KR102389352B1 - Colored resin composition, colored filter and display device - Google Patents

Abstract

The present invention provides a colored resin composition capable of forming a color filter and a display device having excellent contrast and light resistance.
The colored resin composition according to the present invention is characterized in that it contains a colorant and a resin, and the colorant contains an anion derived from a methine dye having an acid group and a salt of a divalent or higher metal cation. Further, the colored resin composition according to the present invention contains a colorant and a resin, and the colorant is characterized in that the colorant contains an anion derived from a cyanine compound having an acid group and a salt of a divalent or higher metal cation.

Description

A colored resin composition, a color filter, and a display device TECHNICAL FIELD

The present invention relates to a colored resin composition, a color filter, and a display device.

A color filter used for a display device such as a liquid crystal display device, an electroluminescent display device, and a plasma display, or a solid-state imaging device such as a CCD or CMOS sensor, is manufactured from a colored resin composition. The composition containing the compound represented by (3) is known (patent document 1).

Moreover, as a coloring agent for colored resin compositions, the compound represented by Formula (2-1) is also known.

(Patent Document 1) Japanese Patent Application Laid-Open No. 2009-235392

However, conventionally known color filters formed from the above colored resin compositions may not sufficiently satisfy contrast and light resistance in some cases. The present invention provides a colored resin composition capable of forming a color filter having excellent contrast and light resistance. do.

The present invention includes the following inventions.

[1] A colored resin composition containing a coloring agent and a resin, wherein the coloring agent contains an anion derived from a methine dye having an acid group and a salt of a divalent or higher metal cation.

[2] A colored resin composition containing a coloring agent and a resin, wherein the coloring agent contains an anion derived from a cyanine compound having an acid group and a salt of a divalent or higher metal cation.

[3] The colored resin composition according to [1] or [2], wherein the salt is a compound represented by formula (I).

[in formula (I),

Ring T ¹ represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms having a substituent containing at least a -N(R ^a1 )(R ^a2 ) group, or an aromatic heterocyclic ring which may have a substituent.

Ring T2 represents the nitrogen ^- containing aromatic heterocyclic ring which contains N or N< ⁺ > in the structural atom of the ring which may have a substituent.

L ¹ and L ² each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms which may have a substituent.

k represents an integer of 0 or more and 4 or less.

M ⁿ⁺ represents an n-valent metal cation.

n represents an integer of 2 or more and 5 or less.

r represents the number of M ⁿ⁺ and is selected so that the valence of formula (I) becomes 0.

R ^a1 and R ^a2 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms.]

[4] The colored resin composition according to [3], wherein the ring T ² represents a nitrogen-containing aromatic heterocycle containing N ⁺ in a constituent atom of the ring which may have a substituent, and r is 1.

[5] The colored resin composition according to any one of [1] to [4], further comprising a polymerizable compound and a polymerization initiator.

[6] A color filter formed from the colored resin composition according to any one of [1] to [5].

[7] A display device comprising the color filter according to [6].

ADVANTAGE OF THE INVENTION According to this invention, the colored resin composition which can form the color filter excellent in contrast and light resistance is provided.

<Colored resin composition>

The colored resin composition of this invention contains a coloring agent (A) and resin (B), As a coloring agent (A), the salt of the anion derived from the methine dye which has an acidic radical, and a divalent or more metal cation is included.

It is preferable that the colored resin composition of this invention contains a polymeric compound (C) and a polymerization initiator (D) further.

The colored resin composition of this invention may contain the polymerization start adjuvant (D1), the solvent (E), and the leveling agent (F) further.

In this specification, the compound illustrated as each component can be used individually or in combination of multiple types, unless otherwise indicated.

<Colorant (A)>

The colored resin composition of the present invention is a salt of an anion derived from a methine dye having an acid group and a divalent or higher metal cation, preferably an anion derived from a cyanine compound having an acid group and a divalent or higher metal cation as the colorant (A) salts of

The acid group is specifically a substituent capable of ionizing hydrogen ions. The acid group is preferably a -COOH group or a -SO ₃ H group. A methine dye (preferably a cyanine compound) is Preferably 1 to 5 pieces, more preferably 1 to 3 pieces, still more preferably 1 or 2 pieces.

A methine dye is a dye which has at least 1 methine group.

A cyanine compound is a dye belonging to a polymethine dye, specifically, a nitrogen atom or C=N that can be conjugated to one or both ends of a methine group or polymethine chain, refers to a colored compound bonded to, and one nitrogen atom is + charge The structure of the cyanine compound may be any of Streptocyanines, Hemicyanines or Closed chain cyanines, preferably Hemicyanines or Closed chain cyanines.

The methine dye which has an acidic radical means the compound by which the arbitrary hydrogen atom in the molecule|numerator which comprises a methine dye was substituted by the acidic radical.

The cyanine compound which has an acidic radical means the compound by which arbitrary hydrogen atoms in the cyanine compound were substituted by the acidic radical.

In the methine dye having an acid group (preferably a cyanine compound having an acid group), hydrogen ions of the acid group are ionized to form an anion derived from the methine dye having an acid group (preferably a cyanine compound having an acid group), The anion can form a salt with a metal ^cation having a valence of divalent or higher. The salt preferably has a valence of 0, i.e., it is electrically neutral. represents an integer of 2 or more and 5 or less) is preferable.

A salt of an anion derived from the methine dye having an acid group and a metal cation having a divalent or higher, preferably a salt of an anion derived from a cyanine compound having an acid group and a metal cation having a divalent or higher, a compound represented by formula (I) (hereinafter , compound (I)) is preferred.

[in formula (I),

Ring T ¹ represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms having a substituent containing at least a -N(R ^a1 )(R ^a2 ) group, or an aromatic heterocyclic ring which may have a substituent.

Ring T2 represents the nitrogen ^- containing aromatic heterocyclic ring which contains N or N< ⁺ > in the structural atom of the ring which may have a substituent.

L ¹ and L ² each independently represent a divalent hydrocarbon group having 1 to 8 carbon atoms which may have a substituent.

k represents an integer of 0 or more and 4 or less.

M ⁿ⁺ represents an n-valent metal cation.

n represents an integer of 2 or more and 5 or less.

r represents the number of M ⁿ⁺ and is selected so that the valence of formula (I) becomes 0.

R ^a1 and R ^a2 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms.]

Examples of the aromatic hydrocarbon ring having 6 to 20 carbon atoms represented by the ring T ¹ include aromatic monocyclic hydrocarbons such as benzene, toluene, xylene, mesitylene, cumene, and cymene; pentalene, indene, naphthalene, azylene, heptalene, and biphenylene. , as-indacene, s-indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceantolylene, triphenylene, pyrene, chrysene, tetracene Condensed polycyclic hydrocarbons, such as; etc. are mentioned. The carbon number of the said aromatic hydrocarbon ring becomes like this. Preferably it is 6-16, More preferably, it is 6-10.

The aromatic hydrocarbon ring having 6 to 20 carbon atoms represented by the ring T ¹ has a substituent including at least a —N(R ^a1 )(R ^a2 ) group.

R ^a1 and R ^a2 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms. The aliphatic hydrocarbon group having 1 to 8 carbon atoms may be linear, branched or cyclic.

Examples of the linear or branched aliphatic hydrocarbon group include a linear aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group; and branched aliphatic hydrocarbon groups such as tyl group, neopentyl group and 2-ethylhexyl group. The aliphatic hydrocarbon group preferably has 1 to 6 carbon atoms, more preferably 1 to 5 carbon atoms, and further Preferably it is 1-4.

The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The carbon number of the cyclic aliphatic hydrocarbon group is , Preferably it is 3-8, More preferably, it is 3-6.

The aromatic hydrocarbon ring having 6 to 20 carbon atoms represented by the ring T ¹ is further a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, or a bromine atom; a nitro group; a cyano group; a hydroxyl group; a methoxy group, an ethoxy group, etc. An alkoxy group having 1 to 6 carbon atoms; a sulfanyl group; an alkylsulfanyl group having 1 to 6 carbon atoms such as a methylsulfanyl group and an ethylsulfanyl group; a carboxyl group; a carbamoyl group; An alkoxycarbonyl group of 6; a sulfo group; a sulfamoyl group; an alkoxysulfonyl group having 1 to 6 carbon atoms such as a methoxysulfonyl group and an ethoxysulfonyl group;

The aromatic heterocycle represented by the ring T ¹ contains at least one hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom as a component of the ring, and the ring-forming atom has a ð electron. The aromatic heterocycle is a monocyclic or ^polycyclic . Aromatic monocyclic heterocycles such as offene, pyrrole, furan, thiazole, oxazole, imidazole and pyrazole; indole, benzoindole, benzofuran, benzothiazole, benzoxazole, benzoimidazole, benzopyrazole, carbazole Condensed polycyclic heterocycles such as; hydrides such as the aromatic monocyclic heterocycle and the condensed polycyclic heterocycle; and pyridone and pyrazolone containing a carbonyl group in the ring are also included in the aromatic heterocycle. The aromatic heterocycle represented by T ¹ contains a nitrogen atom as a component of the ring, and is more preferably a nitrogen-containing aromatic heterocycle in which the nitrogen atom is >N-.

Examples of the nitrogen-containing aromatic heterocycle in the ring T ¹ include a ring represented by a formula (T ¹ -A), a formula (T ¹ -B), and a formula (T ¹ -C).

[of formula (T ¹ -A), formula (T ¹ -B), and formula (T ¹ -C),

X ^1a represents -C(R ^a3 )(R ^a4 )-, -N(R ^a5 )-, -O-, or -S-, preferably -C(R ^a3 )(R ^a4 )- .

X ^1b is -N=C(R ^a5 )-.

R ^a3 , R ^a4 and R ^a5 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent.

Ring T ⁵ represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms which may have a substituent.

ia is 1 or 2.

ib is 0, 1 or 2, preferably 0.]

The nitrogen-containing aromatic heterocycle containing N or N ⁺ as a constituent atom of the ring represented by the ring T ² includes a nitrogen atom as a constituent element of the ring, the nitrogen atom is -N< or >N ⁺ <, and the ring-forming atom is ð It is a nitrogen-containing aromatic heterocycle having an electron. A nitrogen-containing aromatic heterocycle containing N or N ⁺ as a constituent atom of the ring represented by the ring T ² is -N< or >C=N ⁺ < as a constituent element of the ring. It is more preferable to include. Examples of the nitrogen-containing aromatic heterocycle represented by the ring T ² include nitrogen-containing aromatic monocyclic heterocycles such as pyrrole, oxazole, imidazole and pyrazole; indole, benzoindole, benzoxazole, and benzimidazole. and nitrogen-containing condensed polycyclic heterocycles such as , benzopyrazole and carbazole; hydrides such as the nitrogen-containing aromatic monocyclic heterocycle and the nitrogen-containing condensed polycyclic heterocycle; and the like. Ring T ² has a substituent It is preferable to represent the nitrogen-containing aromatic heterocyclic ring which may contain N ⁺ in the structural atom of the ring which may be present.

As a nitrogen ^- containing aromatic heterocycle in ring T2, the ring etc. which are represented by a formula (T2 ^- A), a formula (T2 ^- B), and a formula (T2 ^- C) are mentioned.

[of formula (T ² -A), formula (T ² -B), and formula (T ² -C),

X ^2a represents -C(R ^a6 )(R ^a7 )-, -N(R ^a8 )-, -O-, or -S-, preferably -C(R ^a6 )(R ^a7 )- .

X ^2b is -N=C(R ^a8 )-.

R ^a6 , R ^a7 and R ^a8 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent.

Ring T ⁶ represents an aromatic hydrocarbon ring having 6 to 20 carbon atoms which may have a substituent.

ja is 0 or 1.

jb is 0, 1 or 2, preferably 0.]

The aliphatic hydrocarbon group having 1 to 8 carbon atoms represented by R ^a3 to R ^a8 may be linear, branched or cyclic.

Examples of the linear or branched aliphatic hydrocarbon group include a linear aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group; and branched aliphatic hydrocarbon groups such as tyl group, neopentyl group and 2-ethylhexyl group. The aliphatic hydrocarbon group preferably has 1 to 6 carbon atoms, more preferably 1 to 5 carbon atoms, and further Preferably it is 1-4.

The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The carbon number of the cyclic aliphatic hydrocarbon group is , Preferably it is 3-8, More preferably, it is 3-6.

The aliphatic hydrocarbon group having 1 to 8 carbon atoms represented by R ^a3 to R ^a8 is each independently preferably a hydrogen atom or a linear or branched aliphatic hydrocarbon group having 1 to 6 carbon atoms, and a hydrogen atom or a straight chain having 1 to 4 carbon atoms. An alkyl group is more preferable, and a methyl group or an ethyl group is still more preferable.

Examples of the aromatic hydrocarbon ring having 6 to 20 carbon atoms represented by the rings T ⁵ and T ⁶ include aromatic monocyclic hydrocarbons such as benzene, toluene, xylene, mesitylene, cumene, and cymene; pentalene, indene, naphthalene, azylene, heptalene, Biphenylene, as-indacene, s-indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceantolylene, triphenylene, pyrene, chrysene Condensed polycyclic hydrocarbons such as , tetracene; and the like. The aromatic hydrocarbon ring preferably has 6 to 16 carbon atoms, more preferably 6 to 10 carbon atoms.

Rings T ⁵ and T ⁶ are each independently, preferably benzene, naphthalene, phenalene or anthracene, more preferably benzene or naphthalene.

Rings T ⁵ and T ⁶ may be the same or different.

The aromatic heterocycle represented by the ring T ¹ , the nitrogen-containing aromatic heterocycle containing N or N ⁺ as constituent atoms of the ring represented by the ring T ² , and the aromatic hydrocarbon ring having 6 to 20 carbon atoms represented by the rings T ⁵ and T ⁶ are substituents The substituent may include an oxo group; a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, or a bromine atom; a nitro group; a cyano group; a -N(R ^a1 )(R ^a2 ) group (wherein R ^a1 and R ^a2 are the same as above); a hydroxy group; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group; a sulfanyl group; an alkylsulfanyl group having 1 to 6 carbon atoms such as a methylsulfanyl group and an ethylsulfanyl group; Carboxyl group; Carbamoyl group; Methoxycarbonyl group, alkoxycarbonyl group having 1 to 6 carbon atoms such as ethoxycarbonyl group; Sulfo group; sulfamoyl group; Methoxysulfonyl group, ethoxysulfonyl group, etc. having 1 to 6 carbon atoms Alkoxysulfonyl group; etc. are mentioned.

In the formula (I), ring T ¹ is bonded to L ¹ and a carbon atom at a portion from which two arbitrary hydrogen atoms included in ring T ¹ are separated, and ring T ² is any of those included in ring T ² . It bonds with L ² and a carbon atom at the portion where two hydrogen atoms are separated.

Rings T ¹ and T ² may be the same or different.

The divalent hydrocarbon group having 1 to 8 carbon atoms represented by L ¹ and L ² is a divalent group derived by removing two arbitrary hydrogen atoms from a hydrocarbon having 1 to 8 carbon atoms, and is a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms. Or a C6-C8 divalent aromatic hydrocarbon group is mentioned.

Examples of the divalent aliphatic hydrocarbon group include a divalent chain hydrocarbon group having 1 to 8 carbon atoms or a divalent alicyclic hydrocarbon group having 3 to 8 carbon atoms.

The divalent chain aliphatic hydrocarbon group includes 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 hexane. Alkanediyl groups, such as a -1,6-diyl group, a heptane-1,7-diyl group, and an octane-1,8-diyl group, etc. are mentioned.

Examples of the divalent alicyclic hydrocarbon group include cyclopropane-1,1-diyl group, cyclopropane-1,2-diyl group, cyclobutane-1,1-diyl group, cyclobutane-1,2-diyl group, cyclo Butane-1,3-diyl group, cyclopentane-1,1-diyl group, cyclopentane-1,2-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,1-diyl group, cyclo hexane-1,2-diyl group, cyclohexane-1,3-diyl group, cyclohexane-1,4-diyl group, and groups represented by formulas (L-a1) to (L-a6); there is.

The divalent aromatic hydrocarbon group having 6 to 8 carbon atoms is preferably a divalent aromatic monocyclic hydrocarbon group having 6 to 8 carbon atoms, and as the divalent aromatic monocyclic hydrocarbon group, o-phenylene group, m-phenylene group, p-phenylene group, and The group etc. which are represented by a formula (L-b1) - a formula (L-b6) are mentioned.

The divalent hydrocarbon group having 1 to 8 carbon atoms represented by L ¹ and L ² is preferably a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 8 carbon atoms, and more preferably a divalent hydrocarbon group having 1 to 8 carbon atoms. A divalent chain hydrocarbon group of 8 or a divalent aromatic monocyclic hydrocarbon group having 6 to 8 carbon atoms, more preferably an alkanediyl group having 1 to 8 carbon atoms or a divalent aromatic monocyclic hydrocarbon group having 6 to 7 carbon atoms, particularly preferably is a linear alkanediyl group having 1 to 8 carbon atoms or a divalent aromatic monocyclic hydrocarbon group having 6 carbon atoms.

Moreover, carbon number of the said divalent aliphatic hydrocarbon group becomes like this. Preferably it is 1-6, More preferably, it is 1-4.

The divalent hydrocarbon group having 1 to 8 carbon atoms in L ¹ and L ² may have a substituent, and examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom and a bromine atom; a nitro group; a cyano group; an amino group. ; Hydroxy group; A methoxy group, an alkoxy group having 1 to 6 carbon atoms, such as an ethoxy group; a sulfanyl group; a methylsulfanyl group, an alkylsulfanyl group having 1 to 6 carbon atoms, such as an ethylsulfanyl group; Alkoxycarbonyl groups having 1 to 6 carbon atoms such as a carbonyl group and an ethoxycarbonyl group; a sulfo group; a sulfamoyl group; an alkoxysulfonyl group having 1 to 6 carbon atoms such as a methoxysulfonyl group and an ethoxysulfonyl group; .

It is more preferable that the said divalent hydrocarbon group does not have a substituent.

L ¹ and L ² are each independently, preferably a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a formula (L-b1) to a formula (L-b6) ), o-phenylene group, m-phenylene group or p-phenylene group, more preferably methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, o -phenylene group, m-phenylene group, or p-phenylene group. In addition, L ¹ and L ² may be the same or different, but preferably the same.

k is preferably 3 or less, and more preferably 2 or less. In the formula (I), the carbon-carbon double bond indicated by arrows s and t may be in either the E configuration or the Z configuration. That is, formula (I) is defined as including all geometric isomers resulting from carbon-carbon double bonds indicated by arrows s and t, and formulas (II), (III-A) and (III-B) is also the same in

Examples of the n-valent metal ion represented by M ⁿ⁺ include alkaline earth metal ions such as magnesium ion, calcium ion, strontium ion, and barium ion; titanium ion, zirconium ion, chromium ion, manganese ion, iron ion, cobalt ion, nickel ion, copper ion. Transition metal ions, such as; Typical metal ions, such as a zinc ion, a cadmium ion, an aluminum ion, an indium ion, a tin ion, a lead ion, and a bismuth ion; etc. are mentioned.

n becomes like this. Preferably it is 4 or less, More preferably, it is 3 or less, More preferably, it is 2.

Since compound (I) has a valence of 0, that is, an electrically neutral compound, the number r of M ⁿ⁺ is selected such that the valence of compound (I) is 0. r is preferably 1 or 2, more Preferably it is 1.

M ⁿ⁺ is more preferably an alkaline earth metal ion or a typical metal ion, still more preferably a magnesium ion, a barium ion, or an aluminum ion, and still more preferably a barium ion or an aluminum ion.

Compound (I) is preferably a compound represented by formula (II) (hereinafter sometimes referred to as compound (II)).

[In formula (II), L ¹ , L ² , k, r, M ⁿ⁺ , and n are the same as above.

Ring T ³ represents the nitrogen-containing aromatic heterocycle which may have a substituent.

Ring T ⁴ represents a nitrogen-containing aromatic heterocycle containing N or N ⁺ in a constituent atom of the ring which may have a substituent.

L ³ represents a single bond or -CO-.

L ⁴ represents a double bond or -CO-.]

The nitrogen-containing aromatic heterocycle represented by the ring T ³ is a nitrogen-containing aromatic heterocycle containing a nitrogen atom as a component of the ring, the nitrogen atom is >N-, the ring-forming atom has a ð electron, and the ring T ³ is a formula (T ³ -A), a ring represented by a formula (T ³ -B), a formula (T ³ -C), or a formula (T ³ -D) is preferable.

The nitrogen-containing aromatic heterocycle containing N or N ⁺ as a constituent atom of the ring represented by the ring T ⁴ contains a nitrogen atom as a constituent element of the ring, the nitrogen atom is -N< or >N ⁺ <, and the ring-forming atom is ð It is a nitrogen-containing aromatic heterocycle having an electron, and as ring T ⁴ , a ring represented by a formula (T ⁴ -A), a formula (T ⁴ -B), a formula (T ⁴ -C) or a formula (T ⁴ -D) is desirable.

Rings T ³ and T ⁴ may be the same or different.

[Formula (T ³ -A), Formula (T ³ -B), Formula (T ³ -C), Formula (T ³ -D), Formula (T ⁴ -A), Formula (T ⁴ -B), Formula In (T ⁴ -C) and (T ⁴ -D), X ^1a , X ^2a , X ^1b , X ^2b , ring T ⁵ , and ring T ⁶ are the same as above.

L means a bond with L ¹ or L ² , and C means a bond with a carbon atom.]

Ring T ¹ and ring T ³ are more preferably a ring represented by a formula (R ³ -1) to a formula (R ³ -7), still more preferably a formula (R ³ -1) to a formula (R ³ -3) , a ring represented by the formula (R ³ -7). The ring T ² and the ring T ⁴ are more preferably a ring represented by the formulas (R ⁴ -1) to (R ⁴ -7), still more preferably the formula ( It is a ring represented by R ⁴ -1) to a formula (R ⁴ -3) and a formula (R ⁴ -7).

Compound (I) and compound (II) are more preferably a compound represented by formula (III-A) (hereinafter sometimes referred to as compound (III-A)) or a compound represented by formula (III-B) ( Hereinafter, it may be referred to as compound (III-B)).

[In formula (III-A), ring T ⁵ , ring T ⁶ , L ¹ , L ² , k, r, M ⁿ⁺ , and n are the same as above.]

[In formula (III-B), L ¹ , L ² , k, r, M ⁿ⁺ , and n are the same as above.]

Examples of compound (I) include compounds represented by formulas (I-1) to (I-189) shown in Tables 1-3. Compound (I) is preferably a formula (I-1) - Formula (I-63), Formula (I-127) - a compound represented by Formula (I-168), More preferably, Formula (I-43) - Formula (I-63), Formula (I-127) - Formula (I-133), Formula (I-148) - a compound represented by Formula (I-154), More preferably, Formula (I-43) - Formula (I-54), Formula (I-131) It is a compound represented by - formula (I-133), formula (I-152) - formula (I-154).

In Tables 1 to 3, ring T ¹ represents a ring represented by a formula (R ³ -a1) to a formula (R ³ -a4), and a ring T ² is a formula (R ⁴ -a1) to a formula (R ⁴ -a4) represents a ring represented by . In formulas (R ³ -a1) to (R ³ -a4) and (R ⁴ -a1) to (R ⁴ -a4), L and C are the same as above.

In Tables 1-3, L< ¹ > and L< ² > represent the divalent hydrocarbon group represented by Formula (L-1) - Formula (L-7). In formulas (L-1) to (L-7), n means a bond with a nitrogen atom, and s means a bond with a sulfur atom.

The compound represented by the formula (I) is a compound represented by the formula (pt3) and a halide (preferably a chloride) containing an n-valent metal ion, a hydroxide, an acetate, a phosphate, a sulfate, a silicate, or a cyanide It can be prepared by reacting

In addition, L ¹ and L ² are the same, and the compound represented by the same formula (pt3) except that the ring T ¹ and the ring T ² is >N-CH<⇔>N ⁺ =C< in each ring is a formula It can be produced by reacting the compound represented by (pt1) with the compound represented by formula (pt2) under acidic or alkaline conditions. In this reaction, the amount of the compound represented by formula (pt1) to be used is It is preferable that it is 1.5-2.5 mol with respect to 1 mol of compound.

[In formula (pt2), R ^c is a hydrogen atom, a nitro group, or a halogen atom. k is the same as above.

In formulas (pt1), (pt3), and (I), ring T ¹ , ring T ² , L ¹ , L ² , k, M ⁿ⁺ , and n are the same as above.

It is preferable that content of compound (I) is 0.1-150 mass parts with respect to 100 mass parts of resin (B), It is more preferable that it is 1-100 mass parts, It is still more preferable that it is 5-80 mass parts.

The colored resin composition of this invention may contain the dye (A1) and the pigment (A2) other than compound (I) as a coloring agent (A).

The dye (A1) is not particularly limited, and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. As the dye, for example, the color index (The The compounds classified as having a color other than pigments by the Society of Dyers and Colorists) and the well-known dyes described in the dyeing notes (color dyes) are mentioned. Further, according to the chemical structure, azo dyes, Cyanine dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, anthracenequinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin dye , quinoline dyes, nitro dyes, and the like. Of these, organic solvent-soluble dyes are preferable.

It does not specifically limit as a pigment (A2), A well-known pigment can be used, For example, the pigment classified into the pigment by the color index (The Society of Dyers and Colorists publication) is mentioned.

As the pigment, for example, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139 , 147, 148, 150, 153, 154, 166, 173, 194, 214 yellow pigments;

C.I. Orange pigments, such as pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

C.I. Red pigments such as Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 ;

C.I. Blue pigments, such as pigment blue 15, 15:3, 15:4, 15:6, 60; C.I. Violet pigments, such as pigment violet 1, 19, 23, 29, 32, 36, 38;

C.I. Green pigments, such as pigment green 7, 36 and 58;

C.I. Brown pigments, such as Pigment Brown 23 and 25;

C.I. Black pigments, such as Pigment Black 1 and 7, etc. are mentioned.

To [ the content rate of a coloring agent (A) ] with respect to the total amount of solid content, Preferably it is 0.1-70 mass %, More preferably, it is 0.5-60 mass %, More preferably, it is 1-50 mass %.

It is preferable that it is 50 mass % or more in the total amount of a coloring agent (A), as for the content rate of a compound (I), it is more preferable that it is 80 mass % or more, It is still more preferable that it is 90 mass % or more.

Here, the "total amount of solid content" in this specification means the amount obtained by removing the content of the solvent from the total amount of the colored resin composition. It can measure by well-known analytical means, such as gas chromatography.

<Resin (B)>

Although resin (B) is not specifically limited, It is preferable that it is an alkali-soluble resin, At least 1 type (a) (hereafter referred to as "(a)") selected from the group which consists of unsaturated carboxylic acid and unsaturated carboxylic acid anhydride A resin having a structural unit derived from ) is more preferable. The resin (B) further has a cyclic ether structure having 2 to 4 carbon atoms and a monomer (b) having an ethylenically unsaturated bond (hereinafter referred to as “(b)”). Structural unit derived from (a) and monomer (c) copolymerizable with (a) (however, (a) and (b) are different.) (hereinafter referred to as "(c)") It is preferable to have at least 1 sort(s) of structural unit selected from the group which consists of a structural unit derived from and the structural unit which has an ethylenically unsaturated bond in a side chain.

Specifically as (a), for example, acrylic acid, methacrylic acid, maleic anhydride, itaconic acid anhydride, 3,4,5,6-tetrahydrophthalic anhydride, succinic acid mono[2-(meth)acrylo yloxyethyl], etc. are mentioned, Preferably, they are acrylic acid, methacrylic acid, and maleic anhydride.

(b) is a monomer having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane and a tetrahydrofuran ring) and a (meth)acryloyloxy group is preferable

In addition, in this specification, "(meth)acrylic acid" represents at least 1 sort(s) selected from the group which consists of acrylic acid and methacrylic acid. "(meth)acryloyl" and "(meth)acrylate" The notation also has the same meaning.

As (b), for example, glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, 3-ethyl -3-(meth)acryloyloxymethyloxetane, tetrahydrofurfuryl(meth)acrylate, etc. are mentioned, Preferably, glycidyl (meth)acrylate, 3,4-epoxytricyclo[ 5.2.1.0 ^2,6 ] It is decyl (meth)acrylate and 3-ethyl-3- (meth)acryloyloxymethyloxetane.

As (c), for example, methyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^{2, 6} ]Decan-8-yl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide; styrene, vinyltoluene, etc. are mentioned, Preferably, styrene, vinyltoluene, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, etc. are mentioned desirable.

The resin having a structural unit having an ethylenically unsaturated bond in the side chain is obtained by adding (b) to the copolymer of (a) and (c), or adding (a) to the copolymer of (b) and (c). This resin may be a resin in which (a) is added to the copolymer of (b) and (c) and further reacted with a carboxylic acid anhydride.

Preferably the weight average molecular weight of polystyrene conversion of resin (B) is 3,000-100,000, More preferably, it is 5,000-50,000, More preferably, it is 5,000-30,000.

The dispersion degree [weight average molecular weight (Mw)/number average molecular weight (Mn)] of resin (B) becomes like this. Preferably it is 1.1-6, More preferably, it is 1.2-4.

The acid value of the resin (B) is preferably 20 to 170 mg-KOH/g in terms of solid content, more preferably 30 to 150 mg-KOH/g, and still more preferably 40 to 135 mg-KOH/g. An acid value is a value measured as quantity (mg) of potassium hydroxide required in order to neutralize 1 g of resin (B), For example, it can obtain|require by titrating using potassium hydroxide aqueous solution.

To [ the content rate of resin (B) ] with respect to the total amount of solid content, Preferably it is 7-65 mass %, More preferably, it is 13-60 mass %, More preferably, it is 17-55 mass %.

The colored resin composition of the present invention may contain the polymerizable compound (C) and the polymerization initiator (D). Hereinafter, the colored resin composition containing the polymerizable compound (C) and the polymerization initiator (D) is referred to as “coloring curability. A resin composition" in some cases.

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized with active radicals and/or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, etc., preferably Preferably, it is a (meth)acrylic acid ester compound.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of the polymerizable compound include trimethylolpropane tri(meth)acrylate, penta Erythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, etc. are mentioned.

The weight average molecular weight of a polymeric compound (C) becomes like this. Preferably it is 150 or more and 2,900 or less, More preferably, they are 250 or more and 1,500 or less.

When a polymeric compound (C) is included, it is preferable that the content rate of a polymeric compound (C) is 7-65 mass % with respect to the total amount of solid content, More preferably, it is 13-60 mass %, More preferably Usually, it is 17-55 mass %.

<Polymerization initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating active radicals, acids, etc. under the action of light or heat, and any known polymerization initiator can be used. Examples of the polymerization initiator include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane- 1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, 2-methyl-2-morpholino-1-( 4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexylphenylketone, 2,4- Bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'-bis(2-chlorophenyl)-4 ,4',5,5'-tetraphenylbiimidazole, etc. are mentioned.

When a polymerization initiator (D) is included, content of a polymerization initiator (D) with respect to 100 mass parts of total amounts of resin (B) and a polymeric compound (C), Preferably it is 0.1-30 mass parts, More preferably It is preferably 1 to 20 parts by mass. When the content of the polymerization initiator (D) is within the above range, the productivity of the color filter is improved because it tends to increase the sensitivity and shorten the exposure time.

The colored resin composition of this invention may contain the polymerization initiation adjuvant (D1).

<Polymerization initiation aid (D1)>

The polymerization initiation assistant (D1) is a compound or sensitizer used to promote polymerization of a polymerizable compound whose polymerization is initiated by the polymerization initiator. When the polymerization initiation assistant (D1) is included, the polymerization initiator (D) is usually ) is used in combination with

Examples of the polymerization initiation auxiliary (D1) include 4,4'-bis(dimethylamino)benzophenone (common name mihirazketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, N-phenylglycine, etc. are mentioned.

When using these polymerization initiation adjuvant (D1), the content is with respect to 100 mass parts of total amounts of resin (B) and a polymeric compound (C), Preferably it is 0.1-30 mass parts, More preferably, it is 1-20 mass parts. It is a mass part. When the amount of the polymerization initiation auxiliary (D1) is within this range, a coloring pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

The colored resin composition of this invention may contain the solvent (E).

<Solvent (E)>

The solvent (E) is not particularly limited, and a solvent commonly used in this field can be used. For example, an ester solvent (a solvent containing -COO- in the molecule and not containing -O-), ether Solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (containing -CO- in the molecule) and -COO-free solvents), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.

As a solvent,

Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and γ-butyrolactone (in the molecule - Solvent containing COO- and not containing -O-);

Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether (in the molecule -O- and a solvent that does not contain -COO-);

Ether ester solvents such as 3-methoxy methyl propionate, 3-ethoxy ethyl propionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate (in the molecule Solvent containing -COO- and -O-);

Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, and cyclohexanone (with -CO- in the molecule and without -COO- solvent);

Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-);

Amide solvents, such as N,N- dimethylformamide, N,N- dimethylacetamide, and N-methylpyrrolidone; etc. are mentioned.

As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and ethyl 3-ethoxypropionate are more preferable.

When the solvent (E) is included, the content rate of the solvent (E) is preferably 70 to 95 mass%, more preferably 75 to 92 mass%, with respect to the total amount of the colored resin composition of the present invention. In other words, the total amount of solid content of the colored resin composition is preferably 5 to 30 mass %, more preferably 8 to 25 mass %. When the content of the solvent (E) is within the above range, the flatness at the time of application is good. Moreover, since color density does not run short when a color filter is formed, there exists a tendency for a display characteristic to become favorable.

The colored resin composition of this invention may contain the leveling agent (F).

<Leveling agent (F)>

As a leveling agent (F), a silicone type surfactant, a fluorine type surfactant, the silicone type surfactant etc. which have a fluorine atom are mentioned. These may have a polymeric group in a side chain.

Examples of the silicone-based surfactants include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan Joint Stock Company).

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florad (registered trademark) FC430, copper FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megapack (registered) Trademark) F142D, Dong F171, Dong F172, Dong F173, Dong F177, Dong F183, Dong F554, Dong R30, Dong RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, Dong EF303, Copper EF351, Copper EF352 (manufactured by Mitsubishi Materials Electric Chemical Co., Ltd.), Suflon (registered trademark) S381, Copper S382, Copper SC101, Copper SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (Daikin Tablets) Chemicals Research Institute), etc. are mentioned.

Examples of the silicone-based surfactants having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megapack (registered trademark) R08, BL20, F475, F477, F477. and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is included, the content of the leveling agent (F) is preferably 0.001 to 0.2 mass%, more preferably 0.002 to 0.1 mass%, with respect to the total amount of the colored resin composition. Content of a pigment dispersant is not included in this content. When content of a leveling agent (F) exists in said range, flatness of a color filter can be made favorable.

<Other ingredients>

The colored resin composition of this invention may contain well-known additives in the said technical field, such as a filler, another high molecular compound, an adhesion promoter, antioxidant, an optical stabilizer, and a chain transfer agent, as needed.

<The manufacturing method of a colored resin composition>

The colored resin composition of this invention is a coloring agent (A) and resin (B), and a polymeric compound (C) used as needed, a polymerization initiator (D), a polymerization initiation adjuvant (D1), a solvent (E), a leveling It can prepare by mixing agent (F) and another component.

<The manufacturing method of a color filter>

As a method of manufacturing a colored pattern from the colored resin composition of this invention, the photolithography method, the inkjet method, the printing method, etc. are mentioned. Especially, the photolithographic method is preferable.

When the colored resin composition contains the compound (I) as a colorant, a color filter particularly excellent in contrast and light resistance can be produced. The color filter is a display device (eg, a liquid crystal display device, an organic EL device, electronic paper etc.) and it is useful as a color filter used for a solid-state image sensor.

[Example]

Hereinafter, the colored resin composition of the present invention will be described in more detail by way of Examples. In Examples, "%" and "part" are mass % and parts by mass, unless otherwise specified.

Example 1

9.2 parts of the compound represented by the formula (1-1) and 5.5 parts of the compound represented by the formula (1-2) were added to 18 parts of acetic anhydride, and mixed at room temperature. Next, after adding 8 parts of triethylamine, at 40°C After the reaction was completed, 100 parts of ethyl acetate was added to precipitate crystals, which were filtered. The compound 8.4 represented by formula (1-3) was washed 3 times with 80 parts of ethyl acetate and dried under reduced pressure at 60°C. got wealth

11 parts of the compound represented by Formula (1-3) were added to 100 parts of water to prepare a solution (aqueous solution 1) in which the compound represented by Formula (1-3) was dissolved. Separately, 19.5 parts of barium chloride dihydrate 80 parts of water A solution (aqueous solution 2) was prepared, and aqueous solution 2 was added dropwise to aqueous solution 1 at 40°C over 2 hours, followed by stirring for 4 hours. After cooling, it was filtered and washed twice with 100 parts of ion-exchanged water. and dried under reduced pressure at 100°C to obtain 18 parts of a compound represented by the formula (I-52).

Example 2

5.2 parts of the compound represented by Formula (2-1) were added to 100 parts of water, to prepare a solution (aqueous solution 1) in which the compound represented by Formula (2-1) was dissolved. Separately, 7.1 parts of aluminum hydroxide was dissolved in 80 parts of water. The prepared solution (aqueous solution 2) was prepared, and the aqueous solution 2 was added dropwise to the aqueous solution 1 at 40° C. over 2 hours, followed by stirring for 4 hours. After cooling, it was filtered and washed twice with 100 parts of ion-exchanged water; The crystals were dried under reduced pressure at 100°C to obtain 1.8 parts of the compound represented by the formula (I-152).

Example 3

5.2 parts of the compound represented by Formula (2-1) were added to 100 parts of water to prepare a solution (aqueous solution 1) in which the compound represented by Formula (2-1) was dissolved. Separately, 12.2 parts of barium chloride dihydrate to 80 parts of water A dissolved solution (aqueous solution 2) was prepared, and aqueous solution 2 was added dropwise to aqueous solution 1 at 40° C. over 2 hours, followed by stirring for 4 hours. After cooling, it was filtered and washed twice with 100 parts of ion-exchanged water. , the crystals were dried under reduced pressure at 100°C to obtain 5.9 parts of a compound represented by the formula (I-131).

[Synthesis Example 1]

In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, an appropriate amount of nitrogen was flowed into a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 80° C. while stirring. Next, in the flask, 38 parts of acrylic acid , a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-ylacrylate (trade name) A solution in which 289 parts of "E-DCPA", manufactured by Daicel Co., Ltd.) was dissolved in 125 parts of propylene glycol monomethyl ether acetate was added dropwise over about 5 hours using a dropping pump. On the other hand, polymerization initiator 2,2-azo A solution in which 33 parts of bis(2,4-dimethylvaleronitrile) was dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise into the flask over about 6 hours using another dropping pump. After holding, it was cooled to room temperature to obtain a copolymer (resin (B-2)) having a solid content of 35.1%. The obtained copolymer had a weight average molecular weight Mw of 9200, a dispersion degree of 2.08, and an acid value in terms of solid content of 77 mg-KOH. /g. Resin (B-2) has the following structural unit.

The measurement of the polystyrene conversion weight average molecular weight (Mw) and number average molecular weight (Mn) of resin was performed on condition of the following by gel permeation chromatography (GPC method).

Apparatus; HLC-8120 GPC (manufactured by Tosoh Corporation)

Column; TSK-GELG2000HXL

Column temperature; 40°C

solvent; THF

Flow rate; 1.0mL/min

Test solution solid content concentration; 0.001 to 0.01 mass%

Injection volume; 50 μL

detector; RI

Reference material for calibration; TSKSTANDARDPOLYSTYRENE

F-40, F-4, F-288, A-2500, A-500

(manufactured by Toso Co., Ltd.)

Ratio (Mw/Mn) of the polystyrene conversion weight average molecular weight and number average molecular weight obtained above was made into the dispersion degree.

Example 4

[Preparation of dispersion (P-1)]

10 parts of the compound represented by formula (I-52), 4 parts of solid content of dispersant BYK-LPN6919 (manufactured by BYK), 5 parts of resin (B-2) solution (35.0% of solid content) to solid content, propylene glycol monomethyl ether After weighing 181 parts of acetate, 300 parts of 0.4 micrometers zirconia beads were put, and it shook for 6 hours using the paint conditioner (made by LAU), the zirconia beads were removed by filtration, and the dispersion liquid (P-1) was produced.

[Preparation of colored resin composition]

Each component was mixed so that it might become a composition shown in Table 4, and the colored resin composition was obtained.

Comparative Example 1

Except having changed the dispersion liquid (P-1) into the coloring agent (A-1), it carried out similarly to Example 4, and obtained the colored resin composition.

In Table 4, each component shows the following compounds.

Coloring agent (A-1): The compound represented by Formula (3)

Resin (B-2): Resin (B-2) (in terms of solid content)

Polymeric compound (C-1): dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

Polymerization initiator (D-1): N-benzoyloxy-1-(4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE01; manufactured by BASF)

Solvent (E-1): Propylene glycol monomethyl ether acetate

Example 5

[Preparation of dispersion (P-2)]

In Example 4, a dispersion (P-2) was prepared in the same manner as in Example 4 except that the compound represented by the formula (I-52) was replaced with the compound represented by the formula (I-152).

[Preparation of colored resin composition]

Each component was mixed so that it might become a composition shown in Table 5, and the colored resin composition was obtained.

Example 6

[Preparation of dispersion (P-3)]

In Example 4, a dispersion (P-3) was prepared in the same manner as in Example 4 except that the compound represented by the formula (I-52) was replaced with the compound represented by the formula (I-131).

[Preparation of colored resin composition]

Each component was mixed so that it might become a composition shown in Table 5, and the colored resin composition was obtained.

Comparative Example 2

Except having changed the dispersion liquid (P-1) into the coloring agent (2-1), it carried out similarly to Example 5, and obtained the colored resin composition.

In Table 5, each component shows the following compounds.

Coloring agent (2-1): The compound represented by Formula (2-1)

Resin (B-2): Resin (B-2) (in terms of solid content)

Polymeric compound (C-1): dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

Polymerization initiator (D-1): N-benzoyloxy-1-(4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE01; manufactured by BASF)

Solvent (E-1): Propylene glycol monomethyl ether acetate

<Production of the coloring pattern>

On a 5 cm corner glass substrate (Eagle 2000; manufactured by Corning), the colored resin composition was applied by spin coating, and then prebaked at 100° C. for 3 minutes to obtain a colored composition layer. After standing to cool, a colored composition layer was formed The distance between the substrate and the quartz glass photomask was set to 100 µm, and the light was irradiated with an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) at an exposure dose (365 nm standard) of 150 mJ/cm 2 in an atmospheric atmosphere. , 100 μm line-and-space pattern formed was used. The colored composition layer after light irradiation was immersed in an aqueous developer solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 24° C. for 60 seconds. After washing, In oven, 200 degreeC 20 minutes post-baking was performed, and the coloring pattern was obtained.

<Contrast evaluation>

About the coloring pattern obtained in Example 4 and Comparative Example 1, Contrast system (CT-1; Tsubosaka Electric Co., Ltd. make, color difference meter BM-5A; Topcon company make, light source; F-10, Polarizing film; Tsubosaka Corporation) ), the contrast was measured with a blank value of 30000. Table 6 shows the results.

<Light fastness evaluation>

An ultraviolet cut filter (COLOREDOPTICALGLASSL38; manufactured by Hoya Corporation; cuts light of 380 nm or less) is placed on the obtained coloring pattern, and a xenon lamp light is irradiated with a light resistance tester (SUNTESTCPS+: manufactured by Toyo Seiki) for 48 hours, after irradiation The chromaticity of the coloring pattern was measured, and the color difference ΔEab before and after irradiation was obtained by the method described in JISZ8730:2009 (7. Color difference calculation method) from the measured value. Spectroscopy was measured using Co., Ltd., and the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ table color system were measured using the isochromatic function of the C light source. Table 7 shows the results. .

ADVANTAGE OF THE INVENTION According to the colored resin composition of this invention, the color filter excellent in contrast and light resistance can be produced.

Claims (7)

a colorant and a resin;
The colored resin composition in which the said coloring agent contains the compound represented by Formula (I).
[Formula 1]

[In formula (I),
Ring T ¹ is any one of rings represented by the following formulas (R ³ -a1) to (R ³ -a4);
Ring T ² is any one of rings represented by the following formulas (R ⁴ -a1) to (R ⁴ -a4).
L ¹ and L ² are each independently any one of groups represented by the following formulas (L-1) to (L-7).
k represents an integer of 0 or more and 4 or less.
M ⁿ⁺ represents an n-valent metal cation.
n represents an integer of 2 or more and 5 or less.
r represents the number of M ⁿ⁺ , and is selected so that the valence of formula (I) becomes zero.]

[In formulas (R ³ -a1) to (R ³ -a4) and formulas (R ⁴ -a1) to (R ⁴ -a4), L means a bond with L ¹ or L ² , and C is a carbon atom It means a bond hand with .]

[In formulas (L-1) to (L-7), n means a bond with a nitrogen atom, and s means a bond with a sulfur atom.] delete delete delete The method of claim 1,
Furthermore, the colored resin composition containing a polymeric compound and a polymerization initiator. The color filter formed from the colored resin composition in any one of Claims 1 and 5. The display device of claim 6 , further comprising a color filter.