Colored composition
The use of a specific coloring composition containing compounds represented by formulas (I) and (IV) in a defined ratio addresses the challenges of low transmittance and solvent resistance in color filters, enhancing their performance and longevity.
Patent Information
- Application Number
- JP2024139278
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-09-15
- Filing Date
- 2024-08-20
- Publication Date
- 2025-03-28
AI Technical Summary
Existing color filters used in display devices and solid-state imaging devices face challenges in achieving high transmittance and solvent resistance, particularly at 505 nm, which affects color performance and longevity.
A coloring composition comprising a compound represented by formula (I) and a compound represented by formula (IV), where the content of compound (IV) ranges from 0.5 to 30 parts by mass based on 100 parts by mass of compound (I), is used to formulate a colored resin composition that improves transmittance and solvent resistance.
The proposed coloring composition enhances the transmittance and solvent resistance of color filters at 505 nm, thereby improving color performance and reducing brightness unevenness over long-term use.
Smart Images

Figure 2025043278000001 
Figure 2025043278000002 
Figure 2025043278000003
Abstract
Description
[Technical field]
[0001] The present invention relates to a colored composition, a colored resin composition containing the colored composition, a color filter formed from the colored resin composition, and a display device and a solid-state imaging device each including the color filter. [Background technology]
[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored resin compositions. Known colorants used in such colored resin compositions include phthalocyanine compounds such as CI Pigment Green 58 (Patent Document 1). [Prior art documents] [Patent documents]
[0003] [Patent Document 1] JP 2009-192661 A Summary of the Invention [Problem to be solved by the invention]
[0004] In the color filter, in order to improve the color performance, it is required to further increase the transmittance of the target wavelength. For example, it is preferable that a green colored filter (green filter) in the color filter has a high transmittance at 505 nm. In addition, the color filter is also required to have excellent solvent resistance. Therefore, an object of the present invention is to provide a new coloring composition that can be used to prepare a color filter having improved transmittance at 505 nm and solvent resistance. [Means for solving the problem]
[0005] The gist of the present invention is as follows. [1] A coloring composition comprising a compound represented by formula (I) and a compound represented by formula (IV), A coloring composition, comprising a compound represented by formula (IV) in an amount of 0.5 parts by mass or more and 30 parts by mass or less based on 100 parts by mass of the compound represented by formula (I). [ka] [In formula (I), R 1A ~R 16A each independently represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. 1A ~R 16A at least one of represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and when there are a plurality of groups represented by formula (ia), they may be the same or different, when there are a plurality of groups represented by formula (ib), they may be the same or different, and when there are a plurality of groups represented by formula (ic), they may be the same or different. [ka] [In formula (ia), R a1 ~R a5 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. a1 ~R a5 At least one of represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ib), R b1 ~R b7 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. b1 ~R b7 At least one of represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ic), R c1 ~R c7 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. c1 ~R c7 At least one of represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (IV), R 1B ~R 16B each independently represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. 1B ~R 16Bat least one of represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic); when there is a plurality of groups represented by formula (ia), they may be the same or different; when there is a plurality of groups represented by formula (ib), they may be the same or different; and when there is a plurality of groups represented by formula (ic), they may be the same or different. X is a halogen atom, a hydroxyl group, or OR M R M represents a hydrocarbon group having 1 to 6 carbon atoms.] [2] Contains colorants and resins; The colored resin composition, wherein the colorant comprises the colored composition according to [1]. [3] The colored resin composition according to [2], further comprising a polymerizable compound and a polymerization initiator. [4] A color filter formed from the colored resin composition according to [2] or [3]. [5] A display device comprising the color filter according to [4]. [6] A solid-state imaging device comprising the color filter according to [4]. Effect of the Invention
[0006] According to the coloring composition of the present invention, a color filter having improved transmittance at 505 nm and solvent resistance can be provided. Furthermore, according to the coloring composition of the present invention, it is preferable that unevenness in brightness of the obtained color filter after long-term use can be suppressed. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0007] [Coloring composition] The coloring composition of the present invention contains a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)) and a compound represented by formula (IV) (hereinafter, sometimes referred to as compound (IV)). When the coloring composition contains compound (I), the solvent resistance of the resulting color filter can be improved. In addition, when the coloring composition of the present invention contains compound (I), a colored filter in which the brightness difference between the periphery and the center after long-term use is suppressed can be formed, that is, it is also preferable in that a color filter with little brightness unevenness can be obtained. On the other hand, when the coloring composition of the present invention contains compound (IV), the transmittance at 505 nm of the resulting color filter can be increased.
[0008] The content of compound (IV) is 0.5 to 30 parts by mass, preferably 0.7 to 25 parts by mass, and more preferably 1.0 to 20 parts by mass, relative to 100 parts by mass of compound (I). By adjusting the content of compound (IV) relative to compound (I) within the above range, a color filter having an excellent balance between transmittance at 505 nm and solvent resistance can be produced. In particular, from the viewpoint of further increasing the transmittance at 505 nm of the obtained color filter, the content of compound (IV) is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and particularly preferably 15 parts by mass or more, relative to 100 parts by mass of compound (I). In addition, from the viewpoint of further increasing the solvent resistance of the obtained color filter, the content of compound (IV) is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, even more preferably 10 parts by mass or less, and particularly preferably 7 parts by mass or less, relative to 100 parts by mass of compound (I).
[0009] <Compound (I)> The present invention will be described more specifically below with reference to partial structures of compound (I).
[0010] [ka] [In formula (I), R 1A ~R 16Aeach independently represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. 1A ~R 16A at least one of represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and when there are a plurality of groups represented by formula (ia), they may be the same or different, when there are a plurality of groups represented by formula (ib), they may be the same or different, and when there are a plurality of groups represented by formula (ic), they may be the same or different. [ka] [In formula (ia), R a1 ~R a5 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. a1 ~R a5 At least one of represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ib), R b1 ~R b7 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. b1 ~R b7 At least one of represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] [ka] [In formula (ic), R c1 ~R c7 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. c1 ~R c7 At least one of represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.]
[0011] R 1A ~R 16A Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom, a chlorine atom, or a bromine atom is preferred, and a fluorine atom is more preferred.
[0012] R 1A ~R 16A The hydrocarbon group having 1 to 6 carbon atoms represented by the formula (I) may be either an aliphatic hydrocarbon group or a phenyl group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).
[0013] Examples of saturated chain hydrocarbon groups (hereinafter sometimes referred to as alkyl groups) include linear alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group; and branched alkyl groups such as an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 1,3-dimethylbutyl group, a 2-methyl-2-pentyl group, and a 2-ethylbutyl group. The alkyl group preferably has 1 to 4 carbon atoms, and more preferably has 1 to 3 carbon atoms.
[0014] Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl) groups; and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl) groups. The unsaturated chain hydrocarbon group preferably has 2 to 6 carbon atoms, and more preferably 2 to 4 carbon atoms.
[0015] Examples of the saturated alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
[0016] Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as cyclohexenyl groups (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, and cyclohex-3-en-1-yl).
[0017] The alicyclic hydrocarbon group preferably has 3 to 6 carbon atoms.
[0018] R 1A ~R 16A The hydrocarbon group having 1 to 6 carbon atoms represented by the formula (I) may have a substituent. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a hydroxy group; a carboxy group; an unsubstituted amino group; a substituted amino group such as an N-methylamino group, an N,N-dimethylamino group, an N-ethylamino group, an N,N-diethylamino group, an N-propylamino group, an N,N-dipropylamino group, an N-isopropylamino group, an N,N-diisopropylamino group, an N-phenylamino group, an N,N-diphenylamino group, or an N,N-ethylmethylamino group; a cyano group, and the like.
[0019] R 1A ~R 16Ahas 2 to 6 carbon atoms and has -CH2-, the -CH2- may be replaced with -O- or -CO-, provided that adjacent -CH2- are not simultaneously replaced with -O- and the terminal -CH2- is not replaced with -O- in the hydrocarbon group having 1 to 6 carbon atoms.
[0020] In this specification, when -CH2- in a hydrocarbon group is replaced by -O- or -CO-, the number of carbon atoms in the group replaced by -O- or -CO- means the number of carbon atoms in the hydrocarbon group before being replaced by -O- or -CO-. For example, a *-O-CH2-CH2-CH3 group is a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3) in which -CH2- is replaced by -O-. In addition, if there are multiple -CH2- that can be replaced in the hydrocarbon group, the number of replacements is not necessarily limited to 1. For example, two -CH2- in a hydrocarbon group having 4 carbon atoms (*-CH2-CH2-CH2-CH3) can be replaced with -O- to become *-O-CH2-O-CH3, and one -CH2- can be replaced with -O- and one -CH2- can be replaced with -CO- to become *-O-CO-CH2-CH3 or *-CO-O-CH2-CH3. That is, groups in which two or more -CH2- are replaced with -O-, such as *-O-CH2-O-CH3, *-O-CO-CH2-CH3, and *-CO-O-CH2-CH3, are also included in "groups in which -CH2- in a hydrocarbon group having 1 to 6 carbon atoms, which may have a substituent, is replaced with -O- or -CO-".
[0021] R 1A ~R 16A As the hydrocarbon group having 1 to 6 carbon atoms which may have a substituent and is represented by the following formula, an alkyl group is preferable.
[0022] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a chlorine atom, a bromine atom, or an iodine atom is preferred, and a chlorine atom or a bromine atom is more preferred.
[0023] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may be any of an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a combination thereof, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or cyclic (alicyclic hydrocarbon group).
[0024] Examples of saturated chain hydrocarbon groups (alkyl groups) include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl, 2-methyl-2-pentyl, and 2-ethylhexyl groups. The alkyl group preferably has 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, further preferably 1 to 4 carbon atoms, and particularly preferably 1 to 3 carbon atoms.
[0025] Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (e.g., 1-propenyl, 2-propenyl), and butenyl (e.g., 1-butenyl, 3-butenyl) groups; and alkynyl groups such as ethynyl, propynyl (e.g., 1-propynyl, 2-propynyl), and butynyl (e.g., 1-butynyl, 3-butynyl) groups. The unsaturated chain hydrocarbon group preferably has 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, and further preferably 2 to 4 carbon atoms.
[0026] Examples of the saturated alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a 2-methylcyclohexyl group.
[0027] Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as a cyclohexenyl group (for example, a cyclohex-1-en-1-yl group, a cyclohex-2-en-1-yl group, a cyclohex-3-en-1-yl group), a cycloheptenyl group, and a cyclooctenyl group.
[0028] Examples of the alicyclic hydrocarbon group include polycyclic saturated alicyclic hydrocarbon groups such as a norbornyl group, an adamantyl group, and a bicyclo[2.2.2]octyl group; and polycyclic unsaturated alicyclic hydrocarbon groups such as a norbornenyl group.
[0029] The alicyclic hydrocarbon group preferably has 3-10 carbon atoms, and more preferably 4-8 carbon atoms.
[0030] Examples of the aromatic hydrocarbon group include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,4-dimethylphenyl group, a 2,6-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,4-diisopropylphenyl group, a 2,6-diisopropylphenyl group, a 4-vinylphenyl group, an o-tert-butylphenyl group, an m-tert-butylphenyl group, a p-tert-butylphenyl group, a 2,6-di(tert-butyl)phenyl group, a 3,5-di(tert-butyl)phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a group in which one hydrogen atom has been removed from tetralin.
[0031] The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and further preferably 6 to 10 carbon atoms.
[0032] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7The hydrocarbon group represented by the formula (I) may be a group formed by combining the above-listed hydrocarbon groups, so long as the total number of carbon atoms is 20 or less. Examples of the group formed by combining hydrocarbon groups include an aralkyl group and an alkyl group bonded to an alicyclic hydrocarbon group.
[0033] Examples of the aralkyl group include aralkyl groups such as benzyl, (2-methylphenyl)methyl, (3-methylphenyl)methyl, (4-methylphenyl)methyl, (2-ethylphenyl)methyl, (3-ethylphenyl)methyl, (4-ethylphenyl)methyl, (2-(tert-butyl)phenyl)methyl, (3-(tert-butyl)phenyl)methyl, (4-(tert-butyl)phenyl)methyl, (3,5-dimethylphenyl)methyl, 1-phenylethyl, 1-methyl-1-phenylethyl, 1,1-diphenylethyl, (1-naphthyl)methyl, (2-naphthyl)methyl, and 9-fluorenylmethyl. The number of carbon atoms in the aralkyl group is preferably 7 to 18, more preferably 7 to 12.
[0034] Examples of the alkyl group having an alicyclic hydrocarbon group bonded thereto include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, an adamantylmethyl group, etc. The number of carbon atoms in the alkyl group having an alicyclic hydrocarbon group bonded thereto is preferably 4 to 20, more preferably 4 to 15, and further preferably 4 to 10.
[0035] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The substituent that the hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have is, for example, R 1A ~R 16A These are the same as the examples of the substituent that the hydrocarbon group having 1 to 6 carbon atoms represented by the following formula may have.
[0036] R a1 ~Ra5 , R b1 ~R b7 and R c1 ~R c7 When the hydrocarbon group represented by the formula (I) has 2 to 20 carbon atoms and has -CH2-, the -CH2- may be replaced with -O- or -CO-. However, in the hydrocarbon group having 1 to 20 carbon atoms, adjacent -CH2- are not simultaneously replaced with -O-, and the terminal -CH2- is not replaced with -O- or -CO-. In particular, the group in which -CH2- is replaced with -O- or -CO- is preferably an alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, or a tert-butoxy group, more preferably an alkoxy group having 1 to 10 carbon atoms, and even more preferably an alkoxy group having 1 to 4 carbon atoms.
[0037] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7 The hydrocarbon group having 1 to 20 carbon atoms, which may have a substituent represented by the formula (I), is preferably an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.
[0038] R a1 ~R a5 , R b1 ~R b7 and R c1 ~R c7are each independently preferably a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 10 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms, more preferably a hydrogen atom, a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and even more preferably a hydrogen atom, a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.
[0039] In the group represented by formula (ia), R a1 ~R a5 Among these, the total number of halogen atoms and carboxy groups (particularly chlorine atoms, bromine atoms, and carboxy groups) is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1. In the group represented by formula (ib), R b1 ~R b7 Among these, the total number of halogen atoms and carboxy groups (particularly chlorine atoms, bromine atoms, and carboxy groups) is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1. In the group represented by formula (ic), R c1 ~R c7 Among these, the total number of halogen atoms and carboxy groups (particularly chlorine atoms, bromine atoms, and carboxy groups) is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1.
[0040] In the group represented by formula (ia), R a1 ~R a5 at least one of R is a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (-CH- constituting the hydrocarbon group may be replaced by -O- or -CO-), a1 ~R a5At least one of R is preferably a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 10 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms. a1 ~R a5 It is more preferable that at least one of them is a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R a1 ~R a5 Among these, it is preferred that 1 to 3 of them are each independently a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (-CH- constituting the hydrocarbon group may be replaced by -O- or -CO-), and the remainder are hydrogen atoms; a1 ~R a5 Among these, it is more preferable that 1 to 3 are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.
[0041] In the group represented by formula (ib), R b1 ~R b7 at least one of R is a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (-CH- constituting the hydrocarbon group may be replaced by -O- or -CO-), b1 ~R b7 At least one of R is preferably a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 10 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms. b1 ~R b7 It is more preferable that at least one of them is a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R b1 ~Rb7 Among these, it is preferred that 1 to 3 of them are each independently a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (-CH- constituting the hydrocarbon group may be replaced by -O- or -CO-), and the remainder are hydrogen atoms; b1 ~R b7 Among these, it is more preferable that 1 to 3 are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.
[0042] In the group represented by formula (ic), R c1 ~R c7 at least one of R is a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (-CH- constituting the hydrocarbon group may be replaced by -O- or -CO-), c1 ~R c7 At least one of R is preferably a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 10 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms. c1 ~R c7 It is more preferable that at least one of them is a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R c1 ~R c7 Among these, it is preferred that 1 to 3 of them are each independently a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (-CH- constituting the hydrocarbon group may be replaced by -O- or -CO-), and the remainder are hydrogen atoms; c1 ~R c7Among these, it is more preferable that 1 to 3 are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.
[0043] Specific examples of the group represented by formula (ia) include groups represented by the following formulae (i-a1) to (i-a35).
[0044] [ka]
[0045] [ka]
[0046] [ka]
[0047] Specific examples of the group represented by formula (ib) include groups represented by the following formulae (i-b1) to (i-b8), and among these, the group represented by formula (i-b1) is preferred.
[0048] [ka]
[0049] Specific examples of the group represented by formula (ic) include groups represented by the following formulae (i-c1) to (i-c10), and among these, the group represented by formula (i-c1) is preferred.
[0050] [ka]
[0051] R 1A ~R 16Aare each independently preferably a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and more preferably a hydrogen atom, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic).
[0052] In compound (I), R 1A ~R 16A At least one of R represents a group represented by formula (ia), formula (ib), or formula (ic) (hereinafter, these may be collectively referred to as "aryloxy group (i)"). 1A ~R 16A In the formula (I), the total number of aryloxy groups (i) is, for example, 2 to 16, preferably 4 to 16, more preferably 4 to 8, and even more preferably 4. When compound (I) has a plurality of groups represented by formula (ia), the groups represented by the plurality of formulas (ia) may be the same or different, but are preferably the same, when compound (I) has a plurality of groups represented by formula (ib), the groups represented by the plurality of formulas (ib) may be the same or different, but are preferably the same, and when compound (I) has a plurality of groups represented by formula (ic), the groups represented by the plurality of formulas (ic) may be the same or different, but are preferably the same.
[0053] Furthermore, when compound (I) has a plurality of aryloxy groups (i), they are more preferably the same.
[0054] The aryloxy group (i) is preferably a group represented by formula (ia) or formula (ib), more preferably a group represented by formula (ia).
[0055] R 1A ~R 16A In the above, the position of the aryloxy group (i) is not particularly limited, but Aspect (1): R 1A ~R 4A At least one of R is an aryloxy group (i); 5A ~R8A At least one of R is an aryloxy group (i); 9A ~R 12A At least one of R is an aryloxy group (i), and R 13A ~R 16A At least one of the groups is preferably an aryloxy group (i), Aspect (2): R 2A and R 3A At least one of R is an aryloxy group (i); 6A and R 7A At least one of R is an aryloxy group (i); 10A and R 11A At least one of R is an aryloxy group (i), and R 14A and R 15A At least one of R is an aryloxy group (i); 1A , R 4A , R 5A , R 8A , R 9A , R 12A , R 13A , and R 16A is a hydrogen atom, or aspect (3): R 1A and R 4A At least one of R is an aryloxy group (i); 5A and R 8A At least one of R is an aryloxy group (i); 9A and R 12A At least one of R is an aryloxy group (i), and R 13A and R 16A At least one of R is an aryloxy group (i); 2A , R 3A , R 6A , R 7A , R 10A , R 11A , R 14A , and R 15A is more preferably a hydrogen atom, Aspect (4): R 2A and R 3A one of the groups is an aryloxy group (i), and R 6A and R7A one of the groups is an aryloxy group (i), and R 10A and R 11A one of the groups (i) is an aryloxy group, and R 14A and R 15A one of the groups is an aryloxy group (i), and R 1A , R 4A , R 5A , R 8A , R 9A , R 12A , R 13A , and R 16A is a hydrogen atom, or embodiment (5): R 1A and R 4A one of the groups is an aryloxy group (i), and R 5A and R 8A one of the groups is an aryloxy group (i), and R 9A and R 12A one of the groups (i) is an aryloxy group, and R 13A and R 16A one of the groups is an aryloxy group (i), and R 2A , R 3A , R 6A , R 7A , R 10A , R 11A , R 14A , and R 15A is more preferably a hydrogen atom, Aspect (6): R 2A and R 3A one of R is an aryloxy group (i) and the other is a hydrogen atom; 6A and R 7A one of R is an aryloxy group (i) and the other is a hydrogen atom; 10A and R 11A one of R is an aryloxy group (i) and the other is a hydrogen atom, and R 14A and R 15A one of R is an aryloxy group (i) and the other is a hydrogen atom; 1A , R 4A , R 5A , R 8A , R 9A, R 12A , R 13A , and R 16A is a hydrogen atom, or embodiment (7): R 1A , R 5A , R 9A , and R 13A is an aryloxy group (i), and R 2A ~R 4A , R 6A ~R 8A , R 10A ~R 12A , and R 14A ~R 16A It is particularly preferable that is a hydrogen atom. In each of the above embodiments (1) to (7), the multiple aryloxy groups (i) in compound (I) may be the same or different, but are preferably the same.
[0056] From the viewpoint of further reducing unevenness in brightness of the resulting color filter after long-term use, embodiment (2) is preferred, embodiment (4) is more preferred, and embodiment (6) is even more preferred.
[0057] Compound (I) is preferably a compound represented by formula (IA) (hereinafter, compound (IA)) and / or a compound represented by formula (IB) (hereinafter, compound (IB)). From the viewpoint of suppressing uneven brightness after long-term use of the resulting color filter while achieving both transmittance at 505 nm and solvent resistance, compound (IA) is preferred.
[0058] [ka] [In formula (IA), R 102A and R 103A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 106A and R 107A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R110A and R 111A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 114A and R 115A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 101A , R 104A , R 105A , R 108A , R 109A , R 112A , R 113A , and R 116A is a hydrogen atom. In formula (IB), R 101B , R 105B , R 109B , and R 113B are each independently a group represented by formula (iA-a), formula (iA-b), or formula (iA-c), and R 102B ~R 104B , R 106B ~R 108B , R 110B ~R 112B , and R 114B ~R 116B is a hydrogen atom.] [ka] [In formula (iA-a), R a1A ~R a5A each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. a1A ~R a5A At least one of is a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. * represents a bond. In formula (iA-b), R b1A ~R b7A each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. b1A ~R b7A At least one of is a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. * represents a bond. In formula (iA-c), R c1A ~R c7A each independently represents a hydrogen atom, a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. c1A ~R c7A At least one of is a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. * represents a bond.]
[0059] The four groups represented by formula (iA-a), formula (iA-b), or formula (iA-c) in compound (IA) may be the same or different, but are preferably the same. The four groups represented by formula (iA-a), formula (iA-b), or formula (iA-c) in compound (IB) may be the same or different, but are preferably the same.
[0060] In compound (IA), R 102A and R 103A , R 106A and R 107A , R 110A and R 111A, and R 114A and R 115A is preferably one of which is a group represented by formula (iA-a) and the other is a hydrogen atom, or one of which is a group represented by formula (iA-b) and the other is a hydrogen atom, and it is more preferably one of which is a group represented by formula (iA-a) and the other is a hydrogen atom. In compound (IB), R 101B , R 105B , R 109B , and R 113B is preferably a group represented by formula (iA-a) or formula (iA-b), and more preferably a group represented by formula (iA-a).
[0061] R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A Examples of the alkoxy group having 1 to 4 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a tert-butoxy group. R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A As the alkyl group having 1 to 8 carbon atoms represented by the formula: a1 ~R a5 , R b1 ~R b7 , and R c1 ~R c7 Among the groups explained as the alkyl group represented by the following formula, groups having 1 to 8 carbon atoms can be mentioned. R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A Examples of the cycloalkyl group having 3 to 10 carbon atoms represented by the formula: a1 ~R a5 , R b1 ~R b7 , and R c1 ~R c7Among the groups explained as the cycloalkyl group represented by the following formula, groups having 3 to 10 carbon atoms can be mentioned. R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A As the aromatic hydrocarbon group having 6 to 12 carbon atoms represented by the formula: a1 ~R a5 , R b1 ~R b7 , and R c1 ~R c7 Among the groups explained as the aromatic hydrocarbon group represented by the following formula, groups having 6 to 12 carbon atoms are exemplified. R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A As the aralkyl group having 7 to 12 carbon atoms represented by the formula: a1 ~R a5 , R b1 ~R b7 , and R c1 ~R c7 Among the groups explained as the aralkyl group represented by the following formula, groups having 7 to 12 carbon atoms can be mentioned.
[0062] R a1A ~R a5A , R b1A ~R b7A , and R c1A ~R c7A are preferably each independently a hydrogen atom, a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.
[0063] In the group represented by formula (iA-a), R a1A ~R a5A Among these, the total number of chlorine atoms, bromine atoms, and carboxy groups is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1. In the group represented by formula (iA-b), R b1A ~R b7A Among these, the total number of chlorine atoms, bromine atoms, and carboxy groups is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1. In the group represented by formula (iA-c), R c1A ~R c7A Among these, the total number of chlorine atoms, bromine atoms, and carboxy groups is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1.
[0064] In the group represented by formula (iA-a), R a1A ~R a5A At least one of them is preferably a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R a1A ~R a5A Among these, it is preferred that 1 to 3 of them are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom; a1A ~R a5A Among these, it is more preferable that 1 to 3 are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.
[0065] In the group represented by formula (iA-b), R b1A ~R b7A At least one of them is preferably a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R b1A ~R b7A Among these, it is preferred that 1 to 3 of them are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom; b1A ~R b7A Among these, it is more preferable that 1 to 3 are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.
[0066] In the group represented by formula (iA-c), R c1A ~R c7A At least one of them is preferably a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms. In particular, R c1A ~R c7A Among these, it is preferred that 1 to 3 of them are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom; c1A ~R c7A Among these, it is more preferable that 1 to 3 are each independently a chlorine atom, a bromine atom, a carboxy group, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 4 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and the remainder are a hydrogen atom.
[0067] Specific examples of the group represented by formula (iA-a) include the groups represented by the above formulas (i-a1) to (i-a35), etc.; specific examples of the group represented by formula (iA-b) include the groups represented by the above formulas (i-b1) to (i-b8), etc.; and specific examples of the group represented by formula (iA-c) include the groups represented by the above formulas (i-c1) to (i-c10), etc.
[0068] Specific examples of compound (I) include R 1A ~R 16A Compounds (Ia-1) to (Ia-272) in which R is a group shown in No. a1 to a272, 1A ~R 16A In the above, there can be mentioned compounds (Ib-1) to (Ib-34) each of which is a group shown in No. b1 to b34.
[0069] [Table 1]
[0070] [Table 2]
[0071] [Table 3]
[0072] [Table 4]
[0073] [Table 5]
[0074] [Table 6]
[0075] [Table 7]
[0076] [Table 8]
[0077] In Tables 1 to 8, i-a1 to i-a28, i-a32 to i-a35, i-b1, and i-c1 represent groups represented by the above formulae (i-a1) to (i-a28), (i-a32) to (i-a35), (i-b1), and (i-c1), and H represents a hydrogen atom.
[0078] <Compound (IV)> Next, the present invention will be described more specifically with reference to the partial structure of compound (IV).
[0079] [ka] [In formula (IV), R 1B ~R 16B each independently represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and -CH2- contained in the hydrocarbon group may be replaced by -O- or -CO-. 1B ~R 16B at least one of represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic); when there is a plurality of groups represented by formula (ia), they may be the same or different; when there is a plurality of groups represented by formula (ib), they may be the same or different; and when there is a plurality of groups represented by formula (ic), they may be the same or different. X is a halogen atom, a hydroxyl group, or OR M R M represents a hydrocarbon group having 1 to 6 carbon atoms.]
[0080] R 1B ~R 16B The halogen atom represented by the formula R 1A ~R 16A The preferred embodiments are also the same as those of the halogen atom represented by the following formula:
[0081] R 1B ~R 16B The hydrocarbon group having 1 to 6 carbon atoms, which may have a substituent, is represented by R 1A ~R 16A The examples of the hydrocarbon group having 1 to 6 carbon atoms which may have a substituent and which is represented by the following formula (I) include the same groups as those explained above as the hydrocarbon group having 1 to 6 carbon atoms which may have a substituent and which is represented by the following formula (I), and the preferred embodiments thereof are also the same.
[0082] The group represented by formula (ia) is the same as the group explained as the group represented by formula (ia) in compound (I), and preferred embodiments thereof are also the same. The group represented by formula (ib) is the same as the group explained as the group represented by formula (ib) in compound (I), and preferred embodiments thereof are also the same. The group represented by formula (ic) is the same as the group explained as the group represented by formula (ic) in compound (I), and preferred embodiments thereof are also the same.
[0083] R 1B ~R 16B are each independently preferably a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and more preferably a hydrogen atom, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic).
[0084] In compound (IV), R 1B ~R 16B At least one of R represents a group represented by formula (ia), formula (ib), or formula (ic) (i.e., an aryloxy group (i)). 1B ~R 16BIn the formula (I), the total number of aryloxy groups (i) is, for example, 2 to 16, preferably 4 to 16, more preferably 4 to 8, and even more preferably 4. When compound (IV) has a plurality of groups represented by formula (ia), the groups represented by the plurality of formulas (ia) may be the same or different, but are preferably the same, when compound (IV) has a plurality of groups represented by formula (ib), the groups represented by the plurality of formulas (ib) may be the same or different, but are preferably the same, and when compound (IV) has a plurality of groups represented by formula (ic), the groups represented by the plurality of formulas (ic) may be the same or different, but are preferably the same.
[0085] Furthermore, when compound (IV) has a plurality of aryloxy groups (i), they are more preferably the same.
[0086] The aryloxy group (i) is preferably a group represented by formula (ia) or formula (ib), more preferably a group represented by formula (ia).
[0087] R 1B ~R 16B The position of the aryloxy group (i) is not particularly limited, but Aspect (1): R 1B ~R 4B At least one of R is an aryloxy group (i); 5B ~R 8B At least one of R is an aryloxy group (i); 9B ~R 12B At least one of R is an aryloxy group (i), and R 13B ~R 16B At least one of the groups is preferably an aryloxy group (i), Aspect (2): R 2B and R 3B At least one of R is an aryloxy group (i); 6B and R 7B At least one of R is an aryloxy group (i); 10B and R 11BAt least one of R is an aryloxy group (i), and R 14B and R 15B At least one of R is an aryloxy group (i); 1B , R 4B , R 5B , R 8B , R 9B , R 12B , R 13B , and R 16B is a hydrogen atom, or aspect (3): R 1B and R 4B At least one of R is an aryloxy group (i); 5B and R 8B At least one of R is an aryloxy group (i); 9B and R 12B At least one of R is an aryloxy group (i), and R 13B and R 16B At least one of R is an aryloxy group (i); 2B , R 3B , R 6B , R 7B , R 10B , R 11B , R 14B , and R 15B is more preferably a hydrogen atom, Aspect (4): R 2B and R 3B one of the groups is an aryloxy group (i), and R 6B and R 7B one of the groups is an aryloxy group (i), and R 10B and R 11B one of the groups (i) is an aryloxy group, and R 14B and R 15B one of the groups is an aryloxy group (i), and R 1B , R 4B , R 5B , R 8B , R 9B , R 12B , R 13B , and R 16B is a hydrogen atom, or embodiment (5): R 1B and R 4Bone of the groups is an aryloxy group (i), and R 5B and R 8B one of the groups is an aryloxy group (i), and R 9B and R 12B one of the groups (i) is an aryloxy group, and R 13B and R 16B one of the groups is an aryloxy group (i), and R 2B , R 3B , R 6B , R 7B , R 10B , R 11B , R 14B , and R 15B is more preferably a hydrogen atom, Aspect (6): R 2B and R 3B one of R is an aryloxy group (i) and the other is a hydrogen atom; 6B and R 7B one of R is an aryloxy group (i) and the other is a hydrogen atom; 10B and R 11B one of R is an aryloxy group (i) and the other is a hydrogen atom, and R 14B and R 15B one of R is an aryloxy group (i) and the other is a hydrogen atom; 1B , R 4B , R 5B , R 8B , R 9B , R 12B , R 13B , and R 16B is a hydrogen atom, or embodiment (7); R 1B , R 5B , R 9B , and R 13B is an aryloxy group (i), and R 2B ~R 4B , R 6B ~R 8B , R 10B ~R 12B , and R 14B ~R 16B It is particularly preferable that is a hydrogen atom. In each of the above embodiments (1) to (7), the multiple aryloxy groups (i) in compound (IV) may be the same or different, but are preferably the same.
[0088] Among these, embodiment (2) is preferred, embodiment (4) is more preferred, and embodiment (6) is even more preferred.
[0089] Examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among these, a chlorine atom is preferred.
[0090] R M As the hydrocarbon group having 1 to 6 carbon atoms represented by the formula: 1A ~R 16A and R 1B ~R 16B The examples of the hydrocarbon group having 1 to 6 carbon atoms and represented by the following formula are the same as those described above, and the preferred embodiments are also the same. OR M Specific examples of the group include alkoxy groups having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a tert-butoxy group, and a phenoxy group. Among these, an alkoxy group having 1 to 6 carbon atoms is preferred, and an alkoxy group having 1 to 4 carbon atoms is more preferred.
[0091] X is preferably a halogen atom, a hydroxy group, or an alkoxy group having 1 to 4 carbon atoms, more preferably a chlorine atom or a hydroxy group, and particularly preferably a chlorine atom.
[0092] Compound (IV) is a compound represented by formula (IVA) (hereinafter, compound (IVA)). or a compound represented by formula (IVB) (hereinafter, compound (IVB)), is preferred, with compound (IVA) being more preferred.
[0093] [ka] [In formula (IVA), R 202Aand R 203A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 206A and R 207A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 210A and R 211A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 214A and R 215A one of the formulas is a group represented by formula (iA-a), (iA-b), or (iA-c), and the other is a hydrogen atom; R 201A , R 204A , R 205A , R 208A , R 209A , R 212A , R 213A , and R 216A is a hydrogen atom. X has the same meaning as above. In formula (IVB), R 201B , R 205B , R 209B , and R 213B are each independently a group represented by formula (iA-a), formula (iA-b), or formula (iA-c), and R 202B ~R 204B , R 206B ~R 208B , R 210B ~R 212B , and R 214B ~R 216B is a hydrogen atom. X has the same meaning as above.]
[0094] The group represented by formula (iA-a) is the same as the group explained as the group represented by formula (iA-a) in compounds (IA) and (IB), and preferred embodiments thereof are also the same. The group represented by formula (iA-b) is the same as the group represented by formula (iA-b) explained in compounds (IA) and (IB), and preferred embodiments thereof are also the same. The group represented by formula (iA-c) is the same as the group explained as the group represented by formula (iA-c) in compounds (IA) and (IB), and preferred embodiments thereof are also the same.
[0095] X in compounds (IVA) and (IVB) has the same meaning as above, and the preferred embodiments thereof are also the same.
[0096] The four groups represented by formula (iA-a), formula (iA-b), or formula (iA-c) in compound (IVA) may be the same or different, but are preferably the same. The four groups represented by formula (iA-a), formula (iA-b), or formula (iA-c) in compound (IVB) may be the same or different, but are preferably the same.
[0097] In compound (IVA), R 202A and R 203A , R 206A and R 207A , R 210A and R 211A , and R 214A and R 215A are each independently preferably one of which is a group represented by formula (iA-a) and the other is a hydrogen atom, or one of which is a group represented by formula (iA-b) and the other is a hydrogen atom, and more preferably one of which is a group represented by formula (iA-a) and the other is a hydrogen atom. In compound (IVB), R 201B , R 205B , R 209B , and R 213B are each independently preferably a group represented by formula (iA-a) or formula (iA-b), and more preferably a group represented by formula (iA-a).
[0098] Specific examples of compound (IV) include R 1B ~R16B Compounds (IVa-1) to (IVa-272) in which R is a group shown in No. a1 to a272 in Tables 1 to 7 above and X is a chlorine atom, and 1B ~R 16B is a group shown in No. b1 to b34 in Table 8 above, and X is a chlorine atom, and the like.
[0099] In the compound (I) and the compound (IV) contained in the coloring composition of the present invention, the type of the aryloxy group (i) in the compound (I) and the type of the aryloxy group (i) in the compound (IV) may be the same or different, but it is preferable that they are the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, the number of aryloxy groups (i) in compound (I) and the number of aryloxy groups (i) in compound (IV) may be the same or different, but are preferably the same.
[0100] In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 1A and R 1B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 2A and R 2B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 3A and R 3B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 4A and R 4B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 5A and R 5B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 6A and R 6B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 7A and R 7B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 8A and R 8B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 9A and R 9B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 10A and R 10B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 11A and R 11B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 12A and R 12B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 13A and R 13B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 14A and R 14B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R15A and R 15B may be the same or different, but is preferably the same. In the compound (I) and compound (IV) contained in the coloring composition of the present invention, R 16A and R 16B may be the same or different, but is preferably the same.
[0101] <Method for producing compound (I) and compound (IV)> The method for producing compound (I) and compound (IV) is not particularly limited, but it is preferable to react compounds represented by formulas (II-1) to (II-4) (hereinafter collectively referred to as phthalonitrile compound (II)) in the presence of a base and a compound represented by formula (III) (hereinafter referred to as aluminum compound (III)). [ka] [In formula (III), X has the same meaning as defined above.] [ka] [In formulas (II-1) to (II-4), R 1A ~R 16A has the same meaning as above.]
[0102] By adjusting the amount of the aluminum compound (III) used relative to the phthalonitrile compound (II), it is possible to preferentially synthesize the compound (I) or the compound (IV). For example, the amount of the aluminum compound (III) used relative to the total amount of 1 mole of the phthalonitrile compound (II) is adjusted to preferably 0.25 to 0.40 moles, more preferably 0.27 to 0.34 moles, so that the compound (I) can be preferentially synthesized. In addition, the amount of the aluminum compound (III) used per mole of the total amount of the phthalonitrile compounds (II) is adjusted to preferably 0.41 to 0.75 moles, more preferably 0.45 to 0.70 moles, so that the compound (IV) can be preferentially synthesized.
[0103] As the base, an inorganic base and / or an organic base can be used. Examples of inorganic bases include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal phosphates such as trisodium phosphate and tripotassium phosphate; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; and the like. Examples of the organic base include trialkylamines such as triethylamine and N,N-diisopropylethylamine; nitrogen-containing heterocyclic compounds such as pyridine, picoline, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN); and the like. Among these, organic bases are preferred, nitrogen-containing heterocyclic compounds are more preferred, and 1,8-diazabicyclo[5.4.0]-7-undecene is even more preferred.
[0104] The amount of the base used is preferably 1.0 to 5.0 mol, more preferably 1.3 to 2.0 mol, per mol of the total amount of the phthalonitrile compound (II).
[0105] The reaction of the phthalonitrile compound (II) may be carried out in the presence of a solvent or in the absence of a solvent, but is preferably carried out in the presence of a solvent from the viewpoint of improving the reaction efficiency.
[0106] The solvent is preferably an organic solvent, for example: Ester solvents such as methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and gamma-butyrolactone; Ether solvents such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole and methylanisole; Alcohol solvents such as methanol, ethanol, propanol, butanol, heptanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and glycerin;
[0107] Among these, from the viewpoint of further improving the reaction efficiency, the solvent is preferably an alcohol solvent, more preferably a polyhydric alcohol solvent such as ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, or glycerin, and particularly preferably a polyhydric alcohol solvent having a boiling point of 160° C. or higher (preferably 200° C. or higher).
[0108] The amount of the solvent used is not particularly limited, but is, for example, 1 to 500 parts by mass, and preferably 5 to 300 parts by mass, per part by mass of the total amount of the phthalonitrile compound (II).
[0109] The reaction temperature is, for example, 50°C to 200°C, and preferably 90°C to 160°C or 120°C to 160°C. From the viewpoint of productivity, the reaction time is preferably 30 minutes to 50 hours, more preferably 1 to 40 hours, and further preferably 3 to 35 hours, and can be 20 hours or less or 15 hours or less.
[0110] As described above, by adjusting the amount of aluminum compound (III) used relative to phthalonitrile compound (II), compound (I) or compound (IV) can be preferentially synthesized, but the reaction mixture obtained by the above reaction may contain both compound (I) and compound (IV). As the coloring composition of the present invention, the above reaction mixture may be used as it is, or compound (I) and compound (IV) may be synthesized and isolated separately, and then mixed and used.
[0111] The method for isolating compound (I) and compound (IV) from the reaction mixture is not particularly limited, and various known methods can be used. For example, compound (I) and compound (IV) can be isolated by purification using column chromatography or the like.
[0112] [Colored resin composition] The present invention encompasses a colored composition containing the above-mentioned compound (I) and compound (IV) in a specific quantitative ratio, and a colored resin composition containing a resin (hereinafter, sometimes referred to as resin (B)). The colored resin composition of the present invention preferably contains the above-mentioned colored composition as a colorant (hereinafter, may be referred to as colorant (A)). It is preferable that the colored resin composition of the present invention further contains at least one (preferably both) of a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)). It is preferable that the colored resin composition of the present invention further contains a solvent (hereinafter, may be referred to as solvent (E)). The colored resin composition of the present invention may contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component may be used alone or in combination of two or more kinds, unless otherwise specified.
[0113] <Colorant (A)> The colorant (A) includes a coloring composition containing the compound (I) and the compound (IV) in a specific ratio. A preferred embodiment of the coloring composition contained as the colorant (A) is the same as the coloring composition described above.
[0114] The total content of compound (I) and compound (IV) in the total amount of colorant (A) is, for example, 20 to 100 mass%, preferably 40 mass or more, more preferably 50 mass or more, even more preferably 60 mass or more, and may be 80 mass or more.
[0115] The colorant (A) may further contain a colorant (hereinafter, may be referred to as colorant (A1)) different from the compound (I) and the compound (IV). The colorant (A1) may be either a dye or a pigment, but is preferably a pigment from the viewpoint of further suppressing unevenness in brightness after long-term use.
[0116] Examples of dyes include compounds classified as having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha).
[0117] Examples of dyes include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, thiazole dyes, oxazine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferred.
[0118] Specific examples of dyes include CI Solvent Yellow 4 (hereinafter, the description of CI Solvent Yellow will be omitted and only the numbers will be described. The same applies to the others), 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, and 189; CI Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI Solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 1 82, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 , 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 249, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; CI Acid dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 16 6, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Dyes, such as CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse dyes such as CI Disperse Blue 1, 14, 56, 60; CI Basic Red 1, 9, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic dyes, such as CI Basic Green 1; CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive dyes such as CI Reactive Red 36; CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Mordant dyes, such as CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; CI Vat Green 1; and other CI Vat dyes. These dyes may be one type of dye or a plurality of dyes for each color, or dyes of each color may be combined.
[0119] Examples of pigments include those classified as pigments in the Colour Index (published by The Society of Dyers and Colourists). Examples of pigments classified as pigments include yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 246, 254, 255, 264, 265, 266, 268, 269, 273, 291; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23, 25; Black pigments such as CI Pigment Black 1 and 7; With regard to these pigments, one kind of pigment or a plurality of pigments may be used for each color, and pigments of each color may be combined.
[0120] If necessary, the pigment may be subjected to a rosin treatment, a surface treatment using a pigment derivative having an acidic or basic group introduced therein, a graft treatment onto the pigment surface using a polymer compound or the like, a particle size reduction treatment using a sulfuric acid atomization method or the like, a washing treatment using an organic solvent or water to remove impurities, a removal treatment of ionic impurities using an ion exchange method or the like, etc. The particle size of the pigment is preferably approximately uniform.
[0121] The colorant (A1) may be appropriately selected depending on the desired spectrum. For example, when forming a green filter in a color filter, the colorant (A1) is preferably a yellow pigment, more preferably at least one selected from CI Pigment Yellow 138, 150, and 185, and further preferably CI Pigment Yellow 138 and / or 185.
[0122] When a yellow pigment is used as the colorant (A1), the content of the yellow pigment relative to 100 parts by mass of the total of the compound (I) and the compound (IV) is, for example, 1 to 200 parts by mass, preferably 5 to 150 parts by mass, more preferably 10 to 100 parts by mass, and further preferably 20 to 80 parts by mass. When the content of the yellow pigment is within the above range, the desired spectrum can be more easily obtained.
[0123] The content of the colorant (A) in the colored resin composition is, for example, 0.5 to 80 mass%, preferably 2 to 70 mass%, more preferably 8 to 50 mass%, and further preferably 10 to 40 mass%, based on the total amount of solids. When the content of the colorant (A) is within the above range, it becomes easier to obtain the desired spectrum and color density. In this specification, the term "total amount of solids" refers to the total amount of components excluding the solvent from the colored resin composition of the present invention. The total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography and gas chromatography.
[0124] <Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6]. Resin [K1]: a copolymer of at least one monomer (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond; Resin [K2]: a copolymer of (a), (b), and a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); Resin [K3]; copolymer of (a) and (c); Resin [K4]: A resin obtained by reacting a copolymer of (a) and (c) with (b); Resin [K5]: a resin obtained by reacting a copolymer of (b) and (c) with (a); Resin [K6]: A resin obtained by reacting a copolymer of (b) and (c) with (a) and further reacting it with a polyvalent carboxylic acid and / or a carboxylic anhydride.
[0125] Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Unsaturated dicarboxylic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Examples include unsaturated acrylates that contain a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the standpoint of copolymerization reactivity and solubility of the resulting resin in an aqueous alkaline solution.
[0126] (b) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In this specification, the term "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.
[0127] Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)").
[0128] Examples of (b1) include a monomer (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which a linear or branched unsaturated aliphatic hydrocarbon has been epoxidized, and a monomer (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which an alicyclic unsaturated hydrocarbon has been epoxidized.
[0129] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyl Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.
[0130] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100; manufactured by Daicel Corporation), 3,4-epoxytricyclo[5.2.1.0]phenylene ether, and the like. 2,6 ]decyl (meth)acrylate, a compound represented by formula (R1) and a compound represented by formula (R2) are included.
[0131] [ka]
[0132] [In formula (R1) and formula (R2), R ra and R rb represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X ra and X rb is a single bond, *-R rc -, *-R rc -O-, *-R rc -S- or *-R rc -NH-. R rc represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]
[0133] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group. Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group. R ra and R rb Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.
[0134] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group. X ra and X rb Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).
[0135] Examples of the compound represented by formula (R1) include compounds represented by any of formulas (R1-1) to (R1-15). Among them, compounds represented by formulas (R1-1), (R1-3), (R1-5), (R1-7), (R1-9) or (R1-11) to (R1-15) are preferred, and compounds represented by formulas (R1-1), (R1-7), (R1-9) or (R1-15) are more preferred.
[0136] [ka]
[0137] [ka]
[0138] Examples of the compound represented by formula (R2) include compounds represented by any of formulas (R2-1) to (R2-15). Among them, compounds represented by formulas (R2-1), (R2-3), (R2-5), (R2-7), (R2-9) or (R2-11) to (R2-15) are preferred, and compounds represented by formulas (R2-1), (R2-7), (R2-9) or (R2-15) are more preferred.
[0139] [ka]
[0140] [ka]
[0141] As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. As (b2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, and the like can be mentioned.
[0142] As (b3), a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.
[0143] As (b), (b1) is preferable in that the reliability of the heat resistance, chemical resistance, etc. of the obtained color filter can be improved. Furthermore, (b1-2) is more preferable in that the storage stability of the colored resin composition is excellent.
[0144] Examples of (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.02,6 ](meth)acrylic acid esters such as decene-8-yl (meth)acrylate (commonly known in the art as "dicyclopentenyl (meth)acrylate"), dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene chloro[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide; Examples of the copolymer include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. As (c), 2-ethylhexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, benzyl (meth)acrylate, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are preferred, and from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are more preferred.
[0145] In the resin [K1], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K1]: Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (b): 50 to 90 mol% It is more preferable that: When the ratio of the structural units of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter tend to be superior.
[0146] Resin [K1] can be produced, for example, by referring to the method described in the literature "Experimental Methods of Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, published on March 1, 1972) and the cited references described in said literature.
[0147] Specifically, a method is exemplified in which predetermined amounts of (a) and (b), a polymerization initiator, a solvent, etc. are placed in a reaction vessel, and the atmosphere is deoxygenated by, for example, replacing oxygen with nitrogen, and the mixture is heated and kept warm while stirring. The polymerization initiator and solvent used here are not particularly limited, and those commonly used in the relevant field can be used. For example, examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and examples of the solvent include those that dissolve each monomer, such as the solvent (E) described below.
[0148] The obtained copolymer may be used as it is after the reaction, or may be used after concentration or dilution, or may be used after extraction as a solid (powder) by a method such as reprecipitation. In particular, by using the solvent contained in the colored resin composition as the solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored resin composition, and therefore the manufacturing process of the colored resin composition can be simplified.
[0149] In the resin [K2], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K2]: Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1 to 65 mol% It is preferred that Structural units derived from (a): 5 to 40 mol% Structural units derived from (b): 5 to 80 mol% Structural units derived from (c): 5 to 60 mol% It is more preferable that: When the ratio of the structural units of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the resulting color filter tend to be superior.
[0150] The resin [K2] can be produced, for example, in the same manner as described above for producing the resin [K1]. It is possible.
[0151] In the resin [K3], the ratio of structural units derived from each of them is as follows among all structural units constituting the resin [K3]: Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40 to 98 mol% It is preferred that Structural units derived from (a): 10 to 50 mol% Structural units derived from (c): 50 to 90 mol% It is more preferable that: Resin [K3] can be produced, for example, in the same manner as described above as the method for producing resin [K1].
[0152] Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic acid anhydride contained in (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production method of resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that described for resin [K3].
[0153] Next, a part of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms contained in (b). Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b), a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours to produce the resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By adjusting the amount within this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. Since the reactivity of the cyclic ether is high and unreacted (b) is unlikely to remain, (b1) is preferable as (b) used in the resin [K4], and (b1-1) is more preferable. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c).The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b) and (c). The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.
[0154] Resin [K5] is produced in the first step by the same method as the above-mentioned resin [K1] to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as it is in the form of a solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are, respectively, Structural units derived from (b): 5 to 95 mol% Structural units derived from (c): 5 to 95 mol% It is preferred that Structural units derived from (b): 10 to 90 mol% Structural units derived from (c): 10 to 90 mol% It is more preferable that:
[0155] Furthermore, under the same conditions as in the manufacturing method of resin [K4], resin [K5] can be obtained by reacting the cyclic ether derived from (b) contained in the copolymer of (b) and (c) with the carboxylic acid or carboxylic anhydride contained in (a). The amount of (a) reacted with the copolymer is preferably 5 to 100 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.
[0156] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of the carboxylic acid anhydride include succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic acid anhydride used is preferably 0.1 to 1 mole per mole of the amount of (a) used.
[0157] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid copolymer resin [K1]; 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl acrylate / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, etc. [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, etc. [K3]; benzyl (meth)acrylate / (meth)acrylic acid copolymer to which glycidyl (meth)acrylate has been added, tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer to which glycidyl (meth)acrylate has been added, tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer to which glycidyl (meth)acrylate has been added, tricyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer to which glycidyl (meth)acrylate has been added, Resins such as resins to which acrylate has been added [K4]; resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid [K5]; resins obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid and then reacting it with tetrahydrophthalic anhydride, resins obtained by reacting a copolymer of 2-ethylhexyl (meth)acrylate / glycidyl (meth)acrylate / dicyclopentanyl (meth)acrylate with (meth)acrylic acid and then reacting it with succinic anhydride [K6], and the like can be mentioned. Among these, as the resin (B), at least one selected from the group consisting of copolymers (resin [K1], resin [K2]) containing a structural unit derived from at least one selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and resin [K6], is preferred, and resin [K1] and / or resin [K2] are more preferred.
[0158] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 500 to 100,000, more preferably 1,000 to 50,000, and even more preferably 3,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern tends to be improved.
[0159] The polydispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.
[0160] The acid value of the resin (B) is preferably 10 to 170 mg-KOH / g, more preferably 30 to 155 mg-KOH / g, and further preferably 50 to 140 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.
[0161] The content of resin (B) is preferably 7 to 80 mass%, more preferably 13 to 70 mass%, further preferably 17 to 60 mass%, and even more preferably 20 to 50 mass%, based on the total amount of solids in the colored resin composition. When the content of resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved. The content of resin (B) is, for example, 30 to 100 parts by mass, preferably 30 to 300 parts by mass, more preferably 80 to 280 parts by mass, and even more preferably 150 to 250 parts by mass, relative to 100 parts by mass of the total of compound (I) and compound (IV).
[0162] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.
[0163] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol poly(meth)acrylate (e.g., pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate), dipentaerythritol poly(meth)acrylate (e.g., dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate), tripentaerythritol poly(meth)acrylate (e.g., tri(meth)acrylate ... pentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate), tetrapentaerythritol poly(meth)acrylate (e.g., tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate), tris(2-(meth)acryloyloxyethyl)isocyanurate, alkoxylated pentaerythritol poly(meth)acrylate (e.g., ethoxylated pentaerythritol tri(meth)acrylate, ethoxylated alkoxylated pentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate), alkoxylated dipentaerythritol poly(meth)acrylates (e.g., ethoxylated dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol penta(meth)acrylate, propoxylated dipentaerythritol caprolactone-modified pentaerythritol poly(meth)acrylate (e.g., caprolactone-modified pentaerythritol tri(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate), caprolactone-modified dipentaerythritol poly(meth)acrylate (e.g., caprolactone-modified dipentaerythritol penta(meth)acrylate, caprolactone-modified dipentaerythritol hexa(meth)acrylate). Among them, at least one selected from the group consisting of trimethylolpropane tri(meth)acrylate and dipentaerythritol poly(meth)acrylate is preferable.
[0164] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.
[0165] The content of the polymerizable compound (C) is, for example, 5 to 65 mass%, preferably 6 to 50 mass%, more preferably 8 to 30 mass%, based on the total amount of solids in the colored resin composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate during colored pattern formation and the chemical resistance of the color filter tend to be further improved.
[0166] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and any known polymerization initiator can be used.
[0167] Examples of polymerization initiators that generate active radicals include alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds.
[0168] The O-acyloxime compound is a compound having a partial structure represented by formula (d1): In the following, * represents a bond.
[0169] [ka]
[0170] Examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N- acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, and the like. Commercially available products such as Irgacure OXE01, OXE02, and OXE03 (all manufactured by BASF), N-1919 (manufactured by ADEKA), PBG-314, PBG-317, PBG-326, PBG-327, and PBG-329 (all manufactured by Changzhou Strong Electronic New Materials Co., Ltd.) may also be used.Among them, the O-acyloxime compounds are N-acetyloxy-1-[4-(2-hydroxyethyloxy)phenylsulfanylphenyl]propan-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-acetyl ... At least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is preferred, and at least one selected from the group consisting of 2-[(acetyloxy)imino]-3-cyclohexyl-1-[4-(phenylsulfanyl)phenyl]propan-1-one, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine is more preferred. With these O-acyloxime compounds, a color filter with high brightness tends to be obtained.
[0171] The alkylphenone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.
[0172] [ka]
[0173] Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may also be used.
[0174] Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal. In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).
[0175] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ 2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.
[0176] The acylphosphine oxide compound may be 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.
[0177] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl) 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-7-10913).
[0178] Further, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with the polymerization initiator aid (D1) described below (especially amine compounds).
[0179] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyl dimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethylsulfonium p-toluenesulfonate, 4-acetoxyphenyl methylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.
[0180] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.
[0181] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, and further preferably 2 to 10 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, thereby improving the productivity of the color filter.
[0182] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator, or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
[0183] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc., and among these, 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may also be used.
[0184] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.
[0185] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
[0186] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.
[0187] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.
[0188] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc. can be mentioned.
[0189] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.
[0190] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.
[0191] The ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methyl ... Examples of the alkyl ether acetates include ethyl methoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.
[0192] Ketone solvents include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
[0193] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
[0194] Aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.
[0195] Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
[0196] Among the above-mentioned solvents, from the viewpoint of coatability and drying property, an organic solvent having a boiling point at 1 atm of 120° C. or more and 180° C. or less is preferred. As the solvent, at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone and N,N-dimethylformamide is preferred, and at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethyl lactate and ethyl 3-ethoxypropionate is more preferred.
[0197] It is also preferable to use an ether ester solvent and a ketone solvent in combination as the solvent (E). In this case, the ether ester solvent is preferably C 2-3 Alkylene glycol mono C 1-4 Alkyl ether acetate is preferred, propylene glycol mono C 1-4 Alkyl ether acetates are more preferred. As a ketone solvent, 4-hydroxy-4-methyl-2-pentanone is preferred. When an ether ester solvent and a ketone solvent are used in combination, the content of the ketone solvent is preferably 0.1 to 100 parts by mass, more preferably 0.5 to 50 parts by mass, and even more preferably 1.0 to 20 parts by mass, per 100 parts by mass of the total of the ether ester solvent and the ketone solvent.
[0198] The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored resin composition. In other words, the solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above range, the flatness during coating is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics and sensitivity tend to be good.
[0199] <Leveling agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms, which may have a polymerizable group in the side chain.
[0200] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule.Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).
[0201] The fluorine-based surfactant may include surfactants having a fluorocarbon chain in the molecule.Specific examples include Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by AGC Corporation (formerly Asahi Glass Co., Ltd.)) and E5844 (manufactured by Daikin Fine Chemical Research Institute Co., Ltd.).
[0202] Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).
[0203] The content of the leveling agent (F) is preferably 0.001 to 0.2 mass%, more preferably 0.002 to 0.1 mass%, and even more preferably 0.005 to 0.05 mass%, based on the total amount of the colored resin composition. This content does not include the content of the pigment dispersant described below. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
[0204] <Other ingredients> The colored resin composition may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as necessary.
[0205] <Method of producing colored resin composition> The colored resin composition can be prepared, for example, by mixing the colorant (A) and the resin (B), as well as the polymerizable compound (C), polymerization initiator (D), solvent (E), leveling agent (F), polymerization initiator aid (D1) and other components that are used as necessary. The colored resin composition after mixing may be filtered through a filter having a pore size of about 0.01 to 10 μm.
[0206] The coloring composition (i.e., compound (I) and compound (IV)) as the colorant (A), and the pigment as the colorant (A1) used as needed, may be used as a dispersion liquid in a uniformly dispersed state in a solution by adding a pigment dispersant and carrying out a dispersion treatment. The remaining components are mixed with such a dispersion liquid to a predetermined concentration, whereby the desired colored resin composition can be prepared. The compound (I), compound (IV) and pigment may be dispersed alone, or a plurality of types may be mixed and dispersed.
[0207] Examples of pigment dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLORENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.).
[0208] When a pigment dispersant is used, the amount thereof is preferably 5 parts by mass or more and 200 parts by mass or less, more preferably 10 parts by mass or more and 150 parts by mass or less, and even more preferably 20 parts by mass or more and 130 parts by mass or less, relative to 100 parts by mass of the colorant (A) in the dispersion (specifically, compound (I), compound (IV), and pigment). When the amount of the pigment dispersant used is within the above range, a dispersion in a more uniformly dispersed state tends to be obtained.
[0209] When the colorant (A) contains a dye, the dye may be dissolved in advance in a part or whole of the solvent (E) to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.
[0210] [Color Filter] Examples of the method for producing a colored pattern of a color filter from the colored resin composition of the present invention include a photolithography method, an inkjet method, and a printing method. Among them, the photolithography method is preferable. The photolithography method is a method in which the colored resin composition is applied to a substrate, dried to form a composition layer, and the composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film, which is a cured product of the composition layer, can be formed by not using a photomask during exposure and / or not developing.
[0211] The film thickness of the color filter (colored coating film or colored pattern) is, for example, 30 μm or less, preferably 20 μm or less, more preferably 6 μm or less, even more preferably 3 μm or less, even more preferably 1.5 μm or less, particularly preferably 0.5 μm or less, and is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.
[0212] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or soda lime glass with a silica-coated surface, a resin plate such as polycarbonate, polymethylmethacrylate, or polyethylene terephthalate, silicon, or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. On these substrates, another color filter layer, a resin layer, a transistor, a circuit, or the like may be formed. A silicon substrate having an HMDS treatment may also be used.
[0213] Formation of each color pixel (each color color filter) by photolithography can be performed with known or conventional equipment and conditions. For example, it can be produced as follows. First, a colored resin composition is applied onto a substrate, and volatile components such as a solvent are removed by heating and drying (pre-baking) and / or drying under reduced pressure to obtain a smooth composition layer. Examples of the application method include spin coating, slit coating, and slit and spin coating. The temperature when drying by heating is preferably 30 to 120°C, more preferably 50 to 110°C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When drying under reduced pressure, it is preferably performed under a pressure of 50 to 150 Pa at a temperature range of 20 to 25°C. The film thickness of the composition layer is not particularly limited and may be appropriately selected according to the film thickness of the desired color filter.
[0214] Next, the composition layer is exposed through a photomask for forming a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used. As the light source used for exposure, a light source that generates light with a wavelength of 250 to 450 nm is preferable. For example, light less than 250 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, and near 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps. It is preferable to use a reduced projection exposure device or a proximity exposure device such as a mask aligner and a stepper, since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and to accurately align the photomask and the substrate.
[0215] The composition layer after exposure is brought into contact with a developer for development, thereby forming a colored pattern on the substrate. The unexposed portion of the composition layer is dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Furthermore, the developer may contain a surfactant. The development method may be any of a paddle method, a dipping method, and a spray method. Furthermore, the substrate may be tilted at any angle during development. After development, it is preferable to wash with water.
[0216] Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 80 to 250° C., more preferably 100 to 245° C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.
[0217] The colored pattern and colored coating film obtained from the colored curable resin composition of the present invention have improved solvent resistance. When the colored pattern and colored coating film were subjected to the solvent resistance evaluation described below, the color difference ΔE * ab is preferably 3 or less, more preferably 2.3 or less, even more preferably 1.5 or less, still more preferably 1.0 or less, and particularly preferably 0.7 or less.
[0218] The colored pattern and colored coating film thus obtained are useful as color filters, and the color filters are useful as color filters for use in display devices (e.g., liquid crystal display devices, organic EL devices, etc.), electronic paper, solid-state imaging devices, etc. EXAMPLES
[0219] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples, and can be modified as long as it satisfies the spirit of the invention, and all such modifications are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".
[0220] In the following examples, the structures of the compounds were confirmed by mass spectrometry (MALDI-TOF MS; JMS-S3000 manufactured by JEOL Ltd.).
[0221] (Synthesis Example 1) <Preparation of Compound (II-1)> Under a nitrogen atmosphere, 23 parts of 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 25 parts of 2,6-dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 20 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 160 parts of acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed and heated to 80°C, and then stirred at the same temperature for 10 hours. The reaction liquid was cooled to room temperature (18 to 24°C) and filtered to obtain filtrate A and residue A. Residue A was washed with 160 parts of acetonitrile, and the obtained acetonitrile solution and filtrate A were combined, and the solvent in the solution was distilled off. The obtained residue was washed with 160 parts of ion-exchanged water and dried, and 38 parts of a compound represented by formula (II-1) (hereinafter, compound (II-1)) were obtained as a colorless solid (yield 92%).
[0222] [ka]
[0223] (Synthesis Example 2) <Preparation of compound (I-e1)> Under a nitrogen atmosphere, 9.0 parts of the compound (II-1) produced in Synthesis Example 1, 1.3 parts of anhydrous aluminum chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), 83.0 parts of triethylene glycol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 8.3 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and heated at 140 ° C. for 10 hours. After the reaction was completed, the reaction liquid was cooled to room temperature (18 to 24 ° C.), and 103 parts of ethyl acetate were poured in. The precipitated solid was filtered, 103 parts of ion-exchanged water was poured in, and the mixture was stirred for 30 minutes or more, and then filtered and dried under reduced pressure. In addition, 103 parts of acetone was poured in, and the mixture was stirred for 30 minutes or more, and then filtered and dried under reduced pressure. As a result, 2.41 parts (yield 24%) of a compound represented by formula (I-e1) (hereinafter, compound (I-e1)) were obtained.
[0224] [ka]
[0225] <Identification of compound (I-e1)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 995 Exact Mass: 994
[0226] (Synthesis Example 3) <Synthesis of compound (IV-e1)> Except for changing the amount of anhydrous aluminum chloride (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) to 2.6 parts, the same procedure as in Synthesis Example 2 was followed to obtain 4.1 parts (yield 40%) of a compound represented by formula (IV-e1) (hereinafter, compound (IV-e1)).
[0227] [ka]
[0228] <Identification of compound (IV-e1)> (Mass spectrometry) Ionization mode = MALDI-TOF - : m / z= 1053 Exact Mass: 1054
[0229] (Resin synthesis example 1) <Synthesis of Resin B-1> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixed solution of 289 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution with a solid content of 35.1% and a viscosity of 125 mPas measured with a Brookfield viscometer (23°C). The weight average molecular weight Mw of the resulting copolymer was 9.2×10 3 The resin B-1 had a polydispersity of 2.08 and an acid value calculated as solid content of 77 mg-KOH / g.
[0230] [ka]
[0231] (Resin synthesis example 2) <Synthesis of Resin B-2> A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 350 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85°C with stirring. Next, 70 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ] A mixture of 202 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio), 78 parts of vinyl toluene (mixture of isomers), and 100 parts of propylene glycol monomethyl ether acetate was added dropwise over 4 hours. Meanwhile, a solution of 33 parts of polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 167 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the dropwise addition of the initiator solution was completed, the mixture was kept at 85°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-2) solution with a viscosity of 431 mPas measured with a B-type viscometer (23°C) and a solid content of 38.1%. The weight average molecular weight Mw of the resulting copolymer was 1.04×104 The polydispersity was 2.03, and the acid value calculated as solid content was 139 mg-KOH / g. Resin B-2 has the following structural units.
[0232] [ka]
[0233] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Equipment: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: Tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of the analytical sample: 0.001 to 0.01% by mass Injection volume: 50μL Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.
[0234] <Preparation of Coloring Composition> Example 1 A colored composition (M-1) was obtained by mixing 0.297 parts of the compound (I-e1), 0.003 parts of the compound (IV-e1), 4.15 parts of propylene glycol monomethyl ether acetate, and 0.6 parts of diacetone alcohol.
[0235] Example 2 A colored composition (M-2) was obtained in the same manner as in Example 1, except that the amount of compound (I-e1) was changed to 0.285 parts and the amount of compound (IV-e1) was changed to 0.015 parts.
[0236] Example 3 A colored composition (M-3) was obtained in the same manner as in Example 1, except that the amount of compound (I-e1) was changed to 0.255 parts and the amount of compound (IV-e1) was changed to 0.045 parts.
[0237] Comparative Example 1 A colored composition (M-4) was obtained in the same manner as in Example 1, except that the amount of compound (I-e1) was changed to 0.225 parts and the amount of compound (IV-e1) was changed to 0.075 parts.
[0238] Comparative Example 2 A colored composition (M-5) was obtained in the same manner as in Example 1, except that the amount of compound (I-e1) was changed to 0.3 parts and compound (IV-e1) was not used.
[0239] (Examples A1 to A3 and Comparative Examples A1 to A2) (A-1) Preparation of Dispersion <Dispersion liquid preparation example 1> 5.0 parts of the coloring composition (M-1) obtained in Example 1, 0.21 parts of a dispersant (BYKLPN-6919 manufactured by BYK) (solid content equivalent), and 0.21 parts of resin B-2 (solid content equivalent) were mixed, 18 parts of 0.2 mm zirconia beads were added, and the mixture was shaken. The zirconia beads were removed by filtration to obtain a dispersion (P-1).
[0240] <Dispersion Liquid Preparation Example 2 to Dispersion Liquid Preparation Example 5> Dispersions (P-2) to (P-5) were obtained in the same manner as in Dispersion Preparation Example 1, except that the colored composition (M-1) in Dispersion Preparation Example 1 was changed to the following colored composition. Dispersion (P-2): Colored composition (M-2) obtained in Example 2 Dispersion (P-3): Colored composition (M-3) obtained in Example 3 Dispersion (P-4): Colored composition (M-4) obtained in Comparative Example 1 Dispersion (P-5): Colored composition (M-5) obtained in Comparative Example 2
[0241] (A-2) Preparation of colored resin composition The colored resin compositions of Examples A1 to A3 and Comparative Examples A1 to A2 were obtained by mixing the components (solid content equivalent) shown in Table 9. In addition, in the colored resin compositions of Examples A1 to A3 and Comparative Examples A1 to A2, propylene glycol monomethyl ether acetate was mixed so that the solid content was 15 mass%.
[0242] [Table 9]
[0243] In Table 9, each component represents the following compound. Resin (B-1): Resin B-1 (solid content equivalent) Polymerizable compound (C-1): Dipentaerythritol polyacrylate: Trade name A-9570: manufactured by Shin-Nakamura Chemical Co., Ltd. Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine: Trade name PBG-327: O-acyloxime compound: Manufactured by Changzhou Strong Electronic New Materials Co., Ltd. Leveling agent (F-1): Polyether modified silicone oil: Product name: Toray Silicone SH8400: Manufactured by Toray Dow Corning Co., Ltd.
[0244] (A-3) Preparation of colored coating film Each colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated), and then prebaked at 100°C for 3 minutes to form a colored composition layer. After cooling, the substrate was exposed to light at 100 mJ / cm2 in the air without using a photomask using an exposure machine (TME-150RSK; Topcon Corporation). 2 The colored composition layer after the light irradiation was post-baked in an oven at 230°C for 20 minutes to obtain a colored coating film. After cooling, the thickness of the obtained colored coating film was measured using a thickness measuring device (DEKTAK3; manufactured by Nippon Shinku Gijutsu Co., Ltd.). The thickness of the obtained colored coating film was the same 2.0 μm in all examples and comparative examples.
[0245] (A-4) Transmittance measurement The obtained colored coating film was subjected to spectrometry using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) to measure the transmittance. The transmittance at a wavelength of 505 nm of the colored coating film made of the colored resin composition of Comparative Example A2 was used as a standard, and a colored coating film having an improved transmittance at a wavelength of 505 nm compared to Comparative Example A2 was marked with ◯, a colored coating film having the same transmittance at a wavelength of 505 nm as Comparative Example A2 was marked with △, and a colored coating film having a lower transmittance at a wavelength of 505 nm compared to Comparative Example A2 was marked with ×. The results are shown in the "Transmittance at 505 nm" column in Table 10.
[0246] (A-5) Solvent resistance evaluation A solvent resistance test was conducted in which the obtained colored coating film was immersed in N-methylpyrrolidone at 23°C for 40 minutes. The colored coating film was evaluated for solvent resistance by evaluating its chromaticity before and after the solvent resistance test. The chromaticity of the colored coating film was evaluated by measuring the spectrum using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) and measuring the xy chromaticity coordinates (x, y) and Y in the CIE XYZ color system using the characteristic function of the C light source. The color difference ΔE was calculated from the xy chromaticity coordinates (x, y) and Y measured before and after the solvent resistance test using the method described in JIS Z 8730:2009 (7. Calculation method of color difference). * ab was calculated. Color difference △E * The smaller the ab value, the smaller the color change and the better the solvent resistance. * If ab is 3 or less, the coating film can be said to have no practical problems as a color filter. In addition, if the solvent resistance of the colored coating film is good, it can be said that the solvent resistance of a color filter made from the same colored resin composition is also good.
[0247] [Table 10]
[0248] (Examples B1 to B6 and Comparative Examples B1 to B2) (B-1) Preparation of Dispersion <Dispersion Liquid Preparation Example 6> CI Pigment Green 58 14 parts Acrylic pigment dispersant (solid content equivalent) 1.9 parts Resin (B-2) (solid content equivalent) 6.5 parts Propylene glycol monomethyl ether acetate 78 parts The above ingredients were mixed and the pigment was dispersed using a bead mill to obtain a dispersion liquid (P-6).
[0249] <Dispersion Liquid Preparation Example 7> CI Pigment Yellow 138 15 parts Acrylic pigment dispersant (solid content equivalent) 4.5 parts Resin (B-1) (solid content equivalent) 4.5 parts Propylene glycol monomethyl ether acetate 76 parts The above ingredients were mixed and the pigment was dispersed using a bead mill to obtain a dispersion (P-7).
[0250] <Dispersion Liquid Preparation Example 8> CI Pigment Yellow 185 10 parts Acrylic pigment dispersant 4.0 parts Resin (B-2) (solid content equivalent) 3.6 parts Propylene glycol monomethyl ether acetate 82 parts The above ingredients were mixed and the pigment was dispersed using a bead mill to obtain a dispersion liquid (P-8).
[0251] (A-2) Preparation of colored resin composition The colored resin compositions of Examples B1 to B6 and Comparative Examples B1 to B2 were obtained by mixing the components shown in Table 11. In preparing the colored resin compositions, the ratio of the colorant in the solid content of the colored resin composition was 40 mass% in Examples B1 to B3 and Comparative Example B1, and 35 mass% in Examples B4 to B6 and Comparative Example B2.
[0252] [Table 11]
[0253] In Table 11, each component represents the following compound. Dispersions (P-1) to (P-3): Dispersions (P-1) to (P-3) obtained in Dispersion Preparation Examples 1 to 3, respectively Dispersions (P-6) to (P-8): Dispersions (P-6) to (P-8) obtained in Dispersion Preparation Examples 6 to 8, respectively Resin (B-1): Resin B-1 (solid content equivalent) Polymerizable compound (C-1): Dipentaerythritol polyacrylate: Trade name A-9570: manufactured by Shin-Nakamura Chemical Co., Ltd. Polymerization initiator (D-1): N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine: Trade name PBG-327: O-acyloxime compound: Manufactured by Changzhou Strong Electronic New Materials Co., Ltd. Leveling agent (F-1): Polyether modified silicone oil: Product name: Toray Silicone SH8400: Manufactured by Toray Dow Corning Co., Ltd. Solvent (E-1): Propylene glycol monomethyl ether acetate In addition, the amount shown in the column for solvent (E-1) in Table 11 indicates the total amount including the amount of propylene glycol monomethyl ether acetate contained in resin (B-1).
[0254] (B-3) Preparation of colored coating film Each colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated), and then prebaked at 100°C for 3 minutes to form a colored composition layer. After cooling, the substrate was exposed to light at 100 mJ / cm2 in the air without using a photomask using an exposure machine (TME-150RSK; Topcon Corporation). 2 The colored composition layer after the light irradiation was post-baked in an oven at 230°C for 20 minutes to obtain a colored coating film. After cooling, the thickness of the obtained colored coating film was measured using a thickness measuring device (DEKTAK3; manufactured by Nippon Shinku Gijutsu Co., Ltd.). The thickness of the obtained colored coating film was the same 2.0 μm in all examples and comparative examples.
[0255] (B-4) Evaluation of brightness unevenness suppression The obtained colored coating film was subjected to a light irradiation test in which a xenon lamp light was irradiated for 48 hours using a light resistance tester (Suntest CPS+: manufactured by Toyo Seiki Seisakusho Co., Ltd.). The colored coating film before and after the light irradiation test was measured for spectroscopy using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ color system were measured using the characteristic function of the C light source. ΔY was calculated from the formula "stimulus value Y before light irradiation test - stimulus value Y after light irradiation test" and evaluated according to the following evaluation criteria. The results are shown in Table 12. When the brightness change rate under these measurement conditions is 2.5 or less (especially 1.5 or less), the brightness difference between the peripheral part and the center part of the colored filter after long-term use becomes difficult for the human eye to distinguish, and it can be said that the color filter has sufficient performance. Brightness unevenness suppression ◎:ΔY is 1.5 or less Suppression of uneven brightness: ΔY is more than 1.5 and less than 2.5 Suppression of uneven brightness ×: ΔY exceeds 2.5
[0256] [Table 12]
[0257] From the results in Table 12, it was found that a colored coating film with suppressed uneven brightness can be produced by using a colored composition containing compound (I). Also, as is clear from the results in Table 10, by using a colored composition containing compound (I) and compound (IV) in a specific quantitative ratio, a colored coating film with both enhanced transmittance at 505 nm and solvent resistance as well as the above-mentioned effect of suppressing uneven brightness could be produced.
Claims
1. A coloring composition comprising a compound represented by formula (I) and a compound represented by formula (IV), A coloring composition, comprising a compound represented by formula (IV) in an amount of 0.5 parts by mass or more and 30 parts by mass or less based on 100 parts by mass of the compound represented by formula (I). 【Chemistry 1】 [In formula (I), R 1A ~R 16A each independently represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and —CH 2 - may be replaced by -O- or -CO-. 1A ~R 16A at least one of the formulas (ia), (ib), or (ic) represents a group represented by the formula; when there are a plurality of groups represented by the formula (ia), they may be the same or different; when there are a plurality of groups represented by the formula (ib), they may be the same or different; and when there are a plurality of groups represented by the formula (ic), they may be the same or different.] 【Chemistry 2】 [In formula (ia), R a1 ~R a5 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. a1 ~R a5 At least one of the groups represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] 【Chemistry 3】 [In formula (ib), R b1 ~R b7 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. b1 ~R b7 At least one of represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] 【Chemistry 4】 [In formula (ic), R c1 ~R c7 each independently represents a hydrogen atom, a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O- or -CO-. c1 ~R c7 At least one of represents a halogen atom, a carboxy group, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. * represents a bond.] 【Chemistry 5】 [In formula (IV), R 1B ~R 16B each independently represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic), and —CH 2 - may be replaced by -O- or -CO-. 1B ~R 16B at least one of represents a group represented by formula (ia), a group represented by formula (ib), or a group represented by formula (ic); when there are a plurality of groups represented by formula (ia), they may be the same or different; when there are a plurality of groups represented by formula (ib), they may be the same or different; and when there are a plurality of groups represented by formula (ic), they may be the same or different. X is a halogen atom, a hydroxyl group, or OR M R represents a group. M represents a hydrocarbon group having 1 to 6 carbon atoms.
2. Contains a colorant and a resin, A colored resin composition, wherein the colorant comprises the colored composition according to claim 1.
3. The colored resin composition according to claim 2, further comprising a polymerizable compound and a polymerization initiator.
4. A color filter formed from the colored resin composition according to claim 3.
5. A display device comprising the color filter according to claim 4.
6. A solid-state imaging device comprising the color filter according to claim 4 .
Citation Information
Patent Citations
Color filter and liquid crystal display device using the same
JP2009192661A