KR20180006316A - Pigment composition, colored composition and colored curable composition - Google Patents

Abstract

The present invention relates to a pigment composition, a coloring composition, and a color-curable composition. According to an embodiment of the present invention, the pigment composition includes: a compound represented by the formula (I); and one or more substances selected from a group including quinophthalone compounds, isoindoline compounds other than the compound represented by the formula (I), and green coloring agents. The compound represented by the formula (I) can be a compound represented by the formula (I-a). In the above-described formula, R^11 and R^14 are the same group while L^1 and L^2 can be the same group.

Description

PIGMENT COMPOSITION, COLORED COMPOSITION AND COLORED CURABLE COMPOSITION [0002]

The present invention relates to pigment compositions, coloring compositions and colored curable compositions.

The colored curable composition is used for the production of a color filter used in a display device such as a liquid crystal display device, an electroluminescence display device, and a plasma display. The colored curable composition may contain two or more kinds of coloring agents having different colors in order to obtain a desired color tone or the like.

For example, Japanese Patent Application Laid-Open No. 2015-197677 (Patent Document 1) discloses a colored photosensitive composition for a green color filter. Pigment Green 7, and C.I. Pigment Yellow 129 and C.I. Pigment Yellow 139. It is also disclosed that at least one yellow pigment selected from the group consisting of Pigment Yellow 139 is contained.

The present invention includes the following inventions.

[1] A compound represented by formula (I)

A quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), and a green colorant.

[In the formula (I), L ¹ represents -CO- or -SO ₂ -.

R ¹ ~R ⁵ ~R ¹² and R ¹³ are, independently, a hydrogen ^{atom, -CO-R 102, -COO-} R 101, -OCO-R 102, -COCO-R 102, -OR 102, -SO each other _{^{2 -R 101, -SO 2 N (}} R 102) 2, -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102 , -OCON (R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent .

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ may be bonded to each other to form a ring.

R ¹¹ and R ¹⁰¹ independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ¹⁰² represents a hydrogen atom, a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M represents a hydrogen atom or an alkali metal atom.

When a plurality of R ¹⁰¹ , R ¹⁰² and M exist, they may be the same or different.

And the broken line represents E-form or Z-form.

[2] The pigment composition according to [1], wherein the compound represented by the formula (I) is a compound represented by the formula (I-a).

[In the formula (I-a), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.

L ² represents -CO- or -SO ₂ -.

R ¹⁴ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.]

[3] The pigment composition according to [2], wherein R ¹¹ and R ¹⁴ are the same group, and L ¹ and L ² are the same group.

[4] The compound according to [1], wherein R ¹¹ and R ¹⁴ are each independently selected from the group consisting of an alkyl group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent or a tetrahydronaphthyl group , A thienyl group which may have a substituent, a furyl group which may have a substituent or a pyridinyl group which may have a substituent (s).

[5] The pigment composition according to [1], wherein the compound represented by the formula (I) is a compound represented by the formula (I-b).

[In the formula (I-b), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.

R ²⁰ and R ³⁰ combine to form a ring Q.

The ring Q may have a substituent, may be a ring having 5 to 7 ring members, and the ring Q may be a hydrocarbon ring or a heterocyclic ring. The ring Q may be bonded to a monocyclic ring having 5 to 7 ring members selected from a hydrocarbon ring and a heterocyclic ring or a condensed ring condensed with the monocyclic ring.

[6] The pigment composition according to [5], wherein the compound represented by the formula (I) is a compound represented by the formula (I-c).

[In the formula (I-c), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.

R ⁶ and R ⁷ independently represent a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , _{^{SO 2 N (R 102) 2}} , -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102, -OCON (R 102 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ¹⁰¹ , R ¹⁰² and M have the same meanings as defined above.

[7] The pigment composition according to any one of [1] to [6], wherein R ¹ is a hydrogen atom and R ² to R ⁵ are each independently a hydrogen atom or a nitro group.

[8] A coloring composition comprising the pigment composition according to any one of [1] to [7] and a solvent.

[9] The colored composition according to [8], further comprising a resin.

[10] The coloring composition according to any one of [8] to [9], further comprising a compound represented by the formula (I), a yellow colorant or a green colorant.

[11] A colored curable composition comprising the coloring composition according to any one of [8] to [10] and a polymerizable compound.

[12] The colored curable composition according to [11], further comprising a polymerization initiator.

[13] A color filter formed from the coloring composition or the color-curable composition according to any one of [8] to [12].

[14] A liquid crystal display device comprising the color filter according to [13].

[15] A compound represented by the formula (I)

A quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), and a green colorant; and a pigment composition comprising at least one pigment selected from the group consisting of

A solvent,

The liquid containing the colorant (A2) and the colorant (A2)

≪ / RTI >

[In the formula (I), L ¹ represents -CO- or -SO ₂ -.

R ¹ ~R ⁵ ~R ¹² and R ¹³ are, independently, a hydrogen ^{atom, -CO-R 102, -COO-} R 101, -OCO-R 102, -COCO-R 102, -OR 102, -SO each other _{^{2 -R 101, -SO 2 N (}} R 102) 2, -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102 , -OCON (R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent .

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ may be bonded to each other to form a ring.

R ¹¹ and R ¹⁰¹ independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ¹⁰² represents a hydrogen atom, a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M represents a hydrogen atom or an alkali metal atom.

When a plurality of R ¹⁰¹ , R ¹⁰² and M exist, they may be the same or different.

And the broken line represents E-form or Z-form.

[16] The production method according to [15], wherein the colorant (A2) is at least one colorant selected from a compound represented by the formula (I), a green colorant and a yellow colorant.

The present invention provides a pigment composition, a coloring composition and a colored curable composition which can be used for forming a color filter having improved light resistance.

The pigment composition of the present invention can be produced by mixing a compound represented by the formula (I) (hereinafter sometimes referred to as a compound (I)) with an isoindoline compound other than the quinophthalone compound, the compound (I) And at least one selected from the group consisting of

Compound (I) also includes its tautomeric isomers and their salts.

Compound (I) can be used as a coloring agent.

The pigment composition of the present invention may contain one or more compounds (I).

At least one member selected from the group consisting of a quinophthalone compound, an isoindoline compound other than the compound (I), and a green colorant can be used as a colorant.

The pigment composition of the present invention includes at least one kind selected from the group consisting of a quinophthalone compound, an isoindoline compound other than the compound (I), and a green colorant.

The pigment composition of the present invention may contain a colorant other than the compound (I) and the quinophthalone compound (hereinafter sometimes referred to as a colorant (A1-1)).

The pigment composition of the present invention may contain a colorant other than an isoindoline compound other than the compound (I) and the compound (I) (hereinafter sometimes referred to as a colorant (A1-2)).

The pigment composition of the present invention may contain a colorant other than the compound (I) and the green colorant (hereinafter sometimes referred to as a colorant (A1-3)).

The coloring composition of the present invention comprises at least one pigment selected from the group consisting of the pigment composition and the solvent (E), that is, the compound (I), the quinophthalone compound, the isoindoline compound other than the compound And a solvent (E). It is preferable that at least one member selected from the group consisting of the compound (I) and the quinophthalone compound, the isoindoline compound other than the compound (I), and the green colorant is dispersed in the solvent (E).

The coloring composition of the present invention may contain a resin (hereinafter sometimes referred to as resin (B)).

The coloring composition of the present invention may contain a coloring agent (hereinafter sometimes referred to as a coloring agent (A2)).

The colorant (A2) may contain one or two or more coloring agents.

The colorant (A2) preferably contains the compound (I), a yellow colorant or a green colorant.

The colored curable composition of the present invention is obtained by mixing the pigment composition, the solvent (E) and the polymerizable compound (C), that is, the compound (I) and the quinophthalone compound, the isoindoline compound other than the compound A colorant, a solvent (E), and a polymerizable compound (C).

The colored curable composition of the present invention may contain a polymerization initiator (D).

The colored curable composition of the present invention may contain a polymerization initiator (D1).

The coloring composition of the present invention may further contain a leveling agent (F) and an antioxidant.

≪ Compound (I) >

The compound (I) is a compound represented by the formula (I).

[In the formula (I), L ¹ represents -CO- or -SO ₂ -.

R ¹ ~R ⁵ ~R ¹² and R ¹³ are, independently, a hydrogen ^{atom, -CO-R 102, -COO-} R 101, -OCO-R 102, -COCO-R 102, -OR 102, -SO each other _{^{2 -R 101, -SO 2 N (}} R 102) 2, -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102 , -OCON (R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent .

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ may be bonded to each other to form a ring.

R ¹¹ and R ¹⁰¹ independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ¹⁰² represents a hydrogen atom, a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M represents a hydrogen atom or an alkali metal atom.

When a plurality of R ¹⁰¹ , R ¹⁰² and M exist, they may be the same or different.

And the broken line represents E-form or Z-form.

In the present specification, the broken line indicates the E-form or the Z-form, and specifically, the broken line indicates that the E-form, the Z-form, or a mixture thereof is included.

R ¹ to R ⁵ and R ¹² to R ¹³ independently represent a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , _{^{SO 2 N (R 102) 2}} , -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, a halogen atom, a cyano group, a nitro _{group, -SO 3 M, -CO 2 M} , A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

L ¹ is preferably -CO-.

The number of carbon atoms of the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² is 1 to 40, preferably 1 to 30, more preferably 1 to 20, Preferably from 1 to 15, and even more preferably from 1 to 10.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may} be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated , Chain (chain) or alicyclic (alicyclic).

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, A straight chain alkyl group such as an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a heptadecyl group, an octadecyl group and an eicosyl group; (2-ethyl) butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl) pentyl group, (3-ethyl) pentyl group, an isohexyl group, a (5-methyl) hexyl group, a (2-ethyl) Branched chain alkyl group and the like; (1- (2-propenyl) propyl group, 1-propenyl group, 2-propenyl group (allyl group) Phenyl)) ethenyl group, (1,2-dimethyl) propenyl group and 2-pentenyl group; And the like. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, still more preferably 1 to 10, Is preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, and more preferably 1 to 8 carbon atoms is particularly preferable.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, , A cyclohexyl group, a cycloheptyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, Dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, Dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2 , 4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl Practical production, 4-cyclohexane Cycloalkyl groups such as rohek group; Cycloalkenyl groups such as a cyclohexenyl group (for example, cyclohex-2-ene, cyclohex-3-ene), a cycloheptenyl group and a cyclooctenyl group; Norbornane group, adamantyl group, bicyclo [2.2.2] octane, and the like. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, still more preferably 4 to 15, still more preferably 5 To 15, particularly preferably 5 to 10. Of these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

Examples of the aromatic hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include a phenyl group, o-tolyl group, m-tolyl group, p- Isopropylphenyl group, m-phenylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, Propylphenyl group, 4-pentylphenyl group, 2-tert-butylphenyl group, 2-tert-butylphenyl group, , 2-naphthyl group, 2-naphthyl group, 4-cyclohexylphenyl group, 4-cyclohexylphenyl group, An aromatic hydrocarbon group such as a 7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group and an anthryl group and a pyrenyl group; And the like.

The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 15.

The aromatic hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ^{102 may} be a hydrocarbon group (for example, an aromatic hydrocarbon group, a chain hydrocarbon group and an alicyclic hydrocarbon group , And an aralkyl group such as a benzyl group, a phenethyl group and a 1-methyl-1-phenylethyl group; An arylalkenyl group such as a phenylethenyl group (phenylvinyl group); An arylalkynyl group such as a phenylethynyl group; A phenyl group in which at least one of the phenyl group, the biphenyl group and the terphenyl group is bonded; A cyclohexylmethylphenyl group, a benzylphenyl group, and a (dimethyl (phenyl) methyl) phenyl group.

The group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² is a group obtained by combining the above-listed hydrocarbon groups (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group) For example, a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, Lt; RTI ID = 0.0 > alicyclic < / RTI >

The number of carbon atoms in these groups is preferably from 4 to 30, more preferably from 6 to 30, still more preferably from 6 to 20, and particularly preferably from 6 to 15.

The hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have a substituent. The substituent may be either 1 or 2. It is preferable that the divalent substituent binds two carbon atoms to the same carbon atom to form a double bond.

As the monovalent substituent,

Butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, heptyloxy group, isobutyloxy group, Ethylhexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenyl (2-ethylhexyloxy) group, An alkoxy group, an ethoxy group, a phenyloxy group, an o-tolyloxy group, a 2,3-dimethylphenyloxy group, a 2,4-dimethylphenyloxy group, a 2,5- 2, 4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4- A 4-methoxyphenyloxy group, a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 5-dicyanophenyloxy group, a 2,6-dicyanophenyloxy group, A methoxyphenyloxy group, a phenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2- An ethoxyphenyloxy group and the like, and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a group represented by the following formula or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, A group in which a group induced by a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) or the like) is bound on one side;

A methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, a (2-ethylhexylthio group, a heptylthio group, an octylthio group, , A decanyl group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;

An epoxy group, an oxetanyl group, a tetrahydrofuryl group, and a tetrahydropyranyl group;

Formyl group;

(2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, an acetyl group, an acetyl group, a propanoyl group, a butanoyl group, a 2,2-dimethylpropanoyl group, a pentanoyl group, a hexanoyl group, (Preferably having 1 to 11 carbon atoms) such as a dodecanoyl group, a hecinocanoyl group, a benzoyl group, etc., and a group represented by the following formula (for example, a hydrocarbon group having 1 to 20 carbon atoms, A group derived from a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) When the alkanoyl group is used, the number of carbon atoms is preferably 2 to 12;

(2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, butoxycarbonyl, butoxycarbonyl, (Preferably having 1 to 20 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, a hexyl group, A halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an oxo group having 1 to 10 carbon atoms) Oxycarbonyl group to which a group induced by, for example, a tilsulfamoyl group) is bonded;

An amino group;

N, N-diisopropylamino, N, N-diisopropylamino, N, N-diisopropylamino, N, N-diisopropylamino, N, Butylamino group, an N, N-di-sec-butylamino group, an N, N-diisobutylamino group, (1-ethylpropyl) amino group, N, N-di (1-ethylpropyl) amino group , N-heptylamino group, N, N-dihexylamino group, N, N-dihexylamino group, An N, N-dimethylamino group, an N, N-ethylmethylamino group, an N, N-dimethylamino group, an N, N-dialkylamino group, -Propylmethylamino group, N, N-isopropylmethylamino group, N, N-butylmethyl An amino group, an amino group, an N-decylamino group, an N, N-dodecylmethylamino group, an N-undecylamino group, , N, N-eicosylmethylamino group, N, N-tert-butylmethylamino group, N, N-phenylmethylamino group and the like and groups represented by the following formulas A halogen group (preferably a chlorine atom), an alkylsulfamoyl group having a carbon number of 1 to 10 (preferably, an alkyl group having 1 to 10 carbon atoms), or a group derived therefrom (for example, a carboxyl group, a sulfo group, a nitro group, An octylsulfamoyl group) or the like);

Sulfamoyl group;

An N, N-dimethylsulfamoyl group, an N, N-dimethylsulfamoyl group, an N, N-dimethylsulfamoyl group, An N, N-diisopropylsulfamoyl group, an N, N-diisopropylsulfamoyl group, an N-butylsulfamoyl group, an N, Butylsulfamoyl group, N, N-di-tert-butylsulfamoyl group, N-sec-butylsulfamoyl group, N, N, N-di (1-ethylpropyl) sulfamoyl group, N-hexylsulfamoyl group, N, N-diphenylsulfamoyl group, N- (2-ethyl) hexylsulfamoyl group, N-heptylsulfamoyl group, N, N-diheptylsulfamoyl group, N An N, N-dinoylsulfamoyl group, an N-phenylsulfamoyl group, an N, N-dioctylsulfamoyl group, an N, N-octylsulfamoyl group, N-diphenylsulfone An N, N-dimethylamino sulfamoyl group, an N, N-dimethylamino sulfamoyl group, an N, N-dimethylamino sulfamoyl group, , N, N-dodecylsulfamoyl, N, N-dodecylsulfamoyl, N, N-dodecylsulfamoyl, N-decylsulfamoyl, N, N-tert-butylmethylsulfamoyl group, N, N-phenylmethylsulfamoyl group, and the group represented by the following formula, etc. A halogen atom (preferably a chlorine atom), or a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or an inducible group thereof (e.g., a carboxyl group, a sulfo group, a nitro group, A sulfamoyl group substituted by an alkylsulfamoyl group (preferably octylsulfamoyl group) or the like);

Formylamino group; (2-ethyl) hexanoylamino group, heptanoylamino group, octanoylamino group, octanoylamino group, octanoylamino group, octanoylamino group, acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (Preferably having 1 to 12 carbon atoms) such as an amino group, a decanoylamino group, an undecanoylamino group, a dodecanoylamino group, a hecinocanoylamino group, a benzoylamino group and the like and a group represented by the following formula (For example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) (When the carbonylamino group is an alkanoylamino group, the number of carbon atoms is preferably 1 to 12);

A hydroxy group;

A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom;

A carboxyl group, -CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); Sulfo group, -SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); A nitro group; Cyano;

Formyloxy group; (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, naphthoyloxy group, propanoyloxy group, butanoyloxy group, 2,2- (Preferably having 1 to 20 carbon atoms, such as 1 to 20 carbon atoms, such as a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, A halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an alkylsulfamoyl group having 1 to 10 carbon atoms, preferably octylsulfamoyl group, A carbonyloxy group bonded to the carbonyloxy group (when the carbonyloxy group is an alkanoyloxy group, the number of carbon atoms is preferably 1 to 10);

(2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, an isopropylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, (Preferably having 1 to 10 carbon atoms) such as a silyl group, a sulfonyl group, a dodecylsulfonyl group, an icosylsulfonyl group, a phenylsulfonyl group and a p-tolylsulfonyl group, and a group represented by the following formula (Preferably an octylsulfamoyl group) of 1 to 10 carbon atoms, or the like, or an imidizing group (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen A substituted sulfonyl group;

Carbamoyl group;

An N, N-dimethylcarbamoyl group, an N-ethylcarbamoyl group, an N, N-diethylcarbamoyl group, an N-propylcarbamoyl group, An N, N-diisopropylcarbamoyl group, an N, N-diisopropylcarbamoyl group, an N, N-dibutylcarbamoyl group, Butylcarbamoyl group, N, N-di-tert-butylcarbamoyl group, N-sec-butylcarbamoyl group, N, (1-ethylpropyl) carbamoyl group, an N-hexylcarbamoyl group, an N, N-diethylcarbamoyl group, (2-ethyl) hexylcarbamoyl group, an N-heptylcarbamoyl group, an N, N-diheptylcarbamoyl group, An N-octylcarbamoyl group, an N, N-dioctylcarbamoyl group, an N-nonylcarbamoyl group, an N, An N, N-diphenylcarbamoyl group, an N, N-ethylmethylcarbamoyl group, an N, N-diethylcarbamoyl group, , N, N-isopropylmethylcarbamoyl, N, N-butylmethylcarbamoyl, N-decylcarbamoyl, N, N-decylmethylcarbamoyl, N N-dodecylcarbamoyl group, N-eicosylcarbamoyl group, N, N-eicosylcarbamoyl group, N, N-dodecylcarbamoyl group, An N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group and the like, and groups represented by the following formulas and the like, preferably 1 to 20 carbon atoms A halogen group (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (such as an alkyl group having 1 to 10 carbon atoms, Advantageously oxide tilsul sulfamoyl group) such as a carbamoyl group substituted by a group derivatized) by;

A perfluorohexyl group, a perfluoroheptyl group, a perfluorohexyl group, a perfluorohexyl group, a perfluorohexyl group, a perfluorohexyl group, a perfluorohexyl group, a perfluorohexyl group, And all of the hydrogen atoms of the perfluoroalkyl group, the perfluoroalkyl group, the perfluoroalkyl group, the perfluoroalkyl group, the perfluoroalkyl group, the perfluoroalkyl group, A hydrocarbon group of 1 to 20 carbon atoms substituted with a fluorine atom;

A perfluorohexylmethyl group, a perfluorooctylmethyl group, a perfluorooctylmethyl group, a perfluorohexylmethyl group, a perfluorohexylmethyl group, a perfluorohexylmethyl group, a perfluorohexylmethyl group, a perfluorohexylmethyl group, a perfluorohexylmethyl group, A straight chain or branched alkyl group having 1 to 20 carbon atoms in which all of the hydrogen atoms of the perfluorodecylmethyl group, the perfluorodecylmethyl group, the perfluorododecylmethyl group, and the perfluorooctylmethyl group are substituted by a fluorine atom, A hydrocarbon group of 1 to 20 carbon atoms substituted with a branched alkyl group;

(Preferably having 1 to 20 carbon atoms) substituted by fluorine with a part of hydrogen atoms such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group and a 2,4,6- A hydrocarbon group of 1 to 10 carbon atoms;

-CO-SH, -CO-S- CH 3, -CO-S-CH 2 CH 3, -CO-S-CH 2 -CH 2 -CH 3, -CO-S-CH 2 -CH 2 -CH 2 A thiocarbonyl group bonded with an aryl group having 6 to 20 carbon atoms such as a thiocarbonyl group bonded with an alkyl group having 1 to 20 carbon atoms (preferably 2 to 10 carbon atoms) such as -CH ₃ , -CO-SC ₆ H ₅ or the like;

(Wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those having 1 to 20 carbon atoms among the hydrocarbon groups listed above), as represented by the following formula: ???????? - , Or an imidizing group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) Or a group of

-NRCONR ₂ wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those having 1 to 20 carbon atoms among the hydrocarbon groups listed above), a group represented by the following formula: Or a derivative thereof which is derivatized with an inducible group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) Group, which may be the same or different and may be bonded to each other to form a ring;

-OCONR ₂ (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those having 1 to 20 carbon atoms among the hydrocarbon groups listed above), a group represented by the following formula: Or a derivative thereof which is derivatized with an inducible group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) Group may be the same or different and may be bonded to each other to form a ring);

(Wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a group represented by the following formula: * -NRCOOR A group derivatized with an imidizing group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkyl sulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) ), The R's may be the same or different and may be bonded to each other to form a ring;

_{* -OP (O) (OCH 3} ) 2 , etc. * -OP (O) (OR) 2 ( wherein, R is an example of the hydrocarbon group (for example, a hydrogen atom, having 1 to 20 carbon atoms, the hydrocarbon groups listed in A halogen atom (preferably a chlorine atom) and an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxy group, And octylsulfamoyl group), and the Rs may be the same or different and may be bonded to each other to form a ring;

_{* -Si (CH 3) 3,} * -Si (CH 2 CH 3) 3, * -Si (C 6 H 5) 3 and _{* -Si (CH (CH 3)} 2) , such as ₃ * -SiR ₃ ( In the formulas, R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or an inducible group thereof (e.g., a carboxy group, A halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group)), and the R may be the same or different from each other Which may be bonded to each other to form a ring; And the like.

Examples of the divalent substituent include an oxo group, a thioxo group, an imino group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), an imino group substituted with an aryl group having 6 to 20 carbon atoms, . Examples of the imino group substituted with an alkyl group include CH ₃ -N═, CH ₃ -CH ₂ -N═, CH ₃ - (CH ₂ ) ₂ -N═ and CH ₃ - (CH ₂ ) ₃ -N═ have. Examples of the imino group substituted with an aryl group include C ₆ H ₅ -N═.

The substituent of the hydrocarbon group of 1 to 40 carbon atoms is preferably a substituent of the group s1. The inducible group shown below is preferably a group induced by a carboxyl group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) Do.

[Group s1]

An oxy group in which a hydrocarbon group of 1 to 20 carbon atoms or its derivatizing group is bound on one side;

A hydrocarbon group having 1 to 20 carbon atoms or a carbonyl group to which the derivatizing group is bonded;

A hydrocarbon group of 1 to 20 carbon atoms or an oxycarbonyl group to which an acyl group is bonded;

An amino group;

An amino group substituted by one or two hydrocarbon groups of 1 to 20 carbon atoms or its derivatizing group;

Sulfamoyl group;

A sulfamoyl group substituted by one or two hydrocarbon groups of 1 to 20 carbon atoms or its derivatizing group;

A carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or an imidizing group thereof is bonded;

A hydroxy group; A halogen atom; -CO ₂ M (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO ₃ M (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); A nitro group; Cyano;

A carbonyloxy group bonded with a hydrocarbon group having 1 to 20 carbon atoms or its derivatizing group;

A sulfonyl group bonded with a hydrocarbon group having 1 to 20 carbon atoms or its derivatizing group;

Carbamoyl group;

A carbamoyl group substituted by one or two hydrocarbon groups of 1 to 20 carbon atoms or its derivative group;

A hydrocarbon group of 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms;

A hydrocarbon group of 1 to 20 carbon atoms substituted with a linear or branched alkyl group of 1 to 20 carbon atoms in which all of the hydrogen atoms are substituted by fluorine atoms;

A hydrocarbon group of 1 to 20 carbon atoms in which a part of the hydrogen atoms are substituted with fluorine; An oxo group;

The substituent of the hydrocarbon group of 1 to 40 carbon atoms is more preferably a substituent of the group s2.

[Group s2]

An oxy group in which a hydrocarbon group of 1 to 10 carbon atoms or its derivatizing group is bonded;

A hydrocarbon group having 1 to 10 carbon atoms or a carbonyl group to which the derivatizing group is bonded;

A hydrocarbon group of 1 to 10 carbon atoms or an oxycarbonyl group to which the inducible group is bonded;

An amino group;

An amino group substituted by one or two hydrocarbon groups having 1 to 10 carbon atoms or an imidizing group thereof;

Sulfamoyl group;

A sulfamoyl group substituted by one or two hydrocarbon groups of 1 to 10 carbon atoms or its derivatizing group;

A carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a group derived therefrom is bonded;

A hydroxy group; Fluorine atom, chlorine atom, bromine atom;

-CO ₂ M (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom);

-SO ₃ M (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom);

A nitro group; Cyano;

A carbonyloxy group bonded with a hydrocarbon group of 1 to 10 carbon atoms or its derivatizing group;

A hydrocarbon group having 1 to 10 carbon atoms or a sulfonyl group bonded with an imidizing group thereof;

Carbamoyl group;

A carbamoyl group substituted by one or two hydrocarbon groups of 1 to 10 carbon atoms or its derivatizing group; A hydrocarbon group of 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms;

A hydrocarbon group of 1 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms in which all of the hydrogen atoms are substituted by fluorine atoms;

A hydrocarbon group having 1 to 10 carbon atoms in which a part of the hydrogen atoms are substituted with fluorine;

Oxo group.

Examples of the hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include a hydrocarbon group having 1 to 40 carbon atoms and having a monovalent or divalent substituent Preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and a monovalent or divalent substituent, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms having a monovalent or divalent substituent, 1 An aromatic hydrocarbon group having 6 to 30 carbon atoms or a combination of hydrocarbon groups having 1 to 20 carbon atoms or a divalent substituent and 1 to 30 carbon atoms having a monovalent or divalent substituent,

More preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent group of the group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent group of the group s1, An aromatic hydrocarbon group or a hydrocarbon group in combination with a substituent of the group s1 and a group having 1 to 20 carbon atoms having a substituent of the group s1,

Particularly preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of the group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent group of the group s2, An aromatic hydrocarbon group or a hydrocarbon group, and the group having 1 to 15 carbon atoms having a substituent of the group s2.

The heterocyclic group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may be either a monocyclic ring or a polycyclic ring, preferably a heterocyclic ring containing a hetero atom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom and a sulfur atom.

The carbon number of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, still more preferably 3 to 20, still more preferably 3 to 18, still more preferably 3 to 15 And particularly preferably from 3 to 14.

As the heterocyclic ring containing a nitrogen atom,

Monocyclic saturated heterocyclic rings such as aziridine, acetidine, pyrrolidine, piperidine and piperazine;

A pyrazole such as pyrrole such as 2,5-dimethylpyrrole, 2-methylpyrazole or 3-methylpyrazole, a 5-membered ring such as imidazole, 1,2,3-triazole or 1,2,4- A systematic unsaturated heterocyclic ring;

6-membered cyclic unsaturated heterocyclic rings such as pyridine, pyridazine, pyridazine, 6-methylpyrimidine and the like, pyrazine and 1,3,5-triazine;

Quinoxine such as indazole, indoline, isoindoline, indole, indolizine, benzoimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro (3-methyl) quinoxaline and 3-methylquinoxaline Condensed divalent heterocyclic rings such as salin, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperidine;

Condensed tricyclic heterocyclic rings such as carbazole, acridine and phenazine; And the like.

As the heterocyclic ring containing an oxygen atom,

Monocyclic saturated heterocyclic rings such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane;

Bicyclic saturated heterocyclic rings such as 1,4-dioxaspiro [4.5] decane and 1,4-dioxaspiro [4.5] nonane;

lactone type heterocyclic rings such as? -acetolactone,? -propiolactone,? -butyrolactone,? -valerolactone and? -valerolactone;

5-membered cyclic unsaturated heterocyclic rings such as 2,3-dimethyl furan and furan such as 2,5-dimethyl furan;

6-membered cyclic unsaturated heterocyclic rings such as 2H-pyran and 4H-pyran;

Condensed divalent heterocyclic rings such as benzopyran, benzodioxole, chroman, isochromane such as 1-benzofuran and 4-methylbenzopyran;

Condensed tricyclic heterocyclic rings such as xanthene and dibenzofuran; And the like.

As the heterocycle containing a sulfur atom,

5-membered cyclic saturated heterocyclic rings such as dithiolane;

6-membered cyclic saturated heterocyclic rings such as thian, 1,3-dithiane, and 2-methyl 1,3-dithiane;

5-membered cyclic unsaturated heterocyclic rings such as thiophene such as 3-methylthiophene or 2-carboxythiophene, benzothiopyrane such as 4H-thiopyran or benzotetrahydrothiopyran;

Condensed divalent heterocyclic rings such as benzothiophene and the like;

Condensed tricyclic heterocyclic rings such as thianthrene, dibenzothiophene and the like; And the like.

As the heterocyclic ring containing a nitrogen atom and an oxygen atom,

Monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone;

Oxazole such as 4-methyloxazole, isooxazole such as 2-methylisooxazole and 3-methylisoxazole, and other monocyclic unsaturated heterocyclic rings;

Condensed divalent heterocyclic rings such as benzooxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline;

Condensed tricyclic heterocyclic rings such as phenoxazin; And the like.

As the heterocyclic ring containing a nitrogen atom and a sulfur atom,

Monocyclic heterocyclic rings such as thiols such as 3-methylthiazole and 2,4-dimethylthiazole;

Condensed divalent heterocyclic rings such as benzothiazole;

Condensed tricyclic heterocyclic rings such as phenothiazine; And the like.

The heterocyclic ring may be a combination of the hydrocarbon groups listed above, and includes tetrahydrofurylmethyl.

Other heterocycles may be represented by the following groups.

The heterocyclic group may be a heterocyclic group formed by combining two or more of R ¹ to R ⁵ . Such a heterocyclic group has two or more ring structures together with a benzene ring to which R ¹ to R ⁵ are bonded. As the ring structure of two or more rings, for example, a structure of the following formula can be given.

The bonding position of the above-mentioned heterocyclic ring is a portion in which any hydrogen atom contained in each ring is eliminated.

The heterocyclic group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have a substituent. The substituent may be the same as the substituent which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have. When the heterocyclic ring contains a nitrogen atom as a constituent element, the hydrocarbon atom listed above may be bonded to the nitrogen atom as a substituent.

Preferable examples of the substituents include the same ones as those preferred among the substituents which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

Examples of the heterocyclic group having a substituent represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include a monovalent or divalent heterocyclic group having a substituent, , And more preferably a heterocyclic group having a substituent of the group s2.

The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be one or two or more, and two or more substituents may be the same or different. The first substituent may be bonded to a hydrocarbon group contained in a part thereof with another substituent (second substituent). The second substituent may be selected from the same group as the first substituent.

Hereinafter, R ¹ to R ⁵ , R ¹² , R ^{13 -CO-R 102, -COO-R} 101, -OCO-R 102, -COCO-R 102, -OR 102, -SO 2 -R 101, -SO 2 N (R 102) 2, -CON (R 102 ) to _{^{2, -N (R 102) 2}} , -NHCO-R 102, -NHCON (R 102) 2, -NHCOOR 102, -OCON (R 102) 2, a halogen atom, -SO ₃ M, -CO ₂ M .

Examples of -CO-R ¹⁰² include formyl; (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, an acetyl group, an acetyl group, a propanoyl group, a butanoyl group, a 2,2-dimethylpropanoyl group, a pentanoyl group, a hexanoyl group, , A dodecanoyl group, a hecinocanoyl group, a benzoyl group, etc., and a group represented by the above formula such as a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or an inducible group thereof (for example, a carboxy group A group derived from a sulfone group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) -CO-R ¹⁰² in the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b), and Tables 10 to 11 And the like, more preferably having 1 to 11 carbon atoms A carbonyl group to which an acyl group is bonded, an acyl group having a carbon number of 1 to 10, a carbonyl group to which the acyl group is bonded, more preferably 2 to 12), and the following Tables 1 to 8, Examples of the group represented by -CO-R ¹⁰² in the compounds represented by the formulas (a), (b) and (c) are shown below.

Examples of -COO-R ¹⁰¹ include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl) hexyloxycarbonyl group, (Preferably having 1 to 20 carbon atoms, such as an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, an icosyloxycarbonyl group, A halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having a carbon number of 1 to 10 (preferably an oxo group having a carbon number of 1 to 20), a carboxyl group, a sulfo group, a nitro group, And oxycarbonyl groups to which a group derived from the oxycarbonyl group introduced by the oxycarbonyl group, Where in the compound -COO-R and the like for the group ^102, more preferably from table 1 to the oxycarbonyl group, and the following combination of a hydrocarbon group having 1 to 10 carbon atoms or derivatization of Table 8, Table 9 ( a group corresponding to -COO-R ¹⁰² in the compounds shown in Table 9 (a), Table 9 (b) and Tables 10 to 11, and the like.

Examples of -OCO-R ¹⁰² include a formyloxy group; (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, naphthoyloxy group, propanoyloxy group, butanoyloxy group, 2,2- (Preferably one having 1 to 40 carbon atoms such as a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, A halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an alkylsulfamoyl group having 1 to 10 carbon atoms, preferably an octylsulfamoyl group, (When the carbonyloxy group is an acyloxy group, the number of carbon atoms is 2 to 41), and Tables 1 to 8, Tables 9 (a) and 9 ( b) and in the compounds shown in Tables 10 to 11, OCO-R ¹⁰² , and the like, more preferably a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a carbonyloxy group bonded to the derivatizing group (the carbonyloxy group And the number of carbon atoms is more preferably 2 to 12), and in the compounds shown in Tables 1 to 8, Tables 9 (a), 9 (b) and 10 to 11 below -OCO-R ¹⁰² , and the like.

Examples of -COCO-R ¹⁰² include a methyloxyl group, an ethyloxyl group, a propyloxyl group, a butyloxyl group, a pentyloxyl group, a hexyloxyl group, a (2-ethyl) hexyloxyl group, An octyloxyl group, a cyclopentyloxyl group, a cyclohexyloxyl group, a phenyloxyl group, a phenyloxycarbonyl group, a p-toluenesulfonyl group, a p-toluenesulfonyl group, (For example, a carboxy group, a sulfo group, a nitro group, a sulfo group, a nitro group, a sulfo group, a nitro group and the like) A group induced by a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group (preferably an octylsulfamoyl group) having 1 to 10 carbon atoms, and the oxalyl group bonded to the groups shown in Tables 1 to 8 and 9 (a), Table 9 (b) and it can be mentioned for the group -COCO-R ¹⁰² in the compounds shown in Table 10 to Table 11 .

-OR ¹⁰² includes a hydroxyl group; Butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, 2-ethylhexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2-ethylhexyloxy group, Dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, An alkoxycarbonyloxy group, an oxy group, a 2,2-dicyanophenyloxy group, a 2,3-dicyanophenyloxy group, a 2,4-dicyanophenyloxy group, a 2,5- A 3-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-methoxyphenyloxy group, a 4-methoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group, etc., and the above-mentioned formula (Such as a carboxyl group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), or a halogen atom (preferably a chlorine atom) Groups bonded to a group derived from an alkylsulfamoyl group (preferably octylsulfamoyl group) having 1 to 10 carbon atoms and the like) and an oxy group bonded to groups represented by Tables 1 to 8, Table 9 (a), Table 9 (b), and Table 10 And a group corresponding to -OR ¹⁰² in the compound shown in Table 11, more preferably an oxy group bonded with a hydrocarbon group having 1 to 10 carbon atoms or its derivatizing group, And groups corresponding to -OR ¹⁰² in the compounds shown in Tables 9 (a), 9 (b) and 10 - 11.

Examples of -SO ₂ -R ¹⁰¹ include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, (Preferably having 1 to 40 carbon atoms, such as a methyl group, an ethyl group, an ethyl group, an ethyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, A halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having a carbon number of 1 to 10 (preferably a hydrocarbon group having 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, Octylsulfamoyl group), and compounds represented by Tables 1 to 8, Tables 9 (a), 9 (b) and 10 to 11 in which -SO ₂ - And R < ¹⁰¹ >, and more preferably a hydrocarbon group having 1 to 10 carbon atoms A sulfonyl group bonded with a hydrogen group or an inducible group thereof, and a compound represented by -SO ₂ -R ¹⁰¹ in the compounds shown in Tables 1 to 8, 9 (a), 9 (b) and 10 - And the like.

Examples of -SO ₂ N (R ¹⁰² ) ₂ include a sulfamoyl group;

N-isopropylsulfamoyl group, N-methylsulfamoyl group, N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-hexylsulfamoyl group, N- (2-ethyl) hexylsulfamoyl group, N-heptylsulfamoyl group, N-heptylsulfamoyl group, N- N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-desilsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamoyl group, N (E.g., a carboxy group, a sulfo group, a nitro group, a nitro group, a cyano group, a cyano group, a cyano group, A sulfamoyl group substituted by a halogen atom, a hydroxy group, a halogen (preferably a chlorine atom), a group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) Groups corresponding to -SO ₂ N (R ¹⁰² ) ₂ in the compounds shown in Tables 1 to 8, Tables 9 (a), 9 (b), and 10 to 11;

N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, , N, N-diisopropylsulfamoyl group, N, N-diisopropylsulfamoyl group, N, N-tert-butylmethylsulfamoyl group, N, N-dibutylsulfamoyl group, N, N-dipentylsulfamoyl group, N, N-dibutylsulfamoyl group, Di (2-ethyl) hexylsulfamoyl group, N, N-diheptylsulfamoyl group, N, N-octyl Methylsulfamoyl group, N, N-dioctylsulfamoyl group, N, N-dinylsulfamoyl group, N, N-decyl methyl sulfamoyl group, N, N-undecyl methyl sulfamoyl group, N, Methylsulfamoyl group, N, N-eicosylmethylsulfamoyl group, N, N-phenylmethylsulfamoyl group, N, N-diphenylsulfamoyl group and the like, 1 ~ A halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably having 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, (Preferably octylsulfamoyl group), and the sulfamoyl group substituted by a sulfamoyl group substituted by a sulfamoyl group substituted by a sulfamoyl group substituted by a sulfamoyl group substituted by a sulfamoyl group And a group corresponding to -SO ₂ N (R ¹⁰² ) ₂ in the compound, more preferably a sulfamoyl group substituted by one or two hydrocarbon groups of 1 to 10 carbon atoms or its derivative, and And groups corresponding to -SO ₂ N (R ¹⁰² ) ₂ in the compounds shown in Tables 1 to 8, Tables 9 (a), 9 (b) and 10 to 11 below.

Examples of -CON (R ¹⁰² ) ₂ include a carbamoyl group;

N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec- (1-ethylpropyl) carbamoyl group, an N-hexylcarbamoyl group, an N- (2-ethyl) hexylcarbamoyl group, an N-butylcarbamoyl group, Heptylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group, N-nonylcarbamoyl group, N-decylcarbamoyl group, N- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or an inducible group thereof (e.g., a carboxy group, a sulfo group, a mercapto group, A nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) (R ¹⁰² ) ₂ in the compounds shown in Tables 1 to 8, Tables 9 (a), 9 (b) and 10 to 11 and the carbamoyl groups substituted by -CON Applicable equipment;

An N, N-dimethylcarbamoyl group, an N, N-dimethylcarbamoyl group, an N, N-ethylmethylcarbamoyl group, N, N-diisopropylcarbamoyl group, N, N-diisopropylcarbamoyl group, N, N-diisopropylcarbamoyl group, An N, N-dibutylcarbamoyl group, an N, N-butyloctylcarbamoyl group, an N, N-dibutylcarbamoyl group, N-di (2-ethyl) hexylcarbamoyl group, N, N-di (1-ethylpropyl) carbamoyl group, N, N-dodecylcarbamoyl, N, N-dodecylcarbamoyl, N, N-dodecylcarbamoyl, N, N-octylmethylcarbamoyl, N, N-dodecylmethylcarbamoyl, N, N-eicosylmethylcarbamoyl, N, N-phenylmethylcarbamoyl , An N, N-diphenylcarbamoyl group, and the like, and groups represented by the above formulas, or a condensed hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or its derivatizing group (for example, A carbamoyl group substituted by a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) And groups corresponding to -CON (R ¹⁰² ) ₂ in the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b), and Tables 10 to 11, Is a carbamoyl group substituted by one or two hydrocarbon groups of 1 to 10 carbon atoms or its derivatizing group and the following carbamoyl groups substituted by the following Tables 1 to 8, Tables 9 (a), 9 (b) and 10 to 11 In the compound represented by -CON (R ¹⁰² ) ₂ , and the like.

Examples of -N (R ¹⁰² ) ₂ include an amino group;

N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, , N-hexylamino group, N- (2-ethyl) hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, (Preferably having 1 to 20 carbon atoms) or its derivatizing group (for example, a carboxyl group, a sulfone group, a sulfamoyl group, a sulfamoyl group, An amino group substituted by a halogen atom, a halogen atom, a halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) In the compounds shown in Table 8, Table 9 (a), Table 9 (b) and Table 10 to Table 11 -N (R ¹⁰²⁾ group for the _second, and the like;

N, N-dimethylamino group, N, N-ethylmethylamino group, N, N-diethylamino group, N, N-propylmethylamino group, Diisopropylamino group, N, N-tert-butylmethylamino group, N, N-diisobutylamino group, N, Diethylamino group, N, N-diethylamino group, N, N-di (2-ethyl N-dodecylamino group, N, N-dodecylmethylamino group, N, N-undecylmethylamino group, N, N-dodecylamino group, N, N-diphenylamino group, N, N-diphenylamino group, etc., and the group represented by the above formula, and the like, preferably having 1 to 40 carbon atoms A hydrocarbon group having 1 to 20 carbon atoms) or an inducible group thereof (e.g., carboxy An amino group substituted by a halogen atom, a halogen atom, a halogen atom, a halogen atom (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) A group corresponding to -N (R ¹⁰² ) ₂ in the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b), and Tables 10 to 11; More preferably 1 or 2 amino groups substituted by a hydrocarbon group having 1 to 10 carbon atoms or its derivatizing group, and amino groups substituted by the following Tables 1 to 8, Tables 9 (a) and 9 (b) And groups corresponding to -N (R ¹⁰² ) ₂ in the compounds shown in Tables 10 to 11, and the like.

Examples of -NHCO-R ¹⁰² include a formylamino group; (2-ethyl) hexanoylamino group, heptanoylamino group, octanoylamino group, octanoylamino group, octanoylamino group, octanoylamino group, acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (Preferably having 1 to 20 carbon atoms) such as an amino group, a decanoylamino group, an undecanoylamino group, a dodecanoylamino group, a hecinocanoylamino group, a benzoylamino group, etc., (For example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) (Where the carbonylamino group is an acylamino group, the number of carbon atoms is 1 to 40), and Tables 1 to 8, Table 9 (a), Table 9 (b), and Table 1 -NHCO-R ¹⁰² in the compounds shown in the following formulas (1) to (11), and more preferably a hydrocarbon group having 1 to 10 carbon atoms or a carbonylamino group having the condensed carbamoyl group In the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b) and Tables 10 to 11, the number of carbon atoms in the compound represented by the formula NHCO-R ¹⁰² , and the like.

A -NHCON (R ¹⁰²⁾ ₂ Examples of groups which, in the open or the like, Tables 1 to 8, Table 9 (a), Table 9 (b), and -NHCONR ¹⁰² according to the compounds shown in Table 10 to Table 11 And the like.

Examples of -NHCOOR ¹⁰² include the groups listed above and the groups corresponding to -NHCOOR ¹⁰² in the compounds shown in Tables 1 to 8, Table 9 (a), Table 9 (b), and Tables 10 to 11 .

In -OCON (R ¹⁰²⁾ ₂ Examples of groups which, in the open or the like, Tables 1 to 8, Table 9 (a), Table 9 (b) and -OCONR ¹⁰² according to the compounds shown in Table 10 to Table 11 And the like.

As the halogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom are preferable.

As M of -SO ₃ M and -CO ₂ M, a hydrogen atom; And alkali metal atoms such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.

-CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON _{^{102) 2, -N (R 102}} ) 2, -NHCO-R 102, -NHCON (R 102) 2, -NHCOOR 102, -OCON (R 102) substituents included in the _second (first substituent) is one Or two or more substituents may be present, and two or more substituents may be the same or different.

The first substituent may be bonded to a hydrocarbon group contained in a part thereof with another substituent (second substituent). The second substituent may be selected from the same group as the first substituent.

The ring formed by R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ is condensed with the benzene ring of the isoindoline skeleton of formula (I). Examples of the condensed ring structure of the ring formed by R ² and R ³ , R ³ and R ⁴ , or R ⁴ and R ⁵ and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, N-methylphthalimide, N- (1-phenylethyl) phthalimide, tetracene, tetracene, and the like can be used in combination with one or more selected from the group consisting of naphthalene, phenanthrene, anthracene, fluoranthene, (For example, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); Indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carbolin, phenanthridine, acridine, perimidine, phenanthroline, Nitrogen containing condensed heterocyclic ring and its partially reduced form; 3-hydrobenzofuran-2-one and the like, and partially reduced forms thereof.

When R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ form a ring, the ring may have a substituent. The substituent may be the same as the substituent which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have. Preferable examples of the substituents include the same ones as those preferred among the substituents which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

When R ³ and R ⁴ form a ring, R ² and R ⁵ are each independently preferably a hydrogen atom, an amino group or a hydroxy group.

When R ² and R ³ are forming a ring is, R ⁴ and R ⁵ are, and preferably does not form a ring, it is more preferable that R ⁴ and R ⁵ are hydrogen atoms.

In addition, if the R ⁴ and R ⁵ may form a ring, R ² and R ³ is preferably that does not form a ring, more preferably R ² and R ³ is a hydrogen atom.

The ring that forms the R ¹² and R ^13, formula (Ⅰ) isophthalic in and bonded turned and exo-methylene (C = CH ₂₎ skeleton, R ¹² and R ¹³ the ring is formed with the exo-methylene (C = CH of ₂ ), for example, a structure in which a carbonyl group such as the following Group A and Group B, and an exomethylene and a carbonyl group are arranged in this order can be exemplified. ** represents the binding to the isoindoline skeleton.

[A]

[Group B]

R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁷ independently represent a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -OR ¹⁰² , -COCO-R ¹⁰² , -SO _{^{2 -R 101, -SO 2 N (}} R 102) 2, -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102 , -OCON (R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent .

R ¹⁰⁴ and R ¹⁰⁵ are, independently, a hydrogen ^{atom, -CO-R 102, -COO-} R 101, -OCO-R 102, -OR 102, -SO 2 -R 101, -SO 2 N (R 102 together ^{_{) 2, -CON (R 102)}} 2, -N (R 102) 2, -NHCO-R 102, a halogen atom, a cyano group, a nitro _{group, -SO 3 M, -CO 2 M} , carbon atoms which may have a substituent A hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group which may have a substituent.

R ^104, R ^105, represented by R ¹⁰⁶ and ^{R 107, -CO-R 102,} -COO-R 101, -OCO-R 102, -OR 102, -COCO-R 102, -SO 2 -R 101, _{^{-SO 2 N (R 102) 2}} , -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102, -OCON (R ¹⁰²⁾ _2, a halogen atom, -SO ₃ M and -CO ₂ M, a heterocyclic group which may have a hydrocarbon group or substituent of 1 to 40 carbon atoms which may have a substituent, R ¹ ~R ^5, R ¹² and R ¹³ -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -OR ¹⁰² , -COCO-R ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R ¹⁰² ) ₂ , -CON _{^{(R 102) 2, -N (}} R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102, -OCON (R 102) 2, a halogen atom, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^104, there may be mentioned R ^105, R ¹⁰⁶ and R ¹⁰⁷ preferred examples, R ¹ ~R ^5, R ¹² and R ¹³ in the preferred group.

R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ and R ¹⁰⁷ independently represent a methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, pentyl group, hexyl group, A hydrocarbon group having 1 to 10 carbon atoms such as a heptyl group, an octyl group, a nonyl group, a cyclohexyl group and a phenyl group, or a hydrogen atom.

The groups exemplified in the groups A and B may have a hydrogen atom bonded to the ring structure substituted by a substituent.

The substituent may be the same as the substituent which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

Of the substituents, preferable examples of the substituents which may be contained in the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² include the same ones as those preferred.

It is preferable that R ¹ is a hydrogen atom and R ² to R ⁵ are independently of each other a hydrogen atom or a nitro group.

Examples of the groups A and B include rings represented by formulas (QQ1) to (QQ25).

When R ¹² and R ¹³ do not form a ring, the compound (I) may be a compound represented by the formula (I-a) (hereinafter sometimes referred to as a compound (I- (Hereinafter sometimes referred to as a compound (II-a)), a compound represented by the formula (II-a0) (hereinafter sometimes referred to as compound (II-a1)), and more preferably a compound represented by formula (I-a).

[In the formula (I-a), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.

L ² represents -CO- or -SO ₂ -.

R ¹⁴ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.]

Examples of the hydrocarbon group having 1 to 40 carbon atoms which may have a substituent and the heterocyclic group which may have a substituent represented by R ¹⁴ include a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent represented by R ¹¹ and R ¹⁰¹ , The same as the heterocyclic group which may be contained.

R ¹⁴ is preferably a group the same as the preferred group among R ¹¹ and R ¹⁰¹ .

In the compound (I-a), R ¹¹ and R ¹⁴ are preferably the same group.

It is preferable that L ¹ and L ² are the same group.

R ¹¹ and R ¹⁴ each independently represent an alkyl group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, A pyridinyl group optionally having a substituent, a thienyl group optionally having a substituent, a furyl group optionally having a substituent, or a pyridinyl group optionally having a substituent.

The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 8.

The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the pyridinyl group, the thienyl group, the furyl group and the alkyl group may have a substituent. These groups may have an alkyl group instead of a substituent.

The substituent may be the same as the substituent which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

Preferable examples of the substituent include the same ones as those preferred among the substituents which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

The naphthyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, the furyl group and the alkyl group which may be bonded to the pyridinyl group, or the phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, The substituent of the furyl group and the pyridinyl group is preferably a group having 1 to 10 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl, An alkyl group; A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; A trifluoromethyl group; An oxycarbonyl group bonded with a hydrocarbon group of 1 to 10 carbon atoms; A nitro group; A hydroxy group; Sulfamoyl group; -SO ₃ M; -CO2M. ≪ / _RTI >

Examples of the substituent of the alkyl group include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; A hydroxy group; -SO ₃ M; -CO2M. ≪ / _RTI >

L ¹ is preferably -CO-.

L ² is preferably -CO-.

R ¹ is preferably a hydrogen atom.

It is preferable that R ² to R ⁵ independently represent a hydrogen atom, a halogen atom or a nitro group. The halogen atom is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. R ³ or R ⁴ is preferably a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. R ³ or R ⁴ is preferably a nitro group.

[In the formula (II), R ¹ to R ⁵ , R ¹¹ to R ¹³ and the broken line each have the same meaning as defined above.]

R ¹¹ represents a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a pyridinyl group which may have a substituent, a thienyl group which may have a substituent, Or an alkyl group which may have a substituent. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 8.

The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the pyridinyl group, the thienyl group, the furyl group and the alkyl group may have a substituent. These groups may have an alkyl group instead of a substituent.

The substituent may be the same as the substituent which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

Preferable examples of the substituent include the same ones as those preferred among the substituents which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

The naphthyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, the furyl group and the alkyl group which may be bonded to the pyridinyl group, or the phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, The substituent of the furyl group and the pyridinyl group is preferably a group having 1 to 10 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl, An alkyl group; A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; A trifluoromethyl group; An oxycarbonyl group bonded with a hydrocarbon group of 1 to 10 carbon atoms; A nitro group; A hydroxy group; Sulfamoyl group; -SO ₃ M; -CO2M. ≪ / _RTI >

Examples of the substituent of the alkyl group include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; A hydroxy group; -SO ₃ M; -CO2M. ≪ / _RTI >

R ¹ is preferably a hydrogen atom.

It is preferable that R ² to R ⁵ independently represent a hydrogen atom, a halogen atom or a nitro group. The halogen atom is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. R ³ or R ⁴ is preferably a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. R ³ or R ⁴ is preferably a nitro group.

R ¹² is preferably -CO-R ¹⁰² or -SO ₂ -R ¹⁰¹ . And R ¹² is more preferably -CO-R ¹⁰² .

R ¹³ is preferably a cyano group.

R ¹⁰¹ and R ¹⁰² each have the same meaning as defined above.

The compound (I) is preferably a compound represented by the formula (II-a0) (hereinafter sometimes referred to as a compound (II-a0)).

[In the formula (II-a0), R ¹ to R ⁵ , R ¹² to R ¹³ and the broken line have the same meanings as defined above, respectively.

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ may be bonded to each other to form a ring.

However, R ¹² and R ^13, one of which is a cyano group, R ¹² and R ¹³ is again one of the, -SO ₂ cases caused represented by -R ^223, R ² ~R at least one of R ⁵ is ^{-CO-102 , -COO-R 101, -OCO-} R 102, -COCO-R 102, -OR 102, -SO 2 -R 101, -SO 2 N (R 102) 2, -CON (R 102) 2, -N _{^{(R 102) 2, -NHCO-}} R 102, -NHCO-N (R 102) 2, -NHCOOR 102, -OCON (R 102) 2, a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent, and when R ² and R ³ form a ring, R ⁴ and R ⁵ do not form a ring.

R ²²² represents a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent.

R ²²³ is the same as R ²²² .

M represents a hydrogen atom or an alkali metal atom.

When a plurality of R ¹⁰¹ , R ¹⁰² and M exist, they may be the same or different.

Examples of the hydrocarbon group having 1 to 40 carbon atoms which may have a substituent represented by R ²²² include the same hydrocarbon groups as those having 1 to 40 carbon atoms and may have a substituent represented by R ¹¹ .

As a preferable group of the hydrocarbon group having 1 to 40 carbon atoms which may have a substituent and represented by R ²²² , a preferable group out of hydrocarbon groups having 1 to 40 carbon atoms and may have a substituent represented by R ¹¹ is exemplified.

R ²²² is preferably a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent or an alkyl group which may have a substituent. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 8.

The phenyl group, the naphthyl group, the tetrahydronaphthyl group and the alkyl group may have a substituent. These groups may have an alkyl group instead of a substituent.

The substituent may be the same as the substituent which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

Preferable examples of the substituents include the same ones as those preferred among the substituents which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

The substituent of the phenyl group, the naphthyl group, the alkyl group which may be bonded to the tetrahydronaphthyl group, the phenyl group, the naphthyl group, and the tetrahydronaphthyl group may be the same or different and each represents a methyl group, an ethyl group, a propyl group, an isopropyl group, an alkyl group having 1 to 10 carbon atoms such as a sec-butyl group, a tert-butyl group, a hexyl group, a (2-ethyl) hexyl group and an octyl group; A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; A trifluoromethyl group; An oxycarbonyl group bonded with a hydrocarbon group of 1 to 10 carbon atoms; A nitro group; A hydroxy group; Sulfamoyl group; -SO ₃ M; -CO2M. ≪ / _RTI >

Examples of the substituent of the alkyl group include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; A hydroxy group; -SO ₃ M; -CO2M. ≪ / _RTI >

R ¹ is preferably a hydrogen atom.

It is preferable that R ² to R ⁵ independently represent a hydrogen atom, a halogen atom or a nitro group. The halogen atom is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. R ³ or R ⁴ is preferably a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. R ³ or R ⁴ is preferably a nitro group.

R ¹² is preferably -CO-R ¹⁰² or -SO ₂ -R ¹⁰¹ . And R ¹² is more preferably -SO ₂ -R ¹⁰¹ .

R ¹³ is preferably a cyano group.

R ¹⁰¹ and R ¹⁰² each have the same meaning as defined above.

The compound (I) is preferably a compound represented by the formula (II-a1) (hereinafter sometimes referred to as a compound (II-a1)).

[In the formula (II-a1), R ¹ to R ⁵ , R ¹² to R ¹³ and the broken line have the same meanings as defined above, respectively.

R ¹¹¹ represents a heterocycle which may have a substituent.]

Examples of the heterocyclic group which may have a substituent represented by R < ¹¹¹ &^gt; include the same as the heterocyclic group which may have a substituent represented by R < ¹¹ >.

Among the heterocyclic groups which may have a substituent represented by R < ^{111 &} gt ;, those preferable examples of the heterocyclic group which may have a substituent represented by R < ^{11 &}

R ¹¹¹ is preferably a pyridinyl group, a thienyl group or a furyl group which may have a substituent.

The pyridinyl group, the thienyl group and the furyl group may have a substituent. These groups may have an alkyl group instead of a substituent.

As the substituent, there can be mentioned the same group as the substituent which the hydrocarbon group represented by R ¹¹ may have.

Preferable examples of the substituent include the preferred ones of the substituents which the hydrocarbon group represented by R ¹¹ may have.

The thienyl group, the furyl group and the alkyl group which may be bonded to the pyridinyl group, or the thienyl group, the furyl group and the pyridinyl group of the pyridinyl group may be the same or different and are preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, An alkyl group having 1 to 10 carbon atoms such as a butyl group, a hexyl group, a (2-ethyl) hexyl group and an octyl group; A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom;

A trifluoromethyl group; An oxycarbonyl group bonded with a hydrocarbon group of 1 to 10 carbon atoms; A nitro group; A hydroxy group; Sulfamoyl group;

-SO ₃ M; -CO2M. ≪ / _RTI >

R ¹² is preferably -CO-R ¹⁰² or -SO ₂ -R ¹⁰¹ . And R ¹² is more preferably -SO ₂ -R ¹⁰¹ . R ¹⁰¹ and R ¹⁰² each have the same meaning as defined above.

R ¹³ is preferably a cyano group.

R ¹ is preferably a hydrogen atom.

It is preferable that R ² to R ⁵ independently represent a hydrogen atom, a halogen atom or a nitro group. The halogen atom is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. R ³ or R ⁴ is preferably a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. R ³ or R ⁴ is preferably a nitro group.

When R ¹² and R ¹³ form a ring, the compound (I) is preferably a compound represented by the formula (I-b) (hereinafter sometimes referred to as a compound (I-b)).

[In the formula (I-b), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.

R ²⁰ and R ³⁰ combine to form a ring Q.

The ring Q may have a substituent, a ring having 5 to 7 ring members, and the ring Q may be a hydrocarbon ring or a heterocyclic ring. The ring Q may be a monocyclic ring having 5 to 7 ring members selected from a hydrocarbon ring and a heterocyclic ring, or an axial ring condensed with the monocyclic ring may be bonded.

The constituent number of the ring is preferably 5 to 6 carbon atoms.

These monocyclic or polycyclic rings are preferably bonded at two positions to the ring Q to form a ring.

The ring Q and the ring to which the monocyclic or bicyclic ring is bonded may be the same as those of the above-mentioned groups A and B, and is preferably a ring represented by the formulas (QQ1) to (QQ25).

Among them, the ring represented by the formula (Q1), the formula (Q4), the formula (Q7), the formula (Q8) and the formula (Q18) (preferably the formula (QQ25) More preferably, it is a ring represented by formula (Q8), formula (Q18) (preferably formula (QQ25) in formula (Q18)).

A monocyclic ring which may have a substituent having 5 to 7 carbon atoms constituting the ring and a condensed ring formed by condensation of two or more of the monocyclic rings selected from a hydrocarbon ring and a heterocyclic ring which may be condensed with the ring Q and the ring Q, do. Examples of the substituent include the same groups as the substituent which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

Preferable examples of the substituent include preferred groups of the substituents which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

The compound (I-b) is more preferably a compound represented by the formula (I-c) (hereinafter sometimes referred to as a compound (I-c)).

[In the formula (I-c), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.

R ⁶ and R ⁷ independently represent a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , _{^{SO 2 N (R 102) 2}} , -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102, -OCON (R 102 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocycle which may have a substituent.

R ¹⁰¹ , R ¹⁰² and M have the same meanings as defined above.

R ⁶ and R ⁷ are, independently, a hydrogen ^{atom, -CO-R 102, -COO-} R 101, -OCO-R 102, -OR 102, -SO 2 -R 101, -SO 2 N (R 102 together ^{_{) 2, -CON (R 102)}} 2, -N (R 102) 2, -NHCO-R 102, a halogen atom, a cyano group, a nitro _{group, -SO 3 M, -CO 2 M} , carbon atoms which may have a substituent A hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic ring which may have a substituent.

R ⁶ and R ⁷ is represented ^{by, -CO-R 102, -COO-} R 101, -OCO-R 102, -OR 102, -COCO-R 102, -SO 2 -R 101, -SO 2 N (R _{^{102) 2, -CON (R 102}} ) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102, -OCON (R 102) 2, a halogen atom _{, -SO 3 M, -CO 2 M} , a heterocyclic group which may have a hydrocarbon group, and substituents of 1 to 40 carbon atoms which may have a substituent, R ¹ ~R ^5, R ¹² and R ¹³ represented by -CO- ^{R 102, -COO-R 101,} -OCO-R 102, -OR 102, -COCO-R 102, -SO 2 -R 101, -SO 2 N (R 102) 2, -CON (R 102) 2, _{^{-N (R 102) 2, -NHCO}} -R 102, -NHCO-N (R 102) 2, -NHCOOR 102, -OCON (R 102) 2, a halogen _{atom, -SO 3 M, -CO 2 M} , substituents A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent and a heterocyclic group which may have a substituent.

Preferred examples of R ⁶ and R ⁷ include the same ones as those preferred for R ¹ to R ⁵ , R ¹² and R ¹³ .

In the compound (I-b) or the compound (I-c), R ¹¹ represents a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, A pyridinyl group, a thienyl group which may have a substituent, a furyl group which may have a substituent, or an alkyl group having 1 to 40 carbon atoms which may have a substituent.

When R ¹¹ is an alkyl group which may have a substituent, the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 8 carbon atoms.

The phenyl group, the naphthyl group, the tetrahydronaphthyl group, the pyridinyl group, the thienyl group, the furyl group and the alkyl group may have a substituent. These groups may have an alkyl group instead of a substituent.

The substituent may be the same as the substituent which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

Preferable examples of the substituent include the same ones as those preferred among the substituents which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

The naphthyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, the furyl group and the alkyl group which may be bonded to the pyridinyl group, or the phenyl group, the naphthyl group, the tetrahydronaphthyl group, the thienyl group, The substituent of the furyl group and the pyridinyl group is preferably a group having 1 to 10 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl, An alkyl group; A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; A trifluoromethyl group; An oxycarbonyl group bonded with a hydrocarbon group of 1 to 10 carbon atoms; A nitro group; A hydroxy group; Sulfamoyl group; -SO ₃ M; -CO2M. ≪ / _RTI >

Examples of the substituent of the alkyl group include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; A hydroxy group; -SO ₃ M; -CO2M. ≪ / _RTI >

R ¹ is preferably a hydrogen atom.

L ¹ is preferably -CO-.

It is preferable that R ² to R ⁵ independently represent a hydrogen atom, a halogen atom or a nitro group. The halogen atom is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a chlorine atom. The number of halogen atoms is preferably 1 to 4, more preferably 1 or 2. R ³ or R ⁴ is preferably a halogen atom. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1. R ³ or R ⁴ is preferably a nitro group.

R ⁶ and R ⁷ independently of one another are preferably the same ones as those of R ¹ to R ⁵ , R ¹² and R ¹³ , and independently of each other, a methyl group, an ethyl group, a propyl group, an isopropyl group, more preferably a hydrocarbon group having 1 to 10 carbon atoms such as a tert-butyl group, a pentyl group, a hexyl group, a (2-ethyl) hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclohexyl group, .

Specific examples of the compound (I) include compounds (1 to 360 and 725 to 745) having substituents shown in Tables 1 to 4 and 9 (a) in the formula (I- .

B ¹ B ² represents a partial structure of any of the formulas (BB1) to (BB60).

B ¹ B ² is preferably a formula (BB1), a formula (BB6) or a formula (BB19).

R ¹¹ and R ¹⁴ represent partial structures of any of the formulas (HH1) to (HH89).

[Table 1]

[Table 2]

[Table 3]

[Table 4]

Specific examples of the compound (I) include compounds having a substituent shown in Tables 5 to 8 and 9 (b) (compounds 361 to 724 and 746 to 746) in the formula (I- 759).

B ¹ B ² represents a partial structure of any of the formulas (BB1) to (BB60), and preferably represents a formula (BB1), a formula (BB6) or a formula (BB19).

QQ represents a partial structure of any of the formulas (QQ1) to (QQ25), and preferably represents the formula (QQ25).

R ¹¹ represents a partial structure of any of the formulas (HH1) to (HH89).

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9 (a)]

[Table 9 (b)]

Other specific examples of the compound (I) include a compound of the formula (I-aa) having a substituent shown in Table 10 and a compound of the formula (I-bb) having a substituent shown in Table 11.

In Table 10 and Table 11, B ¹ B ² represents the structure of any one of the formulas (BB1) to (BB60), (BBD1), (BBI1), (BBJ2) . R ¹¹ and R ¹⁴ are groups represented by the following formulas (HH1) to (HH89), (HHJ5), HHJ6, HHJ7, HHJ10, HHJ14, ), The formula (HHk6), and the formula (HHk7).

QQ represents a partial structure of any of the expressions (QQ1) to (QQ25).

[Table 10]

[Table 11]

Each symbol in Tables 1 to 9 (b) and Tables 10 to 11 represents the following partial structure.

In the partial structure, Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group. In addition, *, B ¹ , B ^2, and ** denote the combined hands, respectively.

In each of the partial structures, although only substituent groups that are substituted in a cyclic structure are bonded at any of ortho, para, and meta positions, examples in the following examples include substitution at ortho, para, and meta positions Are included.

Compounds 1 to 12, Compounds 100 to 360, Compounds 448 to 759, Compounds 01-10, Compounds 01-124, Compounds 01-138, Compounds 01-151, Compounds 01-24, Compounds 01-364, -37, compounds 01-378, compounds 01-391, 21-107, 21-108, 21-117, 21-118, 21-119, 21-13, -14, 21-144, 21-15, 21-167, 21-168, 21-169, 21-185, 21-219, 21-293, 21-293, -294, 21-30, 21-31, 21-32, 21-34, 21-37, 21-38, 21-39, 21-4, 21-40 and 21 -43, 21-46, 21-48, 21-5, 21-53, 21-87, 21-88, 21-89, 22-10, -1411, 22-1414, 22-1417, 22-1439, 22-1440, 22-340, Compounds 22-3566, 22-3569, 22-3569, 22-3570, 22-3570, 22-3569, 22-3569, 9, Compound 51-28, Compound 52-2436, Compound 31-107, Compound 31-31, Compound 31-32, Compound 31-34, Compound 31-37, Compound 31-38, Compound 31-39, Compound 31- 40, Compound 31-43, Compound 31-46, Compound 31-49, Compound 31-5, Compound 31-54, Compound 32-1411, Compound 32-1414, Compound 32-1417, Compound 41-842, Compound 41- 843, compound 41-845, compound 71-25, compound 71-30, and compound 72-12 are preferable,

Compounds 1 to 12, compounds 100 to 273, compounds 448 to 637, and compounds 725 to 759 are more preferable,

Compounds 1 to 12, compounds 100 to 168, compounds 186 to 255, compound 273, compounds 448 to 532, compounds 550 to 619, compound 637, compounds 725 to 726, compounds 732 to 733, To compound 740, compounds 746 to 747, and compounds 753 to 754 are more preferable,

The compounds 100 to 168, the compounds 186 to 255, the compound 273, the compounds 464 to 532, the compounds 550 to 619, the compound 637, the compounds 732 to 733, the compounds 739 to 740, the compounds 746 to 747, ~ Compound 754 is particularly preferred.

Specific examples of the compound (I) include compounds in which one to three -SO ₃ M or -CO ₂ M are bonded to the compounds represented by Tables 1 to 9 (a), Table 9 (b), and Tables 10 to 11 Compounds may also be mentioned. For example, the compound in which one to three sulfo groups are bonded to the compound 102 of Table 2 shows the following structure. In the formula, - (SO ₃ H) means that the hydrogen atom of any of the compounds 102 is substituted.

Compounds 1 to 12, Compounds 100 to 360, Compounds 448 to 759, Compounds 01-10, Compounds 01-124, Compounds 01-138, Compounds 01-151, Compounds 01-24, Compounds 01-364, -37, compounds 01-378, compounds 01-391, 21-107, 21-108, 21-117, 21-118, 21-119, 21-13, -14, 21-144, 21-15, 21-167, 21-168, 21-169, 21-185, 21-219, 21-293, 21-293, -294, 21-30, 21-31, 21-32, 21-34, 21-37, 21-38, 21-39, 21-4, 21-40 and 21 -43, 21-46, 21-48, 21-5, 21-53, 21-87, 21-88, 21-89, 22-10, -1411, 22-1414, 22-1417, 22-1439, 22-1440, 22-340, Compounds 22-3566, 22-3569, 22-3569, 22-3570, 22-3570, 22-3569, 22-3569, 9, Compound 51-28, Compound 52-2436, Compound 31-107, Compound 31-31, Compound 31-32, Compound 31-34, Compound 31-37, Compound 31-38, Compound 31-39, Compound 31- 40, Compound 31-43, Compound 31-46, Compound 31-49, Compound 31-5, Compound 31-54, Compound 32-1411, Compound 32-1414, Compound 32-1417, Compound 41-842, Compound 41- 843, compound 41-845, compound 71-25, compound 71-30, and compound 72-12 are bonded to one to three -SO ₃ M or -CO ₂ M,

Compounds 1 to 12, compounds 100 to 273, compounds 448 to 637, and compounds 725 to 759 are more preferable,

Compounds 1 to 12, compounds 100 to 168, compounds 186 to 255, compound 273, compounds 448 to 532, compounds 550 to 619, compound 637, compounds 725 to 726, compounds 732 to 733, To compounds 740, 746 to 747, and 753 to 754 are more preferably bonded with one to three -SO ₃ M or -CO ₂ M,

The compounds 100 to 168, the compounds 186 to 255, the compound 273, the compounds 464 to 532, the compounds 550 to 619, the compound 637, the compounds 732 to 733, the compounds 739 to 740, the compounds 746 to 747, ~ the compound 754, the coupling 1 to 3 -SO ₃ M or -CO ₂ M compound is particularly preferred.

As the compound (I), in the formula (I), L ¹ is -CO- or -SO ₂ -, preferably -CO-, R ¹ is a hydrogen atom or -SO ₃ M and R ² to R ⁵ -SO ₃ M, or a halogen atom, and R ¹¹ is -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -SO ₃ M, -CO ₂ M, -OR ¹⁰² , -SO ₂ N (R ¹⁰² ) ₂ , an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent selected from the group consisting of a halogen atom, a cyano group and a nitro group, one of R ¹² and R ¹³ is a cyano group, R ¹² and R ¹³ is -CO-R ¹¹ or -SO ₂ -R ¹¹ , preferably -CO-R ¹¹ , and R ¹⁰¹ and R ¹⁰² are each a hydrogen atom or an aliphatic hydrocarbon having 1 to 8 carbon atoms Group, and M is a hydrogen atom or an alkali metal atom,

L ¹ is -CO- or -SO ₂ -, preferably -CO-, R ¹ is a hydrogen atom or -SO ₃ M and R ² to R ⁵ are each independently a hydrogen atom, a nitro group, -SO ₃ M, or a halogen atom, and R ¹¹ is -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -SO ₃ M, -CO ₂ M, -OR ¹⁰² , -SO ₂ N (R ¹⁰² ) ₂ , R ¹² and R ¹³ is a cyano group, and the other of R ¹² and R ¹³ is -CO-R ¹¹ or -SO ₂ -R ¹¹ , Preferably -CO-R ¹¹ , R ¹⁰¹ and R ¹⁰² are each a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and M is a hydrogen atom or an alkali metal atom.

(I-c), L ¹ is -CO- or -SO ₂ -, preferably -CO-, and R ¹ is hydrogen -SO ₃ M, and R ² to R ⁵ are each independently a hydrogen atom, a nitro group, -SO ₃ M, or a halogen atom, and R ⁶ to R ⁷ are each independently a hydrogen atom, -SO ₃ M, alkyl group having 1 to 4 carbon atoms, a cycloalkyl group or a phenyl group having a carbon number of 3~8, R ¹¹ is ^{-COO-R 101, -OCO-R} 102, -SO 3 M, -CO 2 M, -OR 102, -SO 2 N (R ¹⁰² ) ₂ , an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent selected from the group consisting of a halogen atom, a cyano group and a nitro group, and R ¹⁰¹ and R ¹⁰² each represent a hydrogen atom, And M is a hydrogen atom or an alkali metal atom.

Compound (Ⅰ) is, R ¹ is (in the case that referred to as phthalonitrile compound), the compound represented by the time a hydrogen atom, formula (pt1) to the compound represented by the formula (pt2) (hereinafter alkoxide compound , And then reacting the compound represented by formula (pt3) and the compound represented by formula (pt4) in the presence of an acid. When R < ¹ > is other than a hydrogen atom, the compound (I) can be further produced by reacting with a compound represented by the formula (pt5).

[In the formulas (pt1) to (pt5) and (l), L ¹ , R ¹ to R ⁵ and R ¹¹ to R ¹³ have the same meanings as defined above.

R ⁷⁷⁷ represents an alkyl group having 1 to 20 carbon atoms.

M ¹ represents an alkali metal atom.

LG represents a halogen atom, a methanesulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group.

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ⁷⁷⁷ include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert- An alkyl group having 1 to 6 carbon atoms.

Examples of the alkali metal atom represented by M ¹ include a lithium atom, a sodium atom and a potassium atom.

The amount of the alkoxide compound to be used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles per 1 mole of the phthalonitrile compound It is mall.

The amount of the compound (pt3) to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and even more preferably 1 to 3 moles per 1 mole of the phthalonitrile compound. 2 moles.

The amount of the compound (pt4) to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 3 moles per 1 mole of the phthalonitrile compound. 2 moles.

Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; Sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; And carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, and preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p- And more preferably acetic acid.

The amount of acid to be used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles per 1 mole of the phthalonitrile compound .

The reaction of the phthalonitrile compound, the alkoxide compound, the compound (pt3) and the compound (pt4) is usually carried out in the presence of a solvent.

As the solvent, water; Nitrile solvents such as acetonitrile; Alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; Ether solvents such as tetrahydrofuran; Ketone solvents such as acetone; Ester solvents such as ethyl acetate; Aliphatic hydrocarbon solvents such as hexane; Aromatic hydrocarbon solvents such as toluene; Halogenated hydrocarbon solvents such as methylene chloride and chloroform; Amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; An ether solvent, a ketone solvent, an ester solvent, an aromatic hydrocarbon solvent, a halogenated hydrocarbon solvent, an amide solvent, and a sulfoxide solvent can be given as examples of the solvent used in the present invention, and examples thereof include water, nitrile solvents, alcohol solvents, More preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N , N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide, and more preferably water, acetonitrile, methanol, ethanol, 2-propanol, N, N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide. Particularly preferable examples include water, acetonitrile, methanol, ethanol and 2-propanol.

The amount of the solvent to be used is usually 1 to 1000 parts by mass based on 1 part by mass of the phthalonitrile compound.

The reaction temperature is usually 0 to 200 캜, preferably 0 to 100 캜, more preferably 0 to 70 캜, and still more preferably 0 to 50 캜. The reaction time is usually from 0.5 to 300 hours.

The amount of the compound (pt5) to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, per 1 mole of the compound (I) in which R ¹ is a hydrogen atom, More preferably 1 to 2 mols.

When the compound (pt5) is reacted, it is preferable that a base coexists. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, pyridine and piperidine, organic bases such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert- Organometallic compounds such as metal alkoxide, butyllithium, tert-butyllithium and phenyllithium; And inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.

The amount of the base to be used is usually from 1 to 10 moles, preferably from 1 to 5 moles, more preferably from 1 to 3 moles, and most preferably from 1 to 3 moles per mole of the compound (I) wherein R ¹ is a hydrogen atom Is 1 to 2 moles.

The reaction of the compound (pt5) is usually carried out in the presence of a solvent. The solvent may be selected from the same range as described above.

The amount of the solvent to be used is usually 1 to 1000 parts by mass based on 1 part by mass of the compound (I) in which R ¹ is not a hydrogen atom. The reaction temperature of the compound (pt5) is usually -90 to 200 占 폚, preferably -80 to 100 占 폚, and more preferably 0 to 50 占 폚. The reaction time is usually from 0.5 to 300 hours.

When the compound (I) does not have a sulfo group or -SO ₃ M ² , the compound (I) is reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to form a sulfo group or -SO ₃ M ² Can be introduced.

M ² represents an alkali metal atom.

Examples of the alkali metal atom represented by M ² include a lithium atom, a sodium atom and a potassium atom.

The amount of SO ₃ to be used in fuming sulfuric acid is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, and still more preferably 5 moles per 1 mole of compound (I) ~ 25 moles.

The amount of sulfuric acid to be used in the fuming sulfuric acid is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 100 moles, relative to 1 mole of the compound (I) 50 moles.

The amount of the chlorosulfonic acid to be used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, relative to 1 mole of the compound (I) to be.

The reaction temperature for the sulphation is usually -20 to 200 占 폚, preferably -10 to 100 占 폚, and more preferably 0 to 50 占 폚. The reaction time is usually from 0.5 to 300 hours.

The method of extracting the compound (I) from the reaction mixture is not particularly limited, and can be taken out by various known methods. For example, after completion of the reaction, the reaction mixture is filtered to obtain the compound (I). After filtration, the obtained residue may be subjected to column chromatography or recrystallization. After completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.

≪ Quinophthalone compound &

Examples of the quinophthalone compound contained in the pigment composition of the present invention include compounds represented by formulas (K-1) to (K-17).

[R ^k1 to R ^k266 independently represent a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , -SO ₂ N (R _{^{102) 2, -CON (R 102}} ) 2, -N (R 102) 2, -NHCO-R 102, -NHSO 2 -R 102, a halogen atom, a cyano group, a nitro group, -SO ₃ H, -CO _{2 H, -SO 2 Cl, -SO-} R 102; A monovalent to trivalent metal salt of -SO ₃ H or -CO ₂ H; An alkylammonium salt of -SO ₃ H or -CO ₂ H; A phthalimido methyl group which may have a substituent, a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

The adjacent groups of R ^k1 to R ^k266 may be united to form a ring which may have a substituent.

R ¹⁰¹ represents, independently of each other, a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ¹⁰² represents a hydrogen atom, a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

When a plurality of R ¹⁰¹ and R ¹⁰² exist, they may be the same or different.]

R ^k1 ~R represented by the ^{k266 -CO-R 102, -COO-} R 101, -OCO-R 102, -OR 102, -SO 2 -R 101, -SO 2 N (R 102) 2, -CON ( _{^{R 102) 2, -N (R}} 102) 2, -NHCO-R 102, the halogen ^{atom, R 1 ~R 5, R 12} , R 13 -CO-R 102, -COO-R represented by ^101, - ^{OCO-R 102, -OR 102,} -SO 2 -R 101, -SO 2 N (R 102) 2, -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, halogen atoms And these groups may further have a substituent. Examples of the substituent include an N, N-dimethylamino group, an N, N-diethylamino group, an amino group, a 4-methyl-1-piperazinyl group, a 4 -Ethyl-1-piperazinyl group, 1-piperazinyl group, 1-piperidinylmethyloxy group, 4-morpholinyl group and the like.

^Examples of -NHSO ₂ -R ¹⁰² represented by R ^k1 to R k265 include a sulfonylamino group; (2-ethyl) hexylsulfonylamino group, heptylsulfonylamino group, octylsulfonylamino group, heptylsulfonylamino group, heptylsulfonylamino group, heptylsulfonylamino group, heptylsulfonylamino group, Sulfonyl groups in which a hydrocarbon group having 1 to 20 carbon atoms such as a nonylsulfonylamino group, a decylsulfonylamino group, an undecylsulfonylamino group, a dodecylsulfonylamino group, an icosylsulfonylamino group, a phenylsulfonylamino group and a p- An amino group, an amino group, a 4-methyl-1-piperazinyl group, a 4-methyl-1-piperazinyl group, a 4-methyl- -Ethyl-1-piperazinyl group, 1-piperazinyl group, 1-piperidinylmethyloxy group, 4-morpholinyl group and the like.

^Examples of -SO-R ¹⁰² represented by R ^k1 to R ^k265 include methylsulfinyl, ethylsulfinyl, ^{propylsulfinyl} , ^{butylsulfinyl} , ^{pentylsulfinyl} , ^{hexylsulfinyl} , A sulfinyl group having a hydrocarbon group having 1 to 20 carbon atoms such as an octylsulfinyl group, an octylsulfinyl group, an octylsulfinyl group, an octylsulfinyl group, a nonylsulfinyl group, a decylsulfinyl group, an undecylsulfinyl group, a dodecylsulfinyl group, an icosylsulfinyl group, These groups may further have a substituent. Examples of the substituent include an N, N-dimethylamino group, an N, N-diethylamino group, an amino group, a 4-methyl- 1- piperazinyl group, Piperazinyl group, 1-piperazinyl group, 1-piperidinylmethyloxy group, 4-morpholinyl group and the like.

R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² , which may be the same or different, each represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent represented by R ^k1 to R ^k266 or a heterocyclic group which may have a substituent , A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

^Examples of the monovalent to trivalent metal salt of -SO ₃ H or -CO ₂ H group represented by R ^k1 to R ^k266 include alkali metal salts such as sodium salts and potassium salts; Alkaline earth metal salts such as magnesium salts and calcium salts; Iron salts; Aluminum salts; And the like,

Examples of the alkylammonium salt of -SO ₃ H or -CO ₂ H include an ammonium salt derived from a monoalkylamine having 1 to 40 carbon atoms such as octylamine, laurylamine and stearylamine; Quaternary alkylammonium salts such as palmityltrimethylammonium, dilauryldimethylammonium, distearyldimethylammonium and the like.

When the valence of the metal ion forming the metal salt of -SO ₃ H or -CO ₂ H is more than 2, the ratio of the quinophthalone compound having -SO ₃ ^- or -CO ₂ ^- Are adjusted according to the singer to maintain electrical neutrality.

As the substituent in the phthalimido methyl group (C ₆ H ₄ (CO) ₂ N-CH ₂ -) which may have a substituent,

A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;

Examples of the straight chain or branched chain alkyl group such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, neopentyl group, n- Or branched alkyl group having 1 to 20 carbon atoms; Part or all of hydrogen atoms such as a trichloromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2,2-dibromoethyl group, and a 2,2,3,3-tetrafluoropropyl group An alkyl group having 1 to 20 carbon atoms substituted with a halogen atom; An alkyl group having 1 to 20 carbon atoms having a substituent such as a 2-ethoxyethyl group, a 2-butoxyethyl group or a 2-nitropropyl group;

A phenyl group, a naphthyl group, an anthranyl group, a p-tolyl group, a p-tert-butylphenyl group, a p-bromophenyl group, 2-naphthyl group, 4,5,8-trichloro-2-naphthyl group, anthraquinonyl group, 2-methylphenyl group, An aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent such as a 2-amino anthraquinonyl group;

An alkyl group having 1 to 20 carbon atoms such as a benzyl group, a 4-methylbenzyl group, a 4-tert-butylbenzyl group, a 4-methoxybenzyl group, a 4-nitrobenzyl group, An aromatic hydrocarbon group;

Propyloxy group, n-butoxy group, isobutyloxy group, tert-butyloxy group, neopentyloxy group, 2,3-dimethyl-3-pentyloxy group, n- Hexyloxy group, n-octyloxy group, stearyloxy group, 2-ethylhexyloxy group, trichloromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 3,3-tetrafluoropropyloxy group, 2,2-ditrifluoromethylpropoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2-nitropropoxy group, An oxy group in which a hydrocarbon group having 1 to 20 carbon atoms is bonded on one side;

And the like.

The adjacent groups among the groups represented by R ^k1 to R ^{k266 may} be ^{monosubstituted} to form a ring which may have a substituent. As the ring, a saturated aliphatic hydrocarbon ring, an unsaturated hydrocarbon ring, an aromatic hydrocarbon ring and an aromatic heterocycle can be exemplified, and an aromatic hydrocarbon ring and an aromatic heterocycle are preferable. Examples of the aromatic hydrocarbon ring include benzene ring, naphthalene ring, anthracene ring and phenanthrene ring. Examples of the aromatic heterocycle include pyridine ring, pyrazine ring, pyrrole ring, quinoline ring, quinoxaline ring, furan ring, , Thiophene ring, benzothiophene ring, oxazole ring, thiazole ring, imidazole ring, pyrazole ring, indole ring, carbazole ring and the like. Examples of the substituent which the ring may have include the same substituent that the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have. Preferable examples of the substituents include the same ones as those preferred among the substituents which the hydrocarbon group represented by R ¹ to R ⁵ , R ¹¹ , R ¹² , R ¹³ , R ¹⁰¹ and R ¹⁰² may have.

Preferred ^examples of the groups represented by R ^k1 to R ^k266 include a halogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, -OR ¹⁰² , -SO ₃ H, -CO ₂ H, -SO ₃ H, CO ₂ H, an alkylammonium salt of -SO ₃ H or -CO ₂ H, a phthalimido methyl group which may have a substituent, and -SO ₂ N (R ¹⁰² ) ₂ , Examples of the group include a halogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and -OR ¹⁰² , and more preferred examples thereof include a halogen atom.

Examples of the quinophthalone compound contained in the pigment composition of the present invention include quinophthalone dyes and quinophthalone pigments,

Color index (published by The Society of Dyers and Colourists) and dyeing notes (Shisensha). A known quinophthalone yellow dye such as Acid Yellow 3,

Color Index (published by The Society of Dyers and Colourists). Pigment Yellow 138, and the like, a quinophthalone yellow pigment,

(K-1-1) to K-1-2, K-2-1 to K-2-68, K-3-1 to K- (K-4-1) to K-4-6, K-5-1 to K-5-6, K-6-1 to K- (K-7-1) to K-7-4, K-8-1 to K-8-2, K- 1 to K-9-2, K-10-1 to K-10-6, K-11-1 to K-11-2, K-12-1 to K-12-2, K-13-1 to K-13-2, K-14-1 to K- ), K-15-1 to K-15-2, K-16-1 to K-16-2 or K-17-1 to K -17-2), and the like,

C.I. Pigment Yellow 138, Formula (K-1-1) to Formula (K-1-2), Formula (K-2-1) to Formula (K- 2-68) K-3-23, K-4-1, K-6-1 to K-6-50, K-7-1 to K- (K-10-1), the compound represented by the formula (K-12-1) or the compound represented by the formula (K-14-1) Pigment Yellow 138 is more preferable.

These quinophthalone compounds may be used alone or in combination of two or more.

The pigment composition of the present invention may contain a colorant other than the compound (I) and the quinophthalone compound (hereinafter sometimes referred to as a colorant (A1-1)).

≪ Colorant (A1-1) >

The colorant (A1-1) may be a dye or a pigment.

As the dyes, known dyes can be used, and dyes described in the color index (published by The Society of Dyers and Colourists) and dyeing notes (Shika Sensha) can be mentioned. According to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes and phthalocyanine dyes can be mentioned. These dyes may be used alone or in combination of two or more.

Specifically, dyes having the following color index (CI) numbers can be mentioned.

C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

C.I. Acid Yellow 1, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 169, 172, 177, 178, 179, 184, 190, 144, 150, 155, 157, 160, 161, 163, 168, 169, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

C.I. Reactive Yellow 2, 76, 116;

C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 108, 109, 129, 132, 136, 138, 141;

C.I. Disperse Yellow 51, 54, 76;

C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;

C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

C.I. Reactive Orange 16;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 181, 207, 218, 222, 227, 230, 245, 247;

C.I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;

C.I. Acid Violet 34, 102;

C.I. Disperse Violet 26, 27;

C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

C.I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 112, 122, 128, 132, 136, 139;

C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112;

C.I. Direct Blue 40;

C.I. Disperse Blue 1, 14, 56, 60;

C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33;

C.I. Acid Green 3, 5, 9, 25, 27, 28, 41;

C.I. Basic Green 1;

C.I. Bat Green 1st.

As the pigment, a known pigment can be used, and for example, a pigment classified as pigment in the color index (The Society of Dyers and Colourists) can be mentioned. These may be used alone or in combination of two or more.

Specifically, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 139 , 147, 148, 150, 153, 154, 166, 173, 185, 194 and 214;

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

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266 , 268, 269, 273 and the like;

C.I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;

C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;

C.I. Pigment Green 7, 36, 58, 59 and the like.

Examples of the other colorants (A1-1) include yellow dyes and yellow pigments (hereinafter collectively referred to as "yellow coloring agents"), green dyes and green pigments (hereinafter collectively referred to as "green coloring agents" ), Yellow pigments and green pigments are more preferable, and green pigments are more preferable.

Examples of the yellow dye include dyes in which the hue is classified into yellow, and yellow pigments include pigments in which the hue is classified into yellow.

Among the yellow pigments, metal-containing yellow pigments and isoindoline yellow pigments are preferable, and C.I. Pigment Yellow 129, 139, 150 and 185 are more preferable, and C.I. Pigment Yellow 139, 150, 185 are more preferable.

Examples of the green dye include dyes in which the hue is classified as green, and the green pigment is a pigment in which the hue is classified as green.

Among the green pigments, phthalocyanine pigments are preferable, and at least one kind selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable, and C.I. At least one kind selected from the group consisting of pigment greens 7, 36, 58 and 59 is more preferable.

The content of the compound (I) is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 99.999% by mass or less in the total amount of the pigment composition Is 99.997 mass% or less, and more preferably 99.995 mass% or less.

The content of the quinophthalone compound is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 70% by mass or less based on the total amount of the pigment composition Is not more than 60 mass%, more preferably not more than 50 mass%.

The content of the quinophthalone compound is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, further preferably 0.5 parts by mass or more, and 90 parts by mass or less based on 100 parts by mass of the compound (I) More preferably 70 parts by mass or less, and even more preferably 50 parts by mass or less.

When the other colorant (A1-1) is contained, the content of the other colorant (A1-1) is preferably 10 parts by mass or more based on 100 parts by mass of the total amount of the compound (I) and the quinophthalone compound, Is preferably 50 parts by mass or more, more preferably 100 parts by mass or more, and is preferably 10000 parts by mass or less, and more preferably 5000 parts by mass or less.

The total content of the compound (I) and the quinophthalone compound is preferably at least 0.5 part by mass, more preferably at least 1 part by mass, more preferably at least 2 parts by mass, particularly preferably at least 0.5 part by mass, Is not less than 3 parts by mass.

≪ Isoindoline compounds other than the compound (I) >

Examples of the isoindoline compounds other than the compound (I) contained in the pigment composition of the present invention include isoindoline dyes and isoindoline pigments.

Specific examples thereof include known isoindoline yellow dyes described in Color Index (published by The Society of Dyers and Colourists) and dyeing notes (Shikisensha), and color indexes (published by The Society of Dyers and Colourists) A known isoindoline yellow pigment is preferred, and CI Yellow pigments such as Pigment Yellow 139 and 185 are more preferable, and C.I. Pigment Yellow 185 is more preferable.

The isoindoline compounds other than these compounds (I) may be used alone or in combination of two or more.

The pigment composition of the present invention may contain a colorant other than an isoindoline compound other than the compound (I) and the compound (I) (hereinafter sometimes referred to as a colorant (A1-2)).

≪ Colorant (A1-2) >

The colorant (A1-2) may be a dye or a pigment.

As the dyes, known dyes can be used, and dyes described in the color index (published by The Society of Dyers and Colourists) and dyeing notes (Shika Sensha) can be mentioned. According to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes and phthalocyanine dyes can be mentioned. These dyes may be used alone or in combination of two or more.

Specifically, dyes having the following color index (CI) numbers can be mentioned.

C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 112, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

C.I. Reactive Yellow 2, 76, 116;

C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 108, 109, 129, 132, 136, 138, 141;

C.I. Disperse Yellow 51, 54, 76;

C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99; C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

C.I. Reactive Orange 16;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 181, 207, 218, 222, 227, 230, 245, 247;

C.I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;

C.I. Acid Violet 34, 102;

C.I. Disperse Violet 26, 27;

C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

C.I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 112, 122, 128, 132, 136, 139;

C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112;

C.I. Direct Blue 40;

C.I. Disperse Blue 1, 14, 56, 60;

C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33;

C.I. Acid Green 3, 5, 9, 25, 27, 28, 41;

C.I. Basic Green 1;

C.I. Bat Green 1st.

As the pigment, a known pigment can be used, and for example, a pigment classified as pigment in the color index (The Society of Dyers and Colourists) can be mentioned. These may be used alone or in combination of two or more.

Specifically, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138 , 147, 148, 150, 153, 154, 166, 173, 194 and 214;

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

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266 , 268, 269, 273 and the like;

C.I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;

C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;

C.I. Pigment Green 7, 36, 58, 59 and the like.

Examples of the other colorants (A1-2) include yellow dyes and yellow pigments (hereinafter collectively referred to as "yellow coloring agents"), green dyes and green pigments (hereinafter collectively referred to as "green coloring agents" ), Yellow pigments and green pigments are more preferable, and green pigments are more preferable.

Examples of the yellow dye include dyes in which the hue is classified into yellow, and yellow pigments include pigments in which the hue is classified into yellow.

Among the yellow pigments, quinophthalone yellow pigments and metal-containing yellow pigments are preferable, and C.I. Pigment Yellow 129, 138, 150 is more preferable, and C.I. Pigment Yellow 138, 150 is more preferred.

Examples of the green dye include dyes in which the hue is classified as green, and the green pigment is a pigment in which the hue is classified as green.

Among the green pigments, phthalocyanine pigments are preferable, and at least one kind selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable, and C.I. At least one kind selected from the group consisting of pigment greens 7, 36, 58 and 59 is more preferable.

The content of the isoindoline compound other than the compound (I) is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 70% by mass or more based on the total amount of the pigment composition % Or less, preferably 60 mass% or less, and more preferably 50 mass% or less.

The content of the isoindoline compound other than the compound (I) is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and still more preferably 0.5 parts by mass or more, relative to 100 parts by mass of the compound (I) And 90 parts by mass or less, more preferably 70 parts by mass or less, and further preferably 50 parts by mass or less.

The content of the other colorant (A1-2) is 10 parts by mass or more based on 100 parts by mass of the total amount of the isoindoline compounds other than the compound (I) and the compound (I) More preferably not less than 50 parts by mass, more preferably not less than 100 parts by mass, and not more than 10,000 parts by mass, and more preferably not more than 5,000 parts by mass.

The total content of the isoindoline compounds other than the compound (I) and the compound (I) is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and still more preferably 2 parts by mass or more per 100 parts by mass of the pigment composition Mass part or more, particularly preferably 3 mass parts or more.

<Green colorant>

The green colorant contained in the pigment composition of the present invention may be green dye or green pigment.

As the green dye, there can be used a known green dye, and a green dye described in a color index (published by The Society of Dyers and Colourists) and a dyeing note (Shisensha).

These dyes may be used alone or in combination of two or more.

Specifically, green dyes having the following color index (CI) numbers can be mentioned.

C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33;

C.I. Acid Green 3, 5, 9, 25, 27, 28, 41;

C.I. Basic Green 1;

C.I. Bat Green 1st.

As the green pigment, a known pigment can be used. For example, a green pigment described in a color index (published by The Society of Dyers and Colourists) can be mentioned.

These may be used alone or in combination of two or more.

Specifically, C.I. Pigment Green 7, 36, 58, 59 and the like.

As the green colorant contained in the pigment composition of the present invention, a green pigment is preferable. Among the green pigments, phthalocyanine pigments are preferable, and at least one kind selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is preferable, and C.I. At least one kind selected from the group consisting of pigment greens 7, 36, 58 and 59 is more preferable.

These green colorants may be used alone or in combination of two or more.

The pigment composition of the present invention may contain a colorant other than the compound (I) and the green colorant (hereinafter sometimes referred to as a colorant (A1-3)).

&Lt; Colorant (A1-3) >

The colorant (A1-3) may be a dye or a pigment.

As the dyes, known dyes can be used, and dyes described in the color index (published by The Society of Dyers and Colourists) and dyeing notes (Shika Sensha) can be mentioned. According to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes and phthalocyanine dyes can be mentioned. These dyes may be used alone or in combination of two or more.

Specifically, dyes having the following color index (CI) numbers can be mentioned.

C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 112, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

C.I. Reactive Yellow 2, 76, 116;

C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 108, 109, 129, 132, 136, 138, 141;

C.I. Disperse Yellow 51, 54, 76;

C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;

C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

C.I. Reactive Orange 16;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 181, 207, 218, 222, 227, 230, 245, 247;

C.I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;

C.I. Acid Violet 34, 102;

C.I. Disperse Violet 26, 27;

C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

C.I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 112, 122, 128, 132, 136, 139;

C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112;

C.I. Direct Blue 40;

C.I. Disperse Blue 1, 14, 56, 60, and so on.

As the pigment, a known pigment can be used, and for example, a pigment classified as pigment in the color index (The Society of Dyers and Colourists) can be mentioned. These may be used alone or in combination of two or more.

Specifically, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138 , 139, 147, 148, 150, 153, 154, 166, 173, 185, 194 and 214;

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

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266 , 268, 269, 273 and the like;

C.I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;

C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38 and the like.

As the other colorants (A1-3), yellow dyes and yellow pigments (hereinafter collectively referred to as &quot; yellow coloring agents &quot;) are preferable, and yellow pigments are more preferable. Examples of the yellow dye include dyes in which the hue is classified into yellow, and yellow pigments include pigments in which the hue is classified into yellow.

Among the yellow pigments, quinophthalone yellow pigments, metal-containing yellow pigments and isoindoline yellow pigments are preferred, and C.I. Pigment Yellow 129, 138, 139, 150 and 185 are more preferable, and C.I. Pigment Yellow 138, 139, 150, 185 are more preferable.

The content of the green coloring agent is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 99.999% by mass or less in the total amount of the pigment composition, 99.997 mass% or less, and more preferably 99.995 mass% or less.

The content of the green colorant is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, further preferably 0.5 parts by mass or more and 10000 parts by mass or less with respect to 100 parts by mass of the compound (I) More preferably not more than 5000 parts by mass, and most preferably not more than 4000 parts by mass.

When the other colorant (A1-3) is contained, the content of the other colorant (A1-3) is preferably 100 parts by mass or less based on 100 parts by mass of the total amount of the compound (I) and the green colorant, Preferably 90 parts by mass or less, more preferably 70 parts by mass or less, particularly preferably 50 parts by mass or less, and preferably 0.001 parts by mass or more, and more preferably 0.003 parts by mass or more.

The total content of the compound (I) and the green colorant is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, and even more preferably 80 parts by mass or more, particularly preferably 100 parts by mass or more, 90 parts by mass or more.

The coloring composition of the present invention comprises a pigment composition comprising at least one member selected from the group consisting of a compound (I), a quinophthalone compound, an isoindoline compound other than the compound (I) and a green colorant, and a solvent (E ).

&Lt; Solvent (E) >

The solvent (E) is, for example, an ester solvent (a solvent containing -COO- in a molecule and not containing -O-), an ether solvent (containing -O- in the molecule and containing -COO- (Solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not including -COO-), alcohol solvent (in the molecule), ether ester solvent OH, and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, and dimethylsulfoxide.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, Butyl, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate and? -Butyrolactone.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1 , 4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole and methyl anisole .

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, Methoxypropionate, ethyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, Methyl propionate, ethyl propionate, ethyl propionate, ethyl propionate, ethyl propionate, ethyl propionate, ethyl propionate, ethyl propionate, ethyl propionate, ethyl propionate, ethyl propionate, propyleneglycol monomethyl ether acetate, Ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol mono There may be mentioned ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate and the like.

Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, Cyclohexanone, isophorone, and the like.

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

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.

These solvents may be used in combination of two or more.

The content of the solvent (E) is preferably 40 to 99% by mass, and more preferably 50 to 95% by mass, based on the total amount of the coloring composition.

In the coloring composition of the present invention, the pigment composition comprising at least one member selected from the group consisting of a compound (I) and an isoindoline compound other than the quinophthalone compound, the compound (I) and a green colorant is preferably used in a solvent E).

The pigment composition may be subjected to a surface treatment using a rosin treatment, a derivative with an acidic group or a basic group, a graft treatment on the surface of the pigment composition with a polymer compound or the like, an atomization treatment with a sulfuric acid atomization method or the like, A cleaning treatment with an organic solvent or water for removing the ionic impurities, a removal treatment with an ion exchange method of ionic impurities, or the like may be performed. The particle size of the pigment composition is preferably substantially uniform. The pigment composition may contain a dispersant and perform dispersion treatment so that the pigment composition is uniformly dispersed in the dispersion.

As the dispersing agent, a surfactant and the like can be mentioned, and a surfactant of a cationic, anionic, nonionic or amphoteric type may be used. Specific examples thereof include surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersing agent include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOREN (manufactured by Kyoeisha Chemical Co., Ltd.), SOLSPERSE (manufactured by Zeneca), EFKA (Registered trademark) (manufactured by BASF Corporation), AJISPER (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK Chemie), BYK (Manufactured by BYK Chemie) and the like.

When a dispersant is used, the amount of the dispersant (solid content) to be used is preferably 300 parts by mass or less, more preferably 5 parts by mass or more and 100 parts by mass or less, based on 100 parts by mass of the pigment composition. When the amount of the dispersing agent is in the above range, a colored composition in a more uniform dispersed state tends to be obtained.

The content of the pigment composition in the coloring composition is usually from 0.1 to 60 mass%, preferably from 0.5 to 50 mass%, and more preferably from 1 to 40 mass%, based on the total amount of the coloring composition.

The content of the pigment composition in the coloring composition is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less, and more preferably 2% 75% by mass or less.

The coloring composition of the present invention may contain a resin (hereinafter sometimes referred to as resin (B)). By including the resin (B), the coloring composition further improves dispersion stability.

&Lt; Resin (B) >

The resin (B) is preferably an alkali-soluble resin, and at least one kind of monomer (a) selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (hereinafter sometimes referred to as "(a)") And more preferably a polymer having a derived structural unit.

The resin (B) is preferably a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenic unsaturated bond (hereinafter sometimes referred to as "(b)") Is preferably a copolymer having a structural unit.

Examples of the other structural unit include a structural unit derived from a monomer (c) (which is different from the monomer (a) and the monomer (b), hereinafter sometimes referred to as "(c)") copolymerizable with the monomer (a) A structural unit having an ethylenic unsaturated bond, and the like.

(a) include, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid and o-, m-, p-vinylbenzoic acid;

Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid;

Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept- , 5-carboxymethylbicyclo [2.2.1] hept-2-ene and 5-carboxyethylbicyclo [2.2.1] hept-2-ene;

Carboxylic anhydrides such as the anhydrides of the unsaturated dicarboxylic acids except fumaric acid and mesaconic acid;

(Meth) acryloyloxyalkyl] unsaturated monocarboxylic acid mono [(meth) acryloyloxyethyl] mono [2- (meth) acryloyloxyethyl] phthalic acid mono [2- Esters;

and unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as? - (hydroxymethyl) acrylic acid.

Of these, acrylic acid, methacrylic acid and maleic anhydride are preferable from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an aqueous alkali solution.

(b) is a copolymer obtained by copolymerizing a polymerizable compound having an ethylenic unsaturated bond with a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one member selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) It says. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.

(b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter may be referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, (Hereinafter sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter occasionally referred to as "(b3)").

(b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)") and alicyclic unsaturated And a monomer (b1-2) having a structure in which a hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenic unsaturated bond is preferable. (meth) acrylate,? -methyl glycidyl (meth) acrylate,? -ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, Vinylbenzyl glycidyl ether,? -Methyl vinyl benzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5- (Glycidyloxymethyl) styrene, 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene, 2,3,5- Styrenes such as 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) styrene and 2,4,6-tris (glycidyloxymethyl) ) Styrene, and the like.

(b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000; Cyclohexylmethyl (meth) acrylate (for example, cyclomer (registered trademark) A400 manufactured by Daicel Chemical Industries, Ltd.), 3,4-epoxycyclohexylmethyl (meth) (Registered trademark) M100 manufactured by Daicel Chemical Industries, Ltd.), a compound represented by formula (BI) and a compound represented by formula (BII).

[Wherein R ^a and R ^b independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group, .

X ^a and X ^b independently represent a single bond, * -R ^c -, * -R ^c -O-, * -R ^c -S- or * -R ^c -NH-.

R ^c represents an alkanediyl group having 1 to 6 carbon atoms.

* Stands for a binding hand with O.]

Examples of the compound represented by the formula (BI) include compounds represented by any one of the formulas (BI-1) to (BI-15). Among them, the compounds of the formula (BI-1), the formula (BI-3), the formula (BI-5), the formula (BI-7), the formula (BI- Are preferred, and compounds represented by the formula (BI-1), the formula (BI-7), the formula (BI-9) and the formula (BI-15) are more preferable.

Examples of the compound represented by the formula (BII) include compounds represented by any one of the formulas (BII-1) to (BII-15), and among them, (BII-3), (BII-5), (BII-7), (BII-9) and (BII-11) to Include compounds represented by formulas (BII-1), (BII-7), (BII-9) and (BII-15).

The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of a compound represented by formula (BI) and a compound represented by formula (BII). When these compounds are used in combination, the content of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5: 95 to 95: 5, more preferably 10: 90:10, and more preferably from 20:80 to 80:20.

(meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert- (Meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, tricyclo [5.2.1.0 ^{2, 6]} decan-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6] decane-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6] decene-8-one ( (Meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-9-yl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, isobornyl (Meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, (Meth) acrylic acid esters such as allylate and allylate;

(Meth) acrylic acid esters having a hydroxy group such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;

Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate;

2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5-methoxybicyclo [2.2.1] (2'-hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] hept- Ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept- 2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept- 2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept- Cyclohexyl [2.2.1] hept-2-ene, 5,6-bis (Tertiary butoxycarbonyl) bicyclo [2.2.1] hept-2-ene and 5,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept- Cyclounsaturated compounds;

N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N- Dicarbonylimide derivatives such as N-succinimidyl-3-maleimidepropionate and N- (9-acridinyl) maleimide;

Vinyl group-containing aromatic compounds such as styrene,? -Methylstyrene, vinyltoluene and p-methoxystyrene; Vinyl group-containing nitriles such as (meth) acrylonitrile; Halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; Vinyl group-containing amides such as (meth) acrylamide; Esters such as vinyl acetate; Dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; And the like.

Of these, styrene, vinyltoluene, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decane-9 (Meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-9- N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and benzyl (meth) acrylate are preferred.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth) acryloyl group. The resin having such a structural unit is obtained by adding a monomer having an ethylenically unsaturated bond to a group capable of reacting with a group of (a) or (b) to a polymer having a structural unit derived from (a) or (b) .

Examples of such structural units include structural units obtained by adding glycidyl (meth) acrylate to a (meth) acrylic acid unit, structural units obtained by adding 2-hydroxyethyl (meth) acrylate to a maleic anhydride unit and glycidyl (Meth) acrylate units, and structural units obtained by adding (meth) acrylic acid to (meth) acrylate units. When these structural units have a hydroxyl group, the structural unit to which the carboxylic acid anhydride is further added may also be a structural unit having an ethylenically unsaturated bond.

The polymer having a structural unit derived from the structural unit (a) can be produced, for example, by polymerizing a monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, the solvent and the like are not particularly limited, and those conventionally used in the art can be used. Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutylonitrile, 2,2'-azobis (2,4-dimethylvaleronitrile) and the like) and organic peroxides such as benzoyl peroxide ), And the solvent may be any one that dissolves the respective monomers.

The obtained polymer may be a solution after the reaction as it is, or a concentrated or diluted solution may be used, or it may be taken out as a solid (powder) by re-precipitation or the like.

(For example, tris (dimethylaminomethyl) phenol, etc.) and a polymerization inhibitor (for example, hydroquinone) may be used, if necessary, in the presence of a catalyst for the reaction of the carboxylic acid or the carboxylic acid anhydride with the cyclic ether.

Examples of the carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) (Meth) acrylate / glycidyl (meth) acrylate / glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl 3,4-epoxy-tricyclo [5.2.1.0 ^2,6] decyl (meth) acrylate / (meth) acrylic acid / N- cyclohexyl maleimide copolymer, the resin composition comprising 3,4-tricyclo [5.2.1.0 ^2,6 Decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth) acrylate copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl meth) acrylate / (meth) acrylic acid / vinyl toluene copolymer, the resin composition comprising 3,4-tricyclo [5.2.1.0 ^2,6] decyl (meth) acrylate / (meth) acrylic acid / 2-ethyl Chamber (meth) acrylate copolymer, the resin composition comprising 3,4-tricyclo [5.2.1.0 ^2,6] decyl (meth) acrylate / tricyclo [5.2.1.0 ^2,6] decenyl (meth) acrylate / ( (Meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acryloyloxymethyloxetane / (meth) acrylic acid / styrene copolymer, benzyl Styrene / (meth) acrylic acid copolymers, resins disclosed in the respective publications of Japanese Patent Application Laid-Open Nos. 9-106071, 2004-29518 and 2004-361455, .

Among them, as the resin (B), a copolymer containing a structural unit derived from (a) and a structural unit derived from (b) is preferable.

The resin (B) may be used in combination of two or more. In this case, the resin (B) is preferably at least one selected from 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) coalescence; 3,4-epoxy-tricyclo [5.2.1.0 ^2,6] decyl (meth) acrylate / (meth) acrylic acid / N- cyclohexyl maleimide / 2-hydroxyethyl (meth) acrylate copolymer; 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / vinyltoluene copolymer; To include 3,4-epoxy-tricyclo [5.2.1.0 ^2,6] decyl (meth) acrylate / (meth) acrylic acid / 2-ethylhexyl (meth) one or more selected from acrylate copolymer.

The weight average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. The dispersion degree (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

The acid value (in terms of solid content) of the resin (B) is preferably 10 to 300 mgKOH / g, more preferably 20 to 250 mgKOH / g, more preferably 30 to 200 mgKOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide necessary for neutralizing 1 g of the resin (B), and can be determined by titration using, for example, an aqueous potassium hydroxide solution.

The content of the resin (B) in the coloring composition is preferably from 3 to 99% by mass, more preferably from 5 to 99% by mass, and still more preferably from 7 to 95% by mass, based on the total solid content.

The coloring composition of the present invention may contain a coloring agent (hereinafter sometimes referred to as a coloring agent (A2)). The colorant (A2) may contain one or two or more coloring agents. The colorant (A2) preferably contains Compound (I), a yellow colorant or a green colorant.

&Lt; Colorant (A2) >

The colorant (A2) may be a dye or a pigment. As the dyes, known dyes can be used, and dyes described in the color index (published by The Society of Dyers and Colourists) and dyeing notes (Shika Sensha) can be mentioned. According to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes and phthalocyanine dyes can be mentioned. These dyes may be used alone or in combination of two or more.

Specifically, dyes having the following color index (CI) numbers can be mentioned.

C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 112, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

C.I. Reactive Yellow 2, 76, 116;

C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 108, 109, 129, 132, 136, 138, 141;

C.I. Disperse Yellow 51, 54, 76;

C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;

C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

C.I. Reactive Orange 16;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 181, 207, 218, 222, 227, 230, 245, 247;

C.I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;

C.I. Acid Violet 34, 102;

C.I. Disperse Violet 26, 27;

C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

C.I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 112, 122, 128, 132, 136, 139;

C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112;

C.I. Direct Blue 40;

C.I. Disperse Blue 1, 14, 56, 60;

C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33;

C.I. Acid Green 3, 5, 9, 25, 27, 28, 41;

C.I. Basic Green 1;

C.I. Bat Green 1st.

As the pigment, a known pigment can be used, and for example, a pigment classified as pigment in the color index (The Society of Dyers and Colourists) can be mentioned. These may be used alone or in combination of two or more.

Specifically, C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138 , 139, 147, 148, 150, 153, 154, 166, 173, 185, 194 and 214;

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

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266 , 268, 269, 273 and the like;

C.I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60;

C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;

C.I. Pigment Green 7, 36, 58, 59 and the like.

Examples of the other colorant (A2) include compounds (I), yellow dyes and yellow pigments (hereinafter collectively referred to as "yellow coloring agents"), green dyes and green pigments (I), a yellow pigment and a green pigment are more preferable, and a compound (I) and a green pigment are more preferable.

Examples of the yellow dye include dyes in which the hue is classified into yellow, and yellow pigments include pigments in which the hue is classified into yellow.

Among the yellow pigments, quinophthalone yellow pigments, metal-containing yellow pigments and isoindoline yellow pigments are preferred, and C.I. Pigment Yellow 129, 138, 139, 150 and 185 are more preferable, and C.I. Pigment Yellow 138, 139, 150, 185 are more preferable.

Examples of the green dye include dyes in which the hue is classified as green, and the green pigment is a pigment in which the hue is classified as green.

Among the green pigments, phthalocyanine pigments are preferable, and at least one kind selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable, and C.I. At least one kind selected from the group consisting of pigment greens 7, 36, 58 and 59 is more preferable.

When the coloring composition of the present invention contains the coloring agent (A2), a liquid containing the coloring agent (A2) containing the coloring agent (A2) and the solvent (E) is prepared in advance, The composition may be prepared. When the colorant (A2) is not soluble in the solvent (E), the liquid containing the colorant (A2) can be prepared by dispersing and mixing the colorant (A2) in the solvent (E). The liquid containing the coloring agent (A2) may contain a part or all of the solvent (E) contained in the coloring composition.

The coloring composition of the present invention comprises a pigment composition comprising a compound represented by formula (I) and at least one member selected from the group consisting of a quinophthalone compound, an isoindoline compound other than the compound (I) , The solvent (E), the colorant (A2) and the colorant (A2) containing the solvent (E). As the production method, a pigment composition comprising a compound represented by the formula (I) and at least one member selected from the group consisting of a quinophthalone compound, an isoindoline compound other than the compound (I) or a green colorant, (A2) containing the coloring agent (A2) and the solvent (E) is mixed with the coloring composition obtained by mixing the coloring composition (E) with a binder such as a beads mill.

The colorant (A2) is preferably a colorant containing at least one compound selected from a compound represented by the formula (I), a green colorant, and a yellow colorant.

The colorant (A2) may be subjected to a surface treatment using a rosin treatment, a colorant derivative into which an acidic group or a basic group is introduced, a graft treatment with a polymer compound or the like on the surface of the colorant (A2), an atomization treatment with a sulfuric acid atomization method, A cleaning treatment with an organic solvent or water to remove impurities, a removal treatment with an ion exchange method of ionic impurities, or the like may be performed. The particle diameter of the colorant (A2) is preferably substantially uniform. The colorant (A2) can be made to be uniformly dispersed in the colorant (A2) -containing liquid by containing the dispersant and performing the dispersion treatment. Each of the colorants (A2) may be dispersed singly or plural kinds thereof may be mixed and dispersed.

As the dispersing agent, a surfactant and the like can be mentioned, and a surfactant of a cationic, anionic, nonionic or amphoteric type may be used. Specific examples thereof include surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersing agent include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOREN (manufactured by Kyoeisha Chemical Co., Ltd.), SOLSPERSE (manufactured by Zeneca), EFKA (Registered trademark) (manufactured by BASF Corporation), AJISPER (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK Chemie), BYK (Manufactured by BYK Chemie) and the like.

When a dispersing agent is used to prepare the liquid containing the colorant (A2), the amount of the dispersing agent (solid content) to be used is preferably 300 parts by mass or less, more preferably 5 parts by mass or less per 100 parts by mass of the colorant (A2) Not less than 100 parts by mass. When the amount of the dispersant is in the above range, there is a tendency that a liquid containing the colorant (A2) in a more uniform dispersion state tends to be obtained.

The content of the colorant (A2) in the liquid containing the colorant (A2) is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, and more preferably 1 to 50% by mass, 40% by mass.

The content of the colorant (A2) in the liquid containing the coloring agent (A2) is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less based on the total amount of the solid matter, Is not less than 2 mass% and not more than 75 mass%.

The coloring composition of the present invention comprises the resin (B) and after preparing a liquid containing the coloring agent (A2) containing the coloring agent (A2) and the solvent (E) in advance, The liquid containing the coloring agent (A2) may previously contain a part or all, preferably a part of the resin (B) contained in the coloring composition. By including the resin (B) in advance, the dispersion stability of the liquid containing the colorant (A2) can be further improved.

The content of the resin (B) in the liquid containing the colorant (A2) is, for example, 1 to 500 parts by mass, preferably 5 to 200 parts by mass, relative to 100 parts by mass of the colorant (A2) 10 to 100 parts by mass.

The content of the colorant (A) including the pigment composition and the colorant (A2) in the coloring composition is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% Or less, and more preferably 2 mass% or more and 75 mass% or less.

The content of the compound (I) is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 99.999% by mass or less based on the total amount of the colorant (A) It is preferably 99.997 mass% or less, and more preferably 99.995 mass% or less.

The content of the quinophthalone compound is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 70% by mass or less based on the total amount of the colorant (A) Preferably 60 mass% or less, and more preferably 50 mass% or less.

The content of the quinophthalone compound is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, further preferably 0.5 parts by mass or more, and 90 parts by mass or less based on 100 parts by mass of the compound (I) More preferably 70 parts by mass or less, and even more preferably 50 parts by mass or less.

When the other colorant (A2) is contained, the content of the other colorant (A2) is preferably 10 parts by mass or more, more preferably 50 parts by mass or more per 100 parts by mass of the total amount of the compound (I) and the quinophthalone compound More preferably not less than 100 parts by mass, and not more than 10,000 parts by mass, and more preferably not more than 5,000 parts by mass.

The total content of the compound (I) and the quinophthalone compound is preferably 0.5 part by mass or more, more preferably 1 part by mass or more, further preferably 2 parts by mass or more, and most preferably 2 parts by mass or more in 100 parts by mass of the colorant (A) Particularly preferably not less than 3 parts by mass.

The content of the isoindoline compound other than the compound (I) is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, Is 70 mass% or less, preferably 60 mass% or less, and more preferably 50 mass% or less.

The content of the isoindoline compound other than the compound (I) is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and still more preferably 0.5 parts by mass or more, relative to 100 parts by mass of the compound (I) And 90 parts by mass or less, more preferably 70 parts by mass or less, and further preferably 50 parts by mass or less.

When the other coloring agent (A2) is contained, the content of the other coloring agent (A2) is preferably 10 parts by mass or more based on 100 parts by mass of the total amount of the isoindoline compound other than the compound (I) and the compound (I) More preferably not less than 50 parts by mass, more preferably not less than 100 parts by mass, and not more than 10,000 parts by mass, and more preferably not more than 5,000 parts by mass.

The total content of the isoindoline compounds other than the compound (I) and the compound (I) is preferably 0.5 part by mass or more, more preferably 1 part by mass or more, and still more preferably 1 part by mass or more in 100 parts by mass of the colorant (A) Is at least 2 parts by mass, particularly preferably at least 3 parts by mass.

The content of the green colorant is usually 0.001% by mass or more, preferably 0.003% by mass or more, more preferably 0.005% by mass or more, and the upper limit is 99.999% by mass or less, based on the total amount of the colorant (A) Is 99.997 mass% or less, and more preferably 99.995 mass% or less.

The content of the green colorant is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, further preferably 0.5 parts by mass or more and 10000 parts by mass or less with respect to 100 parts by mass of the compound (I) More preferably not more than 5000 parts by mass, and most preferably not more than 4000 parts by mass.

When the other coloring agent (A2) is contained, the content of the other coloring agent (A2) is preferably 10,000 parts by mass or less, more preferably 5,000 parts by mass or less based on 100 parts by mass of the total amount of the compound (I) More preferably not more than 4000 parts by mass, and preferably not less than 0.001 parts by mass, and more preferably not less than 0.003 parts by mass.

The colored curable composition of the present invention comprises a pigment composition comprising at least one member selected from the group consisting of a compound (I), a quinophthalone compound, an isoindoline compound other than the compound (I) and a green colorant, a solvent E) and a polymerizable compound (C).

&Lt; Polymerizable compound (C) >

The polymerizable compound (C) is a compound capable of polymerizing with an active radical and / or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, ) Acrylic acid ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl Acrylate, N-vinylpyrrolidone, and the above-mentioned monomer (a), monomer (b) and monomer (c).

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) Acrylate, ethylene glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A and 3-methylpentanediol di (meth) acrylate.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) Acrylate, pentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritolone , Ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol hexa (metha) acrylate, propylene glycol modified pentaerythritol tetra (meth) acrylate, (Meth) acrylate, propylene glycol-modified dipentaerythritol hexa ( Acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate, and preferably dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa And erythritol hexa (meth) acrylate.

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

The content of the polymerizable compound (C) in the colored curable composition is preferably 1 to 65% by mass, more preferably 3 to 60% by mass, and more preferably 5 to 55% by mass based on the total solid content desirable.

The colored curable composition of the present invention may contain a polymerization initiator (D).

&Lt; Polymerization initiator (D) >

The polymerization initiator (D) is not particularly limited as far as it is a compound capable of generating an active radical or an acid by the action of light or heat and capable of initiating polymerization, and a known polymerization initiator can be used.

Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, imidazole compounds, triazine compounds and acylphosphine oxide compounds.

Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy- 2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine, N-acetoxy- , 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethan- 1-imine, N-acetoxy- - {2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3- yl] ethan- 1- Yl] -3-cyclopentylpropan-1-imine and N-benzoyloxy-1- [9-ethyl-6- ( 2-methylbenzoyl) -9H-carbazol-3-yl] -3-cyclopentylpropan-1-one-2-imine. As O-acyloxime compounds, commercially available products such as Irgacure OXE01, OXE02 (manufactured by BASF Corporation) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, O-acyloxime compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy- 1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine is more preferable.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan- -1-one and 2- (dimethylamino) -2 - [(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one. As alkylphenone compounds, commercially available products such as Irgacure 369, 907 and 379 (manufactured by BASF Co., Ltd.) may be used.

Methylphenyl) propane-1-one, 2-hydroxy-2-methyl-1- Oligomers of 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one,?,? -Diethoxyacetophenone and benzyldimethylketal .

Examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'- Dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole (see, for example, JP-A 6-75372 and JP-A 6-75373) Bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis Bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) biimidazole (for example, Japanese Patent Publication No. 48-38403, Japanese Patent Laid-Open No. 62-174204 (See, for example, JP-A 7-10913, etc.) in which the phenyl group at the 4,4 ', 5,5'-position is substituted by a carboalkoxy group, And the like.

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl ) -6- (4-methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- ] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] (Trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine and 2,4- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine, and the like.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and the like.

Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; Benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert- butylperoxycarbonyl) benzophenone and Benzophenone compounds such as 2,4,6-trimethylbenzophenone; Quinone compounds such as 9,10-phenanthrenequinone, 2-ethyl anthraquinone and camphorquinone; Butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate and titanocene compounds.

These are preferably used in combination with the polymerization initiator D1 (particularly amines) described below.

The polymerization initiator (D) is preferably a polymerization initiator comprising at least one member selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a nonimidazole compound, More preferred is a polymerization initiator comprising an O-acyloxime compound.

The content of the polymerization initiator (D) is preferably 0.001 to 40% by mass, and more preferably 0.01 to 30% by mass, based on the total amount of solid components in the colored curable composition.

The colored curable composition of the present invention may contain a polymerization initiator (D1).

&Lt; Polymerization initiator (D1) >

The polymerization initiator (D1) is a compound or a sensitizer used for promoting the polymerization of the polymerizable compound initiated by the polymerization initiator. When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiator (D1) include an amine compound, an alkoxyanthracene compound, a thioxanthone compound, and a carboxylic acid compound.

Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4-dimethylamino benzoic acid 2 (Ethylhexyl), N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'- Bis (ethylmethylamino) benzophenone, and the like, preferably 4,4'-bis (diethylamino) benzophenone. As the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10- Anthracene and 2-ethyl-9,10-dibutoxyanthracene.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro- Santon et al.

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, Phenylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid.

When these polymerization initiator (D1) is used, the content thereof is preferably 0.001 to 30% by mass, and more preferably 0.01 to 20% by mass, based on the total amount of solid components in the colored curable composition.

The coloring composition of the present invention may further contain a leveling agent (F) and an antioxidant.

&Lt; Leveling agent (F) >

Examples of the leveling agent (F) include a silicone surfactant, a fluorine surfactant, and a silicon surfactant having a fluorine atom. These may have a polymerizable group in the side chain.

Examples of the silicone surfactant include a surfactant having a siloxane bond in the molecule. Specifically, TORAY silicon DC3PA, copper (SH7PA), copper DC11PA, copper SH21PA, copper (SH28PA), copper (copper) SH29PA, copper SH30PA, copper SH8400 (trade name: manufactured by Toray Dow Corning), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (made by Momentive Performance Materials Japan Joint-Industrial Company).

Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in the molecule. Concretely, there may be mentioned Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Ltd.), Megapark (registered trademark) F142D, copper F171, copper F172, copper F173, copper F177, copper F183, copper F554, R30, RS-718-K (manufactured by DIC Corporation), FTOP (registered trademark) EF301, EF303, EF351 and EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.) Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Research Institute).

Examples of the silicon-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megapac (registered trademark) R08, Copolymer BL20, Copolymer F475, Copolymer F477 and Copolymer F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, the content thereof is usually 0.0005 mass% or more and 1 mass% or less, preferably 0.001 mass% or more and 0.5 mass% or less based on the total amount of the coloring composition, Is not less than 0.001 mass% and not more than 0.2 mass%, more preferably not less than 0.002 mass% nor more than 0.1 mass%, and particularly preferably not less than 0.005 mass% nor more than 0.1 mass%. When the content of the leveling agent (F) is in the above range, the flatness of the color filter can be improved.

<Antioxidant>

From the standpoint of improving the heat resistance and light resistance of the colorant, it is preferable to use the antioxidant alone or in combination of two or more thereof. The antioxidant is not particularly limited as long as it is an antioxidant generally used industrially, and phenol antioxidants, phosphorus antioxidants and sulfur antioxidants can be used.

Examples of the phenolic antioxidant include Irganox 1010 (pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], BASF (Irganox 1076: octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate manufactured by BASF Corporation), Irganox 1330 (Irganox 1330: 3,3 ', 3 ", 5,5', 5" -hexa-tert-butyl-a, -Cresol, manufactured by BASF), Irganox 3114 (1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) (1H, 3H, 5H) -tione, manufactured by BASF, Irganox 3790: 1,3,5-tris ((4-tert- Triazine-2,4,6 (1H, 3H, 5H) -thione, manufactured by BASF Corporation), Irganox 1035 (Irganox 1135, manufactured by BASF Corporation), Irganox 1135 (manufactured by BASF Corporation), benzenephosphate (1, 1-dimethylethyl) -4-hydroxy, C7-C9 branched alkyl ester, manufactured by BASF), Irganox 1520L (4,6-bis (Irganox 3125, manufactured by BASF), Irganox 565 (2,4-bis (n-octylthio) -) (Adekastab AO-80 (Adekastab®), which is commercially available from BASF Co., Ltd.), 6- (4-hydroxy-3 ', 5'-di- AO-80: 3,9-bis (2- (3- (tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy) -1,1- (Sumilizer GA-80, manufactured by Sumitomo Chemical Co., Ltd. (trade name, manufactured by Sumitomo Chemical Co., Ltd.)), Sumilizer BHT ), Sumilizer GS (manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (manufactured by Cytec), and vitamin E (manufactured by Eizoi K.K.).

Examples of the phosphorus antioxidant include Irgafos 168 (tris (2,4-di-tert-butylphenyl) phosphite, manufactured by BASF), Irgafos 12 Butyl] dibenzo [d, f] [1,3,2] dioxaphospepin-6-yl] oxy] ethyl] amine, BASF (Irgafos 38: bis (2,4-bis (1,1-dimethylethyl) -6-methylphenyl) ethyl ester phosphoric acid, manufactured by BASF), Adekastab 329K Adekastab PEP-8 (manufactured by ADEKA), Sandstab P-EPQ (manufactured by Clariant), Weston 618 (manufactured by ADEKA), Adekastab PEP36 (Manufactured by GE), Western 619G (manufactured by GE), Ultranox 626 (manufactured by GE) and Sumilizer GP: 6- [3- (3-tert-butyl- Butyl dibenz [d, f] [1.3. 2] dioxaphosphperin) (manufactured by Sumitomo Chemical Co., Ltd.) .

Examples of the sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl or distearyl, and tetrakis [methylene (3-dodecylthio) propionate] And? -Alkylmercaptopropionic acid ester compounds of polyols such as methane.

<Other ingredients>

The coloring composition of the present invention may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents and the like, if necessary.

Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropyl Methyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3- 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, (Aminoethyl) -3-aminopropylmethyldiethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, Aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, 3-aminopropyltri A silane, 3-aminopropyl triethoxysilane, N- phenyl-3-aminopropyltrimethoxysilane, N- phenyl-3-aminopropyl, and the like on the silane.

<Color filter>

A color filter can be formed from the coloring composition or colored curable composition of the present invention. Examples of the method for forming a colored pattern include a photolithographic method, an inkjet method, and a printing method. Among them, the photolithographic method is preferable. The photolithography method is a method in which the above-mentioned colored curable composition is applied to a substrate, followed by drying to form a colored curable composition layer, and then the colored curable composition layer is exposed and developed through a photomask. In the photolithographic method, it is preferable that the colored curable composition contains a polymerization initiator (D). In the photolithographic method, a colored coating film (coating film) which is a cured product of the colored curable composition layer can be formed by not using a photomask during exposure and / or not developing it. The coloring pattern or colored coating film thus formed can be used as the color filter of the present invention.

The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose or use. For example, it is 0.1 to 30 탆, preferably 0.1 to 20 탆, 6 mu m.

As the substrate, a glass plate, a resin plate, silicon, and an aluminum, silver, silver / copper / palladium alloy thin film, or the like are formed on the substrate. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.

The formation of each color pixel by the photolithographic method can be carried out by a known apparatus or condition. For example, it can be manufactured as follows.

First, a colored curable composition is applied on a substrate, and heated and dried (pre-baked) and / or reduced-pressure dried to remove volatile components such as a solvent and dried to obtain a smooth colored curable composition layer.

Examples of the application method include a spin coating method, a slit coating method, and a slit and spin coating method.

Next, the colored curable composition layer is exposed through a photomask for forming a desired colored pattern. It is preferable to use an exposure apparatus such as a mask aligner and a stepper to uniformly align the entire exposure surface with a parallel light beam or precisely align the substrate with the photomask and the substrate on which the colored curable composition layer is formed.

The coloring curable composition layer after exposure is brought into contact with a developing solution to develop a colored pattern on the substrate. By the development, the unexposed portion of the colored curable composition layer is dissolved and removed in the developer.

As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate and tetramethylammonium hydroxide is preferable.

The developing method may be any of paddle method, dipping method and spray method. Further, the substrate may be inclined at an arbitrary angle at the time of development.

The substrate after development is preferably washed with water.

Further, post-baking is preferably performed on the obtained coloring pattern.

The color filter is useful as a color filter used in a liquid crystal display device, particularly as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper and the like) and a solid-state image pickup device.

[Example]

Hereinafter, the present invention will be described in more detail with reference to Examples. However, the present invention is not limited by the following Examples in the first place, and the present invention is not limited to the following Examples. Of course, all of which are within the technical scope of the present invention. In the following description, "part" means "part by mass" and "%" means "% by mass" unless otherwise specified.

In the following synthetic examples, the structure of the compound was determined by NMR (JMM-ECA-500, manufactured by JEOL Ltd.) or mass spectrometry (LC: Agilent 1200 type, MASS; Respectively.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by the GPC method under the following conditions.

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

Column: TSK-GELG2000HXL

Column temperature: 40 ° C

Solvent: tetrahydrofuran

Flow rate: 1.0 mL / min

Solid content concentration of analytical sample: 0.001 to 0.01 mass%

Injection volume: 50 μL

Detector: RI

Standard materials for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500 and A-500 (manufactured by TOSOH CORPORATION)

The ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) in terms of polystyrene obtained as described above was dispersed.

Synthetic Example 1

11.0 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 91.5 parts of methanol were mixed. While maintaining the temperature of the obtained mixture at 2 占 폚, a mixture of 8.59 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 77.6 parts of methanol was added dropwise over 1 hour and 45 minutes, And stirred for 40 minutes. To the resulting mixture, 4.18 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added and the mixture was stirred at 2 占 폚 for 1 hour and 45 minutes. 17.0 parts of acetic acid was added while maintaining the temperature of the obtained mixture at 4 占 폚 or lower. 23.9 parts of pivaloylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the resulting mixture, followed by stirring at room temperature for 87 hours. 10.8 parts of pivaloylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 5.40 parts of acetic acid were added to the obtained mixture, followed by stirring at 40 占 폚 for 4 hours and 30 minutes. The resulting mixture was filtered, and the residue was washed with 360 parts of methanol. The obtained residue was dried under reduced pressure at 60 占 폚 to obtain 22.8 parts of a compound represented by the formula (I-1) (Compound 101).

<Identification (Identification) of Compound (Compound 101) Represented by Formula (I-1)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 362

                        Exact Mass: 361

Synthetic Example 2

2.59 parts of 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 24.1 parts of methanol were mixed. While maintaining the temperature of the obtained mixture at 2 占 폚, a mixture of 1.50 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 23.2 parts of methanol was added dropwise to the mixture over 1 hour and 10 minutes . The resulting mixture was stirred at 2 占 폚 for 2 hours and 20 minutes. 2.35 parts of acetic acid was added while maintaining the temperature of the obtained mixture at 3 占 폚 or lower, and 4.13 parts of pivaloylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was further added. The resulting mixture was stirred at room temperature for 3 hours and 35 minutes, and then stirred at 40 ° C for 1 hour and 45 minutes. To the obtained mixture, 4.16 parts of pivaloylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 40 占 폚 for 1.5 hours. The resulting mixture was stirred at room temperature for 37 hours. 1.89 parts of pivaloylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1.24 parts of acetic acid were added to the obtained mixture, followed by stirring at 40 占 폚 for 5 hours and 15 minutes. The resulting mixture was filtered, and the residue was washed with 198 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C to obtain 5.58 parts of a compound represented by the formula (I-2) (Compound 188).

<Identification of Compound (Compound 188) Represented by Formula (I-2)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 407

                         Exact Mass: 406

Synthetic Example 3

7.02 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 61.6 parts of methanol were mixed. While maintaining the temperature of the obtained mixture at 2 占 폚, a mixture of 8.20 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 74.6 parts of methanol was added dropwise over 1 hour and 30 minutes. The resulting mixture was stirred at 2 占 폚 for 6 hours and 15 minutes. 10.7 parts of acetic acid was added while maintaining the temperature of the resulting mixture at 4 占 폚 or lower. To the obtained mixture, 17.6 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at room temperature for 44 hours. The resulting mixture was filtered, and the residue was washed with 800 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C to obtain 18.0 parts of a compound (Compound 102) represented by the formula (I-3).

<Identification of Compound (Compound 102) Represented by Formula (I-3)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 402

                         Exact Mass: 401

Synthetic Example 4

4.12 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 37.2 parts of methanol were mixed. A mixture of 4.82 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 45.2 parts of methanol was added dropwise to this mixture over 1 hour while maintaining the temperature of the mixture at 2 占 폚. The resulting mixture was stirred at 2 캜 for 6 hours. 6.29 parts of acetic acid was added while maintaining the temperature of the obtained mixture at 4 占 폚 or lower. To the obtained mixture, 12.7 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added and the mixture was stirred at 2 占 폚 for 1 hour and then at room temperature for 20 minutes. The obtained mixture was stirred at 40 占 폚 for 2 hours and then at room temperature for 11 hours and further at 40 占 for 5 hours and 40 minutes. To the obtained mixture, 3.18 parts of acetic acid and 6.45 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added. The obtained mixture was stirred at 40 占 폚 for 4 hours and then at room temperature for 62 hours. The resulting mixture was filtered, and the residue was washed three times with methanol of the same volume as the residue. The obtained residue was recrystallized by N, N-dimethylformamide. The obtained crystals were dried under reduced pressure at 60 캜 to obtain 9.99 parts of a compound (Compound 112) represented by the formula (I-4).

<Identification of Compound (Compound 112) Represented by Formula (I-4)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 470

                         Exact Mass: 469

Synthetic Example 5

4.07 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 36.0 parts of methanol were mixed. While maintaining the temperature of the obtained mixture at 2 占 폚, a mixture of 4.76 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 44.3 parts of methanol was added dropwise over 1 hour and 10 minutes. The obtained mixture was stirred at 2 ° C for 5 hours and 25 minutes. 6.23 parts of acetic acid was added while maintaining the resultant mixture at 3 占 폚 or lower. To the obtained mixture, 12.6 parts of 4-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 40 占 폚 for 40 minutes. To the resultant mixture was added 456 parts of methanol, and the mixture was stirred at 40 DEG C for 3 hours and then at room temperature for 37 hours. To the obtained mixture, 3.14 parts of acetic acid, 6.31 parts of 4-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 124 parts of methanol were added, and the mixture was stirred at 40 占 폚 for 6 hours and 40 minutes. The resulting mixture was stirred at room temperature for 18 hours. The resulting mixture was filtered, and the residue was washed with 554 parts of methanol. 1740 parts of N, N-dimethylformamide was added to the obtained residue, stirred at 80 DEG C, and then filtered while being kept at 80 DEG C. [ To obtain a residue and a filtrate (ROE-1). The obtained residue was washed with 150 parts of N, N-dimethylformamide. And a residue and a cleaning liquid (SEN-1) were obtained. The obtained residue was dried under reduced pressure at 60 ° C to obtain 4.88 parts of a compound (Compound 114) represented by the formula (I-5). The obtained filtrate (ROE-1) and the washing solution (SEN-1) were combined and allowed to stand at room temperature for 12 hours. The resulting mixture was filtered, and the residue was washed three times with N, N-dimethylformamide in the same volume as the residue. The obtained residue was dried under reduced pressure at 60 ° C to obtain 5.16 parts of a compound represented by the formula (I-5) (Compound 114).

<Identification of Compound (Compound 114) Represented by Formula (I-5)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 470

                         Exact Mass: 469

Synthetic Example 6

10.0 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 93 parts of methanol were mixed. A mixture of 11.7 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 110 parts of methanol was added dropwise to the resulting mixture at a temperature of 2 ° C over a period of 1 hour and 15 minutes. The resulting mixture was stirred at 5 占 폚 for 3 hours. To the resulting mixture, while maintaining the temperature below 5 占 폚, 7.71 parts of acetic acid and 8 parts of methanol were added. To the obtained mixture, 11.4 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added. The resulting mixture was stirred at 2 占 폚 for 40 minutes and then stirred at room temperature for 17 hours and 40 minutes. 109 parts of methanol was added to the resulting mixture, and the mixture was stirred at room temperature for 1 hour and 20 minutes. To the obtained mixture, 6.41 parts of acetic acid, 10.1 parts of barbituric acid and 16.0 parts of methanol were added. The obtained mixture was stirred at room temperature for 5 hours and then at 40 ° C for 2 hours. To the resultant mixture was added 344 parts of water. The resulting mixture was stirred at 40 占 폚 for 3 hours and 25 minutes, and then stirred at room temperature for 16 hours. The obtained mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 1.55 parts of a compound (Compound 466) represented by the formula (I-6).

<Identification of Compound (Compound 466) Represented by Formula (I-6)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 385

                         Exact Mass: 384

Synthetic Example 7

5.00 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 42.0 parts of methanol were mixed. A mixture of 5.83 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 52.5 parts of methanol was added dropwise to the obtained mixture over 1 hour and 30 minutes while maintaining the temperature at 2 占 폚. The resulting mixture was stirred at 2 캜 for 6 hours. To the resultant mixture was added 7.59 parts of acetic acid while maintaining the temperature at 4 캜 or lower, and further 17.4 parts of 4-cyanoacetyl benzoate (synthesized in accordance with the method described in Japanese Patent Application Laid-Open No. 8-176154) and 682 parts of methanol . The resulting mixture was stirred at room temperature for 4 hours and then at 40 ° C for 48 hours. The obtained mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 2.21 parts of a compound represented by the formula (I-7) (Compound 139).

<Identification of Compound (Compound 139) Represented by Formula (I-7)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 518

                         Exact Mass: 517

Synthetic Example 8

8.10 parts of 4-nitropthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 69.0 parts of methanol were mixed. A mixture of 4.68 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 45.0 parts of methanol was added dropwise to the obtained mixture over 50 minutes while maintaining the temperature at 2 占 폚. The obtained mixture was stirred at 2 占 폚 for 2 hours and 30 minutes. 7.35 parts of acetic acid and 18.7 parts of phenylsulfonylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the resulting mixture while maintaining the temperature at 2 占 폚. The obtained mixture was stirred at room temperature for 15 hours and then at 40 ° C for 50 hours. The obtained mixture was divided in half to obtain Mixture 1 and Mixture 2.

The mixture 1 was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.0273 part of a compound (Compound 270) represented by the formula (I-8).

2.00 parts of acetic acid, 3.02 parts of barbituric acid, 50 parts of methanol and 102 parts of water were added to the mixture 2, followed by stirring at 40 占 폚 for 12 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.0313 parts of a compound (Compound 634) represented by the formula (I-9).

<Identification of Compound (Compound 270) Represented by Formula (I-8)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 519

                         Exact Mass: 518

<Identification of Compound (Compound 634) Represented by Formula (I-9)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 466

                         Exact Mass: 465

Synthesis Example 9

(I-10) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 3-chlorobenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 113) was obtained.

<Identification of Compound (Compound 113) Represented by Formula (I-10)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 470

                         Exact Mass: 469

Synthetic Example 10

(Compound 138) represented by the formula (I-11) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was changed to methyl 3-cyanoacetylbenzoate while maintaining the molar ratio .

<Identification of Compound (Compound 138) Represented by Formula (I-11)>

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 518

                         Exact Mass: 517

Synthetic Example 11

(I-12) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with phenylsulfonylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) while maintaining the molar ratio thereof. (Compound 183).

<Identification of Compound (Compound 183) Represented by Formula (I-12)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 474

                         Exact Mass: 473

Synthesis Example 12

(I-13) was obtained in the same manner as in Synthesis Example 7 except that 2-methylbenzoyl acetonitrile (manufactured by Sigma-Aldrich Japan K.K.) was used while maintaining the molar ratio of 4-cyano acetylbenzoate (Compound 103) was obtained.

<Identification of Compound (Compound 103) Represented by Formula (I-13)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 430

                         Exact Mass: 429

Synthetic Example 13

(I-14) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 3-methylbenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 104) was obtained.

<Identification of Compound (Compound 104) Represented by Formula (I-14)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 430

                         Exact Mass: 429

Synthetic Example 14

(I-15) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-methylbenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 105) was obtained.

<Identification of Compound (Compound 105) Represented by Formula (I-15)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 430

                         Exact Mass: 429

Synthetic Example 15

(Compound 140) represented by the formula (I-16) was obtained in the same manner as in the Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 2-nitrobenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 140) Represented by Formula (I-16)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 492

                         Exact Mass: 491

Synthetic Example 16

Compound (141) represented by the formula (I-17) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 3-nitrobenzoyl acetonitrile while maintaining the molar ratio.

<Identification of Compound (Compound 141) Represented by Formula (I-17)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 492

                         Exact Mass: 491

Synthetic Example 17

Compound (142) represented by the formula (I-18) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 4-nitrobenzoyl acetonitrile while maintaining the molar ratio.

<Identification of Compound (Compound 142) Represented by Formula (I-18)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 492

                         Exact Mass: 491

Synthetic Example 18

(Compound 121) represented by the formula (I-19) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 4-cyanobenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 121) Represented by Formula (I-19)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 452

                         Exact Mass: 451

Synthetic Example 19

Compound (147) represented by the formula (I-20) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 3-dimethylaminobenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 147) Represented by Formula (I-20)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 488

                         Exact Mass: 487

Synthetic Example 20

Compound (165) represented by the formula (I-21) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 1-naphthoyl acetonitrile while maintaining the molar ratio.

<Identification of Compound (Compound 165) Represented by Formula (I-21)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 502

                         Exact Mass: 501

Synthetic Example 21

Compound (166) represented by formula (I-22) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 2-naphthoyl acetonitrile while maintaining the molar ratio.

<Identification of Compound (Compound 166) Represented by Formula (I-22)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 502

                         Exact Mass: 501

Synthesis Example 22

(Compound 106) represented by the formula (I-23) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 2-trifluoromethylbenzoyl acetonitrile while maintaining the molar ratio thereof. &Lt; / RTI &gt;

<Identification of Compound (Compound 106) Represented by Formula (I-23)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 538

                         Exact Mass: 537

Synthetic Example 23

(I-24) was obtained in the same manner as in Synthetic Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 3-trifluoromethylbenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. ) (Compound 107) was obtained.

<Identification of Compound (Compound 107) Represented by Formula (I-24)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 538

                         Exact Mass: 537

Synthetic Example 24

(I-25) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-trifluoromethylbenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. ) (Compound 108) was obtained.

<Identification of Compound (Compound 108) Represented by Formula (I-25)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 538

                         Exact Mass: 537

Synthetic Example 25

(I-26) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 2-fluorobenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 109) was obtained.

<Identification of Compound (Compound 109) Represented by Formula (I-26)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 438

                         Exact Mass: 437

Synthetic Example 26

A compound (Compound 110) represented by the formula (I-27) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 3-fluorobenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 110) Represented by Formula (I-27)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 438

                         Exact Mass: 437

Synthetic Example 27

(I-28) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-fluorobenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 111) was obtained.

<Identification of Compound (Compound 111) Represented by Formula (I-28)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 438

                         Exact Mass: 437

Synthetic Example 28

A compound (Compound 115) represented by the formula (I-29) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 2-bromobenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 115) Represented by Formula (I-29)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 558

                         Exact Mass: 557

Synthetic Example 29

(Compound 116) represented by the formula (I-30) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 3-bromobenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 116) Represented by Formula (I-30)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 558

                         Exact Mass: 557

Synthetic Example 30

(I-31) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-bromobenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 117) was obtained.

<Identification of Compound (Compound 117) Represented by Formula (I-31)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 558

                         Exact Mass: 557

Synthetic Example 31

(Compound 125) represented by the formula (I-32) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 2-methoxybenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 125) Represented by Formula (I-32)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 462

                         Exact Mass: 461

Synthetic Example 32

A compound (Compound 126) represented by the formula (I-33) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 3-methoxybenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 126) Represented by Formula (I-33)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 462

                         Exact Mass: 461

Synthetic Example 33

(I-34) was obtained in the same manner as in Synthetic Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 4-methoxybenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 127) was obtained.

<Identification of Compound (Compound 127) Represented by Formula (I-34)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 462

                         Exact Mass: 461

Synthetic Example 34

13.8 parts of 4-nitropthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 115 parts of methanol were mixed. A mixture of 7.94 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 74.0 parts of methanol was added dropwise to the resulting mixture while maintaining the temperature at 2 to 3 占 폚 for 40 minutes. The resulting mixture was stirred at 2 to 3 占 폚 for 4 hours. While maintaining the resultant mixture at 3 占 폚 or lower, 12.5 parts of acetic acid was added, followed by addition of 25.4 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 150 parts of methanol. The resulting mixture was stirred at room temperature for 18 hours and then at 43 占 폚 for 5 hours with stirring. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 1.02 parts of a compound (Compound 189) represented by the formula (I-35).

<Identification of Compound (Compound 189) Represented by Formula (I-35)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 447

                         Exact Mass: 446

Synthetic Example 35

(I-36) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 3,4-dichlorobenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 118) was obtained.

<Identification of Compound (Compound 118) Represented by Formula (I-36)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 538

                         Exact Mass: 537

Synthetic Example 36

Synthesis Example 7 (Synthesis Example 7) was repeated except that methyl 4-cyanoacetylbenzoate was changed to (5,6,7,8-tetrahydro-2-naphthoyl) acetonitrile (manufactured by Sigma Aldrich Japan K.K.) , A compound represented by the formula (I-37) (Compound 167) was obtained in the same manner as in the above.

<Identification of Compound (Compound 167) Represented by Formula (I-37)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 510

                         Exact Mass: 509

Synthesis Example 37

(I-38) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 4-dimethylaminobenzoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 148) was obtained.

<Identification of Compound (Compound 148) Represented by Formula (I-38)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 488

                         Exact Mass: 487

Synthetic Example 38

(I-39) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with methylsulfonylacetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 182).

<Identification of Compound (Compound 182) Represented by Formula (I-39)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 350

                         Exact Mass: 349

Synthetic Example 39

Was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to (4-bromophenylsulfonyl) acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. -40) (Compound 184) was obtained.

<Identification of Compound (Compound 184) Represented by Formula (I-40)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 630

                         Exact Mass: 629

Synthetic Example 40

(Compound 137) represented by the formula (I-41) was obtained in the same manner as in the Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to methyl 2-cyanoacetylbenzoate while maintaining the molar ratio thereof. .

<Identification of Compound (Compound 137) Represented by Formula (I-41)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 518

                         Exact Mass: 517

Synthesis Example 41

(Compound 157) represented by the formula (I-42) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-sulfamoylbenzoyl acetonitrile while maintaining the molar ratio thereof. .

Synthetic Example 42

(Compound 134) represented by the formula (I-43) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was changed to 2-cyanoacetylbenzoic acid while maintaining the molar ratio .

<Identification of Compound (Compound 134) Represented by Formula (I-43)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 488

                         Exact Mass: 489

Synthetic Example 43

(Compound 135) represented by the formula (I-44) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was changed to 3-cyanoacetylbenzoic acid while maintaining the molar ratio .

<Identification of Compound (Compound 135) Represented by Formula (I-44)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 488

                         Exact Mass: 489

Synthetic Example 44

(Compound 136) represented by the formula (I-45) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was changed to 4-cyanoacetylbenzoic acid while maintaining the molar ratio .

<Identification of Compound (Compound 136) Represented by Formula (I-45)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 488

                         Exact Mass: 489

Synthetic Example 45

(Compound 120) represented by the formula (I-46) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 3-cyanobenzoyl acetonitrile while maintaining the molar ratio thereof. .

Synthetic Example 46

(Compound 122) represented by the formula (I-47) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced by 2-hydroxybenzoyl acetonitrile while maintaining the molar ratio thereof. .

<Identification of Compound (Compound 122) Represented by Formula (I-47)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 434

                         Exact Mass: 433

Synthetic Example 47

(Compound 123) represented by the formula (I-48) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 3-hydroxybenzoyl acetonitrile while maintaining the molar ratio thereof. .

<Identification of Compound (Compound 123) Represented by Formula (I-48)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 434

                         Exact Mass: 433

Synthetic Example 48

(Compound 124) represented by the formula (I-49) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was changed to 4-hydroxybenzoyl acetonitrile while maintaining the molar ratio thereof. .

<Identification of Compound (Compound 124) Represented by Formula (I-49)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 434

                         Exact Mass: 433

Synthetic Example 49

(Compound 143) represented by the formula (I-50) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 2-aminobenzoyl acetonitrile while maintaining the molar ratio .

Synthetic Example 50

(Compound 144) represented by the formula (I-51) was obtained in the same manner as in the Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to 3-aminobenzoyl acetonitrile while maintaining the molar ratio thereof .

Synthetic Example 51

(Compound 145) represented by the formula (I-52) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-aminobenzoyl acetonitrile while maintaining the molar ratio .

Synthetic Example 52

(Compound 133) represented by the formula (I-53) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-acetylbenzoyl acetonitrile while maintaining the molar ratio .

<Identification of Compound (Compound 133) Represented by Formula (I-53)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 486

                         Exact Mass: 485

Synthetic Example 53

(Compound 151) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-diethylaminobenzoyl acetonitrile while maintaining the molar ratio thereof. .

Synthetic Example 54

(Compound 130) represented by the formula (I-55) was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was replaced with 4-methylthiobenzoyl acetonitrile while maintaining the molar ratio thereof. .

Synthetic Example 55

(I-56) was obtained in the same manner as in Synthetic Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with (4-acetylaminophenylsulfonyl) acetonitrile while maintaining the molar ratio thereof. Compound 185).

Synthetic Example 56

Compound (186) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with (2-pyridylsulfonyl) acetonitrile while maintaining the molar ratio thereof. ).

Synthetic Example 57

(I-58) was carried out in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to N-octyl- ((4-cyanoacetyl) phenyl) sulfonamide while maintaining the molar ratio, (Compound 164) shown below.

Synthetic Example 58

(4-cyanoacetyl) phenyl) sulfonamide was obtained in the same manner as in Synthesis Example 7, except that methyl 4-cyanoacetylbenzoate was changed to N, N-dibutyl- ( -59) (Compound 160).

Synthetic Example 59

(I-2) was obtained in the same manner as in Synthesis Example 7 except that methyl 4-cyanoacetylbenzoate was changed to N, N-diphenyl- ((4-cyanoacetyl) phenyl) sulfonamide while maintaining the molar ratio thereof. 60) is obtained (Compound 161).

Synthetic Example 60

0.513 part of the compound represented by the formula (I-3) obtained in Synthesis Example 3 was added while stirring 7.6 parts of fuming sulfuric acid (25%) at 3 占 폚 (manufactured by Wako Pure Chemical Industries, Ltd.). To the resulting mixture, 3.8 parts of fuming sulfuric acid (25%) (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The resulting mixture was heated to 15 DEG C over 3 hours and 30 minutes while stirring. 139 parts of ice water were added to the resulting mixture, and further 38.2 parts of sodium chloride was added. The resulting mixture was filtered, and the obtained residue was washed with 64 parts of an aqueous 21.5% sodium chloride solution. The obtained residue was dried under reduced pressure at 60 캜 to obtain 1.02 parts of a compound represented by the formula (I-61) (compound having two sulfo groups bonded to the compound 102).

<Identification of the compound represented by the formula (I-61) (compound having two sulfo groups bonded to the compound 102)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 560

                         Exact Mass: 561

Synthetic Example 61

12.2 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 103 parts of methanol were mixed. A mixture of 14.3 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 130 parts of methanol was added dropwise to the resulting mixture over 2 hours and 10 minutes while maintaining the temperature at 4 to 6 占 폚. The obtained mixture was stirred at 4 to 6 占 폚 for 6 hours. 9.37 parts of acetic acid and 13.8 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the resulting mixture while keeping the temperature below 5 占 폚. The resulting mixture was stirred at room temperature for 15 hours. 1.00 parts of acetic acid and 1.39 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture, and the mixture was stirred at room temperature for 3 hours and at 40 占 폚 for 2 hours and 30 minutes. 1.44 parts of acetic acid and 2.13 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture, followed by stirring at 40 占 폚 for 3 hours. 0.985 parts of acetic acid, 1.46 parts of benzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 170 parts of methanol were added to the obtained mixture, followed by stirring at 40 占 폚 for 2 hours. 9.29 parts of acetic acid, 12.2 parts of barbituric acid and 17 parts of methanol were added to the obtained mixture, followed by stirring at 40 占 폚 for 20 hours. 9.29 parts of acetic acid, 14.4 parts of barbituric acid and 14 parts of methanol were added to the resulting mixture, and the mixture was stirred at 40 占 폚 for 18 hours. The resulting mixture was filtered. The obtained residue was washed twice with a mixture of 200 parts of water and 200 parts of methanol once with a mixture of 219 parts of water and 219 parts of methanol and once with 500 parts of water. The obtained residue was dried under reduced pressure at 60 캜 to obtain 31.3 parts of a mixture containing a compound (Compound 102) represented by the formula (I-3) and a compound represented by the formula (I-6) (Compound 466).

<Identification of Compound (Compound 102) Represented by Formula (I-3)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 402

                         Exact Mass: 401

<Identification of Compound (Compound 466) Represented by Formula (I-6)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 385

                         Exact Mass: 384

Synthetic Example 62

11.5 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 136 parts of methanol were mixed. A mixture of 13.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 101 parts of methanol was added dropwise to the resulting mixture while keeping the temperature at 2-4 캜 for 1 hour. The resulting mixture was stirred for 6 hours while keeping the temperature below 5 캜. To the resulting mixture was added 8.88 parts of acetic acid, 3.2 parts of methanol and 16.3 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) while maintaining the temperature at 4 to 8 占 폚. The resulting mixture was stirred at room temperature for 16 hours. 1.02 parts of acetic acid, 1.64 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 10 parts of methanol were added to the obtained mixture, and the mixture was stirred at room temperature for 1.5 hours and then at 40 占 폚 for 6 hours. 1.35 parts of acetic acid, 2.44 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 10 parts of methanol were added to the obtained mixture, followed by stirring at 40 占 폚 for 3 hours. To the resulting mixture was added 1.16 parts of acetic acid, 2.03 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 10 parts of methanol, and the mixture was stirred at 40 占 폚 for 17 hours. 8.83 parts of acetic acid, 12.6 parts of barbituric acid and 14 parts of methanol were added to the obtained mixture, and the mixture was stirred at 40 占 폚 for 22 hours. 4.40 parts of acetic acid, 5.75 parts of barbituric acid and 14 parts of methanol were added to the obtained mixture, and the mixture was stirred at 40 占 폚 for 9 hours and then at room temperature for 4 hours. The resulting mixture was filtered. The obtained residue was washed once with 393 parts of methanol once, and once with 393 parts of water and 393 parts of methanol. 800 parts of methanol was added to the obtained residue, and the mixture was stirred at 40 占 폚 for 2 hours. The resulting mixture was filtered. The obtained residue was dried under reduced pressure at 40 ° C to obtain 40.7 parts of a mixture containing a compound (Compound 112) represented by the formula (I-4) and a compound represented by the formula (I-63) (Compound 476).

<Identification of Compound (Compound 112) Represented by Formula (I-4)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 470

                         Exact Mass: 469

<Identification of compound (compound 476) represented by formula (I-63)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 419

                         Exact Mass: 418

Synthetic Example 63

(Compound 114) and Compound (I) were obtained in the same manner as in Synthesis Example 62 except that 2-chlorobenzoyl acetonitrile was changed to 4-chlorobenzoyl acetonitrile while maintaining the molar ratio thereof. -64) (compound 478) was obtained.

<Identification of Compound (Compound 114) Represented by Formula (I-5)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 470

                         Exact Mass: 469

<Identification of Compound (Compound 478) Represented by Formula (I-64)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 419

                         Exact Mass: 418

Synthetic Example 64

(Compound 101) and Compound (I-1) were obtained in the same manner as in Synthesis Example 62 except that 2-chlorobenzoyl acetonitrile was changed to pivaloyl acetonitrile while maintaining the molar ratio. 65) (Compound 465) was obtained.

<Identification of Compound (Compound 101) Represented by Formula (I-1)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 362

                         Exact Mass: 361

<Identification of Compound (Compound 465) Represented by Formula (I-65)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 365

                         Exact Mass: 364

Synthesis Example 65

Compound (199) and Compound (I-67) represented by Formula (I-66) were obtained in the same manner as in Synthesis Example 62 except that phthalonitrile was changed to 4-nitropthalonitrile while maintaining the molar ratio. ) (Compound 563) was obtained.

<Identification of Compound (Compound 199) Represented by Formula (I-66)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 515

                         Exact Mass: 514

<Identification of Compound (Compound 563) Represented by Formula (I-67)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 464

                         Exact Mass: 463

Synthetic Example 66

Except that phthalonitrile was changed to 4-nitrophthalonitrile while maintaining the molar ratio and 2-chlorobenzoyl acetonitrile was changed to 4-chlorobenzoyl acetonitrile while maintaining the molar ratio, A mixture containing a compound (Compound 201) represented by Formula (I-68) and a compound represented by Formula (I-69) (Compound 565) was obtained.

<Identification of Compound (Compound 201) Represented by Formula (I-68)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 515

                         Exact Mass: 514

<Identification of Compound (Compound 565) Represented by Formula (I-69)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 464

                         Exact Mass: 463

Synthesis Example 67

Except that the molar ratio of phthalonitrile was changed to 4-nitropthalonitrile while 2-chlorobenzoyl acetonitrile was changed to pivaloyl acetonitrile while maintaining the molar ratio of 2-chlorobenzoyl acetonitrile, the reaction was carried out in the same manner as in Synthesis Example 62, (Compound 188) represented by the formula (I-2) and the compound represented by the formula (I-70) (compound 552) was obtained.

<Identification of Compound (Compound 188) Represented by Formula (I-2)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 407

                         Exact Mass: 406

<Identification of compound (compound 552) represented by formula (I-70)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 410

                         Exact Mass: 409

Synthesis Example 68

Except that phthalonitrile was changed to 4-nitropthalonitrile while maintaining the molar ratio, and 2-chlorobenzoyl acetonitrile was changed to benzoyl acetonitrile while maintaining the molar ratio thereof. -35) (compound 189) and the compound represented by formula (I-72) (compound 553) were obtained.

<Identification of Compound (Compound 189) Represented by Formula (I-35)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 447

                         Exact Mass: 446

<Identification of Compound (Compound 553) Represented by Formula (I-72)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 430

                         Exact Mass: 429

Synthetic Example 69

Compound (112) represented by formula (I-4) and compound represented by formula (I-73) were obtained in the same manner as in Synthesis Example 62 except that barbituric acid was changed to benzoyl acetonitrile while maintaining the molar ratio. (Compound 7) was obtained.

<Identification of Compound (Compound 112) Represented by Formula (I-4)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 470

                         Exact Mass: 469

<Identification of Compound (Compound 7) Represented by Formula (I-73)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 436

                         Exact Mass: 435

Synthetic Example 70

Chlorobenzoyl acetonitrile was changed to 4-chloroacetonitrile while maintaining the molar ratio, and the same procedure as in Synthesis Example 62 was carried out except that benzoyl acetonitrile was used while keeping the molar ratio of barbituric acid, ) (Compound 114) and the compound represented by Formula (I-74) (Compound 8) were obtained.

<Identification of Compound (Compound 114) Represented by Formula (I-5)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 470

                         Exact Mass: 469

<Identification of Compound (Compound 8) Represented by Formula (I-74)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 436

                         Exact Mass: 435

Synthesis Example 71

(I-66) was obtained in the same manner as in Synthesis Example 62 except that phthalonitrile was changed to 4-nitropthalonitrile while maintaining the molar ratio, and that of bovisulfic acid was changed to benzoyl acetonitrile while maintaining the molar ratio A mixture containing a compound represented by the formula (199) and a compound represented by the formula (I-75) (9) was obtained.

<Identification of Compound (Compound 199) Represented by Formula (I-66)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 515

                         Exact Mass: 514

<Identification of Compound (Compound 9) Represented by Formula (I-75)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 481

                         Exact Mass: 480

Synthetic Example 72

N-chloroperbenzoyl acetonitrile was changed to 4-chlorobenzoyl acetonitrile while maintaining the molar ratio of 2-chlorobenzoyl acetonitrile while benzotriacetonitrile was used while maintaining the molar ratio of benzotriazole A mixture containing a compound (Compound 201) represented by the formula (I-68) and a compound (Compound 10) represented by the formula (I-76) was obtained in the same manner as in Synthesis Example 62,

<Identification of Compound (Compound 201) Represented by Formula (I-68)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 515

                         Exact Mass: 514

<Identification of Compound (Compound 10) Represented by Formula (I-76)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 481

                         Exact Mass: 480

Synthetic Example 73

(Compound 102) represented by the formula (I-3) and the compound represented by the formula (I-3) were obtained in the same manner as in Synthesis Example 61 except that barbituric acid was changed to dimedone (manufactured by Tokyo Chemical Industry Co., To obtain a mixture containing the compound represented by formula (I-77) (compound 454).

<Identification of Compound (Compound 102) Represented by Formula (I-3)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 402

                         Exact Mass: 401

<Identification of Compound (Compound 454) Represented by Formula (I-77)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 397

                         Exact Mass: 396

Synthetic Example 74

(2-thienyl) propionitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio of methyl 4-cyanoacetylbenzoate in the same manner as in Synthesis Example 7 , A compound represented by the formula (I-78) (Compound 732) was obtained.

<Identification of Compound (Compound 732) Represented by Formula (I-78)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 414

                         Exact Mass: 413

Synthesis Example 75

(I-79) was obtained in the same manner as in Synthetic Example 7 except that methyl 4-cyanoacetylbenzoate was replaced with 2-furoyl acetonitrile (manufactured by Sigma Aldrich Japan K.K.) while maintaining the molar ratio thereof. (Compound 733) was obtained.

<Identification of Compound (Compound 733) Represented by Formula (I-79)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 382

                         Exact Mass: 381

Synthesis Example 76

(Compound 135) and Compound (I-44) were obtained in the same manner as in Synthesis Example 62 except that 2-chlorobenzoyl acetonitrile was changed to 3-cyano acetylbenzoic acid while maintaining the molar ratio thereof. 80) (Compound 499) was obtained.

<Identification of Compound (Compound 135) Represented by Formula (I-44)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 488

                         Exact Mass: 489

<Identification of Compound (Compound 499) Represented by Formula (I-80)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 427

                         Exact Mass: 428

Synthesis Example 77

Compound (136) represented by formula (I-45) and compound represented by formula (I-45) were obtained in the same manner as in Synthesis Example 62 except that 2-chlorobenzoyl acetonitrile was changed to 4-cyano acetylbenzoic acid while maintaining the molar ratio. 81) (Compound 500).

<Identification of Compound (Compound 136) Represented by Formula (I-45)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 488

                         Exact Mass: 489

<Identification of Compound (Compound 500) Represented by Formula (I-81)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 427

                         Exact Mass: 428

Synthetic Example 78

Except that phthalonitrile was changed to 4-nitrophthalonitrile while maintaining the molar ratio and 2-chlorobenzoyl acetonitrile was changed to 3-cyano acetylbenzoic acid while maintaining the molar ratio, A mixture containing a compound (Compound 222) represented by Formula (I-82) and a compound represented by Formula (I-83) (Compound 586) was obtained.

<Identification of Compound (Compound 222) Represented by Formula (I-82)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 533

                         Exact Mass: 534

<Identification of Compound (Compound 586) Represented by Formula (I-83)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 472

                         Exact Mass: 473

Synthetic Example 79

Except that the molar ratio of phthalonitrile was changed to 4-nitrophthalonitrile, and 2-chlorobenzoyl acetonitrile was changed to 4-cyano acetylbenzoic acid while maintaining the molar ratio, (Compound 223) represented by the formula (I-84) and the compound represented by the formula (I-85) (compound 587) was obtained.

<Identification of Compound (Compound 223) Represented by Formula (I-84)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 533

                         Exact Mass: 534

<Identification of Compound (Compound 587) Represented by Formula (I-85)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 472

                         Exact Mass: 473

Synthetic Example 80

(Compound 134) and Compound (I-43) were obtained in the same manner as in Synthesis Example 62 except that 2-chlorobenzoyl acetonitrile was changed to 2-cyano acetylbenzoic acid while maintaining the molar ratio thereof. 86) (compound 498) was obtained.

<Identification of Compound (Compound 134) Represented by Formula (I-43)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 488

                         Exact Mass: 489

&Lt; Identification of Compound (Compound 498) Represented by Formula (I-86)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 427

                         Exact Mass: 428

Synthetic Example 81

Except that the molar ratio of phthalonitrile was changed to 4-nitropthalonitrile and 2-chlorobenzoyl acetonitrile was changed to 2-cyanoacetylbenzoic acid while maintaining the molar ratio, A mixture containing a compound (Compound 221) represented by Formula (I-87) and a compound represented by Formula (I-88) (Compound 585) was obtained.

<Identification of Compound (Compound 221) Represented by Formula (I-87)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 533

                         Exact Mass: 534

<Identification of Compound (Compound 585) Represented by Formula (I-88)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 472

                         Exact Mass: 473

Raw material synthesis example 1

Lithium bis (trimethylsilyl) amide in a molar ratio of 3 times the number of moles of acetonitrile and 10 parts of methyl 4- (carboxymethyl) benzoate in a molar amount of 4 times the number of moles of 10 parts of methyl 4- (carboxymethyl) Amide and 130 parts of tetrahydrofuran. To this mixture was added a mixture of 10 parts of methyl 4- (carboxymethyl) benzoate and 90 parts of tetrahydrofuran, and the mixture was stirred at -78 ° C to room temperature for 16 hours. The obtained mixture was purified to obtain 8 parts of 4- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene.

<Identification of 4- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene>

(Mass analysis) Ionization mode = ESI-: m / z = [MH] ^- 202

                         Exact Mass: 203

Raw material synthesis example 2

Under the conditions of a temperature of -78 ° C., 5.5 times the number of moles of acetonitrile and 33 parts of methyl 4- (2-carboxyethyl) benzoate in the molar number of moles per mole of 33 parts of 4- (2-carboxyethyl) (Trimethylsilyl) amide and 890 parts of tetrahydrofuran. To this mixture, 33 parts of methyl 4- (2-carboxyethyl) benzoate was added, and the mixture was stirred at -78 ° C for 30 minutes. The resulting mixture was purified to obtain 29 parts of 4- (2-carboxyethyl) -1- (cyanomethylcarbonyl) benzene.

<Identification of 4- (2-carboxyethyl) -1- (cyanomethylcarbonyl) benzene>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 216

                         Exact Mass: 217

Raw material synthesis example 3

Lithium bis (trimethylsilyl) amide in a molar ratio of 3 times the number of moles of acetonitrile and 30 parts of methyl 2- (carboxymethyl) benzoate in a molar amount of 4 times the number of moles of 30 parts of methyl 2- (carboxymethyl) Amide and 270 parts of tetrahydrofuran. To this mixture was added a mixture of 30 parts of methyl 2- (carboxymethyl) benzoate and 270 parts of tetrahydrofuran, and the mixture was stirred at a temperature of -78 ° C to room temperature for 3 hours. The resulting mixture was purified to obtain 27 parts of 2- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene.

<Identification of 2- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene>

(Mass analysis) Ionization mode = ESI-: m / z = [MH] ^- 202

                         Exact Mass: 203

Raw material synthesis example 4

A mixed solution of 34 parts of acetonitrile and 4- (2- (methoxycarbonyl) ethyl) benzoic acid in a molar ratio of 6 times the number of moles of 4- (2- (methoxycarbonyl) ethyl) Of lithium bis (trimethylsilyl) amide having a molar number of 5.5 times and 1,200 parts of tetrahydrofuran. To this mixture was added 34 parts of 4- (2- (methoxycarbonyl) ethyl) benzoic acid, and the mixture was stirred at -78 ° C for 1 hour. The resulting mixture was purified by recrystallization using ethyl acetate and hexane to obtain 30 parts of 4- (2- (cyanomethylcarbonyl) ethyl) benzoic acid.

<Identification of 4- (2- (cyanomethylcarbonyl) ethyl) benzoic acid>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 216

                         Exact Mass: 217

Synthesis Example 5

(M-cresol) n-octylbenzoic acid, which is five times the number of moles of acetonitrile and 4- (methoxycarbonylmethyl) benzoic acid in the molar number of 5.5 times the number of moles of the 4- (methoxycarbonylmethyl) benzoic acid, Butyl lithium and 1100 parts of tetrahydrofuran was obtained. To this mixture was added 28 parts of 4- (methoxycarbonylmethyl) benzoic acid, and the mixture was stirred at -78 ° C for 15 minutes. The resulting mixture was purified by column chromatography to obtain 22 parts of 4- (cyanomethylcarbonylmethyl) benzoic acid.

<Identification of 4- (cyanomethylcarbonylmethyl) benzoic acid>

(Mass analysis) Ionization mode = ESI-: m / z = [MH] ^- 202

                         Exact Mass: 203

Example 6

(Methoxycarbonyl) -3-methoxybenzoic acid and 18 parts of 4- (methoxycarbonyl) -3-methoxybenzoic acid in a molar ratio of 4 times the number of moles of 4- Of lithium bis (trimethylsilyl) amide having a molar ratio of 3 times and 160 parts of tetrahydrofuran. To this mixture was added a mixture of 18 parts of 4- (methoxycarbonyl) -3-methoxybenzoic acid and 160 parts of tetrahydrofuran, and the mixture was stirred at -78 ° C to room temperature for 16 hours. The resulting mixture was purified to obtain 15 parts of 4- (cyanomethylcarbonyl) -3-methoxybenzoic acid.

<Identification of 4- (cyanomethylcarbonyl) -3-methoxybenzoic acid>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 218

                         Exact Mass: 219

Example 7

(Methoxycarbonyl) -2-methoxybenzoic acid, 14 parts of acetonitrile and 4 parts of 4- (methoxycarbonyl) -2-methoxybenzoic acid in a molar ratio of 4 times the number of moles of 4- Of lithium bis (trimethylsilyl) amide having a molar ratio of 3 times and 120 parts of tetrahydrofuran. To the mixture was added a mixture of 14 parts of 4- (methoxycarbonyl) -2-methoxybenzoic acid and 120 parts of tetrahydrofuran, and the mixture was stirred at a temperature of -78 ° C to room temperature for 16 hours. The resulting mixture was purified to obtain 13 parts of 4- (cyanomethylcarbonyl) -2-methoxybenzoic acid.

<Identification of 4- (cyanomethylcarbonyl) -2-methoxybenzoic acid>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 218

                         Exact Mass: 219

Synthetic Example 82

5 parts of 4-aminophthalonitrile and 40 parts of methanol were mixed. To the resulting mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the molar amount of 5 parts of 4-aminophthalonitrile while keeping the temperature below 5 占 폚. This mixture was stirred at 5 占 폚 for 3 hours and then at room temperature for 16 hours. Benzoyl acetonitrile having a molar number of 2.2 times the number of moles of 5-aminopthalonitrile and 5.3 parts of acetic acid were added to the resulting mixture. This mixture was stirred at room temperature for 32 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.3 part of a compound (Compound 21-55) represented by the formula (I-89).

<Identification of compound (Compound 21-55) represented by formula (I-89)>

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 417

                         Exact Mass: 416

Synthetic Example 83

5 parts of 4- (N-acetylamino) phthalonitrile and 40 parts of methanol were mixed. To the resulting mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the number of moles of 4- (N-acetylamino) phthalonitrile while keeping the temperature below 5 占 폚. This mixture was stirred at 5 占 폚 for 3 hours and then at room temperature for 16 hours. Benzoyl acetonitrile having a molar number of 2.2 times the number of moles of 4- (N-acetylamino) phthalonitrile and 5.3 parts of acetic acid was added to the resulting mixture. This mixture was stirred at room temperature for 16 hours. The obtained mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.2 part of a compound (Compound 21-185) represented by the formula (I-90).

<Identification of compound (Compound 21-185) represented by formula (I-90)>

(Mass analysis) Ionization mode = ESI +: m / z = [MH] ⁺ 459

                         Exact Mass: 458

Synthetic Example 84

3 parts of 4-carboxyphthalonitrile and 32 parts of ethanol were mixed. A 21% sodium ethoxide ethanol solution containing sodium ethoxide in a molar amount of 2.1 times the number of moles of 3-carboxy phthalonitrile was added to the resulting mixture at room temperature. This mixture was stirred at 60 占 폚 for 16 hours. Benzoyl acetonitrile having a molar number of 2.3 times the number of moles of 3-carboxy phthalonitrile and 9.4 parts of acetic acid were added to the obtained mixture. This mixture was stirred at 90 占 폚 for 20 hours. To the obtained mixture, 9.4 parts of acetic acid was added. This mixture was stirred at 90 占 폚 for 72 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.5 part of a compound (Compound 21-135) represented by the formula (I-91).

<Identification of Compound (Compound 21-135) Represented by Formula (I-91)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 444

                         Exact Mass: 445

Synthetic Example 85

3 parts of 4-carboxyphthalonitrile and 47 parts of ethanol were mixed. To the resulting mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide in a molar amount twice that of 3 parts of 4-carboxyphthalonitrile at room temperature. This mixture was stirred at 60 占 폚 for 16 hours. To the obtained mixture, 4-cyanoacetylbenzoic acid having a molar number of 2.3 times the molar amount of acetic acid (9.4 parts), 3-carboxyphthalonitrile (3 parts) and methanol (120 parts) was added. This mixture was stirred at 70 占 폚 for 96 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.2 part of a compound (Compound 21-144) represented by the formula (I-92).

<Identification of Compound (Compound 21-144) Represented by Formula (I-92)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 532

                         Exact Mass: 533

Synthesis Example 86

3 parts of 4,5-dichlorophthalonitrile and 48 parts of methanol were mixed. To the resulting mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide at a molar ratio of 1 mole of 3 parts of 4,5-dichlorophthalonitrile while keeping the temperature at 0 占 폚. This mixture was stirred at room temperature for 16 hours. To the resultant mixture were added 6.3 parts of acetic acid and 4-cyanoacetylbenzoic acid in a molar ratio of 2.2 times the molar amount of 3 parts of 4,5-dichlorophthalonitrile and 160 parts of methanol. This mixture was stirred at room temperature for 48 hours and then at 50 ° C for 16 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.6 part of a compound (Compound 21-40) represented by the formula (I-93).

<Identification of compound (Compound 21-40) represented by formula (I-93)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 556

                         Exact Mass: 557

Synthesis Example 87

5 parts of 4-methoxyphthalonitrile and 79 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 2.5 times the number of moles of 4-methoxyphthalonitrile was added to the resulting mixture while maintaining the temperature at 0 占 폚. This mixture was stirred at room temperature for 3 hours and then at 65 占 폚 for 3 hours with stirring. To the obtained mixture, 4-cyano acetylbenzoic acid having a molar number of 2.2 times the number of moles of 4-methoxyphthalonitrile, 160 parts of methanol and 21 parts of acetic acid were added. This mixture was stirred at room temperature for 64 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.6 part of a compound (Compound 21-169) represented by the formula (I-94).

<Identification of compound (Compound 21-169) represented by formula (I-94)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 518

                         Exact Mass: 519

Synthesis Example 88

5 parts of 4-methoxyphthalonitrile and 79 parts of methanol were mixed. To the resulting mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide in a molar amount twice the mole number of 4-methoxyphthalonitrile while maintaining the temperature at 0 占 폚. This mixture was stirred at 70 占 폚 for 5 hours. To the obtained mixture, 3-cyano acetylbenzoic acid having a molar number of 2.5 times the number of moles of 4-methoxyphthalonitrile, 160 parts of methanol and 21 parts of acetic acid were added. This mixture was stirred at room temperature for 68 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.6 part of a compound (Compound 21-168) represented by the formula (I-95).

<Identification of compound (Compound 21-168) represented by formula (I-95)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 518

                         Exact Mass: 519

Synthetic Example 89

8 parts of 4-methoxyphthalonitrile and 95 parts of methanol were mixed. At room temperature, a 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 2.5 times the number of moles of 4-methoxyphthalonitrile was added to the resulting mixture. This mixture was stirred at 65 占 폚 for 3 hours. To the obtained mixture, 2-cyano acetylbenzoic acid and 34 parts of acetic acid in a molar amount of 2.2 times the number of moles of 4-methoxyphthalonitrile were added. This mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.4 part of a compound (Compound 21-167) represented by the formula (I-96).

<Identification of Compound (Compound 21-167) Represented by Formula (I-96)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 518

                         Exact Mass: 519

Synthesis Example 90

2 parts of 4-carboxyphthalonitrile and 32 parts of methanol were mixed. To the resultant mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide in a molar amount twice the mole number of 4-carboxyphthalonitrile while maintaining the temperature at 0 占 폚. This mixture was stirred at 60 占 폚 for 6 hours. To the resulting mixture, 4.2 parts of acetic acid, 4- (carboxymethyl) -1- (cyanomethylcarbonyl) benzene having a molar number of 2.2 times the number of moles of 2-carboxyphthalonitrile and 95 parts of methanol were added. This mixture was stirred at 70 占 폚 for 16 hours.

The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.3 part of a compound represented by the formula (I-97) (Compound 22-4961).

<Identification of Compound (Compound 22-4961) Represented by Formula (I-97)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 560

                         Exact Mass: 561

Synthesis Example 91

6.51 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 58 parts of methanol were mixed. A mixture of 7.61 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 71 parts of methanol was added dropwise to the resulting mixture over 1 hour and 30 minutes while keeping the temperature below 5 占 폚. The resulting mixture was stirred at 5 占 폚 or lower for 12 hours. 15.0 parts of acetic acid was added to the resulting mixture while keeping the temperature below 5 占 폚, and then 30.2 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 927 parts of methanol were added. The resulting mixture was stirred at room temperature for 4 hours and then at 40 ° C for 96 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.882 parts of a compound (Compound 112) represented by the formula (I-4).

<Identification of Compound (Compound 112) Represented by Formula (I-4)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 470

                         Exact Mass: 469

Synthesis Example 92

5.44 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 64 parts of methanol were mixed. A mixture of 6.37 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 48 parts of methanol was added dropwise to the obtained mixture while keeping the temperature at 5 占 폚 or lower for 1 hour and 30 minutes. The resulting mixture was stirred for 12 hours while keeping the temperature below 5 캜. To the resulting mixture was added 4.20 parts of acetic acid, 742 parts of methanol and 7.69 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) while keeping the temperature below 5 占 폚. The resulting mixture was stirred at room temperature for 36 hours. 0.482 parts of acetic acid and 0.775 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the resulting mixture, and the mixture was stirred at room temperature for 3 hours and then at 40 占 폚 for 12 hours. 0.638 parts of acetic acid and 1.15 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture, followed by stirring at 40 占 폚 for 6 hours. 0.549 parts of acetic acid and 0.958 parts of 2-chlorobenzoyl acetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture, followed by stirring at 40 占 폚 for 36 hours. To the obtained mixture, 4.17 parts of acetic acid and 5.96 parts of barbituric acid were added, and the mixture was stirred at 40 占 폚 for 48 hours. 2.08 parts of acetic acid and 2.72 parts of barbituric acid were added to the resulting mixture, and the mixture was stirred at 40 占 폚 for 24 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.283 parts of a compound (Compound 476) represented by the formula (I-63).

<Identification of compound (compound 476) represented by formula (I-63)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 419

                         Exact Mass: 418

Synthesis Example 93

7.51 parts of 4,5-dichlorophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 130 parts of methanol were mixed. 7.41 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining the temperature at 0 占 폚 for 1 hour and 30 minutes. The resulting mixture was stirred at room temperature for 16 hours. To the resulting mixture at room temperature, 16.0 parts of acetic acid, 670 parts of methanol and 7.27 parts of 4-cyanoacetylbenzoic acid were added. The resulting mixture was stirred at room temperature for 12 hours and then at 50 ° C for 12 hours. To the resultant mixture was added 0.433 part of acetic acid and 0.733 part of 4-cyanoacetyl benzoic acid, followed by stirring at 50 DEG C for 6 hours. To the resulting mixture was added 0.573 part of acetic acid and 1.09 part of 4-cyanoacetyl benzoic acid, followed by stirring at 50 DEG C for 6 hours. 0.493 parts of acetic acid and 0.906 parts of 4-cyanoacetyl benzoic acid were added to the resulting mixture, and the mixture was stirred at 50 占 폚 for 12 hours. To the obtained mixture, 3.75 parts of acetic acid and 5.35 parts of barbituric acid were added, and the mixture was stirred at 50 占 폚 for 24 hours. To the resulting mixture, 1.87 parts of acetic acid and 2.44 parts of barbituric acid were added, and the mixture was stirred at 50 占 폚 for 24 hours. The obtained mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.252 parts of a compound (Compound 31-40) represented by the formula (I-98).

<Identification of Compound (Compound 31-40) Represented by Formula (I-98)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 495

                         Exact Mass: 496

Synthesis Example 94

2-chlorobenzoyl acetonitrile was changed to 4-cyano acetylbenzoic acid while maintaining the molar ratio, and benzoyl acetonitrile was changed to benzoyl acetonitrile while maintaining the molar ratio of bovisulphonic acid. 99) was obtained (Compound 01-10).

<Identification of Compound (Compound 01-10) Represented by Formula (I-99)> [

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 444

                         Exact Mass: 445

Synthesis Example 95

Phthalonitrile was changed to 4-nitrophthalonitrile while maintaining the molar ratio, 2-chlorobenzoyl acetonitrile was changed to 4-cyano acetylbenzoic acid while keeping the molar ratio, and benzoyl acetyl Compound (01-364) represented by formula (I-100) was obtained in the same manner as in Synthesis Example 92 except that nitrile was used.

<Identification of compound (Compound 01-364) represented by formula (I-100)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 489

                         Exact Mass: 490

Synthesis Example 96

Compound (01-124) represented by formula (I-101) was obtained in the same manner as in Synthesis Example 93 except that barbituric acid was changed to benzoyl acetonitrile while maintaining the molar ratio.

&Lt; Identification of compound (Compound 01-124) represented by formula (I-101)

(Mass analysis) Ionization mode = ESI-: m / z = [MH] ^- 512

                         Exact Mass: 513

Synthesis Example 97

2-chlorobenzoyl acetonitrile was changed to 2-cyanoacetylbenzoic acid while maintaining the molar ratio, and benzoyl acetonitrile was changed to benzoyl acetonitrile while maintaining the molar ratio of bovisulphonic acid. In this way, 102) was obtained (Compound 01-37).

<Identification of compound (Compound 01-37) represented by formula (I-102)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 444

                         Exact Mass: 445

Synthetic Example 98

2-chlorobenzoyl acetonitrile was changed to 2-cyano acetylbenzoic acid while the molar ratio of 2-cyano benzoyl acetonitrile was maintained, and benzoyl acetal Compound (01-391) represented by formula (I-103) was obtained in the same manner as in Synthesis Example 92 except that nitrile was used.

<Identification of compound (Compound 01-391) represented by formula (I-103)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 489

                         Exact Mass: 490

Synthesis Example 99

Cyanoacetylbenzoic acid was changed to 2-cyanoacetylbenzoic acid while maintaining the molar ratio and barbituric acid was changed to benzoyl acetonitrile while maintaining the molar ratio, 104) was obtained (Compound 01-151).

<Identification of Compound (Compound 01-151) Represented by Formula (I-104)> [

(Mass analysis) Ionization mode = ESI-: m / z = [MH] ^- 512

                         Exact Mass: 513

Synthetic Example 100

3 parts of 4-bromophthalonitrile and 24 parts of methanol were mixed. To the resulting mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the molar amount of 3 parts of 4-bromophthalonitrile while maintaining the temperature at 0 占 폚. The mixture was stirred at 0 ° C for 3 hours. To the obtained mixture, 4-cyanoacetylbenzoic acid and 3.1 parts of acetic acid in a molar ratio of 2.2 times the number of moles of 3-bromomethanitrile were added. This mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.3 part of a compound (Compound 21-294) represented by the formula (I-105).

<Identification of compound (Compound 21-294) represented by formula (I-105)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 566

                         Exact Mass: 567

Synthesis Example 101

5 parts of 3,4-dicyanobenzenesulfonic acid and 79 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the number of moles of 3,4-dicyanobenzenesulfonic acid was added to the resulting mixture while maintaining the temperature at 0 占 폚. This mixture was stirred at 0 占 폚 for 6 hours. To the resulting mixture was added 5.2 parts of 4-cyanoacetylbenzoic acid and acetic acid in a molar ratio of 2.2 times the number of moles of 3,4-dicyanobenzenesulfonic acid. This mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.4 part of a compound (Compound 21-219) represented by the formula (I-106).

<Identification of compound (Compound 21-219) represented by formula (I-106)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 568

                         Exact Mass: 569

Synthesis Example 102

2 parts of phthalonitrile and 16 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the number of moles of phthalonitrile was added to the resulting mixture while keeping the temperature at 5 占 폚. This mixture was stirred at 5 캜 for 3 hours. To the obtained mixture, N-acetyl-4- (cyanoacetyl) aniline and 2.2 parts of acetic acid in a molar ratio of 2.2 times the number of moles of phthalonitrile were added. This mixture was stirred at room temperature for 16 hours. To the obtained mixture, N-acetyl-4- (cyanoacetyl) aniline in a molar ratio of 1.1 times the molar amount of 2 parts of phthalonitrile was added. This mixture was stirred at room temperature for 16 hours and then at 50 DEG C for 48 hours.

The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.3 part of a compound represented by the formula (I-107) (Compound 154).

<Identification of Compound (Compound 154) Represented by Formula (I-107)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 516

                         Exact Mass: 515

Synthetic Example 103

2 parts of 4- (trifluoromethyl) phthalonitrile and 32 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.8 times the number of moles of 4- (trifluoromethyl) phthalonitrile was added to the resulting mixture while maintaining the temperature at 0 占 폚. This mixture was stirred at 10 캜 for 2 hours. To the resulting mixture was added 4-cyanoacetylbenzoic acid in a molar ratio of 2.2 times the number of moles of the acetic acid and 4.4 parts of 4- (trifluoromethyl) phthalonitrile. This mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.3 part of a compound (Compound 21-119) represented by the formula (I-108).

<Identification of compound (Compound 21-119) represented by formula (I-108)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 556

                         Exact Mass: 557

Synthetic Example 104

4 parts of 4- (trifluoromethyl) phthalonitrile and 32 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the number of moles of 4- (trifluoromethyl) phthalonitrile was added to the resulting mixture while maintaining the temperature at 0 占 폚. The mixture was stirred at 0 ° C for 3 hours. To the obtained mixture, 3-cyano acetylbenzoic acid and 4.4 parts of acetic acid in a molar ratio of 2.2 times the number of moles of 4- (trifluoromethyl) phthalonitrile were added. This mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.3 part of a compound (Compound 21-118) represented by the formula (I-109).

&Lt; Identification of compound (Compound 21-118) represented by formula (I-109)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 556

                         Exact Mass: 557

Synthesis Example 105

2.5 parts of 4- (trifluoromethyl) phthalonitrile and 79 parts of methanol were mixed. To the resulting mixture was added a 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the molar amount of 2.5 parts of 4- (trifluoromethyl) phthalonitrile while maintaining the temperature at 0 占 폚. The mixture was stirred at 0 ° C for 3 hours. To the obtained mixture, 2.2 parts of moles of 2-cyano acetylbenzoic acid and 3 parts of acetic acid were added to 2.5 parts of 4- (trifluoromethyl) phthalonitrile. This mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.1 part of a compound (Compound 21-117) represented by the formula (I-110).

&Lt; Identification of compound (Compound 21-117) represented by formula (I-110)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 556

                         Exact Mass: 557

Synthesis Example 106

2 parts of phthalonitrile and 16 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in a molar ratio of 0.5 times the number of moles of phthalonitrile was added to the resulting mixture while keeping the temperature at 5 占 폚. This mixture was stirred at 5 占 폚 for 3 hours and then at room temperature for 16 hours. To the resulting mixture was added 2.2 parts of 4-sulfamoylbenzoyl acetonitrile and 2.2 parts of acetic acid in a molar ratio of 2.2 times the number of moles of phthalonitrile. This mixture was stirred at room temperature for 16 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.3 part of a compound (Compound 157) represented by the formula (I-42).

<Identification of Compound (Compound 157) Represented by Formula (I-42)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 560

                         Exact Mass: 559

Synthesis Example 107

4.1 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 48 parts of methanol were mixed. A mixture of 4.8 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 36 parts of methanol was added dropwise to the resulting mixture while keeping the temperature at 5 캜 or lower for 1 hour and 30 minutes. The resulting mixture was stirred for 12 hours while keeping the temperature below 5 캜. To the resulting mixture was added 5.1 parts of acetic acid, 750 parts of methanol and 7.2 parts of 4-sulfamoyl benzoyl acetonitrile while keeping the temperature below 5 占 폚. The resulting mixture was stirred at room temperature for 36 hours. 0.56 parts of acetic acid and 0.73 part of 4-sulfamoyl benzoyl acetonitrile were added to the obtained mixture, and the mixture was stirred at room temperature for 3 hours and then at 40 ° C for 12 hours. 0.77 parts of acetic acid and 1.1 parts of 4-sulfamoyl benzoyl acetonitrile were added to the resulting mixture, followed by stirring at 40 占 폚 for 6 hours. 0.66 part of acetic acid and 0.90 part of 4-sulfamoyl benzoyl acetonitrile were added to the obtained mixture, followed by stirring at 40 占 폚 for 36 hours. 3.1 parts of acetic acid and 4.5 parts of barbituric acid were added to the obtained mixture, and the mixture was stirred at 40 占 폚 for 48 hours. 1.6 parts of acetic acid and 2.0 parts of barbituric acid were added to the obtained mixture, and the mixture was stirred at 40 占 폚 for 24 hours. The resulting mixture was subjected to solvent distillation using a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.21 part of a compound represented by the formula (I-111) (Compound 521).

<Identification of Compound (Compound 521) Represented by Formula (I-111)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 464

                         Exact Mass: 463

Synthetic Example 108

Compound (608) represented by formula (I-112) was obtained in the same manner as in Synthesis Example 107 except that phthalonitrile was changed to 4-nitropthalonitrile while maintaining the molar ratio.

<Identification of Compound (Compound 608) Represented by Formula (I-112)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 509

                         Exact Mass: 508

Synthetic Example 109

Compound (241) represented by formula (I-113) was obtained in the same manner as in Synthesis Example 102 except that phthalonitrile was changed to 4-nitropthalonitrile while maintaining the molar ratio.

<Identification of Compound (Compound 241) Represented by Formula (I-113)

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 561

                         Exact Mass: 560

Synthesis Example 110

Compound (244) represented by formula (I-114) was obtained in the same manner as in Synthesis Example 106 except that phthalonitrile was changed to 4-nitrophthalonitrile while maintaining the molar ratio.

<Identification of Compound (Compound 244) Represented by Formula (I-114)> [

(Mass analysis) Ionization mode = ESI +: m / z = [M + H] ⁺ 605

                         Exact Mass: 604

Synthesis Example 111

Compound (21-292) represented by the formula (I-115) was obtained in the same manner as in Synthesis Example 100 except that 4-cyanoacetylbenzoic acid was changed to 2-cyanoacetylbenzoic acid while maintaining the molar ratio.

<Identification of compound (Compound 21-292) represented by formula (I-115)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 566

                         Exact Mass: 567

Synthetic Example 112

Compound (21-293) represented by formula (I-116) was obtained in the same manner as in Synthesis Example 100 except that 4-cyanoacetylbenzoic acid was changed to 3-cyanoacetylbenzoic acid while maintaining the molar ratio.

&Lt; Identification of compound (Compound 21-293) represented by formula (I-116)

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 566

                         Exact Mass: 567

Synthesis Example 113

Compound (41-843) represented by the formula (I-117) was obtained in the same manner as in Synthesis Example 93 except that barbituric acid was changed to dimedone (manufactured by Tokyo Chemical Industry Co., Ltd.) while maintaining the molar ratio. ).

<Identification of Compound (Compound 41-843) Represented by Formula (I-117)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 507

                         Exact Mass: 508

Synthesis Example 114 Synthesis Example 165

Phthalonitrile was changed to a compound represented by the formula (PPA-1) using the group shown in the column of &quot; B ¹ B ² &quot; in Table 12, and 2-chlorobenzoyl acetonitrile was used in place of the &quot; Lk & Was replaced with the compound represented by the formula (PPA-2), the compound shown in the column of &quot; compound &quot; in Table 12 was obtained.

The compound obtained in each synthesis example is a compound represented by the formula (PPA-3) using "B ¹ B ² " in Table 12, "Lk" column and the group shown in column "Hd".

Identification of the compound was carried out by mass spectrometry.

(Mass analysis) ionization mode = ESI +: m / z = [M + H] ⁺ when the "ionization mode" column in Table 12 is "1" Respectively.

In the case of Table 12, "ionization mode" column is a "-1", (Mass Spec.) Ionization mode = ESI-: m / z = [ MH] - "detected value" of the value detected by the table 12 is Respectively.

&Quot; Exact.Mass. &Quot; in Table 12 shows the value of Exact.Mass.

In Table 12, the symbols (HH35, BB19, etc.) described in the column "B ¹ B ² " and the column "Hd" are the same as those in Tables 1 to 9 (b) and Tables 10 to 11 Are defined identically.

[Table 12]

Synthesis Examples 166 to 181

The synthesis was carried out in the same manner as in Synthetic Example 86 except that 4-cyanoacetylbenzoic acid was replaced with a compound represented by the formula (PPA-2) using the group shown in the column "Lk" and the column "Hd" &Quot; Compound &quot;

The compound obtained in each synthesis example is a compound represented by the formula (I-93a) using the groups shown in the column "Lk" and the column "Hd" in Table 13.

Identification of the compound was carried out by mass spectrometry.

The value detected by the (mass analysis) ionization mode = ESI +: m / z = [M + H] ⁺ when the "ionization mode" column of Table 13 is "1" Respectively.

When the "ionization mode" column in Table 13 is "-1", the value detected by the (mass analysis) ionization mode = ESI-: m / z = [MH] ^- Respectively.

&Quot; Exact.Mass. &Quot; in Table 13 shows the value of Exact.Mass.

In Table 13, the symbols (HH35, etc.) described in the column "Hd" are defined in the same manner as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of this specification.

[Table 13]

Synthesis Examples 182 to 223

Phthalonitrile was changed to a compound represented by the formula (PPA-1) using the group shown in the column of &quot; B ¹ B ² &quot; in Table 14, and 2-chlorobenzoyl acetonitrile was used in a ratio of &quot; Lk &quot; Was replaced with a compound represented by the formula (PPA-2) using the group shown in the column &quot; Compound &quot;.

The compound obtained in each of the synthesis examples is a compound represented by the formula (I-63a) using "B ¹ B ² " in Table 14, "Lk" column and "Hd" column.

Identification of the compound was carried out by mass spectrometry.

When the "ionization mode" column in Table 14 is "1", the value detected by the (mass analysis) ionization mode = ESI +: m / z = [M + H] ⁺ is referred to as " Respectively.

When the "ionization mode" column in Table 14 is "-1", the value detected by the (mass analysis) ionization mode = ESI-: m / z = [MH] ^- Respectively.

&Quot; Exact.Mass. &Quot; in Table 14 indicates the value of Exact.Mass.

In Table 14, the symbols in the column "B ¹ B ² " and in the column "Hd" are defined in the same manner as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of the present specification.

[Table 14]

Synthesis Example 224 to Synthesis Example 237

The same procedure as in Synthesis Example 93 was repeated except that 4-cyanoacetylbenzoic acid was replaced with a compound represented by the formula (PPA-2) using the group shown in column "Lk" and column "Hd" &Quot; Compound &quot;

The compound obtained in each synthesis example is a compound represented by the formula (I-98a) using the groups shown in the column "Lk" and the column "Hd" in Table 15.

Identification of the compound was carried out by mass spectrometry.

(Mass analysis) ionization mode = ESI +: m / z = [M + H] ⁺ when the "ionization mode" column in Table 15 is "1" Respectively.

The value detected by the (mass analysis) ionization mode = ESI-: m / z = [MH] ^- when the "ionization mode" column in Table 15 is "-1" Respectively.

The "Exact.Mass." Column in Table 15 shows the value of Exact.Mass.

In Table 15, the symbols in the column "Hd" are defined in the same manner as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of the present specification.

[Table 15]

Synthesis Example 238 to Synthesis Example 240

Phthalonitrile was changed to a compound represented by the formula (PPA-1) using the group shown in the column of &quot; B ¹ B ² &quot; in Table 16, and 2-chlorobenzoyl acetonitrile was used in the &quot; Lk & , The compound shown in the column of &quot; compound &quot; in Table 16 was obtained in the same manner as in Synthesis Example 92 except that the compound represented by the formula (PPA-2) was used instead of the compound represented by the formula &Lt; / RTI &gt;

The compound obtained in each of the synthesis examples is a compound represented by the formula (I-63b) using "B ¹ B ² " in Table 16, "Lk" and a group shown in the column "Hd".

Identification of the compound was carried out by mass spectrometry.

The value detected by the (mass spectrometry) ionization mode = ESI +: m / z = [M + H] ⁺ when the "ionization mode" column of Table 16 is "1" Respectively.

In the case of Table 16, "ionization mode" column is a "-1", (Mass Spec.) Ionization mode = ESI-: m / z = [ MH] - "detected value" of the value detected by the table 16 is Respectively.

The "Exact.Mass." Column in Table 16 shows the value of Exact.Mass.

In Table 16, the symbols in the column "B ¹ B ² " and the column "Hd" are defined in the same manner as the symbols in Tables 1 to 9 (b) and Tables 10 to 11 of the present specification.

[Table 16]

Synthetic Example 241

2-chlorobenzoyl acetonitrile was changed to 3-cyanoacetylbenzoic acid while maintaining the molar ratio, and benzoyl acetonitrile was changed to benzoyl acetonitrile while maintaining the molar ratio of bovisulphonic acid to the formula (I- 118) (Compound 01-24) was obtained.

<Identification of compound (Compound 01-24) represented by formula (I-118)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 444

                         Exact Mass: 445

Synthetic Example 242

Phthalonitrile was changed to 4-nitrophthalonitrile while maintaining the molar ratio, 2-chlorobenzoyl acetonitrile was changed to 3-cyano acetylbenzoic acid while keeping the molar ratio, and benzoyl acetyl Compound (01-378) represented by the formula (I-119) was obtained in the same manner as in Synthesis Example 92 except that the compound

<Identification of compound (Compound 01-378) represented by formula (I-119)>

(Mass spectrometry) Ionization mode = ESI-: m / z = [MH] ^- 489

                         Exact Mass: 490

Synthetic Example 243

4-cyanoacetylbenzoic acid was changed to 3-cyanoacetylbenzoic acid while maintaining the molar ratio, and benzoyl acetonitrile was changed to benzoyl acetonitrile while keeping the molar ratio of bovisulphonic acid, 120) was obtained (Compound 01-138).

<Identification of compound (Compound 01-138) represented by formula (I-120)>

(Mass analysis) Ionization mode = ESI-: m / z = [MH] ^- 512

                         Exact Mass: 513

Resin Synthesis Example 1

A proper amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the flask was purged with nitrogen atmosphere. 280 parts of propylene glycol monomethyl ether acetate was added and heated to 80 DEG C with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate and 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan- (289 parts) and propylene glycol monomethyl ether acetate (125 parts) was added dropwise over 5 hours. On the other hand, a mixed solution obtained by dissolving 33 parts of 2,2-azobis (2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B1) having a solid content of 35.0%. The resin B1 thus obtained had a weight average molecular weight of 8800, a dispersion degree of 2.1 and a solution acidity of 28 mg-KOH / g.

Resin Synthesis Example 2

A proper amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the flask was purged with a nitrogen atmosphere, and 350 parts of propylene glycol monomethyl ether acetate was added and heated to 85 DEG C with stirring. Subsequently, 70 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate or / and 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan- , A mixture of 202 parts of a mixture of maleic anhydride and methacrylic acid, 78 parts of vinyl toluene (isomer mixture) and 100 parts of propylene glycol monomethyl ether acetate was added dropwise over 4 hours. On the other hand, a solution obtained by dissolving 33 parts of polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 167 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the end of the dropwise addition of the initiator solution, the mixture was maintained at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B5) having a solid content of 38.1%. The resin B5 thus obtained had a weight average molecular weight of 10,400, a degree of dispersion of 2.03, and a solution acid value of 53 mg-KOH / g.

Resin Synthesis Example 3

A flask equipped with a reflux condenser, a dropping funnel and a stirrer was charged with an appropriate amount of nitrogen, replaced with nitrogen atmosphere, and 362 parts of propylene glycol monomethyl ether acetate was added and heated to 80 DEG C with stirring. Subsequently, 58 parts of acrylic acid, 3 parts of 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan-8-yl acrylate and / or 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decan- 167 parts of a mixture of 2-ethylhexyl acrylate, 65 parts of 2-ethylhexyl acrylate and 111 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution obtained by dissolving 27 parts of polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 210 parts of propylene glycol monomethyl ether acetate was added dropwise over 5.5 hours. After the addition of the initiator solution was completed, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B6) having a solid content of 29.8%. The resin B6 thus obtained had a weight-average molecular weight of 10900, a degree of dispersion of 2.25, and a solution acid value of 44 mg-KOH / g.

Comparative Example 1

Pigment: C.I. Pigment Green 58  47 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Pigment: C.I. Pigment Yellow 138  22 parts,

Dispersant 7.1 parts,

Suzy 9.3 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 140 parts

Were mixed, and the pigment was dispersed using a bead mill to obtain a pigment dispersion.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained pigment dispersion;

Resin (B): Resin B6 solution  48 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

 11 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.7 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE-

4.5 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.57 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 330 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) ` 0.090 part;

To obtain a comparative colored curable composition 1.

[Production of coloring pattern]

The comparative colored curable composition 1 was applied on a glass substrate (Eagle XG; Corning) having a size of 2 inches by 2 inches by spin coating, and then prebaked at 100 캜 for 3 minutes to form a colored curable composition layer. After cooling, an exposure amount of 80 mJ / cm &lt; 2 &gt; was formed in an atmospheric environment using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) with an interval of 200 mu m between the substrate on which the colored curable composition layer was formed and the quartz glass photomask (Based on 365 nm). As the photomask, a 100 μm line and space pattern was formed. The colored coating film after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 캜 for 70 seconds to develop and wash. This colored coating film was post-baked at 230 캜 for 30 minutes to obtain a colored pattern.

The film thickness of the obtained color pattern was measured using DEKTAK3 (manufactured by Japan Vacuum Technology Co., Ltd.). The film thickness of the colored pattern is shown in the column of &quot; film thickness &quot; in Table 17.

[Measurement of initial brightness]

Spectroscopy was measured using a colorimeter (OSP-SP-200, manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) in the XYZ color system of CIE were measured using the characteristic function of the C light source ) And the stimulus value Y were measured. The larger the value of Y, the higher the brightness.

[Evaluation of light resistance]

A light resistance tester (Line Test CPS + manufactured by Toyo Seiki Seisakusho Co., Ltd.) was placed on the obtained color pattern, and an ultraviolet cut filter (COLORED OPTICAL GLASS L38; HOYA CO., LTD. , A light resistance test was conducted in which xenon lamp light was irradiated for 15 hours. The relative value (%) of the stimulus value Y after the light resistance test when the stimulus value Y before the light resistance test (the initial lightness obtained above) is set to 100% is shown in the column of "brightness change rate" The closer the brightness change rate is to 100%, the higher the light resistance.

Example 1-1

Pigment: C.I. Pigment Green 58  47 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Colorant (A): A compound represented by the formula (I-1)  20 parts, and

Colorant (A): C.I. Pigment Yellow 138 2.2 part

The total amount of the pigment composition,

Dispersant (BYK-LPN6919; manufactured by BICKEMI Japan Co., Ltd.)  26

Resin (B): Resin B1 solution  44 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 350 parts

(I-1) and a mixture of C.I. Pigment Yellow 138 was dispersed to obtain a colored composition.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained coloring composition;

Resin (B): Resin B6 solution 8.3 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

9.9 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.0 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE-

4.0 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.50 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 110 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

To obtain a colored curable composition 1-1.

A colored pattern was obtained in the same manner as in Comparative Example 1 except that the comparative colored curable composition 1 was changed to the colored curable composition 1-1. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

Examples 1-2 to 1-60

Except that the compound represented by the formula (I-1) was replaced with the compound shown in the column of &quot; XXXXX &quot; in Table 17, To obtain a colored pattern. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

[Table 17]

Examples 1A-1

Pigment: C.I. Pigment Green 58  47 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Colorant (A): Compound 136  20 parts, and

Colorant (A): C.I. Pigment Yellow 138 2.2 part

The total amount of the pigment composition,

Dispersant solution (solid content 60%)  26 parts,

Resin (B): Resin B1 solution  44 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 350 parts

Were mixed. Using a bead mill, the compound 136 and C.I. Pigment Yellow 138 was dispersed to obtain a colored composition.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained coloring composition;

Resin (B): Resin B6 solution 8.3 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

9.9 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.0 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE-

4.0 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.50 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 110 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

To obtain a colored curable composition 1A-1.

A coloring pattern was obtained in the same manner as in Comparative Example 1 except that the comparative colored curable composition 1 was changed to the colored curable composition 1A-1. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

Examples 1A-2 to 1A-231

In the same manner as in Example 1A-1 except that the compound 136 was changed to the compound shown in the column of &quot; XXXXX &quot; in Tables 18 to 21, To obtain a colored pattern. In addition, initial brightness and light resistance were evaluated. The results are shown in the columns of "film thickness" and "brightness change ratio" in Tables 18 to 21.

[Table 18]

[Table 19]

[Table 20]

[Table 21]

Comparative Example 2

Pigment: C.I. Pigment Green 58  47 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Pigment: C.I. Pigment Yellow 138  22 parts,

Dispersant 7.1 parts,

Suzy 9.3 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 140 parts

Were mixed, and the pigment was dispersed using a bead mill to obtain a pigment dispersion.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained pigment dispersion;

Resin (B): Resin B6 solution  48 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

 11 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.7 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE-

4.5 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.57 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 330 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

Were mixed to obtain a comparative colored curable composition 2.

[Production of coloring pattern]

The comparative colored curable composition 2 was applied to a glass substrate (Eagle XG; Corning) having a size of 2 inches by 2 inches by spin coating, and then prebaked at 100 캜 for 3 minutes to form a colored curable composition layer. After cooling, an exposure amount of 80 mJ / cm &lt; 2 &gt; was formed in an atmospheric environment using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) with an interval of 200 mu m between the substrate on which the colored curable composition layer was formed and the quartz glass photomask (Based on 365 nm). As the photomask, a 100 μm line and space pattern was formed. The colored coating film after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 캜 for 70 seconds to develop and wash. This colored coating film was post-baked at 230 캜 for 30 minutes to obtain a colored pattern.

The film thickness of the obtained color pattern was measured using DEKTAK3 (manufactured by Japan Vacuum Technology Co., Ltd.). The film thickness of the colored pattern is shown in the column of &quot; film thickness &quot; in Table 22.

[Measurement of initial brightness]

Spectroscopy was measured using a colorimeter (OSP-SP-200, manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) in the XYZ color system of CIE were measured using the characteristic function of the C light source ) And the stimulus value Y were measured. The larger the value of Y, the higher the brightness.

[Evaluation of light resistance]

A light resistance tester (Line Test CPS + manufactured by Toyo Seiki Seisakusho Co., Ltd.) was placed on the obtained color pattern, and an ultraviolet cut filter (COLORED OPTICAL GLASS L38; HOYA CO., LTD. , A light resistance test was conducted in which xenon lamp light was irradiated for 15 hours. The relative value (%) of the stimulus value Y after the light resistance test when the stimulus value Y before the light resistance test (initial brightness obtained above) is set to 100% is shown in the column of &quot; The closer the brightness change rate is to 100%, the higher the light resistance.

Example 2-1

Pigment: C.I. Pigment Green 58  47 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Colorant (A): A compound represented by the formula (I-1)  20 parts, and

Colorant (A): C.I. Pigment Yellow 185 2.2 part

The total amount of the pigment composition,

Dispersant (BYK-LPN6919; manufactured by BICKEMI Japan Co., Ltd.)  26

Resin (B): Resin B1 solution  44 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 350 parts

(I-1) and a mixture of C.I. Pigment Yellow 185 was dispersed to obtain a coloring composition.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained coloring composition;

Resin (B): Resin B6 solution 8.3 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

9.9 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.0 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE- 4.0 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.50 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 110 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

To obtain a colored curable composition 2-1.

A colored pattern was obtained in the same manner as in Comparative Example 2 except that the comparative colored curable composition 2 was changed to the colored curable composition 2-1. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

Examples 2-2 to 2-60

Except that the compound represented by the formula (I-1) was replaced with the compound shown in the column of &quot; XXXXX &quot; in Table 22, the &quot; coloring curable composition To obtain a colored pattern. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

[Table 22]

Examples 2A-1

Pigment: C.I. Pigment Green 58  47 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate , And a pigment dispersion (liquid containing the colorant (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Colorant (A): Compound 136  20 parts, and

Colorant (A): C.I. Pigment Yellow 185 The total amount of the pigment composition comprising 2.2 parts,

Dispersant solution (solid content 60%)  26 parts,

Resin (B): Resin B1 solution  44 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate Were mixed. Using a bead mill, the compound 136 and C.I. Pigment Yellow 185 was dispersed to obtain a coloring composition.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained coloring composition;

Resin (B): Resin B6 solution 8.3 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

9.9 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.0 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE- 4.0 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.50 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 110 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part; To obtain a colored curable composition 2A-1.

A colored pattern was obtained in the same manner as in Comparative Example 2 except that the comparative colored curable composition 2 was changed to the colored curable composition 2A-1. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

Examples 2A-2 to 2A-231

In the same manner as in Example 2A-1 except that the compound 136 was changed to the compound shown in the column of &quot; XXXXX &quot; in Tables 23 to 26, To obtain a colored pattern. In addition, initial brightness and light resistance were evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 23 to 26.

[Table 23]

[Table 24]

[Table 25]

[Table 26]

Comparative Example 3

Pigment: C.I. Pigment Green 58  47 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Pigment: C.I. Pigment Yellow 138  22 parts,

Dispersant 7.1 parts,

Suzy 9.3 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 140 parts

Were mixed, and the pigment was dispersed using a bead mill to obtain a pigment dispersion.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained pigment dispersion;

Resin (B): Resin B6 solution  48 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

 11 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.7 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE- 4.5 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.57 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 330 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

To obtain a comparative colored curable composition 3.

[Production of coloring pattern]

The comparative colored curable composition 3 was coated on a glass substrate (Eagle XG; Corning) having a size of 2 inches by 2 inches by spin coating, and then prebaked at 100 캜 for 3 minutes to form a colored curable composition layer. After cooling, an exposure amount of 80 mJ / cm &lt; 2 &gt; was formed in an atmospheric environment using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) with an interval of 200 mu m between the substrate on which the colored curable composition layer was formed and the quartz glass photomask (Based on 365 nm). As the photomask, a 100 μm line and space pattern was formed. The colored coating film after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 캜 for 70 seconds to develop and wash. This colored coating film was post-baked at 230 캜 for 30 minutes to obtain a colored pattern.

The film thickness of the obtained color pattern was measured using DEKTAK3 (manufactured by Japan Vacuum Technology Co., Ltd.). The film thickness of the colored pattern is shown in the column of &quot; film thickness &quot; in Table 27.

[Measurement of initial brightness]

Spectroscopy was measured using a colorimeter (OSP-SP-200, manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) in the XYZ color system of CIE were measured using the characteristic function of the C light source ) And the stimulus value Y were measured. The larger the value of Y, the higher the brightness.

[Evaluation of light resistance]

A light resistance tester (Line Test CPS + manufactured by Toyo Seiki Seisakusho Co., Ltd.) was placed on the obtained color pattern, and an ultraviolet cut filter (COLORED OPTICAL GLASS L38; HOYA CO., LTD. , A light resistance test was conducted in which xenon lamp light was irradiated for 15 hours. The relative value (%) of the stimulus value Y after the light resistance test when the stimulus value Y before the light resistance test (the initial lightness obtained above) is 100% is shown in the column of &quot; rate of lightness change &quot; The closer the brightness change rate is to 100%, the higher the light resistance.

Example 3-1

Pigment: C.I. Pigment Green 58  46 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Colorant (A): A compound represented by the formula (I-1)  21 parts, and

Pigment: C.I. Pigment Green 58  1.1 part

The total amount of the pigment composition,

Dispersant (BYK-LPN6919; manufactured by BICKEMI Japan Co., Ltd.)  26 parts,

Resin (B): Resin B1 solution  44 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 350 parts

(I-1) and a mixture of C.I. Pigment Green 58 was dispersed to obtain a colored composition.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained coloring composition;

Resin (B): Resin B6 solution 8.3 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

9.9 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.0 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE- 4.0 parts;

Adhesion promoter: 0.50 parts of 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.);

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 110 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

To obtain a colored curable composition 3-1.

A coloring pattern was obtained in the same manner as in Comparative Example 3 except that the comparative colored curable composition 3 was changed to the colored curable composition 3-1. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

Examples 3-2 to 3-60

Except that the compound represented by the formula (I-1) was replaced with the compound shown in the column of &quot; XXXXX &quot; in Table 27, the same procedure as in Example 3-1 was repeated, To obtain a colored pattern. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

[Table 27]

Examples 3A-1

Pigment: C.I. Pigment Green 58  46 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Colorant (A): Compound 136 21 parts, and

Pigment: C.I. Pigment Green 58 1.1 part

The total amount of the pigment composition,

Dispersant solution (solid content 60%)  26 parts,

Resin (B): Resin B1 solution  44 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 350 parts

Were mixed. Using a bead mill, the compound 136 and C.I. Pigment Green 58 was dispersed to obtain a colored composition.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained coloring composition;

Resin (B): Resin B6 solution 8.3 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

9.9 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.0 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE- 4.0 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.50 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 110 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

To obtain a colored curable composition 3A-1.

A coloring pattern was obtained in the same manner as in Comparative Example 3 except that the comparative colored curable composition 3 was changed to the colored curable composition 3A-1. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

Examples 3A-2 to 3A-231

The same procedure as in Example 3A-1 was conducted except that the compound 136 was changed to the compound shown in the column of &quot; XXXXX &quot; in Tables 28 to 31 to obtain a column of &quot; coloring curable composition &quot; To obtain a colored pattern. In addition, initial brightness and light resistance were evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 28 to 31.

[Table 28]

[Table 29]

[Table 30]

[Table 31]

Example 3B-1

Pigment: C.I. Pigment Green 58  46 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution    57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Colorant (A): Compound 136 21 parts, and

Pigment: C.I. Pigment Green 59 1.1 part

The total amount of the pigment composition,

Dispersant solution (solid content 60%)  26 parts,

Resin (B): Resin B1 solution  44 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 350 parts

Were mixed. Using a bead mill, the compound 136 and C.I. Pigment Green 58 was dispersed to obtain a colored composition.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained coloring composition;

Resin (B): Resin B6 solution 8.3 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

9.9 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.0 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE- 4.0 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.50 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 110 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

To obtain a colored curable composition 3B-1.

A coloring pattern was obtained in the same manner as in Comparative Example 3 except that the comparative colored curable composition 3 was changed to the colored curable composition 3B-1. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

Examples 3B-2 to 3B-231

In the same manner as in Example 3B-1 except that the compound 136 was changed to the compound shown in the column of &quot; XXXXX &quot; in Tables 32 to 35, the column of &quot; coloring curable composition &quot; To obtain a colored pattern. In addition, initial brightness and light resistance were evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 32 to 35.

[Table 32]

[Table 33]

[Table 34]

[Table 35]

Example 3C-1

Pigment: C.I. Pigment Green 58  46 parts,

Acrylic pigment dispersant 6.4 parts,

Resin (B): Resin B5 solution  57 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 220 parts

And a pigment dispersion (liquid containing the coloring agent (A2)) in which the pigment was dispersed using a bead mill was prepared. Separately,

Colorant (A): Compound 136  21 parts, and

Pigment: C.I. Pigment Green 7 1.1 part

The total amount of the pigment composition,

Dispersant solution (solid content 60%)  26 parts,

Resin (B): Resin B1 solution  44 parts, and

Solvent (E): Propylene glycol monomethyl ether acetate 350 parts

Were mixed. Using a bead mill, the compound 136 and C.I. Pigment Green 58 was dispersed to obtain a colored composition.

next,

The total amount of the obtained pigment dispersion (liquid containing the colorant (A2));

The total amount of the obtained coloring composition;

Resin (B): Resin B6 solution 8.3 parts;

Polymerizable compound (C): Polymerizable compound (A9570W; manufactured by Shin-Nakamura Chemical Co., Ltd.)

9.9 parts;

Polymerization initiator (D): A compound represented by the following formula (manufactured by Sangju Kogyo Kogyo Co., Ltd.)

5.0 parts;

Polymerization initiator (D): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE- 4.0 parts;

Adhesion promoter: 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.)

0.50 parts;

Solvent (E): 4-Hydroxy-4-methyl-2-pentanone  85 parts;

Solvent (E): Propylene glycol monomethyl ether acetate 110 parts; And

Leveling agent: Polyether-modified silicone oil (TORAYI Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.) 0.090 part;

To obtain a colored curable composition 3C-1.

A colored pattern was obtained in the same manner as in Comparative Example 3 except that the comparative colored curable composition 3 was changed to the colored curable composition 3C-1. In addition, initial brightness and light resistance were evaluated. The results are shown in the column of &quot; film thickness &quot; and &quot; brightness change rate &quot;

Examples 3C-2 to 3C-231

In the same manner as in Example 3C-1 except that the compound 136 was changed to the compound shown in the column of &quot; XXXXX &quot; in Tables 36 to 39, To obtain a colored pattern. In addition, initial brightness and light resistance were evaluated. The results are shown in the columns of "film thickness" and "brightness change rate" in Tables 36 to 39.

[Table 36]

[Table 37]

[Table 38]

[Table 39]

From the above results, the light fastness was improved in the coloring pattern formed from the colored curable composition containing the pigment composition of the present invention.

The pigment composition, coloring composition and colored curable composition of the present invention are suitably used for display devices such as color filters and liquid crystal displays, since they can be used for forming color filters having improved light resistance.

Claims (16)

The compound represented by the formula (I)
A quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I), and a green colorant.

[In the formula (I), L ¹ represents -CO- or -SO ₂ -.
R ¹ ~R ⁵ ~R ¹² and R ¹³ are, independently, a hydrogen ^{atom, -CO-R 102, -COO-} R 101, -OCO-R 102, -COCO-R 102, -OR 102, -SO each other _{^{2 -R 101, -SO 2 N (}} R 102) 2, -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102 , -OCON (R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent .
R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ may be bonded to each other to form a ring.
R ¹¹ and R ¹⁰¹ independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R ¹⁰² represents a hydrogen atom, a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When a plurality of R ¹⁰¹ , R ¹⁰² and M exist, they may be the same or different.
And the broken line represents E-form or Z-form. The method according to claim 1,
Wherein the compound represented by the formula (I) is a compound represented by the formula (I-a).

[In the formula (I-a), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.
L ² represents -CO- or -SO ₂ -.
R ¹⁴ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.] 3. The method of claim 2,
R ¹¹ and R ¹⁴ are the same group, and L ¹ and L ² are the same group. The method according to claim 2 or 3,
R ¹¹ and R ¹⁴ each independently represent an alkyl group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, A thienyl group which may be present, a furyl group which may have a substituent or a pyridinyl group which may have a substituent. The method according to claim 1,
Wherein the compound represented by the formula (I) is a compound represented by the formula (I-b).

[In the formula (I-b), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.
R ²⁰ and R ³⁰ combine to form a ring Q.
The ring Q may have a substituent, a ring having 5 to 7 ring members, and the ring Q may be a hydrocarbon ring or a heterocyclic ring. The ring Q may be a monocyclic ring having 5 to 7 ring members selected from a hydrocarbon ring and a heterocyclic ring, or an axial ring condensed with the monocyclic ring may be bonded. 6. The method of claim 5,
Wherein the compound represented by the formula (I) is a compound represented by the formula (I-c).

[In the formula (I-c), L ¹ , R ¹¹ , R ¹ to R ⁵ and the broken line have the same meanings as defined above.
R ⁶ and R ⁷ independently represent a hydrogen atom, -CO-R ¹⁰² , -COO-R ¹⁰¹ , -OCO-R ¹⁰² , -COCO-R ¹⁰² , -OR ¹⁰² , -SO ₂ -R ¹⁰¹ , _{^{SO 2 N (R 102) 2}} , -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102, -OCON (R 102 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R ¹⁰¹ , R ¹⁰² and M have the same meanings as defined above. 7. The method according to any one of claims 1 to 6,
R ¹ is a hydrogen atom and R ² to R ⁵ are independently of each other a hydrogen atom or a nitro group. A coloring composition comprising the pigment composition according to any one of claims 1 to 7 and a solvent. 9. The method of claim 8,
Further comprising a resin. 9. The method of claim 8,
Further, a coloring composition comprising a compound represented by the formula (I), a yellow coloring agent or a green coloring agent. A colored curable composition comprising the coloring composition according to claim 8 and a polymerizable compound. 12. The method of claim 11,
Further, a colored curable composition comprising a polymerization initiator. A color filter formed from the coloring composition or colored curable composition according to claim 8. A liquid crystal display device comprising the color filter according to claim 13. A pigment composition comprising a compound represented by the formula (I) and at least one member selected from the group consisting of a quinophthalone compound, an isoindoline compound other than the compound represented by the formula (I) and a green colorant, , A colorant (A2) and a colorant (A2) containing a solvent are mixed.

[In the formula (I), L ¹ represents -CO- or -SO ₂ -.
R ¹ ~R ⁵ ~R ¹² and R ¹³ are, independently, a hydrogen ^{atom, -CO-R 102, -COO-} R 101, -OCO-R 102, -COCO-R 102, -OR 102, -SO each other _{^{2 -R 101, -SO 2 N (}} R 102) 2, -CON (R 102) 2, -N (R 102) 2, -NHCO-R 102, -NHCO-N (R 102) 2, -NHCOOR 102 , -OCON (R ¹⁰² ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent .
R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ^5, and R ¹² and R ¹³ may be bonded to each other to form a ring.
R ¹¹ and R ¹⁰¹ independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R ¹⁰² represents a hydrogen atom, a hydrocarbon group of 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When a plurality of R ¹⁰¹ , R ¹⁰² and M exist, they may be the same or different.
And the broken line represents E-form or Z-form. 16. The method of claim 15,
Wherein the colorant (A2) is at least one colorant selected from a compound represented by the formula (I), a green colorant, and a yellow colorant.