.
The requirement 1 is as follows: x is X 3 ～X 5 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Bonded to each other to form a ring. As R x Examples of the ring bonded to each other include the above-mentioned ring, preferably a benzene ring or naphthalene ring, and more preferably a benzene ring. R is R x The rings bonded to each other may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
Specific examples of the element 1 include X 3 And X 4 Each independently CR x And X is 3 Represented CR x R of (2) x And X is 4 Represented CR x R of (2) x Bonding to form a ring, X 4 And X 5 Each independently CR x And X is 4 Represented CR x R of (2) x And X is 5 Represented CR x R of (2) x Bonding to form a ring.
In element 1, X is also preferable 6 ～X 9 At least one of them is CR x And R is x Is a heteroatom-containing group (preferably the specific functional group a described above).
The requirement 2 is as follows: x is X 2 And X 3 Is CR (CR) x And X is 2 Represented CR x R of (2) x And X is 3 Represented CR x R of (2) x Bonding to form a heterocycle. As R x Examples of the heterocycle bonded to each other include the above-mentioned heterocycle. R is R x The heterocyclic ring formed by bonding to each other may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
Essential element2, X is also preferred 6 ～X 9 At least one of them is CR x And R is x Is a heteroatom-containing group (preferably the specific functional group a described above).
The requirement 3 is as follows: x is X 6 ～X 9 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Bonded to each other to form a ring. As R x Examples of the ring bonded to each other include the above-mentioned ring, preferably a benzene ring or naphthalene ring, and more preferably a benzene ring. R is R x The rings bonded to each other may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
Specific examples of the element 3 include X 6 And X 7 Each independently CR x And X is 6 Represented CR x R of (2) x And X is 7 Represented CR x R of (2) x Bonding to form a ring, X 7 And X 8 Each independently CR x And X is 7 Represented CR x R of (2) x And X is 8 Represented CR x R of (2) x Bonding to form a ring, X 8 And X 9 Each independently CR x And X is 8 Represented CR x R of (2) x And X is 9 Represented CR x R of (2) x The form of bonding to form a ring is preferably X from the viewpoint of enabling formation of a film having more excellent light resistance 6 And X 7 Each independently CR x And X is 6 Represented CR x R of (2) x And X is 7 Represented CR x R of (2) x Bonding to form a ring or X 7 And X 8 Each independently CR x And X is 7 Represented CR x R of (2) x And X is 8 Represented CR x R of (2) x The bonding to form a ring is more preferably X 7 And X 8 Each independently CR x And X is 7 Represented CR x R of (2) x And X is 8 Represented CR x R of (2) x BondingAnd forms a ring.
In element 3, at X 2 ～X 5 Wherein 2 adjacent ones are CR x In the case of (2) CR's adjacent to each other x R of (2) x May be bonded to each other to form a ring. As R x Examples of the ring bonded to each other include the above-mentioned ring, preferably a benzene ring or naphthalene ring, and more preferably a benzene ring. R is R x The rings bonded to each other may have a substituent. Examples of the substituent include a substituent butyl described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
In element 3, X is also preferable 2 ～X 5 At least one of them is CR x And R is x Is a heteroatom-containing group (preferably the specific functional group a described above).
The requirement 4 is as follows: x is X 2 X is X 3 At least one of them is CH and X 2 ～X 9 At least one of them is CR x 。R x Represents a substituent. In element 4, X is preferable 2 ～X 9 1 to 4 CR in (B) x More preferably 1 or 2 are CR x . As R x Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
The expression (1) preferably satisfies any of the above-described requirements 1, 3, or 4, more preferably satisfies the requirements 3 or 4, and even more preferably satisfies the requirements 3.
The compound represented by the formula (1) is preferably a compound represented by the formula (1-1).
[ chemical formula 5]
In the formula (1-1), R 1 Represents a hydrogen atom, an alkyl group or an aryl group,
R 2 ～R 9 each independently represents a hydrogen atom or a substituent,
R 2 ～R 9 can be bonded to form a ring;
wherein the formula (1-1) satisfies any of the following requirements 1a to 4 a;
requirement 1a R 3 ～R 5 Is bonded to form a ring;
requirement 2a R 2 And R is R 3 Bonding to form a heterocycle;
requirement 3a R 6 ～R 9 Is bonded to form a ring;
requirement 4a R 2 R is R 3 At least one of which is a hydrogen atom and R 2 ～R 9 At least one of which is a substituent.
R of formula (1-1) 1 Meaning of (A) and R of formula (1) 1 Meaning the same.
R as formula (1-1) 2 ～R 9 The substituent represented by the above-mentioned substituent T is preferably a group containing a heteroatom, more preferably the above-mentioned specific functional group a.
In the formula (1-1), R 2 ～R 9 Can be bonded to form a ring. The ring formed may be the ring described above. The ring formed above may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
The formula (1-1) satisfies any of the above-described requirements 1a to 4 a.
The requirement 1a is as follows: r is R 3 ～R 5 Is bonded to form a ring. The ring to be formed is preferably a benzene ring or naphthalene ring, more preferably a benzene ring. The ring formed above may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
Specific examples of the element 1a include R 3 And R is R 4 Bonding to form a ring, R 4 And R is R 5 Bonding to form a ring.
In the element 1a of the present invention,also preferred is R 6 ～R 9 At least one of which is a heteroatom-containing group (preferably the specific functional group a described above).
The requirement 2a is as follows: r is R 2 And R is R 3 Bonding to form a heterocycle. Examples of the heterocycle include the heterocycles described above. The heterocyclic ring formed above may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
In element 2a, R is also preferable 6 ～R 9 At least one of which is a heteroatom-containing group (preferably the specific functional group a described above).
The requirement 3a is as follows: r is R 6 ～R 9 Is bonded to form a ring. The ring to be formed is preferably a benzene ring or naphthalene ring, more preferably a benzene ring. The ring formed above may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
Specific examples of the element 3a include R 6 And R is R 7 Bonding to form a ring, R 7 And R is R 8 Bonding to form a ring, R 8 And R is R 9 The bonding method to form a ring is preferably R from the viewpoint of forming a film having more excellent light resistance 6 And R is R 7 Bonding to form a ring or R 7 And R is R 8 The bonding to form a ring is more preferably R 7 And R is R 8 Bonding to form a ring.
In element 3a, R 2 ～R 5 Can be bonded to form a ring. The ring formed above may be the ring described above, and the benzene ring or naphthalene ring is preferably a benzene ring, and more preferably a benzene ring. The ring formed above may have a substituent. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
In element 3a, R is also preferable 2 ～R 5 In (a) and (b)At least one of which is a heteroatom-containing group (preferably the specific functional group a described above).
The requirement 4a is as follows: r is R 2 R is R 3 At least one of which is a hydrogen atom and R 2 ～R 9 At least one of which is a substituent. Among the elements 4a, R is preferable 2 ～R 9 1 to 4 of the substituents are more preferably 1 or 2 substituents. Examples of the substituent include substituent T described below. The substituent is preferably a heteroatom-containing group, more preferably the specific functional group a described above.
Equation (1-1) preferably satisfies any of the above-described requirements 1a, 3a, or 4a, more preferably satisfies requirement 3a or 4a, and even more preferably satisfies requirement 3a.
In the compound Y, the metal atom coordinated by the compound represented by the formula (1) may be a copper atom, a zinc atom, an iron atom, a titanium atom, an aluminum atom, a tin atom, a magnesium atom, a chromium atom, a calcium atom, or a silicon atom, and is preferably a copper atom or a zinc atom, and more preferably a copper atom. The compound Y may be coordinated to 1 or more than 2 compounds represented by the formula (1) on the metal atom. Further, a ligand other than the compound represented by the formula (1) may be coordinated to the metal atom. Examples of the ligand include heterocyclic compounds (e.g., pyridine, pyrimidine, imidazole, pyrazole, triazole, tetrazole, quinoline, 1, 10-phenanthroline, etc.), protic compounds (e.g., water, methanol, ethanol, etc.), amine compounds (e.g., triethylamine, N, N, N ', N ' -tetramethylenediamine, ethylenediamine tetraacetic acid N, N ', N "-pentamethyldiethylenetriamine, etc.), amide compounds (for example, N-dimethylacetamide, N-methylpyrrolidone, etc.), dimethylsulfoxide, sulfolane, nitrile compounds (for example, acetonitrile, etc.), etc. And, the compound Y may be a dinuclear complex. When the compound represented by the formula (1) is coordinated to a metal atom, examples of the compound Y include a compound represented by the following formula (1-1), a compound represented by the formula (1-2), a compound represented by the formula (1-3), and a compound represented by the formula (1-4). In the following formula, M 1 ～M 5 Each independently represents a metal atom. And, compoundingThe compound Y may be a compound in which a ligand is 1:3 to a metal atom, a compound in which a ligand is 1:4 to a metal atom, a compound in which a ligand is 2:3 to a metal atom, or a compound in which a ligand is 3:3 to a metal atom. Also, a part of the ligand may deviate from the metal atom or a compound other than the ligand may coordinate with the metal atom.
[ chemical formula 6]
(substituent T)
Examples of the substituent T include the following. Halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (preferably alkyl group having 1 to 30 carbon atoms), alkenyl group (preferably alkenyl group having 2 to 30 carbon atoms), alkynyl group (preferably alkynyl group having 2 to 30 carbon atoms), aryl group (preferably aryl group having 6 to 30 carbon atoms), heterocyclic group (preferably heterocyclic group having 1 to 30 carbon atoms), amino group (preferably amino group having 0 to 30 carbon atoms), alkoxy group (preferably alkoxy group having 1 to 30 carbon atoms), aryloxy group (preferably aryloxy group having 6 to 30 carbon atoms), heterocyclic oxy group (preferably heterocyclic group having 1 to 30 carbon atoms), acyl group (preferably acyl group having 2 to 30 carbon atoms), alkoxycarbonyl group (preferably alkoxycarbonyl group having 2 to 30 carbon atoms), aryloxy carbonyl group (preferably aryloxy carbonyl group having 7 to 30 carbon atoms), heterocyclic oxycarbonyl group (preferably heterocyclic carbonyl group having 2 to 30 carbon atoms), acyloxy group (preferably acyloxy group having 2 to 30 carbon atoms), sulfamoyl group (preferably sulfamoyl group having 0 to 30 carbon atoms), aminocarbonyl group having 0 to 30 carbon atoms Sulfamoylamino group (preferably sulfamoylamino group having 0 to 30 carbon atoms), carbamoyl group (preferably carbamoyl group having 1 to 30 carbon atoms), alkylthio group (preferably alkylthio group having 1 to 30 carbon atoms), arylthio group (preferably arylthio group having 6 to 30 carbon atoms), heterocyclic thio group (preferably heterocyclic thio group having 1 to 30 carbon atoms), alkylsulfonyl group (preferably alkylsulfonyl group having 1 to 30 carbon atoms), alkylsulfonylamino group (preferably alkylsulfonylamino group having 1 to 30 carbon atoms), arylsulfonyl group (preferably arylsulfonyl group having 6 to 30 carbon atoms), arylsulfonylamino group (preferably arylsulfonylamino group having 6 to 30 carbon atoms), heterocyclic sulfonyl group (preferably heterocyclic sulfonyl group having 1 to 30 carbon atoms), and heterocyclosulfonylamino (preferably a heterocyclosulfonylamino group having 1 to 30 carbon atoms), alkylsulfinyl (preferably an alkylsulfinyl group having 1 to 30 carbon atoms), arylsulfinyl (preferably an arylsulfinyl group having 6 to 30 carbon atoms), heterocyclosulfonyl (preferably a heterocyclosulfonyl group having 1 to 30 carbon atoms), ureido (preferably a ureido group having 1 to 30 carbon atoms), hydroxy, nitro, carboxyl, sulfo, phosphoric acid, carboxylic acid amide, sulfonamide, imide, phosphino, mercapto, cyano, alkylsulfinyl, arylsulfinyl, arylazo, heterocycloazo, phosphino, phosphinyloxy, phosphinylamino, silyl, hydrazino, heterocyclic azo, phosphinyloxy, phosphinylamino, silyl, phosphinyl, an imino group. In the case where these groups are groups which can be substituted, a substituent may be further contained.
The compound Y may be a pigment or a dye.
The maximum absorption wavelength of the compound Y is preferably in the range of 400 to 700nm, more preferably in the range of 400 to 600 nm.
Specific examples of the compound Y include the compounds (Y-1) to (Y-87) described in examples described below.
The colorant contained in the coloring composition of the present invention may further contain a colorant other than the above-mentioned compound Y. Examples of the other colorants used in combination include a green colorant, a red colorant, a yellow colorant, a violet colorant, a blue colorant, a color colorant such as an orange colorant, a black colorant, and the like. The other colorant is preferably at least 1 selected from the group consisting of a green colorant, a red colorant, and an orange colorant, more preferably at least 1 selected from the group consisting of a green colorant and a red colorant, and still more preferably a green colorant. The other colorant may be a pigment or a dye, but is preferably a pigment. In the case of using a pigment as another colorant, association formation is easily promoted by interaction of the pigment as another colorant with the compound Y, and a film more excellent in light resistance can be formed. Among other effects, the effect is remarkable when a green pigment is used, and the most remarkable effect is exhibited when a phthalocyanine compound is used as a green pigment.
Examples of the red colorant include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, methine azo compounds, xanthene-pah compounds, quinacridone compounds, perylene compounds, thioindigo compounds, and the like, and diketopyrrolopyrrole compounds, anthraquinone compounds, and azo compounds are preferable, and diketopyrrolopyrrole compounds are more preferable, from the viewpoint of easy formation of a film having more excellent light resistance. And, the red colorant is preferably a pigment.
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, etc. Further, as the red colorant, a diketopyrrolopyrrole compound described in japanese patent application laid-open No. 2017-201384, a diketopyrrolopyrrole compound described in paragraphs 0016 to 0022 of japanese patent application laid-open No. 6248838, a diketopyrrolopyrrole compound described in international publication No. 2012/102399, a diketopyrrolopyrrole compound described in international publication No. 2012/117965, a diketopyrrolopyrrole bromide compound described in japanese patent application laid-open No. 2020-085947, a naphthol azo compound described in japanese patent application laid-open No. 2012-229344, a red colorant described in japanese patent application laid-open No. 6516119, a red colorant described in japanese patent application laid-open No. 6525101, a diketopyrrolopyrrole compound described in japanese patent application laid-open No. 2020-0909, a diketopyrrolopyrrole compound described in japanese patent application laid-open No. 10-2019-0741, a diketopyrrolopyrrole compound described in korean patent application laid-open No. 2012-1179-0741, a naphthol azo compound described in japanese patent application laid-open No. 2012-229344, a red colorant described in japanese patent application laid-open No. 01401402, a perylene laid-open No. 01402, and the like. As the red colorant, a compound having a structure in which an aromatic ring group obtained by introducing a group having an oxygen atom, a sulfur atom, or a nitrogen atom bonded thereto is bonded to a diketopyrrolopyrrole skeleton can also be used.
The red colorant is preferably c.i. pigment red 122, 177, 254, 255, 264, 269, 272, more preferably c.i. pigment red 254, 264, 272, and even more preferably c.i. pigment red 254, 264.
The green colorant includes a phthalocyanine compound, a squarylium compound, and the like, and is preferably a phthalocyanine compound from the viewpoint of easy formation of a film having more excellent light resistance. And, the green colorant is preferably a pigment.
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, and 66. Further, 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 in one molecule can be used. Specific examples thereof include compounds described in International publication No. 2015/118720. Further, as the green colorant, a compound described in the specification of chinese patent application No. 106909027, a phthalocyanine compound having a phosphate as a ligand described in international publication No. 2012/102395, a phthalocyanine compound described in japanese patent application laid-open No. 2019-008014, a phthalocyanine compound described in japanese patent application laid-open No. 2018-180023, a compound described in japanese patent application laid-open No. 2019-038958, an aluminum phthalocyanine compound described in japanese patent application laid-open No. 2020-070426, a core-shell type pigment described in japanese patent application laid-open No. 2020-076995, a diarylmethane compound described in japanese patent application laid-open No. 2020-504758, and the like can be used.
The green colorant is preferably c.i. pigment green 7, 36, 58, 62, 63, more preferably c.i. pigment green 36, 58.
Specific examples of the orange colorant include c.i. pigment orange 2, 5, 13, 16, 17: 1. 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc.
Examples of the yellow colorant include azo compounds, methine azo compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds. Specific examples of the yellow colorant include 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: 1. 36, 36: 1. 37, 37: 1. yellow pigments such as 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.
The nickel azo barbiturate complex having the following structure can also be used as the yellow colorant.
[ chemical formula 7]
And, as a yellow colorant, the compounds described in paragraph 0281 of International publication No. 2021/215133, the compounds described in Japanese patent application laid-open No. 2017-201003, the compounds described in Japanese patent application laid-open No. 2017-197719, the compounds described in paragraphs 0011 to 0062, 0137 to 0276, the compounds described in paragraphs 0010 to 0062, 0138 to 0295, the compounds described in paragraphs 0011 to 0062, 0139 to 0190, the compounds described in paragraphs 0017-171914, the compounds described in paragraphs 0010 to 0065, 0142 to 0222, the compounds described in paragraphs 0013-054339, the compounds described in paragraphs 0013 to 0018, the compounds described in paragraphs 0013 to 00528, the compounds described in Japanese patent application laid-open No. 2013-17139 isoindoline compound described in japanese patent application laid-open publication No. 2018-062644, quinophthalone compound described in japanese patent application laid-open publication No. 2018-203798, quinophthalone compound described in japanese patent application laid-open publication No. 2018-062578, quinophthalone compound described in japanese patent application laid-open publication No. 6432076, quinophthalone compound described in japanese patent application laid-open publication No. 2018-155881, quinophthalone compound described in japanese patent application laid-open publication No. 2018-111757, quinophthalone compound described in japanese patent application laid-open publication No. 2018-040835, quinophthalone compound described in japanese patent application laid-open publication No. 2017-197640, quinophthalone compound described in japanese patent application laid-open publication No. 2016-145282, quinophthalone compound described in japanese patent application laid-open publication No. 2014-085565, quinophthalone compound described in japanese patent application laid-open publication No. 2014-021139, quinophthalone compound described in japanese patent application laid-open publication No. 2013-209414, quinophthalone compound described in japanese patent application laid-open publication No. 2013-209455, quinophthalone compound described in japanese patent application laid-open publication No. 2013-181015, quinophthalone compound described in japanese patent application laid-open publication No. 2013-061622, quinophthalone compound described in japanese patent application laid-open publication No. 2013-03486, quinophthalone compound described in japanese patent application laid-open publication No. 2012-226110, quinophthalone compound described in japanese patent application laid-open publication No. 2008-074987, quinophthalone compound described in japanese patent application laid-open publication No. 2008-081565, quinophthalone compound described in japanese patent application laid-open publication No. 2008-074986, quinophthalone compound described in japanese patent application laid-open publication No. 2008-074985, quinophthalone compound described in japanese patent application laid-open publication No. 2008-050420, quinophthalone compound described in japanese patent application laid-open publication No. 2008-074985 quinophthalone compound described in japanese patent application laid-open publication No. 2008-031281, quinophthalone compound described in japanese patent application laid-open publication No. 48-032765, quinophthalone compound described in japanese patent application laid-open publication No. 2019-008014, quinophthalone compound described in japanese patent application laid-open publication No. 6607427, methine dye described in japanese patent application laid-open publication No. 2019-073695, methine dye described in japanese patent application laid-open publication No. 2019-073696, methine dye described in japanese patent application laid-open publication No. 2019-073697, methine dye described in japanese patent application laid-open publication No. 2019-073698, compounds described in korean patent application laid-open publication No. 10-2014-0034963, compounds described in japanese patent application laid-open publication No. 2017-095706, compounds described in taiwan area application laid-open publication No. 201920495, and, the compound described in japanese patent No. 6607427, the compound described in japanese patent application laid-open publication No. 2020-033525, the compound described in japanese patent application laid-open publication No. 2020-033524, the compound described in japanese patent application laid-open publication No. 2020-033523, the compound described in japanese patent application laid-open publication No. 2020-033522, the compound described in japanese patent application laid-open publication No. 2020-033521, the compound described in international publication No. 2020/045200, the compound described in international publication No. 2020/045199, the compound described in international publication No. 2020/045197, the azo compound described in japanese patent application laid-open publication No. 2020-093994, the perylene compound described in japanese patent application laid-open publication No. 2020-083982, the perylene compound described in international publication No. 2020/105346, the quinophthalone compound described in japanese patent publication No. 2020-517791, the compound represented by the following formula (QP) and the compound represented by the following formula (QP) 2. In addition, from the viewpoint of improving the color value, it is also preferable to use a compound obtained by multimerizing these compounds.
[ chemical formula 8]
In the formula (QP 1), X 1 ～X 16 Each independently represents a hydrogen atom or a halogen atom, Z 1 An alkylene group having 1 to 3 carbon atoms. Specific examples of the compound represented by the formula (QP 1) include a compound described in paragraph 0016 of japanese patent No. 6443711.
[ chemical formula 9]
In the formula (QP 2), Y 1 ～Y 3 Each independently represents a halogen atom. n and m represent integers of 0 to 6, and p represents an integer of 0 to 5. (n+m) is 1 or more. Specific examples of the compound represented by the formula (QP 2) include compounds described in paragraphs 0047 to 0048 of Japanese patent application publication No. 6432077.
Specific examples of the violet colorant include violet pigments such as c.i. pigment violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
Specific examples of the blue colorant include c.i. pigment blue 1, 2, 15, and 15: 1. 15: 2. 15: 3. 15: 4. 15: 6. 16, 22, 29, 60, 64, 66, 79, 80, 87, 88, etc. Further, an aluminum phthalocyanine compound having a phosphorus atom can be used as the blue colorant. Specific examples thereof include 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.
Further, as the color colorant, triarylmethane dye polymer described in Korean laid-open patent publication No. 10-2020-0028160, xanthene and pamphlet compound described in Japanese patent application laid-open No. 2020-117638, phthalocyanine compound described in International publication No. 2020/174991, isoindoline compound described in Japanese patent application laid-open No. 2020-160279, or salts thereof can be used.
Examples of the black colorant include dibenzofuranone compounds, methine azo compounds, perylene compounds, azo compounds, etc., and dibenzofuranone compounds and perylene compounds are preferable. Examples of the dibenzofuranone compound include compounds described in japanese patent application laid-open publication No. 2010-534726, japanese patent application laid-open publication No. 2012-515233, japanese patent application laid-open publication No. 2012-515234, and the like, and are available as "Irgaphor Black" manufactured by BASF corporation. Examples of the perylene compound include compounds described in paragraphs 0016 to 0020 of Japanese patent application laid-open No. 2017-226821, C.I.pigment Black 31, 32, and the like. Examples of the methine azo compound include compounds described in JP-A-01-170601 and JP-A-02-034664, and are available as "CHROMO F [ NE BLACK A1103 ] manufactured by Ltd.
The preferable diffraction angles of the various pigments can be described in Japanese patent publication No. 6561862, japanese patent publication No. 6413872, japanese patent publication No. 6281345, japanese patent application laid-open No. 2020-026503 and Japanese patent application laid-open No. 2020-033526, which are incorporated herein by reference. And is also preferable as a pyrrolopyrrole pigment, using a compound corresponding to X in 8 of the lattice planes (. + -. 1.+ -. 1) the crystallite size in the plane direction of the maximum peak in the ray diffraction pattern wasThe following are described below. Further, the physical properties of the pyrrolopyrrole-based pigment are also preferably set as described in paragraphs 0028 to 0073 of Japanese patent application laid-open No. 2020-097744.
The crystallite size obtained from the half-value width of a peak derived from any crystal plane in an X-ray diffraction spectrum when the CuK alpha ray of the pigment is used as an X-ray source is preferably 0.1nm to 100nm, more preferably 0.5nm to 50nm, still more preferably 1nm to 30nm, and particularly preferably 5nm to 25nm.
In the case where the coloring composition of the present invention contains a green colorant, it is preferable to use as a coloring composition for green pixel formation of a color filter. Further, in the case where the coloring composition of the present invention contains a red colorant, it is preferable to use the coloring composition as a coloring composition for forming a red pixel of a color filter.
Further, the colorant contained in the coloring composition contains 2 or more kinds of color colorants and black can be formed by a combination of 2 or more kinds of color colorants. Such a coloring composition can be preferably used as a coloring composition for infrared transmission filter formation. The following are examples of combinations of color colorants when black is formed from a combination of 2 or more kinds of color colorants.
(1) A red colorant, a blue colorant and a yellow colorant.
(2) A red colorant, a blue colorant, a yellow colorant, and a violet colorant.
(3) The color composition contains red, blue, yellow, violet and green colorants.
(4) And a red colorant, a blue colorant, a yellow colorant, and a green colorant.
(5) And a yellow colorant and a violet colorant.
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 mass% or less, more preferably 75 mass% or less, and still more preferably 70 mass% or less.
The content of the 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 may be set to 100 mass% or less, 95 mass% or less, or 90 mass% or less.
The content of the 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 mass% or less, more preferably 25 mass% or less, and still more preferably 20 mass% or less.
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 coloring composition containing a yellow coloring agent and a green coloring agent as the coloring agents. Further, the compound Y is preferably a yellow colorant. The mass ratio of the yellow colorant to the green colorant is preferably yellow colorant to green colorant=30:70 to 70:30, more preferably 30:70 to 60:40, still more preferably 30:70 to 50:50. The content of the compound Y is preferably 5 to 60 parts by mass per 100 parts by mass of the green colorant. 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.
When the coloring composition of the present invention is used as a coloring composition for forming a red pixel of a color filter, it is preferable to use a coloring composition containing a yellow coloring agent and a red coloring agent as the coloring agent. Further, the compound Y is preferably a yellow colorant. The mass ratio of the yellow colorant to the red colorant is preferably yellow colorant to red colorant=30:70 to 70:30, more preferably 30:70 to 60:40, still more preferably 30:70 to 50:50. The content of the compound Y is preferably 5 to 50 parts by mass per 100 parts by mass of the red colorant. 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.
When the coloring composition of the present invention is used as a coloring composition for forming yellow pixels 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. Further, the compound Y is preferably a yellow colorant. The content of the compound Y in the yellow colorant 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 may be set to 100 mass% or less, 95 mass% or less, or 90 mass% or less.
Resin
The coloring composition of the present invention comprises a resin. The resin is blended, for example, for the purpose of dispersing a pigment or the like in the coloring composition or for the purpose of a binder. In addition, a resin used mainly for dispersing pigments and the like in a coloring composition is referred to as a dispersant. However, such use of the resin is an example, and the resin may be used for other purposes than such use.
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.
Examples of the resin include (meth) acrylic resin, epoxy resin, (meth) acrylamide resin, alkene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyether sulfone resin, polystyrene resin, polyaryletherphosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, and silicone resin. And, as the resin, there is used, the resin described in the examples of International publication No. 2016/088645, the resin described in Japanese patent application laid-open No. 2017-057265, the resin described in Japanese patent application laid-open No. 2017-032585, the resin described in Japanese patent application laid-open No. 2017-075248, the resin described in Japanese patent application laid-open No. 2017-066240, the resin described in Japanese patent application laid-open No. 2017-167513, the resin described in Japanese patent application laid-open No. 2017-173787, the resin described in paragraphs 0041 to 0060 of Japanese patent application laid-open No. 2017-206689, the blocked polyisocyanate resin (cyclic resin) described in Japanese patent application laid-open No. 2016-222891, the resin described in Japanese patent application laid-open No. 2020-122052, the resin described in Japanese patent application laid-open No. 2020-111656, the resin described in Japanese patent application laid-open No. 2017-173789, the resin described in Japanese patent application laid-open No. 2017-206689, the resin described in Japanese patent application laid-open No. 2018-010856, the resin in the paragraph 2018-010856-5, and the resin having a side chain structure comprising a pendant unit formed on the main chain and a biphenyl unit formed on the main chain.
As the resin, a resin having an acid group is preferably used. Examples of the acid group include a carboxyl group, a phosphate group, a sulfonate group, and a phenolic hydroxyl group.
The acid value of the resin having an acid group is preferably 30 to 500mgKOH/g. The lower limit is more preferably 40mgKOH/g or more, particularly preferably 50mgKOH/g or more. The upper limit is more preferably 400mgKOH/g or less, still more preferably 300mgKOH/g or less, particularly preferably 200mgKOH/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. The number average molecular weight (Mn) of the resin having an acid group is preferably 1000 to 20000.
The resin having an acid group preferably contains a repeating unit having an acid group in a side chain, and more preferably contains 5 to 70 mol% of the repeating unit having an acid group in a side chain, out of all the repeating units of the resin. The upper limit of the content of the repeating unit 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 unit having an acid group in a side chain is preferably 10 mol% or more, more preferably 20 mol% or more.
Regarding the resin having an acid group, reference can be made to the description of paragraphs 0558 to 0571 of japanese patent application laid-open No. 2012-208494 (paragraphs 0685 to 0700 of the corresponding specification of japanese patent application laid-open No. 2012/0235099), and the description of paragraphs 0076 to 0099 of japanese patent application laid-open No. 2012-198408, which are incorporated herein by reference. Further, a commercially available resin having an acid group can be used. The method for introducing the acid group into the resin is not particularly limited, and examples thereof include the method described in japanese patent No. 6349629. Further, as a method for introducing an acid group into a resin, a method in which an acid anhydride is reacted with a hydroxyl group generated by a ring-opening reaction of an epoxy group to introduce an acid group can be mentioned.
The coloring composition of the present invention also preferably contains a resin having an alkaline group. The resin having a basic group is preferably a resin having a repeating unit having a basic group in a side chain, more preferably a copolymer having a repeating unit having a basic group in a side chain and a repeating unit not having a basic group, and still more preferably a block copolymer having a repeating unit having a basic group in a side chain and a repeating unit not having a basic group. Resins having basic groups can also be used as dispersants. The amine value of the resin having an alkaline group is preferably 5 to 300mgKOH/g. The lower limit is preferably 10mgKOH/g or more, more preferably 20mgKOH/g or more. The upper limit is preferably 200mgKOH/g or less, more preferably 100mgKOH/g or less.
Examples of the commercial products of the resin having a basic group include DISERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (BYK Co., LTD), SOLSPERSE11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (Lubrizol Japan Limited, inc.), efka PX 4300, 4330, 4046, 4060, 4080 (BASF Inc.), and the like. The resin having an alkali group may be a block copolymer (B) described in paragraphs 0063 to 0112 of Japanese patent application laid-open No. 2014-219665, a block copolymer A1 described in paragraphs 0046 to 0076 of Japanese patent application laid-open No. 2018-156021, or a vinyl resin having an alkali group described in paragraphs 0150 to 0153 of Japanese patent application laid-open No. 2019-184763, and these are incorporated herein by reference.
The coloring composition of the present invention also preferably contains a resin having an acid group and a resin having an alkali group, respectively. According to this aspect, the storage stability of the coloring composition can be further improved. When the resin having an acid group and the resin having an alkali group are used in combination, the content of the resin having an alkali group is preferably 20 to 500 parts by mass, more preferably 30 to 300 parts by mass, and even more preferably 50 to 200 parts by mass, relative to 100 parts by mass of the resin having an acid group.
As the resin, a resin containing a repeating unit derived from a monomer component including a compound represented by the following formula (EDl) and/or a compound represented by the following formula (ED 2) (hereinafter, these compounds may also be referred to as "ether dimers") is also preferably used.
[ chemical formula 10]
In the formula (ED 1), R 1 R is R 2 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
[ chemical formula 11]
In the formula (ED 2), R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. For details of formula (ED 2), reference can be made to the description of japanese patent application laid-open No. 2010-16889, which is incorporated herein.
Specific examples of the ether dimer include those described in paragraph 0317 of Japanese patent application laid-open No. 2013-029760, which is incorporated herein by reference.
As the resin, a resin containing a repeating unit derived from the compound represented by formula (X) is also preferably used.
[ chemical formula 12]
Wherein R is 1 Represents a hydrogen atom or a methyl group, R 21 R is R 22 Each independently represents an alkylene group, and n represents an integer of 0 to 15. R is R 21 R is R 22 The number of carbon atoms of the alkylene group represented is preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, particularly preferably 2 or 3.n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
Examples of the compound represented by the formula (X) include ethylene oxide or propylene oxide modified (meth) acrylic esters of p-cumylphenol. Examples of the commercially available products include ARONIX M-110 (TOAGOSEI CO., LTD.).
As the resin, a resin having a crosslinkable group is also preferably used. Examples of the crosslinkable group include an ethylenically unsaturated bond-containing group and a cyclic ether group.
Examples of the ethylenically unsaturated bond-containing group include vinyl, styryl, (meth) allyl, and (meth) acryl. Examples of the cyclic ether group include an epoxy group and an oxetanyl group, and an epoxy group is preferable. The epoxy group may be an alicyclic epoxy group. The alicyclic epoxy group is a functional group having a 1-valent ring structure in which an epoxy ring and a saturated hydrocarbon ring are condensed. The cyclic ether group is preferably at least 1 selected from the group represented by the formula (e-1) and the group represented by the formula (e-2), more preferably the group represented by the formula (e-2). In the case where n of the formula (e-1) is 0, the group represented by the formula (e-1) is an epoxy group, and in the case where n is 1, the group represented by the formula (e-1) is an oxetanyl group. The group represented by the formula (e-2) is an alicyclic epoxy group.
[ chemical formula 13]
In the formula (e-1), R E1 Represents a hydrogen atom or an alkyl group, n represents 0 or 1, and x represents a bond; in formula (e-2), ring A E1 Represents an aliphatic hydrocarbon ring, and represents a bond.
R E1 The number of carbon atoms of the alkyl group represented is preferably 1 to 20, more preferably 1 to 10, still more preferably 1 to 5, particularly preferably 1 to 3.R is R E1 The alkyl group represented is preferably linear or branched, more preferably linear.
When n is 0, R E1 Preferably a hydrogen atom. When n is 1, R E1 Preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
When n in the formula (e-1) is 0, the formula (e-1) is a group represented by the following formula (e-1 a).
[ chemical formula 14]
Ring A of formula (e-2) E1 The aliphatic hydrocarbon ring represented may be a monocyclic aliphatic hydrocarbon ring or a condensed ring aliphatic hydrocarbon ring. And, ring A E1 The aliphatic hydrocarbon ring represented may have a crosslinked structure. Among them, from the viewpoint of easy formation of a film excellent in moisture resistance, it is preferably thickThe alicyclic hydrocarbon ring having a condensed ring having a crosslinked structure is preferable. As ring A E1 Specific examples of the aliphatic hydrocarbon ring represented by the formula (e-2-3) and the formula (e-2-4) are preferable. In the following formula, the bonding bond is represented.
[ chemical formula 15]
As the resin having a cyclic ether group, a resin containing a repeating unit having a cyclic ether group is preferably used. Examples of the repeating unit having a cyclic ether group include a repeating unit represented by the formula (A1).
[ chemical formula 16]
In the formula (A1), X a1 Represents a 3-valent linker, L a1 Represents a single bond or a 2-valent linking group, Z a1 Represents a cyclic ether group.
X is represented by the formula (A1) a1 Examples of the 3-valent linking group include a poly (meth) acrylic linking group, a polyalkyleneimine linking group, a polyester linking group, a polyurethane linking group, a polyurea linking group, a polyamide linking group, a polyether linking group, a polystyrene linking group, a bisphenol linking group, a novolak linking group, and the like, and the poly (meth) acrylic linking group, the polyether linking group, the polyester linking group, the bisphenol linking group, and the novolak linking group are preferable, the polyether linking group, the novolak linking group, and the poly (meth) acrylic linking group are more preferable, and the poly (meth) acrylic linking group is more preferable.
L as formula (A1) a1 The represented 2-valent linking group is an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO 2 -、-CO-、-O-, -COO-, -OCO-, -S-, and a combination of more than 2 of these groups. The alkylene group may be any of linear, branched and cyclic, and is preferably linear or branched. The alkylene group may have a substituent or may be unsubstituted. Examples of the substituent include a hydroxyl group and an alkoxy group.
Z as formula (A1) a1 Examples of the cyclic ether group include an epoxy group and an oxetanyl group, and epoxy groups are preferable. And Z is a1 The cyclic ether group represented is preferably a group represented by the formula (e-1) or a group represented by the formula (e-2), more preferably a group represented by the formula (e-2).
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.
The resin having a cyclic ether group may have a repeating unit other than the repeating unit having a cyclic ether group. Examples of the other repeating unit include a repeating unit having an acid group (hereinafter, also referred to as a repeating unit B-1), a repeating unit having a group in which an acid group is protected by a protecting group (hereinafter, also referred to as a repeating unit B-2), a repeating unit having a group containing an ethylenically unsaturated bond (hereinafter, also referred to as a repeating unit B-3), and the like.
Examples of the acid group of the repeating unit B-1 and the acid group protected by the protecting group of the repeating unit B-2 include phenolic hydroxyl groups, carboxyl groups, sulfo groups, and phosphate groups, and are preferably phenolic hydroxyl groups or carboxyl groups, and more preferably carboxyl groups.
Examples of the protecting group for protecting the acid group in the repeating unit B-2 include groups which are released by decomposition by the action of an acid or a base. The protecting group is preferably a group represented by any one of the formulae (Y1) to (Y5), and more preferably a group represented by the formula (Y3) or (Y5) in view of easiness of deprotection.
Formula (Y1): -C (R) Y1 )(R Y2 )(R Y3 )
Formula (Y2): -C (=o) OC (R Y4 )(R Y5 )(R Y6 )
Formula (Y3): -C (R) Y7 )(R Y8 )(OR Y9 )
Formula (Y4): -C (R) Y10 )(H)(Ar Y1 )
Formula (Y5): -C (=0) (R Y11 )
In the formula (Y1), R Y1 ～R Y3 Each independently represents alkyl, R Y1 ～R Y3 May be bonded to form a ring;
in the formula (Y2), R Y4 ～R Y6 Each independently represents alkyl, R Y4 ～R Y6 May be bonded to form a ring;
in the formula (Y3), R Y7 R is R Y8 Each independently represents a hydrogen atom, an alkyl group or an aryl group, R Y7 R is R Y8 At least one of which is alkyl or aryl, R Y9 Represents alkyl or aryl, R Y7 Or R is Y8 And R is R Y9 Can be bonded to form a ring;
ar in formula (Y4) Y1 Represents aryl, R Y10 Represents an alkyl group or an aryl group;
in the formula (Y5), R Y11 Represents an alkyl group or an aryl group.
R of formula (Y1) Y1 ～R Y3 The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 6, and still more preferably 1 to 4. The alkyl group may be any of linear, branched, and cyclic, and is preferably linear or branched. In the formula (Y1), R Y1 ～R Y3 Can be bonded to form a ring. As R Y1 ～R Y3 Examples of the ring formed by bonding 2 of (a) include monocyclic cycloalkyl groups such as cyclopentyl and cyclohexyl, polycyclic cycloalkyl groups such as norbornyl, tetracyclodecyl, tetracyclododecyl and adamantyl, and preferably monocyclic cycloalkyl groups having 5 to 6 carbon atoms. In the cycloalkyl group, 1 methylene group constituting the ring may be substituted with a group having a heteroatom such as an oxygen atom or a heteroatom such as a carbonyl group.
R of formula (Y2) Y4 ～R Y6 The number of carbon atoms of the alkyl group represented is preferably 1 to the maximum12, more preferably 1 to 6, still more preferably 1 to 4. The alkyl group may be any of linear, branched, and cyclic, and is preferably linear or branched. R of formula (Y2) Y4 ～R Y6 Preferably at least 2 of them are methyl groups. In the formula (Y2), R Y4 ～R Y6 Can be bonded to form a ring. The ring formed may be a ring described by the formula (Y1).
In the formula (Y3), R Y7 R is R Y8 Each independently represents a hydrogen atom, an alkyl group or an aryl group, R Y7 R is R Y8 At least one of which is alkyl or aryl, R Y9 Represents alkyl or aryl, R Y7 Or R is Y8 And R is R Y9 May be bonded to form a ring.
The alkyl group may be any of linear, branched, and cyclic. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 6, and still more preferably 1 to 4. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12. As RY7 or R Y8 And R is R Y9 Examples of the ring formed by bonding include a tetrahydrofuranyl group and a tetrahydropyranyl group. In the formula (Y3), R is preferable Y7 Or R is Y8 And R is R Y9 Bonding to form a ring. And is preferably R Y7 R is R Y8 One of which is a hydrogen atom.
Ar in formula (Y4) Y1 Represents aryl, R Y10 Represents alkyl or aryl, ar Y1 And R is R Y10 May bond 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 still more preferably 1 to 4. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12. In the formula (Y4), R is preferable Y10 Is alkyl.
In the formula (Y5), R Y11 Represents alkyl or aryl, preferably alkyl. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 6, and still more preferably 1 to 4. The number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12.
The molecular weight of the protecting group is preferably 40 to 200, more preferably 40 to 150, and still more preferably 40 to 120. When the molecular weight of the protecting group is within the above range, a colored composition having excellent storage stability and excellent curability at low temperatures can be produced.
Specific examples of the protecting group include 1-methoxyethyl, 1-ethoxyethyl, 1-n-propoxyethyl, 1-n-butoxyethyl, 1-t-butoxyethyl, 1-cyclopentyloxyethyl, 1-cyclohexyloxyethyl, cyclohexylmethyl, α -methoxybenzyl, α -ethoxybenzyl, α -n-propoxybenzyl, 2-phenyl-1-methoxyethyl, 2-phenyl-1-ethoxyethyl, 2-phenyl-1-isopropoxyethyl, 2-tetrahydrofuranyl, 2-tetrahydropyranyl, preferably 1-ethoxyethyl, 1-cyclohexyloxyethyl, 2-tetrahydrofuranyl, 2-tetrahydropyranyl, more preferably 1-ethoxyethyl, 1-cyclohexyloxyethyl.
Examples of the ethylenically unsaturated bond-containing group contained in the repeating unit B-3 include a vinyl group, a styryl group, a (meth) allyl group, and a (meth) acryl group.
The repeating unit B-1 is represented by the following formula (B1). The repeating unit B-2 may be represented by the following formula (B2). The repeating unit B-3 may be represented by the following formula (B3).
[ chemical formula 17]
In the formula (B1), X b1 Represents a 3-valent linker, L b1 Represents a single bond or a 2-valent linking group, Z b1 Represents an acid group.
In the formula (B2), X b2 Represents a 3-valent linker, L b2 Represents a single bond or a 2-valent linking group, Z b2 Represents a group in which an acid group is protected by a protecting group.
In the formula (B3), X b3 Represents a 3-valent linker, L b3 Represents a single bond or a 2-valent linking group, Z b3 Represents a group containing an ethylenically unsaturated bond.
X is represented by the formula (B1) b1 Represented by the formula (B2) X, a 3-valent linking group b2 Represented by the formula (B3) and X b3 Represented byThe 3-valent linking group is not particularly limited. Examples thereof include a poly (meth) acrylic acid-based linker, a polyalkyleneimine-based linker, a polyester-based linker, a polyurethane-based linker, a polyurea-based linker, a polyamide-based linker, a polyether-based linker, a polystyrene-based linker, a bisphenol-based linker, a novolak-based linker, and the like, preferably a poly (meth) acrylic acid-based linker, a polyether-based linker, a polyester-based linker, a bisphenol-based linker, and a novolak-based linker, more preferably a poly (meth) acrylic acid-based linker.
L as formula (B1) b1 Represented by the formula (B2) and L b2 Represented by the formula (B3) and L b3 Examples of the 2-valent linking group include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO 2 -, -CO-, -O-; -COO-, -OCO-, S-and a group formed by combining 2 or more of these. The alkylene group may be any of linear, branched and cyclic, and is preferably linear or branched. The alkylene group may have a substituent or may be unsubstituted. Examples of the substituent include a hydroxyl group and an alkoxy group.
Z as formula (B1) b1 Examples of the acid group include a phenolic hydroxyl group, a carboxyl group, a sulfo group and a phosphate group, and the phenolic hydroxyl group or the carboxyl group is preferable, and the carboxyl group is more preferable.
Z as formula (B2) b2 Examples of the group in which the acid group is protected with a protecting group include groups in which the acid group is protected with a group represented by any one of the above formulas (Y1) to (Y5), and preferably groups in which the acid group is protected with a group represented by the formula (Y3) or (Y5). Examples of the acid group include a phenolic hydroxyl group, a carboxyl group, a sulfo group, and a phosphate group, and a phenolic hydroxyl group or a carboxyl group is preferable, and a carboxyl group is more preferable.
Z as formula (B3) b3 Examples of the ethylenically unsaturated bond-containing group include vinyl, styryl, (meth) allyl, and (meth) acryl.
In the case where 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% in 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.
In the case where 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.
When the resin having a cyclic ether group contains the repeating unit B-1 and the repeating unit B-2, the resin having a cyclic ether group preferably contains 0.4 to 3.2 moles, more preferably 0.8 to 2.8 moles, and still more preferably 1.2 to 2.4 moles, relative to 1 mole of the repeating unit B-1.
In the case where 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.
The resin having a cyclic ether group preferably further contains a repeating unit having an aromatic hydrocarbon ring. The aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring, and preferably a benzene ring. The aromatic hydrocarbon ring may have a substituent. Examples of the substituent include an alkyl group and the like. 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% based on 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 a monofunctional polymerizable compound having an aromatic hydrocarbon ring such as vinyltoluene and benzyl (meth) acrylate.
Examples of the commercially available resin having a cyclic ether group include EPICLON HP5000 and EPICLON HP4032D (the above is manufactured by DIC CORPORATION) as naphthalene-modified epoxy resins. Examples of the alkyldiphenol type epoxy resin include EPICLON 820 (DIC CORPORATION). Examples of bisphenol A type epoxy resins include jER825, jER827, jER828, jER834, jER1001, jER1002, jER1003, jER1055, jER1007, jER1009, jER1010 (manufactured by Mitsubishi ChemicalCorporation above), EPICLON860, EPICLON1050, EPICLON1051, EPICLON1055 (manufactured by DIC CORPORATION above), and the like. Examples of bisphenol F type epoxy resins include jER806, jER807, jER4004, jER4005, jER4007, jER4010 (manufactured by Mitsubishi ChemicalCorporation, supra), EPICLON830, EPICLON835 (manufactured by DIC CORPORATION, supra), LCE-21, RE-602S (manufactured by Nippon Kayaku Co., ltd.). Examples of the phenol novolac type epoxy resin include jER152, jER154, jER157S70, jER157S65 (manufactured by Mitsubishi Chemical Corporation above), EPICLON-740, EPICLON-770, EPICLON-775 (manufactured by DIC CORPORATION above), and the like. Examples of the cresol novolac type epoxy resin include EPICLON-660, EPICLON-665, EPICLON-670, EPICLON-673, EPICLON-680, EPICLON-690, EPICLON-695 (DIC CORPORATION, above), EOCN-1020 (Nippon Kayaku Co., ltd.). Examples of the aliphatic epoxy resin include ADEKA RESIN EP to 4080S, ADEKA RESIN EP to 4085S, ADEKA RESIN EP to 4088S (manufactured by ADEKA Corporation above), CELLOXIDE 2021P, CELLOXIDE 2081, CELLOXIDE 2083, CELLOXIDE2085, EHPE3150, EPOLEAD PB 3600, EPOLEAD PB 4700 (manufactured by Daicel Corporation above), DENACOL EX-212L, EX-214L, EX-216L, EX-321L, EX-850L (manufactured by Nagase ChemteX Corporation above), and the like. The resin having a cyclic ether group may be any of the resins described in paragraphs 0034 to 0036 of Japanese patent application laid-open No. 2013-011689, the resins described in paragraphs 0147 to 0156 of Japanese patent application laid-open No. 2014-043556, the resins described in paragraphs 0085 to 0092 of Japanese patent application laid-open No. 2014-089408, the resins described in Japanese patent application laid-open No. 2017-179172, the resins described in paragraphs 0027 to 0055 and 0096 of Japanese patent application laid-open 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.
As the resin, a resin having an aromatic carboxyl group (hereinafter, also referred to as a resin Ac) is also preferably used. In the resin Ac, the aromatic carboxyl group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit. The aromatic carboxyl group is preferably contained in the main chain of the repeating unit. In the present specification, the aromatic carboxyl group means a group having a structure in which 1 or more carboxyl groups are bonded to an aromatic ring. The number of carboxyl groups bonded to the aromatic ring in the aromatic carboxyl groups is preferably 1 to 4, more preferably 1 to 2.
The resin Ac is preferably a resin comprising at least 1 repeating unit selected from the repeating units represented by the formula (Ac-1) and the repeating units represented by the formula (Ac-2).
[ chemical formula 18]
Ar in formula (Ac-1) 1 Represents a group containing an aromatic carboxyl group, L 1 represents-COO-or-CONH-, L 2 Represents a 2-valent linking group.
Ar in formula (Ac-2) 10 Represents a group containing an aromatic carboxyl group, L 11 represents-COO-or-CONH-, L 12 Represents a 3-valent linker, P 10 Representing a polymer chain.
Ar in formula (Ac-1) 1 Examples of the group containing an aromatic carboxyl group include a structure derived from an aromatic tricarboxylic anhydride, a structure derived from an aromatic tetracarboxylic anhydride, and the like. Examples of the aromatic tricarboxylic acid anhydride and the aromatic tetracarboxylic acid anhydride include compounds having the following structures.
[ chemical formula 19]
In the above, Q 1 Represents a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-、-SO 2 -、-C(CF 3 ) 2 -, a group represented by the following formula (Q-1) or a group represented by the following formula (Q-2).
[ chemical formula 20]
Ar 1 The represented group containing an aromatic carboxyl group may have a crosslinkable group. The crosslinkable group is preferably an ethylenically unsaturated bond-containing group or a cyclic ether group, more preferably an ethylenically unsaturated bond-containing group. As Ar 1 Specific examples of the group containing an aromatic carboxyl group represented by the formula (Ar-11), the group represented by the formula (Ar-12), the group represented by the formula (Ar-13), and the like are given.
[ chemical formula 21]
In the formula (Ar-11), n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
In the formula (Ar-12), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and further preferably 2.
In the 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. Wherein at least one of n3 and n4 is an integer of 1 or more.
In the formula (Ar-13), Q 1 Represents a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-、-SO 2 -、-C(CF 3 ) 2 -, a group represented by the above formula (Q-1) or a group represented by the above formula (Q-2).
In the formulae (Ar-11) to (Ar-13), 1 represents a group represented by formula L 1 Is used for the bonding position of the substrate.
In the formula (Ac-1), L 1 Representation of-COO-or-CONH-, preferably represents-COO-.
As L in formula (Ac-1) 2 Examples of the 2-valent linking group include an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-and a combination of 2 or more of these groups. 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 may 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 arylene group may have a substituent. Examples of the substituent include a hydroxyl group and the like. L (L) 2 The represented 2-valent linking group is preferably represented by-L 2a -a group represented by O-. L (L) 2a An alkylene group; arylene groups; a group formed by combining an alkylene group and an arylene group; at least 1 selected from alkylene and arylene groups and at least one selected from-O- -CO-, -COO-, at least 1 of the groups OCO-, -NH-and-S-, alkylene groups are preferred. 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 may be any of linear, branched, and cyclic. The alkylene group and arylene group may have a substituent. Examples of the substituent include a hydroxyl group and the like.
Ar in formula (Ac-2) 10 A group containing an aromatic carboxyl group represented by the formula (Ac-1) and Ar 1 The meaning of (2) is the same and the preferred ranges are also the same.
In the formula (Ac-2), L 11 represents-COO-or-CONH-, preferably-COO-.
As L in formula (Ac-2) 12 Examples of the 3-valent linking group include a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-and a combination of 2 or more of these groups. Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 15. The aliphatic hydrocarbon group may be any of straight chain, branched chain, and cyclic. The number of carbon atoms of 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 and the like. L (L) 12 The 3-valent linking group represented by formula (L12-1) is preferably a groupThe group is more preferably a group represented by the formula (L12-2).
[ chemical formula 22]
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In the formula (L12-1), L 12b Represents a 3-valent linking group, X 1 Represents S, 1 represents L of formula (Ac-2) 11 Is represented by the formula (Ac-2) 10 Is used for the bonding position of the substrate. As L 12b Examples of the 3-valent linking group include a hydrocarbon group; hydrocarbyl radicals and are selected from the group consisting of-O-, -CO-, -COO-, -OCO-, at least 1 of-NH-and-S-and the like, preferably a hydrocarbon group or a combination of a hydrocarbon group and-O-.
In the formula (L12-2), L 12c Represents a 3-valent linking group, X 1 Represents S, 1 represents L of formula (Ac-2) 11 Is represented by the formula (Ac-2) 10 Is used for the bonding position of the substrate. As L 12c Examples of the 3-valent linking group include a hydrocarbon group; hydrocarbyl radicals and are selected from the group consisting of-O-, -CO-, -COO-, -OCO-, at least 1 of-NH-and-S-and the like, preferably a hydrocarbon group.
In the formula (Ac-2), P 10 Representing a polymer chain. P (P) 10 The polymer chain represented preferably has at least 1 repeating unit selected from the group consisting of poly (meth) acrylic acid repeating units, polyether repeating units, polyester repeating units and polyol repeating units. Polymer chain P 10 The weight average molecular weight of (2) is preferably 500 to 20000. The lower limit is preferably 1000 or more. The upper limit is preferably 10000 or less, more preferably 5000 or less, and even more preferably 3000 or less. If P 10 When the weight average molecular weight of (b) is within the above range, the dispersibility of the pigment in the composition is good. In the case where the resin having an aromatic carboxyl group is a resin having a repeating unit represented by the formula (Ac-2), the resin can be preferably used as a dispersant.
P 10 The indicated polymer chain may comprise crosslinkable groups. Examples of the crosslinkable group include an ethylenically unsaturated bond-containing group and a cyclic ether group.
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 an alkaline dispersant (alkaline resin). Here, the acidic dispersant (acidic resin) means a resin having an amount of acid groups larger than an amount of basic groups. When the total amount of the acid groups and the basic groups is 100 mol% as the acid dispersant (acid resin), a resin having an acid group amount of 70 mol% or more is preferable. The acid group of the acidic dispersant (acidic resin) is preferably a carboxyl group. The acid value of the acidic dispersant (acidic resin) is preferably 10 to 105mgKOH/g. The basic dispersant (basic resin) is a resin having a larger amount of basic groups 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 preferable. The basic group of the basic dispersant is preferably an amino group.
The resin used as the dispersant is also preferably a graft resin. For details of the graft resin, refer to paragraphs 0025 to 0094 of Japanese patent application laid-open No. 2012-255128, which is incorporated herein by reference.
The resin used as the dispersant is also preferably a polyimide-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain. The polyimide-based dispersant is preferably a resin having a main chain and a side chain, wherein at least one of the main chain and the side chain has a basic nitrogen atom, the main chain includes a partial structure having a functional group with a pKa of 14 or less, and the number of atoms of the side chain is 40 to 10000. The basic nitrogen atom is not particularly limited as long as it is a basic nitrogen atom. The polyimide-based dispersant can be described in paragraphs 0102 to 0166 of Japanese patent application laid-open No. 2012-255128, incorporated herein by reference.
The resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core. Examples of such resins include dendrimers (including star polymers). Specific examples of the dendrimer include the polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A2013-043962.
The resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in a side chain. The content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, still more preferably 20 to 70 mol% of all the repeating units of the resin.
The dispersing agent may be a resin described in JP-A2018-087939, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of JP-A6432077, polyethyleneimine having a polyester side chain described in International publication 2016/104803, block copolymer having an acrylamide structural unit described in JP-A2020-066687, block polymer having an acrylamide structural unit described in JP-A2020-066688, or dispersing agent described in International publication 2016/104803.
The dispersant may be commercially available, and specific examples thereof include the Disperbyk series (e.g., disperbyk-111, 161, 2001, etc.) manufactured by LTD, the solserse series (e.g., solserse 20000, 76500, etc.) manufactured by Lubrizol Japan limited, the Ajinomoto Fine-Techno co., the ajper series manufactured by inc. Further, the product described in 0129 of japanese patent application laid-open No. 2012-137564 and the product described in 0235 of japanese patent application laid-open No. 2017-194662 can be used as the dispersant.
The content of the resin in the total solid content of the coloring composition is preferably 1 to 50 mass%. The upper limit is preferably 40 mass% or less, more preferably 30 mass% or less. The lower limit is preferably 5 mass% or more, more preferably 10 mass% or more. The coloring composition of the present invention may contain only 1 resin or 2 or more resins. When the resin contains 2 or more kinds, the total amount of these is preferably within the above range.
Polymerizable Compound
The coloring composition of the present invention preferably contains a polymerizable compound. Examples of the polymerizable compound include a compound having a group containing an ethylenically unsaturated bond. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group. The polymerizable compound used in the present invention is preferably a radical polymerizable compound.
The polymerizable compound may be any of chemical forms such as monomers, prepolymers, and oligomers, but monomers are 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.
From the viewpoint of the stability with time of the coloring composition, the value of the group containing an ethylenic unsaturated bond (hereinafter referred to as c=c value) of the polymerizable compound is preferably 2 to 14mmol/g. The lower limit is preferably 3mmol/g or more, more preferably 4mmol/g or more, and still more preferably 5mmol/g or more. The upper limit is preferably 12mmol/g or less, more preferably 10mmol/g or less, and still more preferably 8mmol/g or less. The c=c value of the polymerizable compound is a value calculated by dividing the number of ethylenically unsaturated bond-containing groups contained in 1 molecule of the polymerizable compound by the molecular weight of the polymerizable compound.
The polymerizable compound preferably contains 3 or more ethylenically unsaturated bond-containing groups, more preferably contains 4 or more ethylenically unsaturated bond-containing groups. The upper limit of the ethylenically unsaturated bond-containing group is preferably 15 or less, more preferably 10 or less, and even more preferably 6 or less, from the viewpoint of the stability over time of the coloring composition. The polymerizable compound is preferably a 3-functional or more (meth) acrylate compound, more preferably a 3-15-functional (meth) acrylate compound, still more preferably a 3-10-functional (meth) acrylate compound, and particularly preferably a 3-6-functional (meth) acrylate compound.
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 compounds having a structure in which a (meth) acryloyl group of the above-mentioned compound is bonded via an alkyleneoxy group, such as ethoxylated dipentaerythritol hexa (meth) acrylate. Specific examples thereof include a compound represented by the formula (Z-4) and a compound represented by the formula (Z-5).
[ chemical formula 23]
In the formulae (Z-4) and (Z-5), E independently represents- ((CH) 2 ) y CH 2 O) -or- ((CH) 2 ) y CH(CH 3 ) O) -, y each independently represents an integer of 0 to 10, and X each independently represents a (meth) acryloyl group, a hydrogen atom, or a carboxyl group. In the formula (Z-4), the total number of (meth) acryloyl groups is 3 or 4, m independently represents an integer of 0 to 10, and the total number of m is an integer of 0 to 40. In the formula (Z-5), the total number of (meth) acryloyl groups is 5 or 6, n is an integer of 0 to 10, and the total number of n is an integer of 0 to 60.
In the formula (Z-4), m is preferably an integer of 0 to 6, more preferably an integer of 0 to 4. The total of m is preferably an integer of 2 to 40, more preferably an integer of 2 to 16, and particularly preferably an integer of 4 to 8.
In the formula (Z-5), n is preferably an integer of 0 to 6, more preferably an integer of 0 to 4. The total of n is preferably an integer of 3 to 60, more preferably an integer of 3 to 24, and particularly preferably an integer of 6 to 12.
And, E in the formula (Z-4) or (Z-5), i.e., - ((CH) 2 ) y CH 2 O) -or- ((CH) 2 ) y CH(CH 3 ) O) -is a form in which the terminal on the oxygen atom side is bonded to X.
Also, as the polymerizable compound, a dipentaerythritol poly (meth) acrylate represented by the following formula (Z-6) can be used.
[ chemical formula 24]
In the formula (Z-6), X 1 ～X 6 Each independently represents a hydrogen atom or a (meth) acryloyl group, and n represents an integer of 1 to 10. Here, X is 1 ～X 6 At least one of them is a (meth) acryl group.
The polymerizable compound used in the present invention is preferably at least 1 selected from dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol poly (meth) acrylate, and modified products thereof. Examples of the commercial products include KAYARAD D-310, DPHA, DPEA-12 (Nippon Kayaku Co., ltd.), NK ESTER A-DPH-12E, TPOA-50 (Shin-Nakamura Chemical Co., ltd.), and the like.
Further, as the polymerizable compound, diglycerol EO (ethylene oxide) -modified (meth) acrylate (as a commercially available product, M-460; TOAGOSEI CO., LTD. Manufactured), pentaerythritol tetra (meth) acrylate (Shin-Nakamura Chemical Co., ltd., NK ESTER A-TMMT), 1, 6-hexanediol diacrylate (Nippon Kayaku Co., ltd., 1040, KAYARAD HDDA), RP-acrylate (Nippon Kayaku Co., ltd., manufactured), ARONIX TO-2349 (TOAGOSEI CO., LTD. Manufactured), NK OLIGO UA-7200 (Shin-Nakamura Chemical Co., ltd., manufactured), 8UH-1006, 8UH-1012 (TAISEI FINE CHEMICAL CO., LTD. Manufactured), LIGHT ACRYLATE POB-A0 (KYOEISHA CHEMICAL CO., LTD. Manufactured), ECRYL80 (DAALD-LTD functional) LND 4, etc. can be used.
Further, as the polymerizable compound, a 3-functional (meth) acrylate compound 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, pentaerythritol tri (meth) acrylate, and the like is also preferably used. Examples of THE commercial products of THE 3-functional (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 (TOAGOSEI CO., LTD. Manufactured), NK ESTER A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A-TMM-3LM-N, A-TMPT, TMPT (Shin-Nakamura Chemical Co., ltd. Manufactured), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (Nippon Kayaku Co., manufactured by Ltd.).
Further, as the polymerizable compound, a compound having an acid group such as a carboxyl group, a sulfo group, or a phosphate group can be used. Examples of commercial products of such compounds include ARONIX M-305, M-510, M-520, ARONIX TO-2349 (TOAGOSEI CO., LTD. Co.), and the like.
Further, a compound having a caprolactone structure can be used as the polymerizable compound. For the compound having a caprolactone structure, reference may be made to paragraphs 0042 to 0045 of Japanese patent application laid-open No. 2013-253224, which is incorporated herein by reference. Examples of the compound having a caprolactone structure include DPCA-20, DPCA-30, DPCA-60, DPCA-120, which are commercially available as KAYARAD DPCA series from Nippon Kayaku Co., ltd.
Furthermore, as the polymerizable compound, a polymerizable compound having a fluorene skeleton can be used. Examples of the commercial products include OGSOL EA-0200 and EA-0300 (Osaka Gas Chemicals Co., ltd., a (meth) acrylate monomer having a fluorene skeleton).
Further, as the polymerizable compound, a compound which does not substantially contain an environmental control substance such as toluene is also preferable. Examples of commercial products of such compounds include KAYARAD DPHA LT, KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku co., ltd.) and the like.
Further, as the polymerizable compound, urethane compounds having an ethylene oxide skeleton as described in Japanese patent application laid-open No. 48-041708, japanese patent application laid-open No. 51-037193, japanese patent application laid-open No. 02-032293, japanese patent application laid-open No. 02-016765, japanese patent application laid-open No. 58-049860, japanese patent application laid-open No. 56-017654, japanese patent application laid-open No. 62-039417, and Japanese patent application laid-open No. 62-039418 are also preferred. Furthermore, it is also preferable to use a polymerizable compound having an amino structure or a thioether structure in the molecule as described in JP-A-63-277653, JP-A-63-260909 and JP-A-01-105238. Further, commercially available products such as UA-7200 (Shin-Nakamura Chemical Co., ltd.), DPHA-40H (Nippon Kayaku Co., ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (KYOEISHA CHEMICAL CO., LTD.) and the like can be used as the polymerizable compound.
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 mass% or less, more preferably 25 mass% or less. The lower limit is preferably 2 mass% or more, more preferably 5 mass% or more. The coloring composition of the present invention may contain only 1 polymerizable compound or may contain 2 or more kinds. When the polymerizable compound contains 2 or more kinds, the total amount of these compounds is preferably within the above range.
Photopolymerization initiator
The coloring composition of the present invention can contain a photopolymerization initiator. In the case where 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 may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays ranging from the ultraviolet region to the visible region is preferable. The photopolymerization initiator is preferably a photo radical polymerization initiator.
Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, and the like), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, α -hydroxyketone compounds, and α -aminoketone compounds. From the viewpoint of exposure sensitivity, the photopolymerization initiator is preferably a trihalomethyltriazine (trihalo methyl triazine) compound, a benzyldimethyl ketal compound, an α -hydroxyketone compound, an α -aminoketone 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 halomethyloxadiazole compound, and a 3-aryl-substituted coumarin compound, more preferably a compound selected from the group consisting of an oxime compound, an α -hydroxyketone compound, an α -aminoketone compound, and an acylphosphine compound, and further preferably an oxime compound. Examples of the photopolymerization initiator include a compound described in paragraphs 0065 to 0111 of Japanese patent application laid-open No. 2014-130173, a compound described in Japanese patent application laid-open No. 6301489, MATERIAL STAGE to 60p, vol.19, no.3, a peroxide-based photopolymerization initiator described in 2019, a photopolymerization initiator described in International publication No. 2018/221177, a photopolymerization initiator described in International publication No. 2018/110179, a photopolymerization initiator described in Japanese patent application laid-open No. 2019-043864, a photopolymerization initiator described in Japanese patent application laid-open No. 2019-044030, a peroxide-based initiator described in Japanese patent application laid-open No. 2019-167313, an aminoacetophenone-based initiator having an oxazolidinyl group described in Japanese patent application laid-open No. 2020-055992, an oxime-based photopolymerization initiator described in Japanese patent application laid-open No. 2013-1909, a polymer described in Japanese patent application laid-open No. 2020-619, and the like, and these are incorporated herein.
Specific examples of the hexaarylbiimidazole compound include 2,2', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4, 5-diphenyl-1, 1' -bisimidazole and the like.
Examples of the commercial products of the α -hydroxyketone compounds include Omnirad 184, omnirad 1173, omnirad 2959, omnirad 127 (which is manufactured by IGM Resins b.v. company, above), irgacure 184, irgacure 1173, irgacure 2959, irgacure 127 (which is manufactured by BASF company, above), and the like. Commercial products of α -aminoketone compounds, such as Omnirad 907, omnirad 369E, omnirad 379EG (manufactured by IGM Resins b.v. company, supra), irgacure 907, irgacure 369E, irgacure 379EG (manufactured by BASF company, supra), and the like. Examples of commercial products of the acylphosphine compound include Omnirad 819, omnirad TPO (made by IGM Resins b.v. company, above), irgacure 819, irgacure TPO (made by BASF company, above), and the like.
Examples of the oxime compound include a compound described in Japanese patent application laid-open No. 2001-233846, a compound described in Japanese patent application laid-open No. 2000-080068, a compound described in Japanese patent application laid-open No. 2006-342166, a compound described in J.C.S. Perkin II (1979, pp.1653-1660), a compound described in J.C.S. Perkin II (1979, pp.156-162), a compound described in Journal of Photopolymer Science and Technology (1995, pp.202-232), a compound described in Japanese patent application laid-open No. 2000-066385, a compound described in Japanese patent application laid-open No. 2004-534797, a compound described in Japanese patent application laid-open No. 2006-342166, a compound described in Japanese patent application laid-open No. 019766, a compound described in Japanese patent application laid-open No. 6065596, a compound described in International publication No. 20158/152153, a compound described in International publication No. 2015-2015, a publication No. 2015-2015, and the like. Specific examples of the oxime compound include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino1-phenylpropane-1-one, 2-benzoyloxyimino1-phenylpropane-1-one, 3- (4-toluenesulfonyloxy) iminobutan-2-one, 2-ethoxycarbonyloxyimino1-phenylpropane-1-one, 1- [4- (phenylthio) phenyl ] -3-cyclohexyl-propane-1, 2-dione-2- (0-acetyl oxime) and the like. Examples of the commercial products include Irgacure OXE01, irgacure OXE02, irgacure OXE03, irgacure OXE04 (the above is manufactured by BASF), TR-PBG-304, TR-PBG-327 (manufactured by TRONLY), ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation, and photopolymerization initiator 2 described in Japanese patent application laid-open No. 2012-014052). Furthermore, as the oxime compound, a compound which is free from coloring or a compound which is highly transparent and hardly discolored is preferably used. Examples of the commercial products include ADEKA ARKLS NCI-730, NCI-831, and NCI-930 (manufactured by ADEKA CORPORATION).
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 a compound described in JP-A2014-137466, a compound described in JP-A6636081, and a compound described in Korean patent application No. 10-2016-0109444.
As the photopolymerization initiator, an oxime compound having a skeleton in which at least one benzene ring in the carbazole ring is a naphthalene ring can also be used. Specific examples of such oxime compounds include those described in international publication No. 2013/083505.
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 a compound described in JP-A2010-26261028, compounds 24, 36 to 40 described in JP-A2014-500852, and compound (C-3) described in JP-A2013-164471.
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 compounds described in paragraphs 0031 to 0047 of Japanese patent application laid-open No. 2013-114249, 0008 to 0012 and 0070 to 0079 of Japanese patent application laid-open No. 2014-137466, compounds described in paragraphs 0007 to 0025 of Japanese patent application laid-open No. 4223071, and ADEKA ARKLS NCI-831 (manufactured by ADEKA CORPORATION).
As the photopolymerization initiator, an oxime compound having a benzofuran skeleton can also be used. Specific examples thereof include OE-01 to OE-75 described in International publication No. 2015/036910.
As the photopolymerization initiator, an oxime compound having a substituent having a hydroxyl group bonded to the carbazole skeleton can also be used. Examples of such photopolymerization initiators include compounds described in International publication No. 2019/088055.
As the photopolymerization initiator, ar having an aromatic ring group in which an electron-withdrawing group is introduced into an aromatic ring can also be used OX1 An oxime compound (hereinafter, also referred to as oxime compound OX). Ar as the above aromatic ring group OX1 Examples of the electron withdrawing group includeThe acyl group, the nitro group, the trifluoromethyl group, the alkylsulfinyl group, the arylsulfinyl group, the alkylsulfonyl group, the arylsulfonyl group, the cyano group, the acyl group and the nitro group are preferable, and from the viewpoint of easy formation of a film excellent in light resistance, more preferable is an acyl group, and still more preferable is a benzoyl group. The benzoyl group may have a substituent. The substituent is preferably a halogen atom, cyano group, nitro group, hydroxyl group, alkyl group, alkoxy group, aryl group, aryloxy group, heterocyclic oxy group, alkenyl group, alkylthio group, arylthio group, acyl group or amino group, more preferably an alkyl group, alkoxy group, aryl group, aryloxy group, heterocyclic oxy group, alkylthio group, arylthio group or amino group, still more preferably an alkoxy group, alkylthio group or amino group.
The oxime compound OX is preferably at least 1 selected from the group consisting of a compound represented by the formula (OX 1) and a compound represented by the formula (OX 2), more preferably a compound represented by the formula (OX 2).
[ chemical formula 25]
Wherein R is X1 Represents alkyl, alkenyl, alkoxy, aryl, aryloxy, heterocyclyl, heterocyclyloxy, alkylsulfanyl, arylsulfanyl, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, acyl, acyloxy, amino, phosphono, carbamoyl or sulfamoyl,
R X2 represents alkyl, alkenyl, alkoxy, aryl, aryloxy, heterocyclyl, heterocyclyloxy, alkylsulfanyl, arylsulfanyl, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, acyloxy or amino,
R X3 ～R X14 each independently represents a hydrogen atom or a substituent;
wherein R is X10 ～R X14 At least one of which is an electron withdrawing group.
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, and an acyl group and a nitro group are preferable, an acyl group is more preferable, and a benzoyl group is further preferable, from the viewpoint of easy formation of a film excellent in light resistance.
In the above formula, R X12 R is an electron withdrawing group X10 、R X11 、R X13 、R X14 Preferably a hydrogen atom.
Specific examples of the oxime compound OX include compounds described in paragraphs 0083 to 0105 of japanese patent No. 4600600.
Specific examples of the oxime compound preferably used in the present invention are shown below, but the present invention is not limited to these.
[ chemical formula 26]
[ chemical formula 27]
[ chemical formula 28]
The oxime compound is preferably a compound having a maximum absorption wavelength in the range of 350 to 500nm, more preferably a compound having a maximum absorption wavelength in the range of 360 to 480 nm. Further, from the viewpoint of sensitivity, the molar absorption coefficient of the oxime compound at 365nm or 405nm is preferably high, more preferably 1000 to 300000, still more preferably 2000 to 300000, particularly preferably 5000 to 200000. The molar absorptivity of the compound can be measured by a known method. For example, it is preferable to measure the concentration of the solvent by a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian Co., ltd.) using ethyl acetate at a concentration of 0.01 g/L.
As photopolymerization initiators, irgacure OXE01 (manufactured by BASF) and/or Irgacure OXE02 (manufactured by BASF) and Omnirad 2959 (manufactured by IGM Resins B.V.) are also preferably used in combination.
As the photopolymerization initiator, a 2-functional or 3-functional or more photo radical polymerization initiator can be used. By using such a photo radical polymerization initiator, 2 or more radicals are generated from one molecule of the photo radical polymerization initiator, and thus good sensitivity can be obtained. In addition, when a compound having an asymmetric structure is used, crystallinity is reduced, and solubility in a solvent or the like is improved, and precipitation becomes difficult with time, so that stability of the coloring composition with time can be improved. Specific examples of the 2-functional or 3-functional or more photo-radical polymerization initiator include the oxime compound dimer described in paragraphs 0407 to 0412 of Japanese patent application laid-open No. 2015/004565, the oxime compound dimer described in paragraphs 0039 to 0055 of Japanese patent application laid-open No. 2017/033680, the compound (E) and the compound (G) described in Japanese patent application laid-open No. 2013-522445, the oxime ester photoinitiator described in paragraphs Cmpd1 to 7 of Japanese patent application laid-open No. 2016/034963, the oxime ester photoinitiator described in paragraph 0007 of Japanese patent application laid-open No. 2017-523465, the photoinitiator described in paragraphs 0020 to 1673 of Japanese patent application laid-open No. 2017-167399, the photopolymerization initiator (A) described in paragraphs 2017 to 0026 of Japanese patent application laid-open No. 2017-151342, and the oxime ester photoinitiator described in patent application laid-open No. 6469669.
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 mass% or more, more preferably 1 mass% or more. The upper limit is preferably 20 mass% or less, more preferably 15 mass% or less. In the coloring composition of the present invention, 1 kind of photopolymerization initiator may be used alone, or 2 or more kinds may be used. When 2 or more kinds are used, the total of them is preferably within the above range.
Solvent (S)
The coloring composition of the present invention preferably contains a solvent. As the solvent, an organic solvent can be mentioned. The type of the solvent is not particularly limited basically as long as the solubility of each component or the coatability of the composition is satisfied. Examples of the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. For details of these, reference can be made to paragraph 0223 of International publication No. 2015/166779, which is incorporated herein. Also, a cyclic alkyl substituted ester solvent or a cyclic alkyl substituted ketone solvent can be preferably used. Specific examples of the organic solvent include polyethylene glycol monomethyl ether, methylene chloride, methyl 3-ethoxypropionate, ethyl sirtuin 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 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, diacetobutane-1, 3-diyl, dipropylene glycol methyl ether acetate, diacetone (referred to as diacetone, 4-hydroxy-4-methyl-pentanone), 2-isopropyl alcohol, and isopropyl alcohol. However, for environmental reasons, the reduction of the aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as the organic solvent is preferably (for example, 50 mass ppm (parts per million) or less, 10 mass ppm or less, or 1 mass ppm or less relative to the total amount of the organic solvent) or the like.
In the present invention, an organic solvent having a small metal content is preferably used. The metal content of the organic solvent is preferably 10 ppb (parts per billion, one part per billion) by mass or less, for example. If desired, a quality ppt (parts per trillion: parts per trillion) grade of organic solvent, such as provided by Toyo Gosei co., ltd (chemical industry journal, 2015, 11, 13) may be used.
Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter. The filter pore diameter of the filter used for filtration is preferably 10 μm or less, more preferably 5 μm or less, and further preferably 3 μm or less. The material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
The organic solvent may contain isomers (compounds having the same number of atoms but different structures). The isomer may be contained in 1 or more types.
The content of the peroxide in the organic solvent is preferably 0.8mmol/L or less, and more preferably substantially no peroxide is contained.
The content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and still more preferably 30 to 90% by mass.
Further, from the viewpoint of environmental control, it is preferable that the coloring composition of the present invention contains substantially no environmental control substance. In the present invention, the fact that the coloring composition does not substantially contain an environmental control substance means that the content of the environmental control substance in the coloring composition is 50 mass ppm or less, preferably 30 mass ppm or less, more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less. Examples of the environmental control substance include benzene; alkylbenzenes such as toluene and xylene; halogenated benzenes such as chlorobenzene, etc. These are registered as environment-regulated substances under REACH (Registration Evaluation Authorization and Restriction of CHemicals) regulation, PRTR (Pollutant Release and Transfer Register) method, VOC (Volatile Organic Compounds) regulation, etc., and the use amount and treatment method are strictly regulated. These compounds are sometimes used as solvents in the production of components and the like for use in the coloring composition, and may be mixed into the coloring composition as residual solvents. From the viewpoints of safety to humans and environmental considerations, it is preferable to reduce these substances as much as possible. As a method for reducing the environmental controlled substance, there is a method in which the inside of the system is heated and depressurized to a temperature equal to or higher than the boiling point of the environmental controlled substance, and the environmental controlled substance is distilled from the inside of the system and reduced. In addition, when a small amount of an environmental controlled substance is distilled off, it is useful to azeotropy with a solvent having the same boiling point as the solvent in order to improve efficiency. Further, in the case of containing a compound having radical polymerizability, it is possible to remove by distillation under reduced pressure after adding a polymerization inhibitor so as to suppress the occurrence of crosslinking between molecules due to radical polymerization reaction in the removal by distillation under reduced pressure. These distillation removal methods can be performed at any stage of a raw material stage, a stage of a product (for example, a resin solution after polymerization and a polyfunctional monomer solution) obtained by reacting raw materials, a stage of a coloring composition produced by mixing these compounds, or the like.
Infrared absorbent
The coloring composition of the present invention may further contain an infrared absorber. For example, in the case of forming an infrared transmission filter using the coloring composition of the present invention, the wavelength of light transmitted through a film obtained by containing an infrared absorber in the coloring composition can be shifted to the longer wavelength side. The infrared absorber is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm. The infrared absorber is preferably a compound having a maximum absorption wavelength in a range exceeding 700nm and 1800nm or less. And the absorbance A of the infrared absorbent at a wavelength of 500nm 1 And absorbance A at maximum absorption wavelength 2 Is preferably A 1 /A 2 Is 0.08 or less, more preferably 0.04 or less.
Examples of the infrared absorbing agent include pyrrolopyrrole compounds, cyanine compounds, squaric acid compounds, phthalocyanine compounds, naphthalocyanine compounds, squarerene compounds, merocyanine compounds, ketone onium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrrolylene compounds, methine azo compounds, anthraquinone compounds, dibenzofuranone compounds, dithioene metal complexes, metal oxides, and metal borides. As the pyrrolopyrrole compound, there can be mentioned Examples of the compounds include compounds described in paragraphs 0016 to 0058 of JP 2009-263614, compounds described in paragraphs 0037 to 0052 of JP 2011-068731, and compounds described in paragraphs 0010 to 0033 of International publication No. 2015/166873. Examples of the squaric acid compound include a compound described in paragraphs 0044 to 0049 of Japanese patent application laid-open No. 2011-208101, a compound described in paragraphs 0060 to 0061 of Japanese patent application laid-open No. 6065169, a compound described in paragraph 0040 of International publication No. 2016/181987, a compound described in Japanese patent application laid-open No. 2015-176046, a compound described in paragraph 0072 of International publication No. 2016/190162, a compound described in paragraphs 0196 to 0228 of Japanese patent application laid-open No. 2016-074649, a compound described in paragraph 0124 of Japanese patent application laid-open No. 2017-067963, a compound described in International publication No. 2017/135359, a compound described in Japanese patent application laid-open No. 2016-114956, a compound described in International publication No. 2016/120166, and the like. Examples of the cyanine compound include a compound described in paragraphs 0044 to 0045 of JP-A2009-108267, a compound described in paragraphs 0026 to 0030 of JP-A2002-194040, a compound described in JP-A2015-17204, a compound described in JP-A2015-172102, a compound described in JP-A2008-088426, a compound described in paragraph 0090 of International publication No. 2016/190162, and a compound described in JP-A2017-031394. Examples of the Ketone onium compound include those described in Japanese patent application laid-open No. 2017-081029. Examples of the ammonium compound include a compound described in japanese patent application laid-open publication No. 2008-528706, a compound described in japanese patent application laid-open publication No. 2012-012999, a compound described in japanese patent application laid-open publication No. 2007-092060, and a compound described in paragraphs 0048 to 0063 of international publication No. 2018/043564. Examples of the phthalocyanine compound include a compound described in paragraph 0093 of JP 2012-077153A, oxytitanium phthalocyanine described in JP 2006-343631A, and JP 2013-195480A The compounds described in paragraphs 0013 to 0029, the vanadium phthalocyanine compounds described in patent publication No. 6081771, the vanadium phthalocyanine compounds described in International publication No. 2020/071486, and the phthalocyanine compounds described in International publication No. 2020/071470. Examples of the naphthalocyanine compound include a compound described in paragraph 0093 of Japanese patent application laid-open No. 2012-077153. Examples of the dithioene metal complex include compounds described in Japanese patent application No. 5733804. Examples of the metal oxide include indium tin oxide, antimony tin oxide, zinc oxide, al-doped zinc oxide, fluorine-doped tin oxide, niobium-doped titanium oxide, and tungsten oxide. For the details of tungsten oxide, refer to paragraph 0080 of Japanese patent application laid-open No. 2016-006476, which is incorporated herein by reference. Examples of the metal boride include lanthanum boride. As the lanthanum boride commercial product, there can be mentioned LaB 6 F (JAPAN NEW METALS CO., LTD) and the like. Further, as the metal boride, a compound described in international publication No. 2017/119394 can be used. As a commercially available product of indium tin oxide, F-ITO (DOWA HOLDINGS CO., LTD) and the like can be given.
And, as an infrared ray absorber, the squaric acid compound described in Japanese patent application laid-open No. 2017-197437, the squaric acid compound described in Japanese patent application laid-open No. 2017-025311, the squaric acid compound described in International publication No. 2016/154782, the squaric acid compound described in Japanese patent application laid-open No. 5884953, the squaric acid compound described in Japanese patent application laid-open No. 6036689, the squaric acid compound described in Japanese patent application laid-open No. 5810604, the squaric acid compound described in paragraphs 0090 to 0107 of International publication No. 2017/213047, the pyrrole ring-containing compound described in paragraphs 0019 to 0075 of Japanese patent application laid-open No. 2018-054760, the pyrrole ring-containing compound described in paragraphs 0078 to 0082 of Japanese patent application laid-open No. 2018-040955, the pyrrole ring-containing compound the azole ring-containing compound described in paragraphs 0043 to 0069 of JP-A2018-002773, the squaric acid compound having an aromatic ring at the amide α -position described in paragraphs 0024 to 0086 of JP-A2018-0411, the amide-linked squaric acid compound described in JP-A2017-179131, the pyrrole-bis-squaric acid skeleton or Ketone onium skeleton-containing compound described in JP-A2017-141215, the dihydroxycarbazole-bis-squaric acid compound described in JP-A2017-081029, the asymmetric compound described in paragraphs 0027 to 0114 of JP-A2017-068120, the pyrrole-ring-containing compound (carbazole-type) described in JP-A2017-067963, the phthalocyanine compound described in JP-A6251530, and the like.
The content of the infrared absorber in the total solid content of the coloring composition is preferably 1 to 40 mass%. The lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, and still more preferably 10% by mass or more. The upper limit is preferably 30 mass% or less, more preferably 25 mass% or less. The coloring composition of the present invention may contain only 1 kind of infrared absorber, or may contain 2 or more kinds. When the infrared absorbing agent is contained in an amount of 2 or more, the total amount thereof is preferably within the above range.
Pigment derivatives
The coloring composition of the present invention can contain a pigment derivative. Pigment derivatives are used, for example, as dispersing aids. Examples of the pigment derivative include a compound having a structure in which an acid group or a basic group is bonded to a pigment skeleton.
Examples of the pigment skeleton constituting the pigment derivative include a quinoline pigment skeleton, a benzimidazolone pigment skeleton, a benzisothiazole pigment skeleton, a benzothiazole pigment skeleton, an ammonium (iminium) pigment skeleton, a bone squaric acid pigment skeleton, a Ketone onium pigment skeleton, an oxonol pigment skeleton, a pyrrolopyrrole pigment skeleton, a diketopyrrolopyrrole pigment skeleton, an azo pigment skeleton, a methine azo pigment skeleton, a phthalocyanine pigment skeleton, a naphthalocyanine pigment skeleton, an anthraquinone pigment skeleton, a quinacridone pigment skeleton, a dioxazine pigment skeleton, a cyclic ketone (perinone) pigment skeleton, a perylene pigment skeleton, a thioindigo pigment skeleton, an isoindoline pigment skeleton, an isoindolinone pigment skeleton, a quinophthalone pigment skeleton, an ammonium pigment skeleton, a dithiol pigment skeleton, a triarylmethane pigment skeleton, and a pyrrolomethane pigment skeleton.
Examples of the acid group include a carboxyl group, a sulfonic acid group, a phosphoric acid group, a boric acid group, a carboxylic acid amide group, a sulfonic acid amide group, an imide group, and salts thereof. Examples of the atoms or groups of atoms constituting the salt include alkali metal ions (Li + 、Na + 、K + Etc.), alkaline earth metal ions (Ca) 2+ 、Mg 2+ Etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ions, etc. As the carboxylic acid amide group, those composed of-NHCOR are preferable X1 A group represented by the formula (I). As the sulfonic acid amide group, those composed of-NHSO are preferable 2 R X2 A group represented by the formula (I). As the imide group, a group consisting of-SO is preferable 2 NHSO 2 R X3 、-CONHSO 2 R X4 、-CONHCOR X5 or-SO 2 NHCOR X6 Represented groups, more preferably-SO 2 NHSO 2 R X3 。R X1 ～R X6 Each independently represents an alkyl group or an aryl group. R is R X1 ～R X6 The alkyl group and the aryl group may have a substituent. The substituent is preferably a halogen atom, more preferably a fluorine atom.
Examples of the basic group include an amino group, a pyridyl group and salts thereof, and salts of an ammonium group and a phthalimidomethyl group. Examples of the atoms or groups of atoms constituting the salt include hydroxide ion, halide ion, carboxylate ion, sulfonate ion, and phenoxy ion.
Pigment derivatives having excellent visible transparency (hereinafter, also referred to as transparent pigment derivatives) can also be used as pigment derivatives. The maximum value of the molar absorptivity (. Epsilon.max) of the transparent pigment derivative in the wavelength region of 400 to 700nm is preferably 3000 L.mol -1 ·cm -1 Hereinafter, it is more preferably 1000 L.mol -1 ·cm -1 Hereinafter, it is more preferably 100 L.mol -1 ·cm -1 The following is given. The lower limit of εmax is, for example, 1L mol -1 ·cm -1 Above, it may be 10 L.mol -1 ·cm -1 The above.
As a specific example of the pigment derivative, there is provided, examples of the compounds include those described in examples described later, 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, and International publication No. 2011/024896 in the 0086-0098 the diketopyrrolopyrrole compound having a thiol linkage group described in International publication No. 2015-081972, no. 5299151, no. 2015-172732, no. 2014-199308, no. 2014-085562, no. 2014-035351, no. 2008-081565, and No. 2020/002106 are disclosed in paragraphs 0063-0094, no. 2017/038252, no. 0171, no. 0172-0171, no. 2011-252065, no. 2003-081972, no. 5299151, no. 2015-172732, no. 2014-035565, and the compounds described in the publication No. 2008-081565. Further, as the pigment derivative, a compound described in paragraph 0281 of International publication No. 2021/215133 can also be used.
The content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 2 to 15 parts by mass, and even more preferably 4 to 10 parts by mass, relative to 100 parts by mass of the pigment.
The content of the pigment derivative is preferably 5 to 50 parts by mass, more preferably 10 to 40 parts by mass, and even more preferably 15 to 30 parts by mass, based on 100 parts by mass of the compound Y.
The pigment derivative may be used in an amount of 1 or 2 or more. When 2 or more kinds are used in combination, the total of them is preferably within the above range.
Polyalkylene imines
The coloring composition of the present invention may contain a polyalkyleneimine. The polyalkyleneimines are used, for example, as dispersing assistants for pigments. The dispersion aid means a material for improving the dispersibility of the pigment in the coloring composition. The polyalkyleneimine means a polymer obtained by ring-opening polymerization of an alkyleneimine. The polyalkyleneimine is preferably a polymer having a branched structure containing a primary amino group, a secondary amino group and a tertiary amino group, respectively. The number of carbon atoms of the alkylene imine is preferably 2 to 6, more preferably 2 to 4, further preferably 2 or 3, particularly preferably 2.
The molecular weight of the polyalkyleneimine is preferably 200 or more, more preferably 250 or more. The upper limit is preferably 100000 or less, more preferably 50000 or less, further preferably 10000 or less, particularly preferably 2000 or less. In addition, regarding the value of the molecular weight of the polyalkyleneimine, in the case where the molecular weight can be calculated from the structural formula, the molecular weight of the polyalkyleneimine is a value calculated from the structural formula. On the other hand, in the case where the molecular weight of a specific amine compound cannot be calculated from the structural formula or is difficult to calculate, a value of the number average molecular weight measured by the boiling point increase method is used. In addition, when measurement by the boiling point increase method is impossible or difficult, a value of the number average molecular weight measured by the viscosity method is used. In addition, when the measurement by the viscosity method is impossible or difficult, the value of the number average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography) method is used.
The amine value of the polyalkyleneimine is preferably 5mmol/g or more, more preferably 10mmol/g or more, and still more preferably 15mmol/g or more.
Specific examples of the alkylene imine include ethylene imine, propylene imine, 1, 2-butene imine, and 2, 3-butene imine, and ethylene imine and propylene imine are preferable, and ethylene imine is more preferable. The polyalkyleneimine is particularly preferably polyethyleneimine. The polyethyleneimine preferably contains 10 mol% or more of the primary amino groups, more preferably 20 mol% or more, and even more preferably 30 mol% or more of the total of the primary amino groups, the secondary amino groups, and the tertiary amino groups. Examples of commercially available polyethyleneimines include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (NIPPON SHOKUBIAI CO., LTD. Co., ltd.).
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 mass% or more, more preferably 0.5 mass% or more, and still more preferably 1 mass% or more. The upper limit is preferably 4.5 mass% or less, more preferably 4 mass% or less, and still more preferably 3 mass% or less. The content of the polyalkyleneimine is preferably 0.5 to 20 parts by mass based on 100 parts by mass of the pigment. The lower limit is preferably 0.6 parts 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. The polyalkyleneimine may be used in an amount of 1 or 2 or more. When 2 or more kinds are used, the total amount of them is preferably within the above range.
Curing accelerator
The coloring composition of the present invention may contain a curing accelerator. Examples of the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generating agents, isocyanate compounds, alkoxysilane compounds, and onium salt compounds. Specific examples of the curing accelerator include a compound described in paragraph 0094 to 0097 of Japanese patent application laid-open No. 2018/056189, a compound described in paragraphs 0246 to 0253 of Japanese patent application laid-open No. 2015-034963, a compound described in paragraphs 0186 to 0251 of Japanese patent application laid-open No. 2013-041115, an ionic compound described in Japanese patent application laid-open No. 2014-055114, a compound described in paragraphs 0071 to 0080 of Japanese patent application laid-open No. 2012-150180, an alkoxysilane compound having an epoxy group described in Japanese patent application laid-open No. 2011-253054, a compound described in paragraphs 0085 to 0092 of Japanese patent application laid-open No. 5765059, and a carboxyl group-containing epoxy curing agent described in Japanese patent application laid-open No. 2017-036379. The content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 to 8.9 mass%, more preferably 0.8 to 6.4 mass%.
Ultraviolet absorber
The coloring composition of the present invention may contain an ultraviolet absorber. As the ultraviolet absorber, conjugated diene compounds, amino diene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyl triazine compounds, indole compounds, triazine compounds, and the like can be used. Specific examples of these compounds include those described in paragraphs 0038 to 0052 of JP 2009-2174221, paragraphs 0052 to 0072 of JP 2012-208374, paragraphs 0317 to 0334 of JP 2013-068814, and paragraphs 0061 to 0080 of JP 2016-162946, which are incorporated herein by reference. Specific examples of the ultraviolet absorber include compounds having the following structures. Examples of the commercial products of the ultraviolet absorber include UV-503 (DAITO CHEMICAL CO., LTD.), tinuvin series manufactured by BASF corporation, uvinul series, sumika Chemtex Company, sumisorb series manufactured by Limited, and the like. Examples of the benzotriazole compound include the MIYOSHI OIL & FAT co, ltd. The ultraviolet absorber may be any of those described in paragraphs 0049 to 0059 of Japanese patent application laid-open No. 6268967, those described in paragraphs 0059 to 0076 of International publication No. 2016/181987, and those described in International publication No. 2020/137819.
[ chemical formula 29]
The content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. In the present invention, the ultraviolet absorber may be used in an amount of 1 or 2 or more. When 2 or more types are used, the total amount is preferably within the above range.
Polymerization inhibitor
The coloring composition of the present invention may contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4 '-thiobis (3-methyl-6-t-butylphenol), 2' -methylenebis (4-methyl-6-t-butylphenol), and N-nitrosophenyl hydroxylamine salts (ammonium salts, cerium salts, and the like). Among them, p-methoxyphenol is preferable. The content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass. The polymerization inhibitor may be 1 or 2 or more. In the case of 2 or more, the total amount is preferably within the above range.
Silane coupling agent
The coloring composition of the present invention may contain a silane coupling agent. In the present invention, the silane coupling agent means a silane compound having a hydrolyzable group and a functional group other than the hydrolyzable group. The hydrolyzable group is a substituent that is directly bonded to a silicon atom and can generate a siloxane bond by at least one of hydrolysis and condensation. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxy silicon group. Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryl group, a mercapto group, an epoxy group, an oxetanyl group, a amino group, a urea group, a thioether group, an isocyanate group, a phenyl group, and the like, and amino groups, a (meth) acryl group, and an epoxy group are preferable. Specific examples of the silane coupling agent include N- β -aminoethyl- γ -aminopropyl methyldimethoxysilane (Shin-Etsu Chemical Co., ltd., product name KBM-602), N- β -aminoethyl- γ -aminopropyl trimethoxysilane (Shin-Et su Chemical Co., ltd., product name KBM-603), N- β -aminoethyl- γ -aminopropyl triethoxysilane (Shin-Etsu Chemical Co., ltd., product name KBE-602), γ -aminopropyl trimethoxysilane (Shin-Etsu Chemical Co., ltd., product name KBM-903), γ -aminopropyl triethoxysilane (Shin-Etsu Chemical Co., ltd., product name KBM-903), 3-methacryloxypropyl methyldimethoxysilane (Shin-Etsu Chemical Co., ltd., product name KBM-502), 3-methacryloxypropyl trimethoxysilane (Shin-Etsu Chemical Co., ltd., product name 503). Specific examples of the silane coupling agent include compounds described in paragraphs 0018 to 0036 of japanese unexamined patent publication No. 2009-288703 and compounds described in paragraphs 0056 to 0066 of japanese unexamined patent publication No. 2009-242604, and these are incorporated herein by reference. 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 number of silane coupling agents may be 1 or 2 or more. In the case of 2 or more, the total amount is preferably within the above range.
Surfactant(s)
The coloring composition of the present invention can contain a surfactant. As the surfactant, various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone surfactant can be used. The surfactant is preferably a silicone surfactant or a fluorine surfactant. The surfactant can be any surfactant described in paragraphs 0238 to 0245 of International publication No. 2015/166779, which is incorporated herein by reference.
The fluorine content of the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. The fluorine-containing surfactant having a fluorine content within this range is effective in terms of uniformity of thickness of the coating film and liquid saving property, and also has good solubility in the coloring composition.
Examples of the fluorine-based surfactant include surfactants described in paragraphs 0060 to 0064 of JP 2014-04318 (corresponding to paragraphs 0060 to 0064 of International publication No. 2014/017669), surfactants described in paragraphs 0117 to 0132 of JP 2011-132503, and surfactants described in JP 2020-008634, which are incorporated herein by reference. Commercial products of the fluorine-based surfactant, examples thereof include 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-LM, R-41-LM, RS-43, TF-1956, RS-90, R-94, RS-72-K, DS-21 (the above is of DIC CORPORPORATION) FLUORAD FC430, FC431, FC171 (manufactured by Sumitomo 3M Limited above), SURFLON S-382, SC-101, SC-103, SC-104, SC-105, SC-1068, SC-381, SC-383, S-393, KH-40 (manufactured by AGC INC. Above), polyFox PF636, PF656, PF6320, PF6520, PF7002 (manufactured by OMNOVA SOLUTIONS INC. Above), futurent 208G, 215M, 245F, 601AD, 601ADH2, 602A, 610FM, 710FL, 710FM, 710FS, FTX-218 (manufactured by NEOS above), and the like.
The fluorine-based surfactant may preferably be an acrylic compound having a molecular structure having a functional group containing a fluorine atom, and the functional group containing a fluorine atom is partially cleaved to volatilize the fluorine atom when heat is applied. Examples of the fluorine-containing surfactant include MEGAFACE DS series (chemical industry journal of date (2016, 2, 22 days) and daily industrial news (2016, 2, 23 days)) manufactured by DIC Corporation, and MEGAFACE DS-21.
As the fluorine-based surfactant, a polymer of a vinyl ether compound containing a fluorine atom and a hydrophilic vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group is also preferably used. Examples of such a fluorine-based surfactant include those described in JP 2016-216602A, which is incorporated herein by reference.
The fluorine-based surfactant may be a block polymer. The fluorine-containing surfactant may preferably be a fluorine-containing polymer compound comprising: repeating units derived from a (meth) acrylate compound having a fluorine atom; and a repeating unit derived from a (meth) acrylate compound having 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups, propyleneoxy groups). The fluorosurfactant described in paragraphs 0016 to 0037 of JP-A2010-032698 and the following compounds are also exemplified as the fluorosurfactant used in the present invention.
[ chemical formula 30]
The weight average molecular weight of the above compound is preferably 3000 to 50000, for example 14000. In the above-mentioned compounds, the% representing the proportion of the repeating unit is mol%.
The fluorine-based surfactant may be a fluoropolymer having a group containing an ethylenically unsaturated bond in a side chain. Specific examples thereof include the compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of JP-A2010-164965, and MEGAFACE RS-101, RS-102 and RS-718K, RS-72-K manufactured by DIC Corporation. The fluorine-based surfactant may be any of those described in paragraphs 0015 to 0158 of JP-A2015-117327.
In addition, from the viewpoint of environmental control, the surfactant described in International publication No. 2020/084854 is preferably used as a substitute for a surfactant having a perfluoroalkyl group having 6 or more carbon atoms.
Furthermore, the fluoroimide salt compound represented by the formula (fi-1) is also preferably used as the surfactant.
[ chemical formula 31]
In the formula (fi-1), m represents 1 or 2, n represents an integer of 1 to 4, a represents 1 or 2, X a+ Representing a metal ion, primary ammonium ion, secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion or NH 4 + 。
Examples of the nonionic surfactant include glycerin, trimethylolpropane, trimethylolethane, ethoxylates thereof, and propoxylates thereof (for example, glycerol propoxylate, glycerol ethoxylate, and the like), 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 corporation), tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF corporation), 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 Tamoto & Fat Co., ltd.), OLFIN E1010, surfynol 104, 400, chemical Co., ltd. And the like.
Examples of the silicone surfactant include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67Additive, 74Additive, M Additive, SF 8419OIL (manufactured by Dow Toray Co., ltd.), TSF-4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials Inc., above), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., ltd., above), BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (manufactured by BYK Co., LTD), and the like.
In addition, a compound having the following structure can be used as the silicone surfactant.
[ chemical formula 32]
The content of the surfactant in the total solid content of the coloring composition is preferably 0.001 to 5.0% by mass, more preferably 0.005 to 3.0% by mass. The number of surfactants may be 1 or 2 or more. In the case of 2 or more, the total amount is preferably within the above range.
Antioxidant(s)
The coloring composition of the present invention can contain an antioxidant. Examples of the antioxidant include phenol compounds, phosphite compounds, and thioether compounds. As the phenol compound, any phenol compound called a phenol-based antioxidant can be used. Preferred examples of the phenol compound include hindered phenol compounds. Compounds having a substituent at a position adjacent to the phenolic hydroxyl group (ortho position) are preferred. The substituent is preferably a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms. The antioxidant is preferably a compound having a phenol group and a phosphite group in the same molecule. In addition, a phosphorus antioxidant can be preferably used as the antioxidant. Examples of the phosphorus antioxidant include tris [2- [ [2,4,8, 10-tetrakis (1, 1-dimethylethyl) dibenzo [ d, f ] [1,3,2] dioxaphosphepin-6-yl ] oxy ] ethyl ] amine, tris [2- [ (4, 6,9, 11-tetra-t-butyldibenzo [ d, f ] [1,3,2] dioxaphosphepin-2-yl) oxy ] ethyl ] amine, and ethyl bis (2, 4-di-t-butyl-6-methylphenyl) phosphite. Examples of the commercial products of the antioxidants include Adekastab AO-20, adekastab AO-30, adekastab AO-40, adekastab AO-50F, adekastab AO-60G, adekastab AO-80, adekastab A0-330 (manufactured by ADEKA Corporation). The antioxidant may be a compound described in paragraphs 0023 to 0048 of patent publication 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 patent publication No. 10-2019-0059371. The content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass. The antioxidant may be used in an amount of 1 or 2 or more. When 2 or more types are used, the total amount is preferably within the above range.
Other ingredients
The coloring composition of the present invention may contain a sensitizer, a curing accelerator, a filler, a thermal curing accelerator, a plasticizer, and other auxiliary agents (for example, conductive particles, an antifoaming agent, a flame retardant, a leveling agent, a peeling accelerator, a perfume, a surface tension regulator, a chain transfer agent, and the like) as needed. The properties such as film physical properties can be adjusted by appropriately containing these components. For these components, for example, reference can be made to the descriptions of paragraphs 0183 and later of japanese patent application laid-open publication No. 2012-003225 (paragraph 0237 of the corresponding us patent application publication No. 2013/0034812), the descriptions of paragraphs 0101 to 0104 and 0107 to 0109 of japanese patent application laid-open publication No. 2008-250074, and the like, and these contents are incorporated into the present specification. Further, the coloring composition of the present invention may contain a latent antioxidant as required. As the latent antioxidant, a compound in which a site functioning as an antioxidant is protected with a protecting group and the protecting group is detached by heating at 100 to 250 ℃ or heating at 80 to 200 ℃ in the presence of an acid/base catalyst and functions as an antioxidant is exemplified. Examples of the latent antioxidant include compounds described in Japanese patent laid-open publication Nos. 2014/021023 and 2017/030005, and Japanese patent laid-open publication No. 2017-008219. Examples of commercial products of the latent antioxidant include ADEKA ARKLS GPA-5001 (manufactured by ADEKA CORPORATION).
The coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the obtained film. Examples of the metal oxide include TiO 2 、ZrO 2 、Al 2 O 3 、SiO 2 Etc. The primary particle diameter of the metal oxide is preferably 1 to 100nm, more preferably 3 to 70nm, and still more preferably 5 to 50nm. The metal oxide may have a core-shell structure. In this case, the core may be hollow.
The coloring composition of the present invention may contain a light resistance improver. As the light resistance improver, a light-blocking agent, examples thereof include compounds described in paragraphs 0036 to 0037 of Japanese patent application laid-open No. 2017-198787, compounds described in paragraphs 0029 to 0034 of Japanese patent application laid-open No. 2017-146350, compounds described in paragraphs 0036 to 0037 of Japanese patent application laid-open No. 2017-129774, compounds described in paragraphs 0049 to 0052, compounds described in paragraphs 0031 to 0034 of Japanese patent application laid-open No. 2017-129674, compounds described in paragraphs 0036 to 0037 of Japanese patent application laid-open No. 2018-005803, compounds described in paragraphs 0051 to 0054, compounds described in paragraphs 0025 to 0039 of International patent application laid-open No. 2017/164127, compounds described in paragraphs 0034 to 0047 of Japanese patent application laid-open No. 2017-186546, compounds described in paragraphs 0039 to 0041 of Japanese patent application laid-open No. 2017-025116, compounds described in paragraphs 20151 to 2015, compounds described in paragraphs 2015 to 20116, and compounds described in paragraphs 2015 to 20116, and compounds described in paragraphs 20116 to 20116.
The coloring composition of the present invention also preferably contains substantially no terephthalate. The term "substantially not including" as used herein means that the content of terephthalic acid ester in the total amount of the coloring composition is 1000 ppb by mass or less, more preferably 100 ppb by mass or less, and particularly preferably zero.
From the viewpoint of environmental regulations, the use of perfluoroalkyl sulfonic acids and salts thereof, and perfluoroalkyl carboxylic acids and salts thereof, is sometimes regulated. In the coloring composition of the present invention, when the content of the above-mentioned compound is reduced, the content of the perfluoroalkylsulfonic acid (particularly, the perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and the salt thereof, and the perfluoroalkylcarboxylic acid (particularly, the perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and the salt thereof are preferably in the range of 0.01ppb to 1,000 ppb, more preferably in the range of 0.05ppb to 500ppb, and even more preferably in the range of 0.1ppb to 300ppb, relative to the total solid content of the coloring composition. The coloring composition of the present invention may contain substantially no perfluoroalkylsulfonic acid or salt thereof, and no perfluoroalkylcarboxylic acid or salt thereof. For example, by using a compound capable of becoming a substitute for a perfluoroalkylsulfonic acid and a salt thereof and a compound capable of becoming a substitute for a perfluoroalkylcarboxylic acid and a salt thereof, a coloring composition containing substantially no perfluoroalkylsulfonic acid and salt thereof and no perfluoroalkylcarboxylic acid and salt thereof can be selected. Examples of the compound that can be substituted for the controlled compound include compounds that are removed from the controlled object by the difference in the number of carbon atoms in the perfluoroalkyl group. However, the use of perfluoroalkylsulfonic acids and salts thereof, and perfluoroalkylcarboxylic acids and salts thereof is not hindered by the foregoing. The coloring composition of the present invention may contain a perfluoroalkylsulfonic acid and a salt thereof, and a perfluoroalkylcarboxylic acid and a salt thereof, within the maximum allowable range.
The water content of the coloring composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably 0.1 to 1.0% by mass. The water content can be measured by the karl fischer method.
The coloring composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface shape (flatness, etc.), adjusting the film thickness, etc. The viscosity value can be appropriately selected according to need, but is preferably 0.3 to 50 mPas, more preferably 0.5 to 20 mPas, for example, at 25 ℃. As a method for measuring the viscosity, for example, a cone-plate type viscometer can be used to measure the viscosity in a state where the temperature is adjusted to 25 ℃.
Container (containing vessel)
The container for the coloring composition is not particularly limited, and a known container can be used. In addition, as the storage container, a multilayer bottle having 6 kinds of 6 layers of resins constituting the inner wall of the container or a bottle having 6 kinds of resins in a 7-layer structure is preferably used in order to suppress the mixing of impurities into the raw material or the coloring composition. Examples of such a container include those described in Japanese patent application laid-open No. 2015-123351. Further, the inner wall of the container is preferably made of glass, stainless steel, or the like for the purpose of preventing elution of metal from the inner wall of the container, improving the storage stability of the coloring composition, suppressing deterioration of components, or the like.
< method for producing coloring composition >
The coloring composition of the present invention can be prepared by mixing the ingredients. In the preparation of the coloring composition, all the components may be dissolved and/or dispersed in a solvent at the same time to prepare the coloring composition, or if necessary, the components may be appropriately used as 2 or more solutions or dispersions, and these may be mixed at the time of use (at the time of coating) to prepare the coloring composition.
In addition, in the preparation of the coloring composition, a process for dispersing the pigment is preferably included. Examples of the mechanical force used for dispersing the pigment in the process of dispersing the pigment include compression, extrusion, impact, shearing, cavitation, and the like. Specific examples of these processes include bead milling, sand milling, roll milling, ball milling, paint agitators, microfluidics, high-speed impellers, sand mixing, flow jet mixing, high-pressure wet micronization, ultrasonic dispersion, and the like. In the pulverization of the pigment by sanding (bead grinding), it is preferable to perform the treatment under such a condition that the pulverization efficiency is improved by using the microbeads having a small diameter, and by improving the filling ratio of the microbeads, or the like. Further, it is preferable to remove coarse particles by filtration, centrifugal separation, or the like after the pulverization treatment. The process and the dispersing machine for dispersing the pigment can be preferably those described in paragraph 0022 of "the entire collection of dispersing techniques, JOHOKIKO co., ltd. Release, 7.15 th year in 2005" or "the integrated data set of dispersion techniques and practical applications on the industrial scale, release by the department of business development center, 10.10 th year in 1978", and japanese patent application laid-open No. 2015-157893. In the step of dispersing the pigment, the fine particles may be subjected to a salt milling step. For example, the materials, equipment, process conditions, etc. used in the salt milling step are described in japanese patent application laid-open No. 2015-194521 and japanese patent application laid-open No. 2012-046629.
In preparing the coloring composition, the coloring composition is preferably filtered by a filter in order to remove impurities, reduce defects, or the like. The filter may be used without any particular limitation as long as it is a filter conventionally used for filtration applications and the like. Examples of the filter include filters using a material such as a fluororesin such as Polytetrafluoroethylene (PTFE) or polyvinylidene fluoride (PVDF), a polyamide resin such as nylon (for example, nylon-6 or nylon-6, 6), a polyolefin resin such as polyethylene or polypropylene (PP) (including a high-density and ultrahigh-molecular-weight polyolefin resin). Among these materials, polypropylene (including high density polypropylene) and nylon are preferred.
The pore diameter of the filter is preferably 0.01 to 7.0. Mu.m, more preferably 0.01 to 3.0. Mu.m, still more preferably 0.05 to 0.5. Mu.m. If the pore diameter of the filter is in the above range, fine impurities can be removed more reliably. As regards the pore size value of the filter, reference can be made to the filter manufacturer nominal value. As the filter, various filters provided by NIHON PALL Corporation (DFA 4201NXEY, DFA4201NAEY, DFA4201J006P, etc.), advantec Toyo Kaisha, ltd., nihon Entegris k.k. (Formerly Nippon Mykrolis Corporation), KITZ MICROFILTER Corporation, etc. can be used.
Also, a fibrous filter material is preferably used as the filter. Examples of the fibrous filter media include polypropylene fibers, nylon fibers, and glass fibers. Examples of the commercial products include ROKI TECHNO CO, SBP type series (SBP 008, etc.), TPR type series (TPR 002, TPR005, etc.), SHPX type series (SHPX 003, etc.) manufactured by LTD.
When filters are used, different filters (e.g., filter 1 and filter 2, etc.) may be combined. In this case, the filtration with each filter may be performed only 1 time, or may be performed 2 times or more. Also, filters of different pore diameters may be combined within the above range. The dispersion may be filtered by the 1 st filter alone, and after mixing other components, the dispersion may be filtered by the 2 nd filter. And, the filter can be appropriately selected according to the hydrophilicity and hydrophobicity of the composition.
< film >
The film of the present invention is a film obtained from the above-described coloring composition of the present invention. The film of the present invention can be used for a filter such as a color filter or an infrared ray transmission filter.
The film thickness of the film of the present invention can be appropriately adjusted according to the purpose. For example, the film thickness is preferably 20 μm or less, more preferably 10 μm or less, and further preferably 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and still more preferably 0.3 μm or more.
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, magenta, or yellow, more preferably has a hue of green, red, or yellow. Also, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of the coloring pixel include a red pixel, a green pixel, a blue pixel, a magenta pixel, a cyan pixel, and a yellow pixel, and the coloring pixel is preferably a red pixel, a green pixel, and a yellow pixel, more preferably a red pixel or a green pixel, and further preferably a green pixel.
In the film of the present invention, the light transmittance is preferably 50% in the wavelength range of 470 to 520nm, more preferably 475 to 520nm, and even more preferably 480 to 520 nm. The light transmittance is preferably 50% in the wavelength range of 470 to 520nm and 575 to 625nm, respectively. In this embodiment, the wavelength on the short wavelength side at which the transmittance becomes 50% is preferably present in the wavelength range of 475 to 520nm, and more preferably in the wavelength range of 480 to 520 nm. The wavelength on the long wavelength side at which the transmittance is 50% is preferably in the wavelength range of 580 to 620nm, and more preferably in the wavelength range of 585 to 615 nm. A film having such spectral characteristics can be preferably used as a green pixel.
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 spectral characteristics (1) to (4) below, for example.
(1): the maximum value of the light transmittance in the thickness direction of the film in the wavelength range of 400 to 640nm 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 1300nm is 70% or more (preferably 75% or more, more preferably 80% or more). The film having such spectral characteristics can block light having a wavelength in the range of 400 to 640nm and transmit light having a wavelength exceeding 700 nm.
(2): a film having a maximum value of light transmittance in the thickness direction of the film in a wavelength range of 400 to 750nm of 20% or less (preferably 15% or less, more preferably 10% or less) and a minimum value of light transmittance in the thickness direction of the film in a wavelength range of 900 to 1300nm of 70% or more (preferably 75% or more, more preferably 80% or more). The film having such spectral characteristics can block light having a wavelength in the range of 400 to 750nm and transmit light having a wavelength exceeding 850 nm.
(3): a film having a maximum value of light transmittance in the thickness direction of the film in a wavelength range of 400 to 830nm of 20% or less (preferably 15% or less, more preferably 10% or less) and a minimum value of light transmittance in the thickness direction of the film in a wavelength range of 1000 to 1300nm of 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 830nm and transmit light exceeding 940 nm.
(4): a film having a maximum value of light transmittance in the thickness direction of the film in a wavelength range of 400 to 950nm of 20% or less (preferably 15% or less, more preferably 10% or less) and a minimum value of light transmittance in the thickness direction of the film in a wavelength range of 1100 to 1300nm of 70% or more (preferably 75% or more, more preferably 80% or more). The film having such spectral characteristics can block light having a wavelength in the range of 400 to 950nm and transmit light having a wavelength exceeding 1040 nm.
< method for producing film >
Next, a method for producing the film of the present invention will be described. The film of the present invention can be produced through a process of coating the coloring composition of the present invention. The method for producing a film preferably further includes a step of forming a pattern (pixel). As a method for forming a pattern (pixel), photolithography and dry etching are mentioned, and photolithography is preferable.
The patterning by photolithography preferably includes the steps of: a step of forming a coloring composition layer on a support using the coloring composition of the present invention; exposing the colored composition layer to light in a pattern; 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 (pixels) (post-baking step) may be provided.
In the step of forming the coloring composition layer of the present invention, the coloring composition layer is formed on the support using the coloring composition. The support is not particularly limited, and may be appropriately selected according to the application. For example, a glass substrate, a silicon substrate, or the like is given, and a silicon substrate is preferable. Further, a Charge Coupled Device (CCD), a Complementary Metal Oxide Semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate. A black matrix (black matrix) may be formed on the silicon substrate to isolate each pixel. In addition, a base layer may be provided on the silicon substrate in order to improve adhesion to the upper layer, prevent diffusion of substances, or planarize the substrate surface. The underlayer may be formed using a composition for removing a colorant from the coloring composition described in the present specification, a composition containing a curable compound, a surfactant, or the like described in the present specification, or the like. The surface contact angle of the underlayer is preferably 20 to 70 ° when measured with diiodomethane. And, it is preferably 30 to 80 ° when measured with water.
As a method for applying the coloring composition, a known method can be used. For example, a dropping method (droplet coating) is mentioned; a slit coating method; spraying; roll coating; spin coating (spin coating); a casting coating method; slit spin coating; prewet (for example, a method described in japanese patent application laid-open No. 2009-145395); inkjet (e.g., on-demand, piezo, thermal), jet printing such as nozzle jetting, flexography, screen printing, gravure, reverse offset, metal mask printing, and the like; a transfer method using a mold or the like; nanoimprint method, and the like. The method of application to inkjet is not particularly limited, and examples thereof include methods described in "unlimited possibility in inkjet-patents that can be popularized and used," release under 2005, month 2, sumitbe Techon Research co., ltd. "and (especially, pages 115 to 133), japanese patent application laid-open publication nos. 2003-262626716, 2003-185831, 2003-261827, 2012-126830, 2006-169325, and the like. The method of applying the coloring composition can be described in international publication nos. 2017/030174 and 2017/018419, and these are incorporated herein by reference.
The layer of the coloring composition formed on the support may be dried (prebaked). In the case of manufacturing a film by a low temperature process, the pre-baking may not be performed. In the case of performing the prebaking, the prebaking temperature is preferably 150 ℃ or less, more preferably 120 ℃ or less, and further preferably 110 ℃ or less. The lower limit may be, for example, 50℃or higher, or 80℃or higher. The pre-baking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, still more preferably 80 to 220 seconds. The prebaking can be performed with a hot plate, an oven, or the like.
Next, the coloring composition layer is exposed to light in a pattern (exposure step). For example, the coloring composition layer can be exposed to light in a pattern shape by using a stepper, a scanner, or the like through a mask having a predetermined mask pattern. Thereby, the exposed portion can be cured.
Examples of radiation (light) that can be used for exposure include g-rays and i-rays. Light having a wavelength of 300nm or less (preferably, light having a wavelength of 180 to 300 nm) can also be used. Examples of light having a wavelength of 300nm or less include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm), and KrF rays (wavelength 248 nm) are preferable. Further, a light source having a long wavelength of 300nm or more can be used.
In the exposure, light may be continuously irradiated to perform exposure, or pulse irradiation may be performed to perform exposure (pulse exposure). The pulse exposure is an exposure method in which light is repeatedly irradiated and suspended in a short period of time (for example, in the order of milliseconds or less) to perform exposure.
The irradiation amount (exposure amount) is preferably, for example, 0.03 to 2.5J/cm 2 More preferably 0.05 to 1.0J/cm 2 . The oxygen concentration at the time of exposure can be appropriately selected, and in addition to the exposure to the atmosphere, for example, exposure may be performed in a low oxygen environment (for example, 15 vol%, 5 vol%, or substantially no oxygen) having an oxygen concentration of 19 vol% or less, or exposure may be performed in a high oxygen environment (for example, 22 vol%, 30 vol%, or 50 vol%) having an oxygen concentration of more than 21 vol%. The exposure illuminance can be set appropriately, and can be generally from 1000W/m 2 ～100000W/m 2 (e.g., 5000W/m 2 、15000W/m 2 Or 35000W/m 2 ) Is selected from the range of (a). The oxygen concentration and the exposure illuminance may be appropriately combined, and for example, the oxygen concentration may be set to 10% by volume and the illuminance 10000W/m 2 Oxygen concentration of 35% by volume and illuminance of 20000W/m 2 Etc.
Then, the unexposed portions of the coloring composition layer are removed by development to form a pattern (pixel). The development and removal of the unexposed portion of the coloring composition layer can be performed using a developer. Thus, the coloring composition layer in the unexposed portion in the exposure step is dissolved in the developer, and only the photo-cured portion remains. The temperature of the developer is preferably 20 to 30 ℃. The development time is preferably 20 to 180 seconds. In order to improve the residue removing property, the step of throwing away the developer at 60 second intervals to supply a new developer may be repeated.
The developer may be an organic solvent, an alkaline developer, or the like, and an alkaline developer is preferably used. As the alkaline developer, an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable. Examples of the alkaline agent include organic alkaline compounds such as ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine (diglycolamine), diethanolamine, hydroxylamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethyl bis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1, 8-diazabicyclo- [5.4.0] -7-undecene, and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate, and sodium metasilicate. The alkaline agent is preferably a compound having a large molecular weight in terms of environment and safety. The concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass. The developer may further contain a surfactant. From the viewpoint of convenience in transportation or storage, the developer may be temporarily prepared as a concentrated solution, and diluted to a desired concentration at the time of use. The dilution ratio is not particularly limited, and can be set in a range of 1.5 to 100 times, for example. Further, it is also preferable to perform washing (rinsing) with pure water after development. Further, it is preferable to perform the rinsing by rotating the support on which the developed coloring composition layer has been formed and supplying the rinse liquid to the developed coloring composition layer. Further, it is also preferable that the discharge of the rinse liquid is performed by moving the nozzle from the center portion of the support body to the peripheral portion of the support body. In this case, when moving from the center portion to the peripheral portion of the support body of the nozzle, the movement speed of the nozzle may be gradually reduced and the nozzle may be moved. By performing flushing in this manner, in-plane deviation of flushing can be suppressed. The same effect can be obtained by gradually decreasing the rotation speed of the support body while moving the nozzle from the center portion to the peripheral portion of the support body.
Preferably, after development, drying is performed, and then additional exposure treatment and heat treatment (post baking) are performed. The post-exposure treatment and post-baking are post-development curing treatments for producing a complete cured product. The heating temperature in the post baking is, for example, preferably 100 to 240 ℃, more preferably 200 to 240 ℃. The developed film may be post-baked continuously or batchwise using a heating mechanism such as a hot plate, a convection oven (heated air circulation dryer), or a high-frequency heater so as to satisfy the above conditions. In the case of performing the additional exposure treatment, the light used for the exposure is preferably light having a wavelength of 400nm or less. The additional exposure treatment may be performed by the method described in korean laid-open patent No. 10-2017-012130.
The patterning by the dry etching method preferably includes the steps of: forming a coloring composition layer on a support using the coloring composition of the present invention, and curing the entire coloring composition layer to form a cured product layer; forming a photoresist layer on the cured layer; exposing the photoresist layer to a pattern, and developing to form a resist pattern; and dry etching the cured layer using the resist pattern as a mask and an etching gas. When forming the resist layer, a pre-bake treatment is preferably further performed. In particular, as a process for forming the resist layer, a form in which a post-exposure heat treatment and a post-development heat treatment (post-baking treatment) are performed is preferable. For pattern formation by the dry etching method, reference can be made to paragraphs 0010 to 0067 of Japanese patent application laid-open No. 2013-064993, and this is incorporated herein by reference.
< Filter >
The optical filter of the present invention has the film of the present invention described above. Examples of the type of the filter include a color filter and an infrared ray transmission filter, and a color filter is preferable. As the color filter, a colored pixel having the film of the present invention as a color filter is preferable.
The optical filter may be provided with a protective layer on the surface of the film of the present invention. By providing the protective layer, oxidation resistance, low reflection, hydrophilic and hydrophobic properties can be imparted to the filmShielding of light of a wavelength (ultraviolet rays, near infrared rays, etc.), and the like. The thickness of the protective layer is preferably 0.01 to 10. Mu.m, more preferably 0.1 to 5. Mu.m. Examples of the method for forming the protective layer include a method of coating a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of adhering a molded resin with an adhesive. Examples of the component constituting the protective layer include (meth) acrylic resin, alkene-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, alkyd resin, epoxy resin, modified silicone resin, fluororesin, polycarbonate resin, polyacrylonitrile resin, cellulose resin, si, C, W, al 2 O 3 、Mo、SiO 2 、Si 2 N 4 And the like, two or more of these components may 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, siO 2 Si (Si) 2 N 4 . In the case of the protective layer for reducing reflection, the protective layer preferably contains a (meth) acrylic resin and a fluororesin.
In the case of forming the protective layer by applying the resin composition, a known method such as spin coating, casting, screen printing, or ink jet method can be used as a method for applying the resin composition. The organic solvent contained in the resin composition may be any known organic solvent (for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.). In the case of forming the protective layer by a chemical vapor deposition method, a known chemical vapor deposition method (thermal chemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method) can be used as the chemical vapor deposition method.
The protective layer may contain organic or inorganic fine particles, an absorber of light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjuster, an antioxidant, an adhesive, a surfactant, and other additives, as required. Examples of the organic and inorganic fine particles include polymer fine particles (e.g., silicone fine particles, polystyrene fine particles, melamine fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride, magnesium fluoride, hollow silica, calcium carbonate, barium sulfate, and the like. The absorber for light of a specific wavelength can be a known absorber. The content of these additives can be appropriately adjusted, but is preferably 0.1 to 70 mass%, more preferably 1 to 60 mass% with respect to the total mass of the protective layer.
Further, as the protective layer, the protective layers described in paragraphs 0073 to 0092 of Japanese patent application laid-open No. 2017-151176 can be used.
The filter may also have the following structure: each pixel is embedded in a space partitioned by a partition wall, for example, in a grid shape.
< solid-state imaging element >
The solid-state imaging device of the present invention has the film of the present invention described above. The structure of the solid-state imaging device is not particularly limited as long as the structure includes the film of the present invention and functions as the solid-state imaging device, and examples thereof include the following.
The structure of the image pickup element is as follows: the substrate has a transfer electrode composed of a plurality of photodiodes and polysilicon or the like constituting a light receiving region of a solid-state imaging element (a CCD (charge coupled device) image sensor, a CMOS (complementary metal oxide film semiconductor) image sensor or the like), a light shielding film having only a light receiving portion opening of the photodiodes is provided on the photodiodes and the transfer electrode, an element protection film composed of silicon nitride or the like is provided on the light shielding film so as to cover the entire surface of the light shielding film and the light receiving portion of the photodiodes, and a color filter is provided on the element protection film. The device protection film may have a light condensing mechanism (e.g., a microlens, etc. hereinafter, the same applies) on the lower side (side close to the substrate) of the color filter, or may have a light condensing mechanism on the color filter. The color filter may have the following structure: each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid shape. In this case, the refractive index of the partition wall is preferably lower than that of each colored pixel. Examples of the imaging device having such a configuration include those described in japanese patent application laid-open publication No. 2012-227478, japanese patent application laid-open publication No. 2014-179577, and international publication No. 2018/043654. Further, as shown in japanese patent application laid-open No. 2019-211559, the provision of an ultraviolet absorbing layer in the structure of the solid-state imaging element can also improve light resistance. An imaging device including the solid-state imaging element of the present invention can be used as a digital camera or an electronic device (such as a mobile phone) having an imaging function, as well as an in-vehicle camera or a monitoring camera.
< image display device >
The image display device of the present invention has the film of the present invention described above. Examples of the image display device include a liquid crystal display device and an organic electroluminescent display device. The definition of the image display apparatus or the details of each image display apparatus are described in, for example, "electronic display device (zozuki schiff, kogyo Chosakai Publishing co., ltd., release in 1990)", "display device (isb., sangyo Tosho Publishing co., ltd., release in 1989)", and the like. Further, the liquid crystal display device is described in "next generation liquid crystal display technology (edited in Tian Longnan, kogyo Chosakai Publishing co., ltd., 1994)", for example. The liquid crystal display device to which the present invention can be applied is not particularly limited, and can be applied to, for example, various types of liquid crystal display devices described in the "next-generation liquid crystal display technology" described above.
Examples
The present invention will be described in more detail with reference to the following examples. The materials, amounts used, ratios, treatment contents, treatment order, and the like shown in the following examples can be appropriately changed without departing from the gist of the present invention. Accordingly, the scope of the present invention is not limited to the specific examples shown below. In the structural formula shown below, me represents methyl, et represents ethyl, and Ph represents phenyl.
< synthetic example of Compound Y >
Synthesis example 1 Synthesis of Compound (Y-1)
[ chemical formula 33]
/>
To 13.9 parts by mass of the compound (a-1), 1 equivalent of the compound (b-1) and 5 parts by mass of methanol were added, and the mixture was heated and stirred at an external temperature of 65℃under a nitrogen stream for 1 hour. After cooling the liquid temperature to 30 ℃, the resulting solid was filtered off and washed with 5 parts by mass of methanol. The obtained solid was air-dried at 50℃to obtain 20.5 parts by mass of compound (S-1). Subsequently, 1 equivalent of copper acetate monohydrate (Cu (OAc)) was mixed in 10 parts by mass of the compound (S-1) 2 ) And 6 parts by mass of N-ethyl pyrrolidone (NEP), and the mixture was heated and stirred at an external temperature of 80℃under a nitrogen stream for 2 hours. Then, 13 parts by mass of ethyl acetate was added dropwise, and after stirring with heating for 30 minutes, 27 parts by mass of ethyl acetate was added dropwise, and stirring was performed with heating for 1 hour. After cooling the liquid temperature to 30 ℃, the resulting solid was filtered off and then washed with 10 parts by mass of ethyl acetate and 10 parts by mass of acetone. The obtained solid was air-dried at 50℃to obtain 11.2 parts by mass of a compound (Y-1) as a compound of a complex compound (S-1) on a copper atom. The value of (M+H) (posi) in the mass spectrum of the compound (Y-1) was 304. The maximum absorption wavelength of the compound (Y-1) is in the range of 400 to 500 nm.
Synthesis examples 2 to 44, 48, 50, 52, 56 and 87 Synthesis of Compound (Y-2) to Compound (Y-44), compound (Y-48), compound (Y-50), compound (Y-52), compound (Y-56) and Compound (Y-87)
Compounds (Y-2) to (Y-44), compound (Y-48), compound (Y-50), compound (Y-52), compound (Y-56) and compound (Y-87) were synthesized in the same manner as in Synthesis example 1 except that the compound (a-1) and the compound (b-1) in Synthesis example 1 were changed to the compounds described in the columns of the compound (a) and the compound (b) in the following tables, respectively. The compounds (Y-2) to (Y-44), the compound (Y-48), the compound (Y-50), the compound (Y-52), the compound (Y-56) and the compound (Y-87) are compounds in which copper atoms are coordinated to the compounds described in the columns of the compound S in the following table. The maximum absorption wavelengths of the compounds (Y-2) to (Y-44), the compounds (Y-48), the compounds (Y-50), the compounds (Y-52), the compounds (Y-56) and the compounds (Y-87) are in the range of 400 to 700 nm. In addition, when a compound having an amino group is used as the compound S, acetic acid and a salt used for complexation may be formed.
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) and Compound (Y-86)
The same operations as in Synthesis example 1 were performed except that the compound (a-1) and the compound (b-1) in Synthesis example 1 were changed to the compounds described in the columns of the compound (a) and the compound (b) in the following tables, and that copper acetate monohydrate was changed to zinc acetate dihydrate, and 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), and compound (Y-68) to compound (Y-86) were synthesized. The compounds (Y-45), Y-46, Y-47, Y-49, Y-51, Y-53, Y-54, Y-55, Y-57, and Y-68) to Y-86 are compounds described in columns of the compound S having zinc atoms coordinated to the following table. The maximum absorption wavelengths of the compound (Y-45), the compound (Y-46), the compound (Y-47), the compound (Y-49), the compound (Y-51), the compound (Y-53), the compound (Y-54), the compound (Y-55), the compound (Y-57), and the compound (Y-68) to the compound (Y-86) are in the range of 400 to 600 nm. In addition, when a compound having an amino group is used as the compound S, acetic acid and a salt used for complexation may be formed.
Synthesis of Compounds (Y-58) to (Y-67)
Compounds (Y-58) to (Y-67) were synthesized by performing the same operations as in Synthesis example 1 except that the compound (a-1) and the compound (b-1) in Synthesis example 1 were changed to the compounds described in the columns of the compound (a) and the compound (b) in the following tables, respectively, and that copper acetate monohydrate was changed to iron acetate, titanium tetraisopropoxide, basic aluminum acetate, tetraethyl orthosilicate or calcium acetate monohydrate. The compounds (Y-58) to (Y-67) are compounds in which a metal atom shown in one column of the metal atoms in the following table is coordinated to a compound shown in one column of the compound S in the following table. The maximum absorption wavelength of the compounds (Y-58) to (Y-67) is in the range of 400 to 600 nm. In addition, when a compound having an amino group is used as the compound S, acetic acid and a salt used for complexation may be formed.
TABLE 1
TABLE 2
TABLE 3
TABLE 4
TABLE 5
TABLE 6
TABLE 7
TABLE 8
TABLE 9
TABLE 10
TABLE 11
TABLE 12
TABLE 13
TABLE 14
TABLE 15
TABLE 16
TABLE 17
< preparation of Dispersion liquid >
The mixed solution in which the raw materials described in the following table were mixed and dispersed for 3 hours using a bead mill (zirconia microbeads having a diameter of 0.1 mm). Next, a high-pressure dispersing machine NANO-3000-10 (Nippon BEE Co., ltd.) with a pressure reducing mechanism was used at a pressure of 2000kg/cm 2 And a dispersion treatment was carried out at a flow rate of 500 g/min. The dispersion treatment was repeated 10 times in total, whereby a dispersion was obtained. In the following table, the values of the amounts of the colorants 1 to 4, the infrared-ray absorber, the pigment derivative and the dispersant in terms of solid content are values.
TABLE 18
TABLE 19
TABLE 20
TABLE 21
TABLE 22
TABLE 23
TABLE 24
TABLE 25
TABLE 26
TABLE 27
TABLE 28
TABLE 29
TABLE 30
The raw materials described by abbreviations in the above tables are as follows.
(colorant)
Y-1 to Y-87: the above-mentioned compounds Y-1 to Y-87
Yb-1: a compound of the following structure (C.I. pigment yellow 129)
[ chemical formula 34]
yy-1 to yy-4: compounds of the structure
[ chemical formula 35]
yy-11 to yy-20: compounds of the structure
[ chemical formula 36]
[ chemical formula 37]
PG36: C.I. pigment Green 36 (Phthalocyanine Compound, green pigment)
PG58: C.I. pigment Green 58 (Phthalocyanine Compound, green pigment)
PG59: C.I. pigment Green 59 (Phthalocyanine Compound, green pigment)
PG63: C.I. pigment Green 63 (Phthalocyanine Compound, green pigment)
PR254: C.I. pigment Red 254 (diketopyrrolopyrrole compounds, red pigments)
PR264: c.i. pigment red 264 (diketopyrrolopyrrole compounds, red pigments)
PR272: c.i. pigment red 272 (diketopyrrolopyrrole compounds, red pigments)
PY139: C.I. pigment yellow 139 (isoindoline compound, yellow pigment)
PY150: C.I. pigment yellow 150 (azo compound, yellow pigment)
PY155: c.i. pigment yellow 155 (azo compound, yellow pigment)
PY185: C.I. pigment yellow 185 (isoindoline compound, yellow pigment)
PY215: C.I. pigment yellow 215 (pteridine compounds, yellow pigments)
PO71: c.i. pigment orange 71 (diketopyrrolopyrrole compound, orange pigment)
PB15:6: c.i. pigment blue 15:6 (phthalocyanine compound, blue pigment)
(Infrared absorbent)
IR-1: compounds of the structure
[ chemical formula 38]
(pigment derivative)
A-1 to A-6: compounds of the structure
[ chemical formula 39]
[ chemical formula 40]
(dispersant)
B-1: the resin having the following structure (the numbers attached to the main chain are molar ratios, the numbers attached to the side chains are the number of repeating units: weight average molecular weight 24000)
[ chemical formula 41]
B-2: the resin of the following structure (the numbers attached to the main chain are molar ratios, the numbers attached to the side chains are the number of repeating units; weight average molecular weight 10000)
[ chemical formula 42]
B-3: the resin having the following structure (the number indicated in the main chain is a molar ratio, the number indicated in the side chain is the number of repeating units, weight average molecular weight 22000)
[ chemical formula 43]
B-4: the resin having the following structure (the number indicated in the main chain is a molar ratio, the number indicated in the side chain is the number of repeating units, weight average molecular weight 16000)
[ chemical formula 44]
B-5: the resin having the following structure (the number indicated in the main chain is the molar ratio, the number indicated in the side chain is the number of repeating units; weight average molecular weight 20000)
[ chemical formula 45]
B-6: the resin of the following structure (the numbers attached to the main chain are molar ratios, the numbers attached to the side chains are the number of repeating units, weight average molecular weight 7000)
[ chemical formula 46]
B-7: a resin synthesized by the following method
A flask equipped with a reflux condenser, a dropping funnel and a stirrer was purged with nitrogen in an appropriate amount, and 340 parts by mass of Propylene Glycol Monomethyl Ether Acetate (PGMEA) was added thereto, followed by stirring and heating to 80 ℃. Next, 57 parts by mass of acrylic acid, 3, 4-epoxytricyclo [5.2.1.0 were added dropwise over 5 hours 2，6 ]Decane-8-yl acrylate and 3, 4-epoxytricyclo [5.2.1.0 2，6 ]54 parts by mass of a mixture of 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. Next, a solution of 40 parts by mass of a polymerization initiator (2, 2-azobis (2, 4-dimethylvaleronitrile)) dissolved in 197 parts by mass of PGMEA was added dropwise over 6 hours. After the completion of the dropping of the polymerization initiator solution, the mixture was kept at 80℃for 3 hours and then cooled to room temperature to obtain a resin having the following structure. The weight average molecular weight of the obtained resin was 9400, the dispersity was 1.89, and the acid value was 114mgKOH/g.
[ chemical formula 47]
/>
(solvent)
Z-1: propylene Glycol Monomethyl Ether Acetate (PGMEA)
< production of coloring composition >
The raw materials described in the following table were mixed to prepare a coloring composition.
TABLE 31
TABLE 32
TABLE 33
TABLE 34
TABLE 35
/>
TABLE 36
TABLE 37
TABLE 38
TABLE 39
TABLE 40
TABLE 41
TABLE 42
TABLE 43
TABLE 44
TABLE 45
The raw materials described by abbreviations in the above tables are as follows.
(Dispersion liquid)
Dispersions 1 to 79, 101 to 133, 201 to 251, comparative dispersions 1, 2: dispersions 1 to 79 and comparative dispersions 1 and 2
(adhesive)
B-1: the dispersant B-1 described above
B-4: the dispersant B-4 described above
C-1: the resin having the following structure (the numerical value attached to the main chain is a molar ratio, weight average molecular weight 11000)
[ chemical formula 48]
C-2: the resin having the following structure (the numerical value attached to the main chain is a molar ratio, weight average molecular weight 30000)
[ chemical formula 49]
C-3: the resin having the following structure (the numerical value attached to the main chain is mass ratio, weight average molecular weight 14600)
[ chemical formula 50]
C-4: the resin having the following structure (the numerical value attached to the main chain is mass ratio, weight average molecular weight 10600)
[ chemical formula 51]
C-5: a resin synthesized by the following method
A flask equipped with a reflux condenser, a dropping funnel and a stirrer was purged with nitrogen in an appropriate amount, and 371 parts by mass of 1-methoxy-2-propyl ester was added thereto, stirred and heated to 85 ℃. 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] decan-8 and 9-ylacrylate, 81 parts by mass of vinyl toluene (isomer mixture), and 80 parts by mass of 1-methoxy-2-propyl ester was added dropwise over 4 hours. On the other hand, a solution in which 30 parts by mass of 2, 2-azobis (2, 4-dimethylvaleronitrile), a polymerization initiator, was dissolved in 160 parts by mass of 1-methoxy-2-propyl ester was added dropwise over 5 hours. After the completion of the dropwise addition of the initiator solution, the mixture was kept at 85℃for 4 hours and then cooled to room temperature to obtain a resin. The weight average molecular weight of the obtained resin was 10600, the dispersity was 2.01, and the acid value was 43mgKOH/g.
(monomer)
D-1: compounds of the structure
[ chemical formula 52]
D-2: a mixture of compounds of the structure (mixture of compounds on the left (6-functional (meth) acrylate) and compounds on the right (5-functional (meth) acrylate) in a molar ratio of 7:3)
[ chemical formula 53]
D-3: compounds of the structure
[ chemical formula 54]
D-4: trimethylolpropane ethylene oxide modified triacrylate (TOAGOSEI co., ltd. ARONIX M-350)
D-5: EBECRYL80 (DAICEL-ALLNEX LTD. Product, amine-containing 4 functional acrylate)
D-6: ethoxylated dipentaerythritol hexamethyl acrylic ester
(photopolymerization initiator)
E-1 to E-4: compounds of the structure
E-5:2,2', 4-tris (2-chlorophenyl) -5- (3, 4-dimethoxyphenyl) -4, 5-diphenyl-1, 1' -bisimidazole
[ chemical formula 55]
(surfactant)
F-1: KF-6001 (Shin-Etsu Chemical Co., ltd., silicone surfactant, terminal methanol-modified polydimethylsiloxane, hydroxyl value 62 mgKOH/g)
F-2: a compound having the following structure (weight average molecular weight 14000). In the following formula, mol% of the proportion of the repeating unit is represented. (fluorine-based surfactant)
[ chemical formula 56]
F-3: futurent 208G (NEOS-made, fluorine-based surfactant)
F-4: BYK-330 (BYK Co., LTD, silicone surfactant)
F-5: DOWSIL SH8400 FLUID (Dow Toray Co., ltd., silicone surfactant)
(additive)
G-1: compounds of the following structure (ultraviolet absorbers)
[ chemical formula 57]
G-2: a compound having the following structure (a compound having an epoxy group, a weight average molecular weight of 3500)
[ chemical formula 58]
G-3: EHPE3150 (1, 2-epoxy-4- (2-oxetanyl) cyclohexane adduct of 2,2' -bis (hydroxymethyl) -1-butanol, manufactured by Daicel Corporation)
G-4: compounds of the following structure (silane coupling agents)
[ chemical formula 59]
G-5: 3-methacryloxypropyl trimethoxysilane (KBM-503, shin-Etsu Chemical Co., ltd., silane coupling agent)
G-6: para-methoxyphenol (polymerization inhibitor)
G-7: adekastab AO-80 (antioxidant manufactured by ADEKA Corporation)
(solvent)
Z-1: propylene Glycol Monomethyl Ether Acetate (PGMEA)
Z-2: propylene Glycol Monomethyl Ether (PGME)
Z-3: cyclopentanone (CNG)
Z-4: cyclohexanone
Z-5: anisole (anisole)
Z-6: diacetone alcohol
[ evaluation of light resistance ]
The coloring compositions of examples and comparative examples described in the above tables were applied on a glass substrate by spin coating, followed by heat treatment (prebaking) at 100℃for 120 seconds using a heating plate, followed by 1000mJ/cm by i-ray 2 Then, the film was heated at 200℃for 5 minutes to prepare a film having a thickness of 0.6. Mu.m. The film obtained was measured for light transmittance (transmittance) in the wavelength range of 400 to 700nm using MCPD-3000 manufactured by LTD. Next, 100000Lux light was irradiated to the film produced in the above-described manner (total irradiation amount 2 million lux·hr) for 2000 hours by using a light resistance tester (Super Xenon Weather Meter SX, suga Test Instruments co., ltd.). The transmittance of the film after light irradiation was measured, and the light resistance was evaluated by the following criteria.
A: the integrated value of the transmittance of the film after light irradiation at a wavelength of 400 to 700nm is 98% or more of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 to 700 nm.
B: the integrated value of the transmittance of the film after light irradiation at a wavelength of 400 to 700nm is 95% or more and less than 98% of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 to 700 nm.
C: the integrated value of the transmittance of the film after light irradiation at a wavelength of 400 to 700nm is 93% or more and less than 95% of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 to 700 nm.
D: the integrated value of the transmittance of the film after light irradiation at a wavelength of 400 to 700nm is 90% or more and less than 93% of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 to 700 nm.
E: the integrated value of the transmittance of the film after light irradiation at a wavelength of 400 to 700nm is less than 90% of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 to 700 nm.
[ storage stability ]
The viscosities of the coloring compositions of examples and comparative examples described in the above tables immediately after production were measured. The coloring composition having the measured viscosity was stored in a constant temperature bath at 45℃for 72 hours, and then the viscosity was measured. The viscosity was measured by adjusting the temperature of the coloring composition to 23 ℃. The tackifying ratio was calculated from the following calculation formula, and the storage stability was evaluated.
Viscosity increase ratio (%) = ((viscosity of coloring composition after storage in a constant temperature bath of 45 ℃ for 72 hours/viscosity of coloring composition immediately after production) -1) ×100
A: the thickening ratio of the coloring composition is below 5%.
B: the thickening ratio of the coloring composition exceeds 5% and is 7.5% or less.
C: the thickening ratio of the coloring composition exceeds 7.5% and is 10% or less.
D: the tackifying rate of the coloring composition exceeds 10%.
TABLE 46
TABLE 47
TABLE 48
TABLE 49
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 187A 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
As shown in the above table, the coloring composition of examples can form a film excellent in light resistance.
The results of the evaluation in example 1 were the same as those in example 1 except that the surfactant was used. By using the film obtained from the coloring composition of examples, a filter, a solid-state imaging element, and an image display device excellent in light resistance can be obtained.

Claims (15)

1. A coloring composition comprising a colorant and a resin,
the colorant comprises a compound Y having a compound represented by the formula (1) coordinated on a metal atom,
in the 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 ，
R x Represents a substituent group, and is represented by,
at X 2 ～X 9 Wherein 2 adjacent ones are CR x In the case of (2) CR's adjacent to each other x R of (2) x Optionally bonded to each other to form a ring,
wherein the formula (1) satisfies any of the following conditions 1 to 4,
requirement 1X 3 ～X 5 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 2X 2 And X 3 Is CR (CR) x And X is 2 Represented CR x R of (2) x And X is 3 Represented CR x R of (2) x And are bonded to form a heterocyclic ring,
requirement 3X 6 ～X 9 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 4X 2 X is X 3 At least one of them is CH and X 2 ～X 9 At least one of them is CR x 。
2. The coloring composition according to claim 1, wherein,
x of the formula (1) 6 ～X 9 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Bonded to each other to form a ring.
3. The coloring composition according to claim 1 or 2, wherein,
x of the formula (1) 2 ～X 9 At least one of them is CR x ，R x Is a heteroatom-containing group.
4. The coloring composition according to any one of claim 1 to 3, wherein,
x of the formula (1) 2 ～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 、-SO 2 R 107 、-SO 2 NR 108 R 109 、-SO 2 OR 110 、-CONR 111 R 112 or-NR 113 COR 114 ，R 101 R is R 102 Each independently represents a hydrogen atom, an alkyl group or an aryl group, R 101 And R is R 102 Optionally bonded to form a ring, R 103 ～R 114 Each independently represents an alkyl group or an aryl group.
5. The coloring composition according to any one of claims 1 to 4, wherein,
the metal atom is copper atom or zinc atom.
6. The coloring composition according to any one of claims 1 to 4, wherein,
the metal atom is a copper atom.
7. The coloring composition according to any one of claims 1 to 6, wherein,
the maximum absorption wavelength of the compound Y is in the range of 400nm to 700 nm.
8. The coloring composition according to any one of claims 1 to 7, wherein,
the colorant further comprises a green colorant.
9. The coloring composition according to any one of claims 1 to 8, further comprising a polymerizable compound and a photopolymerization initiator.
10. The coloring composition according to any one of claims 1 to 9, for a color filter or for an infrared transmission filter.
11. A film obtained from the coloring composition according to any one of claims 1 to 10.
12. A filter having the film of claim 11.
13. A solid-state imaging element having the film according to claim 11.
14. An image display device having the film of claim 11.
15. A compound having a compound represented by the formula (1) coordinated to a metal atom,
in the 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 ，
R x Represents a substituent group, and is represented by,
at X 2 ～X 9 Wherein 2 adjacent ones are CR x In the case of (2) CR's adjacent to each other x R of (2) x Optionally bonded to each other to form a ring,
wherein the formula (1) satisfies any of the following conditions 1 to 4,
requirement 1X 3 ～X 5 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 2X 2 And X 3 Is CR (CR) x And X is 2 Represented CR x R of (2) x And X is 3 Represented CR x R of (2) x And are bonded to form a heterocyclic ring,
requirement 3X 6 ～X 9 Wherein 2 adjacent ones are CR x And adjacent 2 CR x R of (2) x Are bonded to each other to form a ring,
requirement 4X 2 X is X 3 At least one of them is CH and X 2 ～X 9 At least one of them is CR x 。
CN202280010528.XA 2021-02-03 2022-01-28 Coloring composition, film, optical filter, solid-state imaging element, image display device, and compound Pending CN116848199A (en)

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