TW202200592A - Coloring resin composition capable of manufacturing a color filter with higher brightness in green color - Google Patents

Abstract

An object of the present invention is to provide a color filter with higher brightness in green color, and a coloring resin composition that can be used to manufacture the color filter. The coloring resin composition of the present invention is characterized by including a colorant and a resin, and the colorant contains a phthalocyanine compound in which one or more hydrogen atoms are replaced with SF5, and the colorant contains at least on pigment selected from the group consisting yellow pigment and green pigment.

Description

Colored resin composition

The present invention relates to a colored resin composition. Specifically, it relates to a colored resin composition containing a phthalocyanine compound.

The color filter used for liquid crystal display devices etc. is manufactured from a coloring curable resin composition. Phthalocyanine dye is known as a coloring agent contained in the coloring curable resin composition for this color filter formation (patent document 1). [Prior Art Literature] [Patent Literature]

[Patent Document 1] International Publication No. 2016/076028

[Problems to be Solved by Invention]

In recent years, there has been a pursuit to improve the green brightness of color filters. The object of the present invention is to provide a color filter with high green brightness and a coloring resin composition that can be used for manufacturing the color filter. [Technical means to solve problems]

The present invention includes the following inventions. [1] A coloring resin composition comprising a colorant and a resin, wherein the colorant contains a phthalocyanine compound in which one or more hydrogen atoms are substituted with SF ₅ . [2] The colored resin composition according to [1], wherein the colorant contains a compound represented by the following formula (1a) and/or (1b):

[hua 1]

[式(1a)、式(1b)中， R^x 分別獨立地表示SF₅ 、或1個以上之氫原子被取代為SF₅ 之碳數1～20之烴基， m表示1～16之整數， R^y 分別獨立地表示可具有取代基之碳數1～20之烴基， n表示0～15之整數， M表示可具有取代基之金屬元素、或可具有取代基之半金屬元素， R^x 及R^y 所表示之烴基之-CH₂ -可被取代為-O-、-S-、-SO₂ -、-NH-、-CO-或-CO₂ -]。 [3]如[2]所記載之著色樹脂組合物，其中上述式(1a)所表示之化合物為下述式(2a)所表示之化合物，上述式(1b)所表示之化合物為下述式(2b)所表示之化合物。[hua 2]

[In formula (1a) and formula (1b), R ^x each independently represents SF ₅ , or a hydrocarbon group having 1 to 20 carbon atoms in which one or more hydrogen atoms are substituted with SF ₅ , m represents an integer of 1 to 16, R ^y each independently represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, n represents an integer of 0 to 15, M represents an optionally substituted metal element or an optionally substituted semimetal element, R ^x and -CH ₂ - of the hydrocarbon group represented by R ^y may be substituted with -O-, -S-, -SO ₂ -, -NH-, -CO- or -CO ₂ -]. [3] The colored resin composition according to [2], wherein the compound represented by the above formula (1a) is a compound represented by the following formula (2a), and the compound represented by the above formula (1b) is the following formula The compound represented by (2b).

[hua 3]

[式(2a)、式(2b)中， R^x 、R^y 、M分別表示與上文所述相同之含義， o表示1～4之整數， p表示0～3之整數]。 [4]如[1]至[3]中任一項所記載之著色樹脂組合物，其中上述著色劑包含選自由黃色顏料及綠色顏料所組成之群中之至少一種顏料。 [5]一種著色硬化性樹脂組合物，其包含如[1]至[4]中任一項所記載之著色樹脂組合物、聚合性化合物、聚合起始劑。 [6]一種彩色濾光片，其係由如[5]所記載之著色硬化性樹脂組合物形成。 [7]一種顯示裝置，其包含如[6]所記載之彩色濾光片。 [發明之效果][hua 4]

[In formula (2a) and formula (2b), R ^x , R ^y , and M respectively have the same meanings as described above, o represents an integer of 1 to 4, and p represents an integer of 0 to 3]. [4] The colored resin composition according to any one of [1] to [3], wherein the colorant contains at least one pigment selected from the group consisting of a yellow pigment and a green pigment. [5] A colored curable resin composition comprising the colored resin composition according to any one of [1] to [4], a polymerizable compound, and a polymerization initiator. [6] A color filter formed from the coloring curable resin composition as described in [5]. [7] A display device comprising the color filter as described in [6]. [Effect of invention]

According to the present invention, it is possible to provide a color filter with high green brightness, and a coloring resin composition that can be used to manufacture the color filter.

The colored resin composition of the present invention contains a colorant (hereinafter, sometimes referred to as a colorant (A)) and a resin (hereinafter, sometimes referred to as a resin (B)). The colorant contains a phthalocyanine compound in which one or more hydrogen atoms are substituted with SF ₅ . Thereby, the brightness of green can be improved. Hereinafter, each component of the colored resin composition will be described. In addition, in this specification, unless otherwise specified, the compound illustrated as each component can be used individually or in combination of a plurality of types.

<Colorant (A)> The colorant (A) preferably contains a compound represented by the following formula (1a) (hereinafter, sometimes referred to as a compound (1a)) and/or a compound represented by the following formula (1b) (hereinafter, sometimes referred to as a compound) is compound (1b)), more preferably contains compound (1a). The colorant (A) may contain the compound (1a) and the compound (1b), or may contain the compound (1a) or the compound (1b).

<Compound (1a), Compound (1b)> The compound (1a) is a compound represented by the following formula (1a), and the compound (1b) is a compound represented by the following formula (1b).

[hua 5]

[式(1a)、式(1b)中， R^x 分別獨立地表示SF₅ 、或1個以上之氫原子被取代為SF₅ 之碳數1～20之烴基， m表示1～16之整數， R^y 分別獨立地表示可具有取代基之碳數1～20之烴基， n表示0～15之整數， M表示可具有取代基之金屬元素、或可具有取代基之半金屬元素， R^x 及R^y 所表示之烴基之-CH₂ -亦可取代為-O-、-S-、-SO₂ -、-NH-、-CO-或-CO₂ -]。[hua 6]

[In formula (1a) and formula (1b), R ^x each independently represents SF ₅ , or a hydrocarbon group having 1 to 20 carbon atoms in which one or more hydrogen atoms are substituted with SF ₅ , m represents an integer of 1 to 16, R ^y each independently represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, n represents an integer of 0 to 15, M represents an optionally substituted metal element or an optionally substituted semimetal element, R ^x and -CH ₂ - of the hydrocarbon group represented by R ^y may also be substituted with -O-, -S-, -SO ₂ -, -NH-, -CO- or -CO ₂ -].

R ^y may be a substituted hydrocarbon group having 1 to 20 carbon atoms or an unsubstituted hydrocarbon group having 1 to 20 carbon atoms, but is preferably an unsubstituted hydrocarbon group having 1 to 20 carbon atoms. _In addition, SF5 is not contained in this substituent.

As R ^y , an aliphatic hydrocarbon group and a group having an aromatic ring (hereinafter, may be referred to as an aromatic ring-containing group) may, for example, be mentioned.

The aliphatic hydrocarbon group in R ^y may be a saturated hydrocarbon group or an unsaturated hydrocarbon group. In addition, the aliphatic hydrocarbon group may be a chain or an alicyclic group. 1-20 are preferable, as for carbon number of aliphatic hydrocarbon group, 1-10 are more preferable, and 1-4 are still more preferable. When the aliphatic hydrocarbon group has a substituent, the carbon number of the substituent also includes the carbon number of the substituent.

As the chain-like saturated hydrocarbon group in R ^y , straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl can be exemplified; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, isopentyl, new Branched chain alkyl groups such as pentyl, tertiary pentyl, (2-methyl)pentyl, isohexyl, (5-methyl)hexyl, (3-ethyl)heptyl, and the like.

Examples of the chain unsaturated hydrocarbon group in R ^y include vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3- Alkenyl such as butenyl, 1,3-butadienyl, (1-(2-propenyl))vinyl, (1,2-dimethyl)propenyl, 2-pentenyl, and the like.

Examples of the alicyclic saturated hydrocarbon group in R ^y include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; normyl, adamantyl, Bicyclo[2.2.2]octyl et al. As an alicyclic unsaturated hydrocarbon group, a cyclohexenyl group (for example, cyclohex-2-ene, cyclohex-3-ene), a cycloheptenyl group, a cycloalkenyl group, such as a cyclooctenyl group, etc. are mentioned.

The aliphatic hydrocarbon group in R ^y may also be formed by a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include 1-methylcyclopropyl, 1-methylcyclohexyl, 2-methyl Cyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 4 -Pentylcyclohexyl, 4-octylcyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl group, 2-methylcyclohexylmethyl, cyclohexylethyl, adamantylmethyl and the like.

The -CH ₂ - of the aliphatic hydrocarbon group in R ^y may be substituted with -O-, -S-, -SO ₂ -, -NH-, -CO- or -CO ₂ - and the like. Examples of the -CH ₂ - substituted aliphatic hydrocarbon group include alkoxy groups such as methoxy and ethoxy; alkylthio groups such as methylthio and ethylthio; methylsulfonyl, ethyl Alkyl sulfonyl group such as sulfonyl group; alkyl amine group such as monomethylamine group, dimethylamine group, monoethylamine group, diethylamine group; ; Methoxycarbonyl, ethoxycarbonyl and other alkoxycarbonyl groups, etc.

The aliphatic hydrocarbon group in R ^y may have a substituent, and examples of the substituent include a halogen atom, a cyano group, a nitro group, a substituted amino group, a hydroxyl group, an amine carboxyl group, an acetyl group, a carboxyl group, and a silyl group. , alkylsilyl group with 3-10 carbon atoms, alkoxysilyl group with carbon number 3-10, etc., preferably alkylsilyl group with carbon number 3-10, alkoxysilyl group with carbon number 3-10 . Alkylsilyl groups and alkoxysilyl groups inhibit migration. As a C3-C10 alkylsilyl group, a trimethylsilyl group, a triethylsilyl group, etc. are mentioned. As a C3-C10 alkoxysilyl group, a trimethoxysilyl group, a triethoxysilyl group, etc. are mentioned. Examples of the aliphatic hydrocarbon group having an alkylsilyl group having 3 to 10 carbon atoms as a substituent include trimethylsilyl alkyl, triethylsilyl alkyl, Oxysilyl alkyl, triethoxysilyl alkyl, etc. As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned, Preferably it is a chlorine atom.

As the aromatic ring-containing group in R ^y , an aromatic hydrocarbon group, an aromatic hydrocarbon group to which an aliphatic hydrocarbon group is bonded, and the like can be exemplified. Examples of the aromatic hydrocarbon group include aromatic hydrocarbon groups such as a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthracenyl group, and a pyrenyl group.

As the aromatic hydrocarbon group to which the aliphatic hydrocarbon group is bonded, an aralkyl group such as a benzyl group, a phenethyl group, and 1-methyl-1-phenylethyl group can be exemplified; Arylalkenyl such as phenyl vinyl group; Arylalkynyl such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl Phenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2,5-diisopropylphenyl, 2,6-diisopropyl phenyl, 2,4,6-triisopropylphenyl, 4-butylphenyl and other alkylaryl groups; 2,3-Dihydro-4-indenyl, 1,2,3,5,6,7-hexahydro-4-second dicyclopentadienophenyl, 5,6,7,8-tetrahydro -1-naphthyl, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl and other aryl groups bonded with alkanediyl; Aryl groups with more than one aryl group bonded to biphenyl group, bitriphenyl group, etc.; Cyclohexylmethylphenyl, benzylphenyl, (dimethyl(phenyl)methyl)phenyl, etc.

The -CH ₂ - of the aromatic hydrocarbon group to which the aliphatic hydrocarbon group is bonded may be substituted with -O-, -S-, -SO ₂ -, -NH-, -CO-, -CO ₂ - and the like. -CH ₂ - The aromatic hydrocarbon group which is substituted with an aliphatic hydrocarbon group, for example, may also be aryloxy groups such as phenoxy, 1-naphthyloxy, 2-naphthyloxy; phenylthio, 1-naphthylthio arylthio groups such as phenylsulfonyl group, 2-naphthylthio group, etc.; phenylsulfonyl group, 1-naphthylsulfonyl group, etc., arylsulfonyl group such as 2-naphthylsulfonyl group; monophenylamine group, diphenyl group arylamino groups such as benzylamino groups; aralkylamino groups such as benzylamino groups; arylcarbonyl groups such as benzyl, 1-naphthylcarbonyl, 2-naphthylcarbonyl, etc.; phenoxycarbonyl, 1-naphthyloxy Aryloxycarbonyl, such as 2-naphthylcarbonyl, 2-naphthyloxycarbonyl, etc.

The aromatic ring-containing group may be substituted on the aromatic cyclic hydrocarbon group or the aliphatic hydrocarbon group bound to the aromatic hydrocarbon group, preferably the aliphatic hydrocarbon group bound by the aromatic hydrocarbon group is substituted base. Examples of the substituent include the same groups as those exemplified as the substituent of the aliphatic hydrocarbon group, and preferably an alkylsilyl group having 3 to 10 carbon atoms and an alkoxysilyl group having 3 to 10 carbon atoms. As the aliphatic hydrocarbon group substituted with an alkylsilyl group having 3 to 10 carbon atoms, an alkoxysilyl group having 3 to 10 carbon atoms, etc., trimethylsilyl alkane having 1 to 4 carbon atoms in the alkyl group can be exemplified. base, triethylsilyl alkyl, trimethoxysilyl alkyl, triethoxysilyl alkyl, etc.

1-5 are preferable and, as for carbon number of the aliphatic hydrocarbon group which the group containing an aromatic ring has, 1-2 are more preferable.

The number of carbon atoms of the aromatic ring-containing group is preferably 6 to 20, more preferably 6 to 15, still more preferably 6 to 10, particularly preferably 6. When the aromatic ring has a substituent, the carbon number of the substituent also includes the carbon number of the substituent.

In formula (1a) and formula (1b), n is preferably an integer of 0 to 15, more preferably an integer of 0 to 8, more preferably an integer of 0 to 4, still more preferably an integer of 0 to 2 , preferably 0. When compound (1a) has a plurality of R ^y 's, R ^y 's may be the same or different from each other. When compound (1b) has a plurality of R ^y , R ^y may be the same or different from each other.

When the compound (1a) has a plurality of ^Rx , ^Rx may be the same or different from each other. When the compound (1b) has a plurality of ^Rx , ^Rx may be the same or different from each other.

R ^x is preferably SF ₅ . In addition, R ^x may be a hydrocarbon group having 1 to 20 carbon atoms in which one or more hydrogen atoms are substituted with SF ₅ , and the hydrocarbon group may be selected from the same groups as the above-mentioned R ^y , and examples thereof include aliphatic hydrocarbon groups, aromatic hydrocarbon groups, etc. The base of the ring (including the base of the aromatic ring). The number of SF ₅ substituted in each hydrocarbon group having 1 to 20 carbon atoms is preferably 1 to 6, more preferably 1 to 3, particularly preferably 1. The hydrocarbon group is preferably a hydrocarbon group which does not have a substituent other than SF ₅ .

R ^x is preferably an aromatic ring-containing group in which one or more hydrogen atoms are substituted with SF ₅ , and more preferably an aromatic hydrocarbon group in which one or more hydrogen atoms are substituted with SF ₅ . In the aromatic ring-containing group in which one or more hydrogen atoms are substituted with SF ₅ , it is preferable to bond at the meta-position and/or the para-position with respect to the bond of the aromatic ring-containing group. SF ₅ , more preferably SF ₅ for para-bonding. As such an aromatic ring-containing group, the group represented by the following formula (Ar-mSF ₅ ) and formula (Ar-pSF ₅ ) may, for example, be mentioned.

As m, the integer of 1-16 is preferable, the integer of 2-12 is more preferable, the integer of 3-9 is still more preferable, the integer of 4-8 is still more preferable, and 4 is especially preferable. The total of n and m is preferably an integer of 1 to 16, more preferably an integer of 2 to 12, still more preferably an integer of 3 to 9, still more preferably an integer of 4 to 8, particularly preferably 4.

M is a metal element which may have a substituent, or a semimetal element which may have a substituent.

As a metal element which may have a substituent, a metal element and a metal element which has a substituent are mentioned. As a metal element, an alkali metal, an alkaline earth metal, a transition metal, a lanthanoid metal, an actinide metal element, etc. are mentioned. Specific examples of the metal element include lithium, sodium, potassium, magnesium, calcium, scandium, yttrium, titanium, zirconium, chromium, manganese, molybdenum, iron, ruthenium, cobalt, rhodium, nickel, palladium, nickel, copper, Zinc, aluminum, gallium, indium, tin, lanthanum, uranium, etc. Among them, copper, zinc, and aluminum are preferred.

The substituent may, for example, be an oxygen atom, a hydroxyl group, a halogen atom, a phosphoric acid group, a sulfonic acid group, a carboxylic acid group, a hydrocarbon group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.

Specific examples of the metal element having a substituent include lithium oxide, magnesium oxide, calcium oxide, titanium oxide, chromium oxide, manganese oxide, molybdenum oxide, iron oxide, ruthenium oxide, copper oxide, zinc oxide, aluminum oxide, Metal oxides such as gallium oxide, lanthanum oxide, uranium oxide; Metal hydroxides such as aluminum hydroxide, indium hydroxide, thallium hydroxide; Copper fluoride, zinc fluoride, aluminum fluoride, copper chloride, zinc chloride, Metal halides such as aluminum chloride; Phosphated metals such as copper phosphate, zinc phosphate, aluminum phosphate; Sulfonated metals such as copper sulfonate, zinc sulfonate, aluminum sulfonate; Acidified metal; represented by -Al(R ^z )- and R ^z is an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms, such as hydrocarbon-containing metals such as hydrocarbon-containing aluminum.

As a semi-metal element which may have a substituent, a semi-metal element and a semi-metal element which has a substituent are mentioned. Semimetallic elements are elements with properties intermediate between metals and nonmetals. As a semimetal element, boron, silicon, arsenic, germanium, lead, etc. are mentioned. As a substituent, the same group as the substituent of the said metal element is mentioned.

Specific examples of semi-metal elements having substituents include semi-metal oxides such as boron oxide, silicon oxide, arsenic oxide, germanium oxide, and lead oxide; and semi-metal hydrogen such as boron hydroxide, silicon hydroxide, and lead hydroxide. Oxides; Semi-metal halides such as boron fluoride, silicon fluoride, lead fluoride, boron chloride, silicon chloride, lead chloride; Phosphate semi-metals such as boron phosphate, silicon phosphate, lead phosphate; Boron sulfonate, Sulfonated semimetals such as silicon sulfonate and lead sulfonate; Carboxylated semimetals such as boron carboxylate, silicon carboxylate, lead carboxylate, etc.; represented by -Si(R ^z1 )(R ^z2 )- and R ^z1 and R ^z2 are respectively It is independently a hydrocarbon-containing semimetal such as an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, such as hydrocarbon-containing silicon.

The compound (1a) is preferably a compound represented by the following formula (2a) (hereinafter, sometimes referred to as compound (2a)). In addition, the compound (1b) is preferably a compound represented by the following formula (2b) (hereinafter, sometimes referred to as compound (2b)).

[hua 7]

[式(2a)、式(2b)中， R^x 、R^y 、M分別表示與上文所述相同之含義， o表示1～4之整數， p表示0～3之整數]。[hua 8]

[In formula (2a) and formula (2b), R ^x , R ^y , and M respectively have the same meanings as described above, o represents an integer of 1 to 4, and p represents an integer of 0 to 3].

In the formula (2a) and the formula (2b), o is preferably an integer of 1 to 4, more preferably an integer of 1 to 2, and particularly preferably 1. As p, an integer of 0-3 is preferable, an integer of 0-1 is more preferable, and 0 is especially preferable. The sum of o and p is preferably an integer of 1 to 4, more preferably an integer of 1 to 2, and particularly preferably 1.

The compound (1a) is preferably a compound represented by the following formula (3a). Further, the compound (1b) is preferably a compound represented by the following formula (3b).

[Chemical 9]

[Chemical 10]

[In formula (3a) and formula (3b), independently at least one of R ^a to R ^d is the same group as the above R ^x , and the others are the same group as the hydrogen atom or the above R ^y ; M represents the have the same meaning as mentioned above].

Preferably, among R ^a to R ^d , R ^a or R ^d are each independently the same group as the above R ^x and the other are the same group as the above R ^y or a hydrogen atom, or R ^b or R ^c are each independently is the same group as the above-mentioned R ^x and the other is the same group as the above-mentioned R ^y or a hydrogen atom. More preferably, among R ^a to R ^d , R ^b or R ^c are independently the same group as the above-mentioned R ^x and the others are the same group or hydrogen atom as the above-mentioned R ^y , and more preferably, R ^b or R ^c is each independently the same group as the above-mentioned R ^x and the other is a hydrogen atom, and more preferably, R ^b or R ^c is each independently SF ₅ and the other is a hydrogen atom.

More preferably, among R ^a to R ^d , R ^a or R ^d are each independently the same group as the above-mentioned R ^x and the other are the same group as the above-mentioned R ^y or a hydrogen atom, and more preferably, R ^a or R ^d is each independently the same group as the above-mentioned R ^x and the other is a hydrogen atom, and more preferably, R ^a or R ^d are each independently an aromatic ring-containing group in which one or more hydrogen atoms are substituted with SF ₅ . and the others are hydrogen atoms.

In the aromatic ring-containing group in which one or more hydrogen atoms are substituted with SF ₅ , it is preferable to bond at the meta-position and/or the para-position with respect to the bond of the aromatic ring-containing group. SF ₅ , more preferably SF ₅ for para-bonding. As such an aromatic ring-containing group, the group represented by the following formula (Ar-mSF ₅ ) and formula (Ar-pSF ₅ ) may, for example, be mentioned.

The compound (1a) and the compound (1b) are preferably compounds (a1) to (a20) represented by the following Table 1 and the following formula (4a), and preferably represented by the following Table 2 and the following formula (4b). The compounds (b1) to (b20).

[Chemical 11]

[Table 1] compound R ^x M a1 _SF5 Zn a2 CSF ₅ Zn a3 CCSF ₅ Zn a4 Ar- _mSF5 Zn a5 Ar- _pSF5 Zn a6 _SF5 Cu a7 CSF ₅ Cu a8 CCSF ₅ Cu a9 Ar- _mSF5 Cu a10 Ar- _pSF5 Cu a11 _SF5 Al a12 CSF ₅ Al a13 CCSF ₅ Al a14 Ar- _mSF5 Al a15 Ar- _pSF5 Al a16 _SF5 - a17 CSF ₅ - a18 CCSF ₅ - a19 Ar- _mSF5 - a20 Ar- _pSF5 -

[Chemical 12]

[Table 2] compound ^Rx M b1 _SF5 Zn b2 CSF ₅ Zn b3 CCSF ₅ Zn b4 Ar- _mSF5 Zn b5 Ar- _pSF5 Zn b6 _SF5 Cu b7 CSF ₅ Cu b8 CCSF ₅ Cu b9 Ar- _mSF5 Cu b10 Ar- _pSF5 Cu b11 _SF5 Al b12 CSF ₅ Al b13 CCSF ₅ Al b14 Ar- _mSF5 Al b15 Ar- _pSF5 Al b16 _SF5 - b17 CSF ₅ - b18 CCSF ₅ - b19 Ar- _mSF5 - b20 Ar- _pSF5 -

In Formula 4a and Formula 4b, R ^x and M have the same meanings as described above, respectively. In Tables 1 and 2, SF ₅ , CSF ₅ , CCSF ₅ , Ar-mSF ₅ , and Ar-pSF ₅ represent the following formulae (SF ₅ ), formula (CSF ₅ ), formula (CCSF ₅ ), formula (Ar- mSF ₅ ), a group represented by the formula (Ar-pSF ₅ ).

[Chemical 13]

As the compound (1a) and the compound (1b), the compounds (a1) to (a15) and the compounds (b1) to (b15) are more preferred, the compounds (a1) to (a15) are still more preferred, and the compounds are still more preferred. (a1), (a4) to (a6), (a9) to (a11), (a14), (a15), particularly preferably compounds (a1), (a6) and (a11).

The compound (1a) and the compound (1b) are more preferably the compounds (b1) to (b15), and more preferably the compounds (b4), (b5), (b9), (b10), (b14), ( b15), particularly preferably compounds (b5), (b10) and (b15).

The production method of compound (1a) and compound (1b) is not particularly limited, and can be produced by referring to the examples described in Japanese Patent No. 6206977 .

The compound (1a) and the compound (1b) are preferably organic solvents having a solubility parameter (SP value) of less than 11.0 (cal/cm ³ ) ^1/2 , such as propylene glycol monomethyl ether acetate. In addition, soluble and poorly soluble can be evaluated by the following method.

0.1 g of the compound was put into a 20 mL sample vial, and then an organic solvent was put into it using a 10 mL full pipette, and the lid was closed and sonicated for 3 minutes. The obtained liquid was left to stand for 60 minutes in a water bath at 23°C. 5 mL of the supernatant was filtered through a 5 μm membrane filter made of PTFE (Polytetrafluoroethylene), and further filtered through a 0.25 μm membrane filter to remove insoluble matter. The absorbance spectrum of the obtained filtrate was measured with an ultraviolet-visible spectrophotometer (for example, UV-2500PC manufactured by Shimadzu Corporation) using a 1 cm colorimetric cell, and the absorbance (abs) at the maximum absorption wavelength of the compound was obtained. At this time, if the above-mentioned absorbance (abs) is less than 40% of the upper limit of the measurement (in the case of UV-2500PC manufactured by Shimadzu Corporation, the absorbance (abs) is less than 2), it is evaluated as poorly soluble. If it is more than 40% of the limit value, it is evaluated as soluble.

The content of compound (1a) and compound (1b) is preferably 40 to 100% by mass, more preferably 60 to 90% by mass, and still more preferably 70 to 80% by mass in the total amount of the colorant (A). quality%. The content rate of the compound (1a) and the compound (1b) refers to the sum of the content rates of the compound (1a) and the compound (1b) when the colored resin composition contains both the compound (1a) and the compound (1b).

The content of the compound (1a) is preferably 40 to 100 mass %, more preferably 60 to 90 mass %, and still more preferably 70 to 80 mass % in the total amount of the colorant (A).

The content of the compound (1a) and the compound (1b) is preferably 5 to 200 parts by mass, more preferably 10 to 100 parts by mass, and still more preferably 100 parts by mass of the resin (B) (solid content). 12 to 50 parts by mass. The content of the compound (1a) and the compound (1b) refers to the total amount of the compound (1a) and the compound (1b) when the colored resin composition contains both the compound (1a) and the compound (1b).

<Colorant (A1)> The colored resin composition of the present invention may also contain dyes (hereinafter, sometimes referred to as dyes (A1-1)) and/or pigments (hereinafter, sometimes referred to as pigments) other than compound (1a) and compound (1b). A1-2)) as a colorant (A) (hereinafter, the dye (A1-1) and the pigment (A1-2) may be collectively referred to as a colorant (A1)). These can be used alone or in combination of two or more.

染料、噻唑染料、㗁𠯤染料、蒽醌染料、萘醌染料、醌亞胺染料、次甲基染料、甲亞胺染料、方酸鎓染料、吖啶染料、苯乙烯基染料、香豆素染料、喹啉染料、硝基染料及酞菁染料等。As the dye (A1-1), as long as the compound (1a) and the compound (1b) are not included, a known dye can be used without particular limitation, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of the dye include compounds classified under the dye category in the Dye Index (published by The Society of Dyers and Colourists), or known dyes described in Dyeing Note (a dyeing company). Moreover, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, 𠮿

Dyes, thiazole dyes, 㗁𠯤 dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azimuth imine dyes, squaraine dyes, acridine dyes, styryl dyes, coumarin dyes , quinoline dyes, nitro dyes and phthalocyanine dyes.

It does not specifically limit as a pigment (A1-2), A well-known pigment can be used, for example, the pigment under the pigment classification in a dye index (published by The Society of Dyers and Colourists) can be mentioned. As the pigment under the pigment classification, for example, CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231 and other yellow pigments; C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments; CI Pigment Red 9, 97, 105, 122, 144, 149, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268 , 269, 273 and other red pigments; C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 and other blue pigments; C.I. Pigment Violet 1, 19, 23, 32, 36, 38 and other purple pigments; C.I. Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments; C.I. Pigment Brown 23, 25 and other brown pigments; C.I. Pigment Black 1, 7 and other black pigments, etc.

The colorant (A) preferably contains at least one pigment selected from the group consisting of a yellow pigment and a green pigment. In particular, it is preferable to contain C.I. Pigment Yellow 138, 139, 185, 231, and C.I. Pigment Green 7, 36, 58, 59, 62, and 63.

The content of the pigment (A1-2) is preferably 1 to 50% by mass, more preferably 5 to 40% by mass, and still more preferably 10 to 30% by mass in the total amount of the colorant (A).

The content of the yellow pigment or the green pigment is preferably 50 to 100% by mass, more preferably 70 to 100% by mass, still more preferably 90 to 100% by mass, and particularly preferably 100% by mass in the total amount of the pigment. %. In addition, in the case of including both the yellow pigment and the green pigment, the said content rate means the total content rate of the yellow pigment and the green pigment.

Pigment (A1-2) can also be subjected to rosin treatment, surface treatment using derivatives introduced with acidic groups or basic groups, etc., grafting treatment of the surface of the pigment with polymer compounds, etc., and sulfuric acid micronization, etc., as required. Micronization treatment, cleaning treatment with organic solvent or water for removing impurities, removal treatment with ion exchange method for ionic impurities, etc. The particle size of the pigment is preferably approximately uniform. The pigment dispersion liquid in the state of being uniformly dispersed in the dispersing agent solution can be obtained by carrying out the dispersion treatment including the dispersing agent in the pigment. In the case of using a plurality of pigments, the dispersion treatment may be performed independently, or the dispersion treatment may be performed after mixing a plurality of pigments. Moreover, after mixing a pigment with the said compound (1a) and a compound (1b), a dispersion process may be performed.

As a dispersing agent, a surfactant etc. are mentioned, for example, Any of a cationic surfactant, an anionic surfactant, a nonionic surfactant, and an amphoteric surfactant may be sufficient. Specifically, surfactants, such as a polyester type, a polyamine type, and an acrylic type, etc. are mentioned. These dispersants may be used alone or in combination of two or more. As a dispersant, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered) trademark) (manufactured by BASF Corporation), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno (stock)), Disperbyk (registered trademark) (manufactured by BYK-Chemie (stock)) and BYK (registered trademark) (BYK-Chemie (stock) ) manufacture) etc. As a dispersant, resin (B) described below can also be used.

In the case of using a dispersant, the amount of the dispersant (solid content) used is based on 100 parts by mass of the pigment, usually 10 to 200 parts by mass, preferably 15 to 180 parts by mass, more preferably 20 to 160 parts by mass parts by mass. If the amount of the dispersant used is within the above-mentioned range, a more uniformly dispersed pigment dispersion liquid tends to be obtained.

When a dispersant is used, the amount of the dispersant (solid content) used is preferably 1-500 parts by mass, more preferably 5-300 parts by mass relative to 100 parts by mass of compound (1a) and compound (1b) The mass part is more preferably 10 to 200 mass parts, still more preferably 15 to 180 mass parts. If the usage-amount of this dispersing agent is in the said range, there exists a tendency for the coloring dispersion liquid of a more uniform dispersion state to be obtained. The compound (1a) and 100 parts by mass of the compound (1b), when the colored resin composition contains both the compound (1a) and the compound (1b), refers to the total amount of those and the like.

In the case of using a dispersant, the amount of the dispersant (solid content) used is based on 100 parts by mass of the pigment, usually 10 to 200 parts by mass, preferably 15 to 180 parts by mass, more preferably 20 to 160 parts by mass parts by mass. If the amount of the dispersant used is within the above-mentioned range, a more uniformly dispersed pigment dispersion liquid tends to be obtained.

The content rate of the colorant (A1) is preferably 1 to 50% by mass, more preferably 5 to 40% by mass, and still more preferably 10 to 30% by mass in the total amount of the colorant (A).

The content rate of the colorant (A) is preferably 1 to 70% by mass, more preferably 5 to 60% by mass, and still more preferably 10 to 60% by mass with respect to the total amount of the solid content of the colored resin composition. %, more preferably 12 to 55 mass %. If the content rate of the colorant (A) is within the above range, the color density when a color filter is made is sufficient, and the composition can contain a desired amount of the resin (B), so that a sufficient mechanical strength can be formed. pattern, so it is better.

Here, the "total amount of solid content" in this specification refers to the amount obtained by dividing the total amount of the colored resin composition by the content of the organic solvent. The total amount of solid content and the content of each component with respect to the total solid content can be measured, for example, by a known analytical method such as liquid chromatography or gas chromatography.

<Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. As resin (B), the following resin [K1] - [K6] etc. are mentioned. Resin [K1]: has a structural unit derived from at least one (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides, and has a A copolymer of a structural unit of a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond monomer (b) (hereinafter sometimes referred to as "(b)"); Resin [K2]: having a structural unit derived from (a), a structural unit derived from (b), and a monomer derived from (c) copolymerizable with (a) (however, with (a) and (b) ) different) (hereinafter sometimes referred to as "(c)") structural units; Resin [K3]: a copolymer having a structural unit derived from (a) and a structural unit derived from (c); Resin [K4]: a copolymer having a structural unit obtained by adding (b) to a structural unit derived from (a), and a structural unit derived from (c); Resin [K5]: a copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b), and a structural unit derived from (c); Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a polyvalent carboxylic acid and/or a carboxylic acid anhydride, and a structural unit derived from (c) .

Specific examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-vinyl benzoic acid, m-vinyl benzoic acid, and p-vinyl benzoic acid; Maleic acid, fumaric acid, methyl maleic acid, methyl fumaric acid, methylenesuccinic acid, 3-vinylphthalic acid, 4-vinylphthalic acid Dicarboxylic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl tetrahydrophthalate, 1,4-cyclohexene Unsaturated dicarboxylic acids such as dicarboxylic acids; Methyl-5-noralkene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-Carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[ 2.2.1] Hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene and other bicyclic unsaturated compounds containing carboxyl groups; Maleic anhydride, methylmaleic anhydride, methylenesuccinic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetra Hydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2- Unsaturated dicarboxylic acid anhydrides such as alkene anhydride; Divalent or higher polycarboxylic acids such as mono[2-(meth)acryloyloxyethyl] succinate, mono[2-(meth)acrylooxyethyl] phthalate, etc. Saturated mono[(meth)acryloyloxyalkyl]esters; Unsaturated acrylates and the like that contain a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Among them, acrylic acid, methacrylic acid, etc. are preferable in terms of the copolymerization reactivity or the solubility of the obtained resin in an alkaline aqueous solution.

(b), for example, refers to a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated Bonded polymeric compounds. (b) It is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group. In addition, in this specification, "(meth)acrylic acid" represents at least one kind selected from the group which consists of acrylic acid and methacrylic acid. Notation such as "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

As (b), for example, a monomer (b1) having an oxirane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond, A saturated bond monomer (b2) (hereinafter sometimes referred to as "(b2)"), a monomer (b3) having a tetrahydrofuran group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), and the like.

As (b1), for example, a monomer (b1-1) having a structure after epoxidation of a linear or branched aliphatic unsaturated hydrocarbon (hereinafter sometimes referred to as "(b1-1)" may be mentioned. ), a monomer (b1-2) having a structure after epoxidation of an alicyclic unsaturated hydrocarbon (hereinafter sometimes referred to as "(b1-2)").

As (b1-1), glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, and glycidyl vinyl ether may, for example, be mentioned. , o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinyl glycidyl ether Benzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidoxymethyl)styrene, 2,4-bis(glycidoxymethyl)benzene Ethylene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl)benzene Ethylene, 2,3,5-Tris(glycidoxymethyl)styrene, 2,3,6-Tris(glycidoxymethyl)styrene, 3,4,5-Tris(glycidoxymethyl)styrene methyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, and the like.

As (b1-2), vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000; manufactured by Daicel Co., Ltd.), (meth)acrylic acid can be mentioned. 3,4-Epoxycyclohexylmethyl ester (for example, Cyclomer A400; manufactured by Daicel (stock)), 3,4-epoxycyclohexylmethyl (meth)acrylate (for example, Cyclomer M100; manufactured by Daicel (stock)) , the compound represented by the formula (BI) and the compound represented by the formula (BII), etc.

[式(BI)及式(BII)中， R^e 及R^f 表示氫原子或碳數1～4之烷基，該烷基所包含之氫原子亦可被取代為羥基； X^e 及X^f 表示單鍵、*-R^g -、*-R^g -O-、*-R^g -S-或*-R^g -NH-； R^g 表示碳數1～6之烷二基； *表示與O之鍵結鍵]。[Chemical 14]

[In formula (BI) and formula (BII), R ^e and R ^f represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may also be substituted with a hydroxyl group; X ^e and X ^f Represents a single bond, *-R ^g -, *-R ^g -O-, *-R ^g -S- or *-R ^g -NH-; R ^g represents alkanediyl with 1 to 6 carbon atoms; * represents and The key of O].

As the alkyl group having 1 to 4 carbon atoms, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, etc. may be mentioned. Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxypropyl, Hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl and the like. Preferable examples of ^Re and R ^f include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferable examples include a hydrogen atom and a methyl group.

As the alkanediyl group, a methylene group, an ethylidene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, and a pentane-1,5-diyl group may, for example, be mentioned. -diyl, hexane-1,6-diyl, etc. Preferred examples of X ^e and X ^f include single bond, methylene group, ethylidene group, *-CH ₂ -O- and *-CH ₂ CH ₂ -O-, and more preferred examples include single bond , *-CH ₂ CH ₂ -O- (* represents a bond with O).

As a compound represented by Formula (BI), the compound etc. which are represented by any one of Formula (BI-1) - Formula (BI-15) are mentioned. Among them, formula (BI-1), formula (BI-3), formula (BII-5), formula (BI-7), formula (BI-9) or formula (BI-11) to formula (BI) are preferred The compound represented by -15) is more preferably a compound represented by formula (BI-1), formula (BI-7), formula (BI-9) or formula (BI-15).

[Chemical 15]

[Chemical 16]

As a compound represented by Formula (BII), the compound etc. which are represented by any one of Formula (BII-1) - Formula (BII-15) are mentioned. Among them, formula (BII-1), formula (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) or formula (BII-11) to formula (BII) are preferred The compound represented by -15) is more preferably a compound represented by formula (BII-1), formula (BII-7), formula (BII-9) or formula (BII-15).

[Chemical 17]

[Chemical 18]

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. When the compound represented by the formula (BI) and the compound represented by the formula (BII) are used together, their content ratio (the compound represented by the formula (BI): the compound represented by the formula (BII)) is in moles The ratio is preferably 5:95 to 95:5, more preferably 20:80 to 80:20.

As (b2), a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. As (b2), 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3- Ethyl-3-methacryloyloxymethyl oxetane, 3-ethyl-3-propenyloxymethyl oxetane, 3-methyl-3-methacryloyloxy Ethyl ethyl oxetane, 3-methyl-3-propenyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3 -Ethyl-3-propenyloxyethyl oxetane, etc.

As (b3), a monomer having a tetrahydrofuran group and a (meth)acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

As (b), in order to further improve the reliability of the heat resistance, chemical resistance, etc. of the obtained color filter, (b1) is preferable. Furthermore, in order to make the storage stability of a colored resin composition excellent, (b1-2) is more preferable.

As (c), for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, 2-butyl (meth)acrylate, tertiary (meth)acrylate Tributyl, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, ring (meth)acrylate Amyl ester, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate , (meth)acrylates (cf-1) that do not have polycyclic hydrocarbon rings, such as naphthyl (meth)acrylate, benzyl (meth)acrylate, etc. (hereinafter sometimes referred to as "(cf-1)"); (meth)acrylate tricyclo[ ^5.2.1.02,6 ]decane-8-yl ester (commonly known as "(meth)acrylate dicyclopentyl ester" in this technical field; also, sometimes referred to as "(meth)acrylate tricyclodecyl ester"), (meth)acrylate tricyclo[5.2.1.0 ^2,6 ]decen-8-yl ester (commonly known as "(meth)acrylate in this technical field" Dicyclopentenyl acrylate”), dicyclopentyloxyethyl (meth)acrylate, iso(meth)acrylate, adamantyl (meth)acrylate, etc. have polycyclic hydrocarbon rings (meth)acrylates (cf-2) (hereinafter sometimes referred to as "(cf-2)"); 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, etc. (Meth)acrylates containing hydroxyl groups; Diethyl maleate, diethyl fumarate, diethyl methylene succinate and other dicarboxylic acid diesters; Bicyclo[2.2.1 ]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene 2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[ 2.2.1] Hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxy (Hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxy Bicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2- alkene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxy ylcarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene , 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5,6 -Bicyclic unsaturated compounds such as bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; N-phenylmaleimide, N-cyclohexylmaleimide , N-benzyl maleimide, N-butadiimide-3-maleimide benzoate, N-butadiimide-4-butene Diimidate butyrate, N-butadiimido-6-maleimidohexanoate, N-butadiimino-3-maleimidopropionic acid Esters, N-(9-acridinyl)maleimide and other dicarbonylimide derivatives; Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, Vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, iso Pentadiene, 2,3-dimethyl-1,3-butadiene, etc. Among them, (meth)acrylates are preferred.

In resin [K1], with respect to the respective ratios of the structural units derived from (a) and (b), among all the structural units constituting resin [K1], Preferably, Structural units derived from (a): 2 to 60 mol% Structural units derived from (b): 40-98 mol%, Better yet, Structural units derived from (a): 10-50 mol% Structural units derived from (b): 50-90 mol%. If the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter tend to be excellent.

For resin [K1], for example, reference can be made to the method described in the document "Experimental Methods for Polymer Synthesis" (written by Takashi Otsu, Chemical Doujin Publishing House, 1st edition, 1st printing, issued on March 1, 1972). and the citations described in this document to manufacture.

Specifically, a method can be exemplified by a method in which specific amounts of (a) and (b), a polymerization initiator, a solvent, and the like are added to a reaction vessel, for example, by replacing oxygen with nitrogen, and the atmosphere is deoxidized, and stirring is performed. Heat and keep warm. In addition, the polymerization initiator, solvent, etc. used here are not specifically limited, A common user in this field can be used. For example, as the polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic Peroxide (benzyl peroxide, 3-butyl 2-ethylhexanoate peroxide, etc.), as a solvent, as long as it is a solvent that can dissolve each monomer, it can be exemplified below as the coloring of the present invention The organic solvent (C) of the resin composition is the solvent described in the description, and the like.

In addition, the obtained copolymer can use the solution after reaction as it is, can also use the solution after concentration or dilution, and can also use the thing extracted in the form of solid (powder) by methods, such as reprecipitation. In particular, by using the solvent contained in the colored resin composition of the present invention as the solvent during the polymerization, the solution after the reaction can be directly used in the preparation of the colored resin composition of the present invention, so that the process of the present invention can be simplified. The manufacturing steps of the colored resin composition.

In resin [K2], regarding the ratio of each of the structural units derived from (a), (b), and (c), among all the structural units constituting resin [K2], Preferably, Structural units derived from (a): 2 to 45 mol% Structural units derived from (b): 2 to 95 mol% Structural units derived from (c): 1-65 mol%, Better yet, Structural units derived from (a): 5-40 mol% Structural units derived from (b): 5-80 mol% Structural units derived from (c): 5-60 mol %. If the ratio of the structural unit of the resin [K2] is within the above-mentioned range, the storage stability of the colored resin composition, the developability at the time of forming the colored pattern, and the solvent resistance, heat resistance and mechanical resistance of the obtained color filter Strength showed an excellent trend.

Resin [K2] can be manufactured similarly to the method described as the manufacturing method of resin [K1], for example.

In resin [K3], regarding the ratio of each of the structural units derived from (a) and (c), among all the structural units constituting resin [K3], Preferably, Structural units derived from (a): 2 to 60 mol% Structural units derived from (c): 40-98 mol%, Better yet, Structural units derived from (a): 10-50 mol% Structural units derived from (c): 50-90 mol%. Resin [K3] can be manufactured similarly to the method described as the manufacturing method of resin [K1], for example.

Resin [K4] can be obtained by obtaining a copolymer of (a) and (c), and combining the cyclic ether with 2 to 4 carbon atoms contained in (b) and the carboxylic acid and/or carboxylic acid anhydride contained in (a) Manufactured by addition. First, the copolymer of (a) and (c) is produced similarly to the method described as the production method of resin [K1]. In this case, the ratio of each of the structural units derived from (a), (c) is preferably the same ratio as exemplified for the resin [K3].

Next, a part of the carboxylic acid and/or carboxylic acid anhydride derived from (a) in the above-mentioned copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms contained in (b). After the copolymer of (a) and (c) is produced, the nitrogen atmosphere in the flask is replaced with an air atmosphere, and the reaction catalyst of (b), carboxylic acid or carboxylic anhydride and cyclic ether (such as tri( Resin [K4] can be produced by reacting, for example, dimethylaminomethyl)phenol, etc., and a polymerization inhibitor (for example, hydroquinone, etc.) at 60 to 130° C. for 1 to 10 hours. About the usage-amount of (b), 5-80 mol is preferable with respect to 100 mol of (a), and 10-75 mol is more preferable. By setting it as this range, the balance of the storage stability of a colored resin composition, the developability at the time of pattern formation, and the solvent resistance, heat resistance, mechanical strength, and sensitivity of the obtained pattern tends to become favorable. Since the reactivity of the cyclic ether is high, it is difficult for the unreacted (b) to remain. Therefore, the (b) used as the resin [K4] is preferably (b1), more preferably (b1-1). About the usage-amount of the said reaction catalyst, 0.001-5 mass parts is preferable with respect to 100 mass parts of total amounts of (a), (b) and (c). About the usage-amount of the said polymerization inhibitor, 0.001-5 mass parts is preferable with respect to 100 mass parts of total amounts of (a), (b) and (c). The reaction conditions such as the addition method, the reaction temperature, and the time can be appropriately adjusted in consideration of the production facility and the calorific value of the polymerization. In addition, similarly to the polymerization conditions, the method of addition and the reaction temperature can be appropriately adjusted in consideration of the production facility and the calorific value generated by the polymerization.

About resin [K5], as a first stage, the copolymer of (b) and (c) was obtained similarly to the manufacturing method of the said resin [K1]. Similar to the production method of the above-mentioned resin [K1], the obtained copolymer can be directly used as a solution after the reaction, can also be used as a concentrated or diluted solution, and can also be used as a solid (powder) by a method such as reprecipitation. form taker. About the ratio of the structural unit derived from (b) and (c), with respect to the total number of moles of all the structural units constituting the above-mentioned copolymer, respectively, Preferably, Structural units derived from (b): 5-95 mol% Structural units derived from (c): 5-95 mol%, Better yet, Structural units derived from (b): 10-90 mol% Structural units derived from (c): 10-90 mol%.

Furthermore, under the same conditions as the production method of resin [K4], the cyclic ether derived from (b) and the carboxyl group (a) of the copolymer of (b) and (c) can be obtained The acid or carboxylic acid anhydride reacts to obtain resin [K5]. The usage-amount of (a) which reacts with the said copolymer is preferably 5-100 mol with respect to 100 mol of (b). Since the reactivity of the cyclic ether is high, it is difficult for the unreacted (b) to remain. Therefore, the (b) used as the resin [K5] is preferably (b1), and more preferably (b1-1).

Resin [K6] is resin which made resin [K5] and polyhydric carboxylic acid and/or carboxylic anhydride react further. The hydroxyl group generated by the reaction of the cyclic ether derived from (b) and the carboxylic acid or carboxylic acid anhydride derived from (a) is further reacted with a polyvalent carboxylic acid and/or a carboxylic acid anhydride. As a polyhydric carboxylic acid, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, triphenylamine, etc. are mentioned. Examples of the carboxylic acid anhydride include succinic anhydride, maleic anhydride, methylmaleic anhydride, methylenesuccinic anhydride, 3-vinylphthalic anhydride, and 4-vinylphthalic anhydride. Acid anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dihydrophthalic anhydride Carboxy bicyclo[2.2.1]hept-2-ene anhydride, etc. The usage-amount of polyhydric carboxylic acid and/or carboxylic anhydride is preferably 0.05-1 mol, more preferably 0.1-0.5 mol, relative to 1 mol of the usage-amount of (a). That is, the resin [K6] preferably also has a polycarboxylic acid added to the hydroxyl group not generated by the reaction of the cyclic ether derived from (b) and the carboxylic acid or carboxylic acid anhydride derived from (a), and / or a carboxylic acid anhydride, it is a structural unit obtained by adding (a) to a structural unit derived from (b).

The resin (B) is preferably a resin (resin [K4], resin [K5] or resin [K6]) having a structural unit containing an ethylenically unsaturated bond in a side chain, more preferably a resin having a side chain containing ( Resins with structural units of meth)acryloyl groups.

Examples of the resin having a structural unit having a (meth)acryloyl group in its side chain include resin [K4], resin [K5], or resin [K6], and the resin [K4] is shrunk using (meth)acrylic acid. Glycerides, 3,4-epoxycyclohexylmethyl (meth)acrylate, 3-methyl-3-methacrylooxymethyl oxetane, tetrahydrofurfuryl acrylate, etc. have (methyl) ) Acryloyl monomer (ba) (hereinafter sometimes referred to as "(ba)") as (b), the above-mentioned resin [K5] uses acrylic acid, methacrylic acid, succinic acid mono[2-(methyl) ) Monomer (aa) (hereinafter sometimes referred to as "(aa)") having a (meth)acryloyl group, such as acryloxyethyl] ester, as (a), the above-mentioned resin [K6] uses (aa) ) as (a). As resin which has a structural unit containing a (meth)acryloyl group in a side chain, it is preferable to contain the resin [K6] which used (aa) as (a).

As a resin having a structural unit containing a (meth)acryloyl group in a side chain, it is more preferable to include a resin [K6] that contains a (meth)acryloyl group in a side chain and which is derived from a polycarboxylic acid and/or The structural unit of the carboxylic acid group of the carboxylic acid anhydride (the structural unit obtained by adding (aa) to the structural unit derived from (b), and further adding a polycarboxylic acid and/or carboxylic acid anhydride), a side chain containing (methyl ) acryl group and does not contain a structural unit derived from a carboxylic acid group derived from a polycarboxylic acid and/or a carboxylic acid anhydride (a structural unit obtained by adding (aa) to a structural unit derived from (b)), and derived from ( c) Structural unit; further preferably resin [K6] having a structural unit containing a (meth)acryloyl group in a side chain and a carboxylic acid group derived from a polycarboxylic acid and/or a carboxylic acid anhydride (in (aa) is added to the structural unit derived from (b), and the structural unit obtained by further adding a polycarboxylic acid and/or carboxylic acid anhydride), the side chain contains a (meth)acryloyl group and does not contain a polycarboxylic acid derived from Structural unit of carboxylic acid group of acid and/or carboxylic acid anhydride (structural unit obtained by adding (aa) to structural unit derived from (b)), and derived from (cf-1) and/or (cf-2 ); particularly preferably a resin [K6] comprising a structural unit having a (meth)acryloyl group in its side chain and a carboxylic acid group derived from a polycarboxylic acid and/or a carboxylic acid anhydride (in the case of (a) is added to the structural unit of (b), and the structural unit obtained by further adding polycarboxylic acid and/or carboxylic acid anhydride), the side chain contains (meth)acryloyl group and does not contain polycarboxylic acid and /or the structural unit of the carboxylic acid group of the carboxylic acid anhydride (the structural unit obtained by adding (aa) to the structural unit derived from (b)), and the structural unit derived from (cf-1) and (cf-2) .

Moreover, as resin (B), in order to improve the residual film ratio, it is preferable to use resins other than resins (resin [K4], resin [K5], or resin [K6]) having a structural unit containing an ethylenically unsaturated bond in the side chain. , which further contains resin [K1].

The weight average molecular weight in terms of polystyrene of the resin (B) is preferably 3,000 to 100,000, more preferably 4,000 to 50,000, and still more preferably 5,000 to 30,000. When the molecular weight is within the above range, the hardness of the color filter increases, the residual film rate increases, the solubility of the unexposed portion in the developing solution is good, and the resolution of the colored pattern tends to increase.

The degree of dispersion [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

The acid value of the resin (B) is preferably 20 to 170 mg-KOH/g, more preferably 25 to 150 mg-KOH/g, still more preferably 30 to 130 mg-KOH/g in terms of solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 7 to 65 mass %, more preferably 13 to 60 mass % with respect to the total amount of the solid content of the colored resin composition (especially the colored curable resin composition). , and more preferably 17 to 55 mass %. When the content rate of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film ratio of the colored pattern tend to be improved. The content of the resin (B) is preferably 40 to 98% by mass, more preferably 50 to 95% by mass, and still more preferably the total amount of the solid content of the colorant (A) and the resin (B). It is 60-92 mass %, More preferably, it is 70-90 mass %.

<Organic solvent (C)> The colored resin composition may contain an organic solvent (hereinafter, sometimes referred to as an organic solvent (C)). The organic solvent (C) is not particularly limited, and an organic solvent generally used in this field can be used. For example, ester solvent (solvent containing -COO- and not containing -O- in the molecule), ether solvent (solvent containing -O- and not containing -COO- in the molecule), ether ester solvent (containing - Solvent of COO- and -O-), ketone solvent (solvent containing -CO- and not containing -COO- in the molecule), alcohol solvent (containing OH in the molecule and not containing -O-, -CO- and -COO- solvent), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, and isoamyl acetate. , Butyl Propionate, Isopropyl Butyrate, Methyl Butyrate, Butyrate, Methyl Pyruvate, Ethyl Pyruvate, Propyl Pyruvate, Methyl Acetate, Ethyl Acetate, Cycloacetate Hexanol acetate and γ-butyrolactone, etc.

As the ether solvent, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monoethyl ether, Ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methyl butanol, Tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethyl ether Glycol dibutyl ether, anisole, phenethyl ether and methyl anisole, etc.

Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, and 3-methoxypropionic acid. Methyl ester, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, 2-methoxypropionic acid Ethyl, 2-methoxypropionate, 2-ethoxypropionate, 2-ethoxypropionate, 2-ethoxypropionate, 2-methoxy-2-methylpropionate, 2- Ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate , Propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether acetate, etc.

Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-heptanone Methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone, etc.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

As an aromatic hydrocarbon solvent, benzene, toluene, xylene, mesitylene, etc. are mentioned.

As an amide solvent, N,N- dimethylformamide, N,N- dimethylacetamide, N-methylpyrrolidone, etc. are mentioned.

The organic solvent (C) preferably contains at least one selected from the group consisting of ether solvents, ether ester solvents, ketone solvents, and amide solvents, and more preferably contains ether ester solvents, ketone solvents, and amide solvents One or more of the group consisting of solvents, preferably one or more selected from the group consisting of propylene glycol monomethyl ether acetate, 4-hydroxy-4-methyl-2-pentanone, and N-methylpyrrolidone One or more of them, more preferably propylene glycol monomethyl ether acetate and/or N-methylpyrrolidone, and particularly preferably propylene glycol monomethyl ether acetate.

The content rate of the organic solvent (C) 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, it is preferable that it is 5-30 mass %, and, as for the solid content of a colored resin composition, it is more preferable that it is 8-25 mass %. When the content rate of the organic solvent (C) is within the above range, the flatness at the time of coating is good, and the color density is not insufficient when the color filter is formed, so that the display characteristics tend to be good.

The content of propylene glycol monomethyl ether acetate is preferably 50 to 100% by mass, more preferably 70 to 100% by mass, and still more preferably 80 to 100% by mass in the total amount of the organic solvent (C). , more preferably 90 to 100 mass %, particularly preferably 100 mass %.

The total content of the colorant (A), the resin (B) and the organic solvent (C) is preferably 60 to 100% by mass, more preferably 80 to 100% by mass, relative to the total amount of the colored resin composition, More preferably, it is 90-100 mass %, More preferably, it is 99-100 mass %.

＜Leveler (D)＞ The colored resin composition may contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (D)). As a leveling agent (D), a silicone type surfactant, a fluorine type surfactant, a silicone type surfactant which has a fluorine atom, etc. are mentioned. These etc. may have a polymerizable group in a side chain. As a silicone type surfactant, the surfactant etc. which have a siloxane bond in a molecule|numerator are mentioned. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone Ketone SH30PA, Toray Silicone SH8400 (trade name, manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive High-tech Materials Japan Co., Ltd.), etc.

As said fluorine type surfactant, the surfactant etc. which have a fluorocarbon chain in a molecule|numerator are mentioned. Specifically, Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Corporation), Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, Eftop EF352 (manufactured by Mitsubishi Materials Corporation), Surflon (registered trademark) S381 , Surflon S382, Surflon SC101, Surflon SC105 (AGC (stock) manufacturing (old Asahi Glass (stock))) and E5844 (Daikin Fine Chemical Research Institute (stock) manufacturing) and so on.

As a silicone type surfactant which has the said fluorine atom, the surfactant etc. which have a siloxane bond and a fluorocarbon chain in a molecule|numerator are mentioned. Specifically, MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation), etc. may be mentioned.

When the leveling agent (D) is included, the content of the leveling agent (D) 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. In addition, the content rate of the said pigment dispersing agent is not included in this content rate. When the content rate of the leveling agent (D) is within the above range, the flatness of the color filter can be improved.

The total content of the colorant (A), the resin (B), the organic solvent (C), and the leveling agent (D) is preferably 60 to 100% by mass relative to the total amount of the coloring resin composition, more preferably It is 80-100 mass %, More preferably, it is 90-100 mass %, More preferably, it is 99-100 mass %, Most preferably, it is 100 mass %.

<Colored curable resin composition> The present invention also includes a coloring containing the above-mentioned colored resin composition, a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (E)), and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (F)). Curable resin composition.

<Polymerizable compound (E)> The polymerizable compound (E) is a compound that can be polymerized by active radicals and/or acids generated by the polymerization initiator (F), for example, a compound having a polymerizable ethylenically unsaturated bond, etc. Preferably it is a (meth)acrylate compound.

The polymerizable compound (E) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. As such a polymerizable compound, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, for example Esters, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, pentaerythritol ten(meth)acrylate, pentaerythritol nona(meth)acrylate Esters, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylic acid Ester, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, caprolactone modified dipentaerythritol hexa(meth)acrylate meth)acrylate, etc. Among them, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferable.

The weight average molecular weight of the polymerizable compound (E) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

About content of a polymerizable compound (E), 1-65 mass parts is preferable with respect to 100 mass parts of said resin (B), 5-60 mass parts is more preferable, 10-55 mass parts is still more preferable.

<Polymerization initiator (F)> The polymerization initiator (F) is not particularly limited as long as it is a compound capable of generating active radicals, acids, etc. by the action of light or heat to initiate polymerization, and known polymerization initiators can be used. As a polymerization initiator which generates an active radical, a benzophenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyl oxime compound, and a biimidazole compound are mentioned, for example.

The above-mentioned O-acyl oxime compound is a compound having a partial structure represented by the following formula (d1). Hereinafter, * represents a bond key.

[Chemical 19]

As said O-acyl oxime compound, for example, N-benzyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzyloxy-1-(4-phenylthiophenyl)-butane-1-one-2-imine, N-benzyloxy-1-(4-phenylthiophenyl)-butane-1-one-2-imine, Oxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzyloxy-1-(4-phenylsulfanylphenyl)-3- Cyclopentylpropan-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzyl)-9H-carbazol-3-yl] Ethane-1-imine, N-acetyloxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxolane methoxy)benzyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methyl) Benzyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzyloxy-1-[9-ethyl-6-(2-methyl) Benzyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenylthiophenyl) -3-cyclohexylpropan-1-one-2-imine, etc. Commercially available products such as Irgacure OXE01, Irgacure OXE02 (all of which are manufactured by BASF), and N-1919 (manufactured by ADEKA) can also be used. Among them, the O-acyl oxime compound is preferably selected from N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N- Benzyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzyloxy-1-(4-phenylsulfanylphenyl) Composed of octane-1-one-2-imine and N-benzyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine At least one of the group, more preferably N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropan-1-one-2-imine, N-benzyl Oxy-1-(4-phenylthiophenyl)octan-1-one-2-imine. In the case of these O-acyl oxime compounds, there is a tendency that a color filter with high brightness can be obtained.

The above-mentioned benzophenone compound is a compound having a partial structure represented by the following formula (d2) or a partial structure represented by the following formula (d3). In these partial structures, the benzene ring may have a substituent.

[hua 20]

As a compound having a partial structure represented by formula (d2), for example, 2-methyl-2-𠰌olinyl-1-(4-methylthiophenyl)propan-1-one, 2-di Methylamino-1-(4-𠰌olinylphenyl)-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl] -1-[4-(4-morpholinyl)phenyl]butan-1-one, etc. Commercially available products such as Irgacure 369, Irgacure 907, and Irgacure 379 (all of which are manufactured by BASF) can also be used.

As a compound having a partial structure represented by formula (d3), for example, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4 -(2-Hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1 -Oligomers of ketones, α,α-diethoxyacetophenone, benzalkonium dimethyl ketal, etc. In terms of sensitivity, the benzophenone compound is preferably a compound having a partial structure represented by the formula (d2).

As said triazine compound, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(triazine, Chloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-sunenyl-1,3,5-triazine oxazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6- [2-(5-Methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl ) vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]- 1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine Wait.

As said acyl phosphine oxide compound, 2, 4, 6- trimethylbenzyl diphenyl phosphine oxide etc. are mentioned. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can also be used.

As said biimidazole compound, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3 -Dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, refer to Japanese Patent Laid-Open No. 6-75372, Japanese Patent Laid-Open No. 6-75373, etc.), 2, 2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5 '-Tetrakis(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(dialkoxyphenyl)biimidazole, 2 ,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole (for example, refer to Japanese Patent Publication No. 48-38403, Japanese Patent Japanese Patent Laid-Open No. 62-174204, etc.), biimidazole compounds in which the phenyl group at the 4,4'5,5'-position is substituted with an alkoxycarbonyl group (for example, see Japanese Patent Laid-Open No. 7-10913, etc.), etc. .

Further, examples of the polymerization initiator (F) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate , 4-phenylbenzophenone, 4-benzyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)diphenyl Benzophenone compounds such as ketone, 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthraquinone, 2-ethylanthraquinone, camphorquinone; 10-butyl-2- Chloracridone, benzyl, methyl phenylglyoxylate, titanocene compounds, etc. These and the like are preferably used in combination with the following polymerization initiation aids (F1) (especially amines).

As a polymerization initiator for generating acid, for example, 4-hydroxyphenyldimethylperylene p-toluenesulfonate, 4-hydroxyphenyldimethylperylene hexafluoroantimonate, 4-acetoxybenzene Dimethyl perylene p-toluenesulfonate, 4-acetoxyphenylmethylbenzyl perylene hexafluoroantimonate, triphenyl perylene p-toluenesulfonate, triphenyl perylene hexafluoroantimonate, Diphenyl iodonium p-toluenesulfonate, diphenyl iodonium hexafluoroantimonate and other onium salts, or nitrobenzyl tosylate, benzoin tosylate, etc.

As the polymerization initiator (F), it is preferably a polymerization comprising at least one selected from the group consisting of benzophenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds and biimidazole compounds The initiator is more preferably a polymerization initiator containing an O-acyl oxime compound.

The content of the polymerization initiator (F) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (E). If the content of the polymerization initiator (F) is within the above-mentioned range, the sensitivity will be increased and the exposure time will tend to be shortened, so that the productivity of the optical filter will be improved.

、甘胺酸N-苯酯等。<Polymerization initiation aid (F1)> The colored resin composition may contain a polymerization initiation aid (hereinafter, sometimes referred to as a polymerization initiation aid (F1)). The polymerization initiator (F1) is a compound or a sensitizer for promoting the polymerization of the polymerizable compound whose polymerization is initiated by the polymerization initiator. When a polymerization initiator (F1) is contained, it is usually used in combination with a polymerization initiator (F). As the polymerization initiator (F1), 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)di Benzophenone, 9,10-dimethoxyanthracene, 2,4-diethyl 9-oxosulfan

, N-phenyl glycine, etc.

When these polymerization initiators (F1) are used, their content is 100 parts by mass relative to the total amount of the resin (B) and the polymerizable compound (E), preferably 0.1 to 30 parts by mass, more preferably It is 1-20 mass parts. If the amount of the polymerization initiation aid (F1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.

＜Other ingredients＞ The colored resin composition of the present invention may optionally contain additives known in the technical field such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents.

<Color filter, display device> The present invention also includes a color filter formed from the above-mentioned colored resin composition and colored curable resin composition. The coloring resin composition and the coloring curable resin composition of the present invention have high green lightness, and thus the green lightness of the color filter obtained by using them is also high. The color filter can be used as a filter used in display devices (eg, liquid crystal display devices, organic EL (Electroluminescence) devices, electronic paper, etc.) and solid-state imaging elements.

<The manufacturing method of a colored resin composition and a colored curable resin composition> The colored resin composition of the present invention can be prepared, for example, by mixing a colorant (A), a resin (B), and optionally an organic solvent (C), a leveling agent (D), and other components. Furthermore, the colored curable resin composition of the present invention can be prepared by mixing the colored resin composition with the colored curable resin composition containing the polymerizable compound (E) and the polymerization initiator (F).

The colorant (A) can also be prepared using the above-mentioned colored dispersion liquid or pigment dispersion liquid. The target colored resin composition can be prepared by mixing the remaining components in the colored dispersion liquid or the pigment dispersion liquid so as to have a specific concentration.

When the dye (A1-1) is included, the dye (A1-1) may be dissolved in a part or all of the organic solvent (C) in advance to prepare a solution. Preferably, the solution is filtered with a filter having a pore size of about 0.01 to 1 μm. Moreover, it is preferable to filter the coloring resin composition after mixing with the filter with a pore diameter of about 0.01-10 micrometers.

<Manufacturing method of color filter> As a method of producing a colored pattern from the colored resin composition and colored curable resin composition of the present invention, a photolithography method, an inkjet method, a printing method, etc. may be mentioned. Among them, photolithography is preferred. The photolithography method is a method in which the above-mentioned colored resin composition is applied on a substrate, dried to form a colored composition layer, and developed by exposing the colored composition layer through a photomask. In the photolithography method, a colored coating film which is a cured product of the above-mentioned colored composition layer can be formed by not using a photomask and/or without performing development at the time of exposure. By obtaining a colored pattern or a colored coating film or the like in this way, a color filter can be formed.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is Silica-coated, or polycarbonate, polymethyl methacrylate, etc. can be used. Resin plates such as polyester, polyethylene terephthalate, silicon, and aluminum, silver, silver/copper/palladium alloy thin films, etc. are formed on the above-mentioned substrates. On these substrates, other color filter layers, resin layers, transistors, circuits, etc. may also be formed. In addition, a substrate obtained by performing HMDS (hexa-methyl-disilazane, hexamethyldisilazane) treatment on a silicon substrate can also be used.

The photolithography method can be used to form pixels of various colors under known or conventional devices or conditions. For example, it can be produced as follows. First, the colored resin composition is applied on a substrate, and dried by heating (pre-baking) and/or drying under reduced pressure to remove volatile components such as a solvent and dry to obtain a smooth colored composition layer. As a coating method, a spin coating method, a slit coating method, a slit and spin coating method, etc. are mentioned. In the case of heating and drying, the temperature is preferably 30 to 120°C, more preferably 50 to 110°C. Moreover, as a heating time, 10 seconds - 60 minutes are preferable, and 30 seconds - 30 minutes are more preferable. In the case of drying under reduced pressure, it is preferably carried out in a temperature range of 20 to 25°C under a pressure of 50 to 150 Pa.

The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.

Next, the coloring composition layer is exposed to light through a photomask for forming a target coloring pattern as necessary. The pattern on the photomask is not particularly limited, and a pattern corresponding to the intended use can be used. The light source used for exposure is preferably a light source that emits light having a wavelength of 250 to 450 nm. For example, the light that does not reach 350 nm can also be cut off by a filter that can cut off this wavelength region, or the light near 436 nm, 408 nm, and 365 nm can be selected with a bandpass filter that extracts these wavelength regions. Extracted sexually. Specifically, as a light source, a mercury lamp, a light emitting diode, a metal halide lamp, a halogen lamp, etc. are mentioned.

Since the entire exposure surface can be uniformly irradiated with parallel light, or the photomask can be accurately aligned with the substrate on which the coloring composition layer is formed, it is preferable to use a photomask alignment exposure machine, a stepper, etc. for reduced projection Exposure device or proximity exposure device.

The coloring pattern is formed on the substrate by contacting the exposed coloring composition layer with a developer for development. By developing, the unexposed part of the coloring composition layer is dissolved in the developing solution and removed. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide is preferable. The concentration of these basic compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Furthermore, the developer may contain a surfactant. The development method may be any of a liquid coating method, a dipping method, a spray method, and the like. Furthermore, the substrate can be inclined at any angle during development. After development, it is preferable to wash with water.

Furthermore, it is preferable to post-bake the coloring pattern obtained. The post-baking temperature is preferably 80 to 250°C, more preferably 100 to 245°C, and further preferably 180 to 240°C. The post-baking time is preferably 1 to 120 minutes, more preferably 2 to 30 minutes.

The film thickness of the coating film after post-baking is, for example, preferably 3 μm or less, and more preferably 2.0 μm or less. The lower limit of the film thickness of the coating film is not particularly limited, but is usually 0.1 μm or more, and may be 0.5 μm or more. [Example]

Hereinafter, the present invention will be described in more detail by way of examples, but it goes without saying that the present invention is not limited by the following examples. In an example, unless otherwise specified, "part" means "mass part", and "%" means "mass %".

(Synthesis example 1 of pigment) The following compound (I-1) was synthesized according to the contents described in Patent No. 6206977 .

[Chemical 21]

(Synthesis example 2 of dye) The following compound (X-1) was synthesized according to the contents described in International Publication No. 2016/076028.

[Chemical 22]

(Synthesis example 3 of dye) Compound (I-2) was synthesized according to the following scheme.

[Chemical 23]

Synthesis of Intermediate (I-2a) 12.8 parts of 3-(pentafluorothio)phenylboronic acid (manufactured by Ube Industries, Ltd.) and 7.00 parts of 3-chlorophthalonitrile (manufactured by Kanto Chemical Co., Ltd.) were added to the four-necked flask after nitrogen replacement. ), 15.7 parts of cesium fluoride (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.48 part of tris(dibenzylideneacetone)dipalladium (0) (manufactured by NEChemcat Co., Ltd.), 0.53 part of tri-tert-butyl Phosphonium tetrafluoroborate (manufactured by Tokyo Chemical Industry Co., Ltd.), 112 parts of 1,4-dioxane (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.3 parts of ion-exchanged water were stirred at 93° C. for 7 hours. After that, the contents were cooled to room temperature, toluene was added thereto and stirred at room temperature for 30 minutes. Then, insoluble matter was removed by filtration, and the obtained filtrate was washed three times with ion-exchanged water. Then, anhydrous magnesium sulfate was added to the obtained organic layer, it was filtered after drying, and the obtained filtrate was concentrated. Thereafter, the obtained brown solid was washed with a mixed solvent of toluene/methanol, and then recrystallized from a mixed solvent of acetonitrile/ion-exchanged water, whereby 9.63 parts (yield 68%) of white solid was obtained. Intermediate (I-2a).

Synthesis of Compound (I-2) To the eggplant-shaped flask substituted with nitrogen, 1.00 parts of intermediate (I-2a) and 0.14 parts of zinc chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added, and the mixture was stirred at 220° C. for 1.5 hours. Then, the obtained mixture was dissolved in toluene, and purified by gel permeation chromatography (gel carrier: Bio-Beads S-X3 Support, manufactured by BIO-RAD) to obtain 0.37 part (yield) 36%) Compound (I-2) in the form of a dark green solid.

(Synthesis example 4 of dye) Compound (I-3) was synthesized according to the following scheme.

[Chemical 24]

Synthesis of Intermediate (I-3a) To a four-necked flask replaced with nitrogen, 11.9 parts of 4-(pentafluorothio)phenylboronic acid (manufactured by Ube Industries, Ltd.), 6.50 parts of 3-chlorophthalonitrile, 14.6 parts of cesium fluoride, 0.45 Parts of tris(dibenzylideneacetone)dipalladium(0), 0.49 parts of tris-tert-butylphosphonium tetrafluoroborate, 103 parts of 1,4-dioxane and 4 parts of ion-exchanged water, stirred at 93°C 8 hours. After that, the contents were cooled to room temperature, toluene was added thereto and stirred at room temperature for 30 minutes. Then, insoluble matter was removed by filtration, and the obtained filtrate was washed three times with ion-exchanged water. Then, anhydrous magnesium sulfate was added to the obtained organic layer, it was filtered after drying, and the obtained filtrate was concentrated. Thereafter, the obtained brown solid was washed with a mixed solvent of toluene/methanol, and then recrystallized from a mixed solvent of acetonitrile/ion-exchanged water, whereby 4.26 parts (yield 32%) of white solid was obtained. Intermediate (I-3a).

Synthesis of Compound (I-3) To the eggplant-shaped flask substituted with nitrogen, 1.00 parts of intermediate (I-3a) and 0.14 parts of zinc chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added, and the mixture was stirred at 220° C. for 1 hour. Then, the obtained mixture was cooled to room temperature, and washed with methanol, whereby 0.12 part (yield 12%) of compound (I-3) was obtained as a turquoise solid.

(Synthesis example 5 of dye) Mixture (I-4) was synthesized according to the following scheme.

[Chemical 25]

Synthesis of mixture (I-4) Into the eggplant-shaped flask substituted with nitrogen, 1.00 parts of intermediate (I-3a), 0.39 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd., Pn) and 0.14 parts of zinc chloride were added, and the mixture was stirred at 220° C. 1.5 hours. Thereafter, the obtained mixture was cooled to room temperature, washed repeatedly with a mixed solvent of acetonitrile/ion-exchanged water, thereby obtaining 0.31 part of a mixture (I- 4).

(Synthesis Example 1 of Resin) A suitable amount of nitrogen was charged into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace it with a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the flask was heated at 80°C while stirring. . Next, a mixed solution containing 38 parts of acrylic acid, 289 parts of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-8-yl acrylate and 3 acrylic acid was added dropwise to the flask over 5 hours. , 4-epoxy tricyclo[5.2.1.0 ^2,6 ]decane-9-yl ester mixture (mixing ratio is 1:1), 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a mixture obtained by dissolving 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) as a polymerization initiator in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. mixture. After the dropping was completed, the flask was kept at 80°C for 4 hours, and then cooled at room temperature to obtain a copolymer (resin (resin ( B-1)) solution. The resulting copolymer (polymer; resin (B-1)) had a weight-average molecular weight Mw of 9200, a degree of dispersion of 2.08, and a solid content acid value of 77 mg-KOH/g. Resin (B-1) has the following structural unit.

[Chemical 26]

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by GPC (gel permeation chromatography) method under the following conditions. Device: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: THF (tetrahydrofuran) Flow rate: 1.0 mL/min Test liquid solid content concentration: 0.001 to 0.01% by mass Injection volume: 50 μL Detector: RI Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio (Mw/Mn) of the weight average molecular weight in terms of polystyrene obtained above and the number average molecular weight (Mw/Mn) was used as the degree of dispersion.

(Preparation of Dispersion Liquid (P-1)) 12.0 parts of the above-mentioned compound (X-1), 4.8 parts of a dispersant (BYK-LPN 21324 manufactured by BYK-Chemie Japan), 3.6 parts of the above-mentioned resin (B-1) (in terms of solid content), and 79.6 parts of the solvent were used. Propylene glycol monomethyl ether acetate was mixed, 300 parts of zirconia beads were added and shaken, and the zirconia beads were removed by filtration to prepare a dispersion liquid (P-1).

[Examples 1 to 4, Comparative Example 1] Finally, each component was mixed so that it might become the composition shown in following Table 3, and the colored resin composition of Examples 1-4 and Comparative Example 1 was obtained. In addition, in the comparative example 1, the said dispersion liquid (P-1) was used for mixing.

[table 3] The unit is (mass parts) Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Colorant I-1 14.3 I-2 17.7 I-3 17.7 I-4 25 X-1 27.8 Dispersant A-1 11.1 resin B-1 100 100 100 100 100 solvent C-1 648 190 667 709 603 C-2 533 leveling agent D-1 0.04 0.04 0.04 0.04 0.05

In Table 3, each component represents the following compounds. Colorant (I-1): compound represented by formula (I-1) Colorant (I-2): compound represented by formula (I-2) Colorant (I-3): compound represented by formula (I-3) Colorant (I-4): compound represented by formula (I-4) Colorant (X-1): compound represented by formula (X-1) Dispersant (A-1): Acrylic Dispersant (BYK-LP N21324 manufactured by BYK-Chemie Japan) Resin (B-1): Resin (B-1) (solid content conversion) Solvent (C-1): propylene glycol monomethyl ether acetate Solvent (C-2): N-methylpyrrolidone (NMP) Leveling agent (D-1): polyether modified polysiloxane oil (“Toray Silicone SH8400” manufactured by Toray Dow Corning Co., Ltd.)

<Production of Color Filter (Colored Coating Film)> The colored resin composition was coated on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Corporation) by spin coating, and then prebaked at 100° C. for 3 minutes. Then, it post-baked at 230 degreeC for 30 minutes, and obtained the colored coating film.

<Production example 1> (Production of yellow resin composition) 6.6 parts of CI Pigment Yellow 185 (Y185) as a yellow pigment, 5.0 parts of a dispersant (BYK-LP 6919 manufactured by BYK-Chemie Japan), 3.0 parts of the above-mentioned resin B-1 (in terms of solid content), and 85.4 parts as The solvent and propylene glycol monomethyl ether acetate were mixed, 300 parts of zirconia beads were added for shaking, and the zirconia beads were removed by filtration to prepare a yellow resin composition.

<Production example 2> (Production of Green Resin Composition) 6.6 parts of CI Pigment Green 63 (G63) as a green pigment, 6.0 parts of a dispersant (BYK-LP 21116 manufactured by BYK-Chemie Japan), 5.0 parts of the above-mentioned resin B-1 (in terms of solid content), and 82.4 parts Propylene glycol monomethyl ether acetate as a solvent was mixed, 300 parts of zirconia beads were added and shaken, and the zirconia beads were removed by filtration to prepare a green resin composition.

<Measurement of transmission spectrum> The transmission spectrum of the said colored coating film, the yellow resin composition, and the green resin composition was measured using the colorimeter (OSP-SP-200) apparatus manufactured by Olympus Corporation.

＜Calculation of lightness＞ Using the transmission spectra obtained from the colored resin compositions of Examples or Comparative Examples, the transmission spectra obtained from the yellow resin compositions and green resin compositions of Production Examples 1 and 2, and the characteristic function of the C light source, the CIE chromaticity coordinates were obtained (x, y)=Calculation formula of lightness Y at (0.2550, 0.6500). Specifically, the colored resin compositions and the yellow colored resin compositions of Examples 1 to 4 or Comparative Example 1 were mixed (simulated mixing) according to the ratios in Table 4 below, so that the color matching calculation by additive color mixing complies with the CIE The chromaticity coordinates (x, y)=(0.2550, 0.6500), thereby obtaining the calculation formula of the lightness Y. Similarly, the colored resin compositions, the yellow colored resin compositions, and the green colored resin compositions of Examples 1 to 4 and Comparative Example 1 were mixed (simulated mixing) at the ratios in the following Table 4, respectively, so as to satisfy the CIE color. The degree coordinates (x, y)=(0.2550, 0.6500), so that Examples 5 to 8 and Comparative Example 2 are constructed, and the calculation formula of the lightness Y is obtained. The larger the value of Y, the higher the brightness.

[Table 4] Composition (mass %) Brightness (Y) I-1 I-2 I-3 I-4 X-1 Y185 G63 Example 1 72 28 47.0 Example 2 89 11 43.8 Example 3 81 19 47.7 Example 4 64 36 46.6 Example 5 52 27 twenty one 48.1 Example 6 66 13 twenty one 46.2 Example 7 59 20 twenty one 48.5 Example 8 47 32 twenty one 47.6 Comparative Example 1 33 67 39.8 Comparative Example 2 twenty three 55 twenty two 42.9

[Example 9, Comparative Example 3] The polymerizable compound (E) and the polymerization initiator (F) were added to the colored resin compositions of Example 1 and Comparative Example 1 in Table 3 above, respectively, to obtain the colored curable resins of Example 9 and Comparative Example 3. combination. The colored curable resin composition was coated on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning) by spin coating, and then prebaked at 100° C. for 3 minutes, and then baked at 230° C. After baking for 30 minutes, a colored coating film can be obtained, and the colored coating film can also obtain the same brightness in the same CIE chromaticity coordinates. [Industrial Availability]

According to the colored resin composition of the present invention, a color filter with high green brightness can be formed.

Claims (7)

A coloring resin composition is characterized in that: it contains a colorant and a resin, and the colorant contains a phthalocyanine compound in which one or more hydrogen atoms are substituted with SF ₅ . The colored resin composition according to claim 1, wherein the colorant contains a compound represented by the following formula (1a) and/or (1b). [hua 1]

[hua 2]

[In formula (1a) and formula (1b), R ^x each independently represents SF ₅ , or a hydrocarbon group having 1 to 20 carbon atoms in which one or more hydrogen atoms are substituted with SF ₅ , m represents an integer of 1 to 16, R ^y each independently represents an optionally substituted hydrocarbon group having 1 to 20 carbon atoms, n represents an integer of 0 to 15, M represents an optionally substituted metal element or an optionally substituted semimetal element, R ^x and -CH ₂ - of the hydrocarbon group represented by R ^y may be substituted with -O-, -S-, -SO ₂ -, -NH-, -CO- or -CO ₂ -]. The colored resin composition according to claim 2, wherein the compound represented by the above formula (1a) is a compound represented by the following formula (2a), and the compound represented by the above formula (1b) is represented by the following formula (2b) the compound. [hua 3]

[hua 4]

[In formula (2a) and formula (2b), R ^x , R ^y , and M respectively have the same meanings as described above, o represents an integer of 1 to 4, and p represents an integer of 0 to 3]. The colored resin composition according to any one of claims 1 to 3, wherein the colorant comprises at least one pigment selected from the group consisting of yellow pigments and green pigments. A colored curable resin composition comprising the colored resin composition according to any one of claims 1 to 4, a polymerizable compound, and a polymerization initiator. A color filter formed of the coloring curable resin composition as claimed in claim 5. A display device comprising the color filter of claim 6.