WO2015133649A1

WO2015133649A1 - Novel compound and colored photosensitive composition

Info

Publication number: WO2015133649A1
Application number: PCT/JP2015/056982
Authority: WO
Inventors: 裕介久保田; 祐史小田
Original assignee: 株式会社Adeka
Priority date: 2014-03-06
Filing date: 2015-03-10
Publication date: 2015-09-11
Also published as: CN106133066B; JP2017057235A; JP6352653B2; JPWO2015133649A1; CN106133066A; KR102326662B1; KR20170116565A

Abstract

　The present invention provides: a novel compound having excellent solvent resistance and heat resistance, as well as excellent waveform control properties in the optical absorption spectrum thereof, and which is suitable for a dye; and a colored photosensitive composition (colored alkali developable photosensitive composition) and color filter which use the compound (dye); a compound represented by general formula (1), particularly a compound in which one or both of R⁴ and R⁷ in general formula (1) are hydroxyl groups or halogen atoms, or C1-8 alkyl groups substituted with a halogen atom or C1-8 alkoxy groups which may be substituted with a halogen atom, being used as the dye. The specific details of general formula (1) are as described in the specification.

Description

Novel compound and colored photosensitive composition

The present invention relates to a novel compound suitable for a dye which is designed to have a desired hue, has a good performance as a light absorber, and has improved heat resistance. Furthermore, the present invention relates to a colored photosensitive composition that can be polymerized by energy rays using the dye, and a color filter that uses the colored photosensitive composition.

Compounds having high intensity absorption for specific light include recording layers of optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.

In an optical filter for an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display device (CRT), a fluorescent display tube, a field emission display, etc., 300 Various compounds that absorb light having a wavelength of ˜1100 nm are used as light absorbers. These light absorbers are required to have particularly sharp light absorption, that is, excellent waveform controllability such as a small half-value width of λmax and that the function is not lost by light or heat. Yes.

There is a color filter as an optical filter mainly used for a liquid crystal display (LCD). In general, three primary colors of RGB have been used for a color filter, but it is difficult to have a pure RGB hue with a single color material, and a pure RGB hue using a plurality of color materials. Efforts have been made to get closer to. Therefore, color materials such as yellow, orange and purple are required instead of RGB.

Organic and / or inorganic pigments have been used as light absorbers for color filters due to their high heat resistance. However, since they are pigments, there is a problem in that the luminance of a display device is lowered. This problem has been solved by increasing the brightness of the. However, with the trend toward lower power consumption, development of color filters using dyes has become active.

In recent years, color filters used in solid-state imaging devices have been required to have thin colored patterns from the viewpoint of improving image quality, and in order to reduce the thickness, it is necessary to increase the dye density in terms of color density. . In addition, a large amount of dye must be added even when the molar absorption coefficient of the dye is low.
However, when the dye concentration is increased, elution and precipitation of pigment from the formed pixels are observed after film formation, and when heat treatment (post bake) is performed after film formation, between adjacent pixels and in the laminated structure The problem is that color mixing tends to occur between the upper and lower layers.

Patent Document 1 discloses a dye monomer and a polymer thereof, Patent Document 2 discloses a hologram recording material containing a dye having a polymerizable group, and Patent Document 3 discloses A two-photon absorption optical recording material containing a dye having a polymerizable group is disclosed, and Patent Document 4 discloses a photosensitive coloring composition containing a triarylmethane dye monomer having a polymerizable group in an anion. Is disclosed. However, the compounds having a polymerizable group described in these documents are not satisfactory in terms of solvent resistance and heat resistance.

Japanese Patent Laid-Open No. 11-246627 US Patent Publication No. 2007/077041 US Patent Publication No. 2009/088890 Japanese Patent No. 4266627

Therefore, an object of the present invention is to provide a novel compound that is excellent in solvent resistance and heat resistance, has excellent waveform controllability in a light absorption spectrum, and is suitable for a dye. Another object of the present invention is to provide a colored photosensitive composition (colored alkali-developable photosensitive composition) using the above dye. Another object of the present invention is an optical filter using the colored photosensitive composition (colored alkali-developable photosensitive composition), particularly suitable for an image display device such as a liquid crystal display panel without reducing luminance. It is to provide a color filter.

As a result of intensive investigations, the present inventors have found that a compound having a specific structure is excellent in heat resistance, excellent in solvent resistance in a colored photosensitive composition (colored alkali-developable photosensitive composition), Knowing that the light absorption spectrum has excellent waveform controllability, and that the colored photosensitive composition (colored alkali-developable photosensitive composition) does not decrease the luminance of the optical filter (particularly the color filter), and does not decrease the liquid crystal display. The present inventors have found that it is suitable for a color filter for an image display device such as a panel and reached the present invention.
This invention is made | formed based on the said knowledge, and provides the compound represented by following General formula (1).

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represents a hydrogen atom or a halogen atom,
A cyano group, a nitro group, a hydroxyl group, or an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms with a halogen atom,
An alkoxy group having 1 to 8 carbon atoms substituted or unsubstituted by a halogen atom,
An aryl group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
An aryloxy group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
An arylthio group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
A substituted or unsubstituted arylalkenyl group having 8 to 20 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 20 carbon atoms, which is substituted with a halogen atom,
R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group or a nitro group,
Substituted with nitro group, carboxyl group, sulfonic acid group, hydroxyl group or halogen atom, substituted with carboxyl ester, sulfonic acid group ester, carboxyl salt or sulfonic acid salt, or unsubstituted An alkyl group having 1 to 8 carbon atoms,
Substituted with alkyl group having 1 to 4 carbon atoms, halogen atom, cyano group, vinyl group, nitro group, carboxyl group, sulfonic acid group or hydroxyl group, ester of carboxyl group, ester of sulfonic acid group, carboxyl group A phenyl group which is substituted or unsubstituted with a salt or a salt of a sulfonic acid group,
Substituted with alkyl group having 1 to 4 carbon atoms, halogen atom, cyano group, vinyl group, nitro group, carboxyl group, sulfonic acid group or hydroxyl group, ester of carboxyl group, ester of sulfonic acid group, carboxyl group It represents an unsubstituted benzyl group that is substituted with a salt or a salt of a sulfonic acid group.
R ¹ and R ¹¹ , R ² and R ¹² , R ⁵ and R ¹³ , R ⁶ and R ¹⁴ , R ⁹ and R ^15, and R ¹⁰ and R ¹⁶ may be linked to form a 6-membered ring. ,
R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , and R ¹⁵ and R ¹⁶ may be linked to form a 3- to 6-membered heterocyclic ring,
R ³ and R ⁴ and R ⁷ and R ⁸ are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR ¹⁷ R ¹⁸ , CO, NR ¹⁹ , PR ²⁰ or SO ₂ to form a ring. You may,
X represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, CR ¹⁷ R ¹⁸ , CO, NR ¹⁹ , PR ²⁰ or SO ₂ ;
R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ are each independently a hydrogen atom, a halogen atom-substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, or a halogen atom. Represents a substituted alkoxy group having 1 to 8 carbon atoms,
An ^q− represents a q-valent anion, q represents 1 or 2, and p represents a coefficient for keeping the charge neutral.
However, any one or more of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is a hydrogen atom. )
Moreover, this invention provides the coloring photosensitive composition containing the dye (A) containing the said compound, the polymeric compound (B) which has an ethylenically unsaturated bond, and a photoinitiator (C). .
Moreover, this invention provides the color filter for display devices which comprises the hardened | cured material of the said colored photosensitive composition, and this hardened | cured material in part at least.

The compound of the present invention is excellent in solvent resistance and heat resistance, and further has excellent waveform controllability in a light absorption spectrum, and is suitable as a dye. Moreover, the colored photosensitive composition (colored alkali-developable photosensitive composition) using the compound of the present invention as a dye does not decrease the luminance and is suitable as a color filter for an image display device such as a liquid crystal display panel.

FIG. 1 shows compound No. 1 which is the compound of the present invention synthesized in Example 1. ¹ shows a ¹ H-NMR chart of 13; 2 shows compound No. 1 which is the compound of the present invention synthesized in Example 1. FIG. ¹ shows a ¹ H-NMR chart of 25. 3 shows compound No. 1 which is the compound of the present invention synthesized in Example 1. 26 shows the ¹ H-NMR chart of No. 26. 4 shows compound No. 1 which is the compound of the present invention synthesized in Example 1. ¹ shows a ¹ H-NMR chart of 35.

Hereinafter, the present invention will be described in detail based on preferred embodiments.
The present invention is a novel compound represented by the above general formula (I).
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ in the compound represented by the general formula (I) are each independently a hydrogen atom or Represents a halogen atom,
A cyano group, a nitro group, a hydroxyl group, or an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms with a halogen atom,
An alkoxy group having 1 to 8 carbon atoms substituted or unsubstituted by a halogen atom,
An aryl group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
An aryloxy group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
An arylthio group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
It represents an arylalkenyl group having 8 to 20 carbon atoms substituted or unsubstituted with a halogen atom, or an arylalkyl group having 7 to 20 carbon atoms substituted or substituted with a halogen atom.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. The same applies to all halogen atoms in the following description.

Examples of the unsubstituted alkyl group having 1 to 8 carbon atoms include methyl group, ethyl group, propyl group, iso-propyl group, butyl group, sec-butyl group, tert-butyl group, iso-butyl group, amyl group, iso-amyl group, tert-amyl group, hexyl group, 2-hexyl group, 3-hexyl group, cyclohexyl group, 1-methylcyclohexyl group, heptyl group, 2-heptyl group, 3-heptyl group, iso-heptyl group, Examples include tert-heptyl group, 1-octyl group, iso-octyl group, tert-octyl group and the like.

As the alkyl group having 1 to 8 carbon atoms substituted with a cyano group, a nitro group, a hydroxyl group or a halogen atom, a part or all of the hydrogen atoms in the alkyl group having 1 to 8 carbon atoms may be a cyano group. , A group substituted with one or more selected from a nitro group, a hydroxyl group or a halogen atom.

Examples of the unsubstituted alkoxy group having 1 to 8 carbon atoms include methyloxy group, ethyloxy group, iso-propyloxy group, butyloxy group, sec-butyloxy group, tert-butyloxy group, iso-butyloxy group, amyloxy group, iso -Amyloxy group, tert-amyloxy group, hexyloxy group, 2-hexyloxy group, 3-hexyloxy group, cyclohexyloxy group, 4-methylcyclohexyloxy group, heptyloxy group, 2-heptyloxy group, 3-heptyloxy group Group, iso-heptyloxy group, tert-heptyloxy group, 1-octyloxy group, iso-octyloxy group, tert-octyloxy group and the like.

Examples of the alkoxy group having 1 to 8 carbon atoms substituted with a halogen atom include groups in which part or all of the hydrogen atoms in the alkoxy group having 1 to 8 carbon atoms are substituted with a halogen atom. It is done.

Examples of the unsubstituted aryl group having 6 to 20 carbon atoms include a phenyl group and a naphthyl group.

As the aryl group having 6 to 20 carbon atoms substituted with a halogen atom, part or all of the hydrogen atoms in the above unsubstituted aryl group having 6 to 20 carbon atoms are substituted with a halogen atom. Groups.

Examples of the unsubstituted aryloxy group having 6 to 20 carbon atoms include a phenyloxy group and a naphthyloxy group.

As the aryloxy group having 6 to 20 carbon atoms substituted with a halogen atom, part or all of the hydrogen atoms in the above unsubstituted aryloxy group having 6 to 20 carbon atoms are substituted with halogen atoms. Group.

Examples of the unsubstituted arylthio group having 6 to 20 carbon atoms include a phenylthio group and a naphthylthio group.

As the arylthio group having 6 to 20 carbon atoms substituted with a halogen atom, part or all of the hydrogen atoms in the above unsubstituted arylthio group having 6 to 20 carbon atoms are substituted with a halogen atom. Groups.

Examples of the unsubstituted arylalkenyl group having 8 to 20 carbon atoms include benzyl group, phenethyl group, diphenylmethyl group, triphenylmethyl group and the like.

As the arylalkenyl group having 8 to 20 carbon atoms substituted with a halogen atom, part or all of the hydrogen atoms in the above unsubstituted arylalkenyl group having 8 to 20 carbon atoms is substituted with a halogen atom. Group.

Examples of the unsubstituted arylalkyl group having 7 to 20 carbon atoms include a styryl group and a cinnamyl group.

As the arylalkyl group having 7 to 20 carbon atoms substituted with a halogen atom, a part or all of the hydrogen atoms in the unsubstituted arylalkyl group having 7 to 20 carbon atoms is substituted with a halogen atom. Group.

R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group or a nitro group,
Substituted with nitro group, carboxyl group, sulfonic acid group, hydroxyl group or halogen atom, substituted with carboxyl ester, sulfonic acid group ester, carboxyl salt or sulfonic acid salt, or unsubstituted An alkyl group having 1 to 8 carbon atoms,
Substituted with alkyl group having 1 to 4 carbon atoms, halogen atom, cyano group, vinyl group, nitro group, carboxyl group, sulfonic acid group or hydroxyl group, ester of carboxyl group, ester of sulfonic acid group, carboxyl group A phenyl group which is substituted or unsubstituted with a salt or a salt of a sulfonic acid group,
Substituted with alkyl group having 1 to 4 carbon atoms, halogen atom, cyano group, vinyl group, nitro group, carboxyl group, sulfonic acid group or hydroxyl group, ester of carboxyl group, ester of sulfonic acid group, carboxyl group It represents an unsubstituted benzyl group that is substituted with a salt or a salt of a sulfonic acid group.
However, any one or more of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ must be a hydrogen atom.

Examples of the unsubstituted alkyl group having 1 to 8 carbon atoms include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso -Amyl group, tert-amyl group, hexyl group, 2-hexyl group, 3-hexyl group, cyclohexyl group, 1-methylcyclohexyl group, heptyl group, 2-heptyl group, 3-heptyl group, iso-heptyl group, tert -Heptyl group, 1-octyl group, iso-octyl group, tert-octyl group and the like.

A part or all of the above alkyl group may be substituted with a nitro group, a carboxyl group, a sulfonic acid group, a hydroxyl group or a halogen atom, or an ester of a carboxyl group, an ester of a sulfonic acid group, or a salt of a carboxyl group Alternatively, it may be substituted with a salt of a sulfonic acid group.
Examples of the carboxyl group ester include esters having 1 to 4 carbon atoms such as methyl ester, ethyl ester, iso-propyl ester, and butyl ester.
Examples of the carboxyl group salt or the sulfonic acid group salt include alkali metal salts such as lithium salt, sodium salt and potassium salt, and amine salts such as ammonium salt, ethanolamine salt, diethanolamine salt and triethanolamine salt.

Part or all of the above phenyl group and benzyl group may be substituted with a halogen atom, a cyano group, a vinyl group, a nitro group, a carboxyl group, or a sulfonic acid group, and an ester of a carboxyl group or an ester of a sulfonic acid group , A salt of a carboxyl group or a salt of a sulfonic acid group may be substituted. Examples of the ester and the salt include the above examples.

R ¹ and R ¹¹ , R ² and R ¹² , R ⁵ and R ¹³ , R ⁶ and R ¹⁴ , R ⁹ and R ^15, and R ¹⁰ and R ¹⁶ may be linked to form a 6-membered ring. ,
R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , and R ¹⁵ and R ¹⁶ may be linked to form a 3- to 6-membered heterocyclic ring,
R ³ and R ⁴ and R ⁷ and R ⁸ are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR ¹⁷ R ¹⁸ , CO, NR ¹⁹ , PR ²⁰ or SO ₂ to form a ring. It may be.

Examples of the 6-membered ring that can be formed by linking include a piperidine ring, a pyridine ring, a pyrimidine ring, a quinoline ring, and an isoquinoline ring.
Examples of the 3- to 6-membered heterocyclic ring that can be formed by coupling include piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiomorpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, isoquinoline Ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring, isoxazolidine ring, isothiazolidine ring and the like. These 6-membered rings and heterocyclic rings may be condensed or substituted with other rings.

X represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, CR ¹⁷ R ¹⁸ , CO, NR ¹⁹ , PR ²⁰ or SO ₂ ;
R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ are each independently a hydrogen atom, a halogen atom-substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, or a halogen atom. Represents a substituted alkoxy group having 1 to 8 carbon atoms, an unsubstituted alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms substituted with a halogen atom, and the number of unsubstituted carbon atoms Examples of the alkoxy group having 1 to 8 carbon atoms or the alkoxy group having 1 to 8 carbon atoms substituted with a halogen atom include those described above.

In the general formula (I), pAn ^q− represents a q-valent anion, q represents 1 or 2, and p represents a coefficient for keeping the charge neutral. Examples of the anion represented by An ^q- include monovalent ions such as chloride ions, bromide ions, iodide ions and fluoride ions; perchlorate ions, chlorate ions and thiocyanates. Inorganic anions such as acid ion, hexafluorophosphate ion, hexafluoroantimonate ion, tetrafluoroborate ion; methanesulfonate ion, dodecylsulfonate ion, benzenesulfonate ion, toluenesulfonate ion, trifluoromethanesulfone Acid ion, naphthalene sulfonate ion, diphenylamine-4-sulfonate ion, 2-amino-4-methyl-5-chlorobenzenesulfonate ion, 2-amino-5-nitrobenzenesulfonate ion, phthalocyanine sulfonate ion, polymerizable substitution Have a group JP-A-10-235999, JP-A-10-337959, JP-A-11-102888, JP-A-2000-108510, JP-A-2000-168223, JP-A-2001-209969, JP-A-2001-322354, JP-A-2006-. Organics such as sulfonate ions described in H.248180, JP-A-2006-297907, JP-A-8-253705, JP-T-2004-503379, JP-A-2005-336150, International Publication No. 2006/28006, etc. Sulfonic acid type anions: Octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) phosphone Organic phosphates such as acid ions , Bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4-ethylcyclohexanesulfonate ion, tetrakis (pentafluorophenyl) borate ion, tris (fluoroalkylsulfonyl) carboanion, etc. ,
As a bivalent thing, a benzene disulfonic acid ion, a naphthalene disulfonic acid ion, etc. are mentioned, for example.
In addition, quencher anions that have the function of deexciting (quenching) active molecules in the excited state, and ferrocenes having an anionic group such as a carboxyl group, phosphonic acid group, or sulfonic acid group on the cyclopentadienyl ring. Metallocene compound anions such as luteocene can also be used as necessary.
Also, p is selected so that the charge is neutral throughout the molecule.

Examples of the quencher anion include, for example, JP-A-60-234892, JP-A-5-43814, JP-A-5-305770, JP-A-6-239028, JP-A-9-309886. JP, 9-323478, JP 10-45767, JP 11-208118, JP 2000-168237, JP 2002-201373, JP 2002-206061, Examples include anions described in JP-A-2005-297407, JP-B-7-96334, WO98 / 29257, and the like.

Examples of the anion represented by An ^q- in the general formula (I) include a monovalent organic sulfonic acid anion, bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4- Ethylcyclohexanesulfonate ion, benzenedisulfonate ion, and naphthalenedisulfonate ion are preferable from the viewpoint of heat resistance, and bistrifluoromethylsulfonylimide ion is more preferable.

Among the compounds represented by the general formula (I), the following compounds are preferable because the waveform controllability is particularly excellent in the light absorption spectrum.
That is, either one or both of R ⁴ and R ⁷ are a hydroxyl group, a halogen atom, an alkyl group having 1 to 8 carbon atoms substituted with a halogen atom, or a carbon atom number 1 to 1 optionally substituted with a halogen atom. An alkoxy group of 8 is preferable, a halogen atom, an alkyl group having 1 to 8 carbon atoms substituted with a halogen atom is more preferable, and a halogen atom is still more preferable.

R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ are groups other than hydrogen atoms, from the viewpoint of solvent solubility, the number of carbon atoms substituted or unsubstituted with polar groups, particularly hydroxyl groups. 1-8 alkyl groups are preferred.

X is preferably an oxygen atom or a sulfur atom from the viewpoint of availability.

Specific examples of the cation moiety of the compound represented by the general formula (I) of the present invention include the following compound No. 1-No. 36.

Although the manufacturing method of the compound represented with the said general formula (I) is not specifically limited, For example, when X in the said general formula (I) is an oxygen atom, it can manufacture according to following Reaction Formula.
In addition, also when X is other than an oxygen atom, it can manufacture according to the following manufacturing method. It can also be produced according to a known method described in Journal of Organic Chemistry (2009), 74 (8), 3183-3185.

(Wherein R ¹ to R ¹⁶ , An ^q− , p and q are the same as those in the general formula (I)).

The compound represented by the general formula (I) is used as a colored alkali-developable photosensitive composition described below, as well as an optical filter used for a display or an optical lens, a silver salt photographic photosensitive material, a dyed material, and a paint. Used for optical recording dyes and the like.

Next, the colored photosensitive composition of the present invention will be described. In the following description, a colored photosensitive composition or a colored alkali-developable composition described later is appropriately described as a colored composition.

The colored photosensitive composition of the present invention comprises a dye (A) containing the compound of the present invention (hereinafter also referred to as dye (A)), a polymerizable compound (B) having an ethylenically unsaturated bond (providing alkali developability). A polymerizable compound (B ′) having an ethylenically unsaturated bond having an alkali-soluble substituent, and a photopolymerization initiator (C), and further, if necessary, a coloring material (provided that the general formula (I 1 type or more (D) except the dye which consists of a compound represented by this.

The dye (A) used in the present invention only needs to contain at least one compound of the present invention, and can be used alone or in combination. In addition to the compound of the present invention, a known dye can be used as the dye (A). Known dyes include, for example, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes, stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes. , Phthalocyanine dyes, cyanine dyes, and the like. These may be used in combination.

In the dye (A) used in the present invention, the content of the compound of the present invention is preferably 50 to 100% by mass, more preferably 70 to 100% by mass. When content of the compound of this invention is smaller than 50 mass%, the solubility to a solvent may fall or heat resistance may fall.

In the colored composition of the present invention, the content of the dye (A) in the colored composition of the present invention is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass. If the content of the dye (A) is less than 0.01% by mass, a color having a desired concentration may not be obtained in the cured product of the colored composition of the present invention. In some cases, precipitation of the dye (A) may occur.

<Polymerizable compound (B) having an ethylenically unsaturated bond>
The polymerizable compound (B) having an ethylenically unsaturated bond is not particularly limited, and those conventionally used in photosensitive compositions can be used. For example, ethylene, propylene, butylene, isobutylene can be used. , Vinyl chloride, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene, and other unsaturated aliphatic hydrocarbons; (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, highmic acid, Crotonic acid, isocrotonic acid, vinyl acetate, allyl acetate, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl] , Ω-carboxypolycaprolactone mono (meth) acrylate, etc. Mono (meth) acrylate, hydroxyethyl (meth) acrylate malate, hydroxypropyl (meth) acrylate malate, dicyclopentadiene malate or one carboxyl group and two or more (meth) acryloyl groups Unsaturated polybasic acids such as polyfunctional (meth) acrylates; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate; A1-No. A4, methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (meth) acrylate, (meta ) Ethylhexyl acrylate, (meth) acrylic acid Phenoxyethyl, tetrahydrofuryl (meth) acrylate, vinyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol Di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, trimethylolethanetri (Meth) acrylate, trimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol Unsaturated monobasic acids such as tra (meth) acrylate, pentaerythritol tri (meth) acrylate, tricyclodecane dimethylol di (meth) acrylate, tri [(meth) acryloylethyl] isocyanurate, polyester (meth) acrylate oligomers and the like Esters of polyhydric alcohols or polyphenols; metal salts of unsaturated polybasic acids such as zinc (meth) acrylate and magnesium (meth) acrylate; maleic anhydride, itaconic anhydride, citraconic anhydride, methyl Tetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyltetrahydro Phthalic anhydride-anhydrous Acid anhydrides of unsaturated polybasic acids such as rain acid adducts, dodecenyl succinic anhydride, methyl hymic anhydride; (meth) acrylamide, methylene bis- (meth) acrylamide, diethylenetriamine tris (meth) acrylamide, xylylene bis (meth) Unsaturated monobasic acids such as acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide and amides of polyvalent amines; unsaturated aldehydes such as acrolein; (meth) acrylonitrile, α-chloroacrylonitrile, cyanide Unsaturated nitriles such as vinylidene and allyl cyanide; styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinyl Unsaturated aromatic compounds such as ruphenol, vinyl sulfonic acid, 4-vinyl benzene sulfonic acid, vinyl benzyl methyl ether, vinyl benzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; vinyl amine, allyl amine, N-vinyl pyrrolidone, vinyl Unsaturated amine compounds such as piperidine; vinyl alcohols such as allyl alcohol and crotyl alcohol; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, allyl glycidyl ether; maleimide, N-phenylmaleimide, N -Unsaturated imides such as cyclohexylmaleimide; Indenes such as indene and 1-methylindene; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene Macromolecules having a mono (meth) acryloyl group at the end of the polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, polysiloxane, etc .; vinyl chloride, vinylidene chloride, divinyls Cuccinate, diallyl phthalate, triallyl phosphate, triallyl isocyanurate, vinyl thioether, vinyl imidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl group-containing vinyl monomers and vinyl isocyanate compounds of polyisocyanate compounds, hydroxyl groups -Containing vinyl monomers and polyepoxy compounds such as vinyl epoxy compounds, pentaerythritol triacrylate and dipentaerythritol pentaacrylate Reaction products of polyfunctional isocyanates such as relate and tolylene diisocyanate and hexamethylene diisocyanate, hydroxyl-containing polyfunctional acrylates such as pentaerythritol triacrylate and dipentaerythritol pentaacrylate, succinic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, etc. The polyfunctional acrylate which has an acid value which is a reaction product of a dibasic acid anhydride is mentioned.
These polymerizable compounds can be used alone or in admixture of two or more, and when used in admixture of two or more, they are copolymerized in advance and used as a copolymer. May be.

In the colored composition of the present invention, as the polymerizable compound (B) having an ethylenically unsaturated bond, a polymerizable compound (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that imparts alkali developability. When ') (hereinafter also referred to as an alkali-developable compound (B') having an ethylenically unsaturated bond) is used, the colored photosensitive composition of the present invention becomes a colored alkaline-developable photosensitive composition. Examples of the alkali-developable compound (B ′) having an ethylenically unsaturated bond include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, Butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-ethylhexyl ( (Meth) acrylates such as (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate; N-vinylpyrrolidone; styrene and its Conductors, styrenes such as α-methylstyrene; acrylamides such as (meth) acrylamide, methylol (meth) acrylamide, alkoxymethylol (meth) acrylamide, diacetone (meth) acrylamide; (meth) acrylonitrile, ethylene, propylene, butylene, Other vinyl compounds such as vinyl chloride and vinyl acetate, and macromonomers such as polymethyl methacrylate macromonomer and polystyrene macromonomer, monomethacrylate of tricyclodecane skeleton, N-phenylmaleimide, methacryloyloxymethyl-3-ethyloxetane, etc. And a copolymer of (meth) acrylic acid, and an isocyanate compound having an unsaturated bond such as Karenz MOI and AOI manufactured by Showa Denko K.K. Copolymers of silyl acids, novolac epoxy compounds such as phenol and / or cresol novolac epoxy resins, novolak epoxy resins having a biphenyl skeleton and a naphthalene skeleton, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds, etc. A polyphenylmethane type epoxy resin having a functional epoxy group, obtained by allowing an unsaturated monobasic acid to act on an epoxy group such as an epoxy compound represented by the following general formula (II), and further reacting with a polybasic acid anhydride Resins can be used. These monomers can be used individually by 1 type or in mixture of 2 or more types. The alkali developable compound (B ′) having an ethylenically unsaturated bond preferably contains 0.2 to 1.0 equivalent of an unsaturated group.

Wherein X ¹ is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, —O—, —S—, —SO ₂ —, —SS—, —SO—, —CO—, —OCO—, or a substituent represented by the following formula (A), (B) or (C), wherein the alkylidene group may be substituted with a halogen atom R ³¹ , R ³² , R ³³ and R ³⁴ are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl having 2 to 5 carbon atoms. Represents a group or a halogen atom, and the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom, and m is an integer of 0 to 10.)

(In the formula, Y ² represents a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or 1 carbon atom) Represents a cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkoxy group having 10 to 10 carbon atoms, or a hydrogen atom, and Y ¹ represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms. Group, an alkenyl group having 2 to 10 carbon atoms or a halogen atom, the alkyl group, alkoxy group and alkenyl group in Y ¹ may be substituted with a halogen atom, and b is an integer of 0 to 5. )

Wherein Y ³ and Y ⁴ are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or an aryl having 6 to 20 carbon atoms which may be substituted with a halogen atom. Group, an aryloxy group having 6 to 20 carbon atoms which may be substituted with a halogen atom, an arylthio group having 6 to 20 carbon atoms which may be substituted with a halogen atom, or the number of carbon atoms which may be substituted with a halogen atom An arylalkenyl group having 8 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms which may be substituted with a halogen atom, a heterocyclic group having 2 to 20 carbon atoms which may be substituted with a halogen atom, and these groups; multiple combined group, or a halogen atom, a methylene group in the alkyl group and arylalkyl group in the Y ³ and Y ⁴ are interrupted by an unsaturated bond, -O- or -S- May have, Y ⁴ may form a ring with the adjacent Y ⁴ each other, n represents an integer of 0 to 4, q represents an integer of 0 ~ 8, r is an integer of from 0 to 4 S represents an integer of 0 to 4, and the total number of r and s is an integer of 2 to 4.)

Examples of the unsaturated monobasic acid that acts on the epoxy group of the epoxy compound include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate / malate, and the like. Examples thereof include hydroxyethyl acrylate / malate, hydroxypropyl methacrylate / malate, hydroxypropyl acrylate / malate, and dicyclopentadiene / malate.

In addition, the polybasic acid anhydride to be acted after the unsaturated monobasic acid is allowed to act is biphenyltetracarboxylic dianhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride , Pyromellitic anhydride, 2,2'-3,3'-benzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, hexahydro phthalic anhydride, methyl tetrahydro phthalic anhydride Acid, nadic anhydride, methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2- Dicarboxylic acid anhydride, trialkyltetrahydrophthalic anhydride - maleic anhydride adduct, dodecenyl succinic anhydride, and anhydride and methyl high Mick acid.

The reaction molar ratio of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride is preferably as follows. That is, in an epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monobasic acid are added to one epoxy group of the epoxy compound, the hydroxyl group 1 of the epoxy adduct is It is preferable that the ratio of the acid anhydride structure of the polybasic acid anhydride is 0.1 to 1.0.

The reaction of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride can be performed according to a conventional method.

In order to improve the developability of the colored alkali-developable photosensitive composition of the present invention by adjusting the acid value, a monofunctional or polyfunctional epoxy compound may be used together with the alkali-developable compound having an ethylenically unsaturated bond. it can. The alkali-developable compound having an ethylenically unsaturated bond preferably has a solid content acid value in the range of 5 to 120 mgKOH / g, and the use amount of the monofunctional or polyfunctional epoxy compound satisfies the acid value. It is preferable to select as follows.

Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, 2-ethylhexyl glycidyl ether, Allyl glycidyl A , Propargyl glycidyl ether, p-methoxyethyl glycidyl ether, phenyl glycidyl ether, p-methoxy glycidyl ether, p-butylphenol glycidyl ether, cresyl glycidyl ether, 2-methyl cresyl glycidyl ether, 4-nonylphenyl glycidyl ether, benzyl Glycidyl ether, p-cumylphenyl glycidyl ether, trityl glycidyl ether, 2,3-epoxypropyl methacrylate, epoxidized soybean oil, epoxidized linseed oil, glycidyl butyrate, vinylcyclohexane monooxide, 1,2-epoxy-4- Vinylcyclohexane, styrene oxide, pinene oxide, methylstyrene oxide, cyclohexene oxide, propylene oxide, compound No.A2, No. A3 etc. are mentioned.

As the polyfunctional epoxy compound, it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers because a colored alkali-developable photosensitive composition with better characteristics can be obtained. As the bisphenol type epoxy compound, an epoxy compound represented by the above general formula (I) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used. Examples of the glycidyl ethers include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (glycidyloxymethyl) methane, 1,1,1,1- tetra (glycidyloxymethyl) include methane.

Other novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as phthalic acid diglycidyl ester, tetrahydrophthalic acid diglycidyl ester, dimer acid glycidyl ester; Glycidylamines such as diphenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; heterocyclic epoxy compounds such as 1,3-diglycidyl-5,5-dimethylhydantoin and triglycidyl isocyanurate; Dioxide compounds such as pentadiene dioxide; naphthalene type epoxy compounds, triphenylmethane type epoxy compounds, dicyclopentadiene type epoxy compounds and the like can also be used.

Among the polymerizable compounds (B) having an ethylenically unsaturated bond (including the alkali developable compound (B ′) having the ethylenically unsaturated bond), from the viewpoint of compatibility, alkali developability and heat resistance, Unsaturated aliphatic hydrocarbons such as ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene chloride, vinylidene fluoride, tetrafluoroethylene; (meth) acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid , Fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinyl acetic acid, allylic acetic acid, cinnamic acid, sorbic acid or mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- ( (Meth) acryloyloxyethyl] or ω-carboxypolycaprolactone mono (meth) acrylate Mono (meth) acrylate of a polymer having a carboxy group and a hydroxyl group at both ends, such as a salt, hydroxyethyl (meth) acrylate malate, hydroxypropyl (meth) acrylate malate, dicyclopentadiene malate and one Unsaturated monobasic acid such as polyfunctional (meth) acrylate having a carboxyl group and two or more (meth) acryloyl groups; unsaturated monobasic to epoxy group such as epoxy compound represented by the above general formula (III) Polyfunctional acrylates having acid values such as resins obtained by reacting acids and further polybasic acid anhydrides; methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth ) Acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, -Butyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxy (Meth) acrylic esters such as ethyl (meth) acrylate and tetrahydrofurfuryl (meth) acrylate are preferred, and unsaturated aliphatic hydrocarbons and unsaturated monobasic acids are more preferred.

In the colored composition of the present invention, the content of the polymerizable compound (B) having the ethylenically unsaturated bond (including the alkali developable compound (B ′) having the ethylenically unsaturated bond) is the content of the present invention. In the coloring composition, 30 to 99% by mass, particularly 60 to 95% by mass is preferable. If the content of the polymerizable compound (B) having an ethylenically unsaturated bond is less than 30% by mass, the mechanical strength of the cured product is insufficient and cracks occur, or if it has alkali developability, development failure occurs. If it is larger than 99% by mass, curing due to exposure becomes insufficient and tackiness occurs, and if it has alkali developability, the development time becomes long and the cured part may be damaged by alkali. There is a case.

<Photopolymerization initiator (C)>
As the photopolymerization initiator (C), conventionally known compounds can be used. For example, benzophenone, phenylbiphenyl ketone, 1-hydroxy-1-benzoylcyclohexane, benzoin, benzyldimethyl ketal, 1-benzyl- 1-dimethylamino-1- (4′-morpholinobenzoyl) propane, 2-morpholyl-2- (4′-methylmercapto) benzoylpropane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diethylthioxanthone, ethyl Anthraquinone, 4-benzoyl-4'-methyldiphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2- (4'-isopropyl) benzoylpropane, 4-butyl Benzoyltrichloromethane, 4-phenoxybenzoyldichloromethane, methyl benzoylformate, 1,7-bis (9'-acridinyl) heptane, 9-n-butyl-3,6-bis (2'-morpholinoisobutyroyl) carbazole, 2 -Methyl-4,6-bis (trichloromethyl) -s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2-naphthyl-4,6-bis (trichloromethyl) -s -Triazine, 2,2-bis (2-chlorophenyl) -4,5,4 ', 5'-tetraphenyl-1-2'-biimidazole, 4,4-azobisisobutyronitrile, triphenylphosphine, Examples include camphorquinone and benzoyl peroxide. Commercially available products include N-1414, N-1717, N-1919, and PZ-4. 8, (manufactured by (Corporation) ADEKA Corporation) NCI-831, NCI-930, IRGACURE369, IRGACURE907, IRGACURE OXE 01, IRGACURE OXE 02 (BASF (Co.) Co., Ltd.).

Among the photopolymerization initiators (C), from the viewpoint of sensitivity and color tone, 2-morpholylu 2- (4′-methylmercapto) benzoylpropane, 9-n-butyl-3,6-bis (2′-morpholinoisopetite). Royl) carbazole is preferred, and 2-morpholylu 2- (4′-methylmercapto) benzoylpropane is more preferred.

In the colored composition of the present invention, the content of the photopolymerization initiator (C) is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass in the colored composition of the present invention. When the content of the photopolymerization initiator (C) is less than 0.1% by mass, curing by exposure may be insufficient. When the content is more than 30% by mass, the initiator (C) is contained in the resin composition. May precipitate.

The coloring composition of the present invention may further contain a color material (D) other than the compound of the present invention. These color materials can be used alone or in admixture of two or more.

Examples of the color material (D) include nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindoline compounds, quinacridone compounds, Antanthrone compound, perinone compound, perylene compound, diketopyrrolopyrrole compound, thioindigo compound, dioxazine compound, triphenylmethane compound, quinophthalone compound, naphthalene tetracarboxylic acid; azo dye, metal complex compound of cyanine dye; lake pigment; furnace method, Carbon black obtained by channel method or thermal method, or carbon black such as acetylene black, ketjen black or lamp black; A product prepared and coated with an epoxy resin, a carbon black previously dispersed with a resin in a solvent, adsorbed with 20 to 200 mg / g of resin, and a carbon black treated with an acidic or alkaline surface The average particle size is 8 nm or more, the DBP oil absorption is 90 ml / 100 g or less, and the total oxygen amount calculated from CO and CO ₂ in the volatile content at 950 ° C. is 9 mg or more per 100 m ² of the surface area of carbon black. Graphite, graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; hydrophobic resin, chromium oxide green, miloli blue, cobalt green , Cobalt blue, manganese series, Fe Cyanide, phosphate ultramarine, bitumen, ultramarine, cerulean blue, pyridian, emerald green, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, synthetic iron black, amber, etc. Inorganic pigments or organic pigments can be used.

As the coloring material (D), commercially available pigments can also be used. For example, Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 9 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168 175, 180, 185; Pigment Green 7, 10, 36; Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 22, 24, 56 , 60, 61, 62, 64; pigment violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50, and the like.

As the coloring material (D), a known dye can be used. Known dyes include, for example, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, Examples thereof include phthalocyanine dyes and cyanine dyes.

In the colored composition of the present invention, the content of the coloring material (D) is preferably 0 to 350 parts by mass, more preferably 100 parts by mass of the polymerizable compound (B) having an ethylenically unsaturated bond. Is 0 to 250 parts by mass. When it exceeds 350 parts by mass, the light transmittance of the colored composition of the present invention, particularly the cured product using the colored alkali-developable photosensitive composition, and the color filter for display device is lowered, and the luminance of the display device is lowered. Therefore, it is not preferable.

A solvent can be further added to the colored composition of the present invention. The solvent is usually a solvent capable of dissolving or dispersing each of the above components (the dye (A) containing the compound of the present invention, etc.) as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl Ketones such as isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; ether solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether; acetic acid Ester solvents such as methyl, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, texanol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether Cellosolve solvents such as methanol; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl Ether ester solvents such as ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate and ethoxyethyl propionate; BTX solvents such as benzene, toluene and xylene; hexane, heptane and octane Aliphatic hydrocarbon solvents such as cyclohexane, terpene hydrocarbon oils such as turpentine oil, D-limonene and pinene; mineral spirits, swazol # 310 (Cosmo Matsuyama Oil ( )), Paraffinic solvents such as Solvesso # 100 (Exxon Chemical Co., Ltd.); halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, 1,2-dichloroethane; halogens such as chlorobenzene Aromatic hydrocarbon solvents; carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, water These solvents can be used as one or a mixture of two or more. Among these, ketones, ether ester solvents, etc., particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like have good compatibility between the resist and the photopolymerization initiator (C) in the colored composition. preferable.

In the colored composition of the present invention, the amount of the solvent used is such that the concentration of the composition other than the solvent is preferably 5 to 30% by mass, and if it is less than 5% by mass, it is difficult to increase the film thickness. Yes, it is not preferable because it cannot absorb light of a desired wavelength sufficiently, and when it is larger than 30% by mass, the storage stability of the composition due to the precipitation of the composition may be reduced, or the handling may be reduced because the viscosity is improved. There is.

The coloring composition of the present invention can further contain an inorganic compound. Examples of the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Among these, titanium oxide, silica, layered clay mineral, silver and the like are preferable. In the colored composition of the present invention, the content of the inorganic compound is preferably 0.1 to 50 parts by mass, more preferably 0, relative to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond. These inorganic compounds can be used alone or in combination of two or more.
These inorganic compounds are used, for example, as fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellents, and the like.

In the coloring composition of the present invention, when a pigment and / or an inorganic compound is used, a dispersant can be added. As the dispersant, any colorant or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used, and polyester having a basic functional group, Polymer dispersant made of polyether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Those are preferably used.

In addition, the coloring composition of the present invention includes, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; plasticizer; adhesion promoter; filler; Conventional additives such as an agent, a leveling agent, a surface conditioner, an antioxidant, an ultraviolet absorber, a dispersion aid, a coagulation inhibitor, a catalyst, an effect accelerator, a cross-linking agent, and a thickener can be added.

In the colored composition of the present invention, optional components other than the dye (A), the polymerizable compound (B) having the ethylenically unsaturated bond, and the photopolymerization initiator (C) (however, the colorant (D) and The content of the solvent (excluding the solvent) is appropriately selected according to the purpose of use and is not particularly limited, but is preferably a total with respect to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond. And 50 parts by mass or less.

The colored composition of the present invention improves the properties of the cured product comprising the colored composition of the present invention by using another organic polymer together with the polymerizable compound (B) having the ethylenically unsaturated bond. You can also Examples of the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate. Copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Polyester, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like. Among these, polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included. Masui.
When another organic polymer is used, the amount used is preferably 10 to 500 parts by mass with respect to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond.

Furthermore, a chain transfer agent, a sensitizer, a surfactant, a silane coupling agent, a melamine compound, and the like can be used in combination with the colored composition of the present invention.
As the chain transfer agent or sensitizer, a sulfur atom-containing compound is generally used. For example, thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine, 2-mercaptonicotinic acid, 3- [N- ( 2-mercaptoethyl) carbamoyl] propionic acid, 3- [N- (2-mercaptoethyl) amino] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, mercaptophenol , 2-me Captoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3- Mercapto compounds such as mercaptopropionate), disulfide compounds obtained by oxidizing the mercapto compound, iodoacetates such as iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid, etc. Alkyl compounds, trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol compounds such as trimercaptopropionic acid tris (2-hydroxyethyl) isocyanurate, Karenz MT BD1, PE1, NR1 manufactured by Showa Denko KK and the like.

Examples of the surfactant include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.

As the silane coupling agent, for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, an isocyanate group, a methacryloyl group, or an epoxy group, such as KBE-9007, KBM-502, and KBE-403, can be used. A silane coupling agent is preferably used.

Examples of the melamine compound include all or part of active methylol groups (CH ₂ OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified. Here, examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other. Moreover, the methylol group which is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules, and as a result, an oligomer component may be formed. Specifically, hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used. Among these, alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.

The coloring composition of the present invention is a known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc. It can be applied on the supporting substrate. Further, once applied on a supporting substrate such as a film, it can be transferred onto another supporting substrate, and the application method is not limited.

In addition, as the active light source used for curing the colored composition of the present invention, one that emits light having a wavelength of 300 to 450 nm can be used, for example, ultrahigh pressure mercury, mercury vapor arc, carbon arc. And xenon arc.

Furthermore, by using laser light as the exposure light source, the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy. As the laser beam, light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs light in the visible to infrared region is added.

The colored composition of the present invention (or a cured product thereof) is a liquid crystal display panel for color display such as a photocurable paint or varnish, a photocurable adhesive, a printed board or a color TV, a PC monitor, a portable information terminal, a digital camera, etc. Color filters, color filters for CCD image sensors, electrode materials for plasma display panels, powder coatings, printing inks, printing plates, adhesives, dental compositions, resin for stereolithography, gel coats, photoresists for electronics, Electroplating resist, etching resist, both liquid and dry film, solder resist, forming a structure in the manufacturing process of plasma display panel, electroluminescent display device, and LCD for manufacturing color filters for various display applications Composition for encapsulating resist, electrical and electronic components for -Resist, magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etching masks, color test systems, glass fiber cable coatings, stencils for screen printing, materials for producing 3D objects by stereolithography Holographic recording material, image recording material, fine electronic circuit, decoloring material, decoloring material for image recording material, decoloring material for image recording material using microcapsules, photoresist material for printed wiring board, UV and visible It can be used for various applications such as a photoresist material for a laser direct image system, a photoresist material used for forming a dielectric layer in the sequential lamination of printed circuit boards, or a protective film, and the application is not particularly limited.

The colored composition of the present invention, in particular the colored alkali-developable photosensitive composition, is used for the purpose of forming a pixel of a color filter, and in particular a color filter for a display device for an image display device such as a liquid crystal display panel or an organic EL. It is useful as a photosensitive composition for forming.

The color filter for display device of the present invention may have red, green, blue, orange, purple and black optical elements in addition to the cured product of the present invention.

The color filter for display device includes (1) a step of forming a coating film of the colored composition of the present invention (particularly a colored alkali-developable photosensitive composition) on a substrate, and (2) a predetermined pattern shape on the coating film. Preferably formed by a step of irradiating actinic light through a mask having, (3) a step of developing a film after exposure with a developer (particularly an alkali developer), and (4) a step of heating the film after development. Is done. The colored composition of the present invention is also useful as a colored composition for an ink jet system or a transfer system without a development step.

A color filter used in a liquid crystal display panel or the like is manufactured by repeating the above steps (1) to (4) using a coloring composition of the present invention or other combination and combining patterns of two or more colors. Can do.

Hereinafter, the present invention will be specifically described by way of examples and comparative examples.

Example 1. Compound No. 13, no. 25, no. 26 and no. Synthesis of 35 <Step 1>
0.01 mol of the following compound S-1, 0.02 mol of monoethylaminophenol and 0.03 mol of sulfuric acid were mixed and stirred at 140 ° C. for 8 hours. The reaction solution was added dropwise to an aqueous sodium hydroxide solution, the organic matter was extracted with toluene, washed three times with water, and then the solvent was distilled off from the organic layer. The residue was purified by silica gel column chromatography (developing solvent: chloroform) to obtain 0.005 mol of a leuco body (yield 52%).

<Step 2>
After charging and stirring 2.56 g (0.005 mol) of the leuco body obtained in Step 1, 19.75 g of water and 3.95 g of hydrochloric acid, 9.27 g of 35 mass% iron chloride aqueous solution was charged and stirred at 80 ° C. for 8 hours. . After cooling to room temperature, chloroform was added, the aqueous layer was taken out and washed with water, and then neutralized with an aqueous sodium hydrogen carbonate solution. 4.79 g (0.01 mol) of bis (trifluoromethanesulfonyl) imide potassium was added to perform salt exchange, and then the solvent was distilled off from the obtained organic layer. The residue was purified by silica gel column chromatography (developing solvent: chloroform: ethyl acetate = 8: 2) to obtain 1.5 g (yield 38%) of the desired product.
Using a method similar to the synthesis method described above, Compound No. 25, no. 26 and no. 35 was synthesized. Each compound was analyzed and confirmed to be the target compound. The analysis results are shown in [Table 1], [Table 2], [FIG. 1], [FIG. 2], [FIG. 3] and [FIG. 4].

Example 2 and Comparative Example 2 Preparation of colored alkali-developable photosensitive composition <Step 1> Preparation of alkali-developable photosensitive composition (B) 30.33 g of ACA Z251 (manufactured by Daicel Cytec Co., Ltd.) and Aronix M-450 (manufactured by Toagosei Co., Ltd.) 11.04 g, 1.93 g of Irgacure 907 (manufactured by BASF) as the component (C), 20.08 g of PGMEA as the component (E), and FZ2122 (manufactured by Dow Corning Toray) as the other components. 01 g was mixed and stirred until insoluble matter disappeared to obtain an alkali-developable photosensitive composition.

<Step 2> Preparation of dye solution As the component (A), 0.10 g of the compound described in [Table 3] and 1.90 g of PGMEA were added respectively, and the mixture was stirred to dissolve. 1-No. 2 and comparative dye solution No. 1-No. 2.

<Step 3> Preparation of colored alkali-developable photosensitive composition 5.0 g of the alkali-developable photosensitive composition obtained in Step 1 is mixed with 1.0 g of the dye solution obtained in Step 2 and the comparative dye solution. And stirring until uniform, the colored alkali-developable photosensitive composition No. 1-No. 2 and comparative colored alkali-developable photosensitive composition No. 2 1-No. 2 was obtained.

Example 3 and Comparative Example 3 Evaluation of heat resistance by firing The colored alkali-developable photosensitive composition No. obtained in Example 2 was used. 1 and no. 2 and comparative colored alkali-developable photosensitive composition No. 2 obtained in Comparative Example 2. 1 and no. Each of 2 was coated on a glass substrate under conditions of 410 rpm × 7 seconds and dried on a hot plate (90 ° C., 90 seconds). The obtained coating film was exposed (150 mJ / cm ² ) with an ultrahigh pressure mercury lamp. The coated film after exposure was baked under conditions of 230 ° C. × 30 min. The color difference (ΔE _ab ^* ) before and after firing was examined. The better the heat resistance, the higher the color difference value. The results are shown in [Table 4].

Example 4 and Comparative Example 4 Waveform controllability of light absorption spectrum Compound No. 13, Compound No. 26, Compound No. 35, Comparative Compound No. 1 and comparative compound no. The light absorption spectrum of 2 was measured. The measurement solvent and the equipment used are as follows.
Measurement solvent: Chloroform dilution ratio: 1 mol / L
Equipment used: Hitachi spectrophotometer U-3010
The full width at half maximum of the spectrum waveform obtained from each compound was measured. The full width at half maximum is the absolute value of the difference in wavelength between the long wavelength side and the short wavelength side where the absorbance at λmax is 1, and the absorbance is 0.5. The smaller the half width, the steeper the waveform, and the better the dye for the alkali-developable photosensitive composition. The results are shown in [Table 5].

Claims

The compound represented by the following general formula (1).

(Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 each independently represents a hydrogen atom or a halogen atom,
A cyano group, a nitro group, a hydroxyl group, or an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms with a halogen atom,
An alkoxy group having 1 to 8 carbon atoms substituted or unsubstituted by a halogen atom,
An aryl group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
An aryloxy group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
An arylthio group having 6 to 20 carbon atoms substituted or unsubstituted by a halogen atom,
A substituted or unsubstituted arylalkenyl group having 8 to 20 carbon atoms, or a substituted or unsubstituted arylalkyl group having 7 to 20 carbon atoms, which is substituted with a halogen atom,
R 11 , R 12 , R 13 , R 14 , R 15 and R 16 each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group or a nitro group,
Substituted with nitro group, carboxyl group, sulfonic acid group, hydroxyl group or halogen atom, substituted with carboxyl ester, sulfonic acid group ester, carboxyl salt or sulfonic acid salt, or unsubstituted An alkyl group having 1 to 8 carbon atoms,
Substituted with alkyl group having 1 to 4 carbon atoms, halogen atom, cyano group, vinyl group, nitro group, carboxyl group, sulfonic acid group or hydroxyl group, ester of carboxyl group, ester of sulfonic acid group, carboxyl group A phenyl group which is substituted or unsubstituted with a salt or a salt of a sulfonic acid group,
Substituted with alkyl group having 1 to 4 carbon atoms, halogen atom, cyano group, vinyl group, nitro group, carboxyl group, sulfonic acid group or hydroxyl group, ester of carboxyl group, ester of sulfonic acid group, carboxyl group It represents an unsubstituted benzyl group that is substituted with a salt or a salt of a sulfonic acid group.
R 1 and R 11 , R 2 and R 12 , R 5 and R 13 , R 6 and R 14 , R 9 and R 15, and R 10 and R 16 may be linked to form a 6-membered ring. ,
R 11 and R 12 , R 13 and R 14 , and R 15 and R 16 may be linked to form a 3- to 6-membered heterocyclic ring,
R 3 and R 4 and R 7 and R 8 are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR 17 R 18 , CO, NR 19 , PR 20 or SO 2 to form a ring. You may,
X represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, CR 17 R 18 , CO, NR 19 , PR 20 or SO 2 ;
R 17 , R 18 , R 19 and R 20 are each independently a halogen atom-substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, or a halogen atom-substituted or unsubstituted carbon. Represents an alkoxy group having 1 to 8 atoms,
An q− represents a q-valent anion, q represents 1 or 2, and p represents a coefficient for keeping the charge neutral.
However, any one or more of R 11 , R 12 , R 13 , R 14 , R 15 and R 16 is a hydrogen atom. )
In the general formula (I), either one or both of R 4 and R 7 may be substituted with a hydroxyl group, a halogen atom, an alkyl group having 1 to 8 carbon atoms substituted with a halogen atom, or a halogen atom. The compound according to claim 1, which is a good alkoxy group having 1 to 8 carbon atoms.
A colored photosensitive composition containing a dye (A) containing the compound according to claim 1 or 2, a polymerizable compound (B) having an ethylenically unsaturated bond, and a photopolymerization initiator (C).
Furthermore, the coloring photosensitive composition of Claim 3 which contains 1 or more types (D) of coloring materials (however, except the compound represented by the said general formula (I)).
A cured product of the colored photosensitive composition according to claim 3 or 4.
A color filter for display device comprising at least a part of the cured product according to claim 5.